# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1412157'
_audit_update_record             
;
2015-07-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 Br2 N5 O2'
_chemical_formula_weight         589.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8674(18)
_cell_length_b                   9.3784(19)
_cell_length_c                   16.618(3)
_cell_angle_alpha                82.99(3)
_cell_angle_beta                 87.24(3)
_cell_angle_gamma                62.65(3)
_cell_volume                     1218.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7716
_cell_measurement_theta_min      6.9
_cell_measurement_theta_max      49.4

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.360
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5814
_exptl_absorpt_correction_T_max  0.7637
_exptl_absorpt_process_details   'face indexed'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7716
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.431
_diffrn_reflns_theta_max         24.598
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.933
_reflns_number_total             4006
_reflns_number_gt                3174
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1128P)²+0.6185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4006
_refine_ls_number_parameters     325
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.018
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1934(8) 0.6972(8) 0.5182(4) 0.0392(13) Uani 1 1 d . . . . .
H1A H 0.2182 0.7370 0.5652 0.059 Uiso 1 1 calc R U . . .
H1B H 0.2347 0.5801 0.5289 0.059 Uiso 1 1 calc R U . . .
H1C H 0.0705 0.7502 0.5085 0.059 Uiso 1 1 calc R U . . .
C2 C 0.2809(7) 0.7346(7) 0.4443(4) 0.0311(12) Uani 1 1 d . . . . .
C3 C 0.3972(7) 0.6138(7) 0.4000(3) 0.0326(12) Uani 1 1 d . . . . .
H3 H 0.4218 0.5048 0.4168 0.039 Uiso 1 1 calc R U . . .
C4 C 0.4775(7) 0.6472(6) 0.3331(3) 0.0307(12) Uani 1 1 d . . . . .
H4 H 0.5560 0.5626 0.3040 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4425(6) 0.8060(6) 0.3085(3) 0.0257(10) Uani 1 1 d . . . . .
C6 C 0.3279(7) 0.9292(6) 0.3523(3) 0.0322(12) Uani 1 1 d . . . . .
H6 H 0.3055 1.0379 0.3364 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2487(8) 0.8927(7) 0.4175(4) 0.0415(14) Uani 1 1 d . . . . .
H7 H 0.1686 0.9779 0.4459 0.050 Uiso 1 1 calc R U . . .
C8 C 0.4524(7) 0.9974(6) 0.1911(4) 0.0318(12) Uani 1 1 d . . . . .
H8 H 0.3504 1.0904 0.2011 0.038 Uiso 1 1 calc R U . . .
C9 C 0.5593(7) 0.9854(6) 0.1294(4) 0.0320(12) Uani 1 1 d . . . . .
H9 H 0.5475 1.0687 0.0877 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6620(6) 0.7481(6) 0.2031(3) 0.0256(10) Uani 1 1 d . . . . .
H10 H 0.7317 0.6377 0.2219 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8338(7) 0.7699(6) 0.0855(3) 0.0258(11) Uani 1 1 d . . . . .
C12 C 0.9648(7) 0.6158(6) 0.1010(4) 0.0314(12) Uani 1 1 d . . . . .
H12 H 0.9637 0.5449 0.1468 0.038 Uiso 1 1 calc R U . . .
C13 C 1.0973(7) 0.5694(6) 0.0470(3) 0.0318(12) Uani 1 1 d . . . . .
H13 H 1.1905 0.4643 0.0555 0.038 Uiso 1 1 calc R U . . .
C14 C 1.0962(7) 0.6742(6) -0.0195(3) 0.0303(12) Uani 1 1 d . . . . .
H14 H 1.1862 0.6438 -0.0575 0.036 Uiso 1 1 calc R U . . .
C15 C 0.9578(6) 0.8249(6) -0.0276(3) 0.0248(10) Uani 1 1 d . . . . .
C16 C 0.8082(7) 1.0979(6) -0.1039(3) 0.0290(11) Uani 1 1 d . . . . .
H16 H 0.7115 1.1411 -0.0702 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8398(7) 1.1739(6) -0.1710(3) 0.0294(11) Uani 1 1 d . . . . .
H17 H 0.7691 1.2816 -0.1936 0.035 Uiso 1 1 calc R U . . .
C18 C 1.0540(6) 0.9292(6) -0.1537(3) 0.0255(11) Uani 1 1 d . . . . .
H18 H 1.1572 0.8353 -0.1608 0.031 Uiso 1 1 calc R U . . .
C19 C 1.0739(6) 1.1044(6) -0.2731(3) 0.0264(11) Uani 1 1 d . . . . .
C20 C 1.0213(7) 1.2648(7) -0.3032(3) 0.0330(12) Uani 1 1 d . . . . .
H20 H 0.9343 1.3488 -0.2767 0.040 Uiso 1 1 calc R U . . .
C21 C 1.0961(8) 1.3012(7) -0.3716(3) 0.0336(12) Uani 1 1 d . . . . .
H21 H 1.0610 1.4111 -0.3917 0.040 Uiso 1 1 calc R U . . .
C22 C 1.2227(7) 1.1796(7) -0.4122(3) 0.0313(12) Uani 1 1 d . . . . .
C23 C 1.2743(8) 1.0204(7) -0.3793(4) 0.0363(13) Uani 1 1 d . . . . .
H23 H 1.3633 0.9360 -0.4047 0.044 Uiso 1 1 calc R U . . .
C24 C 1.2003(7) 0.9812(6) -0.3111(3) 0.0320(12) Uani 1 1 d . . . . .
H24 H 1.2356 0.8714 -0.2905 0.038 Uiso 1 1 calc R U . . .
C25 C 1.3010(8) 1.2212(8) -0.4878(4) 0.0405(14) Uani 1 1 d . . . . .
H25A H 1.3801 1.2604 -0.4733 0.061 Uiso 1 1 calc R U . . .
H25B H 1.2115 1.3056 -0.5234 0.061 Uiso 1 1 calc R U . . .
H25C H 1.3624 1.1248 -0.5160 0.061 Uiso 1 1 calc R U . . .
N1 N 0.5193(6) 0.8476(5) 0.2375(3) 0.0272(9) Uani 1 1 d . . . . .
N2 N 0.6900(5) 0.8294(5) 0.1380(3) 0.0252(9) Uani 1 1 d . . . . .
N3 N 0.8282(5) 0.8748(5) 0.0226(3) 0.0254(9) Uani 1 1 d . . . . .
N4 N 0.9437(5) 0.9440(5) -0.0929(3) 0.0249(9) Uani 1 1 d . . . . .
N5 N 0.9944(5) 1.0678(5) -0.2020(3) 0.0254(9) Uani 1 1 d . . . . .
Br1 Br 0.47732(7) 0.57839(7) 0.84504(4) 0.0392(2) Uani 1 1 d . . . . .
Br2 Br 0.98791(7) 0.32077(6) 0.26339(4) 0.0375(2) Uani 1 1 d . . . . .
O1 O 0.4685(6) 0.2995(5) 0.9863(3) 0.0427(10) Uani 1 1 d D . . . .
O2 O 0.6557(8) 0.6808(8) 0.6781(4) 0.0669(15) Uani 1 1 d D . . . .
H2O H 0.487(8) 0.345(7) 1.026(3) 0.035(17) Uiso 1 1 d D . . . .
H1O H 0.472(9) 0.364(7) 0.944(3) 0.042(19) Uiso 1 1 d D . . . .
H1P H 0.758(8) 0.644(13) 0.700(7) 0.10(4) Uiso 1 1 d D . . . .
H2P H 0.620(10) 0.648(10) 0.724(3) 0.07(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.512(8) . ?
C2 C7 1.393(8) . ?
C2 C3 1.395(8) . ?
C3 C4 1.374(8) . ?
C4 C5 1.386(7) . ?
C5 C6 1.397(7) . ?
C5 N1 1.435(7) . ?
C6 C7 1.358(8) . ?
C8 C9 1.341(8) . ?
C8 N1 1.391(7) . ?
C9 N2 1.383(7) . ?
C10 N2 1.327(7) . ?
C10 N1 1.332(7) . ?
C11 N3 1.331(7) . ?
C11 C12 1.378(8) . ?
C11 N2 1.434(6) . ?
C12 C13 1.379(8) . ?
C13 C14 1.383(8) . ?
C14 C15 1.378(7) . ?
C15 N3 1.321(7) . ?
C15 N4 1.424(7) . ?
C16 C17 1.339(8) . ?
C16 N4 1.387(7) . ?
C17 N5 1.392(7) . ?
C18 N5 1.330(7) . ?
C18 N4 1.345(7) . ?
C19 C24 1.383(7) . ?
C19 C20 1.387(7) . ?
C19 N5 1.433(7) . ?
C20 C21 1.375(8) . ?
C21 C22 1.398(8) . ?
C22 C23 1.391(8) . ?
C22 C25 1.502(8) . ?
C23 C24 1.378(8) . ?

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 C2 C3 116.9(5) . . ?
C7 C2 C1 121.0(5) . . ?
C3 C2 C1 122.1(5) . . ?
C4 C3 C2 122.2(5) . . ?
C3 C4 C5 119.2(5) . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 N1 121.2(5) . . ?
C6 C5 N1 119.0(5) . . ?
C7 C6 C5 119.7(5) . . ?
C6 C7 C2 122.2(5) . . ?
C9 C8 N1 106.9(5) . . ?
C8 C9 N2 107.3(5) . . ?
N2 C10 N1 108.3(4) . . ?
N3 C11 C12 124.4(5) . . ?
N3 C11 N2 114.6(5) . . ?
C12 C11 N2 121.1(5) . . ?
C11 C12 C13 116.8(5) . . ?
C12 C13 C14 120.7(5) . . ?
C15 C14 C13 116.5(5) . . ?
N3 C15 C14 125.0(5) . . ?
N3 C15 N4 113.4(4) . . ?
C14 C15 N4 121.6(5) . . ?
C17 C16 N4 106.9(5) . . ?
C16 C17 N5 108.1(5) . . ?
N5 C18 N4 108.7(4) . . ?
C24 C19 C20 120.8(5) . . ?
C24 C19 N5 120.2(4) . . ?
C20 C19 N5 119.0(5) . . ?
C21 C20 C19 119.4(5) . . ?
C20 C21 C22 121.3(5) . . ?
C23 C22 C21 117.5(5) . . ?
C23 C22 C25 121.8(5) . . ?
C21 C22 C25 120.7(5) . . ?
C24 C23 C22 122.1(5) . . ?
C23 C24 C19 118.8(5) . . ?
C10 N1 C8 108.6(4) . . ?
C10 N1 C5 126.0(5) . . ?
C8 N1 C5 125.4(5) . . ?
C10 N2 C9 108.9(4) . . ?
C10 N2 C11 126.6(4) . . ?
C9 N2 C11 124.5(4) . . ?
C15 N3 C11 116.7(4) . . ?
C18 N4 C16 108.4(4) . . ?
C18 N4 C15 127.4(4) . . ?
C16 N4 C15 124.2(4) . . ?
C18 N5 C17 107.9(4) . . ?
C18 N5 C19 126.8(4) . . ?
C17 N5 C19 125.3(4) . . ?

_refine_diff_density_max         1.132
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.132

_shelxl_version_number           2013-3


####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1412158'
_audit_update_record             
;
2015-07-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 O2'
_chemical_formula_weight         298.32

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   23.657(5)
_cell_length_b                   7.2556(15)
_cell_length_c                   18.859(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.31(3)
_cell_angle_gamma                90
_cell_volume                     3015.8(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    12657
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      52.5

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_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      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11988
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.296
_diffrn_reflns_theta_max         26.215
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2990
_reflns_number_gt                1913
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0798P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2990
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_restrained_S_all      0.929
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.29258(9) 0.4970(2) 0.64192(10) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.27196(9) 0.5548(3) 0.56417(11) 0.0313(4) Uani 1 1 d . . . . .
H2 H 0.2938 0.6474 0.5493 0.038 Uiso 1 1 calc R U . . .
C3 C 0.22153(10) 0.4792(3) 0.51109(12) 0.0366(5) Uani 1 1 d . . . . .
H3 H 0.2088 0.5196 0.4597 0.044 Uiso 1 1 calc R U . . .
C4 C 0.18811(10) 0.3419(3) 0.53147(13) 0.0395(5) Uani 1 1 d . . . . .
H4 H 0.1528 0.2916 0.4939 0.047 Uiso 1 1 calc R U . . .
C5 C 0.20596(9) 0.2815(3) 0.60403(12) 0.0353(5) Uani 1 1 d . . . . .
H5 H 0.1831 0.1885 0.6169 0.042 Uiso 1 1 calc R U . . .
C6 C 0.25856(9) 0.3550(3) 0.66163(11) 0.0298(4) Uani 1 1 d . . . . .
C7 C 0.27710(9) 0.2941(3) 0.73684(11) 0.0302(4) Uani 1 1 d . . . . .
H7 H 0.2544 0.2006 0.7497 0.036 Uiso 1 1 calc R U . . .
C8 C 0.32791(9) 0.3667(2) 0.79330(11) 0.0286(4) Uani 1 1 d . . . . .
C9 C 0.34679(10) 0.3051(3) 0.87051(11) 0.0336(5) Uani 1 1 d . . . . .
H9 H 0.3245 0.2109 0.8837 0.040 Uiso 1 1 calc R U . . .
C10 C 0.39597(10) 0.3794(3) 0.92504(12) 0.0373(5) Uani 1 1 d . . . . .
H10 H 0.4075 0.3381 0.9762 0.045 Uiso 1 1 calc R U . . .
C11 C 0.43038(10) 0.5182(3) 0.90650(12) 0.0371(5) Uani 1 1 d . . . . .
H11 H 0.4651 0.5683 0.9452 0.045 Uiso 1 1 calc R U . . .
C12 C 0.41420(9) 0.5801(3) 0.83388(11) 0.0322(5) Uani 1 1 d . . . . .
H12 H 0.4381 0.6724 0.8225 0.039 Uiso 1 1 calc R U . . .
C13 C 0.36225(8) 0.5100(2) 0.77446(10) 0.0261(4) Uani 1 1 d . . . . .
C14 C 0.34352(9) 0.5754(2) 0.69884(11) 0.0263(4) Uani 1 1 d . . . . .
C15 C 0.37560(9) 0.7365(3) 0.68104(10) 0.0263(4) Uani 1 1 d . . . . .
C16 C 0.36626(10) 0.9103(3) 0.70531(12) 0.0328(5) Uani 1 1 d . . . . .
H16 H 0.3399 0.9226 0.7328 0.039 Uiso 1 1 calc R U . . .
C17 C 0.39430(10) 1.0685(3) 0.69074(12) 0.0367(5) Uani 1 1 d . . . . .
H17 H 0.3875 1.1871 0.7075 0.044 Uiso 1 1 calc R U . . .
C18 C 0.43189(9) 1.0427(3) 0.65117(11) 0.0315(4) Uani 1 1 d . . . . .
C19 C 0.44166(9) 0.8707(3) 0.62650(10) 0.0294(4) Uani 1 1 d . . . . .
C20 C 0.41475(9) 0.7146(3) 0.64075(11) 0.0294(4) Uani 1 1 d . . . . .
H20 H 0.4223 0.5967 0.6241 0.035 Uiso 1 1 calc R U . . .
C21 C 0.50062(12) 1.0732(3) 0.59724(14) 0.0471(6) Uani 1 1 d . . . . .
H21A H 0.5432 1.0763 0.6334 0.056 Uiso 1 1 calc R U . . .
H21B H 0.4991 1.1281 0.5485 0.056 Uiso 1 1 calc R U . . .
O1 O 0.46284(7) 1.1742(2) 0.62706(9) 0.0424(4) Uani 1 1 d . . . . .
O2 O 0.47918(7) 0.8872(2) 0.58536(9) 0.0394(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.410(3) . ?
C1 C2 1.430(3) . ?
C1 C6 1.437(3) . ?
C2 C3 1.363(3) . ?
C3 C4 1.409(3) . ?
C4 C5 1.350(3) . ?
C5 C6 1.425(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.431(3) . ?
C8 C13 1.441(3) . ?
C9 C10 1.353(3) . ?
C10 C11 1.416(3) . ?
C11 C12 1.358(3) . ?
C12 C13 1.423(3) . ?
C13 C14 1.413(3) . ?
C14 C15 1.497(3) . ?
C15 C16 1.386(3) . ?
C15 C20 1.404(3) . ?
C16 C17 1.403(3) . ?
C17 C18 1.365(3) . ?
C18 O1 1.377(2) . ?
C18 C19 1.381(3) . ?
C19 C20 1.373(3) . ?
C19 O2 1.380(2) . ?
C21 O1 1.421(3) . ?
C21 O2 1.430(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
C14 C1 C2 122.78(17) . . ?
C14 C1 C6 119.75(17) . . ?
C2 C1 C6 117.46(17) . . ?
C3 C2 C1 121.10(19) . . ?
C2 C3 C4 120.80(19) . . ?
C5 C4 C3 120.4(2) . . ?
C4 C5 C6 121.07(19) . . ?
C7 C6 C5 121.41(18) . . ?
C7 C6 C1 119.43(18) . . ?
C5 C6 C1 119.16(18) . . ?
C8 C7 C6 121.62(18) . . ?
C7 C8 C9 121.71(18) . . ?
C7 C8 C13 119.56(17) . . ?
C9 C8 C13 118.72(18) . . ?
C10 C9 C8 120.89(19) . . ?
C9 C10 C11 120.53(19) . . ?
C12 C11 C10 120.5(2) . . ?
C11 C12 C13 121.5(2) . . ?
C14 C13 C12 122.62(17) . . ?
C14 C13 C8 119.54(17) . . ?
C12 C13 C8 117.84(16) . . ?
C1 C14 C13 120.06(17) . . ?
C1 C14 C15 120.45(16) . . ?
C13 C14 C15 119.36(17) . . ?
C16 C15 C20 119.83(17) . . ?
C16 C15 C14 118.79(17) . . ?
C20 C15 C14 121.38(16) . . ?
C15 C16 C17 122.44(18) . . ?
C18 C17 C16 116.30(18) . . ?
C17 C18 O1 127.98(18) . . ?
C17 C18 C19 122.02(18) . . ?
O1 C18 C19 109.94(17) . . ?
C20 C19 C18 122.24(17) . . ?
C20 C19 O2 128.35(17) . . ?
C18 C19 O2 109.36(16) . . ?
C19 C20 C15 117.15(17) . . ?
O1 C21 O2 108.10(17) . . ?
C18 O1 C21 105.04(16) . . ?
C19 O2 C21 104.94(16) . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-3



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1412159'
_audit_update_record             
;
2015-07-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18'
_chemical_formula_weight         330.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   10.441(2)
_cell_length_b                   7.4965(15)
_cell_length_c                   22.577(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.06(3)
_cell_angle_gamma                90
_cell_volume                     1762.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    14996
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      53.8

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9900
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_process_details   'face indexed'

_exptl_special_details           
;
programs X-Red32 and X-Shape by STOE & Cie GmbH 2010
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14359
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.809
_diffrn_reflns_theta_max         26.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3740
_reflns_number_gt                2409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²+0.0816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3740
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.17254(16) 0.7076(2) 0.64257(7) 0.0369(4) Uani 1 1 d . . . . .
C2 C 0.05864(17) 0.6513(2) 0.60893(8) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.0628 0.5554 0.5816 0.051 Uiso 1 1 calc R U . . .
C3 C -0.05540(17) 0.7330(3) 0.61553(9) 0.0469(4) Uani 1 1 d . . . . .
H3 H -0.1298 0.6941 0.5925 0.056 Uiso 1 1 calc R U . . .
C4 C -0.06544(18) 0.8754(3) 0.65628(9) 0.0492(5) Uani 1 1 d . . . . .
H4 H -0.1461 0.9308 0.6604 0.059 Uiso 1 1 calc R U . . .
C5 C 0.03966(17) 0.9322(2) 0.68918(8) 0.0449(4) Uani 1 1 d . . . . .
H5 H 0.0317 1.0269 0.7167 0.054 Uiso 1 1 calc R U . . .
C6 C 0.16283(17) 0.8528(2) 0.68355(8) 0.0395(4) Uani 1 1 d . . . . .
C7 C 0.27285(17) 0.9162(2) 0.71506(7) 0.0411(4) Uani 1 1 d . . . . .
H7 H 0.2658 1.0115 0.7424 0.049 Uiso 1 1 calc R U . . .
C8 C 0.39325(16) 0.8426(2) 0.70730(7) 0.0385(4) Uani 1 1 d . . . . .
C9 C 0.50677(18) 0.9088(3) 0.73898(8) 0.0469(4) Uani 1 1 d . . . . .
H9 H 0.5008 1.0057 0.7658 0.056 Uiso 1 1 calc R U . . .
C10 C 0.62292(18) 0.8349(3) 0.73128(8) 0.0486(5) Uani 1 1 d . . . . .
H10 H 0.6976 0.8812 0.7523 0.058 Uiso 1 1 calc R U . . .
C11 C 0.63352(17) 0.6892(3) 0.69210(8) 0.0449(4) Uani 1 1 d . . . . .
H11 H 0.7155 0.6384 0.6872 0.054 Uiso 1 1 calc R U . . .
C12 C 0.52834(16) 0.6211(2) 0.66136(8) 0.0405(4) Uani 1 1 d . . . . .
H12 H 0.5376 0.5223 0.6356 0.049 Uiso 1 1 calc R U . . .
C13 C 0.40376(16) 0.6957(2) 0.66707(7) 0.0365(4) Uani 1 1 d . . . . .
C14 C 0.29319(16) 0.6281(2) 0.63562(7) 0.0366(4) Uani 1 1 d . . . . .
C15 C 0.30000(15) 0.4703(2) 0.59565(7) 0.0374(4) Uani 1 1 d . . . . .
C16 C 0.2564(2) 0.3050(3) 0.61359(8) 0.0503(5) Uani 1 1 d . . . . .
H16 H 0.2280 0.2920 0.6524 0.060 Uiso 1 1 calc R U . . .
C17 C 0.2536(2) 0.1597(3) 0.57611(8) 0.0500(5) Uani 1 1 d . . . . .
H17 H 0.2227 0.0485 0.5894 0.060 Uiso 1 1 calc R U . . .
C18 C 0.29545(16) 0.1732(2) 0.51905(7) 0.0376(4) Uani 1 1 d . . . . .
C19 C 0.34241(15) 0.3372(2) 0.50170(7) 0.0378(4) Uani 1 1 d . . . . .
H19 H 0.3738 0.3491 0.4634 0.045 Uiso 1 1 calc R U . . .
C20 C 0.34434(15) 0.4835(2) 0.53919(7) 0.0378(4) Uani 1 1 d . . . . .
H20 H 0.3764 0.5944 0.5262 0.045 Uiso 1 1 calc R U . . .
C21 C 0.28545(16) 0.0185(2) 0.47787(7) 0.0401(4) Uani 1 1 d . . . . .
C22 C 0.18007(18) -0.0963(2) 0.47773(9) 0.0479(5) Uani 1 1 d . . . . .
H22 H 0.1165 -0.0778 0.5052 0.057 Uiso 1 1 calc R U . . .
C23 C 0.1673(2) -0.2367(3) 0.43800(10) 0.0557(5) Uani 1 1 d . . . . .
H23 H 0.0946 -0.3129 0.4380 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2596(2) -0.2665(3) 0.39847(9) 0.0567(5) Uani 1 1 d . . . . .
H24 H 0.2504 -0.3630 0.3712 0.068 Uiso 1 1 calc R U . . .
C25 C 0.3654(2) -0.1564(3) 0.39847(9) 0.0534(5) Uani 1 1 d . . . . .
H25 H 0.4297 -0.1780 0.3716 0.064 Uiso 1 1 calc R U . . .
C26 C 0.37806(18) -0.0143(3) 0.43769(8) 0.0445(4) Uani 1 1 d . . . . .
H26 H 0.4508 0.0618 0.4372 0.053 Uiso 1 1 calc R U . . .


_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 C14 1.412(2) . ?
C1 C2 1.429(2) . ?
C1 C6 1.436(2) . ?
C2 C3 1.356(3) . ?
C3 C4 1.418(3) . ?
C4 C5 1.350(3) . ?
C5 C6 1.431(2) . ?
C6 C7 1.391(3) . ?
C7 C8 1.395(2) . ?
C8 C9 1.429(3) . ?
C8 C13 1.437(2) . ?
C9 C10 1.355(3) . ?
C10 C11 1.415(3) . ?
C11 C12 1.357(3) . ?
C12 C13 1.430(2) . ?
C13 C14 1.406(2) . ?
C14 C15 1.493(2) . ?
C15 C16 1.390(3) . ?
C15 C20 1.390(2) . ?
C16 C17 1.379(3) . ?
C17 C18 1.393(2) . ?
C18 C19 1.390(2) . ?
C18 C21 1.485(2) . ?
C19 C20 1.385(2) . ?
C21 C26 1.394(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.383(3) . ?
C23 C24 1.377(3) . ?
C24 C25 1.379(3) . ?
C25 C26 1.386(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
C14 C1 C2 122.10(16) . . ?
C14 C1 C6 119.70(16) . . ?
C2 C1 C6 118.18(16) . . ?
C3 C2 C1 120.81(18) . . ?
C2 C3 C4 121.13(18) . . ?
C5 C4 C3 120.01(17) . . ?
C4 C5 C6 121.36(18) . . ?
C7 C6 C5 121.80(16) . . ?
C7 C6 C1 119.66(16) . . ?
C5 C6 C1 118.50(17) . . ?
C6 C7 C8 121.29(16) . . ?
C7 C8 C9 121.52(16) . . ?
C7 C8 C13 119.49(16) . . ?
C9 C8 C13 118.99(16) . . ?
C10 C9 C8 120.79(18) . . ?
C9 C10 C11 120.40(17) . . ?
C12 C11 C10 120.94(17) . . ?
C11 C12 C13 121.01(17) . . ?
C14 C13 C12 122.22(16) . . ?
C14 C13 C8 119.91(15) . . ?
C12 C13 C8 117.87(16) . . ?
C13 C14 C1 119.91(16) . . ?
C13 C14 C15 121.21(15) . . ?
C1 C14 C15 118.87(15) . . ?
C16 C15 C20 117.91(16) . . ?
C16 C15 C14 119.98(15) . . ?
C20 C15 C14 122.05(15) . . ?
C17 C16 C15 121.25(16) . . ?
C16 C17 C18 121.04(18) . . ?
C19 C18 C17 117.71(16) . . ?
C19 C18 C21 121.65(15) . . ?
C17 C18 C21 120.61(16) . . ?
C20 C19 C18 121.23(15) . . ?
C19 C20 C15 120.83(16) . . ?
C26 C21 C22 118.19(17) . . ?
C26 C21 C18 121.59(16) . . ?
C22 C21 C18 120.20(15) . . ?
C23 C22 C21 120.66(18) . . ?
C24 C23 C22 120.29(19) . . ?
C23 C24 C25 120.00(19) . . ?
C24 C25 C26 120.03(19) . . ?
C25 C26 C21 120.82(19) . . ?

_refine_diff_density_max         0.596
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-3



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1412160'
_audit_update_record             
;
2015-07-11 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18'
_chemical_formula_weight         330.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.596(2)
_cell_length_b                   13.501(3)
_cell_length_c                   12.120(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.38(3)
_cell_angle_gamma                90
_cell_volume                     1733.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    10109
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      59.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.454
_exptl_crystal_size_min          0.331
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.977
_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      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9382
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.362
_diffrn_reflns_theta_max         29.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2345
_reflns_number_gt                1988
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²+0.6426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2345
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24000(9) 0.16345(7) 0.56648(7) 0.0191(2) Uani 1 1 d . . . . .
C2 C 0.13305(8) 0.22311(7) 0.54716(7) 0.0190(2) Uani 1 1 d . . . . .
C3 C 0.01387(9) 0.20128(8) 0.59644(8) 0.0239(2) Uani 1 1 d . . . . .
H1 H 0.0061 0.1443 0.6419 0.029 Uiso 1 1 calc R U . . .
C4 C -0.08821(10) 0.26023(8) 0.57965(9) 0.0285(2) Uani 1 1 d . . . . .
H7 H -0.1664 0.2443 0.6132 0.034 Uiso 1 1 calc R U . . .
C5 C -0.07851(10) 0.34545(8) 0.51222(9) 0.0286(2) Uani 1 1 d . . . . .
H6 H -0.1506 0.3861 0.5004 0.034 Uiso 1 1 calc R U . . .
C6 C 0.03282(9) 0.36977(7) 0.46418(8) 0.0237(2) Uani 1 1 d . . . . .
H5 H 0.0375 0.4274 0.4195 0.028 Uiso 1 1 calc R U . . .
C7 C 0.14320(8) 0.31012(7) 0.47968(7) 0.0189(2) Uani 1 1 d . . . . .
C8 C 0.22742(9) 0.07240(7) 0.63494(8) 0.0207(2) Uani 1 1 d . . . . .
C9 C 0.15408(9) -0.00667(7) 0.59850(8) 0.0232(2) Uani 1 1 d . . . . .
H9 H 0.1132 -0.0030 0.5286 0.028 Uiso 1 1 calc R U . . .
C10 C 0.13988(10) -0.09100(8) 0.66303(9) 0.0280(2) Uani 1 1 d . . . . .
H10 H 0.0883 -0.1440 0.6378 0.034 Uiso 1 1 calc R U . . .
C11 C 0.20072(11) -0.09769(8) 0.76390(10) 0.0320(3) Uani 1 1 d . . . . .
H11 H 0.1915 -0.1554 0.8080 0.038 Uiso 1 1 calc R U . . .
C12 C 0.27493(12) -0.02018(9) 0.80042(9) 0.0339(3) Uani 1 1 d . . . . .
H12 H 0.3174 -0.0249 0.8695 0.041 Uiso 1 1 calc R U . . .
C13 C 0.28800(11) 0.06470(8) 0.73687(9) 0.0277(2) Uani 1 1 d . . . . .
H13 H 0.3386 0.1179 0.7631 0.033 Uiso 1 1 calc R U . . .


_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 1.4076(13) 7_556 ?
C1 C2 1.4086(13) . ?
C1 C8 1.4895(13) . ?
C2 C3 1.4312(14) . ?
C2 C7 1.4358(13) . ?
C3 C4 1.3571(14) . ?
C4 C5 1.4154(15) . ?
C5 C6 1.3592(15) . ?
C6 C7 1.4313(13) . ?
C7 C1 1.4076(13) 7_556 ?
C8 C9 1.3906(14) . ?
C8 C13 1.3923(14) . ?
C9 C10 1.3900(14) . ?
C10 C11 1.3812(17) . ?
C11 C12 1.3801(17) . ?
C12 C13 1.3882(15) . ?

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 119.83(8) 7_556 . ?
C7 C1 C8 120.85(8) 7_556 . ?
C2 C1 C8 119.31(8) . . ?
C1 C2 C3 121.60(9) . . ?
C1 C2 C7 119.95(8) . . ?
C3 C2 C7 118.42(8) . . ?
C4 C3 C2 121.41(9) . . ?
C3 C4 C5 120.16(10) . . ?
C6 C5 C4 120.68(9) . . ?
C5 C6 C7 121.24(9) . . ?
C1 C7 C6 121.67(9) 7_556 . ?
C1 C7 C2 120.21(8) 7_556 . ?
C6 C7 C2 118.09(9) . . ?
C9 C8 C13 118.54(9) . . ?
C9 C8 C1 120.56(9) . . ?
C13 C8 C1 120.89(9) . . ?
C10 C9 C8 120.83(9) . . ?
C11 C10 C9 120.00(10) . . ?
C12 C11 C10 119.73(10) . . ?
C11 C12 C13 120.45(10) . . ?
C12 C13 C8 120.45(10) . . ?

_refine_diff_density_max         0.342
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-3



