# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2011


data_global

_journal_coden_Cambridge         1475

loop_
_publ_author_name
'Liu, Jianzhao'
'Deng, Chunmei'
'Chan, Carrie'
'Yue, Yanan'
'Ng, Jason'
'Lam, Jacky Wing Yip'
'Hong, Yuning'
'Sung, Herman'
'Williams, Ian'
'Tang, Ben'

_publ_contact_author_name        'Tang, Ben'
_publ_contact_author_email       tangbenz@ust.hk

_publ_section_title              
;
A new polymerisation route to conjugated polymers: Regio-
and stereoselective synthesis of linear and hyperbranched
poly(arylene chlorovinylene)s by decarbonylative
polyaddition of aroyl chlorides and alkynes
;
#TrackingRef '- Crystal 8.cif'

_publ_requested_journal          ?

# Attachment '- Crystal 8.cif'

data_JIAN9CULT
_database_code_depnum_ccdc_archive 'CCDC 826225'
_audit_creation_method           SHELXL-97
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H16 Cl2'
_chemical_formula_sum            'C22 H16 Cl2'
_chemical_formula_weight         351.25
_chemical_melting_point          ?
_chemical_name_common            ?
_chemical_name_systematic        ?
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.24573(8)
_cell_length_b                   7.28740(10)
_cell_length_c                   37.2516(5)
_cell_measurement_reflns_used    4971
_cell_measurement_temperature    173
_cell_measurement_theta_max      71.3792
_cell_measurement_theta_min      9.3804
_cell_volume                     1695.51(4)
_exptl_absorpt_coefficient_mu    3.413
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.56208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_F_000             728
_exptl_crystal_colour            ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_exptl_special_details           ?
_diffrn_ambient_temperature      173.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 15.9578
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega 46.00 72.50 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 -90.0000 53

#__ type_ start__ end____ width___ exp.time_
2 omega 42.00 83.50 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 90.0000 83

#__ type_ start__ end____ width___ exp.time_
3 omega 50.00 79.50 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
4 omega 27.00 118.50 0.5000 6.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 77.0000 -30.0000 183

#__ type_ start__ end____ width___ exp.time_
5 omega 85.00 119.50 0.5000 6.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 125.0000 -30.0000 69

#__ type_ start__ end____ width___ exp.time_
6 omega 81.00 135.00 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 111.0000 150.0000 108

#__ type_ start__ end____ width___ exp.time_
7 omega 43.00 91.00 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -114.0000 99.0000 96

#__ type_ start__ end____ width___ exp.time_
8 omega 37.00 70.00 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 120.0000 66

#__ type_ start__ end____ width___ exp.time_
9 omega 49.00 76.00 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
10 omega 39.00 71.50 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 60.0000 65

#__ type_ start__ end____ width___ exp.time_
11 omega 39.00 64.50 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 30.0000 51

#__ type_ start__ end____ width___ exp.time_
12 omega 43.00 70.00 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 -30.0000 54

#__ type_ start__ end____ width___ exp.time_
13 omega 140.00 170.00 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 111.0000 150.0000 60

#__ type_ start__ end____ width___ exp.time_
14 omega 38.00 70.50 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -25.0000 0.0000 65

#__ type_ start__ end____ width___ exp.time_
15 omega 49.00 76.00 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 -60.0000 54

#__ type_ start__ end____ width___ exp.time_
16 omega 57.00 83.50 0.5000 20.0000
omega____ theta____ kappa____ phi______ frames
- 110.0000 -50.0000 150.0000 53

#__ type_ start__ end____ width___ exp.time_
17 omega 26.00 121.50 0.5000 6.0000
omega____ theta____ kappa____ phi______ frames
- 55.0000 77.0000 30.0000 191
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0899606
_diffrn_orient_matrix_UB_12      0.1688691
_diffrn_orient_matrix_UB_13      -0.0198204
_diffrn_orient_matrix_UB_21      -0.0576214
_diffrn_orient_matrix_UB_22      -0.1217508
_diffrn_orient_matrix_UB_23      -0.0324036
_diffrn_orient_matrix_UB_31      -0.2222014
_diffrn_orient_matrix_UB_32      -0.036762
_diffrn_orient_matrix_UB_33      0.0163985
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            5408
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.48
_diffrn_reflns_theta_min         9.39
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2937
_reflns_number_total             3017
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material  
;
OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0258
_refine_ls_abs_structure_Flack   0.001(12)
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0717
_refine_ls_weighting_details     
;
calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.1871P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_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.
;
_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
Cl2 Cl 0.88127(5) 0.50421(6) 0.583266(9) 0.03892(11) Uani 1 1 d . . .
Cl1 Cl 0.87829(5) 0.51508(7) 0.400224(10) 0.04395(12) Uani 1 1 d . . .
C12 C 0.6078(2) 0.52317(19) 0.38865(4) 0.0261(3) Uani 1 1 d . . .
C1 C 0.4690(2) 0.5060(2) 0.45308(4) 0.0266(3) Uani 1 1 d . . .
C4 C 0.4712(2) 0.48661(19) 0.52913(4) 0.0262(3) Uani 1 1 d . . .
C21 C 0.4606(2) 0.4682(2) 0.56824(4) 0.0279(3) Uani 1 1 d . . .
H21 H 0.3203 0.4465 0.5771 0.033 Uiso 1 1 calc R . .
C11 C 0.4561(2) 0.51158(19) 0.41392(4) 0.0289(3) Uani 1 1 d . . .
H11 H 0.3143 0.5059 0.4047 0.035 Uiso 1 1 calc R . .
C23 C 0.5669(2) 0.45895(19) 0.63279(4) 0.0281(3) Uani 1 1 d . . .
C3 C 0.3060(2) 0.40738(19) 0.50892(4) 0.0278(3) Uani 1 1 d . . .
H3 H 0.1926 0.3458 0.5209 0.033 Uiso 1 1 calc R . .
C16 C 0.4752(3) 0.5729(2) 0.27638(4) 0.0404(4) Uani 1 1 d . . .
H16 H 0.4449 0.5843 0.2515 0.048 Uiso 1 1 calc R . .
C22 C 0.6108(2) 0.47589(18) 0.59393(4) 0.0270(3) Uani 1 1 d . . .
C27 C 0.3335(3) 0.5170(2) 0.68330(4) 0.0384(3) Uani 1 1 d . . .
H27 H 0.2044 0.5669 0.6926 0.046 Uiso 1 1 calc R . .
C28 C 0.3773(2) 0.5306(2) 0.64697(4) 0.0318(3) Uani 1 1 d . . .
H28 H 0.2775 0.5892 0.6315 0.038 Uiso 1 1 calc R . .
C15 C 0.6594(3) 0.4867(2) 0.28771(4) 0.0399(3) Uani 1 1 d . . .
H15 H 0.7556 0.4376 0.2704 0.048 Uiso 1 1 calc R . .
C2 C 0.3052(2) 0.4172(2) 0.47199(4) 0.0288(3) Uani 1 1 d . . .
H2 H 0.1907 0.3625 0.4590 0.035 Uiso 1 1 calc R . .
C24 C 0.7108(3) 0.3731(2) 0.65603(4) 0.0342(3) Uani 1 1 d . . .
H24 H 0.8411 0.3245 0.6469 0.041 Uiso 1 1 calc R . .
C5 C 0.6301(2) 0.58311(19) 0.51027(4) 0.0315(3) Uani 1 1 d . . .
H5 H 0.7402 0.6438 0.5232 0.038 Uiso 1 1 calc R . .
C26 C 0.4772(3) 0.4309(2) 0.70618(4) 0.0405(4) Uani 1 1 d . . .
H26 H 0.4472 0.4219 0.7311 0.049 Uiso 1 1 calc R . .
C25 C 0.6646(3) 0.3583(2) 0.69240(4) 0.0404(4) Uani 1 1 d . . .
H25 H 0.7625 0.2978 0.7079 0.049 Uiso 1 1 calc R . .
C6 C 0.6294(2) 0.5914(2) 0.47343(4) 0.0321(3) Uani 1 1 d . . .
H6 H 0.7402 0.6566 0.4615 0.039 Uiso 1 1 calc R . .
C17 C 0.3340(3) 0.6431(2) 0.30174(4) 0.0379(4) Uani 1 1 d . . .
H17 H 0.2061 0.7019 0.2941 0.046 Uiso 1 1 calc R . .
C13 C 0.5652(2) 0.53995(19) 0.34971(4) 0.0270(3) Uani 1 1 d . . .
C18 C 0.3785(3) 0.6278(2) 0.33804(4) 0.0319(3) Uani 1 1 d . . .
H18 H 0.2816 0.6773 0.3551 0.038 Uiso 1 1 calc R . .
C14 C 0.7067(2) 0.4706(2) 0.32410(4) 0.0336(3) Uani 1 1 d . . .
H14 H 0.8354 0.4124 0.3315 0.040 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
Cl2 0.02274(17) 0.0576(2) 0.03645(19) -0.00536(17) -0.00013(12) -0.00321(17)
Cl1 0.02367(17) 0.0731(3) 0.03506(19) 0.00622(19) -0.00070(12) 0.0082(2)
C12 0.0237(6) 0.0267(6) 0.0281(6) 0.0008(5) -0.0007(5) 0.0004(6)
C1 0.0262(6) 0.0256(6) 0.0279(6) -0.0007(6) 0.0008(5) 0.0014(6)
C4 0.0245(6) 0.0253(6) 0.0287(6) -0.0032(6) 0.0004(5) 0.0029(6)
C21 0.0237(6) 0.0312(7) 0.0288(7) -0.0020(6) 0.0023(5) 0.0001(6)
C11 0.0235(6) 0.0331(7) 0.0300(7) -0.0006(6) -0.0004(5) -0.0022(6)
C23 0.0282(6) 0.0261(6) 0.0298(7) -0.0043(5) -0.0043(5) -0.0012(5)
C3 0.0219(6) 0.0314(7) 0.0302(7) 0.0001(6) 0.0020(5) -0.0007(5)
C16 0.0481(9) 0.0449(9) 0.0282(7) 0.0027(6) -0.0038(7) -0.0052(7)
C22 0.0228(6) 0.0273(6) 0.0309(6) -0.0045(5) 0.0006(5) 0.0018(6)
C27 0.0390(7) 0.0431(8) 0.0330(7) -0.0020(7) 0.0027(6) -0.0007(7)
C28 0.0314(7) 0.0339(7) 0.0300(7) -0.0002(6) -0.0013(6) 0.0021(7)
C15 0.0430(8) 0.0437(8) 0.0329(7) -0.0015(7) 0.0112(6) 0.0002(8)
C2 0.0220(6) 0.0330(7) 0.0315(7) -0.0024(6) -0.0022(6) -0.0038(5)
C24 0.0328(7) 0.0337(7) 0.0361(7) -0.0020(6) -0.0063(6) 0.0026(6)
C5 0.0300(7) 0.0317(7) 0.0326(7) -0.0034(6) -0.0032(6) -0.0077(6)
C26 0.0485(9) 0.0457(9) 0.0272(7) 0.0009(6) -0.0026(7) -0.0105(7)
C25 0.0451(9) 0.0394(8) 0.0367(8) 0.0046(6) -0.0148(7) -0.0017(7)
C6 0.0306(7) 0.0312(7) 0.0345(7) -0.0005(6) 0.0021(6) -0.0080(6)
C17 0.0370(8) 0.0420(8) 0.0348(7) 0.0022(6) -0.0057(7) 0.0031(7)
C13 0.0272(6) 0.0251(6) 0.0288(7) 0.0008(5) 0.0027(5) -0.0015(5)
C18 0.0304(7) 0.0340(7) 0.0314(7) -0.0006(6) -0.0002(6) 0.0040(6)
C14 0.0315(7) 0.0358(8) 0.0336(7) 0.0011(6) 0.0049(6) 0.0025(6)

_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 C22 1.7475(13) . ?
Cl1 C12 1.7445(13) . ?
C12 C11 1.3382(19) . ?
C12 C13 1.4800(18) . ?
C1 C11 1.4617(18) . ?
C1 C2 1.4007(19) . ?
C1 C6 1.402(2) . ?
C4 C21 1.4647(18) . ?
C4 C3 1.4016(19) . ?
C4 C5 1.405(2) . ?
C21 C22 1.341(2) . ?
C23 C22 1.4784(19) . ?
C23 C28 1.398(2) . ?
C23 C24 1.396(2) . ?
C3 C2 1.378(2) . ?
C16 C15 1.377(3) . ?
C16 C17 1.389(2) . ?
C27 C28 1.384(2) . ?
C27 C26 1.388(2) . ?
C15 C14 1.393(2) . ?
C24 C25 1.390(2) . ?
C5 C6 1.374(2) . ?
C26 C25 1.383(3) . ?
C17 C18 1.385(2) . ?
C13 C18 1.400(2) . ?
C13 C14 1.395(2) . ?

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
C12 C11 C1 131.65(12) . . ?
C21 C22 Cl2 121.26(11) . . ?
C21 C22 C23 124.43(12) . . ?
C11 C12 Cl1 120.65(11) . . ?
C11 C12 C13 124.57(12) . . ?
C23 C22 Cl2 114.30(10) . . ?
C3 C4 C21 117.61(12) . . ?
C3 C4 C5 117.23(13) . . ?
C3 C2 C1 121.56(13) . . ?
C16 C15 C14 120.91(15) . . ?
C22 C21 C4 132.41(13) . . ?
C27 C28 C23 120.70(14) . . ?
C28 C23 C22 119.73(12) . . ?
C28 C27 C26 120.29(15) . . ?
C15 C16 C17 119.33(14) . . ?
C15 C14 C13 120.06(14) . . ?
C2 C1 C11 118.32(12) . . ?
C2 C1 C6 117.08(13) . . ?
C2 C3 C4 121.19(13) . . ?
C24 C23 C22 121.70(13) . . ?
C24 C23 C28 118.57(14) . . ?
C5 C4 C21 125.13(13) . . ?
C5 C6 C1 121.52(14) . . ?
C26 C25 C24 120.51(15) . . ?
C25 C24 C23 120.39(15) . . ?
C25 C26 C27 119.52(15) . . ?
C6 C1 C11 124.52(13) . . ?
C6 C5 C4 121.30(14) . . ?
C17 C18 C13 120.49(14) . . ?
C13 C12 Cl1 114.78(9) . . ?
C18 C17 C16 120.44(15) . . ?
C18 C13 C12 119.48(12) . . ?
C14 C13 C12 121.77(13) . . ?
C14 C13 C18 118.76(13) . . ?
# Attachment '- Crystal 9.cif'

data_jian15
_database_code_depnum_ccdc_archive 'CCDC 826226'
#TrackingRef '- Crystal 9.cif'

_audit_creation_date             2011-02-07
_audit_creation_method           
;
Olex2 1.1-beta
(compiled 2011.01.21 svn.r1625, GUI svn.r3464)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C30 H21 Cl3'
_chemical_formula_sum            'C30 H21 Cl3'
_chemical_formula_weight         487.82
_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 0.0033 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'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   R3c

_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 '-x+y, y, z+1/2'
5 'x, x-y, z+1/2'
6 '-y, -x, z+1/2'
7 'x+2/3, y+1/3, z+1/3'
8 '-y+2/3, x-y+1/3, z+1/3'
9 '-x+y+2/3, -x+1/3, z+1/3'
10 '-x+y+2/3, y+1/3, z+5/6'
11 'x+2/3, x-y+1/3, z+5/6'
12 '-y+2/3, -x+1/3, z+5/6'
13 'x+1/3, y+2/3, z+2/3'
14 '-y+1/3, x-y+2/3, z+2/3'
15 '-x+y+1/3, -x+2/3, z+2/3'
16 '-x+y+1/3, y+2/3, z+7/6'
17 'x+1/3, x-y+2/3, z+7/6'
18 '-y+1/3, -x+2/3, z+7/6'

_cell_length_a                   24.8014(16)
_cell_length_b                   24.8014(16)
_cell_length_c                   6.8350(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3641.0(6)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2960
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.85
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.916220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0255 before and 0.0160 after correction.
The Ratio of minimum to maximum transmission is 0.916220.
The \l/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
The data collection nominally covered a full sphere of reciprocal space by
a combination of 5 sets of \w scans each set at different \f and/or
2\q angles and each scan (10.00 s exposure) covering -0.300\ degrees in \w.
The crystal to detector distance was 6.0 cm.
;
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6926
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         1.64
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_target            MO
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1554
_reflns_number_total             1603
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'smtbx-flip (Bourhis, 2008)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1603
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.070
_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^)+(0.0594P)^2^+0.1693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0834
_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.
;
_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
Cl1 Cl 0.72361(2) 0.52440(2) 0.40764(8) 0.03350(16) Uani 1 1 d . . .
C1 C 0.65080(9) 0.48296(9) 0.2933(3) 0.0260(4) Uani 1 1 d . . .
C2 C 0.62637(9) 0.42338(9) 0.2442(3) 0.0235(4) Uani 1 1 d . . .
H2 H 0.5858 0.4059 0.1902 0.028 Uiso 1 1 calc R . .
C3 C 0.64900(8) 0.37886(8) 0.2559(3) 0.0201(4) Uani 1 1 d . . .
C4 C 0.60426(8) 0.31611(8) 0.2553(3) 0.0215(4) Uani 1 1 d . . .
H4 H 0.5614 0.3042 0.2543 0.026 Uiso 1 1 calc R . .
C5 C 0.61896(9) 0.51981(8) 0.2603(3) 0.0271(4) Uani 1 1 d . . .
C6 C 0.62214(10) 0.56221(10) 0.4004(4) 0.0356(5) Uani 1 1 d . . .
H6 H 0.6451 0.5683 0.5176 0.043 Uiso 1 1 calc R . .
C7 C 0.59172(12) 0.59537(11) 0.3676(4) 0.0445(6) Uani 1 1 d . . .
H7 H 0.5939 0.6242 0.4631 0.053 Uiso 1 1 calc R . .
C8 C 0.55838(11) 0.58701(11) 0.1981(5) 0.0491(6) Uani 1 1 d . . .
H8 H 0.5378 0.6101 0.1769 0.059 Uiso 1 1 calc R . .
C9 C 0.55496(12) 0.54506(12) 0.0591(5) 0.0499(7) Uani 1 1 d . . .
H9 H 0.5318 0.5390 -0.0576 0.060 Uiso 1 1 calc R . .
C10 C 0.58566(11) 0.51168(10) 0.0903(4) 0.0381(5) Uani 1 1 d . . .
H10 H 0.5837 0.4831 -0.0060 0.046 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 0.0292(3) 0.0250(2) 0.0450(3) -0.0077(2) -0.0126(2) 0.0126(2)
C1 0.0233(9) 0.0251(9) 0.0276(11) 0.0003(7) 0.0025(7) 0.0105(8)
C2 0.0207(8) 0.0222(9) 0.0255(9) 0.0009(7) 0.0004(7) 0.0091(7)
C3 0.0251(9) 0.0235(8) 0.0126(8) -0.0014(6) -0.0013(6) 0.0129(7)
C4 0.0214(8) 0.0254(9) 0.0176(9) -0.0012(7) -0.0008(6) 0.0117(7)
C5 0.0220(8) 0.0174(8) 0.0389(11) 0.0014(8) 0.0029(8) 0.0075(7)
C6 0.0336(11) 0.0293(10) 0.0447(13) -0.0010(9) 0.0060(9) 0.0163(9)
C7 0.0365(12) 0.0317(11) 0.0683(17) -0.0030(11) 0.0118(12) 0.0194(10)
C8 0.0262(11) 0.0306(11) 0.096(2) 0.0063(12) 0.0011(11) 0.0181(9)
C9 0.0332(12) 0.0352(13) 0.078(2) -0.0020(12) -0.0202(12) 0.0147(10)
C10 0.0348(11) 0.0242(10) 0.0525(14) -0.0040(9) -0.0078(10) 0.0127(9)

_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 C1 1.753(2) . ?
C1 C2 1.330(3) . ?
C1 C5 1.494(3) . ?
C2 C3 1.470(3) . ?
C3 C4 1.397(3) 3_665 ?
C3 C4 1.388(3) . ?
C4 C3 1.397(3) 2_655 ?
C5 C6 1.395(3) . ?
C5 C10 1.381(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.378(4) . ?
C8 C9 1.380(4) . ?
C9 C10 1.393(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
C2 C1 Cl1 121.85(16) . . ?
C2 C1 C5 123.73(18) . . ?
C5 C1 Cl1 114.42(14) . . ?
C1 C2 C3 133.48(18) . . ?
C4 C3 C2 124.23(16) 3_665 . ?
C4 C3 C2 116.79(16) . . ?
C4 C3 C4 118.85(18) . 3_665 ?
C3 C4 C3 121.14(18) . 2_655 ?
C6 C5 C1 120.64(19) . . ?
C10 C5 C1 119.88(17) . . ?
C10 C5 C6 119.5(2) . . ?
C7 C6 C5 119.7(2) . . ?
C8 C7 C6 120.7(2) . . ?
C7 C8 C9 119.9(2) . . ?
C8 C9 C10 119.8(2) . . ?
C5 C10 C9 120.5(2) . . ?