# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_851_MX58_k2m_0m
_database_code_depnum_ccdc_archive 'CCDC 2022133'
loop_
_audit_author_name
_audit_author_address
'Kazutaka Shoyama'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        benzo[b]perylene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14'
_chemical_formula_sum            'C24 H14'
_chemical_formula_weight         302.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.5984(12)
_cell_length_b                   9.4354(11)
_cell_length_c                   14.6185(17)
_cell_angle_alpha                90
_cell_angle_beta                 90.547(3)
_cell_angle_gamma                90
_cell_volume                     1461.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      80.19

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.593
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6266
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26600
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.171
_diffrn_reflns_theta_max         80.217
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3164
_reflns_number_gt                2961
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXD
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0701P)²+0.2760P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3164
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.21730(9) 0.73142(10) 0.05668(6) 0.0258(2) Uani 1 1 d . . . . .
H1 H 0.239683 0.672450 0.006722 0.031 Uiso 1 1 calc R U . . .
C2 C 0.09198(9) 0.73193(11) 0.08708(7) 0.0287(2) Uani 1 1 d . . . . .
H2 H 0.030867 0.674036 0.057269 0.034 Uiso 1 1 calc R U . . .
C3 C 0.05711(8) 0.81517(10) 0.15933(7) 0.0276(2) Uani 1 1 d . . . . .
H3 H -0.027942 0.814469 0.179261 0.033 Uiso 1 1 calc R U . . .
C4 C 0.14678(8) 0.90212(10) 0.20446(6) 0.0244(2) Uani 1 1 d . . . . .
C5 C 0.27402(8) 0.90459(9) 0.17250(6) 0.0217(2) Uani 1 1 d . . . . .
C6 C 0.11437(8) 0.98391(10) 0.28221(7) 0.0281(2) Uani 1 1 d . . . . .
H6 H 0.029793 0.984177 0.303153 0.034 Uiso 1 1 calc R U . . .
C7 C 0.20405(9) 1.06248(10) 0.32730(7) 0.0299(2) Uani 1 1 d . . . . .
H7 H 0.182346 1.112857 0.381169 0.036 Uiso 1 1 calc R U . . .
C8 C 0.32805(9) 1.06898(10) 0.29428(6) 0.0269(2) Uani 1 1 d . . . . .
H8 H 0.388645 1.125379 0.325820 0.032 Uiso 1 1 calc R U . . .
C9 C 0.36413(8) 0.99503(9) 0.21676(6) 0.0222(2) Uani 1 1 d . . . . .
C10 C 0.49206(8) 1.00704(9) 0.17866(6) 0.0214(2) Uani 1 1 d . . . . .
C11 C 0.53015(8) 0.91416(9) 0.10724(6) 0.0203(2) Uani 1 1 d . . . . .
C12 C 0.57658(8) 1.10895(10) 0.21060(6) 0.0240(2) Uani 1 1 d . . . . .
H12 H 0.550278 1.174653 0.255815 0.029 Uiso 1 1 calc R U . . .
C13 C 0.69924(9) 1.11616(10) 0.17729(6) 0.0259(2) Uani 1 1 d . . . . .
H13 H 0.755663 1.186189 0.200202 0.031 Uiso 1 1 calc R U . . .
C14 C 0.73910(8) 1.02261(10) 0.11149(6) 0.0235(2) Uani 1 1 d . . . . .
H14 H 0.823848 1.026489 0.091056 0.028 Uiso 1 1 calc R U . . .
C15 C 0.65602(8) 0.92108(9) 0.07397(6) 0.0211(2) Uani 1 1 d . . . . .
C16 C 0.69545(8) 0.82557(9) 0.00160(6) 0.0219(2) Uani 1 1 d . . . . .
C17 C 0.81687(8) 0.83023(10) -0.03735(6) 0.0253(2) Uani 1 1 d . . . . .
H17 H 0.876275 0.898331 -0.016048 0.030 Uiso 1 1 calc R U . . .
C18 C 0.85039(9) 0.73767(11) -0.10566(7) 0.0289(2) Uani 1 1 d . . . . .
H18 H 0.932518 0.742466 -0.130952 0.035 Uiso 1 1 calc R U . . .
C19 C 0.76409(9) 0.63610(11) -0.13831(7) 0.0305(2) Uani 1 1 d . . . . .
H19 H 0.787889 0.572255 -0.185340 0.037 Uiso 1 1 calc R U . . .
C20 C 0.64545(9) 0.62945(10) -0.10205(6) 0.0275(2) Uani 1 1 d . . . . .
H20 H 0.587361 0.560497 -0.124111 0.033 Uiso 1 1 calc R U . . .
C21 C 0.60844(8) 0.72403(9) -0.03219(6) 0.0231(2) Uani 1 1 d . . . . .
C22 C 0.48303(8) 0.72116(9) 0.00217(6) 0.0232(2) Uani 1 1 d . . . . .
H22 H 0.425832 0.652317 -0.021235 0.028 Uiso 1 1 calc R U . . .
C23 C 0.44170(8) 0.81367(9) 0.06757(6) 0.0209(2) Uani 1 1 d . . . . .
C24 C 0.30910(8) 0.81515(9) 0.09800(6) 0.0218(2) 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 C24 1.3872(13) . ?
C1 C2 1.4045(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.3698(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.4141(13) . ?
C3 H3 0.9500 . ?
C4 C6 1.4187(13) . ?
C4 C5 1.4316(12) . ?
C5 C24 1.4297(12) . ?
C5 C9 1.4309(12) . ?
C6 C7 1.3695(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.4057(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.3876(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.4750(12) . ?
C10 C12 1.3918(13) . ?
C10 C11 1.4244(12) . ?
C11 C15 1.4259(12) . ?
C11 C23 1.4504(12) . ?
C12 C13 1.3942(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.3749(13) . ?
C13 H13 0.9500 . ?
C14 C15 1.4088(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.4540(12) . ?
C16 C17 1.4129(12) . ?
C16 C21 1.4154(13) . ?
C17 C18 1.3758(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.4052(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.3706(13) . ?
C19 H19 0.9500 . ?
C20 C21 1.4145(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.4257(12) . ?
C22 C23 1.3696(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.4782(12) . ?

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
C24 C1 C2 121.44(9) . . ?
C24 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 120.59(8) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.49(8) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C6 121.51(8) . . ?
C3 C4 C5 119.21(8) . . ?
C6 C4 C5 119.26(8) . . ?
C24 C5 C9 121.28(8) . . ?
C24 C5 C4 119.45(8) . . ?
C9 C5 C4 119.26(8) . . ?
C7 C6 C4 120.52(8) . . ?
C7 C6 H6 119.7 . . ?
C4 C6 H6 119.7 . . ?
C6 C7 C8 120.35(9) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.62(9) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C5 118.77(8) . . ?
C8 C9 C10 122.08(8) . . ?
C5 C9 C10 119.15(8) . . ?
C12 C10 C11 119.00(8) . . ?
C12 C10 C9 121.16(8) . . ?
C11 C10 C9 119.83(8) . . ?
C10 C11 C15 119.64(8) . . ?
C10 C11 C23 120.58(8) . . ?
C15 C11 C23 119.78(8) . . ?
C10 C12 C13 121.06(8) . . ?
C10 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.44(8) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.93(8) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C11 118.79(8) . . ?
C14 C15 C16 121.46(8) . . ?
C11 C15 C16 119.74(8) . . ?
C17 C16 C21 118.24(8) . . ?
C17 C16 C15 122.89(8) . . ?
C21 C16 C15 118.86(8) . . ?
C18 C17 C16 121.02(9) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.51(9) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.76(9) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.80(9) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 119.66(8) . . ?
C20 C21 C22 120.55(8) . . ?
C16 C21 C22 119.76(8) . . ?
C23 C22 C21 122.63(8) . . ?
C23 C22 H22 118.7 . . ?
C21 C22 H22 118.7 . . ?
C22 C23 C11 119.08(8) . . ?
C22 C23 C24 121.83(8) . . ?
C11 C23 C24 119.09(8) . . ?
C1 C24 C5 118.78(8) . . ?
C1 C24 C23 121.90(8) . . ?
C5 C24 C23 119.32(8) . . ?

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
C24 C1 C2 C3 -0.43(14) . . . . ?
C1 C2 C3 C4 0.06(14) . . . . ?
C2 C3 C4 C6 -176.86(9) . . . . ?
C2 C3 C4 C5 1.37(13) . . . . ?
C3 C4 C5 C24 -2.43(12) . . . . ?
C6 C4 C5 C24 175.84(8) . . . . ?
C3 C4 C5 C9 178.55(8) . . . . ?
C6 C4 C5 C9 -3.18(13) . . . . ?
C3 C4 C6 C7 177.08(9) . . . . ?
C5 C4 C6 C7 -1.15(14) . . . . ?
C4 C6 C7 C8 3.34(15) . . . . ?
C6 C7 C8 C9 -1.13(15) . . . . ?
C7 C8 C9 C5 -3.22(14) . . . . ?
C7 C8 C9 C10 176.67(8) . . . . ?
C24 C5 C9 C8 -173.71(8) . . . . ?
C4 C5 C9 C8 5.30(12) . . . . ?
C24 C5 C9 C10 6.40(12) . . . . ?
C4 C5 C9 C10 -174.60(7) . . . . ?
C8 C9 C10 C12 -9.70(13) . . . . ?
C5 C9 C10 C12 170.19(8) . . . . ?
C8 C9 C10 C11 170.99(8) . . . . ?
C5 C9 C10 C11 -9.12(12) . . . . ?
C12 C10 C11 C15 3.99(13) . . . . ?
C9 C10 C11 C15 -176.68(7) . . . . ?
C12 C10 C11 C23 -175.43(7) . . . . ?
C9 C10 C11 C23 3.90(12) . . . . ?
C11 C10 C12 C13 -3.48(13) . . . . ?
C9 C10 C12 C13 177.20(8) . . . . ?
C10 C12 C13 C14 0.34(14) . . . . ?
C12 C13 C14 C15 2.32(14) . . . . ?
C13 C14 C15 C11 -1.72(13) . . . . ?
C13 C14 C15 C16 177.34(8) . . . . ?
C10 C11 C15 C14 -1.45(12) . . . . ?
C23 C11 C15 C14 177.98(7) . . . . ?
C10 C11 C15 C16 179.48(7) . . . . ?
C23 C11 C15 C16 -1.10(12) . . . . ?
C14 C15 C16 C17 -1.74(13) . . . . ?
C11 C15 C16 C17 177.31(7) . . . . ?
C14 C15 C16 C21 178.84(8) . . . . ?
C11 C15 C16 C21 -2.11(12) . . . . ?
C21 C16 C17 C18 -0.68(13) . . . . ?
C15 C16 C17 C18 179.90(8) . . . . ?
C16 C17 C18 C19 0.04(14) . . . . ?
C17 C18 C19 C20 0.22(15) . . . . ?
C18 C19 C20 C21 0.19(15) . . . . ?
C19 C20 C21 C16 -0.85(14) . . . . ?
C19 C20 C21 C22 176.96(8) . . . . ?
C17 C16 C21 C20 1.08(13) . . . . ?
C15 C16 C21 C20 -179.48(8) . . . . ?
C17 C16 C21 C22 -176.75(7) . . . . ?
C15 C16 C21 C22 2.69(13) . . . . ?
C20 C21 C22 C23 -177.79(8) . . . . ?
C16 C21 C22 C23 0.02(13) . . . . ?
C21 C22 C23 C11 -3.27(13) . . . . ?
C21 C22 C23 C24 175.96(7) . . . . ?
C10 C11 C23 C22 -176.81(8) . . . . ?
C15 C11 C23 C22 3.77(12) . . . . ?
C10 C11 C23 C24 3.94(12) . . . . ?
C15 C11 C23 C24 -175.48(7) . . . . ?
C2 C1 C24 C5 -0.66(13) . . . . ?
C2 C1 C24 C23 178.97(8) . . . . ?
C9 C5 C24 C1 -178.93(8) . . . . ?
C4 C5 C24 C1 2.07(12) . . . . ?
C9 C5 C24 C23 1.44(12) . . . . ?
C4 C5 C24 C23 -177.56(7) . . . . ?
C22 C23 C24 C1 -5.52(13) . . . . ?
C11 C23 C24 C1 173.70(8) . . . . ?
C22 C23 C24 C5 174.10(8) . . . . ?
C11 C23 C24 C5 -6.68(12) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_861_MX65_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2022134'
loop_
_audit_author_name
_audit_author_address
'Kazutaka Shoyama'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2020-08-11 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        phenaleno[1,2,3-de]quinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 N'
_chemical_formula_sum            'C19 H11 N'
_chemical_formula_weight         253.29

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'
N N 0.0311 0.0180 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.4216(3)
_cell_length_b                   10.5958(3)
_cell_length_c                   11.0003(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.8153(18)
_cell_angle_gamma                90
_cell_volume                     1168.73(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3469
_cell_measurement_theta_min      5.91
_cell_measurement_theta_max      67.96

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.646
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12158
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.409
_diffrn_reflns_theta_max         68.257
_diffrn_reflns_theta_full        67.684
_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             2140
_reflns_number_gt                1517
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.1600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     200
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.049
_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
N1 N 0.8935(11) 0.7333(7) 0.6283(7) 0.0365(17) Uani 0.490(14) 1 d D . P A 1
C1 C 0.68975(17) 0.82655(14) 0.51699(15) 0.0381(4) Uani 1 1 d D . . . .
H1 H 0.645775 0.892376 0.462838 0.046 Uiso 1 1 calc R U . . .
C2 C 0.82917(17) 0.82188(14) 0.55345(16) 0.0416(4) Uani 1 1 d D . . . .
H2 H 0.878113 0.884387 0.523155 0.050 Uiso 1 1 calc R U . A 1
C3 C 0.82721(16) 0.63868(14) 0.67400(14) 0.0367(3) Uani 1 1 d D . . . .
C4 C 0.68530(15) 0.63958(13) 0.63956(13) 0.0315(3) Uani 1 1 d D . . . .
C5 C 0.9049(14) 0.5436(12) 0.7489(14) 0.0390(17) Uani 0.490(14) 1 d D . P A 1
H5 H 0.999430 0.541260 0.767831 0.047 Uiso 0.490(14) 1 calc R U P A 1
C6 C 0.83191(17) 0.45430(15) 0.79250(15) 0.0426(4) Uani 1 1 d D . . . .
H6 H 0.879749 0.391075 0.847846 0.051 Uiso 1 1 calc R U . A 1
C7 C 0.69277(16) 0.45004(14) 0.76117(14) 0.0370(4) Uani 1 1 d D . . . .
H7 H 0.650047 0.383400 0.792817 0.044 Uiso 1 1 calc R U . . .
C8 C 0.61636(15) 0.54117(13) 0.68491(13) 0.0312(3) Uani 1 1 d . . . . .
C9 C 0.46990(15) 0.54165(12) 0.64946(13) 0.0300(3) Uani 1 1 d . . . . .
C10 C 0.39915(15) 0.64109(13) 0.57149(13) 0.0309(3) Uani 1 1 d . . . . .
C11 C 0.39754(16) 0.44848(13) 0.68908(14) 0.0337(4) Uani 1 1 d . . . . .
H11 H 0.443706 0.381000 0.739250 0.040 Uiso 1 1 calc R U . . .
C12 C 0.25798(16) 0.45101(14) 0.65718(14) 0.0368(4) Uani 1 1 d . . . . .
H12 H 0.211137 0.386189 0.686762 0.044 Uiso 1 1 calc R U . . .
C13 C 0.18881(16) 0.54568(14) 0.58407(14) 0.0365(4) Uani 1 1 d . . . . .
H13 H 0.094172 0.546857 0.563523 0.044 Uiso 1 1 calc R U . . .
C14 C 0.25732(16) 0.64216(14) 0.53869(14) 0.0344(4) Uani 1 1 d . . . . .
C15 C 0.18654(17) 0.73897(15) 0.45932(14) 0.0386(4) Uani 1 1 d . . . . .
H15 H 0.091845 0.740474 0.437261 0.046 Uiso 1 1 calc R U . . .
C16 C 0.25452(18) 0.83033(15) 0.41441(15) 0.0416(4) Uani 1 1 d . . . . .
H16 H 0.206381 0.894806 0.361052 0.050 Uiso 1 1 calc R U . . .
C17 C 0.39352(17) 0.82998(14) 0.44597(14) 0.0375(4) Uani 1 1 d . . . . .
H17 H 0.438256 0.894393 0.413407 0.045 Uiso 1 1 calc R U . . .
C18 C 0.46798(16) 0.73810(13) 0.52360(13) 0.0327(4) Uani 1 1 d . . . . .
C19 C 0.61476(15) 0.73681(13) 0.55851(13) 0.0320(4) Uani 1 1 d . . . . .
N2 N 0.8968(11) 0.5460(10) 0.7551(12) 0.044(2) Uani 0.510(14) 1 d D . P A 2
C20 C 0.9043(15) 0.7302(10) 0.6316(9) 0.048(3) Uani 0.510(14) 1 d D . P A 2
H20 H 0.998987 0.728959 0.654691 0.057 Uiso 0.510(14) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.307(9) . ?
N1 C3 1.387(10) . ?
C1 C19 1.385(2) . ?
C1 C2 1.399(2) . ?
C1 H1 0.9500 . ?
C2 C20 1.389(12) . ?
C2 H2 0.9500 . ?
C3 N2 1.391(10) . ?
C3 C5 1.409(12) . ?
C3 C20 1.416(13) . ?
C3 C4 1.423(2) . ?
C4 C19 1.428(2) . ?
C4 C8 1.431(2) . ?
C5 C6 1.380(12) . ?
C5 H5 0.9500 . ?
C6 N2 1.313(9) . ?
C6 C7 1.397(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.469(2) . ?
C9 C11 1.383(2) . ?
C9 C10 1.430(2) . ?
C10 C14 1.423(2) . ?
C10 C18 1.433(2) . ?
C11 C12 1.400(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.363(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.414(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(2) . ?
C15 C16 1.369(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.472(2) . ?
C20 H20 0.9500 . ?

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 N1 C3 121.8(8) . . ?
C19 C1 C2 121.10(15) . . ?
C19 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
N1 C2 C1 121.4(5) . . ?
C20 C2 C1 124.6(6) . . ?
N1 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N1 C3 C5 117.7(5) . . ?
N2 C3 C20 116.8(5) . . ?
N1 C3 C4 118.9(5) . . ?
N2 C3 C4 119.9(4) . . ?
C5 C3 C4 123.4(5) . . ?
C20 C3 C4 123.3(6) . . ?
C3 C4 C19 119.46(14) . . ?
C3 C4 C8 119.10(14) . . ?
C19 C4 C8 121.42(14) . . ?
C6 C5 C3 114.2(10) . . ?
C6 C5 H5 122.9 . . ?
C3 C5 H5 122.9 . . ?
N2 C6 C7 122.4(5) . . ?
C5 C6 C7 124.8(6) . . ?
C5 C6 H6 117.6 . . ?
C7 C6 H6 117.6 . . ?
C8 C7 C6 121.03(14) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C4 117.40(15) . . ?
C7 C8 C9 123.32(13) . . ?
C4 C8 C9 119.28(13) . . ?
C11 C9 C10 118.60(14) . . ?
C11 C9 C8 122.03(14) . . ?
C10 C9 C8 119.37(13) . . ?
C14 C10 C9 119.22(13) . . ?
C14 C10 C18 119.37(14) . . ?
C9 C10 C18 121.39(14) . . ?
C9 C11 C12 121.72(14) . . ?
C9 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 120.55(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.26(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.86(15) . . ?
C13 C14 C10 119.64(14) . . ?
C15 C14 C10 119.50(14) . . ?
C16 C15 C14 120.04(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.86(15) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 121.65(15) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C10 118.57(15) . . ?
C17 C18 C19 122.35(14) . . ?
C10 C18 C19 119.08(13) . . ?
C1 C19 C4 117.41(15) . . ?
C1 C19 C18 123.18(14) . . ?
C4 C19 C18 119.41(13) . . ?
C6 N2 C3 120.0(8) . . ?
C2 C20 C3 114.1(10) . . ?
C2 C20 H20 123.0 . . ?
C3 C20 H20 123.0 . . ?

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
C3 N1 C2 C1 0.9(7) . . . . ?
C19 C1 C2 N1 -0.4(4) . . . . ?
C19 C1 C2 C20 0.2(4) . . . . ?
C2 N1 C3 C5 176.8(8) . . . . ?
C2 N1 C3 C4 -0.9(6) . . . . ?
N1 C3 C4 C19 0.4(3) . . . . ?
N2 C3 C4 C19 178.6(7) . . . . ?
C5 C3 C4 C19 -177.2(8) . . . . ?
C20 C3 C4 C19 -0.1(4) . . . . ?
N1 C3 C4 C8 179.1(3) . . . . ?
N2 C3 C4 C8 -2.8(7) . . . . ?
C5 C3 C4 C8 1.5(8) . . . . ?
C20 C3 C4 C8 178.5(4) . . . . ?
N1 C3 C5 C6 178.9(7) . . . . ?
C4 C3 C5 C6 -3.4(15) . . . . ?
C3 C5 C6 C7 3.9(15) . . . . ?
N2 C6 C7 C8 2.2(8) . . . . ?
C5 C6 C7 C8 -2.3(9) . . . . ?
C6 C7 C8 C4 0.0(2) . . . . ?
C6 C7 C8 C9 -179.71(14) . . . . ?
C3 C4 C8 C7 0.3(2) . . . . ?
C19 C4 C8 C7 178.98(13) . . . . ?
C3 C4 C8 C9 -179.93(12) . . . . ?
C19 C4 C8 C9 -1.3(2) . . . . ?
C7 C8 C9 C11 -1.0(2) . . . . ?
C4 C8 C9 C11 179.27(12) . . . . ?
C7 C8 C9 C10 179.07(13) . . . . ?
C4 C8 C9 C10 -0.66(19) . . . . ?
C11 C9 C10 C14 0.88(19) . . . . ?
C8 C9 C10 C14 -179.19(12) . . . . ?
C11 C9 C10 C18 -177.80(12) . . . . ?
C8 C9 C10 C18 2.13(19) . . . . ?
C10 C9 C11 C12 -1.5(2) . . . . ?
C8 C9 C11 C12 178.59(13) . . . . ?
C9 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 C13 C14 C15 178.00(13) . . . . ?
C12 C13 C14 C10 -1.0(2) . . . . ?
C9 C10 C14 C13 0.4(2) . . . . ?
C18 C10 C14 C13 179.06(12) . . . . ?
C9 C10 C14 C15 -178.70(12) . . . . ?
C18 C10 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 -178.82(14) . . . . ?
C10 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C17 C18 C10 0.3(2) . . . . ?
C16 C17 C18 C19 -179.60(13) . . . . ?
C14 C10 C18 C17 -0.3(2) . . . . ?
C9 C10 C18 C17 178.39(12) . . . . ?
C14 C10 C18 C19 179.66(12) . . . . ?
C9 C10 C18 C19 -1.66(19) . . . . ?
C2 C1 C19 C4 -0.1(2) . . . . ?
C2 C1 C19 C18 179.55(13) . . . . ?
C3 C4 C19 C1 0.1(2) . . . . ?
C8 C4 C19 C1 -178.58(13) . . . . ?
C3 C4 C19 C18 -179.61(12) . . . . ?
C8 C4 C19 C18 1.7(2) . . . . ?
C17 C18 C19 C1 0.0(2) . . . . ?
C10 C18 C19 C1 -179.93(13) . . . . ?
C17 C18 C19 C4 179.66(13) . . . . ?
C10 C18 C19 C4 -0.28(19) . . . . ?
C7 C6 N2 C3 -4.7(15) . . . . ?
C20 C3 N2 C6 -176.2(8) . . . . ?
C4 C3 N2 C6 5.0(14) . . . . ?
C1 C2 C20 C3 -0.3(7) . . . . ?
N2 C3 C20 C2 -178.5(7) . . . . ?
C4 C3 C20 C2 0.2(7) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_732_BPW174_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2022136'
loop_
_audit_author_name
_audit_author_address
'Kazutaka Shoyama'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1,2-dihydrocyclopenta[lm]naphtho[8,1,2-bcd]perylene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H16'
_chemical_formula_sum            'C28 H16'
_chemical_formula_weight         352.41

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'

_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                   7.9509(3)
_cell_length_b                   7.8333(3)
_cell_length_c                   26.1238(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.897(2)
_cell_angle_gamma                90
_cell_volume                     1623.27(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      72.08

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.143
_exptl_absorpt_coefficient_mu    0.623
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6783
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22186
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.391
_diffrn_reflns_theta_max         72.343
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3192
_reflns_number_gt                2933
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.3644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3192
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.85334(13) 0.41254(13) 0.68003(4) 0.0209(2) Uani 1 1 d . . . . .
H1 H 0.958096 0.390561 0.665849 0.025 Uiso 1 1 calc R U . . .
C2 C 0.83080(14) 0.36588(13) 0.73044(4) 0.0226(2) Uani 1 1 d . . . . .
H2 H 0.920983 0.314683 0.750660 0.027 Uiso 1 1 calc R U . . .
C3 C 0.67712(14) 0.39366(13) 0.75147(4) 0.0224(2) Uani 1 1 d . . . . .
H3 H 0.662886 0.359525 0.785806 0.027 Uiso 1 1 calc R U . . .
C4 C 0.54309(14) 0.47124(12) 0.72274(4) 0.0197(2) Uani 1 1 d . . . . .
C5 C 0.56593(13) 0.52264(12) 0.67116(4) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.72294(13) 0.49178(12) 0.64985(4) 0.0181(2) Uani 1 1 d . . . . .
C7 C 0.38368(14) 0.50473(13) 0.74341(4) 0.0224(2) Uani 1 1 d . . . . .
H7 H 0.366584 0.471371 0.777627 0.027 Uiso 1 1 calc R U . . .
C8 C 0.25770(13) 0.58262(13) 0.71520(4) 0.0215(2) Uani 1 1 d . . . . .
H8 H 0.154017 0.603694 0.730126 0.026 Uiso 1 1 calc R U . . .
C9 C 0.27647(13) 0.63477(13) 0.66291(4) 0.0185(2) Uani 1 1 d . . . . .
C10 C 0.43312(13) 0.60423(12) 0.64097(4) 0.0171(2) Uani 1 1 d . . . . .
C11 C 0.14665(13) 0.71405(13) 0.63297(4) 0.0204(2) Uani 1 1 d . . . . .
H11 H 0.041355 0.733702 0.647089 0.024 Uiso 1 1 calc R U . . .
C12 C 0.16886(13) 0.76432(13) 0.58321(4) 0.0197(2) Uani 1 1 d . . . . .
H12 H 0.078226 0.817863 0.563807 0.024 Uiso 1 1 calc R U . . .
C13 C 0.32221(13) 0.73826(12) 0.56052(4) 0.0172(2) Uani 1 1 d . . . . .
C14 C 0.45643(12) 0.65641(12) 0.58937(4) 0.0165(2) Uani 1 1 d . . . . .
C15 C 0.61805(12) 0.62369(12) 0.56846(4) 0.0166(2) Uani 1 1 d . . . . .
C16 C 0.74301(12) 0.54384(13) 0.59825(4) 0.0183(2) Uani 1 1 d . . . . .
H16 H 0.847594 0.522186 0.583926 0.022 Uiso 1 1 calc R U . . .
C17 C 0.34598(13) 0.79292(12) 0.50754(4) 0.0178(2) Uani 1 1 d . . . . .
C18 C 0.50495(13) 0.76008(12) 0.48767(4) 0.0172(2) Uani 1 1 d . . . . .
C19 C 0.64204(13) 0.67821(12) 0.51543(4) 0.0170(2) Uani 1 1 d . . . . .
C20 C 0.22306(13) 0.87377(13) 0.47569(4) 0.0216(2) Uani 1 1 d . . . . .
H20 H 0.116535 0.896040 0.488704 0.026 Uiso 1 1 calc R U . . .
C21 C 0.24936(14) 0.92449(13) 0.42469(4) 0.0231(2) Uani 1 1 d . . . . .
H21 H 0.161956 0.979361 0.404248 0.028 Uiso 1 1 calc R U . . .
C22 C 0.40258(14) 0.89337(13) 0.40523(4) 0.0211(2) Uani 1 1 d . . . . .
C23 C 0.52802(13) 0.81205(12) 0.43715(4) 0.0185(2) Uani 1 1 d . . . . .
C24 C 0.67820(14) 0.78724(13) 0.41288(4) 0.0206(2) Uani 1 1 d . . . . .
C25 C 0.81081(13) 0.70918(14) 0.44009(4) 0.0218(2) Uani 1 1 d . . . . .
H25 H 0.914639 0.691669 0.424889 0.026 Uiso 1 1 calc R U . . .
C26 C 0.79084(13) 0.65520(13) 0.49101(4) 0.0199(2) Uani 1 1 d . . . . .
H26 H 0.883105 0.600771 0.509386 0.024 Uiso 1 1 calc R U . . .
C27 C 0.47221(15) 0.92750(13) 0.35366(4) 0.0244(3) Uani 1 1 d . . . . .
H27A H 0.471584 1.051317 0.346056 0.029 Uiso 1 1 calc R U . . .
H27B H 0.404742 0.867543 0.325938 0.029 Uiso 1 1 calc R U . . .
C28 C 0.65590(14) 0.85747(14) 0.35880(4) 0.0240(2) Uani 1 1 d . . . . .
H28A H 0.671355 0.766384 0.333269 0.029 Uiso 1 1 calc R U . . .
H28B H 0.738061 0.949859 0.353697 0.029 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3900(14) . ?
C1 C6 1.4039(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.3905(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3999(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.4298(13) . ?
C4 C7 1.4352(15) . ?
C5 C6 1.4216(14) . ?
C5 C10 1.4256(14) . ?
C6 C16 1.4276(14) . ?
C7 C8 1.3483(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4433(14) . ?
C8 H8 0.9500 . ?
C9 C11 1.3975(15) . ?
C9 C10 1.4263(14) . ?
C10 C14 1.4327(13) . ?
C11 C12 1.3811(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.4063(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.4172(14) . ?
C13 C17 1.4733(14) . ?
C14 C15 1.4528(14) . ?
C15 C16 1.3707(14) . ?
C15 C19 1.4745(13) . ?
C16 H16 0.9500 . ?
C17 C20 1.3921(14) . ?
C17 C18 1.4220(14) . ?
C18 C23 1.4050(14) . ?
C18 C19 1.4205(14) . ?
C19 C26 1.3936(14) . ?
C20 C21 1.4192(14) . ?
C20 H20 0.9500 . ?
C21 C22 1.3734(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.4081(15) . ?
C22 C27 1.5147(14) . ?
C23 C24 1.4030(15) . ?
C24 C25 1.3744(16) . ?
C24 C28 1.5153(13) . ?
C25 C26 1.4150(14) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.5573(16) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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 120.69(10) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.44(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.89(9) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.13(10) . . ?
C3 C4 C7 122.49(9) . . ?
C5 C4 C7 118.36(10) . . ?
C6 C5 C10 119.79(9) . . ?
C6 C5 C4 119.49(9) . . ?
C10 C5 C4 120.72(9) . . ?
C1 C6 C5 119.34(9) . . ?
C1 C6 C16 122.06(9) . . ?
C5 C6 C16 118.60(9) . . ?
C8 C7 C4 121.29(9) . . ?
C8 C7 H7 119.4 . . ?
C4 C7 H7 119.4 . . ?
C7 C8 C9 121.64(9) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C11 C9 C10 118.79(9) . . ?
C11 C9 C8 122.38(9) . . ?
C10 C9 C8 118.83(9) . . ?
C5 C10 C9 119.15(9) . . ?
C5 C10 C14 120.67(9) . . ?
C9 C10 C14 120.17(9) . . ?
C12 C11 C9 121.11(9) . . ?
C12 C11 H11 119.4 . . ?
C9 C11 H11 119.4 . . ?
C11 C12 C13 121.69(10) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C14 118.99(9) . . ?
C12 C13 C17 121.60(9) . . ?
C14 C13 C17 119.41(9) . . ?
C13 C14 C10 119.24(9) . . ?
C13 C14 C15 122.22(9) . . ?
C10 C14 C15 118.53(9) . . ?
C16 C15 C14 119.52(9) . . ?
C16 C15 C19 122.04(9) . . ?
C14 C15 C19 118.45(9) . . ?
C15 C16 C6 122.90(9) . . ?
C15 C16 H16 118.6 . . ?
C6 C16 H16 118.6 . . ?
C20 C17 C18 118.00(9) . . ?
C20 C17 C13 124.34(9) . . ?
C18 C17 C13 117.66(9) . . ?
C23 C18 C19 117.76(9) . . ?
C23 C18 C17 117.80(9) . . ?
C19 C18 C17 124.44(9) . . ?
C26 C19 C18 118.07(9) . . ?
C26 C19 C15 124.11(9) . . ?
C18 C19 C15 117.82(9) . . ?
C17 C20 C21 123.10(10) . . ?
C17 C20 H20 118.5 . . ?
C21 C20 H20 118.4 . . ?
C22 C21 C20 119.26(10) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 118.13(9) . . ?
C21 C22 C27 133.23(10) . . ?
C23 C22 C27 108.64(9) . . ?
C24 C23 C18 123.63(10) . . ?
C24 C23 C22 112.66(9) . . ?
C18 C23 C22 123.70(10) . . ?
C25 C24 C23 118.32(9) . . ?
C25 C24 C28 132.90(10) . . ?
C23 C24 C28 108.78(9) . . ?
C24 C25 C26 119.21(9) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C19 C26 C25 123.01(10) . . ?
C19 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
C22 C27 C28 104.98(8) . . ?
C22 C27 H27A 110.8 . . ?
C28 C27 H27A 110.8 . . ?
C22 C27 H27B 110.8 . . ?
C28 C27 H27B 110.8 . . ?
H27A C27 H27B 108.8 . . ?
C24 C28 C27 104.94(8) . . ?
C24 C28 H28A 110.8 . . ?
C27 C28 H28A 110.8 . . ?
C24 C28 H28B 110.8 . . ?
C27 C28 H28B 110.8 . . ?
H28A C28 H28B 108.8 . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_BPW175
_database_code_depnum_ccdc_archive 'CCDC 2022135'
loop_
_audit_author_name
_audit_author_address
'Kazutaka Shoyama'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        1,2-dihydrocyclopenta[cd]perylene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14'
_chemical_formula_sum            'C22 H14'
_chemical_formula_weight         278.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_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                   7.9860(3)
_cell_length_b                   9.7282(4)
_cell_length_c                   17.2083(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.2740(10)
_cell_angle_gamma                90
_cell_volume                     1319.43(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      4.55
_cell_measurement_theta_max      72.38

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.602
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   Cu/K(alpha)_ImuS_Microsource
_diffrn_measurement_device_type  Bruker-Kappa-D8Quest_PhotonII
_diffrn_measurement_method       omega_and_phi_scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18335
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.209
_diffrn_reflns_theta_max         72.384
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2592
_reflns_number_gt                2439
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.5141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2592
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.89880(15) 0.36322(13) 0.67272(7) 0.0230(3) Uani 1 1 d . . . . .
H1 H 1.006561 0.319660 0.678509 0.028 Uiso 1 1 calc R U . . .
C2 C 0.78553(15) 0.32660(13) 0.72097(7) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.814642 0.257422 0.759765 0.027 Uiso 1 1 calc R U . . .
C3 C 0.62483(15) 0.39183(12) 0.71308(7) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.58093(14) 0.49536(12) 0.65479(7) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.70123(14) 0.53114(12) 0.60398(7) 0.0185(3) Uani 1 1 d . . . . .
C6 C 0.85705(15) 0.46435(13) 0.61494(7) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.937764 0.488020 0.582222 0.025 Uiso 1 1 calc R U . . .
C7 C 0.50801(16) 0.35622(13) 0.76365(7) 0.0233(3) Uani 1 1 d . . . . .
H7 H 0.535701 0.285418 0.801565 0.028 Uiso 1 1 calc R U . . .
C8 C 0.35555(15) 0.42296(14) 0.75835(7) 0.0242(3) Uani 1 1 d . . . . .
H8 H 0.279061 0.399314 0.793149 0.029 Uiso 1 1 calc R U . . .
C9 C 0.31189(15) 0.52625(13) 0.70165(7) 0.0221(3) Uani 1 1 d . . . . .
H9 H 0.206583 0.572693 0.699451 0.027 Uiso 1 1 calc R U . . .
C10 C 0.41842(14) 0.56217(12) 0.64885(7) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.37107(14) 0.66629(12) 0.58718(7) 0.0181(3) Uani 1 1 d . . . . .
C12 C 0.49182(14) 0.69882(12) 0.53730(7) 0.0178(3) Uani 1 1 d . . . . .
C13 C 0.65473(14) 0.63631(12) 0.54302(7) 0.0185(3) Uani 1 1 d . . . . .
C14 C 0.21525(14) 0.73379(12) 0.57351(7) 0.0196(3) Uani 1 1 d . . . . .
H14 H 0.132837 0.710684 0.605459 0.024 Uiso 1 1 calc R U . . .
C15 C 0.17341(15) 0.83489(12) 0.51458(7) 0.0210(3) Uani 1 1 d . . . . .
H15 H 0.066163 0.879380 0.508007 0.025 Uiso 1 1 calc R U . . .
C16 C 0.29017(15) 0.86801(12) 0.46683(7) 0.0200(3) Uani 1 1 d . . . . .
C17 C 0.44672(15) 0.79829(12) 0.47889(7) 0.0194(3) Uani 1 1 d . . . . .
C18 C 0.55326(15) 0.84028(12) 0.42551(7) 0.0205(3) Uani 1 1 d . . . . .
C19 C 0.71044(15) 0.77957(13) 0.43130(7) 0.0220(3) Uani 1 1 d . . . . .
H19 H 0.785831 0.805333 0.396403 0.026 Uiso 1 1 calc R U . . .
C20 C 0.75854(15) 0.67881(13) 0.48948(7) 0.0207(3) Uani 1 1 d . . . . .
H20 H 0.867242 0.637619 0.492462 0.025 Uiso 1 1 calc R U . . .
C21 C 0.28733(15) 0.96710(13) 0.39924(7) 0.0229(3) Uani 1 1 d . . . . .
H21A H 0.273019 1.062718 0.416738 0.027 Uiso 1 1 calc R U . . .
H21B H 0.193504 0.944867 0.356100 0.027 Uiso 1 1 calc R U . . .
C22 C 0.46283(16) 0.94861(13) 0.37158(7) 0.0229(3) Uani 1 1 d . . . . .
H22A H 0.447883 0.917939 0.316033 0.028 Uiso 1 1 calc R U . . .
H22B H 0.527353 1.035916 0.376609 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3700(17) . ?
C1 C6 1.4002(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.4184(17) . ?
C2 H2 0.9500 . ?
C3 C7 1.4176(17) . ?
C3 C4 1.4248(17) . ?
C4 C10 1.4403(16) . ?
C4 C5 1.4421(16) . ?
C5 C6 1.3895(16) . ?
C5 C13 1.4695(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3699(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.4048(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3859(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4718(16) . ?
C11 C14 1.3931(16) . ?
C11 C12 1.4260(16) . ?
C12 C17 1.3999(17) . ?
C12 C13 1.4250(16) . ?
C13 C20 1.3976(16) . ?
C14 C15 1.4136(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3767(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.4080(17) . ?
C16 C21 1.5080(16) . ?
C17 C18 1.4094(16) . ?
C18 C19 1.3763(17) . ?
C18 C22 1.5091(17) . ?
C19 C20 1.4096(17) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.5615(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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 120.54(11) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.08(11) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C7 C3 C2 120.44(11) . . ?
C7 C3 C4 119.56(11) . . ?
C2 C3 C4 119.99(11) . . ?
C3 C4 C10 119.05(10) . . ?
C3 C4 C5 119.02(11) . . ?
C10 C4 C5 121.93(11) . . ?
C6 C5 C4 118.32(11) . . ?
C6 C5 C13 122.71(11) . . ?
C4 C5 C13 118.98(10) . . ?
C5 C6 C1 122.04(11) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C8 C7 C3 120.61(11) . . ?
C8 C7 H7 119.7 . . ?
C3 C7 H7 119.7 . . ?
C7 C8 C9 120.25(11) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 121.72(11) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C4 118.76(11) . . ?
C9 C10 C11 122.20(11) . . ?
C4 C10 C11 119.05(10) . . ?
C14 C11 C12 117.78(11) . . ?
C14 C11 C10 124.39(10) . . ?
C12 C11 C10 117.82(10) . . ?
C17 C12 C13 118.10(11) . . ?
C17 C12 C11 117.70(11) . . ?
C13 C12 C11 124.20(11) . . ?
C20 C13 C12 117.40(11) . . ?
C20 C13 C5 124.61(11) . . ?
C12 C13 C5 117.99(10) . . ?
C11 C14 C15 123.40(11) . . ?
C11 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C16 C15 C14 119.11(11) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 118.03(11) . . ?
C15 C16 C21 133.04(11) . . ?
C17 C16 C21 108.92(10) . . ?
C12 C17 C16 123.95(11) . . ?
C12 C17 C18 123.77(11) . . ?
C16 C17 C18 112.28(11) . . ?
C19 C18 C17 117.89(11) . . ?
C19 C18 C22 133.21(11) . . ?
C17 C18 C22 108.90(10) . . ?
C18 C19 C20 119.39(11) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C13 C20 C19 123.46(11) . . ?
C13 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
C16 C21 C22 105.00(10) . . ?
C16 C21 H21A 110.7 . . ?
C22 C21 H21A 110.7 . . ?
C16 C21 H21B 110.7 . . ?
C22 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C18 C22 C21 104.89(9) . . ?
C18 C22 H22A 110.8 . . ?
C21 C22 H22A 110.8 . . ?
C18 C22 H22B 110.8 . . ?
C21 C22 H22B 110.8 . . ?
H22A C22 H22B 108.8 . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041



