# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_C13H15I
_database_code_depnum_ccdc_archive 'CCDC 1007894'
_audit_update_record             
;
2014-06-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 I'
_chemical_formula_weight         298.15

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.350(5)
_cell_length_b                   31.01(3)
_cell_length_c                   6.458(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.526(13)
_cell_angle_gamma                90.00
_cell_volume                     1174.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2535
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.77

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    2.687
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6319
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2055
_reflns_number_gt                1483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2055
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8242(9) 0.08922(19) 0.2594(9) 0.0527(14) Uani 1 1 d . . .
H1 H 0.8888 0.1066 0.1713 0.063 Uiso 1 1 calc R . .
C2 C 0.6737(12) 0.0513(2) 0.1328(11) 0.0700(18) Uani 1 1 d . . .
H2A H 0.7658 0.0269 0.1259 0.084 Uiso 1 1 calc R . .
H2B H 0.5760 0.0597 -0.0185 0.084 Uiso 1 1 calc R . .
C3 C 0.5320(11) 0.0408(2) 0.2742(10) 0.0641(17) Uani 1 1 d . . .
H3A H 0.5601 0.0115 0.3313 0.077 Uiso 1 1 calc R . .
H3B H 0.3703 0.0443 0.1869 0.077 Uiso 1 1 calc R . .
C4 C 0.6174(8) 0.07396(17) 0.4669(8) 0.0451(12) Uani 1 1 d . . .
H4 H 0.5127 0.0792 0.5431 0.054 Uiso 1 1 calc R . .
C5 C 0.8610(9) 0.06104(18) 0.6228(9) 0.0564(15) Uani 1 1 d . . .
H5A H 0.9125 0.0778 0.7599 0.068 Uiso 1 1 calc R . .
H5B H 0.8691 0.0306 0.6603 0.068 Uiso 1 1 calc R . .
C6 C 1.0015(10) 0.0711(2) 0.4836(11) 0.0627(16) Uani 1 1 d . . .
H6A H 1.0737 0.0452 0.4574 0.075 Uiso 1 1 calc R . .
H6B H 1.1182 0.0923 0.5578 0.075 Uiso 1 1 calc R . .
C7 C 0.6713(8) 0.11406(16) 0.3535(7) 0.0375(11) Uani 1 1 d . . .
C8 C 0.7758(8) 0.15288(16) 0.4991(8) 0.0413(12) Uani 1 1 d . . .
C9 C 0.9445(9) 0.17759(17) 0.4774(10) 0.0569(15) Uani 1 1 d . . .
H9 H 1.0011 0.1705 0.3686 0.068 Uiso 1 1 calc R . .
C10 C 1.0336(12) 0.2133(2) 0.6150(14) 0.076(2) Uani 1 1 d . . .
H10 H 1.1471 0.2298 0.5958 0.092 Uiso 1 1 calc R . .
C11 C 0.9557(14) 0.2241(2) 0.7759(13) 0.087(3) Uani 1 1 d . . .
H11 H 1.0165 0.2478 0.8673 0.104 Uiso 1 1 calc R . .
C12 C 0.7871(13) 0.2000(2) 0.8047(11) 0.076(2) Uani 1 1 d . . .
H12 H 0.7337 0.2076 0.9153 0.091 Uiso 1 1 calc R . .
C13 C 0.6962(10) 0.16450(18) 0.6684(9) 0.0542(14) Uani 1 1 d . . .
H13 H 0.5824 0.1483 0.6886 0.065 Uiso 1 1 calc R . .
I1 I 0.36499(6) 0.141039(14) 0.08631(6) 0.0624(2) Uani 1 1 d . . .

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 0.050(3) 0.063(3) 0.058(3) -0.009(3) 0.036(3) -0.001(3)
C2 0.086(5) 0.069(4) 0.061(4) -0.027(3) 0.035(3) -0.011(4)
C3 0.067(4) 0.060(4) 0.065(4) -0.014(3) 0.026(3) -0.023(3)
C4 0.049(3) 0.048(3) 0.043(3) -0.006(2) 0.022(2) -0.011(3)
C5 0.066(4) 0.044(3) 0.050(3) 0.001(2) 0.011(3) 0.003(3)
C6 0.045(3) 0.052(3) 0.090(4) -0.017(3) 0.024(3) 0.005(3)
C7 0.033(2) 0.047(3) 0.032(2) 0.0001(19) 0.0116(19) -0.004(2)
C8 0.038(3) 0.041(3) 0.033(2) 0.0103(19) 0.000(2) 0.000(2)
C9 0.050(3) 0.047(3) 0.067(4) 0.004(3) 0.016(3) -0.012(3)
C10 0.068(4) 0.053(4) 0.088(5) 0.006(3) 0.007(4) -0.024(3)
C11 0.095(6) 0.050(4) 0.071(5) -0.008(3) -0.017(4) -0.004(4)
C12 0.104(5) 0.062(4) 0.054(3) -0.014(3) 0.021(4) 0.015(4)
C13 0.071(4) 0.046(3) 0.048(3) -0.003(2) 0.026(3) 0.000(3)
I1 0.0457(3) 0.0855(3) 0.0435(2) 0.00633(19) 0.00302(16) -0.0022(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
C1 C7 1.535(7) . ?
C1 C2 1.537(8) . ?
C1 C6 1.559(8) . ?
C2 C3 1.542(9) . ?
C3 C4 1.544(7) . ?
C4 C5 1.540(7) . ?
C4 C7 1.547(7) . ?
C5 C6 1.521(9) . ?
C7 C8 1.515(7) . ?
C7 I1 2.211(5) . ?
C8 C9 1.367(7) . ?
C8 C13 1.415(8) . ?
C9 C10 1.397(9) . ?
C10 C11 1.352(11) . ?
C11 C12 1.375(10) . ?
C12 C13 1.390(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C1 C2 103.6(4) . . ?
C7 C1 C6 98.9(4) . . ?
C2 C1 C6 107.4(5) . . ?
C1 C2 C3 103.4(5) . . ?
C2 C3 C4 103.4(4) . . ?
C5 C4 C3 107.9(5) . . ?
C5 C4 C7 99.8(4) . . ?
C3 C4 C7 103.1(4) . . ?
C6 C5 C4 103.3(4) . . ?
C5 C6 C1 104.1(4) . . ?
C8 C7 C1 116.8(4) . . ?
C8 C7 C4 117.9(4) . . ?
C1 C7 C4 94.1(4) . . ?
C8 C7 I1 103.2(3) . . ?
C1 C7 I1 112.4(3) . . ?
C4 C7 I1 112.7(3) . . ?
C9 C8 C13 117.5(5) . . ?
C9 C8 C7 123.7(5) . . ?
C13 C8 C7 118.7(5) . . ?
C8 C9 C10 121.4(7) . . ?
C11 C10 C9 120.4(7) . . ?
C10 C11 C12 120.2(6) . . ?
C11 C12 C13 120.0(7) . . ?
C12 C13 C8 120.4(6) . . ?

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
C7 C1 C2 C3 -34.1(6) . . . . ?
C6 C1 C2 C3 70.0(6) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -71.3(6) . . . . ?
C2 C3 C4 C7 33.7(6) . . . . ?
C3 C4 C5 C6 70.7(5) . . . . ?
C7 C4 C5 C6 -36.6(5) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C7 C1 C6 C5 36.4(5) . . . . ?
C2 C1 C6 C5 -71.0(5) . . . . ?
C2 C1 C7 C8 177.2(5) . . . . ?
C6 C1 C7 C8 66.7(5) . . . . ?
C2 C1 C7 C4 52.9(5) . . . . ?
C6 C1 C7 C4 -57.5(4) . . . . ?
C2 C1 C7 I1 -63.7(5) . . . . ?
C6 C1 C7 I1 -174.2(3) . . . . ?
C5 C4 C7 C8 -64.9(5) . . . . ?
C3 C4 C7 C8 -176.0(4) . . . . ?
C5 C4 C7 C1 58.5(4) . . . . ?
C3 C4 C7 C1 -52.6(5) . . . . ?
C5 C4 C7 I1 174.9(3) . . . . ?
C3 C4 C7 I1 63.8(5) . . . . ?
C1 C7 C8 C9 29.0(7) . . . . ?
C4 C7 C8 C9 140.0(5) . . . . ?
I1 C7 C8 C9 -95.0(5) . . . . ?
C1 C7 C8 C13 -150.8(5) . . . . ?
C4 C7 C8 C13 -39.8(6) . . . . ?
I1 C7 C8 C13 85.2(5) . . . . ?
C13 C8 C9 C10 -0.8(8) . . . . ?
C7 C8 C9 C10 179.4(5) . . . . ?
C8 C9 C10 C11 0.7(10) . . . . ?
C9 C10 C11 C12 -0.3(11) . . . . ?
C10 C11 C12 C13 0.1(10) . . . . ?
C11 C12 C13 C8 -0.2(9) . . . . ?
C9 C8 C13 C12 0.5(8) . . . . ?
C7 C8 C13 C12 -179.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.011
_refine_diff_density_min         -1.017
_refine_diff_density_rms         0.098
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C13H15Br
_database_code_depnum_ccdc_archive 'CCDC 1007895'
_audit_update_record             
;
2014-06-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Br'
_chemical_formula_weight         251.16

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.201(5)
_cell_length_b                   30.714(5)
_cell_length_c                   6.350(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 114.351(5)
_cell_angle_gamma                90.000
_cell_volume                     1101.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2019
_cell_measurement_theta_min      3.3164
_cell_measurement_theta_max      29.1705

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.3200
_exptl_crystal_size_mid          0.2300
_exptl_crystal_size_min          0.2200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    3.688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
'Wed Feb 05 15:30:59 2014' 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3317
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4416
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1866
_reflns_number_gt                1474
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
'Wed Feb 05 15:30:59 2014' 
;
_computing_cell_refinement       
; 
'Wed Feb 05 15:30:59 2014' 
;
_computing_data_reduction        
; 
'Wed Feb 05 15:30:59 2014' 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.6775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1866
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 1.12277(7) 0.139135(13) 0.38570(6) 0.06048(19) Uani 1 1 d . . .
C1 C 0.8875(6) 0.07408(10) 0.0279(6) 0.0385(8) Uani 1 1 d . . .
H1 H 0.9957 0.0787 -0.0471 0.046 Uiso 1 1 calc R . .
C2 C 0.9764(7) 0.04214(12) 0.2301(6) 0.0541(10) Uani 1 1 d . . .
H2A H 1.1445 0.0459 0.3230 0.065 Uiso 1 1 calc R . .
H2B H 0.9470 0.0123 0.1760 0.065 Uiso 1 1 calc R . .
C3 C 0.8307(8) 0.05418(13) 0.3684(7) 0.0596(11) Uani 1 1 d . . .
H3A H 0.7363 0.0297 0.3781 0.071 Uiso 1 1 calc R . .
H3B H 0.9325 0.0637 0.5234 0.071 Uiso 1 1 calc R . .
C4 C 0.6733(6) 0.09142(11) 0.2270(6) 0.0468(9) Uani 1 1 d . . .
H4 H 0.6066 0.1098 0.3113 0.056 Uiso 1 1 calc R . .
C5 C 0.4891(6) 0.07187(12) -0.0019(7) 0.0542(10) Uani 1 1 d . . .
H5A H 0.4161 0.0460 0.0274 0.065 Uiso 1 1 calc R . .
H5B H 0.3665 0.0929 -0.0846 0.065 Uiso 1 1 calc R . .
C6 C 0.6350(6) 0.06087(11) -0.1364(6) 0.0478(9) Uani 1 1 d . . .
H6A H 0.5814 0.0773 -0.2795 0.057 Uiso 1 1 calc R . .
H6B H 0.6263 0.0300 -0.1717 0.057 Uiso 1 1 calc R . .
C7 C 0.8314(5) 0.11517(10) 0.1337(5) 0.0355(7) Uani 1 1 d . . .
C8 C 0.7266(6) 0.15302(10) -0.0266(6) 0.0365(8) Uani 1 1 d . . .
C9 C 0.5489(6) 0.17853(11) -0.0132(7) 0.0533(10) Uani 1 1 d . . .
H9 H 0.4896 0.1722 0.0961 0.064 Uiso 1 1 calc R . .
C10 C 0.4587(8) 0.21348(13) -0.1615(9) 0.0716(13) Uani 1 1 d . . .
H10 H 0.3375 0.2302 -0.1528 0.086 Uiso 1 1 calc R . .
C11 C 0.5468(9) 0.22360(13) -0.3208(8) 0.0761(14) Uani 1 1 d . . .
H11 H 0.4880 0.2475 -0.4178 0.091 Uiso 1 1 calc R . .
C12 C 0.7202(9) 0.19869(13) -0.3370(7) 0.0683(12) Uani 1 1 d . . .
H12 H 0.7776 0.2051 -0.4476 0.082 Uiso 1 1 calc R . .
C13 C 0.8116(7) 0.16389(11) -0.1896(6) 0.0505(9) Uani 1 1 d . . .
H13 H 0.9326 0.1474 -0.2001 0.061 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
Br1 0.0479(2) 0.0721(3) 0.0437(3) -0.00715(19) 0.00099(18) -0.00311(18)
C1 0.0416(18) 0.0405(18) 0.0398(18) 0.0027(15) 0.0233(15) 0.0081(15)
C2 0.054(2) 0.051(2) 0.057(2) 0.0106(19) 0.022(2) 0.0158(18)
C3 0.074(3) 0.063(2) 0.049(2) 0.0136(19) 0.032(2) 0.004(2)
C4 0.048(2) 0.055(2) 0.050(2) 0.0071(17) 0.0337(18) 0.0083(17)
C5 0.0375(19) 0.050(2) 0.075(3) 0.014(2) 0.0232(19) -0.0044(17)
C6 0.058(2) 0.0372(18) 0.044(2) -0.0037(16) 0.0173(18) -0.0023(16)
C7 0.0288(16) 0.0444(18) 0.0312(18) 0.0009(14) 0.0102(14) 0.0033(14)
C8 0.0386(17) 0.0330(16) 0.0328(18) -0.0044(14) 0.0096(15) -0.0033(14)
C9 0.046(2) 0.047(2) 0.061(2) -0.0058(19) 0.0152(19) 0.0072(17)
C10 0.056(3) 0.045(2) 0.085(3) -0.013(2) 0.000(2) 0.0152(19)
C11 0.087(3) 0.043(2) 0.062(3) 0.009(2) -0.006(3) -0.001(2)
C12 0.091(3) 0.049(2) 0.052(2) 0.007(2) 0.016(2) -0.011(2)
C13 0.063(2) 0.040(2) 0.047(2) 0.0009(18) 0.0206(19) -0.0038(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
Br1 C7 1.996(3) . ?
C1 C2 1.527(5) . ?
C1 C7 1.536(4) . ?
C1 C6 1.536(5) . ?
C2 C3 1.543(5) . ?
C3 C4 1.531(5) . ?
C4 C7 1.523(5) . ?
C4 C5 1.552(5) . ?
C5 C6 1.516(5) . ?
C7 C8 1.505(4) . ?
C8 C13 1.382(5) . ?
C8 C9 1.383(5) . ?
C9 C10 1.385(6) . ?
C10 C11 1.369(7) . ?
C11 C12 1.358(7) . ?
C12 C13 1.379(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 103.2(3) . . ?
C2 C1 C6 108.4(3) . . ?
C7 C1 C6 99.4(2) . . ?
C1 C2 C3 103.4(3) . . ?
C4 C3 C2 103.1(3) . . ?
C7 C4 C5 99.5(3) . . ?
C7 C4 C3 103.3(3) . . ?
C5 C4 C3 107.8(3) . . ?
C6 C5 C4 103.5(3) . . ?
C5 C6 C1 103.7(3) . . ?
C8 C7 C4 117.7(3) . . ?
C8 C7 C1 116.8(3) . . ?
C4 C7 C1 94.3(3) . . ?
C8 C7 Br1 104.7(2) . . ?
C4 C7 Br1 112.3(2) . . ?
C1 C7 Br1 111.1(2) . . ?
C13 C8 C9 117.9(3) . . ?
C13 C8 C7 120.1(3) . . ?
C9 C8 C7 121.9(3) . . ?
C10 C9 C8 120.4(4) . . ?
C9 C10 C11 120.4(4) . . ?
C12 C11 C10 119.9(4) . . ?
C11 C12 C13 120.1(4) . . ?
C8 C13 C12 121.2(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
C7 C1 C2 C3 33.4(4) . . . . ?
C6 C1 C2 C3 -71.3(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C7 -34.6(4) . . . . ?
C2 C3 C4 C5 70.0(4) . . . . ?
C7 C4 C5 C6 35.6(3) . . . . ?
C3 C4 C5 C6 -71.7(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C2 C1 C6 C5 70.2(3) . . . . ?
C7 C1 C6 C5 -37.2(3) . . . . ?
C5 C4 C7 C8 65.9(3) . . . . ?
C3 C4 C7 C8 176.8(3) . . . . ?
C5 C4 C7 C1 -57.5(3) . . . . ?
C3 C4 C7 C1 53.4(3) . . . . ?
C5 C4 C7 Br1 -172.5(2) . . . . ?
C3 C4 C7 Br1 -61.5(3) . . . . ?
C2 C1 C7 C8 -177.1(3) . . . . ?
C6 C1 C7 C8 -65.6(3) . . . . ?
C2 C1 C7 C4 -53.0(3) . . . . ?
C6 C1 C7 C4 58.5(3) . . . . ?
C2 C1 C7 Br1 62.9(3) . . . . ?
C6 C1 C7 Br1 174.4(2) . . . . ?
C4 C7 C8 C13 -152.3(3) . . . . ?
C1 C7 C8 C13 -41.2(4) . . . . ?
Br1 C7 C8 C13 82.1(3) . . . . ?
C4 C7 C8 C9 29.3(4) . . . . ?
C1 C7 C8 C9 140.4(3) . . . . ?
Br1 C7 C8 C9 -96.2(3) . . . . ?
C13 C8 C9 C10 0.7(5) . . . . ?
C7 C8 C9 C10 179.1(3) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C10 C11 C12 C13 -1.5(6) . . . . ?
C9 C8 C13 C12 -0.9(5) . . . . ?
C7 C8 C13 C12 -179.3(3) . . . . ?
C11 C12 C13 C8 1.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.051
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_C13H15CL
_database_code_depnum_ccdc_archive 'CCDC 1007896'
_audit_update_record             
;
2014-06-11 deposited with the CCDC.
2015-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Cl'
_chemical_formula_weight         206.70

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.3915(4)
_cell_length_b                   6.8582(5)
_cell_length_c                   24.6067(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.259(7)
_cell_angle_gamma                90.00
_cell_volume                     1075.65(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1141
_cell_measurement_theta_min      3.3208
_cell_measurement_theta_max      29.5391

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.1800
_exptl_crystal_size_min          0.0900
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
'Wed Feb 05 17:14:49 2014' 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3317
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4401
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1891
_reflns_number_gt                1343
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
'Wed Feb 05 17:14:49 2014' 
;
_computing_cell_refinement       
; 
'Wed Feb 05 17:14:49 2014' 
;
_computing_data_reduction        
; 
'Wed Feb 05 17:14:49 2014' 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0330P)²+0.1485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1891
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.6823(3) 0.2556(3) 0.11839(8) 0.0414(6) Uani 1 1 d . . .
H1 H 0.5805 0.2060 0.1429 0.050 Uiso 1 1 calc R . .
C2 C 0.8382(4) 0.4064(4) 0.14411(10) 0.0519(7) Uani 1 1 d . . .
H2A H 0.8847 0.3704 0.1812 0.062 Uiso 1 1 calc R . .
H2B H 0.7758 0.5353 0.1442 0.062 Uiso 1 1 calc R . .
C3 C 1.0214(4) 0.3994(4) 0.10675(10) 0.0537(7) Uani 1 1 d . . .
H3A H 1.0425 0.5253 0.0901 0.064 Uiso 1 1 calc R . .
H3B H 1.1506 0.3594 0.1268 0.064 Uiso 1 1 calc R . .
C4 C 0.9487(3) 0.2469(4) 0.06385(9) 0.0454(6) Uani 1 1 d . . .
H4 H 1.0616 0.1899 0.0441 0.054 Uiso 1 1 calc R . .
C5 C 0.7693(4) 0.3358(4) 0.02742(10) 0.0574(7) Uani 1 1 d . . .
H5A H 0.7353 0.2552 -0.0044 0.069 Uiso 1 1 calc R . .
H5B H 0.8046 0.4659 0.0157 0.069 Uiso 1 1 calc R . .
C6 C 0.5860(4) 0.3410(4) 0.06477(9) 0.0521(7) Uani 1 1 d . . .
H6A H 0.5379 0.4735 0.0698 0.063 Uiso 1 1 calc R . .
H6B H 0.4693 0.2623 0.0499 0.063 Uiso 1 1 calc R . .
C7 C 0.8369(3) 0.1025(3) 0.09958(8) 0.0361(5) Uani 1 1 d . . .
C8 C 0.9691(3) -0.0063(3) 0.14280(9) 0.0391(6) Uani 1 1 d . . .
C9 C 1.1685(4) -0.0707(4) 0.13349(11) 0.0534(7) Uani 1 1 d . . .
H9 H 1.2240 -0.0422 0.1005 0.064 Uiso 1 1 calc R . .
C10 C 1.2863(4) -0.1764(4) 0.17248(14) 0.0709(9) Uani 1 1 d . . .
H10 H 1.4194 -0.2200 0.1654 0.085 Uiso 1 1 calc R . .
C11 C 1.2076(5) -0.2174(4) 0.22149(14) 0.0759(9) Uani 1 1 d . . .
H11 H 1.2877 -0.2872 0.2479 0.091 Uiso 1 1 calc R . .
C12 C 1.0113(5) -0.1553(4) 0.23129(11) 0.0694(8) Uani 1 1 d . . .
H12 H 0.9574 -0.1838 0.2645 0.083 Uiso 1 1 calc R . .
C13 C 0.8919(4) -0.0505(4) 0.19244(9) 0.0511(7) Uani 1 1 d . . .
H13 H 0.7583 -0.0091 0.1997 0.061 Uiso 1 1 calc R . .
Cl1 Cl 0.69974(9) -0.08634(9) 0.05829(2) 0.0543(2) Uani 1 1 d . . .

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 0.0416(12) 0.0421(14) 0.0410(13) -0.0023(12) 0.0071(11) -0.0012(11)
C2 0.0634(15) 0.0373(15) 0.0536(15) -0.0085(12) -0.0046(13) 0.0007(13)
C3 0.0518(14) 0.0411(16) 0.0672(16) 0.0056(13) -0.0028(13) -0.0129(12)
C4 0.0445(12) 0.0473(15) 0.0453(13) 0.0027(12) 0.0098(11) -0.0030(12)
C5 0.0655(15) 0.0593(18) 0.0465(14) 0.0132(14) -0.0026(13) -0.0085(15)
C6 0.0508(13) 0.0482(16) 0.0561(15) 0.0030(14) -0.0044(12) 0.0025(13)
C7 0.0388(11) 0.0364(14) 0.0330(11) -0.0068(10) 0.0017(10) -0.0074(10)
C8 0.0412(12) 0.0309(13) 0.0440(13) -0.0030(11) -0.0039(11) -0.0071(11)
C9 0.0461(13) 0.0474(16) 0.0657(16) -0.0032(14) -0.0022(13) 0.0003(13)
C10 0.0531(15) 0.0545(19) 0.102(2) -0.0093(19) -0.0182(17) 0.0108(15)
C11 0.089(2) 0.0489(19) 0.084(2) 0.0081(17) -0.0353(19) 0.0014(17)
C12 0.089(2) 0.0599(19) 0.0566(17) 0.0154(15) -0.0112(16) -0.0125(18)
C13 0.0559(14) 0.0499(16) 0.0470(14) 0.0061(13) 0.0000(12) -0.0062(13)
Cl1 0.0617(4) 0.0484(4) 0.0511(4) -0.0129(3) -0.0070(3) -0.0099(3)

_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 C6 1.531(3) . ?
C1 C2 1.539(3) . ?
C1 C7 1.536(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.542(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.533(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.529(3) . ?
C4 C7 1.535(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.542(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.506(3) . ?
C7 Cl1 1.829(2) . ?
C8 C13 1.384(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 H13 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
C6 C1 C2 107.7(2) . . ?
C6 C1 C7 103.19(17) . . ?
C2 C1 C7 99.90(17) . . ?
C6 C1 H1 114.8 . . ?
C2 C1 H1 114.8 . . ?
C7 C1 H1 114.8 . . ?
C1 C2 C3 103.36(18) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 103.12(17) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 C5 107.9(2) . . ?
C3 C4 C7 100.13(17) . . ?
C5 C4 C7 103.41(17) . . ?
C3 C4 H4 114.6 . . ?
C5 C4 H4 114.6 . . ?
C7 C4 H4 114.6 . . ?
C4 C5 C6 103.29(18) . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5B 111.1 . . ?
C6 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C1 C6 C5 103.30(17) . . ?
C1 C6 H6A 111.1 . . ?
C5 C6 H6A 111.1 . . ?
C1 C6 H6B 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C4 117.62(16) . . ?
C8 C7 C1 117.74(17) . . ?
C4 C7 C1 93.95(17) . . ?
C8 C7 Cl1 105.17(15) . . ?
C4 C7 Cl1 111.29(14) . . ?
C1 C7 Cl1 111.02(13) . . ?
C13 C8 C9 118.0(2) . . ?
C13 C8 C7 120.91(19) . . ?
C9 C8 C7 121.1(2) . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.7(2) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?

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
C6 C1 C2 C3 -71.3(2) . . . . ?
C7 C1 C2 C3 36.1(2) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C2 C3 C4 C5 71.0(2) . . . . ?
C2 C3 C4 C7 -36.8(2) . . . . ?
C3 C4 C5 C6 -71.6(2) . . . . ?
C7 C4 C5 C6 33.9(2) . . . . ?
C2 C1 C6 C5 70.7(2) . . . . ?
C7 C1 C6 C5 -34.4(2) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C3 C4 C7 C8 -66.0(2) . . . . ?
C5 C4 C7 C8 -177.33(19) . . . . ?
C3 C4 C7 C1 58.24(18) . . . . ?
C5 C4 C7 C1 -53.09(19) . . . . ?
C3 C4 C7 Cl1 172.62(15) . . . . ?
C5 C4 C7 Cl1 61.3(2) . . . . ?
C6 C1 C7 C8 177.35(18) . . . . ?
C2 C1 C7 C8 66.4(2) . . . . ?
C6 C1 C7 C4 53.21(19) . . . . ?
C2 C1 C7 C4 -57.76(18) . . . . ?
C6 C1 C7 Cl1 -61.40(19) . . . . ?
C2 C1 C7 Cl1 -172.37(15) . . . . ?
C4 C7 C8 C13 144.6(2) . . . . ?
C1 C7 C8 C13 33.3(3) . . . . ?
Cl1 C7 C8 C13 -90.9(2) . . . . ?
C4 C7 C8 C9 -37.5(3) . . . . ?
C1 C7 C8 C9 -148.8(2) . . . . ?
Cl1 C7 C8 C9 87.0(2) . . . . ?
C13 C8 C9 C10 0.3(4) . . . . ?
C7 C8 C9 C10 -177.7(2) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 0.8(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C9 C8 C13 C12 0.1(4) . . . . ?
C7 C8 C13 C12 178.1(2) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039

#===================================================================END
