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

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

data_SPA872
_database_code_depnum_ccdc_archive 'CCDC 2282270'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        
2-(naphthalen-1-yl)-2-(10-oxoanthracen-9(10H)-ylidene)acetonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H15 N O'
_chemical_formula_sum            'C26 H15 N O'
_chemical_formula_weight         357.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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                   7.6870(15)
_cell_length_b                   16.132(3)
_cell_length_c                   14.951(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.35(3)
_cell_angle_gamma                90
_cell_volume                     1823.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    40432
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.043
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14822
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4108
_reflns_number_gt                2991
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.1400P)²+0.0232P] 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         4108
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2286
_refine_ls_wR_factor_gt          0.2170
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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 0.7999(2) 0.64146(11) 0.48644(11) 0.0808(5) Uani 1 1 d . . . . .
N1 N 0.1436(3) 0.49228(12) 0.72942(12) 0.0782(6) Uani 1 1 d . . . . .
C1 C 0.4696(2) 0.62958(10) 0.67181(11) 0.0483(4) Uani 1 1 d . . . . .
C2 C 0.6268(2) 0.68509(10) 0.68992(12) 0.0515(4) Uani 1 1 d . . . . .
C3 C 0.6648(3) 0.73487(11) 0.76729(13) 0.0579(5) Uani 1 1 d . . . . .
H3 H 0.586884 0.735492 0.809081 0.069 Uiso 1 1 calc R U . . .
C4 C 0.8153(3) 0.78320(12) 0.78320(14) 0.0666(5) Uani 1 1 d . . . . .
H4 H 0.838393 0.816812 0.835343 0.080 Uiso 1 1 calc R U . . .
C5 C 0.9318(3) 0.78253(14) 0.72328(16) 0.0725(6) Uani 1 1 d . . . . .
H5 H 1.036903 0.813525 0.735962 0.087 Uiso 1 1 calc R U . . .
C6 C 0.8941(3) 0.73631(13) 0.64460(14) 0.0654(5) Uani 1 1 d . . . . .
H6 H 0.971769 0.737091 0.602678 0.078 Uiso 1 1 calc R U . . .
C7 C 0.7404(2) 0.68828(11) 0.62725(12) 0.0547(5) Uani 1 1 d . . . . .
C8 C 0.6938(3) 0.64649(12) 0.53758(13) 0.0579(5) Uani 1 1 d . . . . .
C9 C 0.5087(2) 0.61809(11) 0.51094(12) 0.0519(4) Uani 1 1 d . . . . .
C10 C 0.4488(3) 0.59708(12) 0.42016(12) 0.0593(5) Uani 1 1 d . . . . .
H10 H 0.527227 0.597990 0.378624 0.071 Uiso 1 1 calc R U . . .
C11 C 0.2744(3) 0.57498(12) 0.39142(13) 0.0625(5) Uani 1 1 d . . . . .
H11 H 0.234321 0.559927 0.330460 0.075 Uiso 1 1 calc R U . . .
C12 C 0.1593(3) 0.57496(12) 0.45189(13) 0.0595(5) Uani 1 1 d . . . . .
H12 H 0.039555 0.561963 0.431387 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2177(2) 0.59390(11) 0.54291(12) 0.0537(4) Uani 1 1 d . . . . .
H13 H 0.137631 0.593061 0.583585 0.064 Uiso 1 1 calc R U . . .
C14 C 0.3943(2) 0.61415(10) 0.57437(11) 0.0495(4) Uani 1 1 d . . . . .
C15 C 0.4150(2) 0.58952(10) 0.74140(12) 0.0518(4) Uani 1 1 d . . . . .
C16 C 0.2634(3) 0.53566(12) 0.72973(12) 0.0600(5) Uani 1 1 d . . . . .
C17 C 0.5171(2) 0.58674(11) 0.83720(12) 0.0530(4) Uani 1 1 d . . . . .
C18 C 0.6840(3) 0.55416(12) 0.85141(13) 0.0612(5) Uani 1 1 d . . . . .
H18 H 0.731266 0.535041 0.801409 0.073 Uiso 1 1 calc R U . . .
C19 C 0.7863(3) 0.54861(13) 0.93889(15) 0.0674(5) Uani 1 1 d . . . . .
H19 H 0.901509 0.526831 0.947075 0.081 Uiso 1 1 calc R U . . .
C20 C 0.7180(3) 0.57491(13) 1.01184(14) 0.0664(5) Uani 1 1 d . . . . .
H20 H 0.786353 0.570637 1.070463 0.080 Uiso 1 1 calc R U . . .
C21 C 0.5445(3) 0.60881(11) 1.00065(12) 0.0565(5) Uani 1 1 d . . . . .
C22 C 0.4716(3) 0.63659(13) 1.07546(14) 0.0680(6) Uani 1 1 d . . . . .
H22 H 0.536620 0.630608 1.134659 0.082 Uiso 1 1 calc R U . . .
C23 C 0.3085(3) 0.67187(14) 1.06295(15) 0.0738(6) Uani 1 1 d . . . . .
H23 H 0.262264 0.690609 1.113436 0.089 Uiso 1 1 calc R U . . .
C24 C 0.2084(3) 0.68055(13) 0.97506(15) 0.0692(6) Uani 1 1 d . . . . .
H24 H 0.096468 0.705762 0.967084 0.083 Uiso 1 1 calc R U . . .
C25 C 0.2724(3) 0.65273(12) 0.90147(14) 0.0610(5) Uani 1 1 d . . . . .
H25 H 0.203297 0.658222 0.843171 0.073 Uiso 1 1 calc R U . . .
C26 C 0.4433(2) 0.61526(11) 0.91150(12) 0.0533(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.217(2) . ?
N1 C16 1.156(3) . ?
C1 C15 1.354(2) . ?
C1 C14 1.489(2) . ?
C1 C2 1.489(2) . ?
C2 C7 1.392(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.398(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.486(3) . ?
C8 C9 1.480(3) . ?
C9 C10 1.394(2) . ?
C9 C14 1.406(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.388(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.393(2) . ?
C13 H13 0.9400 . ?
C15 C16 1.439(3) . ?
C15 C17 1.505(2) . ?
C17 C18 1.367(3) . ?
C17 C26 1.412(3) . ?
C18 C19 1.403(3) . ?
C18 H18 0.9400 . ?
C19 C20 1.361(3) . ?
C19 H19 0.9400 . ?
C20 C21 1.423(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.411(3) . ?
C21 C26 1.421(2) . ?
C22 C23 1.359(3) . ?
C22 H22 0.9400 . ?
C23 C24 1.405(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.359(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.429(3) . ?
C25 H25 0.9400 . ?

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
C15 C1 C14 123.54(15) . . ?
C15 C1 C2 120.05(15) . . ?
C14 C1 C2 116.00(15) . . ?
C7 C2 C3 118.27(17) . . ?
C7 C2 C1 119.12(16) . . ?
C3 C2 C1 122.60(17) . . ?
C4 C3 C2 120.81(19) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.47(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.48(17) . . ?
C2 C7 C8 120.78(16) . . ?
C6 C7 C8 118.54(17) . . ?
O1 C8 C9 122.09(18) . . ?
O1 C8 C7 121.11(18) . . ?
C9 C8 C7 116.60(16) . . ?
C10 C9 C14 120.58(17) . . ?
C10 C9 C8 118.06(17) . . ?
C14 C9 C8 121.34(15) . . ?
C11 C10 C9 119.89(18) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.00(17) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.77(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 120.43(17) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 118.19(16) . . ?
C13 C14 C1 123.59(16) . . ?
C9 C14 C1 118.20(15) . . ?
C1 C15 C16 123.45(15) . . ?
C1 C15 C17 124.38(16) . . ?
C16 C15 C17 111.72(15) . . ?
N1 C16 C15 173.4(2) . . ?
C18 C17 C26 120.09(16) . . ?
C18 C17 C15 118.27(17) . . ?
C26 C17 C15 121.63(16) . . ?
C17 C18 C19 121.51(19) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 119.67(19) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.94(18) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C26 119.47(19) . . ?
C22 C21 C20 121.74(18) . . ?
C26 C21 C20 118.78(18) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.94(19) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C17 C26 C21 118.99(17) . . ?
C17 C26 C25 123.15(16) . . ?
C21 C26 C25 117.84(17) . . ?

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
C15 C1 C2 C7 143.74(17) . . . . ?
C14 C1 C2 C7 -29.2(2) . . . . ?
C15 C1 C2 C3 -36.7(2) . . . . ?
C14 C1 C2 C3 150.35(17) . . . . ?
C7 C2 C3 C4 -2.8(3) . . . . ?
C1 C2 C3 C4 177.63(16) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 3.0(3) . . . . ?
C4 C5 C6 C7 -1.9(3) . . . . ?
C3 C2 C7 C6 3.9(3) . . . . ?
C1 C2 C7 C6 -176.53(16) . . . . ?
C3 C2 C7 C8 -171.04(17) . . . . ?
C1 C2 C7 C8 8.5(2) . . . . ?
C5 C6 C7 C2 -1.6(3) . . . . ?
C5 C6 C7 C8 173.5(2) . . . . ?
C2 C7 C8 O1 -172.12(18) . . . . ?
C6 C7 C8 O1 12.8(3) . . . . ?
C2 C7 C8 C9 12.9(3) . . . . ?
C6 C7 C8 C9 -162.14(16) . . . . ?
O1 C8 C9 C10 -10.0(3) . . . . ?
C7 C8 C9 C10 164.91(17) . . . . ?
O1 C8 C9 C14 171.53(19) . . . . ?
C7 C8 C9 C14 -13.5(3) . . . . ?
C14 C9 C10 C11 2.3(3) . . . . ?
C8 C9 C10 C11 -176.22(16) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C13 -2.5(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C9 2.6(3) . . . . ?
C12 C13 C14 C1 -175.71(16) . . . . ?
C10 C9 C14 C13 -4.0(3) . . . . ?
C8 C9 C14 C13 174.41(16) . . . . ?
C10 C9 C14 C1 174.36(16) . . . . ?
C8 C9 C14 C1 -7.2(2) . . . . ?
C15 C1 C14 C13 34.0(3) . . . . ?
C2 C1 C14 C13 -153.39(16) . . . . ?
C15 C1 C14 C9 -144.32(18) . . . . ?
C2 C1 C14 C9 28.3(2) . . . . ?
C14 C1 C15 C16 -8.4(3) . . . . ?
C2 C1 C15 C16 179.27(17) . . . . ?
C14 C1 C15 C17 163.26(16) . . . . ?
C2 C1 C15 C17 -9.1(3) . . . . ?
C1 C15 C17 C18 -58.8(2) . . . . ?
C16 C15 C17 C18 113.65(19) . . . . ?
C1 C15 C17 C26 122.4(2) . . . . ?
C16 C15 C17 C26 -65.1(2) . . . . ?
C26 C17 C18 C19 -0.4(3) . . . . ?
C15 C17 C18 C19 -179.23(18) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C21 -0.6(3) . . . . ?
C19 C20 C21 C22 -179.84(18) . . . . ?
C19 C20 C21 C26 -0.4(3) . . . . ?
C26 C21 C22 C23 -2.2(3) . . . . ?
C20 C21 C22 C23 177.28(18) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
C18 C17 C26 C21 -0.5(3) . . . . ?
C15 C17 C26 C21 178.20(16) . . . . ?
C18 C17 C26 C25 177.67(17) . . . . ?
C15 C17 C26 C25 -3.6(3) . . . . ?
C22 C21 C26 C17 -179.56(16) . . . . ?
C20 C21 C26 C17 0.9(2) . . . . ?
C22 C21 C26 C25 2.1(3) . . . . ?
C20 C21 C26 C25 -177.37(16) . . . . ?
C24 C25 C26 C17 -178.83(18) . . . . ?
C24 C25 C26 C21 -0.6(3) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.051

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

data_SPA873
_database_code_depnum_ccdc_archive 'CCDC 2282272'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        
(Z)-3-(anthracen-9-yl)-2-(naphthalen-2-yl)acrylonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H33 Cl N2'
_chemical_formula_sum            'C54 H33 Cl N2'
_chemical_formula_weight         745.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1456 0.1550 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   16.899(3)
_cell_length_b                   5.5020(11)
_cell_length_c                   41.337(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3843.4(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    78736
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.071
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25422
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         1.941
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             7495
_reflns_number_gt                6006
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.963
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.946

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(11)
_chemical_absolute_configuration .
_refine_ls_number_reflns         7495
_refine_ls_number_parameters     526
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1112
_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
Cl1A Cl 0.48174(16) 0.3065(5) 0.51197(5) 0.0861(11) Uani 0.402(4) 1 d . . P A 1
C8A1 C 0.4618(2) 0.1433(8) 0.54568(8) 0.0801(11) Uani 0.402(4) 1 d . . P A 1
C8A2 C 0.4618(2) 0.1433(8) 0.54568(8) 0.0801(11) Uani 0.598(4) 1 d . . P A 2
H8CA H 0.466667 0.241017 0.527127 0.096 Uiso 0.598(4) 1 calc R U P A 2
N1A N 0.60484(19) 0.0432(7) 0.65352(8) 0.0842(9) Uani 1 1 d . . . . .
C1A C 0.44967(18) -0.1420(6) 0.60127(7) 0.0594(8) Uani 1 1 d . . . . .
C2A C 0.5106(2) -0.1883(7) 0.57908(8) 0.0677(9) Uani 1 1 d . . . . .
C3A C 0.5662(2) -0.3827(8) 0.58336(10) 0.0804(11) Uani 1 1 d . . . . .
H3A H 0.562585 -0.483899 0.601615 0.097 Uiso 1 1 calc R U . . .
C4A C 0.6243(3) -0.4212(11) 0.56104(13) 0.1042(15) Uani 1 1 d . . . . .
H4A H 0.660446 -0.548891 0.564165 0.125 Uiso 1 1 calc R U . . .
C5A C 0.6310(3) -0.2735(15) 0.53347(14) 0.116(2) Uani 1 1 d . . . . .
H5A H 0.671460 -0.303229 0.518377 0.139 Uiso 1 1 calc R U . . .
C6A C 0.5800(3) -0.0902(12) 0.52852(10) 0.1049(17) Uani 1 1 d . . . . .
H6A H 0.585786 0.008366 0.510105 0.126 Uiso 1 1 calc R U . . .
C7A C 0.5171(2) -0.0420(8) 0.55067(8) 0.0767(11) Uani 1 1 d . . . . .
C9A C 0.4000(2) 0.1891(8) 0.56702(8) 0.0684(9) Uani 1 1 d . . . . .
C10A C 0.3439(3) 0.3798(8) 0.56227(10) 0.0841(12) Uani 1 1 d . . . . .
H10A H 0.348617 0.480941 0.544043 0.101 Uiso 1 1 calc R U . . .
C11A C 0.2841(3) 0.4181(9) 0.58347(12) 0.0912(12) Uani 1 1 d . . . . .
H11A H 0.247512 0.543602 0.579676 0.109 Uiso 1 1 calc R U . . .
C12A C 0.2764(2) 0.2719(9) 0.61100(11) 0.0826(11) Uani 1 1 d . . . . .
H12A H 0.234660 0.299544 0.625574 0.099 Uiso 1 1 calc R U . . .
C13A C 0.32914(19) 0.0899(7) 0.61678(9) 0.0678(9) Uani 1 1 d . . . . .
H13A H 0.323234 -0.006291 0.635417 0.081 Uiso 1 1 calc R U . . .
C14A C 0.39303(19) 0.0417(6) 0.59524(7) 0.0603(8) Uani 1 1 d . . . . .
C15A C 0.44214(18) -0.2860(6) 0.63125(8) 0.0605(8) Uani 1 1 d . . . . .
H15A H 0.399964 -0.396946 0.632509 0.073 Uiso 1 1 calc R U . . .
C16A C 0.49073(16) -0.2710(6) 0.65685(7) 0.0520(7) Uani 1 1 d . . . . .
C17A C 0.55458(19) -0.0953(6) 0.65498(7) 0.0588(8) Uani 1 1 d . . . . .
C18A C 0.48267(15) -0.4093(5) 0.68708(7) 0.0497(6) Uani 1 1 d . . . . .
C19A C 0.51483(16) -0.3278(5) 0.71557(7) 0.0498(6) Uani 1 1 d . . . . .
H19A H 0.544265 -0.182806 0.715503 0.060 Uiso 1 1 calc R U . . .
C20A C 0.50515(16) -0.4541(5) 0.74482(7) 0.0502(6) Uani 1 1 d . . . . .
C21A C 0.53723(18) -0.3714(6) 0.77458(7) 0.0582(7) Uani 1 1 d . . . . .
H21A H 0.566032 -0.225282 0.775088 0.070 Uiso 1 1 calc R U . . .
C22A C 0.52703(18) -0.4999(7) 0.80238(8) 0.0629(8) Uani 1 1 d . . . . .
H22A H 0.548902 -0.442977 0.821868 0.076 Uiso 1 1 calc R U . . .
C23A C 0.48384(19) -0.7175(7) 0.80193(9) 0.0657(9) Uani 1 1 d . . . . .
H23A H 0.476945 -0.805354 0.821226 0.079 Uiso 1 1 calc R U . . .
C24A C 0.45188(18) -0.8030(6) 0.77409(8) 0.0597(8) Uani 1 1 d . . . . .
H24A H 0.423232 -0.949386 0.774315 0.072 Uiso 1 1 calc R U . . .
C25A C 0.46115(16) -0.6744(5) 0.74475(7) 0.0518(7) Uani 1 1 d . . . . .
C26A C 0.42922(17) -0.7573(6) 0.71510(8) 0.0571(7) Uani 1 1 d . . . . .
H26A H 0.400321 -0.903188 0.714652 0.069 Uiso 1 1 calc R U . . .
C27A C 0.43946(17) -0.6308(5) 0.68743(7) 0.0534(7) Uani 1 1 d . . . . .
H27A H 0.417624 -0.690236 0.668068 0.064 Uiso 1 1 calc R U . . .
Cl1B Cl 0.23553(10) 1.3118(4) 0.48837(4) 0.0860(8) Uani 0.587(4) 1 d . . P B 1
C8B1 C 0.2251(3) 1.1434(8) 0.45396(8) 0.0787(11) Uani 0.587(4) 1 d . . P B 1
C8B2 C 0.2251(3) 1.1434(8) 0.45396(8) 0.0787(11) Uani 0.413(4) 1 d . . P B 2
H8CB H 0.228757 1.242891 0.472387 0.094 Uiso 0.413(4) 1 calc R U P B 2
N1B N 0.3706(2) 1.0436(7) 0.34658(8) 0.0848(9) Uani 1 1 d . . . . .
C1B C 0.21597(19) 0.8526(6) 0.39901(7) 0.0606(8) Uani 1 1 d . . . . .
C2B C 0.2773(2) 0.8117(8) 0.42165(8) 0.0681(9) Uani 1 1 d . . . . .
C3B C 0.3349(2) 0.6269(8) 0.41815(9) 0.0804(11) Uani 1 1 d . . . . .
H3B H 0.332713 0.525195 0.399895 0.097 Uiso 1 1 calc R U . . .
C4B C 0.3932(3) 0.5913(10) 0.44029(12) 0.1005(14) Uani 1 1 d . . . . .
H4B H 0.430458 0.466415 0.437308 0.121 Uiso 1 1 calc R U . . .
C5B C 0.3975(3) 0.7427(12) 0.46773(13) 0.1080(18) Uani 1 1 d . . . . .
H5B H 0.438579 0.719507 0.482768 0.130 Uiso 1 1 calc R U . . .
C6B C 0.3438(3) 0.9208(12) 0.47284(11) 0.1043(17) Uani 1 1 d . . . . .
H6B H 0.347407 1.017797 0.491504 0.125 Uiso 1 1 calc R U . . .
C7B C 0.2811(2) 0.9632(8) 0.44996(8) 0.0760(10) Uani 1 1 d . . . . .
C9B C 0.1632(2) 1.1868(8) 0.43214(8) 0.0681(9) Uani 1 1 d . . . . .
C10B C 0.1059(3) 1.3765(8) 0.43555(9) 0.0827(12) Uani 1 1 d . . . . .
H10B H 0.109054 1.481641 0.453422 0.099 Uiso 1 1 calc R U . . .
C11B C 0.0476(3) 1.4081(8) 0.41385(10) 0.0850(11) Uani 1 1 d . . . . .
H11B H 0.010565 1.533387 0.416904 0.102 Uiso 1 1 calc R U . . .
C12B C 0.0414(2) 1.2562(8) 0.38661(10) 0.0764(11) Uani 1 1 d . . . . .
H12B H -0.000146 1.278486 0.371783 0.092 Uiso 1 1 calc R U . . .
C13B C 0.09552(19) 1.0770(7) 0.38175(8) 0.0656(8) Uani 1 1 d . . . . .
H13B H 0.091227 0.978135 0.363288 0.079 Uiso 1 1 calc R U . . .
C14B C 0.1591(2) 1.0352(6) 0.40413(7) 0.0616(8) Uani 1 1 d . . . . .
C15B C 0.21069(18) 0.7051(7) 0.36915(8) 0.0608(8) Uani 1 1 d . . . . .
H15B H 0.170179 0.588302 0.368051 0.073 Uiso 1 1 calc R U . . .
C16B C 0.25882(16) 0.7244(5) 0.34363(8) 0.0516(7) Uani 1 1 d . . . . .
C17B C 0.32125(19) 0.9030(6) 0.34539(7) 0.0591(7) Uani 1 1 d . . . . .
C18B C 0.25089(16) 0.5866(5) 0.31317(7) 0.0503(6) Uani 1 1 d . . . . .
C19B C 0.28270(17) 0.6715(6) 0.28475(7) 0.0516(7) Uani 1 1 d . . . . .
H19B H 0.311979 0.816769 0.284993 0.062 Uiso 1 1 calc R U . . .
C20B C 0.27264(16) 0.5467(5) 0.25521(7) 0.0504(6) Uani 1 1 d . . . . .
C21B C 0.30439(17) 0.6317(6) 0.22572(7) 0.0573(7) Uani 1 1 d . . . . .
H21B H 0.333395 0.777429 0.225487 0.069 Uiso 1 1 calc R U . . .
C22B C 0.29389(18) 0.5068(7) 0.19762(8) 0.0641(8) Uani 1 1 d . . . . .
H22B H 0.315334 0.567349 0.178248 0.077 Uiso 1 1 calc R U . . .
C23B C 0.25122(19) 0.2884(7) 0.19746(8) 0.0652(9) Uani 1 1 d . . . . .
H23B H 0.244487 0.202091 0.178027 0.078 Uiso 1 1 calc R U . . .
C24B C 0.21922(18) 0.2001(7) 0.22567(8) 0.0611(8) Uani 1 1 d . . . . .
H24B H 0.190395 0.054035 0.225404 0.073 Uiso 1 1 calc R U . . .
C25B C 0.22923(17) 0.3264(5) 0.25487(7) 0.0515(6) Uani 1 1 d . . . . .
C26B C 0.19775(17) 0.2410(6) 0.28480(8) 0.0570(7) Uani 1 1 d . . . . .
H26B H 0.168928 0.094913 0.285089 0.068 Uiso 1 1 calc R U . . .
C27B C 0.20814(17) 0.3638(5) 0.31266(7) 0.0539(7) Uani 1 1 d . . . . .
H27B H 0.186930 0.301572 0.331978 0.065 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
Cl1A C8A1 1.692(4) . ?
C8A1 C9A 1.391(6) . ?
C8A1 C7A 1.399(6) . ?
C8A2 C9A 1.391(6) . ?
C8A2 C7A 1.399(6) . ?
C8A2 H8CA 0.9400 . ?
N1A C17A 1.143(4) . ?
C1A C2A 1.403(5) . ?
C1A C14A 1.414(5) . ?
C1A C15A 1.476(5) . ?
C2A C7A 1.428(5) . ?
C2A C3A 1.434(6) . ?
C3A C4A 1.363(6) . ?
C3A H3A 0.9400 . ?
C4A C5A 1.404(9) . ?
C4A H4A 0.9400 . ?
C5A C6A 1.342(8) . ?
C5A H5A 0.9400 . ?
C6A C7A 1.427(6) . ?
C6A H6A 0.9400 . ?
C9A C14A 1.426(5) . ?
C9A C10A 1.427(6) . ?
C10A C11A 1.355(7) . ?
C10A H10A 0.9400 . ?
C11A C12A 1.399(7) . ?
C11A H11A 0.9400 . ?
C12A C13A 1.362(5) . ?
C12A H12A 0.9400 . ?
C13A C14A 1.424(5) . ?
C13A H13A 0.9400 . ?
C15A C16A 1.342(4) . ?
C15A H15A 0.9400 . ?
C16A C17A 1.451(4) . ?
C16A C18A 1.469(4) . ?
C18A C19A 1.373(4) . ?
C18A C27A 1.420(4) . ?
C19A C20A 1.404(4) . ?
C19A H19A 0.9400 . ?
C20A C21A 1.419(4) . ?
C20A C25A 1.422(4) . ?
C21A C22A 1.360(4) . ?
C21A H21A 0.9400 . ?
C22A C23A 1.402(5) . ?
C22A H22A 0.9400 . ?
C23A C24A 1.355(5) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.413(4) . ?
C24A H24A 0.9400 . ?
C25A C26A 1.415(4) . ?
C26A C27A 1.350(5) . ?
C26A H26A 0.9400 . ?
C27A H27A 0.9400 . ?
Cl1B C8B1 1.707(4) . ?
C8B1 C7B 1.380(6) . ?
C8B1 C9B 1.402(6) . ?
C8B2 C7B 1.380(6) . ?
C8B2 C9B 1.402(6) . ?
C8B2 H8CB 0.9400 . ?
N1B C17B 1.139(4) . ?
C1B C14B 1.406(5) . ?
C1B C2B 1.415(5) . ?
C1B C15B 1.480(4) . ?
C2B C3B 1.415(6) . ?
C2B C7B 1.438(5) . ?
C3B C4B 1.359(6) . ?
C3B H3B 0.9400 . ?
C4B C5B 1.409(8) . ?
C4B H4B 0.9400 . ?
C5B C6B 1.353(8) . ?
C5B H5B 0.9400 . ?
C6B C7B 1.439(6) . ?
C6B H6B 0.9400 . ?
C9B C14B 1.429(5) . ?
C9B C10B 1.431(6) . ?
C10B C11B 1.343(6) . ?
C10B H10B 0.9400 . ?
C11B C12B 1.406(6) . ?
C11B H11B 0.9400 . ?
C12B C13B 1.360(5) . ?
C12B H12B 0.9400 . ?
C13B C14B 1.436(5) . ?
C13B H13B 0.9400 . ?
C15B C16B 1.336(5) . ?
C15B H15B 0.9400 . ?
C16B C17B 1.444(4) . ?
C16B C18B 1.476(4) . ?
C18B C19B 1.374(4) . ?
C18B C27B 1.423(4) . ?
C19B C20B 1.411(4) . ?
C19B H19B 0.9400 . ?
C20B C21B 1.412(4) . ?
C20B C25B 1.417(4) . ?
C21B C22B 1.361(5) . ?
C21B H21B 0.9400 . ?
C22B C23B 1.402(5) . ?
C22B H22B 0.9400 . ?
C23B C24B 1.374(5) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.403(4) . ?
C24B H24B 0.9400 . ?
C25B C26B 1.426(5) . ?
C26B C27B 1.346(5) . ?
C26B H26B 0.9400 . ?
C27B H27B 0.9400 . ?

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
C9A C8A1 C7A 122.7(4) . . ?
C9A C8A1 Cl1A 125.2(4) . . ?
C7A C8A1 Cl1A 112.1(3) . . ?
C9A C8A2 C7A 122.7(4) . . ?
C9A C8A2 H8CA 118.6 . . ?
C7A C8A2 H8CA 118.6 . . ?
C2A C1A C14A 120.8(3) . . ?
C2A C1A C15A 121.0(3) . . ?
C14A C1A C15A 118.3(3) . . ?
C1A C2A C7A 119.5(4) . . ?
C1A C2A C3A 122.4(3) . . ?
C7A C2A C3A 118.1(3) . . ?
C4A C3A C2A 120.3(5) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C3A C4A C5A 121.1(5) . . ?
C3A C4A H4A 119.4 . . ?
C5A C4A H4A 119.4 . . ?
C6A C5A C4A 120.4(5) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
C5A C6A C7A 121.3(5) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C8A2 C7A C6A 122.6(4) . . ?
C8A1 C7A C6A 122.6(4) . . ?
C8A2 C7A C2A 118.7(3) . . ?
C8A1 C7A C2A 118.7(3) . . ?
C6A C7A C2A 118.7(4) . . ?
C8A2 C9A C14A 118.5(4) . . ?
C8A1 C9A C14A 118.5(4) . . ?
C8A2 C9A C10A 123.0(4) . . ?
C8A1 C9A C10A 123.0(4) . . ?
C14A C9A C10A 118.4(4) . . ?
C11A C10A C9A 121.4(4) . . ?
C11A C10A H10A 119.3 . . ?
C9A C10A H10A 119.3 . . ?
C10A C11A C12A 120.4(4) . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A H11A 119.8 . . ?
C13A C12A C11A 120.3(4) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C12A C13A C14A 121.6(4) . . ?
C12A C13A H13A 119.2 . . ?
C14A C13A H13A 119.2 . . ?
C1A C14A C13A 122.4(3) . . ?
C1A C14A C9A 119.7(3) . . ?
C13A C14A C9A 117.9(3) . . ?
C16A C15A C1A 125.2(3) . . ?
C16A C15A H15A 117.4 . . ?
C1A C15A H15A 117.4 . . ?
C15A C16A C17A 117.0(3) . . ?
C15A C16A C18A 125.6(3) . . ?
C17A C16A C18A 117.4(3) . . ?
N1A C17A C16A 180.0(5) . . ?
C19A C18A C27A 118.4(3) . . ?
C19A C18A C16A 121.6(3) . . ?
C27A C18A C16A 120.0(2) . . ?
C18A C19A C20A 122.1(3) . . ?
C18A C19A H19A 119.0 . . ?
C20A C19A H19A 119.0 . . ?
C19A C20A C21A 122.9(3) . . ?
C19A C20A C25A 118.8(3) . . ?
C21A C20A C25A 118.3(3) . . ?
C22A C21A C20A 121.2(3) . . ?
C22A C21A H21A 119.4 . . ?
C20A C21A H21A 119.4 . . ?
C21A C22A C23A 119.9(3) . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A H22A 120.1 . . ?
C24A C23A C22A 121.0(3) . . ?
C24A C23A H23A 119.5 . . ?
C22A C23A H23A 119.5 . . ?
C23A C24A C25A 120.7(3) . . ?
C23A C24A H24A 119.6 . . ?
C25A C24A H24A 119.6 . . ?
C24A C25A C26A 122.7(3) . . ?
C24A C25A C20A 118.9(3) . . ?
C26A C25A C20A 118.4(3) . . ?
C27A C26A C25A 121.3(3) . . ?
C27A C26A H26A 119.4 . . ?
C25A C26A H26A 119.4 . . ?
C26A C27A C18A 121.1(3) . . ?
C26A C27A H27A 119.4 . . ?
C18A C27A H27A 119.4 . . ?
C7B C8B1 C9B 123.8(3) . . ?
C7B C8B1 Cl1B 114.8(3) . . ?
C9B C8B1 Cl1B 121.4(4) . . ?
C7B C8B2 C9B 123.8(3) . . ?
C7B C8B2 H8CB 118.1 . . ?
C9B C8B2 H8CB 118.1 . . ?
C14B C1B C2B 121.0(3) . . ?
C14B C1B C15B 118.4(3) . . ?
C2B C1B C15B 120.6(3) . . ?
C1B C2B C3B 123.4(3) . . ?
C1B C2B C7B 118.6(4) . . ?
C3B C2B C7B 118.0(3) . . ?
C4B C3B C2B 122.2(4) . . ?
C4B C3B H3B 118.9 . . ?
C2B C3B H3B 118.9 . . ?
C3B C4B C5B 119.6(5) . . ?
C3B C4B H4B 120.2 . . ?
C5B C4B H4B 120.2 . . ?
C6B C5B C4B 121.3(4) . . ?
C6B C5B H5B 119.4 . . ?
C4B C5B H5B 119.4 . . ?
C5B C6B C7B 120.6(5) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B H6B 119.7 . . ?
C8B2 C7B C2B 118.9(3) . . ?
C8B1 C7B C2B 118.9(3) . . ?
C8B2 C7B C6B 122.8(4) . . ?
C8B1 C7B C6B 122.8(4) . . ?
C2B C7B C6B 118.2(5) . . ?
C8B2 C9B C14B 117.3(4) . . ?
C8B1 C9B C14B 117.3(4) . . ?
C8B2 C9B C10B 124.5(3) . . ?
C8B1 C9B C10B 124.5(3) . . ?
C14B C9B C10B 118.2(3) . . ?
C11B C10B C9B 121.7(4) . . ?
C11B C10B H10B 119.2 . . ?
C9B C10B H10B 119.2 . . ?
C10B C11B C12B 120.9(4) . . ?
C10B C11B H11B 119.6 . . ?
C12B C11B H11B 119.6 . . ?
C13B C12B C11B 119.9(4) . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C12B C13B C14B 121.6(3) . . ?
C12B C13B H13B 119.2 . . ?
C14B C13B H13B 119.2 . . ?
C1B C14B C9B 120.4(3) . . ?
C1B C14B C13B 121.9(3) . . ?
C9B C14B C13B 117.7(3) . . ?
C16B C15B C1B 125.3(3) . . ?
C16B C15B H15B 117.3 . . ?
C1B C15B H15B 117.3 . . ?
C15B C16B C17B 117.3(3) . . ?
C15B C16B C18B 125.3(3) . . ?
C17B C16B C18B 117.3(3) . . ?
N1B C17B C16B 179.6(4) . . ?
C19B C18B C27B 118.6(3) . . ?
C19B C18B C16B 121.3(3) . . ?
C27B C18B C16B 120.1(3) . . ?
C18B C19B C20B 121.8(3) . . ?
C18B C19B H19B 119.1 . . ?
C20B C19B H19B 119.1 . . ?
C19B C20B C21B 122.7(3) . . ?
C19B C20B C25B 119.2(3) . . ?
C21B C20B C25B 118.1(3) . . ?
C22B C21B C20B 121.4(3) . . ?
C22B C21B H21B 119.3 . . ?
C20B C21B H21B 119.3 . . ?
C21B C22B C23B 120.3(3) . . ?
C21B C22B H22B 119.9 . . ?
C23B C22B H22B 119.9 . . ?
C24B C23B C22B 120.1(3) . . ?
C24B C23B H23B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C23B C24B C25B 120.5(3) . . ?
C23B C24B H24B 119.7 . . ?
C25B C24B H24B 119.7 . . ?
C24B C25B C20B 119.6(3) . . ?
C24B C25B C26B 122.6(3) . . ?
C20B C25B C26B 117.8(3) . . ?
C27B C26B C25B 121.9(3) . . ?
C27B C26B H26B 119.1 . . ?
C25B C26B H26B 119.1 . . ?
C26B C27B C18B 120.7(3) . . ?
C26B C27B H27B 119.6 . . ?
C18B C27B H27B 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14A C1A C2A C7A 2.3(5) . . . . ?
C15A C1A C2A C7A -178.7(3) . . . . ?
C14A C1A C2A C3A -176.0(3) . . . . ?
C15A C1A C2A C3A 3.0(5) . . . . ?
C1A C2A C3A C4A 179.7(4) . . . . ?
C7A C2A C3A C4A 1.3(5) . . . . ?
C2A C3A C4A C5A -0.2(7) . . . . ?
C3A C4A C5A C6A 0.0(8) . . . . ?
C4A C5A C6A C7A -0.9(8) . . . . ?
C9A C8A2 C7A C6A 179.3(4) . . . . ?
C9A C8A2 C7A C2A -0.9(6) . . . . ?
C9A C8A1 C7A C6A 179.3(4) . . . . ?
Cl1A C8A1 C7A C6A -2.9(5) . . . . ?
C9A C8A1 C7A C2A -0.9(6) . . . . ?
Cl1A C8A1 C7A C2A 176.9(3) . . . . ?
C5A C6A C7A C8A2 -178.2(4) . . . . ?
C5A C6A C7A C8A1 -178.2(4) . . . . ?
C5A C6A C7A C2A 2.0(6) . . . . ?
C1A C2A C7A C8A2 -0.4(5) . . . . ?
C3A C2A C7A C8A2 178.0(3) . . . . ?
C1A C2A C7A C8A1 -0.4(5) . . . . ?
C3A C2A C7A C8A1 178.0(3) . . . . ?
C1A C2A C7A C6A 179.4(3) . . . . ?
C3A C2A C7A C6A -2.2(5) . . . . ?
C7A C8A2 C9A C14A 0.4(5) . . . . ?
C7A C8A2 C9A C10A 179.2(3) . . . . ?
C7A C8A1 C9A C14A 0.4(5) . . . . ?
Cl1A C8A1 C9A C14A -177.2(3) . . . . ?
C7A C8A1 C9A C10A 179.2(3) . . . . ?
Cl1A C8A1 C9A C10A 1.7(6) . . . . ?
C8A2 C9A C10A C11A 179.6(4) . . . . ?
C8A1 C9A C10A C11A 179.6(4) . . . . ?
C14A C9A C10A C11A -1.6(6) . . . . ?
C9A C10A C11A C12A 0.8(6) . . . . ?
C10A C11A C12A C13A 0.1(6) . . . . ?
C11A C12A C13A C14A -0.2(6) . . . . ?
C2A C1A C14A C13A 178.3(3) . . . . ?
C15A C1A C14A C13A -0.7(4) . . . . ?
C2A C1A C14A C9A -2.9(5) . . . . ?
C15A C1A C14A C9A 178.1(3) . . . . ?
C12A C13A C14A C1A 178.2(3) . . . . ?
C12A C13A C14A C9A -0.6(5) . . . . ?
C8A2 C9A C14A C1A 1.5(5) . . . . ?
C8A1 C9A C14A C1A 1.5(5) . . . . ?
C10A C9A C14A C1A -177.4(3) . . . . ?
C8A2 C9A C14A C13A -179.7(3) . . . . ?
C8A1 C9A C14A C13A -179.7(3) . . . . ?
C10A C9A C14A C13A 1.5(5) . . . . ?
C2A C1A C15A C16A 71.8(5) . . . . ?
C14A C1A C15A C16A -109.2(4) . . . . ?
C1A C15A C16A C17A 1.4(5) . . . . ?
C1A C15A C16A C18A 178.5(3) . . . . ?
C15A C16A C18A C19A -156.3(3) . . . . ?
C17A C16A C18A C19A 20.8(4) . . . . ?
C15A C16A C18A C27A 22.5(4) . . . . ?
C17A C16A C18A C27A -160.4(3) . . . . ?
C27A C18A C19A C20A -1.0(4) . . . . ?
C16A C18A C19A C20A 177.7(3) . . . . ?
C18A C19A C20A C21A -179.3(3) . . . . ?
C18A C19A C20A C25A 0.5(4) . . . . ?
C19A C20A C21A C22A -179.5(3) . . . . ?
C25A C20A C21A C22A 0.6(4) . . . . ?
C20A C21A C22A C23A -0.3(5) . . . . ?
C21A C22A C23A C24A 0.1(5) . . . . ?
C22A C23A C24A C25A -0.1(5) . . . . ?
C23A C24A C25A C26A 179.7(3) . . . . ?
C23A C24A C25A C20A 0.4(4) . . . . ?
C19A C20A C25A C24A 179.5(3) . . . . ?
C21A C20A C25A C24A -0.7(4) . . . . ?
C19A C20A C25A C26A 0.2(4) . . . . ?
C21A C20A C25A C26A -179.9(3) . . . . ?
C24A C25A C26A C27A -179.7(3) . . . . ?
C20A C25A C26A C27A -0.4(4) . . . . ?
C25A C26A C27A C18A -0.1(4) . . . . ?
C19A C18A C27A C26A 0.8(4) . . . . ?
C16A C18A C27A C26A -178.0(3) . . . . ?
C14B C1B C2B C3B 178.4(3) . . . . ?
C15B C1B C2B C3B -2.2(5) . . . . ?
C14B C1B C2B C7B -0.8(5) . . . . ?
C15B C1B C2B C7B 178.6(3) . . . . ?
C1B C2B C3B C4B -180.0(4) . . . . ?
C7B C2B C3B C4B -0.8(6) . . . . ?
C2B C3B C4B C5B -0.3(7) . . . . ?
C3B C4B C5B C6B 1.2(8) . . . . ?
C4B C5B C6B C7B -1.0(8) . . . . ?
C9B C8B2 C7B C2B 1.0(5) . . . . ?
C9B C8B2 C7B C6B -179.5(4) . . . . ?
C9B C8B1 C7B C2B 1.0(5) . . . . ?
Cl1B C8B1 C7B C2B -179.9(3) . . . . ?
C9B C8B1 C7B C6B -179.5(4) . . . . ?
Cl1B C8B1 C7B C6B -0.4(5) . . . . ?
C1B C2B C7B C8B2 -0.3(5) . . . . ?
C3B C2B C7B C8B2 -179.5(3) . . . . ?
C1B C2B C7B C8B1 -0.3(5) . . . . ?
C3B C2B C7B C8B1 -179.5(3) . . . . ?
C1B C2B C7B C6B -179.8(3) . . . . ?
C3B C2B C7B C6B 0.9(5) . . . . ?
C5B C6B C7B C8B2 -179.6(4) . . . . ?
C5B C6B C7B C8B1 -179.6(4) . . . . ?
C5B C6B C7B C2B -0.1(6) . . . . ?
C7B C8B2 C9B C14B -0.5(5) . . . . ?
C7B C8B2 C9B C10B -178.5(4) . . . . ?
C7B C8B1 C9B C14B -0.5(5) . . . . ?
Cl1B C8B1 C9B C14B -179.6(3) . . . . ?
C7B C8B1 C9B C10B -178.5(4) . . . . ?
Cl1B C8B1 C9B C10B 2.5(5) . . . . ?
C8B2 C9B C10B C11B -179.7(4) . . . . ?
C8B1 C9B C10B C11B -179.7(4) . . . . ?
C14B C9B C10B C11B 2.4(6) . . . . ?
C9B C10B C11B C12B -0.7(6) . . . . ?
C10B C11B C12B C13B -1.0(6) . . . . ?
C11B C12B C13B C14B 0.9(5) . . . . ?
C2B C1B C14B C9B 1.3(5) . . . . ?
C15B C1B C14B C9B -178.2(3) . . . . ?
C2B C1B C14B C13B -178.9(3) . . . . ?
C15B C1B C14B C13B 1.7(5) . . . . ?
C8B2 C9B C14B C1B -0.6(5) . . . . ?
C8B1 C9B C14B C1B -0.6(5) . . . . ?
C10B C9B C14B C1B 177.4(3) . . . . ?
C8B2 C9B C14B C13B 179.5(3) . . . . ?
C8B1 C9B C14B C13B 179.5(3) . . . . ?
C10B C9B C14B C13B -2.4(5) . . . . ?
C12B C13B C14B C1B -179.0(3) . . . . ?
C12B C13B C14B C9B 0.8(5) . . . . ?
C14B C1B C15B C16B 106.4(4) . . . . ?
C2B C1B C15B C16B -73.0(5) . . . . ?
C1B C15B C16B C17B 0.3(5) . . . . ?
C1B C15B C16B C18B -176.5(3) . . . . ?
C15B C16B C18B C19B 156.6(3) . . . . ?
C17B C16B C18B C19B -20.1(4) . . . . ?
C15B C16B C18B C27B -22.0(4) . . . . ?
C17B C16B C18B C27B 161.3(3) . . . . ?
C27B C18B C19B C20B 1.4(4) . . . . ?
C16B C18B C19B C20B -177.2(2) . . . . ?
C18B C19B C20B C21B 179.6(3) . . . . ?
C18B C19B C20B C25B -0.7(4) . . . . ?
C19B C20B C21B C22B 179.8(3) . . . . ?
C25B C20B C21B C22B 0.0(4) . . . . ?
C20B C21B C22B C23B -0.4(5) . . . . ?
C21B C22B C23B C24B 0.5(5) . . . . ?
C22B C23B C24B C25B -0.4(5) . . . . ?
C23B C24B C25B C20B 0.1(4) . . . . ?
C23B C24B C25B C26B -179.4(3) . . . . ?
C19B C20B C25B C24B -179.7(3) . . . . ?
C21B C20B C25B C24B 0.1(4) . . . . ?
C19B C20B C25B C26B -0.1(4) . . . . ?
C21B C20B C25B C26B 179.6(3) . . . . ?
C24B C25B C26B C27B 179.7(3) . . . . ?
C20B C25B C26B C27B 0.2(4) . . . . ?
C25B C26B C27B C18B 0.5(4) . . . . ?
C19B C18B C27B C26B -1.3(4) . . . . ?
C16B C18B C27B C26B 177.3(3) . . . . ?

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_SPA909
_database_code_depnum_ccdc_archive 'CCDC 2282271'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2023-07-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
(Z)-3-(anthracen-9-yl)-2-(naphthalen-2-yl)acrylonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H17 N'
_chemical_formula_sum            'C27 H17 N'
_chemical_formula_weight         355.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 '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                   20.818(4)
_cell_length_b                   5.3880(11)
_cell_length_c                   17.241(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.10(3)
_cell_angle_gamma                90
_cell_volume                     1848.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    59789
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16622
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.814
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4621
_reflns_number_gt                3644
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0842P)²+0.1015P] 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         4621
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.29950(6) 0.5449(3) 0.44152(8) 0.0596(4) Uani 1 1 d . . . . .
C1 C 0.19202(6) 0.3684(2) 0.55937(7) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.18119(5) 0.5499(2) 0.61307(7) 0.0341(3) Uani 1 1 d . . . . .
C3 C 0.22647(6) 0.5852(2) 0.69276(7) 0.0403(3) Uani 1 1 d . . . . .
H3 H 0.264596 0.483124 0.710645 0.048 Uiso 1 1 calc R U . . .
C4 C 0.21530(7) 0.7639(3) 0.74302(8) 0.0483(3) Uani 1 1 d . . . . .
H4 H 0.245477 0.782677 0.795264 0.058 Uiso 1 1 calc R U . . .
C5 C 0.15865(8) 0.9217(3) 0.71737(9) 0.0525(4) Uani 1 1 d . . . . .
H5 H 0.151674 1.045743 0.752382 0.063 Uiso 1 1 calc R U . . .
C6 C 0.11448(7) 0.8946(3) 0.64258(9) 0.0481(3) Uani 1 1 d . . . . .
H6 H 0.077085 1.000762 0.626324 0.058 Uiso 1 1 calc R U . . .
C7 C 0.12350(6) 0.7080(2) 0.58783(8) 0.0384(3) Uani 1 1 d . . . . .
C8 C 0.07806(6) 0.6750(3) 0.51104(8) 0.0425(3) Uani 1 1 d . . . . .
H8 H 0.040393 0.779740 0.494295 0.051 Uiso 1 1 calc R U . . .
C9 C 0.08700(6) 0.4914(2) 0.45866(7) 0.0391(3) Uani 1 1 d . . . . .
C10 C 0.03906(6) 0.4534(3) 0.38081(8) 0.0499(3) Uani 1 1 d . . . . .
H10 H 0.001113 0.556908 0.364295 0.060 Uiso 1 1 calc R U . . .
C11 C 0.04738(7) 0.2721(3) 0.33085(8) 0.0535(4) Uani 1 1 d . . . . .
H11 H 0.015269 0.250596 0.280027 0.064 Uiso 1 1 calc R U . . .
C12 C 0.10390(8) 0.1141(3) 0.35414(8) 0.0510(3) Uani 1 1 d . . . . .
H12 H 0.108876 -0.012676 0.318885 0.061 Uiso 1 1 calc R U . . .
C13 C 0.15144(7) 0.1436(3) 0.42745(8) 0.0436(3) Uani 1 1 d . . . . .
H13 H 0.188865 0.037198 0.441933 0.052 Uiso 1 1 calc R U . . .
C14 C 0.14506(6) 0.3339(2) 0.48236(7) 0.0360(3) Uani 1 1 d . . . . .
C15 C 0.25355(6) 0.2150(2) 0.58651(7) 0.0365(3) Uani 1 1 d . . . . .
H15 H 0.256192 0.099634 0.628237 0.044 Uiso 1 1 calc R U . . .
C16 C 0.30571(6) 0.2279(2) 0.55617(6) 0.0323(2) Uani 1 1 d . . . . .
C17 C 0.30224(6) 0.4051(2) 0.49217(7) 0.0395(3) Uani 1 1 d . . . . .
C18 C 0.36884(6) 0.0837(2) 0.58611(6) 0.0312(2) Uani 1 1 d . . . . .
C19 C 0.42756(6) 0.1665(2) 0.57423(7) 0.0332(2) Uani 1 1 d . . . . .
H19 H 0.427035 0.312023 0.543992 0.040 Uiso 1 1 calc R U . . .
C20 C 0.48901(6) 0.0376(2) 0.60651(6) 0.0331(2) Uani 1 1 d . . . . .
C21 C 0.55027(6) 0.1216(2) 0.59571(8) 0.0404(3) Uani 1 1 d . . . . .
H21 H 0.550967 0.268216 0.566412 0.049 Uiso 1 1 calc R U . . .
C22 C 0.60850(6) -0.0091(3) 0.62761(8) 0.0460(3) Uani 1 1 d . . . . .
H22 H 0.648879 0.048367 0.620063 0.055 Uiso 1 1 calc R U . . .
C23 C 0.60823(7) -0.2273(3) 0.67134(8) 0.0472(3) Uani 1 1 d . . . . .
H23 H 0.648506 -0.315572 0.692842 0.057 Uiso 1 1 calc R U . . .
C24 C 0.55022(6) -0.3140(2) 0.68320(8) 0.0426(3) Uani 1 1 d . . . . .
H24 H 0.550900 -0.460938 0.712811 0.051 Uiso 1 1 calc R U . . .
C25 C 0.48895(6) -0.1838(2) 0.65117(7) 0.0344(3) Uani 1 1 d . . . . .
C26 C 0.42745(6) -0.2688(2) 0.66150(7) 0.0382(3) Uani 1 1 d . . . . .
H26 H 0.426809 -0.416216 0.690399 0.046 Uiso 1 1 calc R U . . .
C27 C 0.36935(6) -0.1397(2) 0.63013(7) 0.0355(3) Uani 1 1 d . . . . .
H27 H 0.329139 -0.198974 0.637679 0.043 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
N1 C17 1.1417(16) . ?
C1 C2 1.4096(16) . ?
C1 C14 1.4106(17) . ?
C1 C15 1.4801(16) . ?
C2 C7 1.4318(16) . ?
C2 C3 1.4321(17) . ?
C3 C4 1.3602(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.415(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.354(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.4288(18) . ?
C6 H6 0.9400 . ?
C7 C8 1.3939(19) . ?
C8 C9 1.3884(19) . ?
C8 H8 0.9400 . ?
C9 C10 1.4325(18) . ?
C9 C14 1.4346(17) . ?
C10 C11 1.347(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.412(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.366(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4279(18) . ?
C13 H13 0.9400 . ?
C15 C16 1.3387(16) . ?
C15 H15 0.9400 . ?
C16 C17 1.4447(16) . ?
C16 C18 1.4828(16) . ?
C18 C19 1.3718(16) . ?
C18 C27 1.4215(16) . ?
C19 C20 1.4178(16) . ?
C19 H19 0.9400 . ?
C20 C21 1.4161(17) . ?
C20 C25 1.4200(16) . ?
C21 C22 1.3696(19) . ?
C21 H21 0.9400 . ?
C22 C23 1.398(2) . ?
C22 H22 0.9400 . ?
C23 C24 1.3652(19) . ?
C23 H23 0.9400 . ?
C24 C25 1.4175(17) . ?
C24 H24 0.9400 . ?
C25 C26 1.4194(17) . ?
C26 C27 1.3618(17) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?

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 C14 120.62(11) . . ?
C2 C1 C15 118.06(10) . . ?
C14 C1 C15 121.32(11) . . ?
C1 C2 C7 119.66(11) . . ?
C1 C2 C3 122.35(11) . . ?
C7 C2 C3 117.99(11) . . ?
C4 C3 C2 121.17(12) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.60(13) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.20(13) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.39(13) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 122.20(12) . . ?
C8 C7 C2 119.16(11) . . ?
C6 C7 C2 118.64(12) . . ?
C9 C8 C7 121.69(11) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.44(12) . . ?
C8 C9 C14 119.94(11) . . ?
C10 C9 C14 118.62(12) . . ?
C11 C10 C9 121.17(13) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.58(13) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.63(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.91(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C1 C14 C13 123.02(11) . . ?
C1 C14 C9 118.87(11) . . ?
C13 C14 C9 118.08(11) . . ?
C16 C15 C1 124.99(11) . . ?
C16 C15 H15 117.5 . . ?
C1 C15 H15 117.5 . . ?
C15 C16 C17 117.95(10) . . ?
C15 C16 C18 125.07(10) . . ?
C17 C16 C18 116.89(10) . . ?
N1 C17 C16 179.91(17) . . ?
C19 C18 C27 119.20(10) . . ?
C19 C18 C16 121.01(10) . . ?
C27 C18 C16 119.75(10) . . ?
C18 C19 C20 121.54(11) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C21 C20 C19 122.37(11) . . ?
C21 C20 C25 118.97(11) . . ?
C19 C20 C25 118.67(10) . . ?
C22 C21 C20 120.52(13) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 120.38(12) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 120.83(12) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.45(12) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 122.22(11) . . ?
C24 C25 C20 118.86(11) . . ?
C26 C25 C20 118.92(10) . . ?
C27 C26 C25 120.94(11) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C18 120.71(11) . . ?
C26 C27 H27 119.6 . . ?
C18 C27 H27 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C7 -2.78(17) . . . . ?
C15 C1 C2 C7 177.72(10) . . . . ?
C14 C1 C2 C3 177.88(11) . . . . ?
C15 C1 C2 C3 -1.62(17) . . . . ?
C1 C2 C3 C4 179.15(11) . . . . ?
C7 C2 C3 C4 -0.20(18) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 179.07(13) . . . . ?
C5 C6 C7 C2 -0.8(2) . . . . ?
C1 C2 C7 C8 1.62(17) . . . . ?
C3 C2 C7 C8 -179.01(11) . . . . ?
C1 C2 C7 C6 -178.47(11) . . . . ?
C3 C2 C7 C6 0.90(17) . . . . ?
C6 C7 C8 C9 -179.36(12) . . . . ?
C2 C7 C8 C9 0.55(19) . . . . ?
C7 C8 C9 C10 178.04(12) . . . . ?
C7 C8 C9 C14 -1.56(19) . . . . ?
C8 C9 C10 C11 -178.77(13) . . . . ?
C14 C9 C10 C11 0.83(19) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C2 C1 C14 C13 -176.24(11) . . . . ?
C15 C1 C14 C13 3.24(17) . . . . ?
C2 C1 C14 C9 1.77(17) . . . . ?
C15 C1 C14 C9 -178.75(10) . . . . ?
C12 C13 C14 C1 178.61(12) . . . . ?
C12 C13 C14 C9 0.59(18) . . . . ?
C8 C9 C14 C1 0.40(17) . . . . ?
C10 C9 C14 C1 -179.22(11) . . . . ?
C8 C9 C14 C13 178.50(11) . . . . ?
C10 C9 C14 C13 -1.11(17) . . . . ?
C2 C1 C15 C16 -110.70(14) . . . . ?
C14 C1 C15 C16 69.81(16) . . . . ?
C1 C15 C16 C17 0.17(18) . . . . ?
C1 C15 C16 C18 176.68(11) . . . . ?
C15 C16 C18 C19 -155.85(12) . . . . ?
C17 C16 C18 C19 20.69(16) . . . . ?
C15 C16 C18 C27 22.07(17) . . . . ?
C17 C16 C18 C27 -161.39(11) . . . . ?
C27 C18 C19 C20 -1.54(17) . . . . ?
C16 C18 C19 C20 176.39(10) . . . . ?
C18 C19 C20 C21 -179.25(11) . . . . ?
C18 C19 C20 C25 0.81(16) . . . . ?
C19 C20 C21 C22 -179.72(11) . . . . ?
C25 C20 C21 C22 0.22(18) . . . . ?
C20 C21 C22 C23 -0.02(19) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C22 C23 C24 C25 0.09(19) . . . . ?
C23 C24 C25 C26 179.41(11) . . . . ?
C23 C24 C25 C20 0.11(18) . . . . ?
C21 C20 C25 C24 -0.26(16) . . . . ?
C19 C20 C25 C24 179.68(10) . . . . ?
C21 C20 C25 C26 -179.58(10) . . . . ?
C19 C20 C25 C26 0.36(16) . . . . ?
C24 C25 C26 C27 179.92(11) . . . . ?
C20 C25 C26 C27 -0.78(17) . . . . ?
C25 C26 C27 C18 0.06(18) . . . . ?
C19 C18 C27 C26 1.10(17) . . . . ?
C16 C18 C27 C26 -176.85(10) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.039

