# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_O-bridged-nano-ring-Fe-complex
_database_code_depnum_ccdc_archive 'CCDC 1523315'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H18 Fe O4'
_chemical_formula_weight         558.34

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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8576(7)
_cell_length_b                   9.5150(7)
_cell_length_c                   15.8743(12)
_cell_angle_alpha                79.571(2)
_cell_angle_beta                 74.479(2)
_cell_angle_gamma                86.413(2)
_cell_volume                     1267.66(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    540
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5895
_exptl_absorpt_correction_T_max  0.7301
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17099
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4568
_reflns_number_gt                3983
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0978P)²+0.1963P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4568
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1485
_refine_ls_wR_factor_gt          0.1402
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.70786(4) 0.79509(4) 0.52890(2) 0.03465(17) Uani 1 1 d . . .
O1 O 0.47298(19) 0.85937(18) 0.57048(11) 0.0361(4) Uani 1 1 d . . .
O2 O 1.0000(3) 0.6454(3) 0.52996(16) 0.0600(6) Uani 1 1 d . . .
O3 O 0.6901(4) 0.6905(4) 0.36827(18) 0.0944(10) Uani 1 1 d . . .
O4 O 0.8555(3) 1.0769(2) 0.46413(17) 0.0649(6) Uani 1 1 d . . .
C1 C 0.5832(3) 0.6637(2) 0.63412(15) 0.0304(5) Uani 1 1 d . . .
C2 C 0.6307(3) 0.7881(2) 0.66005(15) 0.0295(5) Uani 1 1 d . . .
C3 C 0.4981(3) 0.8994(3) 0.65113(16) 0.0338(5) Uani 1 1 d . . .
H3A H 0.5244 0.9995 0.6467 0.041 Uiso 1 1 calc R . .
C4 C 0.3534(3) 0.8461(3) 0.72223(16) 0.0332(5) Uani 1 1 d . . .
C5 C 0.3093(3) 0.7309(3) 0.69822(16) 0.0334(5) Uani 1 1 d . . .
C6 C 0.4250(3) 0.7118(3) 0.61262(16) 0.0331(5) Uani 1 1 d . . .
H6A H 0.3895 0.6553 0.5759 0.040 Uiso 1 1 calc R . .
C7 C 0.6099(3) 0.5142(2) 0.67411(16) 0.0319(5) Uani 1 1 d . . .
C8 C 0.6664(3) 0.4094(3) 0.62325(19) 0.0431(6) Uani 1 1 d . . .
H8A H 0.6939 0.4335 0.5617 0.052 Uiso 1 1 calc R . .
C9 C 0.6829(4) 0.2684(3) 0.6629(2) 0.0537(7) Uani 1 1 d . . .
H9A H 0.7235 0.1994 0.6279 0.064 Uiso 1 1 calc R . .
C10 C 0.6393(4) 0.2314(3) 0.7532(2) 0.0541(8) Uani 1 1 d . . .
H10A H 0.6475 0.1366 0.7797 0.065 Uiso 1 1 calc R . .
C11 C 0.5832(3) 0.3345(3) 0.8053(2) 0.0429(6) Uani 1 1 d . . .
H11A H 0.5534 0.3086 0.8668 0.051 Uiso 1 1 calc R . .
C12 C 0.5708(3) 0.4765(2) 0.76688(16) 0.0316(5) Uani 1 1 d . . .
C13 C 0.7098(3) 0.7840(2) 0.73213(15) 0.0302(5) Uani 1 1 d . . .
C14 C 0.6535(3) 0.6906(3) 0.81270(16) 0.0324(5) Uani 1 1 d . . .
C15 C 0.7220(3) 0.6902(3) 0.88181(17) 0.0415(6) Uani 1 1 d . . .
H15A H 0.6857 0.6284 0.9352 0.050 Uiso 1 1 calc R . .
C16 C 0.8437(3) 0.7808(3) 0.87184(19) 0.0472(7) Uani 1 1 d . . .
H16A H 0.8894 0.7789 0.9184 0.057 Uiso 1 1 calc R . .
C17 C 0.8976(3) 0.8733(3) 0.7941(2) 0.0460(6) Uani 1 1 d . . .
H17A H 0.9781 0.9355 0.7882 0.055 Uiso 1 1 calc R . .
C18 C 0.8314(3) 0.8741(3) 0.72367(18) 0.0377(5) Uani 1 1 d . . .
H18A H 0.8694 0.9358 0.6704 0.045 Uiso 1 1 calc R . .
C19 C 0.3189(3) 0.8817(3) 0.81169(17) 0.0374(6) Uani 1 1 d . . .
C20 C 0.3305(3) 0.7698(3) 0.88120(16) 0.0360(5) Uani 1 1 d . . .
C21 C 0.3060(4) 0.7974(3) 0.96616(19) 0.0512(7) Uani 1 1 d . . .
H21A H 0.3108 0.7232 1.0124 0.061 Uiso 1 1 calc R . .
C22 C 0.2742(5) 0.9356(4) 0.9826(2) 0.0678(9) Uani 1 1 d . . .
H22A H 0.2595 0.9542 1.0398 0.081 Uiso 1 1 calc R . .
C23 C 0.2645(5) 1.0442(4) 0.9157(2) 0.0686(9) Uani 1 1 d . . .
H23A H 0.2419 1.1364 0.9278 0.082 Uiso 1 1 calc R . .
C24 C 0.2876(4) 1.0198(3) 0.8295(2) 0.0512(7) Uani 1 1 d . . .
H24A H 0.2823 1.0953 0.7841 0.061 Uiso 1 1 calc R . .
C25 C 0.2100(3) 0.6133(3) 0.75443(17) 0.0349(5) Uani 1 1 d . . .
C26 C 0.0940(3) 0.5532(3) 0.7300(2) 0.0458(6) Uani 1 1 d . . .
H26A H 0.0733 0.5886 0.6756 0.055 Uiso 1 1 calc R . .
C27 C 0.0088(3) 0.4414(3) 0.7857(2) 0.0574(8) Uani 1 1 d . . .
H27A H -0.0684 0.4005 0.7686 0.069 Uiso 1 1 calc R . .
C28 C 0.0373(4) 0.3899(3) 0.8663(3) 0.0619(9) Uani 1 1 d . . .
H28A H -0.0222 0.3152 0.9040 0.074 Uiso 1 1 calc R . .
C29 C 0.1530(3) 0.4475(3) 0.8921(2) 0.0502(7) Uani 1 1 d . . .
H29A H 0.1713 0.4115 0.9470 0.060 Uiso 1 1 calc R . .
C30 C 0.2419(3) 0.5587(3) 0.83663(17) 0.0358(5) Uani 1 1 d . . .
C31 C 0.5227(3) 0.5934(2) 0.81987(15) 0.0306(5) Uani 1 1 d . . .
C32 C 0.3732(3) 0.6283(3) 0.85482(15) 0.0329(5) Uani 1 1 d . . .
C33 C 0.8867(3) 0.7063(3) 0.52845(17) 0.0404(6) Uani 1 1 d . . .
C34 C 0.6935(3) 0.7322(4) 0.4300(2) 0.0527(7) Uani 1 1 d . . .
C35 C 0.7948(3) 0.9706(3) 0.48791(17) 0.0422(6) 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
Fe1 C33 1.747(3) . ?
Fe1 C34 1.816(3) . ?
Fe1 C35 1.818(3) . ?
Fe1 C2 2.000(2) . ?
Fe1 C1 2.001(2) . ?
Fe1 O1 2.0953(17) . ?
O1 C3 1.474(3) . ?
O1 C6 1.477(3) . ?
O2 C33 1.131(3) . ?
O3 C34 1.129(4) . ?
O4 C35 1.129(3) . ?
C1 C2 1.442(3) . ?
C1 C7 1.481(3) . ?
C1 C6 1.551(3) . ?
C2 C13 1.487(3) . ?
C2 C3 1.549(3) . ?
C3 C4 1.508(3) . ?
C4 C5 1.336(3) . ?
C4 C19 1.468(4) . ?
C5 C25 1.471(3) . ?
C5 C6 1.501(3) . ?
C7 C8 1.382(4) . ?
C7 C12 1.403(3) . ?
C8 C9 1.392(4) . ?
C9 C10 1.366(5) . ?
C10 C11 1.381(4) . ?
C11 C12 1.389(3) . ?
C12 C31 1.488(3) . ?
C13 C18 1.382(3) . ?
C13 C14 1.406(3) . ?
C14 C15 1.388(3) . ?
C14 C31 1.496(3) . ?
C15 C16 1.380(4) . ?
C16 C17 1.368(4) . ?
C17 C18 1.393(4) . ?
C19 C24 1.390(4) . ?
C19 C20 1.408(4) . ?
C20 C21 1.378(4) . ?
C20 C32 1.479(4) . ?
C21 C22 1.383(5) . ?
C22 C23 1.358(5) . ?
C23 C24 1.387(5) . ?
C25 C26 1.378(4) . ?
C25 C30 1.409(3) . ?
C26 C27 1.374(4) . ?
C27 C28 1.367(5) . ?
C28 C29 1.377(5) . ?
C29 C30 1.383(4) . ?
C30 C32 1.490(3) . ?
C31 C32 1.337(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
C33 Fe1 C34 92.91(13) . . ?
C33 Fe1 C35 94.36(12) . . ?
C34 Fe1 C35 104.45(14) . . ?
C33 Fe1 C2 97.34(11) . . ?
C34 Fe1 C2 148.82(12) . . ?
C35 Fe1 C2 104.03(11) . . ?
C33 Fe1 C1 95.16(11) . . ?
C34 Fe1 C1 107.64(12) . . ?
C35 Fe1 C1 145.92(11) . . ?
C2 Fe1 C1 42.26(9) . . ?
C33 Fe1 O1 161.17(10) . . ?
C34 Fe1 O1 96.93(11) . . ?
C35 Fe1 O1 98.64(10) . . ?
C2 Fe1 O1 66.35(8) . . ?
C1 Fe1 O1 66.58(8) . . ?
C3 O1 C6 94.95(16) . . ?
C3 O1 Fe1 91.62(12) . . ?
C6 O1 Fe1 91.69(12) . . ?
C2 C1 C7 124.68(19) . . ?
C2 C1 C6 103.22(19) . . ?
C7 C1 C6 121.10(19) . . ?
C2 C1 Fe1 68.84(12) . . ?
C7 C1 Fe1 132.51(17) . . ?
C6 C1 Fe1 93.19(14) . . ?
C1 C2 C13 124.6(2) . . ?
C1 C2 C3 104.14(19) . . ?
C13 C2 C3 119.73(19) . . ?
C1 C2 Fe1 68.90(13) . . ?
C13 C2 Fe1 133.76(16) . . ?
C3 C2 Fe1 93.14(14) . . ?
O1 C3 C4 103.45(18) . . ?
O1 C3 C2 95.72(17) . . ?
C4 C3 C2 107.01(19) . . ?
C5 C4 C19 127.8(2) . . ?
C5 C4 C3 105.9(2) . . ?
C19 C4 C3 121.8(2) . . ?
C4 C5 C25 128.2(2) . . ?
C4 C5 C6 106.5(2) . . ?
C25 C5 C6 121.7(2) . . ?
O1 C6 C5 103.36(19) . . ?
O1 C6 C1 95.89(17) . . ?
C5 C6 C1 107.41(19) . . ?
C8 C7 C12 118.9(2) . . ?
C8 C7 C1 122.2(2) . . ?
C12 C7 C1 118.8(2) . . ?
C7 C8 C9 120.9(3) . . ?
C10 C9 C8 120.0(3) . . ?
C9 C10 C11 120.0(3) . . ?
C10 C11 C12 120.7(3) . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 C31 122.8(2) . . ?
C7 C12 C31 117.7(2) . . ?
C18 C13 C14 119.3(2) . . ?
C18 C13 C2 121.9(2) . . ?
C14 C13 C2 118.7(2) . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 C31 122.5(2) . . ?
C13 C14 C31 118.2(2) . . ?
C16 C15 C14 120.5(3) . . ?
C17 C16 C15 120.5(2) . . ?
C16 C17 C18 119.8(2) . . ?
C13 C18 C17 120.6(2) . . ?
C24 C19 C20 119.2(2) . . ?
C24 C19 C4 123.6(2) . . ?
C20 C19 C4 117.0(2) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 C32 124.8(2) . . ?
C19 C20 C32 115.3(2) . . ?
C20 C21 C22 120.0(3) . . ?
C23 C22 C21 120.4(3) . . ?
C22 C23 C24 121.0(3) . . ?
C23 C24 C19 119.5(3) . . ?
C26 C25 C30 119.7(2) . . ?
C26 C25 C5 124.0(2) . . ?
C30 C25 C5 116.3(2) . . ?
C27 C26 C25 120.3(3) . . ?
C28 C27 C26 120.2(3) . . ?
C27 C28 C29 120.7(3) . . ?
C28 C29 C30 120.2(3) . . ?
C29 C30 C25 118.9(2) . . ?
C29 C30 C32 125.9(2) . . ?
C25 C30 C32 115.2(2) . . ?
C32 C31 C12 123.6(2) . . ?
C32 C31 C14 121.5(2) . . ?
C12 C31 C14 113.5(2) . . ?
C31 C32 C20 120.9(2) . . ?
C31 C32 C30 121.3(2) . . ?
C20 C32 C30 113.4(2) . . ?
O2 C33 Fe1 177.9(3) . . ?
O3 C34 Fe1 177.4(3) . . ?
O4 C35 Fe1 176.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_O-bridged-nanoring
_database_code_depnum_ccdc_archive 'CCDC 1523314'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H18 O'
_chemical_formula_weight         418.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.737(3)
_cell_length_b                   10.827(3)
_cell_length_c                   15.738(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.708(6)
_cell_angle_gamma                90.00
_cell_volume                     2089.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    63
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5411
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17427
_diffrn_reflns_av_R_equivalents  0.1721
_diffrn_reflns_av_sigmaI/netI    0.1377
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3773
_reflns_number_gt                1941
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1513P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3773
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1793
_refine_ls_R_factor_gt           0.0997
_refine_ls_wR_factor_ref         0.2908
_refine_ls_wR_factor_gt          0.2401
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9446(3) 0.0522(4) 1.1020(2) 0.0590(11) Uani 1 1 d . . .
C1 C 0.9082(4) 0.1676(5) 1.1286(3) 0.0486(14) Uani 1 1 d . . .
H1A H 0.9471 0.1977 1.1874 0.058 Uiso 1 1 calc R . .
C2 C 0.7846(4) 0.1444(5) 1.1121(3) 0.0425(13) Uani 1 1 d . . .
C3 C 0.7147(3) 0.2325(5) 1.1428(3) 0.0405(12) Uani 1 1 d . . .
C4 C 0.7193(4) 0.2512(6) 1.2308(3) 0.0519(14) Uani 1 1 d . . .
H4A H 0.7661 0.2029 1.2736 0.062 Uiso 1 1 calc R . .
C5 C 0.6570(5) 0.3390(6) 1.2564(4) 0.0612(16) Uani 1 1 d . . .
H5A H 0.6613 0.3499 1.3158 0.073 Uiso 1 1 calc R . .
C6 C 0.5884(5) 0.4107(6) 1.1939(4) 0.0626(16) Uani 1 1 d . . .
H6A H 0.5467 0.4711 1.2113 0.075 Uiso 1 1 calc R . .
C7 C 0.5802(5) 0.3946(5) 1.1057(4) 0.0559(14) Uani 1 1 d . . .
H7A H 0.5315 0.4423 1.0638 0.067 Uiso 1 1 calc R . .
C8 C 0.6448(4) 0.3070(5) 1.0792(3) 0.0419(12) Uani 1 1 d . . .
C9 C 0.6459(3) 0.2854(4) 0.9852(3) 0.0381(12) Uani 1 1 d . . .
C10 C 0.5949(3) 0.1685(5) 0.9450(3) 0.0390(12) Uani 1 1 d . . .
C11 C 0.4979(4) 0.1607(6) 0.8783(3) 0.0513(14) Uani 1 1 d . . .
H11A H 0.4577 0.2320 0.8594 0.062 Uiso 1 1 calc R . .
C12 C 0.4608(4) 0.0510(7) 0.8401(4) 0.0612(17) Uani 1 1 d . . .
H12A H 0.3961 0.0480 0.7953 0.073 Uiso 1 1 calc R . .
C13 C 0.5182(4) -0.0554(6) 0.8674(4) 0.0583(16) Uani 1 1 d . . .
H13A H 0.4923 -0.1303 0.8410 0.070 Uiso 1 1 calc R . .
C14 C 0.6145(4) -0.0519(5) 0.9340(3) 0.0510(14) Uani 1 1 d . . .
H14A H 0.6536 -0.1243 0.9515 0.061 Uiso 1 1 calc R . .
C15 C 0.6535(4) 0.0593(5) 0.9750(3) 0.0394(12) Uani 1 1 d . . .
C16 C 0.7584(4) 0.0702(4) 1.0412(3) 0.0393(12) Uani 1 1 d . . .
C17 C 0.8676(4) 0.0496(5) 1.0164(3) 0.0452(13) Uani 1 1 d . . .
H17A H 0.8709 -0.0218 0.9790 0.054 Uiso 1 1 calc R . .
C18 C 0.9103(3) 0.2522(6) 1.0501(3) 0.0476(14) Uani 1 1 d . . .
C19 C 0.8960(4) 0.3870(6) 1.0531(3) 0.0525(15) Uani 1 1 d . . .
C20 C 0.9731(5) 0.4625(7) 1.1085(4) 0.074(2) Uani 1 1 d . . .
H20A H 1.0379 0.4297 1.1436 0.088 Uiso 1 1 calc R . .
C21 C 0.9510(8) 0.5892(8) 1.1104(5) 0.090(3) Uani 1 1 d . . .
H21A H 1.0024 0.6409 1.1467 0.108 Uiso 1 1 calc R . .
C22 C 0.8558(8) 0.6384(7) 1.0604(5) 0.092(3) Uani 1 1 d . . .
H22A H 0.8431 0.7228 1.0623 0.110 Uiso 1 1 calc R . .
C23 C 0.7788(6) 0.5631(5) 1.0072(4) 0.0676(18) Uani 1 1 d . . .
H23A H 0.7139 0.5968 0.9731 0.081 Uiso 1 1 calc R . .
C24 C 0.7971(4) 0.4372(5) 1.0037(3) 0.0502(14) Uani 1 1 d . . .
C25 C 0.7170(4) 0.3490(4) 0.9502(3) 0.0403(12) Uani 1 1 d . . .
C26 C 0.7466(4) 0.3005(4) 0.8709(3) 0.0397(12) Uani 1 1 d . . .
C27 C 0.6958(5) 0.3359(5) 0.7851(3) 0.0542(14) Uani 1 1 d . . .
H27A H 0.6414 0.3958 0.7746 0.065 Uiso 1 1 calc R . .
C28 C 0.7249(5) 0.2831(6) 0.7152(4) 0.0647(17) Uani 1 1 d . . .
H28A H 0.6907 0.3073 0.6576 0.078 Uiso 1 1 calc R . .
C29 C 0.8055(5) 0.1939(6) 0.7313(4) 0.0636(16) Uani 1 1 d . . .
H29A H 0.8239 0.1568 0.6840 0.076 Uiso 1 1 calc R . .
C30 C 0.8584(4) 0.1594(5) 0.8153(3) 0.0501(14) Uani 1 1 d . . .
H30A H 0.9131 0.0999 0.8246 0.060 Uiso 1 1 calc R . .
C31 C 0.8319(4) 0.2115(4) 0.8867(3) 0.0403(12) Uani 1 1 d . . .
C32 C 0.8829(3) 0.1769(5) 0.9791(3) 0.0425(13) 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
O1 C1 1.435(7) . ?
O1 C17 1.435(5) . ?
C1 C18 1.544(7) . ?
C1 C2 1.545(6) . ?
C2 C16 1.341(7) . ?
C2 C3 1.473(7) . ?
C3 C4 1.384(7) . ?
C3 C8 1.402(7) . ?
C4 C5 1.367(8) . ?
C5 C6 1.366(8) . ?
C6 C7 1.375(8) . ?
C7 C8 1.392(7) . ?
C8 C9 1.501(6) . ?
C9 C25 1.367(7) . ?
C9 C10 1.484(7) . ?
C10 C11 1.391(6) . ?
C10 C15 1.410(7) . ?
C11 C12 1.357(8) . ?
C12 C13 1.370(8) . ?
C13 C14 1.381(7) . ?
C14 C15 1.392(7) . ?
C15 C16 1.461(6) . ?
C16 C17 1.559(7) . ?
C17 C32 1.531(7) . ?
C18 C32 1.351(7) . ?
C18 C19 1.474(8) . ?
C19 C20 1.389(8) . ?
C19 C24 1.399(7) . ?
C20 C21 1.403(11) . ?
C21 C22 1.362(11) . ?
C22 C23 1.372(9) . ?
C23 C24 1.386(8) . ?
C24 C25 1.482(7) . ?
C25 C26 1.494(7) . ?
C26 C27 1.384(7) . ?
C26 C31 1.422(7) . ?
C27 C28 1.377(8) . ?
C28 C29 1.382(8) . ?
C29 C30 1.364(7) . ?
C30 C31 1.379(7) . ?
C31 C32 1.471(6) . ?

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
C1 O1 C17 95.6(3) . . ?
O1 C1 C18 101.9(4) . . ?
O1 C1 C2 101.8(4) . . ?
C18 C1 C2 101.5(3) . . ?
C16 C2 C3 128.7(4) . . ?
C16 C2 C1 104.4(4) . . ?
C3 C2 C1 121.3(4) . . ?
C4 C3 C8 118.5(5) . . ?
C4 C3 C2 123.9(4) . . ?
C8 C3 C2 117.4(4) . . ?
C5 C4 C3 121.7(5) . . ?
C6 C5 C4 119.5(5) . . ?
C5 C6 C7 120.9(6) . . ?
C6 C7 C8 120.0(5) . . ?
C7 C8 C3 119.3(5) . . ?
C7 C8 C9 124.5(4) . . ?
C3 C8 C9 116.2(4) . . ?
C25 C9 C10 121.3(4) . . ?
C25 C9 C8 120.2(4) . . ?
C10 C9 C8 115.6(4) . . ?
C11 C10 C15 118.9(5) . . ?
C11 C10 C9 124.8(5) . . ?
C15 C10 C9 116.2(4) . . ?
C12 C11 C10 121.3(5) . . ?
C11 C12 C13 120.4(5) . . ?
C12 C13 C14 120.2(5) . . ?
C13 C14 C15 120.5(5) . . ?
C14 C15 C10 118.7(4) . . ?
C14 C15 C16 122.9(5) . . ?
C10 C15 C16 118.0(4) . . ?
C2 C16 C15 128.0(5) . . ?
C2 C16 C17 104.9(4) . . ?
C15 C16 C17 121.1(4) . . ?
O1 C17 C32 102.6(4) . . ?
O1 C17 C16 101.1(4) . . ?
C32 C17 C16 100.5(4) . . ?
C32 C18 C19 128.1(5) . . ?
C32 C18 C1 104.3(5) . . ?
C19 C18 C1 122.2(5) . . ?
C20 C19 C24 119.9(6) . . ?
C20 C19 C18 122.0(6) . . ?
C24 C19 C18 117.9(4) . . ?
C19 C20 C21 118.5(7) . . ?
C22 C21 C20 121.5(6) . . ?
C21 C22 C23 119.9(7) . . ?
C22 C23 C24 120.5(7) . . ?
C23 C24 C19 119.7(5) . . ?
C23 C24 C25 124.0(5) . . ?
C19 C24 C25 116.3(5) . . ?
C9 C25 C24 121.6(4) . . ?
C9 C25 C26 120.3(4) . . ?
C24 C25 C26 114.3(4) . . ?
C27 C26 C31 119.5(5) . . ?
C27 C26 C25 124.1(5) . . ?
C31 C26 C25 116.4(4) . . ?
C28 C27 C26 120.6(5) . . ?
C27 C28 C29 119.4(5) . . ?
C30 C29 C28 121.2(5) . . ?
C29 C30 C31 120.8(5) . . ?
C30 C31 C26 118.6(4) . . ?
C30 C31 C32 124.1(5) . . ?
C26 C31 C32 117.3(4) . . ?
C18 C32 C31 127.6(5) . . ?
C18 C32 C17 104.9(4) . . ?
C31 C32 C17 122.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.387
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_syn-furan-heptafulvalene-tetraphenylene
_database_code_depnum_ccdc_archive 'CCDC 1523317'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H29 Cl3 O4'
_chemical_formula_weight         812.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5417(4)
_cell_length_b                   14.8356(5)
_cell_length_c                   24.1274(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3773.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    221
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             1672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.601
_shelx_estimated_absorpt_T_min   0.423
_shelx_estimated_absorpt_T_max   0.624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4103
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19804
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.497
_diffrn_reflns_theta_max         68.774
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6892
_reflns_number_gt                4848
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.982

_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       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.0598P)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_abs_structure_details 
;
 Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.051(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6892
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
O1 O 0.3016(5) 0.2953(3) 0.49338(18) 0.0762(15) Uani 1 1 d . . . . .
O2 O 0.1545(3) 0.4401(3) 0.26672(14) 0.0441(9) Uani 1 1 d . . . . .
O3 O 0.6398(3) 0.7767(3) 0.34349(14) 0.0429(9) Uani 1 1 d . . . . .
O4 O 0.7796(4) 0.5873(3) 0.54347(15) 0.0558(11) Uani 1 1 d . . . . .
C1 C 0.3126(5) 0.3490(4) 0.4552(2) 0.0489(15) Uani 1 1 d . . . . .
C2 C 0.4098(5) 0.3294(4) 0.4111(2) 0.0420(13) Uani 1 1 d . . . . .
C3 C 0.5085(6) 0.2738(4) 0.4286(2) 0.0548(16) Uani 1 1 d . . . . .
H3A H 0.5079 0.2513 0.4646 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6066(6) 0.2514(5) 0.3937(3) 0.0627(18) Uani 1 1 d . . . . .
H4A H 0.6725 0.2152 0.4065 0.075 Uiso 1 1 calc R U . . .
C5 C 0.6074(5) 0.2825(4) 0.3399(2) 0.0531(16) Uani 1 1 d . . . . .
H5A H 0.6737 0.2674 0.3162 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5102(5) 0.3358(4) 0.3213(2) 0.0450(14) Uani 1 1 d . . . . .
H6A H 0.5111 0.3558 0.2848 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4092(5) 0.3610(4) 0.3560(2) 0.0368(12) Uani 1 1 d . . . . .
C8 C 0.3068(4) 0.4125(4) 0.3323(2) 0.0357(12) Uani 1 1 d . . . . .
C9 C 0.2164(5) 0.4633(4) 0.3565(2) 0.0376(12) Uani 1 1 d . . . . .
C10 C 0.1951(4) 0.4877(4) 0.4139(2) 0.0387(13) Uani 1 1 d . . . . .
C11 C 0.1229(5) 0.5650(4) 0.4251(2) 0.0472(15) Uani 1 1 d . . . . .
H11A H 0.0897 0.5982 0.3958 0.057 Uiso 1 1 calc R U . . .
C12 C 0.1002(6) 0.5925(5) 0.4785(3) 0.0593(17) Uani 1 1 d . . . . .
H12A H 0.0536 0.6446 0.4854 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1477(6) 0.5420(5) 0.5222(2) 0.0622(18) Uani 1 1 d . . . . .
H13A H 0.1336 0.5607 0.5585 0.075 Uiso 1 1 calc R U . . .
C14 C 0.2144(6) 0.4655(5) 0.5123(2) 0.0589(17) Uani 1 1 d . . . . .
H14A H 0.2435 0.4317 0.5421 0.071 Uiso 1 1 calc R U . . .
C15 C 0.2406(5) 0.4362(4) 0.4585(2) 0.0449(14) Uani 1 1 d . . . . .
C16 C 0.2909(4) 0.4319(4) 0.2697(2) 0.0367(12) Uani 1 1 d . . . . .
H16A H 0.3288 0.3874 0.2447 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3321(4) 0.5310(4) 0.25993(18) 0.0305(11) Uani 1 1 d . . . . .
C18 C 0.2430(4) 0.5802(4) 0.28440(18) 0.0305(11) Uani 1 1 d . . . . .
C19 C 0.1479(5) 0.5098(4) 0.3079(2) 0.0397(13) Uani 1 1 d . . . . .
H19A H 0.0627 0.5326 0.3161 0.048 Uiso 1 1 calc R U . . .
C20 C 0.4419(4) 0.5543(3) 0.22510(18) 0.0312(11) Uani 1 1 d . . . . .
C21 C 0.4508(5) 0.5112(4) 0.17342(19) 0.0405(13) Uani 1 1 d . . . . .
H21A H 0.3889 0.4698 0.1630 0.049 Uiso 1 1 calc R U . . .
C22 C 0.5506(5) 0.5294(4) 0.1376(2) 0.0446(14) Uani 1 1 d . . . . .
H22A H 0.5547 0.5014 0.1032 0.054 Uiso 1 1 calc R U . . .
C23 C 0.6431(5) 0.5891(4) 0.1535(2) 0.0498(15) Uani 1 1 d . . . . .
H23A H 0.7107 0.6008 0.1298 0.060 Uiso 1 1 calc R U . . .
C24 C 0.6369(5) 0.6315(4) 0.2036(2) 0.0438(14) Uani 1 1 d . . . . .
H24A H 0.7008 0.6715 0.2137 0.053 Uiso 1 1 calc R U . . .
C25 C 0.5356(4) 0.6158(4) 0.24048(19) 0.0329(12) Uani 1 1 d . . . . .
C26 C 0.5355(4) 0.6663(4) 0.29283(19) 0.0326(12) Uani 1 1 d . . . . .
C27 C 0.4467(4) 0.7126(4) 0.32001(19) 0.0331(12) Uani 1 1 d . . . . .
C28 C 0.2209(4) 0.6777(4) 0.28955(19) 0.0336(12) Uani 1 1 d . . . . .
C29 C 0.3155(4) 0.7389(4) 0.30565(18) 0.0334(12) Uani 1 1 d . . . . .
C30 C 0.2848(5) 0.8302(4) 0.3090(2) 0.0444(14) Uani 1 1 d . . . . .
H30A H 0.3464 0.8707 0.3208 0.053 Uiso 1 1 calc R U . . .
C31 C 0.1655(6) 0.8624(5) 0.2952(2) 0.0522(16) Uani 1 1 d . . . . .
H31A H 0.1484 0.9239 0.2964 0.063 Uiso 1 1 calc R U . . .
C32 C 0.0725(6) 0.8023(5) 0.2798(2) 0.0562(17) Uani 1 1 d . . . . .
H32A H -0.0084 0.8228 0.2710 0.067 Uiso 1 1 calc R U . . .
C33 C 0.1002(5) 0.7107(4) 0.2774(2) 0.0436(14) Uani 1 1 d . . . . .
H33A H 0.0365 0.6704 0.2675 0.052 Uiso 1 1 calc R U . . .
C34 C 0.6597(5) 0.6843(4) 0.3259(2) 0.0366(12) Uani 1 1 d . . . . .
H34A H 0.7386 0.6733 0.3055 0.044 Uiso 1 1 calc R U . . .
C35 C 0.6496(4) 0.6366(4) 0.38228(19) 0.0349(12) Uani 1 1 d . . . . .
C36 C 0.5601(4) 0.6827(4) 0.40984(19) 0.0345(12) Uani 1 1 d . . . . .
C37 C 0.5187(5) 0.7572(4) 0.36940(19) 0.0366(12) Uani 1 1 d . . . . .
H37A H 0.4760 0.8090 0.3864 0.044 Uiso 1 1 calc R U . . .
C38 C 0.7228(4) 0.5573(4) 0.3978(2) 0.0363(12) Uani 1 1 d . . . . .
C39 C 0.7753(5) 0.5037(4) 0.3557(2) 0.0457(14) Uani 1 1 d . . . . .
H39A H 0.7605 0.5186 0.3188 0.055 Uiso 1 1 calc R U . . .
C40 C 0.8484(5) 0.4293(4) 0.3680(3) 0.0547(16) Uani 1 1 d . . . . .
H40A H 0.8831 0.3947 0.3396 0.066 Uiso 1 1 calc R U . . .
C41 C 0.8702(5) 0.4060(4) 0.4231(2) 0.0546(16) Uani 1 1 d . . . . .
H41A H 0.9180 0.3551 0.4316 0.066 Uiso 1 1 calc R U . . .
C42 C 0.8216(5) 0.4576(4) 0.4646(2) 0.0482(15) Uani 1 1 d . . . . .
H42A H 0.8375 0.4416 0.5012 0.058 Uiso 1 1 calc R U . . .
C43 C 0.7476(4) 0.5348(4) 0.4535(2) 0.0377(12) Uani 1 1 d . . . . .
C44 C 0.7086(5) 0.5877(4) 0.5037(2) 0.0389(13) Uani 1 1 d . . . . .
C45 C 0.5823(5) 0.6321(4) 0.5087(2) 0.0393(13) Uani 1 1 d . . . . .
C46 C 0.5348(5) 0.6345(4) 0.5632(2) 0.0514(15) Uani 1 1 d . . . . .
H46A H 0.5820 0.6093 0.5919 0.062 Uiso 1 1 calc R U . . .
C47 C 0.4193(6) 0.6738(5) 0.5745(2) 0.0590(17) Uani 1 1 d . . . . .
H47A H 0.3890 0.6752 0.6107 0.071 Uiso 1 1 calc R U . . .
C48 C 0.3487(5) 0.7110(4) 0.5323(2) 0.0537(16) Uani 1 1 d . . . . .
H48A H 0.2697 0.7359 0.5400 0.064 Uiso 1 1 calc R U . . .
C49 C 0.3940(5) 0.7116(4) 0.4790(2) 0.0431(14) Uani 1 1 d . . . . .
H49A H 0.3457 0.7380 0.4511 0.052 Uiso 1 1 calc R U . . .
C50 C 0.5120(4) 0.6731(4) 0.4655(2) 0.0361(12) Uani 1 1 d . . . . .
C51 C 0.0189(6) 0.6564(5) 0.1053(3) 0.0635(19) Uani 1 1 d . . . . .
H51A H 0.0898 0.6876 0.0874 0.076 Uiso 1 1 calc R U . . .
Cl1 Cl -0.07188(15) 0.73768(12) 0.14187(7) 0.0706(5) Uani 1 1 d . . . . .
Cl2 Cl -0.07095(18) 0.60565(15) 0.05422(7) 0.0826(6) Uani 1 1 d . . . . .
Cl3 Cl 0.0818(3) 0.57747(18) 0.15143(9) 0.1109(9) 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
O1 C1 1.224(6) . ?
O2 C19 1.436(6) . ?
O2 C16 1.444(5) . ?
O3 C34 1.450(6) . ?
O3 C37 1.451(6) . ?
O4 C44 1.218(6) . ?
C1 C15 1.503(8) . ?
C1 C2 1.505(7) . ?
C2 C3 1.395(8) . ?
C2 C7 1.409(7) . ?
C3 C4 1.374(8) . ?
C4 C5 1.379(8) . ?
C5 C6 1.369(8) . ?
C6 C7 1.405(7) . ?
C7 C8 1.441(7) . ?
C8 C9 1.347(7) . ?
C8 C16 1.548(7) . ?
C9 C10 1.449(7) . ?
C9 C19 1.539(7) . ?
C10 C11 1.402(8) . ?
C10 C15 1.404(7) . ?
C11 C12 1.373(8) . ?
C12 C13 1.387(9) . ?
C13 C14 1.357(9) . ?
C14 C15 1.396(7) . ?
C16 C17 1.551(7) . ?
C17 C18 1.328(7) . ?
C17 C20 1.471(6) . ?
C18 C28 1.471(7) . ?
C18 C19 1.555(7) . ?
C20 C25 1.394(7) . ?
C20 C21 1.405(6) . ?
C21 C22 1.387(7) . ?
C22 C23 1.371(8) . ?
C23 C24 1.366(7) . ?
C24 C25 1.409(6) . ?
C25 C26 1.469(7) . ?
C26 C27 1.333(7) . ?
C26 C34 1.557(6) . ?
C27 C29 1.478(6) . ?
C27 C37 1.560(7) . ?
C28 C33 1.394(7) . ?
C28 C29 1.403(7) . ?
C29 C30 1.394(8) . ?
C30 C31 1.386(8) . ?
C31 C32 1.377(9) . ?
C32 C33 1.391(8) . ?
C34 C35 1.535(7) . ?
C35 C36 1.341(7) . ?
C35 C38 1.456(7) . ?
C36 C50 1.443(7) . ?
C36 C37 1.538(7) . ?
C38 C39 1.404(7) . ?
C38 C43 1.410(7) . ?
C39 C40 1.379(8) . ?
C40 C41 1.394(8) . ?
C41 C42 1.360(8) . ?
C42 C43 1.411(8) . ?
C43 C44 1.500(7) . ?
C44 C45 1.490(7) . ?
C45 C46 1.408(7) . ?
C45 C50 1.415(7) . ?
C46 C47 1.377(8) . ?
C47 C48 1.377(8) . ?
C48 C49 1.372(7) . ?
C49 C50 1.407(7) . ?
C51 Cl2 1.728(6) . ?
C51 Cl3 1.746(7) . ?
C51 Cl1 1.774(7) . ?

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
C19 O2 C16 94.3(4) . . ?
C34 O3 C37 93.7(4) . . ?
O1 C1 C15 118.2(5) . . ?
O1 C1 C2 118.1(6) . . ?
C15 C1 C2 123.2(5) . . ?
C3 C2 C7 119.1(5) . . ?
C3 C2 C1 114.0(5) . . ?
C7 C2 C1 126.8(5) . . ?
C4 C3 C2 121.3(6) . . ?
C3 C4 C5 120.0(6) . . ?
C6 C5 C4 119.8(5) . . ?
C5 C6 C7 121.8(5) . . ?
C6 C7 C2 118.0(5) . . ?
C6 C7 C8 118.2(5) . . ?
C2 C7 C8 123.6(5) . . ?
C9 C8 C7 130.9(5) . . ?
C9 C8 C16 104.0(4) . . ?
C7 C8 C16 124.5(4) . . ?
C8 C9 C10 131.6(5) . . ?
C8 C9 C19 104.6(4) . . ?
C10 C9 C19 122.9(5) . . ?
C11 C10 C15 118.8(5) . . ?
C11 C10 C9 118.2(5) . . ?
C15 C10 C9 122.9(5) . . ?
C12 C11 C10 121.3(6) . . ?
C11 C12 C13 119.3(6) . . ?
C14 C13 C12 120.3(6) . . ?
C13 C14 C15 121.9(6) . . ?
C14 C15 C10 118.4(6) . . ?
C14 C15 C1 114.7(5) . . ?
C10 C15 C1 126.9(5) . . ?
O2 C16 C8 99.9(4) . . ?
O2 C16 C17 101.1(4) . . ?
C8 C16 C17 107.1(4) . . ?
C18 C17 C20 132.9(5) . . ?
C18 C17 C16 104.7(4) . . ?
C20 C17 C16 122.0(4) . . ?
C17 C18 C28 133.6(5) . . ?
C17 C18 C19 104.5(4) . . ?
C28 C18 C19 121.9(4) . . ?
O2 C19 C9 100.5(4) . . ?
O2 C19 C18 101.5(4) . . ?
C9 C19 C18 106.0(4) . . ?
C25 C20 C21 119.1(4) . . ?
C25 C20 C17 124.0(4) . . ?
C21 C20 C17 116.9(4) . . ?
C22 C21 C20 120.9(5) . . ?
C23 C22 C21 119.5(5) . . ?
C24 C23 C22 120.7(5) . . ?
C23 C24 C25 121.2(5) . . ?
C20 C25 C24 118.5(5) . . ?
C20 C25 C26 124.2(4) . . ?
C24 C25 C26 117.3(5) . . ?
C27 C26 C25 133.4(4) . . ?
C27 C26 C34 104.4(4) . . ?
C25 C26 C34 121.9(4) . . ?
C26 C27 C29 132.6(5) . . ?
C26 C27 C37 104.7(4) . . ?
C29 C27 C37 121.5(4) . . ?
C33 C28 C29 118.6(5) . . ?
C33 C28 C18 118.2(5) . . ?
C29 C28 C18 123.2(4) . . ?
C30 C29 C28 118.7(5) . . ?
C30 C29 C27 117.3(5) . . ?
C28 C29 C27 124.0(5) . . ?
C31 C30 C29 122.1(6) . . ?
C32 C31 C30 119.2(6) . . ?
C31 C32 C33 119.6(5) . . ?
C32 C33 C28 121.7(6) . . ?
O3 C34 C35 99.6(4) . . ?
O3 C34 C26 101.0(4) . . ?
C35 C34 C26 108.5(4) . . ?
C36 C35 C38 131.1(5) . . ?
C36 C35 C34 104.7(5) . . ?
C38 C35 C34 124.2(4) . . ?
C35 C36 C50 131.2(5) . . ?
C35 C36 C37 104.6(4) . . ?
C50 C36 C37 124.2(5) . . ?
O3 C37 C36 99.6(4) . . ?
O3 C37 C27 100.6(4) . . ?
C36 C37 C27 108.5(4) . . ?
C39 C38 C43 118.8(5) . . ?
C39 C38 C35 118.8(4) . . ?
C43 C38 C35 122.3(5) . . ?
C40 C39 C38 121.2(5) . . ?
C39 C40 C41 119.7(6) . . ?
C42 C41 C40 120.0(6) . . ?
C41 C42 C43 121.7(5) . . ?
C38 C43 C42 118.4(5) . . ?
C38 C43 C44 126.5(5) . . ?
C42 C43 C44 115.0(5) . . ?
O4 C44 C45 119.2(5) . . ?
O4 C44 C43 117.8(5) . . ?
C45 C44 C43 122.8(4) . . ?
C46 C45 C50 119.4(5) . . ?
C46 C45 C44 113.9(5) . . ?
C50 C45 C44 126.7(4) . . ?
C47 C46 C45 120.7(5) . . ?
C46 C47 C48 120.0(5) . . ?
C49 C48 C47 120.5(5) . . ?
C48 C49 C50 121.4(5) . . ?
C49 C50 C45 117.9(5) . . ?
C49 C50 C36 119.0(5) . . ?
C45 C50 C36 122.9(4) . . ?
Cl2 C51 Cl3 111.8(4) . . ?
Cl2 C51 Cl1 110.8(3) . . ?
Cl3 C51 Cl1 110.2(4) . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.061

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_epoxide-nanoring-heptagon-octagon
_database_code_depnum_ccdc_archive 'CCDC 1523318'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H30 Cl2 O'
_chemical_formula_weight         729.65

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'
Cl Cl 0.1484 0.1585 '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                   12.3541(3)
_cell_length_b                   20.5251(6)
_cell_length_c                   15.5930(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.5622(16)
_cell_angle_gamma                90
_cell_volume                     3677.21(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    140
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6339
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30512
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.984
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6659
_reflns_number_gt                4058
_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       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.0930P)²+2.9082P] 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         6659
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.2047
_refine_ls_wR_factor_gt          0.1717
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_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
O1 O 1.05070(18) 0.18091(12) 0.62755(15) 0.0481(6) Uani 1 1 d . . . . .
C1 C 0.9372(3) 0.15133(16) 0.5895(2) 0.0383(8) Uani 1 1 d . . . . .
C2 C 0.8709(3) 0.17206(16) 0.4915(2) 0.0374(8) Uani 1 1 d . . . . .
C3 C 0.9300(3) 0.20233(17) 0.4432(2) 0.0445(8) Uani 1 1 d . . . . .
H3A H 1.0081 0.2128 0.4732 0.053 Uiso 1 1 calc R U . . .
C4 C 0.8751(3) 0.21750(19) 0.3507(2) 0.0499(9) Uani 1 1 d . . . . .
H4A H 0.9159 0.2385 0.3191 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7600(3) 0.20137(19) 0.3059(2) 0.0499(9) Uani 1 1 d . . . . .
H5A H 0.7230 0.2107 0.2435 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6994(3) 0.17143(17) 0.3535(2) 0.0431(8) Uani 1 1 d . . . . .
H6A H 0.6214 0.1610 0.3227 0.052 Uiso 1 1 calc R U . . .
C7 C 0.7526(3) 0.15645(15) 0.4470(2) 0.0367(7) Uani 1 1 d . . . . .
C8 C 0.6826(3) 0.12848(15) 0.4973(2) 0.0360(7) Uani 1 1 d . . . . .
C9 C 0.5751(3) 0.15656(16) 0.4837(2) 0.0385(8) Uani 1 1 d . . . . .
H9A H 0.5465 0.1885 0.4387 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5085(3) 0.13829(15) 0.5353(2) 0.0369(7) Uani 1 1 d . . . . .
C11 C 0.5451(3) 0.08535(16) 0.5959(2) 0.0392(8) Uani 1 1 d . . . . .
C12 C 0.6476(3) 0.05455(16) 0.6039(2) 0.0402(8) Uani 1 1 d . . . . .
H12A H 0.6693 0.0176 0.6409 0.048 Uiso 1 1 calc R U . . .
C13 C 0.7203(3) 0.07618(15) 0.5593(2) 0.0365(7) Uani 1 1 d . . . . .
C14 C 0.8340(3) 0.04371(16) 0.5799(2) 0.0406(8) Uani 1 1 d . . . . .
C15 C 0.8382(3) -0.02422(18) 0.5820(2) 0.0527(9) Uani 1 1 d . . . . .
H15A H 0.7696 -0.0477 0.5689 0.063 Uiso 1 1 calc R U . . .
C16 C 0.9416(4) -0.0573(2) 0.6031(3) 0.0640(11) Uani 1 1 d . . . . .
H16A H 0.9428 -0.1026 0.6044 0.077 Uiso 1 1 calc R U . . .
C17 C 1.0431(4) -0.0229(2) 0.6223(3) 0.0645(12) Uani 1 1 d . . . . .
H17A H 1.1130 -0.0451 0.6358 0.077 Uiso 1 1 calc R U . . .
C18 C 1.0428(3) 0.0443(2) 0.6217(2) 0.0526(10) Uani 1 1 d . . . . .
H18A H 1.1123 0.0670 0.6356 0.063 Uiso 1 1 calc R U . . .
C19 C 0.9379(3) 0.07831(17) 0.6002(2) 0.0400(8) Uani 1 1 d . . . . .
C20 C 0.4161(3) 0.18405(16) 0.5380(2) 0.0400(8) Uani 1 1 d . . . . .
C21 C 0.3104(3) 0.19147(18) 0.4653(2) 0.0482(9) Uani 1 1 d . . . . .
H21A H 0.2907 0.1635 0.4149 0.058 Uiso 1 1 calc R U . . .
C22 C 0.2343(3) 0.2403(2) 0.4676(3) 0.0587(11) Uani 1 1 d . . . . .
H22A H 0.1634 0.2449 0.4188 0.070 Uiso 1 1 calc R U . . .
C23 C 0.2630(3) 0.2817(2) 0.5414(3) 0.0608(11) Uani 1 1 d . . . . .
H23A H 0.2112 0.3143 0.5426 0.073 Uiso 1 1 calc R U . . .
C24 C 0.3684(3) 0.27555(19) 0.6140(3) 0.0532(10) Uani 1 1 d . . . . .
H24A H 0.3874 0.3043 0.6635 0.064 Uiso 1 1 calc R U . . .
C25 C 0.4460(3) 0.22699(17) 0.6137(2) 0.0420(8) Uani 1 1 d . . . . .
C26 C 0.5674(3) 0.22149(17) 0.6838(2) 0.0411(8) Uani 1 1 d . . . . .
C27 C 0.6511(3) 0.26349(16) 0.6752(2) 0.0419(8) Uani 1 1 d . . . . .
H27A H 0.6266 0.3015 0.6411 0.050 Uiso 1 1 calc R U . . .
C28 C 0.7698(3) 0.25113(15) 0.7154(2) 0.0375(8) Uani 1 1 d . . . . .
C29 C 0.8071(3) 0.19675(16) 0.7737(2) 0.0381(8) Uani 1 1 d . . . . .
C30 C 0.7232(3) 0.15804(16) 0.7887(2) 0.0414(8) Uani 1 1 d . . . . .
H30A H 0.7476 0.1243 0.8313 0.050 Uiso 1 1 calc R U . . .
C31 C 0.6047(3) 0.16786(16) 0.7428(2) 0.0405(8) Uani 1 1 d . . . . .
C32 C 0.5215(3) 0.11487(17) 0.7407(2) 0.0430(8) Uani 1 1 d . . . . .
C33 C 0.4767(3) 0.10478(19) 0.8100(3) 0.0553(10) Uani 1 1 d . . . . .
H33A H 0.4969 0.1327 0.8604 0.066 Uiso 1 1 calc R U . . .
C34 C 0.4019(4) 0.0530(2) 0.8034(3) 0.0637(11) Uani 1 1 d . . . . .
H34A H 0.3718 0.0465 0.8493 0.076 Uiso 1 1 calc R U . . .
C35 C 0.3720(3) 0.0111(2) 0.7294(3) 0.0607(11) Uani 1 1 d . . . . .
H35A H 0.3219 -0.0236 0.7256 0.073 Uiso 1 1 calc R U . . .
C36 C 0.4163(3) 0.02028(18) 0.6606(3) 0.0522(9) Uani 1 1 d . . . . .
H36A H 0.3965 -0.0085 0.6111 0.063 Uiso 1 1 calc R U . . .
C37 C 0.4901(3) 0.07214(16) 0.6650(2) 0.0412(8) Uani 1 1 d . . . . .
C38 C 0.8490(3) 0.29410(16) 0.6888(2) 0.0416(8) Uani 1 1 d . . . . .
C39 C 0.8311(3) 0.36129(17) 0.6863(2) 0.0523(10) Uani 1 1 d . . . . .
H39A H 0.7766 0.3783 0.7084 0.063 Uiso 1 1 calc R U . . .
C40 C 0.8927(4) 0.40299(19) 0.6519(3) 0.0620(11) Uani 1 1 d . . . . .
H40A H 0.8809 0.4477 0.6520 0.074 Uiso 1 1 calc R U . . .
C41 C 0.9722(3) 0.3779(2) 0.6173(3) 0.0591(11) Uani 1 1 d . . . . .
H41A H 1.0118 0.4056 0.5917 0.071 Uiso 1 1 calc R U . . .
C42 C 0.9923(3) 0.31207(18) 0.6207(2) 0.0498(9) Uani 1 1 d . . . . .
H42A H 1.0466 0.2958 0.5978 0.060 Uiso 1 1 calc R U . . .
C43 C 0.9340(3) 0.26879(16) 0.6574(2) 0.0393(8) Uani 1 1 d . . . . .
C44 C 0.9683(3) 0.19850(16) 0.6696(2) 0.0389(8) Uani 1 1 d . . . . .
C45 C 1.0063(3) 0.17607(15) 0.7687(2) 0.0383(8) Uani 1 1 d . . . . .
C46 C 0.9319(3) 0.17851(16) 0.8176(2) 0.0405(8) Uani 1 1 d . . . . .
C47 C 0.9771(3) 0.16112(18) 0.9108(2) 0.0515(9) Uani 1 1 d . . . . .
H47A H 0.9284 0.1615 0.9442 0.062 Uiso 1 1 calc R U . . .
C48 C 1.0909(3) 0.14357(19) 0.9538(2) 0.0581(11) Uani 1 1 d . . . . .
H48A H 1.1189 0.1325 1.0160 0.070 Uiso 1 1 calc R U . . .
C49 C 1.1640(3) 0.14227(19) 0.9056(2) 0.0579(11) Uani 1 1 d . . . . .
H49A H 1.2418 0.1310 0.9354 0.069 Uiso 1 1 calc R U . . .
C50 C 1.1227(3) 0.15753(17) 0.8134(2) 0.0487(9) Uani 1 1 d . . . . .
H50A H 1.1721 0.1555 0.7806 0.058 Uiso 1 1 calc R U . . .
C51 C 0.4743(16) 0.4923(4) 0.6538(7) 0.272(9) Uani 1 1 d . . . . .
H51A H 0.4773 0.5383 0.6407 0.326 Uiso 1 1 calc R U . . .
H51B H 0.4827 0.4883 0.7180 0.326 Uiso 1 1 calc R U . . .
Cl1 Cl 0.5705(6) 0.4609(3) 0.6422(3) 0.484(6) Uani 1 1 d . . . . .
Cl2 Cl 0.3278(6) 0.46045(16) 0.5805(5) 0.383(3) 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
O1 C1 1.441(4) . ?
O1 C44 1.444(4) . ?
C1 C2 1.506(4) . ?
C1 C19 1.508(5) . ?
C1 C44 1.514(4) . ?
C2 C3 1.374(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.385(5) . ?
C4 C5 1.375(5) . ?
C5 C6 1.377(5) . ?
C6 C7 1.395(4) . ?
C7 C8 1.480(4) . ?
C8 C9 1.391(4) . ?
C8 C13 1.406(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.401(4) . ?
C10 C20 1.491(4) . ?
C11 C12 1.379(4) . ?
C11 C37 1.495(5) . ?
C12 C13 1.396(4) . ?
C13 C14 1.479(4) . ?
C14 C15 1.395(5) . ?
C14 C19 1.397(5) . ?
C15 C16 1.375(5) . ?
C16 C17 1.373(6) . ?
C17 C18 1.378(6) . ?
C18 C19 1.401(5) . ?
C20 C21 1.387(4) . ?
C20 C25 1.409(5) . ?
C21 C22 1.384(5) . ?
C22 C23 1.369(6) . ?
C23 C24 1.383(5) . ?
C24 C25 1.384(5) . ?
C25 C26 1.501(4) . ?
C26 C27 1.390(5) . ?
C26 C31 1.400(5) . ?
C27 C28 1.390(4) . ?
C28 C29 1.406(4) . ?
C28 C38 1.484(5) . ?
C29 C30 1.393(4) . ?
C29 C46 1.487(4) . ?
C30 C31 1.387(4) . ?
C31 C32 1.489(5) . ?
C32 C33 1.399(5) . ?
C32 C37 1.406(5) . ?
C33 C34 1.387(5) . ?
C34 C35 1.377(6) . ?
C35 C36 1.385(5) . ?
C36 C37 1.386(5) . ?
C38 C39 1.395(5) . ?
C38 C43 1.411(5) . ?
C39 C40 1.378(5) . ?
C40 C41 1.381(6) . ?
C41 C42 1.372(5) . ?
C42 C43 1.392(5) . ?
C43 C44 1.496(5) . ?
C44 C45 1.512(4) . ?
C45 C46 1.395(5) . ?
C45 C50 1.400(4) . ?
C46 C47 1.397(4) . ?
C47 C48 1.365(5) . ?
C48 C49 1.371(5) . ?
C49 C50 1.374(5) . ?
C51 Cl1 1.421(15) . ?
C51 Cl2 1.867(16) . ?

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
C1 O1 C44 63.32(19) . . ?
O1 C1 C2 112.5(3) . . ?
O1 C1 C19 114.1(3) . . ?
C2 C1 C19 111.8(3) . . ?
O1 C1 C44 58.46(19) . . ?
C2 C1 C44 122.3(3) . . ?
C19 C1 C44 123.7(3) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 C1 118.9(3) . . ?
C7 C2 C1 121.1(3) . . ?
C2 C3 C4 121.1(3) . . ?
C5 C4 C3 119.6(3) . . ?
C4 C5 C6 120.0(3) . . ?
C5 C6 C7 121.3(3) . . ?
C6 C7 C2 118.1(3) . . ?
C6 C7 C8 119.7(3) . . ?
C2 C7 C8 122.1(3) . . ?
C9 C8 C13 118.5(3) . . ?
C9 C8 C7 118.0(3) . . ?
C13 C8 C7 123.4(3) . . ?
C8 C9 C10 122.2(3) . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 C20 117.8(3) . . ?
C11 C10 C20 122.0(3) . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 C37 119.8(3) . . ?
C10 C11 C37 120.5(3) . . ?
C11 C12 C13 123.1(3) . . ?
C12 C13 C8 118.3(3) . . ?
C12 C13 C14 118.9(3) . . ?
C8 C13 C14 122.8(3) . . ?
C15 C14 C19 118.7(3) . . ?
C15 C14 C13 118.6(3) . . ?
C19 C14 C13 122.7(3) . . ?
C16 C15 C14 121.4(4) . . ?
C17 C16 C15 119.5(4) . . ?
C16 C17 C18 120.9(4) . . ?
C17 C18 C19 120.0(4) . . ?
C14 C19 C18 119.5(3) . . ?
C14 C19 C1 120.9(3) . . ?
C18 C19 C1 119.3(3) . . ?
C21 C20 C25 119.6(3) . . ?
C21 C20 C10 123.1(3) . . ?
C25 C20 C10 116.8(3) . . ?
C22 C21 C20 120.2(4) . . ?
C23 C22 C21 120.2(3) . . ?
C22 C23 C24 120.5(4) . . ?
C23 C24 C25 120.5(4) . . ?
C24 C25 C20 119.0(3) . . ?
C24 C25 C26 124.0(3) . . ?
C20 C25 C26 116.6(3) . . ?
C27 C26 C31 118.3(3) . . ?
C27 C26 C25 117.6(3) . . ?
C31 C26 C25 122.5(3) . . ?
C26 C27 C28 122.8(3) . . ?
C27 C28 C29 118.5(3) . . ?
C27 C28 C38 117.4(3) . . ?
C29 C28 C38 124.0(3) . . ?
C30 C29 C28 118.3(3) . . ?
C30 C29 C46 119.3(3) . . ?
C28 C29 C46 122.4(3) . . ?
C31 C30 C29 122.6(3) . . ?
C30 C31 C26 118.9(3) . . ?
C30 C31 C32 119.6(3) . . ?
C26 C31 C32 120.1(3) . . ?
C33 C32 C37 119.4(3) . . ?
C33 C32 C31 123.9(3) . . ?
C37 C32 C31 116.7(3) . . ?
C34 C33 C32 119.9(4) . . ?
C35 C34 C33 120.5(4) . . ?
C34 C35 C36 120.2(4) . . ?
C35 C36 C37 120.4(4) . . ?
C36 C37 C32 119.6(3) . . ?
C36 C37 C11 124.6(3) . . ?
C32 C37 C11 115.7(3) . . ?
C39 C38 C43 119.0(3) . . ?
C39 C38 C28 118.8(3) . . ?
C43 C38 C28 121.9(3) . . ?
C40 C39 C38 121.4(4) . . ?
C39 C40 C41 119.6(4) . . ?
C42 C41 C40 119.8(4) . . ?
C41 C42 C43 122.1(4) . . ?
C42 C43 C38 118.1(3) . . ?
C42 C43 C44 120.2(3) . . ?
C38 C43 C44 121.5(3) . . ?
O1 C44 C43 113.4(3) . . ?
O1 C44 C45 112.4(2) . . ?
C43 C44 C45 113.0(3) . . ?
O1 C44 C1 58.23(19) . . ?
C43 C44 C1 122.5(3) . . ?
C45 C44 C1 122.5(3) . . ?
C46 C45 C50 120.0(3) . . ?
C46 C45 C44 121.9(3) . . ?
C50 C45 C44 117.9(3) . . ?
C45 C46 C47 117.9(3) . . ?
C45 C46 C29 122.5(3) . . ?
C47 C46 C29 119.6(3) . . ?
C48 C47 C46 121.6(4) . . ?
C47 C48 C49 120.1(3) . . ?
C48 C49 C50 120.2(3) . . ?
C49 C50 C45 120.1(4) . . ?
Cl1 C51 Cl2 115.5(6) . . ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_nanoring-containing-heptagon-octagon
_database_code_depnum_ccdc_archive 'CCDC 1523316'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H30 Cl2'
_chemical_formula_weight         713.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   12.2233(2)
_cell_length_b                   20.4397(3)
_cell_length_c                   15.6120(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.7594(9)
_cell_angle_gamma                90
_cell_volume                     3622.59(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    181
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             1480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7052
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56352
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.722
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6561
_reflns_number_gt                5069
_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       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_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)+(0.0785P)²+2.9450P] 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         6561
_refine_ls_number_parameters     478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_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 0.9311(2) 0.18010(11) 0.82029(15) 0.0361(5) Uani 1 1 d . . . . .
C2 C 0.9849(2) 0.16659(13) 0.91421(16) 0.0471(6) Uani 1 1 d . . . . .
H2A H 0.9409 0.1685 0.9516 0.057 Uiso 1 1 calc R U . . .
C3 C 1.1023(2) 0.15054(14) 0.95199(17) 0.0556(7) Uani 1 1 d . . . . .
H3A H 1.1371 0.1418 1.0148 0.067 Uiso 1 1 calc R U . . .
C4 C 1.1692(2) 0.14723(14) 0.89766(18) 0.0518(7) Uani 1 1 d . . . . .
H4A H 1.2490 0.1372 0.9239 0.062 Uiso 1 1 calc R U . . .
C5 C 1.1169(2) 0.15889(12) 0.80426(17) 0.0429(6) Uani 1 1 d . . . . .
H5A H 1.1615 0.1558 0.7674 0.051 Uiso 1 1 calc R U . . .
C6 C 0.99801(19) 0.17520(11) 0.76436(15) 0.0356(5) Uani 1 1 d . . . . .
C7 C 0.94346(18) 0.19380(11) 0.66482(15) 0.0346(5) Uani 1 1 d . . . . .
C8 C 0.92323(19) 0.26612(11) 0.65530(15) 0.0351(5) Uani 1 1 d . . . . .
C9 C 0.9853(2) 0.30665(13) 0.61774(16) 0.0446(6) Uani 1 1 d . . . . .
H9A H 1.0368 0.2882 0.5932 0.053 Uiso 1 1 calc R U . . .
C10 C 0.9717(2) 0.37383(14) 0.61632(19) 0.0538(7) Uani 1 1 d . . . . .
H10A H 1.0128 0.4001 0.5899 0.065 Uiso 1 1 calc R U . . .
C11 C 0.8977(2) 0.40197(13) 0.6537(2) 0.0539(7) Uani 1 1 d . . . . .
H11A H 0.8901 0.4472 0.6541 0.065 Uiso 1 1 calc R U . . .
C12 C 0.8348(2) 0.36277(12) 0.69069(18) 0.0457(6) Uani 1 1 d . . . . .
H12A H 0.7843 0.3820 0.7155 0.055 Uiso 1 1 calc R U . . .
C13 C 0.84529(19) 0.29482(11) 0.69170(15) 0.0368(5) Uani 1 1 d . . . . .
C14 C 0.76589(19) 0.25313(11) 0.72096(15) 0.0351(5) Uani 1 1 d . . . . .
C15 C 0.6454(2) 0.26575(11) 0.68146(16) 0.0376(5) Uani 1 1 d . . . . .
H15A H 0.6203 0.3042 0.6481 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5617(2) 0.22328(11) 0.68989(15) 0.0365(5) Uani 1 1 d . . . . .
C17 C 0.5996(2) 0.16925(12) 0.74879(15) 0.0376(5) Uani 1 1 d . . . . .
C18 C 0.7202(2) 0.15946(12) 0.79489(15) 0.0380(5) Uani 1 1 d . . . . .
H18A H 0.7454 0.1257 0.8377 0.046 Uiso 1 1 calc R U . . .
C19 C 0.80426(19) 0.19833(11) 0.77915(14) 0.0349(5) Uani 1 1 d . . . . .
C20 C 0.91309(19) 0.15105(11) 0.59489(15) 0.0347(5) Uani 1 1 d . . . . .
C21 C 0.9238(2) 0.07816(12) 0.60379(15) 0.0370(5) Uani 1 1 d . . . . .
C22 C 1.0310(2) 0.04577(14) 0.62362(17) 0.0475(6) Uani 1 1 d . . . . .
H22A H 1.1000 0.0699 0.6379 0.057 Uiso 1 1 calc R U . . .
C23 C 1.0355(3) -0.02178(15) 0.6223(2) 0.0591(8) Uani 1 1 d . . . . .
H23A H 1.1073 -0.0428 0.6351 0.071 Uiso 1 1 calc R U . . .
C24 C 0.9341(3) -0.05800(14) 0.6020(2) 0.0594(8) Uani 1 1 d . . . . .
H24A H 0.9375 -0.1035 0.6021 0.071 Uiso 1 1 calc R U . . .
C25 C 0.8274(2) -0.02672(13) 0.58153(19) 0.0493(6) Uani 1 1 d . . . . .
H25A H 0.7592 -0.0515 0.5677 0.059 Uiso 1 1 calc R U . . .
C26 C 0.8200(2) 0.04106(11) 0.58119(15) 0.0371(5) Uani 1 1 d . . . . .
C27 C 0.70413(19) 0.07335(11) 0.56013(15) 0.0346(5) Uani 1 1 d . . . . .
C28 C 0.6328(2) 0.05246(11) 0.60680(16) 0.0374(5) Uani 1 1 d . . . . .
H28A H 0.6540 0.0150 0.6431 0.045 Uiso 1 1 calc R U . . .
C29 C 0.53116(19) 0.08569(11) 0.60090(15) 0.0364(5) Uani 1 1 d . . . . .
C30 C 0.47913(19) 0.07394(11) 0.67242(16) 0.0374(5) Uani 1 1 d . . . . .
C31 C 0.4038(2) 0.02236(13) 0.66974(18) 0.0470(6) Uani 1 1 d . . . . .
H31A H 0.3801 -0.0062 0.6199 0.056 Uiso 1 1 calc R U . . .
C32 C 0.3641(2) 0.01351(14) 0.7413(2) 0.0527(7) Uani 1 1 d . . . . .
H32A H 0.3135 -0.0209 0.7391 0.063 Uiso 1 1 calc R U . . .
C33 C 0.3991(2) 0.05523(15) 0.8152(2) 0.0559(7) Uani 1 1 d . . . . .
H33A H 0.3717 0.0490 0.8628 0.067 Uiso 1 1 calc R U . . .
C34 C 0.4747(2) 0.10646(13) 0.81962(19) 0.0497(6) Uani 1 1 d . . . . .
H34A H 0.4985 0.1343 0.8703 0.060 Uiso 1 1 calc R U . . .
C35 C 0.5152(2) 0.11643(12) 0.74840(16) 0.0394(5) Uani 1 1 d . . . . .
C36 C 0.49405(19) 0.13863(11) 0.53990(15) 0.0353(5) Uani 1 1 d . . . . .
C37 C 0.55820(19) 0.15503(11) 0.48557(15) 0.0356(5) Uani 1 1 d . . . . .
H37A H 0.5285 0.1867 0.4400 0.043 Uiso 1 1 calc R U . . .
C38 C 0.66550(19) 0.12545(11) 0.49738(14) 0.0342(5) Uani 1 1 d . . . . .
C39 C 0.73750(19) 0.15329(11) 0.44750(15) 0.0340(5) Uani 1 1 d . . . . .
C40 C 0.6873(2) 0.16658(13) 0.35334(16) 0.0423(6) Uani 1 1 d . . . . .
H40A H 0.6086 0.1564 0.3208 0.051 Uiso 1 1 calc R U . . .
C41 C 0.7532(2) 0.19470(14) 0.30792(16) 0.0464(6) Uani 1 1 d . . . . .
H41A H 0.7188 0.2029 0.2449 0.056 Uiso 1 1 calc R U . . .
C42 C 0.8694(2) 0.21072(14) 0.35543(17) 0.0469(6) Uani 1 1 d . . . . .
H42A H 0.9132 0.2303 0.3248 0.056 Uiso 1 1 calc R U . . .
C43 C 0.9205(2) 0.19774(12) 0.44849(16) 0.0409(6) Uani 1 1 d . . . . .
H43A H 0.9995 0.2079 0.4802 0.049 Uiso 1 1 calc R U . . .
C44 C 0.85570(19) 0.16967(11) 0.49556(15) 0.0343(5) Uani 1 1 d . . . . .
C45 C 0.43813(19) 0.22926(12) 0.62040(16) 0.0374(5) Uani 1 1 d . . . . .
C46 C 0.40440(19) 0.18651(11) 0.54458(16) 0.0360(5) Uani 1 1 d . . . . .
C47 C 0.2971(2) 0.19596(13) 0.47254(17) 0.0429(6) Uani 1 1 d . . . . .
H47A H 0.2747 0.1682 0.4218 0.052 Uiso 1 1 calc R U . . .
C48 C 0.2233(2) 0.24627(14) 0.4756(2) 0.0502(7) Uani 1 1 d . . . . .
H48A H 0.1510 0.2518 0.4276 0.060 Uiso 1 1 calc R U . . .
C49 C 0.2565(2) 0.28816(14) 0.5494(2) 0.0522(7) Uani 1 1 d . . . . .
H49A H 0.2065 0.3221 0.5510 0.063 Uiso 1 1 calc R U . . .
C50 C 0.3639(2) 0.28049(13) 0.62182(18) 0.0455(6) Uani 1 1 d . . . . .
H50A H 0.3862 0.3095 0.6712 0.055 Uiso 1 1 calc R U . . .
C51 C 0.4741(8) 0.4957(3) 0.6496(5) 0.183(3) Uani 1 1 d . . . . .
H51A H 0.4760 0.5418 0.6356 0.220 Uiso 1 1 calc R U . . .
H51B H 0.4856 0.4923 0.7143 0.220 Uiso 1 1 calc R U . . .
Cl1 Cl 0.3279(4) 0.46427(11) 0.5817(3) 0.310(2) Uani 1 1 d . . . . .
Cl2 Cl 0.5767(4) 0.4628(2) 0.6357(2) 0.375(3) 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 C2 1.394(3) . ?
C1 C6 1.404(3) . ?
C1 C19 1.489(3) . ?
C2 C3 1.373(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.379(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.495(3) . ?
C7 C20 1.339(3) . ?
C7 C8 1.497(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.406(3) . ?
C9 C10 1.382(4) . ?
C10 C11 1.371(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.394(3) . ?
C13 C14 1.485(3) . ?
C14 C15 1.393(3) . ?
C14 C19 1.408(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.401(3) . ?
C16 C45 1.503(3) . ?
C17 C18 1.394(3) . ?
C17 C35 1.492(3) . ?
C18 C19 1.391(3) . ?
C20 C44 1.495(3) . ?
C20 C21 1.498(3) . ?
C21 C22 1.396(3) . ?
C21 C26 1.407(3) . ?
C22 C23 1.382(4) . ?
C23 C24 1.376(4) . ?
C24 C25 1.379(4) . ?
C25 C26 1.388(3) . ?
C26 C27 1.484(3) . ?
C27 C28 1.394(3) . ?
C27 C38 1.405(3) . ?
C28 C29 1.389(3) . ?
C29 C36 1.401(3) . ?
C29 C30 1.495(3) . ?
C30 C31 1.390(3) . ?
C30 C35 1.403(3) . ?
C31 C32 1.384(4) . ?
C32 C33 1.370(4) . ?
C33 C34 1.381(4) . ?
C34 C35 1.390(3) . ?
C36 C37 1.393(3) . ?
C36 C46 1.491(3) . ?
C37 C38 1.393(3) . ?
C38 C39 1.488(3) . ?
C39 C40 1.394(3) . ?
C39 C44 1.400(3) . ?
C40 C41 1.380(3) . ?
C41 C42 1.376(4) . ?
C42 C43 1.378(3) . ?
C43 C44 1.389(3) . ?
C45 C50 1.391(3) . ?
C45 C46 1.404(3) . ?
C46 C47 1.389(3) . ?
C47 C48 1.380(4) . ?
C48 C49 1.371(4) . ?
C49 C50 1.388(4) . ?
C51 Cl2 1.508(8) . ?
C51 Cl1 1.823(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.9(2) . . ?
C2 C1 C19 120.9(2) . . ?
C6 C1 C19 120.21(19) . . ?
C3 C2 C1 120.6(2) . . ?
C2 C3 C4 120.7(2) . . ?
C5 C4 C3 119.6(2) . . ?
C4 C5 C6 120.8(2) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 121.0(2) . . ?
C1 C6 C7 119.35(19) . . ?
C20 C7 C6 124.3(2) . . ?
C20 C7 C8 125.3(2) . . ?
C6 C7 C8 110.36(18) . . ?
C9 C8 C13 118.6(2) . . ?
C9 C8 C7 122.3(2) . . ?
C13 C8 C7 118.9(2) . . ?
C10 C9 C8 121.1(3) . . ?
C11 C10 C9 120.3(3) . . ?
C10 C11 C12 119.5(3) . . ?
C11 C12 C13 121.4(3) . . ?
C12 C13 C8 119.0(2) . . ?
C12 C13 C14 120.5(2) . . ?
C8 C13 C14 120.2(2) . . ?
C15 C14 C19 118.5(2) . . ?
C15 C14 C13 117.5(2) . . ?
C19 C14 C13 123.7(2) . . ?
C16 C15 C14 122.6(2) . . ?
C15 C16 C17 118.7(2) . . ?
C15 C16 C45 117.4(2) . . ?
C17 C16 C45 122.5(2) . . ?
C18 C17 C16 118.8(2) . . ?
C18 C17 C35 119.7(2) . . ?
C16 C17 C35 120.5(2) . . ?
C19 C18 C17 122.4(2) . . ?
C18 C19 C14 118.5(2) . . ?
C18 C19 C1 120.0(2) . . ?
C14 C19 C1 121.5(2) . . ?
C7 C20 C44 124.1(2) . . ?
C7 C20 C21 125.8(2) . . ?
C44 C20 C21 109.92(19) . . ?
C22 C21 C26 119.0(2) . . ?
C22 C21 C20 122.4(2) . . ?
C26 C21 C20 118.22(19) . . ?
C23 C22 C21 120.6(3) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C25 119.8(3) . . ?
C24 C25 C26 121.2(3) . . ?
C25 C26 C21 119.0(2) . . ?
C25 C26 C27 120.0(2) . . ?
C21 C26 C27 120.9(2) . . ?
C28 C27 C38 118.9(2) . . ?
C28 C27 C26 118.6(2) . . ?
C38 C27 C26 122.5(2) . . ?
C29 C28 C27 122.2(2) . . ?
C28 C29 C36 118.6(2) . . ?
C28 C29 C30 119.3(2) . . ?
C36 C29 C30 120.8(2) . . ?
C31 C30 C35 119.5(2) . . ?
C31 C30 C29 124.0(2) . . ?
C35 C30 C29 116.4(2) . . ?
C32 C31 C30 120.1(3) . . ?
C33 C32 C31 120.4(2) . . ?
C32 C33 C34 120.5(2) . . ?
C33 C34 C35 120.1(3) . . ?
C34 C35 C30 119.5(2) . . ?
C34 C35 C17 123.6(2) . . ?
C30 C35 C17 116.8(2) . . ?
C37 C36 C29 119.1(2) . . ?
C37 C36 C46 117.5(2) . . ?
C29 C36 C46 122.1(2) . . ?
C36 C37 C38 122.0(2) . . ?
C37 C38 C27 118.5(2) . . ?
C37 C38 C39 118.4(2) . . ?
C27 C38 C39 122.9(2) . . ?
C40 C39 C44 118.8(2) . . ?
C40 C39 C38 120.8(2) . . ?
C44 C39 C38 120.29(19) . . ?
C41 C40 C39 120.7(2) . . ?
C42 C41 C40 120.3(2) . . ?
C41 C42 C43 119.8(2) . . ?
C42 C43 C44 120.8(2) . . ?
C43 C44 C39 119.6(2) . . ?
C43 C44 C20 120.9(2) . . ?
C39 C44 C20 119.3(2) . . ?
C50 C45 C46 119.5(2) . . ?
C50 C45 C16 122.5(2) . . ?
C46 C45 C16 117.4(2) . . ?
C47 C46 C45 119.3(2) . . ?
C47 C46 C36 122.8(2) . . ?
C45 C46 C36 117.27(19) . . ?
C48 C47 C46 120.6(3) . . ?
C49 C48 C47 120.1(2) . . ?
C48 C49 C50 120.6(2) . . ?
C49 C50 C45 119.9(3) . . ?
Cl2 C51 Cl1 116.6(4) . . ?

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6



