# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 2294551'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Rennes university
France
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_date             2023-06-06T15:38:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C52 H39 N, 0.471(C H Cl3) [+ solvent]'
_chemical_formula_sum            'C52.47 H39.47 Cl1.41 N [+ solvent]'
_chemical_formula_weight         734.06
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_Int_Tables_number      29
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   38.622(5)
_cell_length_b                   13.2653(15)
_cell_length_c                   8.4911(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4350.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1541.3

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_T_max  0.999

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6511  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.8733                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      0.095043
_diffrn_orient_matrix_ub_12      0.044028
_diffrn_orient_matrix_ub_13      -0.002259
_diffrn_orient_matrix_ub_21      0.019274
_diffrn_orient_matrix_ub_22      -0.027377
_diffrn_orient_matrix_ub_23      -0.023749
_diffrn_orient_matrix_ub_31      -0.066823
_diffrn_orient_matrix_ub_32      0.054725
_diffrn_orient_matrix_ub_33      -0.010063
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_number            77156
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_coverage         0.868
_reflns_number_total             9916
_reflns_number_gt                8733
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1264P)²+4.0501P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9916
_refine_ls_number_parameters     522
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2261
_refine_ls_wR_factor_gt          0.2176
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 3397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_diff_density_max         1.274
_refine_diff_density_min         -1.099
_refine_diff_density_rms         0.076

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.35325(11) 0.0443(3) 0.6663(5) 0.0287(9) Uani 1 1 d . . . . .
C2 C 0.36116(12) 0.0394(3) 0.5047(6) 0.0294(9) Uani 1 1 d . . . . .
C3 C 0.39321(13) -0.0009(4) 0.4585(6) 0.0326(10) Uani 1 1 d . . . . .
H3 H 0.398003 -0.012927 0.35035 0.039 Uiso 1 1 calc R U . . .
C4 C 0.41764(13) -0.0227(4) 0.5719(6) 0.0340(10) Uani 1 1 d . . . . .
H4 H 0.439491 -0.04871 0.540411 0.041 Uiso 1 1 calc R U . . .
C5 C 0.41090(12) -0.0071(4) 0.7355(6) 0.0304(9) Uani 1 1 d . . . . .
C6 C 0.37750(12) 0.0210(3) 0.7819(5) 0.0291(9) Uani 1 1 d . . . . .
H6 H 0.371495 0.024017 0.890306 0.035 Uiso 1 1 calc R U . . .
C7 C 0.31253(12) 0.1359(4) 0.5415(5) 0.0297(9) Uani 1 1 d . . . . .
C8 C 0.33493(12) 0.0984(4) 0.4244(5) 0.0326(10) Uani 1 1 d . . . . .
C9 C 0.33278(13) 0.1393(4) 0.2712(5) 0.0350(10) Uani 1 1 d . . . . .
H9 H 0.345401 0.110005 0.186847 0.042 Uiso 1 1 calc R U . . .
C10 C 0.31195(13) 0.2229(4) 0.2458(6) 0.0374(11) Uani 1 1 d . . . . .
H10 H 0.310891 0.251998 0.143699 0.045 Uiso 1 1 calc R U . . .
C11 C 0.29225(13) 0.2656(4) 0.3697(6) 0.0371(11) Uani 1 1 d . . . . .
C12 C 0.29084(12) 0.2186(4) 0.5144(6) 0.0350(10) Uani 1 1 d . . . . .
H12 H 0.275489 0.241879 0.593957 0.042 Uiso 1 1 calc R U . . .
C13 C 0.43900(12) 0.0073(4) 0.8513(6) 0.0309(9) Uani 1 1 d . . . . .
C14 C 0.46799(12) 0.0641(4) 0.8099(6) 0.0340(10) Uani 1 1 d . . . . .
H14 H 0.474091 0.070528 0.701955 0.041 Uiso 1 1 calc R U . . .
C15 C 0.48815(13) 0.1117(4) 0.9237(6) 0.0366(11) Uani 1 1 d . . . . .
H15 H 0.507347 0.151586 0.892055 0.044 Uiso 1 1 calc R U . . .
C16 C 0.48051(12) 0.1015(4) 1.0845(6) 0.0331(10) Uani 1 1 d . . . . .
C17 C 0.45559(13) 0.0298(4) 1.1250(6) 0.0357(11) Uani 1 1 d . . . . .
H17 H 0.4529 0.011431 1.232426 0.043 Uiso 1 1 calc R U . . .
C18 C 0.43472(12) -0.0150(4) 1.0128(6) 0.0333(10) Uani 1 1 d . . . . .
H18 H 0.417315 -0.061299 1.044613 0.04 Uiso 1 1 calc R U . . .
C19 C 0.49112(12) 0.1811(4) 1.1974(6) 0.0353(11) Uani 1 1 d . . . . .
C20 C 0.51506(12) 0.2563(4) 1.1549(6) 0.0330(10) Uani 1 1 d . . . . .
H20 H 0.532527 0.241096 1.079824 0.04 Uiso 1 1 calc R U . . .
C21 C 0.51379(13) 0.3517(4) 1.2196(6) 0.0382(11) Uani 1 1 d . . . . .
H21 H 0.53 0.40104 1.186027 0.046 Uiso 1 1 calc R U . . .
C22 C 0.48873(13) 0.3777(4) 1.3356(6) 0.0382(11) Uani 1 1 d . . . . .
C23 C 0.47026(15) 0.2958(5) 1.3984(6) 0.0413(12) Uani 1 1 d . . . . .
H23 H 0.456444 0.306204 1.489527 0.05 Uiso 1 1 calc R U . . .
C24 C 0.47146(14) 0.2018(4) 1.3333(6) 0.0377(11) Uani 1 1 d . . . . .
H24 H 0.458677 0.148747 1.38104 0.045 Uiso 1 1 calc R U . . .
C25 C 0.47709(14) 0.4831(4) 1.3510(6) 0.0386(11) Uani 1 1 d . . . . .
C26 C 0.49407(14) 0.5649(4) 1.2775(6) 0.0371(11) Uani 1 1 d . . . . .
H26 H 0.518152 0.559786 1.256124 0.045 Uiso 1 1 calc R U . . .
C27 C 0.47703(13) 0.6510(4) 1.2362(6) 0.0362(11) Uani 1 1 d . . . . .
H27 H 0.48932 0.703832 1.185346 0.043 Uiso 1 1 calc R U . . .
C28 C 0.44137(13) 0.6628(4) 1.2680(6) 0.0350(10) Uani 1 1 d . . . . .
C29 C 0.42625(14) 0.5917(4) 1.3703(7) 0.0418(12) Uani 1 1 d . . . . .
H29 H 0.403863 0.603986 1.412532 0.05 Uiso 1 1 calc R U . . .
C30 C 0.44366(15) 0.5046(4) 1.4098(6) 0.0405(12) Uani 1 1 d . . . . .
H30 H 0.432865 0.457673 1.478485 0.049 Uiso 1 1 calc R U . . .
C31 C 0.41881(13) 0.7252(4) 1.1686(6) 0.0345(10) Uani 1 1 d . . . . .
C32 C 0.42617(14) 0.7302(4) 1.0072(6) 0.0372(11) Uani 1 1 d . . . . .
H32 H 0.449137 0.71758 0.972322 0.045 Uiso 1 1 calc R U . . .
C33 C 0.40118(14) 0.7529(4) 0.8981(6) 0.0375(11) Uani 1 1 d . . . . .
H33 H 0.4072 0.755573 0.789738 0.045 Uiso 1 1 calc R U . . .
C34 C 0.36717(14) 0.7720(4) 0.9431(6) 0.0360(11) Uani 1 1 d . . . . .
C35 C 0.36077(14) 0.7832(4) 1.1058(6) 0.0383(11) Uani 1 1 d . . . . .
H35 H 0.338906 0.807121 1.140827 0.046 Uiso 1 1 calc R U . . .
C36 C 0.38610(14) 0.7594(4) 1.2146(6) 0.0380(11) Uani 1 1 d . . . . .
H36 H 0.381156 0.766611 1.323641 0.046 Uiso 1 1 calc R U . . .
C37 C 0.33892(14) 0.7568(4) 0.8253(6) 0.0387(11) Uani 1 1 d . . . . .
C38 C 0.34303(14) 0.7773(4) 0.6659(7) 0.0384(11) Uani 1 1 d . . . . .
H38 H 0.360263 0.82406 0.633631 0.046 Uiso 1 1 calc R U . . .
C39 C 0.32266(13) 0.7314(4) 0.5534(6) 0.0376(11) Uani 1 1 d . . . . .
H39 H 0.325311 0.749626 0.445872 0.045 Uiso 1 1 calc R U . . .
C40 C 0.29802(13) 0.6579(4) 0.5951(6) 0.0377(11) Uani 1 1 d . . . . .
C41 C 0.29055(14) 0.6495(5) 0.7568(7) 0.0420(12) Uani 1 1 d . . . . .
H41 H 0.271402 0.609902 0.790058 0.05 Uiso 1 1 calc R U . . .
C42 C 0.31054(14) 0.6977(4) 0.8668(6) 0.0414(12) Uani 1 1 d . . . . .
H42 H 0.304843 0.690505 0.975031 0.05 Uiso 1 1 calc R U . . .
C43 C 0.28657(12) 0.5758(4) 0.4877(6) 0.0349(11) Uani 1 1 d . . . . .
C44 C 0.30845(13) 0.5426(4) 0.3669(6) 0.0396(12) Uani 1 1 d . . . . .
H44 H 0.324664 0.588588 0.323096 0.047 Uiso 1 1 calc R U . . .
C45 C 0.30729(14) 0.4445(4) 0.3086(6) 0.0386(11) Uani 1 1 d . . . . .
H45 H 0.322658 0.42406 0.227284 0.046 Uiso 1 1 calc R U . . .
C46 C 0.28306(13) 0.3759(5) 0.3715(6) 0.0388(11) Uani 1 1 d . . . . .
C47 C 0.25738(12) 0.4143(4) 0.4715(6) 0.0388(12) Uani 1 1 d . . . . .
H47 H 0.238446 0.372463 0.50039 0.047 Uiso 1 1 calc R U . . .
C48 C 0.25901(12) 0.5109(4) 0.5285(6) 0.0373(11) Uani 1 1 d . . . . .
H48 H 0.241277 0.534639 0.596565 0.045 Uiso 1 1 calc R U . . .
C491 C 0.30523(13) 0.1163(4) 0.8370(5) 0.0341(10) Uani 0.419(17) 1 d . . P A 1
H49A H 0.300737 0.189438 0.847427 0.041 Uiso 0.419(17) 1 calc R U P A 1
H49B H 0.320373 0.094941 0.924989 0.041 Uiso 0.419(17) 1 calc R U P A 1
C501 C 0.2688(4) 0.0538(12) 0.8422(16) 0.041(4) Uani 0.419(17) 1 d . . P A 1
H50A H 0.255707 0.075254 0.936692 0.049 Uiso 0.419(17) 1 calc R U P A 1
H50B H 0.254909 0.072843 0.748769 0.049 Uiso 0.419(17) 1 calc R U P A 1
C511 C 0.2721(5) -0.0575(12) 0.845(2) 0.055(5) Uani 0.419(17) 1 d . . P A 1
H51A H 0.284536 -0.081163 0.750305 0.066 Uiso 0.419(17) 1 calc R U P A 1
H51B H 0.285435 -0.078714 0.939324 0.066 Uiso 0.419(17) 1 calc R U P A 1
C521 C 0.23720(18) -0.1014(6) 0.8502(11) 0.067(2) Uani 0.419(17) 1 d . . P A 1
H52A H 0.238924 -0.175095 0.852357 0.1 Uiso 0.419(17) 1 calc R U P A 1
H52B H 0.225146 -0.077964 0.944919 0.1 Uiso 0.419(17) 1 calc R U P A 1
H52C H 0.22425 -0.080405 0.75653 0.1 Uiso 0.419(17) 1 calc R U P A 1
C492 C 0.30523(13) 0.1163(4) 0.8370(5) 0.0341(10) Uani 0.581(17) 1 d . . P A 2
H49C H 0.288248 0.171372 0.82228 0.041 Uiso 0.581(17) 1 calc R U P A 2
H49D H 0.322916 0.139959 0.912847 0.041 Uiso 0.581(17) 1 calc R U P A 2
C502 C 0.2870(2) 0.0265(6) 0.9053(10) 0.030(2) Uani 0.581(17) 1 d . . P A 2
H50C H 0.277386 0.043876 1.009853 0.036 Uiso 0.581(17) 1 calc R U P A 2
H50D H 0.303651 -0.029585 0.919044 0.036 Uiso 0.581(17) 1 calc R U P A 2
C512 C 0.2577(3) -0.0063(9) 0.7946(12) 0.039(3) Uani 0.581(17) 1 d . . P A 2
H51C H 0.267646 -0.020261 0.689386 0.047 Uiso 0.581(17) 1 calc R U P A 2
H51D H 0.241234 0.050416 0.783014 0.047 Uiso 0.581(17) 1 calc R U P A 2
C522 C 0.23720(18) -0.1014(6) 0.8502(11) 0.067(2) Uani 0.581(17) 1 d . . P A 2
H52D H 0.21906 -0.117171 0.773363 0.1 Uiso 0.581(17) 1 calc R U P A 2
H52E H 0.253078 -0.158748 0.859156 0.1 Uiso 0.581(17) 1 calc R U P A 2
H52F H 0.226617 -0.08794 0.952958 0.1 Uiso 0.581(17) 1 calc R U P A 2
C53 C 0.3535(3) 0.4065(10) 0.6730(12) 0.041(3) Uani 0.471(5) 1 d . . P . .
H53 H 0.336013 0.416609 0.587713 0.049 Uiso 0.471(5) 1 calc R U P . .
N1 N 0.32202(10) 0.0951(3) 0.6861(5) 0.0307(8) Uani 1 1 d . . . . .
Cl1 Cl 0.37759(11) 0.3093(3) 0.5926(7) 0.0851(12) Uani 0.471(5) 1 d . . P . .
Cl2 Cl 0.37091(11) 0.5129(3) 0.6750(8) 0.0851(12) Uani 0.471(5) 1 d . . P . .
Cl3 Cl 0.32686(11) 0.3959(3) 0.8327(8) 0.0851(12) Uani 0.471(5) 1 d . . P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.391(6) . ?
C1 N1 1.392(6) . ?
C1 C2 1.407(7) . ?
C2 C3 1.404(7) . ?
C2 C8 1.451(7) . ?
C3 C4 1.379(7) . ?
C3 H3 0.95 . ?
C4 C5 1.428(7) . ?
C4 H4 0.95 . ?
C5 C6 1.399(6) . ?
C5 C13 1.478(7) . ?
C6 H6 0.95 . ?
C7 N1 1.391(6) . ?
C7 C12 1.399(7) . ?
C7 C8 1.409(7) . ?
C8 C9 1.412(7) . ?
C9 C10 1.387(8) . ?
C9 H9 0.95 . ?
C10 C11 1.416(7) . ?
C10 H10 0.95 . ?
C11 C12 1.379(7) . ?
C11 C46 1.506(8) . ?
C12 H12 0.95 . ?
C13 C14 1.395(7) . ?
C13 C18 1.412(7) . ?
C14 C15 1.392(7) . ?
C14 H14 0.95 . ?
C15 C16 1.403(7) . ?
C15 H15 0.95 . ?
C16 C17 1.396(7) . ?
C16 C19 1.484(7) . ?
C17 C18 1.383(7) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C19 C20 1.407(7) . ?
C19 C24 1.408(7) . ?
C20 C21 1.380(8) . ?
C20 H20 0.95 . ?
C21 C22 1.423(7) . ?
C21 H21 0.95 . ?
C22 C23 1.405(8) . ?
C22 C25 1.475(8) . ?
C23 C24 1.365(8) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C25 C26 1.413(8) . ?
C25 C30 1.413(8) . ?
C26 C27 1.364(8) . ?
C26 H26 0.95 . ?
C27 C28 1.412(7) . ?
C27 H27 0.95 . ?
C28 C29 1.409(8) . ?
C28 C31 1.469(7) . ?
C29 C30 1.378(8) . ?
C29 H29 0.95 . ?
C30 H30 0.95 . ?
C31 C36 1.398(7) . ?
C31 C32 1.401(7) . ?
C32 C33 1.371(8) . ?
C32 H32 0.95 . ?
C33 C34 1.391(7) . ?
C33 H33 0.95 . ?
C34 C35 1.411(7) . ?
C34 C37 1.494(8) . ?
C35 C36 1.382(8) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?
C37 C38 1.390(8) . ?
C37 C42 1.393(8) . ?
C38 C39 1.379(8) . ?
C38 H38 0.95 . ?
C39 C40 1.408(7) . ?
C39 H39 0.95 . ?
C40 C41 1.407(7) . ?
C40 C43 1.487(8) . ?
C41 C42 1.370(9) . ?
C41 H41 0.95 . ?
C42 H42 0.95 . ?
C43 C44 1.400(8) . ?
C43 C48 1.412(7) . ?
C44 C45 1.392(8) . ?
C44 H44 0.95 . ?
C45 C46 1.410(8) . ?
C45 H45 0.95 . ?
C46 C47 1.401(8) . ?
C47 C48 1.372(8) . ?
C47 H47 0.95 . ?
C48 H48 0.95 . ?
C491 N1 1.463(6) . ?
C491 C501 1.634(16) . ?
C491 H49A 0.99 . ?
C491 H49B 0.99 . ?
C501 C511 1.48(2) . ?
C501 H50A 0.99 . ?
C501 H50B 0.99 . ?
C511 C521 1.469(17) . ?
C511 H51A 0.99 . ?
C511 H51B 0.99 . ?
C521 H52A 0.98 . ?
C521 H52B 0.98 . ?
C521 H52C 0.98 . ?
C492 N1 1.463(6) . ?
C492 C502 1.499(9) . ?
C492 H49C 0.99 . ?
C492 H49D 0.99 . ?
C502 C512 1.535(14) . ?
C502 H50C 0.99 . ?
C502 H50D 0.99 . ?
C512 C522 1.562(12) . ?
C512 H51C 0.99 . ?
C512 H51D 0.99 . ?
C522 H52D 0.98 . ?
C522 H52E 0.98 . ?
C522 H52F 0.98 . ?
C53 Cl2 1.562(13) . ?
C53 Cl3 1.709(12) . ?
C53 Cl1 1.729(13) . ?
C53 H53 1 . ?

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 N1 127.3(4) . . ?
C6 C1 C2 122.1(4) . . ?
N1 C1 C2 109.2(4) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 C8 133.6(4) . . ?
C1 C2 C8 106.4(4) . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.6(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.7(4) . . ?
C6 C5 C13 117.1(4) . . ?
C4 C5 C13 122.2(4) . . ?
C1 C6 C5 118.7(4) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C12 127.4(4) . . ?
N1 C7 C8 108.9(4) . . ?
C12 C7 C8 121.9(4) . . ?
C7 C8 C9 118.6(5) . . ?
C7 C8 C2 106.7(4) . . ?
C9 C8 C2 133.0(5) . . ?
C10 C9 C8 119.0(5) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.0(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.2(5) . . ?
C12 C11 C46 114.9(5) . . ?
C10 C11 C46 121.5(5) . . ?
C11 C12 C7 118.5(5) . . ?
C11 C12 H12 120.8 . . ?
C7 C12 H12 120.8 . . ?
C14 C13 C18 116.9(5) . . ?
C14 C13 C5 119.4(4) . . ?
C18 C13 C5 122.2(4) . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 116.8(5) . . ?
C17 C16 C19 121.0(5) . . ?
C15 C16 C19 120.1(5) . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 120.7(5) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C20 C19 C24 115.2(5) . . ?
C20 C19 C16 121.4(5) . . ?
C24 C19 C16 121.3(5) . . ?
C21 C20 C19 121.6(5) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 121.5(5) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C23 C22 C21 114.9(5) . . ?
C23 C22 C25 123.0(5) . . ?
C21 C22 C25 119.9(5) . . ?
C24 C23 C22 122.4(5) . . ?
C24 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C23 C24 C19 121.9(5) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?
C26 C25 C30 115.2(5) . . ?
C26 C25 C22 123.2(5) . . ?
C30 C25 C22 120.1(5) . . ?
C27 C26 C25 122.2(5) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C26 C27 C28 120.9(5) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 116.6(5) . . ?
C29 C28 C31 119.1(4) . . ?
C27 C28 C31 122.1(5) . . ?
C30 C29 C28 120.6(5) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C25 121.9(5) . . ?
C29 C30 H30 119 . . ?
C25 C30 H30 119 . . ?
C36 C31 C32 116.2(5) . . ?
C36 C31 C28 124.0(5) . . ?
C32 C31 C28 117.9(5) . . ?
C33 C32 C31 121.9(5) . . ?
C33 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?
C32 C33 C34 121.3(5) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C35 116.9(5) . . ?
C33 C34 C37 118.7(5) . . ?
C35 C34 C37 122.8(5) . . ?
C36 C35 C34 120.5(5) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 121.8(5) . . ?
C35 C36 H36 119.1 . . ?
C31 C36 H36 119.1 . . ?
C38 C37 C42 116.5(5) . . ?
C38 C37 C34 122.8(5) . . ?
C42 C37 C34 118.8(5) . . ?
C39 C38 C37 121.5(5) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C38 C39 C40 121.2(5) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C41 C40 C39 116.0(5) . . ?
C41 C40 C43 118.6(5) . . ?
C39 C40 C43 123.6(5) . . ?
C42 C41 C40 120.9(5) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C37 122.3(5) . . ?
C41 C42 H42 118.9 . . ?
C37 C42 H42 118.9 . . ?
C44 C43 C48 116.3(5) . . ?
C44 C43 C40 120.0(4) . . ?
C48 C43 C40 121.3(5) . . ?
C45 C44 C43 122.3(5) . . ?
C45 C44 H44 118.8 . . ?
C43 C44 H44 118.8 . . ?
C44 C45 C46 119.3(5) . . ?
C44 C45 H45 120.3 . . ?
C46 C45 H45 120.3 . . ?
C47 C46 C45 117.7(5) . . ?
C47 C46 C11 121.7(5) . . ?
C45 C46 C11 117.9(5) . . ?
C48 C47 C46 121.4(5) . . ?
C48 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
C47 C48 C43 121.2(5) . . ?
C47 C48 H48 119.4 . . ?
C43 C48 H48 119.4 . . ?
N1 C491 C501 107.9(6) . . ?
N1 C491 H49A 110.1 . . ?
C501 C491 H49A 110.1 . . ?
N1 C491 H49B 110.1 . . ?
C501 C491 H49B 110.1 . . ?
H49A C491 H49B 108.4 . . ?
C511 C501 C491 115.5(11) . . ?
C511 C501 H50A 108.4 . . ?
C491 C501 H50A 108.4 . . ?
C511 C501 H50B 108.4 . . ?
C491 C501 H50B 108.4 . . ?
H50A C501 H50B 107.5 . . ?
C521 C511 C501 108.4(14) . . ?
C521 C511 H51A 110 . . ?
C501 C511 H51A 110 . . ?
C521 C511 H51B 110 . . ?
C501 C511 H51B 110 . . ?
H51A C511 H51B 108.4 . . ?
C511 C521 H52A 109.5 . . ?
C511 C521 H52B 109.5 . . ?
H52A C521 H52B 109.5 . . ?
C511 C521 H52C 109.5 . . ?
H52A C521 H52C 109.5 . . ?
H52B C521 H52C 109.5 . . ?
N1 C492 C502 113.2(5) . . ?
N1 C492 H49C 108.9 . . ?
C502 C492 H49C 108.9 . . ?
N1 C492 H49D 108.9 . . ?
C502 C492 H49D 108.9 . . ?
H49C C492 H49D 107.8 . . ?
C492 C502 C512 109.6(7) . . ?
C492 C502 H50C 109.8 . . ?
C512 C502 H50C 109.8 . . ?
C492 C502 H50D 109.8 . . ?
C512 C502 H50D 109.8 . . ?
H50C C502 H50D 108.2 . . ?
C502 C512 C522 114.7(8) . . ?
C502 C512 H51C 108.6 . . ?
C522 C512 H51C 108.6 . . ?
C502 C512 H51D 108.6 . . ?
C522 C512 H51D 108.6 . . ?
H51C C512 H51D 107.6 . . ?
C512 C522 H52D 109.5 . . ?
C512 C522 H52E 109.5 . . ?
H52D C522 H52E 109.5 . . ?
C512 C522 H52F 109.5 . . ?
H52D C522 H52F 109.5 . . ?
H52E C522 H52F 109.5 . . ?
Cl2 C53 Cl3 108.9(8) . . ?
Cl2 C53 Cl1 116.5(7) . . ?
Cl3 C53 Cl1 125.1(7) . . ?
Cl2 C53 H53 100.2 . . ?
Cl3 C53 H53 100.2 . . ?
Cl1 C53 H53 100.2 . . ?
C7 N1 C1 108.1(4) . . ?
C7 N1 C492 125.6(4) . . ?
C1 N1 C492 125.6(4) . . ?
C7 N1 C491 125.6(4) . . ?
C1 N1 C491 125.6(4) . . ?





####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2294552'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;Rennes university
France
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-11-22 downloaded from the CCDC.
;

_audit_creation_date             2023-06-07T14:54:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#


_chemical_formula_moiety         'C49 H30 O'
_chemical_formula_sum            'C49 H30 O'
_chemical_formula_weight         634.73

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8766(13)
_cell_length_b                   14.9692(16)
_cell_length_c                   10.3986(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.590(4)
_cell_angle_gamma                90
_cell_volume                     1930.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9512
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_T_max  0.997

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.4943  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.6630                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      -0.030881
_diffrn_orient_matrix_ub_12      -0.026266
_diffrn_orient_matrix_ub_13      -0.073946
_diffrn_orient_matrix_ub_21      -0.01749
_diffrn_orient_matrix_ub_22      0.061359
_diffrn_orient_matrix_ub_23      -0.031327
_diffrn_orient_matrix_ub_31      0.093319
_diffrn_orient_matrix_ub_32      0.002808
_diffrn_orient_matrix_ub_33      -0.007159
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_number            33915
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.132
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_reflns_Friedel_coverage         0
_reflns_number_total             4364
_reflns_number_gt                3361
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0942P)²+1.6887P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4364
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.2604
_refine_ls_wR_factor_gt          0.2448
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O1A O 0.7743(3) 0.4411(3) 0.2868(4) 0.0509(10) Uani 0.5 1 d . . P A 1
C1A C 0.8034(4) 0.5100(4) 0.3439(5) 0.0387(11) Uani 0.5 1 d . . P A 1
C2A C 0.7816(5) 0.6024(4) 0.2938(6) 0.0409(12) Uani 0.5 1 d . . P A 1
C3A C 0.7002(5) 0.6282(4) 0.1836(6) 0.0433(13) Uani 0.5 1 d . . P A 1
H3A H 0.666086 0.584826 0.119418 0.052 Uiso 0.5 1 calc R U P A 1
C4A C 0.6670(2) 0.7197(2) 0.1653(3) 0.0502(7) Uani 0.5 1 d . . P A 1
C5A C 0.7301(10) 0.7777(10) 0.2609(16) 0.049(3) Uani 0.5 1 d . . P A 1
H5A H 0.715191 0.839745 0.24896 0.059 Uiso 0.5 1 calc R U P A 1
C6A C 0.8112(7) 0.7530(6) 0.3700(10) 0.0429(19) Uani 0.5 1 d . . P A 1
H6A H 0.849598 0.794478 0.434595 0.051 Uiso 0.5 1 calc R U P A 1
C7A C 0.8333(2) 0.6562(2) 0.3778(3) 0.0542(8) Uani 0.5 1 d . . P A 1
C8A C 0.8852(2) 0.6016(2) 0.4966(4) 0.0630(10) Uani 0.5 1 d . . P A 1
C9A C 0.9310(3) 0.6313(2) 0.6266(4) 0.0662(10) Uani 0.5 1 d . . P A 1
H9A H 0.95142 0.692135 0.64251 0.079 Uiso 0.5 1 calc R U P A 1
C10A C 0.9466(2) 0.5722(2) 0.7321(4) 0.0576(8) Uani 0.5 1 d . . P A 1
H10A H 0.977561 0.593566 0.82012 0.069 Uiso 0.5 1 calc R U P A 1
C11A C 0.9181(2) 0.4820(2) 0.7136(3) 0.0498(7) Uani 0.5 1 d . . P A 1
C12A C 0.8827(2) 0.4520(2) 0.5818(3) 0.0500(7) Uani 0.5 1 d . . P A 1
H12A H 0.869135 0.390267 0.564007 0.06 Uiso 0.5 1 calc R U P A 1
C13A C 0.8675(2) 0.5111(3) 0.4785(3) 0.0607(9) Uani 0.5 1 d . . P A 1
C2B C 0.8115(5) 0.6174(4) 0.2320(7) 0.0485(13) Uani 0.5 1 d . . P A 2
H2B H 0.854698 0.570629 0.212446 0.058 Uiso 0.5 1 calc R U P A 2
C3B C 0.7280(6) 0.6533(4) 0.1339(7) 0.0522(15) Uani 0.5 1 d . . P A 2
H3B H 0.713126 0.631799 0.044864 0.063 Uiso 0.5 1 calc R U P A 2
C4B C 0.6670(2) 0.7197(2) 0.1653(3) 0.0502(7) Uani 0.5 1 d . . P A 2
C5B C 0.7011(10) 0.7650(11) 0.2801(16) 0.058(3) Uani 0.5 1 d . . P A 2
H5B H 0.670762 0.821206 0.292241 0.069 Uiso 0.5 1 calc R U P A 2
C6B C 0.7841(8) 0.7259(7) 0.3830(10) 0.051(2) Uani 0.5 1 d . . P A 2
H6B H 0.803937 0.757282 0.465385 0.061 Uiso 0.5 1 calc R U P A 2
C7B C 0.8333(2) 0.6562(2) 0.3778(3) 0.0542(8) Uani 0.5 1 d . . P A 2
C8B C 0.8852(2) 0.6016(2) 0.4966(4) 0.0630(10) Uani 0.5 1 d . . P A 2
C9B C 0.9310(3) 0.6313(2) 0.6266(4) 0.0662(10) Uani 0.5 1 d . . P A 2
H9B H 0.95142 0.692135 0.64251 0.079 Uiso 0.5 1 calc R U P A 2
C10B C 0.9466(2) 0.5722(2) 0.7321(4) 0.0576(8) Uani 0.5 1 d . . P A 2
H10B H 0.977561 0.593566 0.82012 0.069 Uiso 0.5 1 calc R U P A 2
C11B C 0.9181(2) 0.4820(2) 0.7136(3) 0.0498(7) Uani 0.5 1 d . . P A 2
C12B C 0.8827(2) 0.4520(2) 0.5818(3) 0.0500(7) Uani 0.5 1 d . . P A 2
H12B H 0.869135 0.390267 0.564007 0.06 Uiso 0.5 1 calc R U P A 2
C13B C 0.8675(2) 0.5111(3) 0.4785(3) 0.0607(9) Uani 0.5 1 d . . P A 2
H13B H 0.843485 0.488833 0.38986 0.073 Uiso 0.5 1 calc R U P A 2
C14 C 0.8983(2) 0.4243(2) 0.8208(3) 0.0523(7) Uani 1 1 d . . . . .
C15 C 0.8620(3) 0.4615(3) 0.9233(4) 0.0677(9) Uani 1 1 d . . . . .
H15 H 0.879293 0.521862 0.948537 0.081 Uiso 1 1 calc R U . . .
C16 C 0.8012(3) 0.4122(3) 0.9891(4) 0.0681(9) Uani 1 1 d . . . . .
H16 H 0.77745 0.43977 1.058479 0.082 Uiso 1 1 calc R U . . .
C17 C 0.7742(2) 0.3244(2) 0.9571(3) 0.0546(8) Uani 1 1 d . . . . .
C18 C 0.8276(3) 0.2833(2) 0.8720(4) 0.0640(9) Uani 1 1 d . . . . .
H18 H 0.822177 0.220481 0.859483 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8881(3) 0.3324(2) 0.8058(4) 0.0616(9) Uani 1 1 d . . . . .
H19 H 0.923391 0.302567 0.748849 0.074 Uiso 1 1 calc R U . . .
C20 C 0.6726(3) 0.2868(2) 0.9780(3) 0.0593(9) Uani 1 1 d . . . . .
C21 C 0.6097(3) 0.3345(4) 1.0437(3) 0.0848(14) Uani 1 1 d . . . . .
H21 H 0.643643 0.375027 1.112423 0.102 Uiso 1 1 calc R U . . .
C22 C 0.4998(3) 0.3244(4) 1.0118(3) 0.0851(13) Uani 1 1 d . . . . .
H22 H 0.459231 0.359519 1.05697 0.102 Uiso 1 1 calc R U . . .
C23 C 0.4466(3) 0.2640(2) 0.9146(3) 0.0579(8) Uani 1 1 d . . . . .
C24 C 0.5118(3) 0.2046(2) 0.8707(5) 0.0818(12) Uani 1 1 d . . . . .
H24 H 0.47985 0.154882 0.817889 0.098 Uiso 1 1 calc R U . . .
C25 C 0.6227(3) 0.2157(2) 0.9018(5) 0.0812(13) Uani 1 1 d . . . . .
H25 H 0.665072 0.173476 0.870112 0.097 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O1A C1A 1.199(6) . ?
C1A C13A 1.420(6) . ?
C1A C2A 1.478(8) . ?
C2A C7A 1.241(6) . ?
C2A C3A 1.384(9) . ?
C3A C4A 1.432(7) . ?
C3A H3A 0.95 . ?
C4A C5A 1.403(16) . ?
C4A C23 1.495(4) 3_666 ?
C5A C6A 1.37(2) . ?
C5A H5A 0.95 . ?
C6A C7A 1.476(10) . ?
C6A H6A 0.95 . ?
C7A C8A 1.482(5) . ?
C8A C13A 1.378(5) . ?
C8A C9A 1.394(5) . ?
C9A C10A 1.382(5) . ?
C9A H9A 0.95 . ?
C10A C11A 1.400(5) . ?
C10A H10A 0.95 . ?
C11A C12A 1.397(4) . ?
C11A C14 1.485(4) . ?
C12A C13A 1.364(4) . ?
C12A H12A 0.95 . ?
C2B C3B 1.377(9) . ?
C2B C7B 1.576(7) . ?
C2B H2B 0.95 . ?
C3B C4B 1.360(8) . ?
C3B H3B 0.95 . ?
C4B C5B 1.341(17) . ?
C4B C23 1.495(4) 3_666 ?
C5B C6B 1.419(18) . ?
C5B H5B 0.95 . ?
C6B C7B 1.230(11) . ?
C6B H6B 0.95 . ?
C7B C8B 1.482(5) . ?
C8B C13B 1.378(5) . ?
C8B C9B 1.394(5) . ?
C9B C10B 1.382(5) . ?
C9B H9B 0.95 . ?
C10B C11B 1.400(5) . ?
C10B H10B 0.95 . ?
C11B C12B 1.397(4) . ?
C11B C14 1.485(4) . ?
C12B C13B 1.364(4) . ?
C12B H12B 0.95 . ?
C13B H13B 0.95 . ?
C14 C19 1.386(5) . ?
C14 C15 1.390(5) . ?
C15 C16 1.384(5) . ?
C15 H15 0.95 . ?
C16 C17 1.378(5) . ?
C16 H16 0.95 . ?
C17 C18 1.401(5) . ?
C17 C20 1.492(5) . ?
C18 C19 1.380(5) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C25 1.379(5) . ?
C20 C21 1.388(6) . ?
C21 C22 1.372(5) . ?
C21 H21 0.95 . ?
C22 C23 1.391(6) . ?
C22 H22 0.95 . ?
C23 C24 1.383(6) . ?
C24 C25 1.387(6) . ?
C24 H24 0.95 . ?
C25 H25 0.95 . ?

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
O1A C1A C13A 121.3(5) . . ?
O1A C1A C2A 128.7(5) . . ?
C13A C1A C2A 110.0(4) . . ?
C7A C2A C3A 123.1(5) . . ?
C7A C2A C1A 110.1(5) . . ?
C3A C2A C1A 125.6(5) . . ?
C2A C3A C4A 120.6(5) . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A H3A 119.7 . . ?
C5A C4A C3A 113.7(7) . . ?
C5A C4A C23 125.9(7) . 3_666 ?
C3A C4A C23 116.3(3) . 3_666 ?
C6A C5A C4A 126.0(12) . . ?
C6A C5A H5A 117 . . ?
C4A C5A H5A 117 . . ?
C5A C6A C7A 113.8(9) . . ?
C5A C6A H6A 123.1 . . ?
C7A C6A H6A 123.1 . . ?
C2A C7A C6A 122.6(5) . . ?
C2A C7A C8A 105.4(4) . . ?
C6A C7A C8A 128.7(5) . . ?
C13A C8A C9A 117.3(3) . . ?
C13A C8A C7A 114.0(3) . . ?
C9A C8A C7A 127.6(3) . . ?
C10A C9A C8A 119.9(3) . . ?
C10A C9A H9A 120 . . ?
C8A C9A H9A 120 . . ?
C9A C10A C11A 122.1(3) . . ?
C9A C10A H10A 118.9 . . ?
C11A C10A H10A 118.9 . . ?
C12A C11A C10A 116.7(3) . . ?
C12A C11A C14 118.2(3) . . ?
C10A C11A C14 123.3(3) . . ?
C13A C12A C11A 120.3(3) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C12A C13A C8A 123.1(3) . . ?
C12A C13A C1A 133.7(4) . . ?
C8A C13A C1A 100.2(3) . . ?
C3B C2B C7B 118.1(5) . . ?
C3B C2B H2B 120.9 . . ?
C7B C2B H2B 120.9 . . ?
C4B C3B C2B 119.6(6) . . ?
C4B C3B H3B 120.2 . . ?
C2B C3B H3B 120.2 . . ?
C5B C4B C3B 120.8(7) . . ?
C5B C4B C23 116.7(7) . 3_666 ?
C3B C4B C23 121.9(4) . 3_666 ?
C4B C5B C6B 117.6(12) . . ?
C4B C5B H5B 121.2 . . ?
C6B C5B H5B 121.2 . . ?
C7B C6B C5B 127.6(10) . . ?
C7B C6B H6B 116.2 . . ?
C5B C6B H6B 116.2 . . ?
C6B C7B C8B 123.6(6) . . ?
C6B C7B C2B 113.2(6) . . ?
C8B C7B C2B 121.5(4) . . ?
C13B C8B C9B 117.3(3) . . ?
C13B C8B C7B 114.0(3) . . ?
C9B C8B C7B 127.6(3) . . ?
C10B C9B C8B 119.9(3) . . ?
C10B C9B H9B 120 . . ?
C8B C9B H9B 120 . . ?
C9B C10B C11B 122.1(3) . . ?
C9B C10B H10B 118.9 . . ?
C11B C10B H10B 118.9 . . ?
C12B C11B C10B 116.7(3) . . ?
C12B C11B C14 118.2(3) . . ?
C10B C11B C14 123.3(3) . . ?
C13B C12B C11B 120.3(3) . . ?
C13B C12B H12B 119.8 . . ?
C11B C12B H12B 119.8 . . ?
C12B C13B C8B 123.1(3) . . ?
C12B C13B H13B 118.5 . . ?
C8B C13B H13B 118.5 . . ?
C19 C14 C15 116.2(3) . . ?
C19 C14 C11A 121.5(3) . . ?
C15 C14 C11A 120.2(3) . . ?
C19 C14 C11B 121.5(3) . . ?
C15 C14 C11B 120.2(3) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 122.0(4) . . ?
C17 C16 H16 119 . . ?
C15 C16 H16 119 . . ?
C16 C17 C18 115.9(3) . . ?
C16 C17 C20 119.9(3) . . ?
C18 C17 C20 121.7(3) . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 121.4(3) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?
C25 C20 C21 115.8(4) . . ?
C25 C20 C17 119.9(3) . . ?
C21 C20 C17 121.9(4) . . ?
C22 C21 C20 121.7(4) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 121.5(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 115.7(4) . . ?
C24 C23 C4A 120.8(3) . 3_666 ?
C22 C23 C4A 121.0(4) . 3_666 ?
C23 C24 C25 121.6(4) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C20 C25 C24 121.2(4) . . ?
C20 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?

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
O1A C1A C2A C7A -174.0(5) . . . . ?
C13A C1A C2A C7A 6.4(6) . . . . ?
O1A C1A C2A C3A 18.3(10) . . . . ?
C13A C1A C2A C3A -161.3(6) . . . . ?
C7A C2A C3A C4A -3.8(9) . . . . ?
C1A C2A C3A C4A 162.4(5) . . . . ?
C2A C3A C4A C5A 5.2(8) . . . . ?
C2A C3A C4A C23 -153.4(5) . . . 3_666 ?
C3A C4A C5A C6A -5.1(12) . . . . ?
C23 C4A C5A C6A 151.1(8) 3_666 . . . ?
C4A C5A C6A C7A 3.1(13) . . . . ?
C3A C2A C7A C6A 1.5(9) . . . . ?
C1A C2A C7A C6A -166.5(5) . . . . ?
C3A C2A C7A C8A 162.5(6) . . . . ?
C1A C2A C7A C8A -5.6(5) . . . . ?
C5A C6A C7A C2A -1.0(10) . . . . ?
C5A C6A C7A C8A -157.3(6) . . . . ?
C2A C7A C8A C13A 3.4(5) . . . . ?
C6A C7A C8A C13A 162.8(5) . . . . ?
C2A C7A C8A C9A -164.0(4) . . . . ?
C6A C7A C8A C9A -4.5(6) . . . . ?
C13A C8A C9A C10A -6.5(5) . . . . ?
C7A C8A C9A C10A 160.5(3) . . . . ?
C8A C9A C10A C11A 0.3(5) . . . . ?
C9A C10A C11A C12A 6.0(4) . . . . ?
C9A C10A C11A C14 -158.6(3) . . . . ?
C10A C11A C12A C13A -6.1(4) . . . . ?
C14 C11A C12A C13A 159.3(3) . . . . ?
C11A C12A C13A C8A -0.2(5) . . . . ?
C11A C12A C13A C1A -156.3(4) . . . . ?
C9A C8A C13A C12A 6.5(5) . . . . ?
C7A C8A C13A C12A -162.2(3) . . . . ?
C9A C8A C13A C1A 169.3(3) . . . . ?
C7A C8A C13A C1A 0.5(4) . . . . ?
O1A C1A C13A C12A -23.5(8) . . . . ?
C2A C1A C13A C12A 156.2(4) . . . . ?
O1A C1A C13A C8A 176.7(4) . . . . ?
C2A C1A C13A C8A -3.7(5) . . . . ?
C7B C2B C3B C4B -0.6(10) . . . . ?
C2B C3B C4B C5B 15.8(11) . . . . ?
C2B C3B C4B C23 -154.6(5) . . . 3_666 ?
C3B C4B C5B C6B -18.1(12) . . . . ?
C23 C4B C5B C6B 152.8(7) 3_666 . . . ?
C4B C5B C6B C7B 3.8(15) . . . . ?
C5B C6B C7B C8B -154.8(8) . . . . ?
C5B C6B C7B C2B 10.5(12) . . . . ?
C3B C2B C7B C6B -12.0(9) . . . . ?
C3B C2B C7B C8B 153.6(5) . . . . ?
C6B C7B C8B C13B 135.9(6) . . . . ?
C2B C7B C8B C13B -28.2(5) . . . . ?
C6B C7B C8B C9B -31.4(7) . . . . ?
C2B C7B C8B C9B 164.4(4) . . . . ?
C13B C8B C9B C10B -6.5(5) . . . . ?
C7B C8B C9B C10B 160.5(3) . . . . ?
C8B C9B C10B C11B 0.3(5) . . . . ?
C9B C10B C11B C12B 6.0(4) . . . . ?
C9B C10B C11B C14 -158.6(3) . . . . ?
C10B C11B C12B C13B -6.1(4) . . . . ?
C14 C11B C12B C13B 159.3(3) . . . . ?
C11B C12B C13B C8B -0.2(5) . . . . ?
C9B C8B C13B C12B 6.5(5) . . . . ?
C7B C8B C13B C12B -162.2(3) . . . . ?
C12A C11A C14 C19 26.5(4) . . . . ?
C10A C11A C14 C19 -169.1(3) . . . . ?
C12A C11A C14 C15 -136.7(3) . . . . ?
C10A C11A C14 C15 27.6(4) . . . . ?
C12B C11B C14 C19 26.5(4) . . . . ?
C10B C11B C14 C19 -169.1(3) . . . . ?
C12B C11B C14 C15 -136.7(3) . . . . ?
C10B C11B C14 C15 27.6(4) . . . . ?
C19 C14 C15 C16 -11.7(5) . . . . ?
C11A C14 C15 C16 152.4(3) . . . . ?
C11B C14 C15 C16 152.4(3) . . . . ?
C14 C15 C16 C17 0.3(6) . . . . ?
C15 C16 C17 C18 11.2(5) . . . . ?
C15 C16 C17 C20 -151.1(3) . . . . ?
C16 C17 C18 C19 -11.3(5) . . . . ?
C20 C17 C18 C19 150.6(3) . . . . ?
C17 C18 C19 C14 -0.1(5) . . . . ?
C15 C14 C19 C18 11.6(5) . . . . ?
C11A C14 C19 C18 -152.3(3) . . . . ?
C11B C14 C19 C18 -152.3(3) . . . . ?
C16 C17 C20 C25 154.1(3) . . . . ?
C18 C17 C20 C25 -7.2(4) . . . . ?
C16 C17 C20 C21 -7.7(4) . . . . ?
C18 C17 C20 C21 -168.9(3) . . . . ?
C25 C20 C21 C22 -14.0(6) . . . . ?
C17 C20 C21 C22 148.5(4) . . . . ?
C20 C21 C22 C23 1.9(7) . . . . ?
C21 C22 C23 C24 11.2(6) . . . . ?
C21 C22 C23 C4A -150.9(4) . . . 3_666 ?
C22 C23 C24 C25 -12.0(6) . . . . ?
C4A C23 C24 C25 150.1(4) 3_666 . . . ?
C21 C20 C25 C24 13.1(6) . . . . ?
C17 C20 C25 C24 -149.8(4) . . . . ?
C23 C24 C25 C20 -0.1(7) . . . . ?




