# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_X
_database_code_depnum_ccdc_archive 'CCDC 1477084'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ' 1-phenyl-3-(1-pyrenyl) prop-2-en-1-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 O'
_chemical_formula_weight         332.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.5050(11)
_cell_length_b                   9.6100(19)
_cell_length_c                   16.517(3)
_cell_angle_alpha                99.15(3)
_cell_angle_beta                 98.70(3)
_cell_angle_gamma                100.80(3)
_cell_volume                     832.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8
_cell_measurement_theta_max      12

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3406
_diffrn_reflns_av_unetI/netI     0.1439
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.271
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3061
_reflns_number_gt                1291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3061
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2175
_refine_ls_R_factor_gt           0.0960
_refine_ls_wR_factor_ref         0.2068
_refine_ls_wR_factor_gt          0.1651
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O O 0.0526(7) 0.1643(4) 0.5068(2) 0.0632(11) Uani 1 1 d . . . . .
C1 C 0.5503(10) 0.2413(6) 0.6835(3) 0.0555(14) Uani 1 1 d . . . . .
H1A H 0.6797 0.2870 0.6604 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5804(11) 0.2441(6) 0.7682(3) 0.0594(15) Uani 1 1 d . . . . .
H2A H 0.7318 0.2938 0.8024 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3922(11) 0.1754(6) 0.8035(3) 0.0585(15) Uani 1 1 d . . . . .
H3A H 0.4183 0.1760 0.8605 0.070 Uiso 1 1 calc R U . . .
C4 C 0.1655(12) 0.1062(6) 0.7533(3) 0.0625(16) Uani 1 1 d . . . . .
H4A H 0.0342 0.0619 0.7762 0.075 Uiso 1 1 calc R U . . .
C5 C 0.1356(10) 0.1033(5) 0.6685(3) 0.0559(14) Uani 1 1 d . . . . .
H5A H -0.0167 0.0551 0.6342 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3224(9) 0.1687(5) 0.6341(3) 0.0427(12) Uani 1 1 d . . . . .
C7 C 0.2639(8) 0.1725(5) 0.5411(3) 0.0409(11) Uani 1 1 d . . . . .
C8 C 0.4823(11) 0.1899(5) 0.5003(3) 0.0553(14) Uani 1 1 d . . . . .
H8A H 0.6247 0.1656 0.5275 0.066 Uiso 1 1 calc R U . . .
C9 C 0.5045(9) 0.2368(5) 0.4283(3) 0.0501(13) Uani 1 1 d . . . . .
H9A H 0.6516 0.2293 0.4083 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3241(9) 0.2979(5) 0.3779(3) 0.0461(12) Uani 1 1 d . . . . .
C11 C 0.2028(10) 0.3997(5) 0.4152(3) 0.0538(14) Uani 1 1 d . . . . .
H11A H 0.2358 0.4272 0.4730 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0374(11) 0.4602(5) 0.3693(3) 0.0605(16) Uani 1 1 d . . . . .
H12A H -0.0498 0.5221 0.3958 0.073 Uiso 1 1 calc R U . . .
C13 C -0.0006(9) 0.4269(5) 0.2795(3) 0.0461(13) Uani 1 1 d . . . . .
C14 C 0.1233(8) 0.3267(5) 0.2416(3) 0.0377(11) Uani 1 1 d . . . . .
C15 C 0.2900(9) 0.2610(5) 0.2880(3) 0.0438(12) Uani 1 1 d . . . . .
C16 C -0.1778(11) 0.4885(6) 0.2323(4) 0.0689(17) Uani 1 1 d . . . . .
H16A H -0.2679 0.5485 0.2590 0.083 Uiso 1 1 calc R U . . .
C17 C -0.2121(11) 0.4575(5) 0.1470(4) 0.0633(15) Uani 1 1 d . . . . .
H17A H -0.3211 0.5010 0.1161 0.076 Uiso 1 1 calc R U . . .
C18 C -0.0886(9) 0.3625(5) 0.1050(3) 0.0457(12) Uani 1 1 d . . . . .
C19 C 0.0779(10) 0.2974(5) 0.1519(3) 0.0538(14) Uani 1 1 d . . . . .
C20 C -0.1234(12) 0.3256(6) 0.0178(3) 0.0698(18) Uani 1 1 d . . . . .
H20A H -0.2398 0.3622 -0.0148 0.084 Uiso 1 1 calc R U . . .
C21 C 0.0099(12) 0.2374(7) -0.0200(4) 0.0741(18) Uani 1 1 d . . . . .
H21A H -0.0129 0.2193 -0.0779 0.089 Uiso 1 1 calc R U . . .
C22 C 0.1756(11) 0.1742(6) 0.0234(3) 0.0627(16) Uani 1 1 d . . . . .
H22A H 0.2661 0.1148 -0.0035 0.075 Uiso 1 1 calc R U . . .
C23 C 0.2028(10) 0.2036(5) 0.1112(3) 0.0450(12) Uani 1 1 d . . . . .
C24 C 0.3755(10) 0.1397(5) 0.1597(3) 0.0507(13) Uani 1 1 d . . . . .
H24A H 0.4640 0.0792 0.1326 0.061 Uiso 1 1 calc R U . . .
C25 C 0.4117(10) 0.1660(5) 0.2442(3) 0.0529(14) Uani 1 1 d . . . . .
H25A H 0.5196 0.1201 0.2738 0.063 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
O C7 1.197(5) . ?
C1 C2 1.378(6) . ?
C1 C6 1.382(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.378(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.373(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.350(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.528(6) . ?
C7 C8 1.460(6) . ?
C8 C9 1.352(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.465(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.400(6) . ?
C10 C15 1.446(6) . ?
C11 C12 1.367(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.442(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.403(6) . ?
C13 C16 1.429(7) . ?
C14 C15 1.409(6) . ?
C14 C19 1.437(6) . ?
C15 C25 1.405(6) . ?
C16 C17 1.368(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.397(7) . ?
C17 H17A 0.9300 . ?
C18 C20 1.402(7) . ?
C18 C19 1.409(6) . ?
C19 C23 1.385(7) . ?
C20 C21 1.360(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.365(7) . ?
C21 H21A 0.9300 . ?
C22 C23 1.411(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.438(6) . ?
C24 C25 1.355(6) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.1(5) . . ?
C2 C1 H1A 121.0 . . ?
C6 C1 H1A 121.0 . . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 H2A 119.1 . . ?
C1 C2 H2A 119.1 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 121.5(5) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 C7 117.8(5) . . ?
C1 C6 C7 121.5(4) . . ?
O C7 C8 124.3(5) . . ?
O C7 C6 120.6(4) . . ?
C8 C7 C6 115.1(4) . . ?
C9 C8 C7 128.4(5) . . ?
C9 C8 H8A 115.8 . . ?
C7 C8 H8A 115.8 . . ?
C8 C9 C10 127.7(5) . . ?
C8 C9 H9A 116.2 . . ?
C10 C9 H9A 116.2 . . ?
C11 C10 C15 120.0(4) . . ?
C11 C10 C9 121.2(5) . . ?
C15 C10 C9 118.6(4) . . ?
C12 C11 C10 122.2(5) . . ?
C12 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
C11 C12 C13 119.4(5) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C14 C13 C16 122.3(5) . . ?
C14 C13 C12 118.7(4) . . ?
C16 C13 C12 118.8(5) . . ?
C13 C14 C15 122.5(4) . . ?
C13 C14 C19 116.2(4) . . ?
C15 C14 C19 121.2(5) . . ?
C25 C15 C14 118.2(4) . . ?
C25 C15 C10 124.8(4) . . ?
C14 C15 C10 117.0(4) . . ?
C17 C16 C13 118.6(5) . . ?
C17 C16 H16A 120.7 . . ?
C13 C16 H16A 120.7 . . ?
C16 C17 C18 122.1(5) . . ?
C16 C17 H17A 119.0 . . ?
C18 C17 H17A 119.0 . . ?
C17 C18 C20 123.6(5) . . ?
C17 C18 C19 119.0(5) . . ?
C20 C18 C19 117.4(5) . . ?
C23 C19 C18 119.6(5) . . ?
C23 C19 C14 118.8(5) . . ?
C18 C19 C14 121.6(5) . . ?
C21 C20 C18 121.2(5) . . ?
C21 C20 H20A 119.4 . . ?
C18 C20 H20A 119.4 . . ?
C20 C21 C22 122.9(6) . . ?
C20 C21 H21A 118.6 . . ?
C22 C21 H21A 118.6 . . ?
C21 C22 C23 116.7(5) . . ?
C21 C22 H22A 121.7 . . ?
C23 C22 H22A 121.7 . . ?
C19 C23 C22 122.0(5) . . ?
C19 C23 C24 119.2(4) . . ?
C22 C23 C24 118.7(5) . . ?
C25 C24 C23 121.2(5) . . ?
C25 C24 H24A 119.4 . . ?
C23 C24 H24A 119.4 . . ?
C24 C25 C15 121.4(5) . . ?
C24 C25 H25A 119.3 . . ?
C15 C25 H25A 119.3 . . ?

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
C6 C1 C2 C3 0.9(8) . . . . ?
C1 C2 C3 C4 -2.1(8) . . . . ?
C2 C3 C4 C5 2.1(8) . . . . ?
C3 C4 C5 C6 -1.0(8) . . . . ?
C4 C5 C6 C1 -0.2(8) . . . . ?
C4 C5 C6 C7 -174.1(5) . . . . ?
C2 C1 C6 C5 0.3(8) . . . . ?
C2 C1 C6 C7 173.9(5) . . . . ?
C5 C6 C7 O 24.6(7) . . . . ?
C1 C6 C7 O -149.2(5) . . . . ?
C5 C6 C7 C8 -156.7(4) . . . . ?
C1 C6 C7 C8 29.5(7) . . . . ?
O C7 C8 C9 19.0(9) . . . . ?
C6 C7 C8 C9 -159.6(5) . . . . ?
C7 C8 C9 C10 7.8(9) . . . . ?
C8 C9 C10 C11 43.6(8) . . . . ?
C8 C9 C10 C15 -142.0(5) . . . . ?
C15 C10 C11 C12 4.4(8) . . . . ?
C9 C10 C11 C12 178.8(5) . . . . ?
C10 C11 C12 C13 -4.7(8) . . . . ?
C11 C12 C13 C14 3.6(8) . . . . ?
C11 C12 C13 C16 178.8(5) . . . . ?
C16 C13 C14 C15 -177.2(5) . . . . ?
C12 C13 C14 C15 -2.2(7) . . . . ?
C16 C13 C14 C19 4.8(7) . . . . ?
C12 C13 C14 C19 179.8(5) . . . . ?
C13 C14 C15 C25 -177.7(4) . . . . ?
C19 C14 C15 C25 0.1(7) . . . . ?
C13 C14 C15 C10 1.9(7) . . . . ?
C19 C14 C15 C10 179.7(4) . . . . ?
C11 C10 C15 C25 176.7(5) . . . . ?
C9 C10 C15 C25 2.2(7) . . . . ?
C11 C10 C15 C14 -2.8(7) . . . . ?
C9 C10 C15 C14 -177.3(4) . . . . ?
C14 C13 C16 C17 -5.4(8) . . . . ?
C12 C13 C16 C17 179.6(5) . . . . ?
C13 C16 C17 C18 3.1(8) . . . . ?
C16 C17 C18 C20 178.5(6) . . . . ?
C16 C17 C18 C19 -0.5(8) . . . . ?
C17 C18 C19 C23 -179.6(5) . . . . ?
C20 C18 C19 C23 1.3(7) . . . . ?
C17 C18 C19 C14 0.0(7) . . . . ?
C20 C18 C19 C14 -179.1(5) . . . . ?
C13 C14 C19 C23 177.5(4) . . . . ?
C15 C14 C19 C23 -0.4(7) . . . . ?
C13 C14 C19 C18 -2.1(7) . . . . ?
C15 C14 C19 C18 180.0(5) . . . . ?
C17 C18 C20 C21 177.1(6) . . . . ?
C19 C18 C20 C21 -3.9(8) . . . . ?
C18 C20 C21 C22 3.0(10) . . . . ?
C20 C21 C22 C23 0.5(9) . . . . ?
C18 C19 C23 C22 2.2(7) . . . . ?
C14 C19 C23 C22 -177.4(5) . . . . ?
C18 C19 C23 C24 179.0(5) . . . . ?
C14 C19 C23 C24 -0.7(7) . . . . ?
C21 C22 C23 C19 -3.2(8) . . . . ?
C21 C22 C23 C24 -179.9(5) . . . . ?
C19 C23 C24 C25 2.2(7) . . . . ?
C22 C23 C24 C25 179.0(5) . . . . ?
C23 C24 C25 C15 -2.6(8) . . . . ?
C14 C15 C25 C24 1.4(7) . . . . ?
C10 C15 C25 C24 -178.2(5) . . . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/ethanol'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1473276'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        '3-(9-anthryl)-1-(4-chloro) prop-2-en-1-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 Cl O'
_chemical_formula_weight         342.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   5.4320(11)
_cell_length_b                   19.431(4)
_cell_length_c                   16.208(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.65(3)
_cell_angle_gamma                90
_cell_volume                     1702.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       rodlike
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3485
_diffrn_reflns_av_unetI/netI     0.1412
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.641
_diffrn_reflns_theta_max         25.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3139
_reflns_number_gt                1263
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3139
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1980
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.1644
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Cl Cl 0.8272(3) -0.15341(8) 0.42053(8) 0.0955(6) Uani 1 1 d . . . . .
O O 1.4019(6) 0.0089(2) 0.7416(2) 0.0760(12) Uani 1 1 d . . . . .
C1 C 0.7558(10) 0.1690(2) 0.8638(3) 0.0546(13) Uani 1 1 d . . . . .
C2 C 0.6953(10) 0.1857(3) 0.7789(3) 0.0625(15) Uani 1 1 d . . . . .
H2A H 0.7873 0.1669 0.7389 0.075 Uiso 1 1 calc R U . . .
C3 C 0.5003(11) 0.2296(3) 0.7552(4) 0.0727(16) Uani 1 1 d . . . . .
H3A H 0.4645 0.2404 0.6994 0.087 Uiso 1 1 calc R U . . .
C4 C 0.3538(11) 0.2585(3) 0.8143(3) 0.0730(17) Uani 1 1 d . . . . .
H4A H 0.2223 0.2876 0.7976 0.088 Uiso 1 1 calc R U . . .
C5 C 0.4090(10) 0.2430(2) 0.8953(3) 0.0648(15) Uani 1 1 d . . . . .
H5A H 0.3089 0.2608 0.9334 0.078 Uiso 1 1 calc R U . . .
C6 C 0.6093(9) 0.2013(2) 0.9247(3) 0.0512(13) Uani 1 1 d . . . . .
C7 C 0.6883(11) 0.1914(2) 1.0085(3) 0.0661(16) Uani 1 1 d . . . . .
H7A H 0.6046 0.2146 1.0474 0.079 Uiso 1 1 calc R U . . .
C8 C 0.8783(11) 0.1501(3) 1.0366(3) 0.0593(14) Uani 1 1 d . . . . .
C9 C 0.9541(11) 0.1435(3) 1.1224(3) 0.0728(17) Uani 1 1 d . . . . .
H9A H 0.8694 0.1669 1.1610 0.087 Uiso 1 1 calc R U . . .
C10 C 1.1488(12) 0.1034(3) 1.1479(3) 0.0757(17) Uani 1 1 d . . . . .
H10A H 1.1987 0.1005 1.2044 0.091 Uiso 1 1 calc R U . . .
C11 C 1.2789(10) 0.0659(3) 1.0928(3) 0.0692(16) Uani 1 1 d . . . . .
H11A H 1.4096 0.0375 1.1122 0.083 Uiso 1 1 calc R U . . .
C12 C 1.2102(10) 0.0720(3) 1.0096(3) 0.0618(15) Uani 1 1 d . . . . .
H12A H 1.2940 0.0465 0.9726 0.074 Uiso 1 1 calc R U . . .
C13 C 1.0179(9) 0.1154(2) 0.9785(3) 0.0499(12) Uani 1 1 d . . . . .
C14 C 0.9473(9) 0.1245(2) 0.8918(3) 0.0519(13) Uani 1 1 d . . . . .
C15 C 1.0980(10) 0.0872(2) 0.8345(3) 0.0602(14) Uani 1 1 d . . . . .
H15A H 1.2691 0.0911 0.8439 0.072 Uiso 1 1 calc R U . . .
C16 C 1.0064(10) 0.0479(2) 0.7695(2) 0.0568(14) Uani 1 1 d . . . . .
H16A H 0.8370 0.0463 0.7540 0.068 Uiso 1 1 calc R U . . .
C17 C 1.1770(9) 0.0081(3) 0.7242(3) 0.0506(13) Uani 1 1 d . . . . .
C18 C 1.0703(9) -0.0341(2) 0.6508(3) 0.0479(12) Uani 1 1 d . . . . .
C19 C 1.2149(10) -0.0874(3) 0.6235(3) 0.0636(15) Uani 1 1 d . . . . .
H19A H 1.3667 -0.0977 0.6525 0.076 Uiso 1 1 calc R U . . .
C20 C 1.1353(12) -0.1242(3) 0.5550(4) 0.087(2) Uani 1 1 d . . . . .
H20A H 1.2312 -0.1604 0.5383 0.104 Uiso 1 1 calc R U . . .
C21 C 0.9240(11) -0.1095(3) 0.5118(3) 0.0643(16) Uani 1 1 d . . . . .
C22 C 0.7727(10) -0.0576(3) 0.5373(3) 0.0714(17) Uani 1 1 d . . . . .
H22A H 0.6209 -0.0482 0.5078 0.086 Uiso 1 1 calc R U . . .
C23 C 0.8524(9) -0.0202(3) 0.6077(3) 0.0633(15) Uani 1 1 d . . . . .
H23A H 0.7536 0.0149 0.6253 0.076 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
Cl C21 1.744(5) . ?
O C17 1.227(5) . ?
C1 C14 1.394(6) . ?
C1 C2 1.420(6) . ?
C1 C6 1.468(6) . ?
C2 C3 1.385(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.421(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.351(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.398(6) . ?
C7 C8 1.350(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.418(6) . ?
C8 C13 1.434(6) . ?
C9 C10 1.346(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.397(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.368(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.397(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.431(6) . ?
C14 C15 1.486(6) . ?
C15 C16 1.355(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.459(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.512(6) . ?
C18 C23 1.341(6) . ?
C18 C19 1.398(6) . ?
C19 C20 1.356(7) . ?
C19 H19A 0.9300 . ?
C20 C21 1.315(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.389(7) . ?
C22 C23 1.386(6) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 123.4(5) . . ?
C14 C1 C6 118.9(4) . . ?
C2 C1 C6 117.7(5) . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 123.4(5) . . ?
C4 C5 H5A 118.3 . . ?
C6 C5 H5A 118.3 . . ?
C7 C6 C5 124.4(5) . . ?
C7 C6 C1 117.3(5) . . ?
C5 C6 C1 118.2(4) . . ?
C8 C7 C6 124.1(5) . . ?
C8 C7 H7A 117.9 . . ?
C6 C7 H7A 117.9 . . ?
C7 C8 C9 121.5(5) . . ?
C7 C8 C13 119.6(4) . . ?
C9 C8 C13 118.7(5) . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 122.5(5) . . ?
C9 C10 H10A 118.8 . . ?
C11 C10 H10A 118.8 . . ?
C12 C11 C10 118.7(5) . . ?
C12 C11 H11A 120.7 . . ?
C10 C11 H11A 120.7 . . ?
C11 C12 C13 121.9(5) . . ?
C11 C12 H12A 119.0 . . ?
C13 C12 H12A 119.0 . . ?
C12 C13 C14 123.2(5) . . ?
C12 C13 C8 118.2(4) . . ?
C14 C13 C8 118.6(5) . . ?
C1 C14 C13 121.1(5) . . ?
C1 C14 C15 122.6(4) . . ?
C13 C14 C15 116.2(5) . . ?
C16 C15 C14 125.3(5) . . ?
C16 C15 H15A 117.3 . . ?
C14 C15 H15A 117.3 . . ?
C15 C16 C17 119.1(5) . . ?
C15 C16 H16A 120.4 . . ?
C17 C16 H16A 120.4 . . ?
O C17 C16 123.0(5) . . ?
O C17 C18 118.9(5) . . ?
C16 C17 C18 118.0(4) . . ?
C23 C18 C19 118.6(5) . . ?
C23 C18 C17 123.4(5) . . ?
C19 C18 C17 117.8(4) . . ?
C20 C19 C18 120.4(5) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C21 C20 C19 120.7(6) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C20 C21 C22 120.7(6) . . ?
C20 C21 Cl 121.2(5) . . ?
C22 C21 Cl 118.0(5) . . ?
C23 C22 C21 118.6(5) . . ?
C23 C22 H22A 120.7 . . ?
C21 C22 H22A 120.7 . . ?
C18 C23 C22 120.8(5) . . ?
C18 C23 H23A 119.6 . . ?
C22 C23 H23A 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 C3 179.1(4) . . . . ?
C6 C1 C2 C3 -1.6(7) . . . . ?
C1 C2 C3 C4 -0.8(8) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 C6 2.2(8) . . . . ?
C4 C5 C6 C7 171.8(5) . . . . ?
C4 C5 C6 C1 -4.5(7) . . . . ?
C14 C1 C6 C7 6.8(7) . . . . ?
C2 C1 C6 C7 -172.5(4) . . . . ?
C14 C1 C6 C5 -176.6(4) . . . . ?
C2 C1 C6 C5 4.1(7) . . . . ?
C5 C6 C7 C8 178.6(5) . . . . ?
C1 C6 C7 C8 -5.0(7) . . . . ?
C6 C7 C8 C9 178.3(5) . . . . ?
C6 C7 C8 C13 2.3(8) . . . . ?
C7 C8 C9 C10 -178.1(5) . . . . ?
C13 C8 C9 C10 -2.1(8) . . . . ?
C8 C9 C10 C11 -1.5(8) . . . . ?
C9 C10 C11 C12 2.1(8) . . . . ?
C10 C11 C12 C13 1.3(8) . . . . ?
C11 C12 C13 C14 177.8(5) . . . . ?
C11 C12 C13 C8 -4.8(7) . . . . ?
C7 C8 C13 C12 -178.7(4) . . . . ?
C9 C8 C13 C12 5.2(7) . . . . ?
C7 C8 C13 C14 -1.3(7) . . . . ?
C9 C8 C13 C14 -177.3(4) . . . . ?
C2 C1 C14 C13 173.1(5) . . . . ?
C6 C1 C14 C13 -6.2(7) . . . . ?
C2 C1 C14 C15 -3.5(7) . . . . ?
C6 C1 C14 C15 177.3(4) . . . . ?
C12 C13 C14 C1 -179.3(4) . . . . ?
C8 C13 C14 C1 3.4(7) . . . . ?
C12 C13 C14 C15 -2.5(7) . . . . ?
C8 C13 C14 C15 -179.8(4) . . . . ?
C1 C14 C15 C16 -52.3(7) . . . . ?
C13 C14 C15 C16 130.9(5) . . . . ?
C14 C15 C16 C17 -173.2(4) . . . . ?
C15 C16 C17 O -0.7(8) . . . . ?
C15 C16 C17 C18 -178.6(4) . . . . ?
O C17 C18 C23 -154.4(5) . . . . ?
C16 C17 C18 C23 23.6(7) . . . . ?
O C17 C18 C19 21.2(7) . . . . ?
C16 C17 C18 C19 -160.7(4) . . . . ?
C23 C18 C19 C20 -0.1(8) . . . . ?
C17 C18 C19 C20 -176.0(5) . . . . ?
C18 C19 C20 C21 1.7(9) . . . . ?
C19 C20 C21 C22 -2.6(9) . . . . ?
C19 C20 C21 Cl 176.6(4) . . . . ?
C20 C21 C22 C23 2.0(8) . . . . ?
Cl C21 C22 C23 -177.2(4) . . . . ?
C19 C18 C23 C22 -0.4(8) . . . . ?
C17 C18 C23 C22 175.2(5) . . . . ?
C21 C22 C23 C18 -0.5(8) . . . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.055

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/acetic acid'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1473284'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'3-(1-pyrenyl)-1-(4-chlorophenyl) prop-2-en-1-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H15 Cl O'
_chemical_formula_weight         366.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   31.234(6)
_cell_length_b                   4.8180(10)
_cell_length_c                   11.669(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1756.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       rodlike
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3765
_diffrn_reflns_av_unetI/netI     0.1538
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.304
_diffrn_reflns_theta_max         25.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3207
_reflns_number_gt                1436
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.673
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0105P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3207
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1937
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1172
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Cl Cl 0.88928(8) 1.3375(6) 0.3151(2) 0.0733(8) Uani 1 1 d . . . . .
O O 0.75681(19) 0.5612(16) 0.6197(5) 0.087(3) Uani 1 1 d . . . . .
C1 C 0.6244(2) 0.0524(17) 0.4735(7) 0.043(2) Uani 1 1 d . . . . .
C2 C 0.6078(2) 0.2020(17) 0.5690(7) 0.049(2) Uani 1 1 d . . . . .
H2A H 0.6247 0.3359 0.6043 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5678(2) 0.152(2) 0.6095(7) 0.058(3) Uani 1 1 d . . . . .
H3A H 0.5579 0.2523 0.6723 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5406(2) -0.0500(18) 0.5574(7) 0.050(2) Uani 1 1 d . . . . .
C5 C 0.5558(3) -0.1965(18) 0.4619(7) 0.043(2) Uani 1 1 d . . . . .
C6 C 0.5972(2) -0.1443(18) 0.4186(7) 0.0396(19) Uani 1 1 d . . . . .
C7 C 0.5000(3) -0.108(2) 0.6004(8) 0.066(3) Uani 1 1 d . . . . .
H7A H 0.4901 -0.0118 0.6643 0.079 Uiso 1 1 calc R U . . .
C8 C 0.4740(3) -0.306(2) 0.5492(9) 0.075(3) Uani 1 1 d . . . . .
H8A H 0.4470 -0.3436 0.5794 0.090 Uiso 1 1 calc R U . . .
C9 C 0.4880(3) -0.447(2) 0.4540(8) 0.068(3) Uani 1 1 d . . . . .
H9A H 0.4703 -0.5782 0.4196 0.082 Uiso 1 1 calc R U . . .
C10 C 0.5289(3) -0.394(2) 0.4082(7) 0.053(3) Uani 1 1 d . . . . .
C11 C 0.5443(3) -0.535(2) 0.3106(8) 0.064(3) Uani 1 1 d . . . . .
H11A H 0.5268 -0.6655 0.2752 0.077 Uiso 1 1 calc R U . . .
C12 C 0.5830(3) -0.4885(19) 0.2678(7) 0.060(3) Uani 1 1 d . . . . .
H12A H 0.5918 -0.5840 0.2027 0.072 Uiso 1 1 calc R U . . .
C13 C 0.6112(3) -0.2933(17) 0.3202(7) 0.048(2) Uani 1 1 d . . . . .
C14 C 0.6517(3) -0.2374(19) 0.2782(7) 0.060(3) Uani 1 1 d . . . . .
H14A H 0.6613 -0.3304 0.2132 0.072 Uiso 1 1 calc R U . . .
C15 C 0.6782(3) -0.0464(19) 0.3307(7) 0.059(3) Uani 1 1 d . . . . .
H15A H 0.7051 -0.0120 0.2994 0.070 Uiso 1 1 calc R U . . .
C16 C 0.6658(2) 0.0962(18) 0.4291(7) 0.046(2) Uani 1 1 d . . . . .
C17 C 0.6964(2) 0.2779(17) 0.4858(7) 0.047(2) Uani 1 1 d . . . . .
H17A H 0.6903 0.3200 0.5618 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7319(2) 0.3920(17) 0.4442(7) 0.051(2) Uani 1 1 d . . . . .
H18A H 0.7389 0.3641 0.3675 0.061 Uiso 1 1 calc R U . . .
C19 C 0.7604(3) 0.561(2) 0.5159(8) 0.056(3) Uani 1 1 d . . . . .
C20 C 0.7930(2) 0.7380(18) 0.4610(7) 0.046(2) Uani 1 1 d . . . . .
C21 C 0.7930(2) 0.7981(18) 0.3451(6) 0.048(2) Uani 1 1 d . . . . .
H21A H 0.7734 0.7106 0.2971 0.058 Uiso 1 1 calc R U . . .
C22 C 0.8222(2) 0.9891(17) 0.2991(7) 0.049(2) Uani 1 1 d . . . . .
H22A H 0.8210 1.0371 0.2220 0.059 Uiso 1 1 calc R U . . .
C23 C 0.8522(3) 1.1034(19) 0.3697(7) 0.048(2) Uani 1 1 d . . . . .
C24 C 0.8542(3) 1.0382(19) 0.4827(8) 0.058(3) Uani 1 1 d . . . . .
H24A H 0.8757 1.1116 0.5288 0.069 Uiso 1 1 calc R U . . .
C25 C 0.8237(3) 0.861(2) 0.5287(7) 0.060(3) Uani 1 1 d . . . . .
H25A H 0.8240 0.8237 0.6069 0.072 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
Cl C23 1.737(8) . ?
O C19 1.216(8) . ?
C1 C16 1.410(9) . ?
C1 C6 1.424(10) . ?
C1 C2 1.424(10) . ?
C2 C3 1.357(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.429(10) . ?
C3 H3A 0.9300 . ?
C4 C7 1.393(9) . ?
C4 C5 1.402(10) . ?
C5 C6 1.411(9) . ?
C5 C10 1.415(10) . ?
C6 C13 1.422(10) . ?
C7 C8 1.390(12) . ?
C7 H7A 0.9300 . ?
C8 C9 1.373(12) . ?
C8 H8A 0.9300 . ?
C9 C10 1.410(10) . ?
C9 H9A 0.9300 . ?
C10 C11 1.410(11) . ?
C11 C12 1.326(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.427(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.384(10) . ?
C14 C15 1.381(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.394(11) . ?
C15 H15A 0.9300 . ?
C16 C17 1.456(10) . ?
C17 C18 1.328(9) . ?
C17 H17A 0.9300 . ?
C18 C19 1.470(10) . ?
C18 H18A 0.9300 . ?
C19 C20 1.472(10) . ?
C20 C25 1.376(10) . ?
C20 C21 1.384(9) . ?
C21 C22 1.401(10) . ?
C21 H21A 0.9300 . ?
C22 C23 1.364(9) . ?
C22 H22A 0.9300 . ?
C23 C24 1.358(10) . ?
C24 C25 1.388(11) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?

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
C16 C1 C6 118.7(8) . . ?
C16 C1 C2 123.0(8) . . ?
C6 C1 C2 118.2(7) . . ?
C3 C2 C1 121.2(8) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C2 C3 C4 121.3(8) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C7 C4 C5 119.6(8) . . ?
C7 C4 C3 121.6(9) . . ?
C5 C4 C3 118.8(8) . . ?
C4 C5 C6 120.3(8) . . ?
C4 C5 C10 119.3(8) . . ?
C6 C5 C10 120.3(8) . . ?
C5 C6 C13 118.7(8) . . ?
C5 C6 C1 120.2(7) . . ?
C13 C6 C1 121.1(7) . . ?
C8 C7 C4 121.0(10) . . ?
C8 C7 H7A 119.5 . . ?
C4 C7 H7A 119.5 . . ?
C9 C8 C7 120.0(9) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C8 C9 C10 120.5(10) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C9 C10 C11 121.9(9) . . ?
C9 C10 C5 119.5(9) . . ?
C11 C10 C5 118.7(8) . . ?
C12 C11 C10 122.2(9) . . ?
C12 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
C11 C12 C13 120.8(9) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C6 117.9(8) . . ?
C14 C13 C12 122.8(9) . . ?
C6 C13 C12 119.3(8) . . ?
C15 C14 C13 121.4(9) . . ?
C15 C14 H14A 119.3 . . ?
C13 C14 H14A 119.3 . . ?
C14 C15 C16 121.8(9) . . ?
C14 C15 H15A 119.1 . . ?
C16 C15 H15A 119.1 . . ?
C15 C16 C1 119.0(8) . . ?
C15 C16 C17 119.2(8) . . ?
C1 C16 C17 121.8(8) . . ?
C18 C17 C16 129.1(8) . . ?
C18 C17 H17A 115.4 . . ?
C16 C17 H17A 115.4 . . ?
C17 C18 C19 121.8(8) . . ?
C17 C18 H18A 119.1 . . ?
C19 C18 H18A 119.1 . . ?
O C19 C18 120.7(9) . . ?
O C19 C20 119.9(9) . . ?
C18 C19 C20 119.4(7) . . ?
C25 C20 C21 118.1(8) . . ?
C25 C20 C19 118.7(8) . . ?
C21 C20 C19 123.2(8) . . ?
C20 C21 C22 120.8(8) . . ?
C20 C21 H21A 119.6 . . ?
C22 C21 H21A 119.6 . . ?
C23 C22 C21 118.7(8) . . ?
C23 C22 H22A 120.6 . . ?
C21 C22 H22A 120.6 . . ?
C24 C23 C22 121.6(9) . . ?
C24 C23 Cl 118.4(7) . . ?
C22 C23 Cl 120.0(7) . . ?
C23 C24 C25 119.1(9) . . ?
C23 C24 H24A 120.4 . . ?
C25 C24 H24A 120.4 . . ?
C20 C25 C24 121.4(8) . . ?
C20 C25 H25A 119.3 . . ?
C24 C25 H25A 119.3 . . ?

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
C16 C1 C2 C3 -179.7(8) . . . . ?
C6 C1 C2 C3 2.2(12) . . . . ?
C1 C2 C3 C4 -0.4(13) . . . . ?
C2 C3 C4 C7 178.1(9) . . . . ?
C2 C3 C4 C5 -0.8(13) . . . . ?
C7 C4 C5 C6 -178.8(8) . . . . ?
C3 C4 C5 C6 0.2(12) . . . . ?
C7 C4 C5 C10 2.2(12) . . . . ?
C3 C4 C5 C10 -178.9(8) . . . . ?
C4 C5 C6 C13 -178.8(8) . . . . ?
C10 C5 C6 C13 0.2(11) . . . . ?
C4 C5 C6 C1 1.6(11) . . . . ?
C10 C5 C6 C1 -179.3(7) . . . . ?
C16 C1 C6 C5 179.0(7) . . . . ?
C2 C1 C6 C5 -2.8(11) . . . . ?
C16 C1 C6 C13 -0.6(11) . . . . ?
C2 C1 C6 C13 177.7(7) . . . . ?
C5 C4 C7 C8 -0.8(14) . . . . ?
C3 C4 C7 C8 -179.7(9) . . . . ?
C4 C7 C8 C9 -0.7(15) . . . . ?
C7 C8 C9 C10 0.7(15) . . . . ?
C8 C9 C10 C11 180.0(9) . . . . ?
C8 C9 C10 C5 0.7(14) . . . . ?
C4 C5 C10 C9 -2.2(12) . . . . ?
C6 C5 C10 C9 178.8(8) . . . . ?
C4 C5 C10 C11 178.6(8) . . . . ?
C6 C5 C10 C11 -0.4(12) . . . . ?
C9 C10 C11 C12 -179.3(9) . . . . ?
C5 C10 C11 C12 -0.1(13) . . . . ?
C10 C11 C12 C13 0.9(14) . . . . ?
C5 C6 C13 C14 179.3(7) . . . . ?
C1 C6 C13 C14 -1.1(11) . . . . ?
C5 C6 C13 C12 0.5(11) . . . . ?
C1 C6 C13 C12 -179.9(7) . . . . ?
C11 C12 C13 C14 -179.8(9) . . . . ?
C11 C12 C13 C6 -1.0(12) . . . . ?
C6 C13 C14 C15 1.0(12) . . . . ?
C12 C13 C14 C15 179.7(8) . . . . ?
C13 C14 C15 C16 0.9(13) . . . . ?
C14 C15 C16 C1 -2.7(13) . . . . ?
C14 C15 C16 C17 175.0(8) . . . . ?
C6 C1 C16 C15 2.4(11) . . . . ?
C2 C1 C16 C15 -175.7(8) . . . . ?
C6 C1 C16 C17 -175.2(7) . . . . ?
C2 C1 C16 C17 6.7(12) . . . . ?
C15 C16 C17 C18 19.9(13) . . . . ?
C1 C16 C17 C18 -162.6(9) . . . . ?
C16 C17 C18 C19 -177.0(8) . . . . ?
C17 C18 C19 O 13.5(15) . . . . ?
C17 C18 C19 C20 -165.0(8) . . . . ?
O C19 C20 C25 11.7(14) . . . . ?
C18 C19 C20 C25 -169.9(9) . . . . ?
O C19 C20 C21 -165.1(9) . . . . ?
C18 C19 C20 C21 13.4(14) . . . . ?
C25 C20 C21 C22 -3.1(13) . . . . ?
C19 C20 C21 C22 173.6(8) . . . . ?
C20 C21 C22 C23 3.7(12) . . . . ?
C21 C22 C23 C24 -0.6(13) . . . . ?
C21 C22 C23 Cl 179.2(6) . . . . ?
C22 C23 C24 C25 -2.9(14) . . . . ?
Cl C23 C24 C25 177.3(7) . . . . ?
C21 C20 C25 C24 -0.5(14) . . . . ?
C19 C20 C25 C24 -177.4(9) . . . . ?
C23 C24 C25 C20 3.5(15) . . . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/dichloromethane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1473277'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ' 3-(9-anthryl)-1-(4-chloro) prop-2-en-1-one '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H30 Cl2 O2'
_chemical_formula_weight         685.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   10.831(2)
_cell_length_b                   10.431(2)
_cell_length_c                   30.703(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3468.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       rodlike
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4495
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.326
_diffrn_reflns_theta_max         25.373
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.707
_diffrn_reflns_point_group_measured_fraction_full 0.708
_reflns_number_total             4495
_reflns_number_gt                2360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.386
_reflns_Friedel_fraction_max     0.402
_reflns_Friedel_fraction_full    0.404

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0350P)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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.42(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4495
_refine_ls_number_parameters     451
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
Cl1 Cl 1.1180(3) -0.0635(3) 0.28942(10) 0.0931(9) Uani 1 1 d . . . . .
O1 O 0.8826(6) 0.5124(5) 0.2454(3) 0.072(2) Uani 1 1 d . . . . .
C1 C 0.9449(6) 0.6534(7) 0.1618(3) 0.049(2) Uani 1 1 d . . . . .
C2 C 0.8953(6) 0.7813(7) 0.1590(3) 0.051(2) Uani 1 1 d . . . . .
C3 C 0.9479(7) 0.8878(8) 0.1798(3) 0.062(2) Uani 1 1 d . . . . .
H3A H 1.0199 0.8764 0.1958 0.074 Uiso 1 1 calc R U . . .
C4 C 0.8983(12) 1.0055(9) 0.1773(4) 0.077(4) Uani 1 1 d . . . . .
H4A H 0.9360 1.0748 0.1910 0.092 Uiso 1 1 calc R U . . .
C5 C 0.7890(9) 1.0222(9) 0.1539(4) 0.073(3) Uani 1 1 d . . . . .
H5A H 0.7530 1.1031 0.1530 0.088 Uiso 1 1 calc R U . . .
C6 C 0.7334(7) 0.9243(8) 0.1323(3) 0.067(3) Uani 1 1 d . . . . .
H6A H 0.6616 0.9390 0.1164 0.080 Uiso 1 1 calc R U . . .
C7 C 0.7851(6) 0.8001(7) 0.1340(3) 0.051(2) Uani 1 1 d . . . . .
C8 C 0.7310(7) 0.6971(8) 0.1121(3) 0.060(2) Uani 1 1 d . . . . .
H8A H 0.6600 0.7124 0.0959 0.072 Uiso 1 1 calc R U . . .
C9 C 0.7775(7) 0.5733(8) 0.1132(3) 0.051(2) Uani 1 1 d . . . . .
C10 C 0.7216(10) 0.4728(9) 0.0904(4) 0.066(3) Uani 1 1 d . . . . .
H10A H 0.6509 0.4880 0.0741 0.079 Uiso 1 1 calc R U . . .
C11 C 0.7698(9) 0.3549(9) 0.0922(3) 0.075(3) Uani 1 1 d . . . . .
H11A H 0.7324 0.2883 0.0769 0.089 Uiso 1 1 calc R U . . .
C12 C 0.8797(8) 0.3300(8) 0.1177(3) 0.065(2) Uani 1 1 d . . . . .
H12A H 0.9114 0.2474 0.1195 0.078 Uiso 1 1 calc R U . . .
C13 C 0.9363(7) 0.4283(8) 0.1390(3) 0.063(3) Uani 1 1 d . . . . .
H13A H 1.0090 0.4127 0.1542 0.075 Uiso 1 1 calc R U . . .
C14 C 0.8875(7) 0.5515(8) 0.1384(3) 0.052(2) Uani 1 1 d . . . . .
C15 C 1.0601(7) 0.6368(7) 0.1867(3) 0.058(2) Uani 1 1 d . . . . .
H15A H 1.1258 0.6892 0.1788 0.070 Uiso 1 1 calc R U . . .
C16 C 1.0809(7) 0.5567(8) 0.2188(3) 0.058(2) Uani 1 1 d . . . . .
H16A H 1.1606 0.5521 0.2300 0.070 Uiso 1 1 calc R U . . .
C17 C 0.9877(8) 0.4752(8) 0.2378(3) 0.052(3) Uani 1 1 d . . . . .
C18 C 1.0225(6) 0.3421(7) 0.2518(3) 0.053(2) Uani 1 1 d . . . . .
C19 C 0.9417(7) 0.2678(8) 0.2760(3) 0.069(3) Uani 1 1 d . . . . .
H19A H 0.8663 0.3024 0.2845 0.083 Uiso 1 1 calc R U . . .
C20 C 0.9703(7) 0.1437(9) 0.2879(3) 0.076(2) Uani 1 1 d . . . . .
H20A H 0.9153 0.0959 0.3045 0.092 Uiso 1 1 calc R U . . .
C21 C 1.0806(8) 0.0914(8) 0.2748(3) 0.061(3) Uani 1 1 d . . . . .
C22 C 1.1620(7) 0.1664(8) 0.2506(3) 0.065(3) Uani 1 1 d . . . . .
H22A H 1.2374 0.1324 0.2419 0.078 Uiso 1 1 calc R U . . .
C23 C 1.1327(7) 0.2870(8) 0.2397(3) 0.069(3) Uani 1 1 d . . . . .
H23A H 1.1885 0.3348 0.2234 0.083 Uiso 1 1 calc R U . . .
Cl2 Cl 0.1361(3) 1.5577(3) 0.34201(10) 0.0944(10) Uani 1 1 d . . . . .
O2 O 0.3786(6) 0.9821(5) 0.3847(3) 0.074(2) Uani 1 1 d . . . . .
C24 C 0.3079(6) 0.8340(7) 0.4693(3) 0.0460(19) Uani 1 1 d . . . . .
C25 C 0.3604(6) 0.7129(7) 0.4728(3) 0.0495(19) Uani 1 1 d . . . . .
C26 C 0.3124(7) 0.6022(8) 0.4501(3) 0.067(3) Uani 1 1 d . . . . .
H26A H 0.2423 0.6109 0.4329 0.081 Uiso 1 1 calc R U . . .
C27 C 0.3664(10) 0.4882(7) 0.4534(5) 0.069(4) Uani 1 1 d . . . . .
H27A H 0.3318 0.4187 0.4389 0.083 Uiso 1 1 calc R U . . .
C28 C 0.4750(10) 0.4696(8) 0.4783(4) 0.079(4) Uani 1 1 d . . . . .
H28A H 0.5132 0.3898 0.4788 0.095 Uiso 1 1 calc R U . . .
C29 C 0.5230(7) 0.5685(7) 0.5013(3) 0.073(3) Uani 1 1 d . . . . .
H29A H 0.5920 0.5545 0.5187 0.087 Uiso 1 1 calc R U . . .
C30 C 0.4707(6) 0.6926(7) 0.4995(3) 0.058(2) Uani 1 1 d . . . . .
C31 C 0.5194(7) 0.7964(8) 0.5209(3) 0.057(2) Uani 1 1 d . . . . .
H31A H 0.5880 0.7851 0.5387 0.068 Uiso 1 1 calc R U . . .
C32 C 0.4690(7) 0.9172(8) 0.5166(3) 0.054(2) Uani 1 1 d . . . . .
C33 C 0.5231(9) 1.0264(10) 0.5368(4) 0.068(3) Uani 1 1 d . . . . .
H33A H 0.5931 1.0140 0.5538 0.082 Uiso 1 1 calc R U . . .
C34 C 0.4790(8) 1.1472(10) 0.5327(3) 0.069(3) Uani 1 1 d . . . . .
H34A H 0.5209 1.2164 0.5448 0.083 Uiso 1 1 calc R U . . .
C35 C 0.3669(8) 1.1654(8) 0.5095(3) 0.068(2) Uani 1 1 d . . . . .
H35A H 0.3323 1.2469 0.5077 0.081 Uiso 1 1 calc R U . . .
C36 C 0.3114(7) 1.0676(7) 0.4902(3) 0.051(2) Uani 1 1 d . . . . .
H36A H 0.2380 1.0835 0.4754 0.061 Uiso 1 1 calc R U . . .
C37 C 0.3587(6) 0.9347(8) 0.4908(3) 0.042(2) Uani 1 1 d . . . . .
C38 C 0.1956(6) 0.8504(7) 0.4422(3) 0.054(2) Uani 1 1 d . . . . .
H38A H 0.1295 0.7969 0.4489 0.065 Uiso 1 1 calc R U . . .
C39 C 0.1778(6) 0.9334(7) 0.4092(3) 0.057(2) Uani 1 1 d . . . . .
H39A H 0.0989 0.9378 0.3973 0.068 Uiso 1 1 calc R U . . .
C40 C 0.2751(9) 1.0197(8) 0.3900(4) 0.057(3) Uani 1 1 d . . . . .
C41 C 0.2359(6) 1.1529(7) 0.3788(3) 0.052(2) Uani 1 1 d . . . . .
C42 C 0.3155(6) 1.2296(7) 0.3547(3) 0.064(2) Uani 1 1 d . . . . .
H42A H 0.3914 1.1967 0.3460 0.076 Uiso 1 1 calc R U . . .
C43 C 0.2849(8) 1.3525(8) 0.3436(3) 0.078(3) Uani 1 1 d . . . . .
H43A H 0.3380 1.4024 0.3269 0.094 Uiso 1 1 calc R U . . .
C44 C 0.1730(9) 1.4005(8) 0.3577(3) 0.063(3) Uani 1 1 d . . . . .
C45 C 0.0942(7) 1.3322(8) 0.3805(3) 0.067(3) Uani 1 1 d . . . . .
H45A H 0.0189 1.3670 0.3890 0.081 Uiso 1 1 calc R U . . .
C46 C 0.1250(6) 1.2076(8) 0.3917(3) 0.062(2) Uani 1 1 d . . . . .
H46A H 0.0700 1.1594 0.4082 0.074 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
Cl1 C21 1.724(9) . ?
O1 C17 1.225(10) . ?
C1 C14 1.426(11) . ?
C1 C2 1.440(9) . ?
C1 C15 1.475(9) . ?
C2 C3 1.402(9) . ?
C2 C7 1.432(9) . ?
C3 C4 1.343(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(15) . ?
C4 H4A 0.9300 . ?
C5 C6 1.358(12) . ?
C5 H5A 0.9300 . ?
C6 C7 1.413(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.397(10) . ?
C8 C9 1.386(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.397(11) . ?
C9 C14 1.439(11) . ?
C10 C11 1.337(11) . ?
C10 H10A 0.9300 . ?
C11 C12 1.449(12) . ?
C11 H11A 0.9300 . ?
C12 C13 1.361(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.389(12) . ?
C13 H13A 0.9300 . ?
C15 C16 1.311(11) . ?
C15 H15A 0.9300 . ?
C16 C17 1.443(12) . ?
C16 H16A 0.9300 . ?
C17 C18 1.501(11) . ?
C18 C23 1.376(9) . ?
C18 C19 1.386(10) . ?
C19 C20 1.380(9) . ?
C19 H19A 0.9300 . ?
C20 C21 1.373(10) . ?
C20 H20A 0.9300 . ?
C21 C22 1.394(12) . ?
C22 C23 1.339(10) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?
Cl2 C44 1.756(8) . ?
O2 C40 1.199(11) . ?
C24 C37 1.357(9) . ?
C24 C25 1.389(9) . ?
C24 C38 1.483(9) . ?
C25 C26 1.445(10) . ?
C25 C30 1.464(9) . ?
C26 C27 1.328(10) . ?
C26 H26A 0.9300 . ?
C27 C28 1.416(16) . ?
C27 H27A 0.9300 . ?
C28 C29 1.355(13) . ?
C28 H28A 0.9300 . ?
C29 C30 1.413(9) . ?
C29 H29A 0.9300 . ?
C30 C31 1.371(10) . ?
C31 C32 1.379(10) . ?
C31 H31A 0.9300 . ?
C32 C33 1.423(12) . ?
C32 C37 1.444(10) . ?
C33 C34 1.354(12) . ?
C33 H33A 0.9300 . ?
C34 C35 1.422(11) . ?
C34 H34A 0.9300 . ?
C35 C36 1.323(10) . ?
C35 H35A 0.9300 . ?
C36 C37 1.479(11) . ?
C36 H36A 0.9300 . ?
C38 C39 1.347(11) . ?
C38 H38A 0.9300 . ?
C39 C40 1.507(11) . ?
C39 H39A 0.9300 . ?
C40 C41 1.493(10) . ?
C41 C46 1.387(9) . ?
C41 C42 1.389(9) . ?
C42 C43 1.367(9) . ?
C42 H42A 0.9300 . ?
C43 C44 1.381(11) . ?
C43 H43A 0.9300 . ?
C44 C45 1.314(11) . ?
C45 C46 1.385(10) . ?
C45 H45A 0.9300 . ?
C46 H46A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 119.9(7) . . ?
C14 C1 C15 122.9(7) . . ?
C2 C1 C15 117.1(7) . . ?
C3 C2 C7 118.3(7) . . ?
C3 C2 C1 123.7(7) . . ?
C7 C2 C1 118.0(7) . . ?
C4 C3 C2 122.4(9) . . ?
C4 C3 H3A 118.8 . . ?
C2 C3 H3A 118.8 . . ?
C3 C4 C5 118.8(10) . . ?
C3 C4 H4A 120.6 . . ?
C5 C4 H4A 120.6 . . ?
C6 C5 C4 122.3(9) . . ?
C6 C5 H5A 118.9 . . ?
C4 C5 H5A 118.9 . . ?
C5 C6 C7 119.7(8) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C8 C7 C6 121.4(8) . . ?
C8 C7 C2 120.2(7) . . ?
C6 C7 C2 118.4(7) . . ?
C9 C8 C7 123.5(8) . . ?
C9 C8 H8A 118.2 . . ?
C7 C8 H8A 118.2 . . ?
C8 C9 C10 122.0(9) . . ?
C8 C9 C14 117.5(8) . . ?
C10 C9 C14 120.6(8) . . ?
C11 C10 C9 120.1(10) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.4(9) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C13 C12 C11 119.7(8) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 121.3(8) . . ?
C12 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C13 C14 C1 121.2(8) . . ?
C13 C14 C9 117.9(8) . . ?
C1 C14 C9 120.9(8) . . ?
C16 C15 C1 127.6(7) . . ?
C16 C15 H15A 116.2 . . ?
C1 C15 H15A 116.2 . . ?
C15 C16 C17 124.0(8) . . ?
C15 C16 H16A 118.0 . . ?
C17 C16 H16A 118.0 . . ?
O1 C17 C16 122.7(8) . . ?
O1 C17 C18 118.2(9) . . ?
C16 C17 C18 119.0(7) . . ?
C23 C18 C19 117.3(8) . . ?
C23 C18 C17 121.8(8) . . ?
C19 C18 C17 120.8(7) . . ?
C20 C19 C18 121.6(7) . . ?
C20 C19 H19A 119.2 . . ?
C18 C19 H19A 119.2 . . ?
C21 C20 C19 119.4(8) . . ?
C21 C20 H20A 120.3 . . ?
C19 C20 H20A 120.3 . . ?
C20 C21 C22 118.8(8) . . ?
C20 C21 Cl1 120.1(8) . . ?
C22 C21 Cl1 121.1(7) . . ?
C23 C22 C21 120.7(8) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C18 122.0(8) . . ?
C22 C23 H23A 119.0 . . ?
C18 C23 H23A 119.0 . . ?
C37 C24 C25 120.0(7) . . ?
C37 C24 C38 121.1(7) . . ?
C25 C24 C38 118.9(7) . . ?
C24 C25 C26 122.9(7) . . ?
C24 C25 C30 120.6(7) . . ?
C26 C25 C30 116.6(7) . . ?
C27 C26 C25 121.4(9) . . ?
C27 C26 H26A 119.3 . . ?
C25 C26 H26A 119.3 . . ?
C26 C27 C28 121.9(10) . . ?
C26 C27 H27A 119.0 . . ?
C28 C27 H27A 119.0 . . ?
C29 C28 C27 119.7(9) . . ?
C29 C28 H28A 120.1 . . ?
C27 C28 H28A 120.1 . . ?
C28 C29 C30 121.6(9) . . ?
C28 C29 H29A 119.2 . . ?
C30 C29 H29A 119.2 . . ?
C31 C30 C29 123.4(8) . . ?
C31 C30 C25 117.9(7) . . ?
C29 C30 C25 118.8(8) . . ?
C30 C31 C32 121.6(7) . . ?
C30 C31 H31A 119.2 . . ?
C32 C31 H31A 119.2 . . ?
C31 C32 C33 121.8(8) . . ?
C31 C32 C37 119.7(8) . . ?
C33 C32 C37 118.5(8) . . ?
C34 C33 C32 124.1(9) . . ?
C34 C33 H33A 118.0 . . ?
C32 C33 H33A 118.0 . . ?
C33 C34 C35 118.2(9) . . ?
C33 C34 H34A 120.9 . . ?
C35 C34 H34A 120.9 . . ?
C36 C35 C34 120.6(8) . . ?
C36 C35 H35A 119.7 . . ?
C34 C35 H35A 119.7 . . ?
C35 C36 C37 124.1(8) . . ?
C35 C36 H36A 118.0 . . ?
C37 C36 H36A 118.0 . . ?
C24 C37 C32 120.3(7) . . ?
C24 C37 C36 125.4(7) . . ?
C32 C37 C36 114.4(7) . . ?
C39 C38 C24 127.8(7) . . ?
C39 C38 H38A 116.1 . . ?
C24 C38 H38A 116.1 . . ?
C38 C39 C40 125.4(7) . . ?
C38 C39 H39A 117.3 . . ?
C40 C39 H39A 117.3 . . ?
O2 C40 C41 122.6(8) . . ?
O2 C40 C39 120.8(8) . . ?
C41 C40 C39 116.6(7) . . ?
C46 C41 C42 116.9(7) . . ?
C46 C41 C40 124.3(8) . . ?
C42 C41 C40 118.8(7) . . ?
C43 C42 C41 121.5(7) . . ?
C43 C42 H42A 119.2 . . ?
C41 C42 H42A 119.2 . . ?
C42 C43 C44 118.3(8) . . ?
C42 C43 H43A 120.9 . . ?
C44 C43 H43A 120.9 . . ?
C45 C44 C43 122.7(8) . . ?
C45 C44 Cl2 120.3(7) . . ?
C43 C44 Cl2 116.9(7) . . ?
C44 C45 C46 119.0(8) . . ?
C44 C45 H45A 120.5 . . ?
C46 C45 H45A 120.5 . . ?
C45 C46 C41 121.6(8) . . ?
C45 C46 H46A 119.2 . . ?
C41 C46 H46A 119.2 . . ?

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 C3 -178.0(8) . . . . ?
C15 C1 C2 C3 -2.3(10) . . . . ?
C14 C1 C2 C7 2.8(10) . . . . ?
C15 C1 C2 C7 178.5(7) . . . . ?
C7 C2 C3 C4 0.6(12) . . . . ?
C1 C2 C3 C4 -178.7(9) . . . . ?
C2 C3 C4 C5 1.1(16) . . . . ?
C3 C4 C5 C6 -2.2(18) . . . . ?
C4 C5 C6 C7 1.4(16) . . . . ?
C5 C6 C7 C8 -179.6(9) . . . . ?
C5 C6 C7 C2 0.4(12) . . . . ?
C3 C2 C7 C8 178.7(7) . . . . ?
C1 C2 C7 C8 -2.0(10) . . . . ?
C3 C2 C7 C6 -1.3(10) . . . . ?
C1 C2 C7 C6 178.0(7) . . . . ?
C6 C7 C8 C9 -179.3(8) . . . . ?
C2 C7 C8 C9 0.7(12) . . . . ?
C7 C8 C9 C10 -179.4(9) . . . . ?
C7 C8 C9 C14 0.0(12) . . . . ?
C8 C9 C10 C11 179.7(10) . . . . ?
C14 C9 C10 C11 0.4(15) . . . . ?
C9 C10 C11 C12 0.3(16) . . . . ?
C10 C11 C12 C13 -2.0(15) . . . . ?
C11 C12 C13 C14 3.1(13) . . . . ?
C12 C13 C14 C1 178.1(9) . . . . ?
C12 C13 C14 C9 -2.4(12) . . . . ?
C2 C1 C14 C13 177.3(7) . . . . ?
C15 C1 C14 C13 1.8(12) . . . . ?
C2 C1 C14 C9 -2.2(12) . . . . ?
C15 C1 C14 C9 -177.7(7) . . . . ?
C8 C9 C14 C13 -178.7(8) . . . . ?
C10 C9 C14 C13 0.7(12) . . . . ?
C8 C9 C14 C1 0.8(11) . . . . ?
C10 C9 C14 C1 -179.8(9) . . . . ?
C14 C1 C15 C16 -57.9(13) . . . . ?
C2 C1 C15 C16 126.5(9) . . . . ?
C1 C15 C16 C17 -5.0(14) . . . . ?
C15 C16 C17 O1 -41.7(15) . . . . ?
C15 C16 C17 C18 142.6(9) . . . . ?
O1 C17 C18 C23 171.5(9) . . . . ?
C16 C17 C18 C23 -12.6(13) . . . . ?
O1 C17 C18 C19 -5.7(13) . . . . ?
C16 C17 C18 C19 170.2(8) . . . . ?
C23 C18 C19 C20 0.5(13) . . . . ?
C17 C18 C19 C20 177.7(8) . . . . ?
C18 C19 C20 C21 -1.1(13) . . . . ?
C19 C20 C21 C22 1.2(13) . . . . ?
C19 C20 C21 Cl1 179.9(7) . . . . ?
C20 C21 C22 C23 -0.8(14) . . . . ?
Cl1 C21 C22 C23 -179.5(8) . . . . ?
C21 C22 C23 C18 0.2(15) . . . . ?
C19 C18 C23 C22 0.0(14) . . . . ?
C17 C18 C23 C22 -177.3(9) . . . . ?
C37 C24 C25 C26 -178.8(8) . . . . ?
C38 C24 C25 C26 1.8(11) . . . . ?
C37 C24 C25 C30 0.0(11) . . . . ?
C38 C24 C25 C30 -179.4(7) . . . . ?
C24 C25 C26 C27 178.5(9) . . . . ?
C30 C25 C26 C27 -0.3(12) . . . . ?
C25 C26 C27 C28 -1.5(17) . . . . ?
C26 C27 C28 C29 3.3(19) . . . . ?
C27 C28 C29 C30 -3.1(16) . . . . ?
C28 C29 C30 C31 -177.2(9) . . . . ?
C28 C29 C30 C25 1.3(13) . . . . ?
C24 C25 C30 C31 0.2(11) . . . . ?
C26 C25 C30 C31 179.1(7) . . . . ?
C24 C25 C30 C29 -178.5(8) . . . . ?
C26 C25 C30 C29 0.4(11) . . . . ?
C29 C30 C31 C32 176.7(8) . . . . ?
C25 C30 C31 C32 -1.8(12) . . . . ?
C30 C31 C32 C33 -176.6(9) . . . . ?
C30 C31 C32 C37 3.2(12) . . . . ?
C31 C32 C33 C34 178.4(10) . . . . ?
C37 C32 C33 C34 -1.4(15) . . . . ?
C32 C33 C34 C35 4.7(16) . . . . ?
C33 C34 C35 C36 -3.8(14) . . . . ?
C34 C35 C36 C37 -0.3(13) . . . . ?
C25 C24 C37 C32 1.4(11) . . . . ?
C38 C24 C37 C32 -179.2(7) . . . . ?
C25 C24 C37 C36 -179.4(7) . . . . ?
C38 C24 C37 C36 0.1(12) . . . . ?
C31 C32 C37 C24 -3.0(12) . . . . ?
C33 C32 C37 C24 176.8(8) . . . . ?
C31 C32 C37 C36 177.7(7) . . . . ?
C33 C32 C37 C36 -2.6(11) . . . . ?
C35 C36 C37 C24 -175.9(9) . . . . ?
C35 C36 C37 C32 3.4(11) . . . . ?
C37 C24 C38 C39 54.8(12) . . . . ?
C25 C24 C38 C39 -125.8(9) . . . . ?
C24 C38 C39 C40 6.3(14) . . . . ?
C38 C39 C40 O2 39.7(16) . . . . ?
C38 C39 C40 C41 -139.3(9) . . . . ?
O2 C40 C41 C46 -167.4(10) . . . . ?
C39 C40 C41 C46 11.6(14) . . . . ?
O2 C40 C41 C42 11.1(16) . . . . ?
C39 C40 C41 C42 -169.9(8) . . . . ?
C46 C41 C42 C43 -1.2(12) . . . . ?
C40 C41 C42 C43 -179.9(9) . . . . ?
C41 C42 C43 C44 1.5(13) . . . . ?
C42 C43 C44 C45 -1.5(15) . . . . ?
C42 C43 C44 Cl2 -179.0(6) . . . . ?
C43 C44 C45 C46 1.3(15) . . . . ?
Cl2 C44 C45 C46 178.7(7) . . . . ?
C44 C45 C46 C41 -1.0(14) . . . . ?
C42 C41 C46 C45 0.9(13) . . . . ?
C40 C41 C46 C45 179.5(9) . . . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1473285'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ' 1-phenyl-3-(1-pyrenyl) prop-2-en-1-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 O'
_chemical_formula_weight         332.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.6720(9)
_cell_length_b                   22.405(5)
_cell_length_c                   8.2100(16)
_cell_angle_alpha                90
_cell_angle_beta                 106.02(3)
_cell_angle_gamma                90
_cell_volume                     826.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       needlelike
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1745
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         25.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.513
_diffrn_reflns_point_group_measured_fraction_full 0.514
_reflns_number_total             1553
_reflns_number_gt                809
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0450P)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 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   1(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1553
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O O 0.2888(11) -0.1548(2) 0.3843(6) 0.0956(17) Uani 1 1 d . . . . .
C1 C -0.1997(14) -0.1939(3) 0.1286(7) 0.0700(19) Uani 1 1 d . . . . .
H1A H -0.1828 -0.2077 0.2377 0.084 Uiso 1 1 calc R U . . .
C2 C -0.4107(16) -0.2192(3) -0.0081(10) 0.082(2) Uani 1 1 d . . . . .
H2A H -0.5374 -0.2489 0.0100 0.098 Uiso 1 1 calc R U . . .
C3 C -0.4309(16) -0.1997(4) -0.1724(9) 0.083(2) Uani 1 1 d . . . . .
H3A H -0.5662 -0.2169 -0.2653 0.100 Uiso 1 1 calc R U . . .
C4 C -0.2547(17) -0.1565(3) -0.1927(8) 0.085(2) Uani 1 1 d . . . . .
H4A H -0.2727 -0.1430 -0.3022 0.102 Uiso 1 1 calc R U . . .
C5 C -0.0408(16) -0.1293(3) -0.0592(7) 0.073(2) Uani 1 1 d . . . . .
H5A H 0.0817 -0.0990 -0.0787 0.087 Uiso 1 1 calc R U . . .
C6 C -0.0195(13) -0.1497(3) 0.1042(7) 0.0563(17) Uani 1 1 d . . . . .
C7 C 0.2152(15) -0.1248(3) 0.2542(9) 0.066(2) Uani 1 1 d . . . . .
C8 C 0.3456(15) -0.0672(3) 0.2433(7) 0.0631(19) Uani 1 1 d . . . . .
H8A H 0.2612 -0.0434 0.1495 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5799(13) -0.0465(3) 0.3602(7) 0.0560(17) Uani 1 1 d . . . . .
H9A H 0.6660 -0.0728 0.4476 0.067 Uiso 1 1 calc R U . . .
C10 C 0.7211(13) 0.0119(3) 0.3704(7) 0.0522(16) Uani 1 1 d . . . . .
C11 C 0.5811(15) 0.0575(3) 0.2582(7) 0.0623(19) Uani 1 1 d . . . . .
H11A H 0.4037 0.0495 0.1762 0.075 Uiso 1 1 calc R U . . .
C12 C 0.7014(14) 0.1128(3) 0.2683(8) 0.0616(18) Uani 1 1 d . . . . .
H12A H 0.6037 0.1415 0.1910 0.074 Uiso 1 1 calc R U . . .
C13 C 0.9602(14) 0.1286(2) 0.3867(7) 0.0551(17) Uani 1 1 d . . . . .
C14 C 1.1031(12) 0.0839(3) 0.5059(7) 0.0489(16) Uani 1 1 d . . . . .
C15 C 1.0903(15) 0.1854(3) 0.4011(8) 0.0620(18) Uani 1 1 d . . . . .
H15A H 1.0008 0.2146 0.3230 0.074 Uiso 1 1 calc R U . . .
C16 C 1.3371(15) 0.1996(3) 0.5219(8) 0.072(2) Uani 1 1 d . . . . .
H16A H 1.4079 0.2385 0.5274 0.086 Uiso 1 1 calc R U . . .
C17 C 1.4952(15) 0.1573(3) 0.6422(8) 0.0607(17) Uani 1 1 d . . . . .
C18 C 1.3685(13) 0.0995(3) 0.6330(7) 0.0509(16) Uani 1 1 d . . . . .
C19 C 1.7558(15) 0.1708(3) 0.7662(9) 0.074(2) Uani 1 1 d . . . . .
H19A H 1.8374 0.2088 0.7719 0.088 Uiso 1 1 calc R U . . .
C20 C 1.8934(17) 0.1277(4) 0.8808(9) 0.079(2) Uani 1 1 d . . . . .
H20A H 2.0665 0.1376 0.9640 0.095 Uiso 1 1 calc R U . . .
C21 C 1.7863(15) 0.0721(4) 0.8763(8) 0.077(2) Uani 1 1 d . . . . .
H21A H 1.8864 0.0439 0.9548 0.092 Uiso 1 1 calc R U . . .
C22 C 1.5225(13) 0.0561(3) 0.7529(7) 0.0581(18) Uani 1 1 d . . . . .
C23 C 1.3924(13) -0.0025(3) 0.7406(8) 0.0633(18) Uani 1 1 d . . . . .
H23A H 1.4840 -0.0314 0.8190 0.076 Uiso 1 1 calc R U . . .
C24 C 1.1460(13) -0.0168(3) 0.6211(7) 0.0540(16) Uani 1 1 d . . . . .
H24A H 1.0754 -0.0558 0.6167 0.065 Uiso 1 1 calc R U . . .
C25 C 0.9844(14) 0.0256(3) 0.4984(7) 0.0510(15) 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
O C7 1.227(8) . ?
C1 C6 1.351(8) . ?
C1 C2 1.393(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.397(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.311(9) . ?
C3 H3A 0.9300 . ?
C4 C5 1.402(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.394(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.511(7) . ?
C7 C8 1.441(8) . ?
C8 C9 1.325(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.457(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.410(7) . ?
C10 C25 1.414(7) . ?
C11 C12 1.352(8) . ?
C11 H11A 0.9300 . ?
C12 C13 1.373(8) . ?
C12 H12A 0.9300 . ?
C13 C15 1.401(7) . ?
C13 C14 1.431(7) . ?
C14 C25 1.412(8) . ?
C14 C18 1.427(7) . ?
C15 C16 1.334(8) . ?
C15 H15A 0.9300 . ?
C16 C17 1.419(9) . ?
C16 H16A 0.9300 . ?
C17 C19 1.387(8) . ?
C17 C18 1.418(9) . ?
C18 C22 1.428(8) . ?
C19 C20 1.377(8) . ?
C19 H19A 0.9300 . ?
C20 C21 1.341(9) . ?
C20 H20A 0.9300 . ?
C21 C22 1.408(8) . ?
C21 H21A 0.9300 . ?
C22 C23 1.439(8) . ?
C23 C24 1.329(7) . ?
C23 H23A 0.9300 . ?
C24 C25 1.439(7) . ?
C24 H24A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.7(6) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
C1 C2 C3 119.7(7) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 C2 118.5(6) . . ?
C4 C3 H3A 120.8 . . ?
C2 C3 H3A 120.8 . . ?
C3 C4 C5 123.9(7) . . ?
C3 C4 H4A 118.0 . . ?
C5 C4 H4A 118.0 . . ?
C6 C5 C4 117.2(7) . . ?
C6 C5 H5A 121.4 . . ?
C4 C5 H5A 121.4 . . ?
C1 C6 C5 120.1(5) . . ?
C1 C6 C7 119.4(6) . . ?
C5 C6 C7 120.4(6) . . ?
O C7 C8 121.5(6) . . ?
O C7 C6 118.3(6) . . ?
C8 C7 C6 120.2(6) . . ?
C9 C8 C7 123.2(5) . . ?
C9 C8 H8A 118.4 . . ?
C7 C8 H8A 118.4 . . ?
C8 C9 C10 128.8(5) . . ?
C8 C9 H9A 115.6 . . ?
C10 C9 H9A 115.6 . . ?
C11 C10 C25 118.6(6) . . ?
C11 C10 C9 119.5(5) . . ?
C25 C10 C9 121.7(5) . . ?
C12 C11 C10 120.9(6) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C11 C12 C13 123.4(6) . . ?
C11 C12 H12A 118.3 . . ?
C13 C12 H12A 118.3 . . ?
C12 C13 C15 124.9(6) . . ?
C12 C13 C14 117.1(6) . . ?
C15 C13 C14 118.0(5) . . ?
C25 C14 C18 120.7(5) . . ?
C25 C14 C13 121.0(5) . . ?
C18 C14 C13 118.4(5) . . ?
C16 C15 C13 122.9(6) . . ?
C16 C15 H15A 118.5 . . ?
C13 C15 H15A 118.5 . . ?
C15 C16 C17 122.4(6) . . ?
C15 C16 H16A 118.8 . . ?
C17 C16 H16A 118.8 . . ?
C19 C17 C18 120.4(6) . . ?
C19 C17 C16 123.3(7) . . ?
C18 C17 C16 116.3(5) . . ?
C17 C18 C14 121.9(5) . . ?
C17 C18 C22 117.5(5) . . ?
C14 C18 C22 120.5(5) . . ?
C20 C19 C17 120.0(7) . . ?
C20 C19 H19A 120.0 . . ?
C17 C19 H19A 120.0 . . ?
C21 C20 C19 122.2(7) . . ?
C21 C20 H20A 118.9 . . ?
C19 C20 H20A 118.9 . . ?
C20 C21 C22 120.1(7) . . ?
C20 C21 H21A 120.0 . . ?
C22 C21 H21A 120.0 . . ?
C21 C22 C18 119.8(6) . . ?
C21 C22 C23 123.4(6) . . ?
C18 C22 C23 116.7(5) . . ?
C24 C23 C22 122.3(6) . . ?
C24 C23 H23A 118.8 . . ?
C22 C23 H23A 118.8 . . ?
C23 C24 C25 122.5(6) . . ?
C23 C24 H24A 118.7 . . ?
C25 C24 H24A 118.7 . . ?
C14 C25 C10 118.9(5) . . ?
C14 C25 C24 117.1(5) . . ?
C10 C25 C24 123.9(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
C6 C1 C2 C3 1.7(11) . . . . ?
C1 C2 C3 C4 -2.0(11) . . . . ?
C2 C3 C4 C5 1.5(12) . . . . ?
C3 C4 C5 C6 -0.7(11) . . . . ?
C2 C1 C6 C5 -0.8(10) . . . . ?
C2 C1 C6 C7 -177.6(6) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C4 C5 C6 C7 177.1(6) . . . . ?
C1 C6 C7 O 18.7(9) . . . . ?
C5 C6 C7 O -158.1(7) . . . . ?
C1 C6 C7 C8 -160.9(7) . . . . ?
C5 C6 C7 C8 22.3(9) . . . . ?
O C7 C8 C9 10.2(11) . . . . ?
C6 C7 C8 C9 -170.2(6) . . . . ?
C7 C8 C9 C10 -175.6(6) . . . . ?
C8 C9 C10 C11 9.4(10) . . . . ?
C8 C9 C10 C25 -175.5(7) . . . . ?
C25 C10 C11 C12 2.5(9) . . . . ?
C9 C10 C11 C12 177.7(6) . . . . ?
C10 C11 C12 C13 -0.9(10) . . . . ?
C11 C12 C13 C15 -179.8(6) . . . . ?
C11 C12 C13 C14 -1.0(9) . . . . ?
C12 C13 C14 C25 1.3(8) . . . . ?
C15 C13 C14 C25 -179.8(5) . . . . ?
C12 C13 C14 C18 -178.5(5) . . . . ?
C15 C13 C14 C18 0.4(8) . . . . ?
C12 C13 C15 C16 177.6(7) . . . . ?
C14 C13 C15 C16 -1.1(9) . . . . ?
C13 C15 C16 C17 2.6(10) . . . . ?
C15 C16 C17 C19 178.5(6) . . . . ?
C15 C16 C17 C18 -3.1(10) . . . . ?
C19 C17 C18 C14 -179.1(5) . . . . ?
C16 C17 C18 C14 2.4(9) . . . . ?
C19 C17 C18 C22 -1.3(9) . . . . ?
C16 C17 C18 C22 -179.8(6) . . . . ?
C25 C14 C18 C17 179.1(6) . . . . ?
C13 C14 C18 C17 -1.1(8) . . . . ?
C25 C14 C18 C22 1.3(7) . . . . ?
C13 C14 C18 C22 -178.9(6) . . . . ?
C18 C17 C19 C20 0.3(10) . . . . ?
C16 C17 C19 C20 178.7(6) . . . . ?
C17 C19 C20 C21 0.8(11) . . . . ?
C19 C20 C21 C22 -0.8(11) . . . . ?
C20 C21 C22 C18 -0.3(10) . . . . ?
C20 C21 C22 C23 -179.6(7) . . . . ?
C17 C18 C22 C21 1.3(9) . . . . ?
C14 C18 C22 C21 179.2(5) . . . . ?
C17 C18 C22 C23 -179.3(5) . . . . ?
C14 C18 C22 C23 -1.5(8) . . . . ?
C21 C22 C23 C24 -178.8(6) . . . . ?
C18 C22 C23 C24 1.9(9) . . . . ?
C22 C23 C24 C25 -2.2(10) . . . . ?
C18 C14 C25 C10 -180.0(6) . . . . ?
C13 C14 C25 C10 0.2(8) . . . . ?
C18 C14 C25 C24 -1.4(7) . . . . ?
C13 C14 C25 C24 178.8(6) . . . . ?
C11 C10 C25 C14 -2.1(8) . . . . ?
C9 C10 C25 C14 -177.3(5) . . . . ?
C11 C10 C25 C24 179.4(6) . . . . ?
C9 C10 C25 C24 4.3(9) . . . . ?
C23 C24 C25 C14 1.8(9) . . . . ?
C23 C24 C25 C10 -179.7(6) . . . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile/chloroform'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1473283'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'3-(1-pyrenyl)-1-(4-chlorophenyl) prop-2-en-1-one '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H15 Cl O'
_chemical_formula_weight         366.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   30.665(6)
_cell_length_b                   5.5070(11)
_cell_length_c                   21.295(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.38(3)
_cell_angle_gamma                90
_cell_volume                     3593.0(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       plate
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3365
_diffrn_reflns_av_unetI/netI     0.1247
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.329
_diffrn_reflns_theta_max         25.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3299
_reflns_number_gt                1347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.1060P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3299
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2216
_refine_ls_R_factor_gt           0.0986
_refine_ls_wR_factor_ref         0.2764
_refine_ls_wR_factor_gt          0.2173
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Cl Cl 0.25600(6) 0.0797(4) 0.13824(9) 0.0849(8) Uani 1 1 d . . . . .
O O 0.40993(16) 0.4565(8) 0.3443(2) 0.0800(17) Uani 1 1 d . . . . .
C1 C 0.54479(18) -0.0145(10) 0.4265(2) 0.0416(14) Uani 1 1 d . . . . .
C2 C 0.54237(19) 0.1712(11) 0.4720(3) 0.0454(14) Uani 1 1 d . . . . .
H2A H 0.5181 0.2730 0.4705 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5738(2) 0.2073(12) 0.5175(3) 0.0587(18) Uani 1 1 d . . . . .
H3A H 0.5707 0.3324 0.5463 0.070 Uiso 1 1 calc R U . . .
C4 C 0.6108(2) 0.0588(13) 0.5218(3) 0.0549(17) Uani 1 1 d . . . . .
C5 C 0.61397(18) -0.1359(12) 0.4776(3) 0.0517(16) Uani 1 1 d . . . . .
C6 C 0.58119(17) -0.1769(11) 0.4303(3) 0.0472(15) Uani 1 1 d . . . . .
C7 C 0.6445(2) 0.0873(13) 0.5685(3) 0.0656(19) Uani 1 1 d . . . . .
H7A H 0.6425 0.2087 0.5986 0.079 Uiso 1 1 calc R U . . .
C8 C 0.6808(2) -0.0670(16) 0.5695(4) 0.080(2) Uani 1 1 d . . . . .
H8A H 0.7032 -0.0419 0.5995 0.096 Uiso 1 1 calc R U . . .
C9 C 0.6842(2) -0.2513(15) 0.5281(3) 0.071(2) Uani 1 1 d . . . . .
H9A H 0.7082 -0.3543 0.5308 0.086 Uiso 1 1 calc R U . . .
C10 C 0.6514(2) -0.2873(13) 0.4811(3) 0.0590(18) Uani 1 1 d . . . . .
C11 C 0.6536(2) -0.4872(13) 0.4372(3) 0.0622(19) Uani 1 1 d . . . . .
H11A H 0.6776 -0.5907 0.4401 0.075 Uiso 1 1 calc R U . . .
C12 C 0.6230(2) -0.5275(13) 0.3937(3) 0.0640(19) Uani 1 1 d . . . . .
H12A H 0.6257 -0.6576 0.3663 0.077 Uiso 1 1 calc R U . . .
C13 C 0.5850(2) -0.3718(11) 0.3878(3) 0.0531(16) Uani 1 1 d . . . . .
C14 C 0.5531(2) -0.4102(12) 0.3431(3) 0.0572(17) Uani 1 1 d . . . . .
H14A H 0.5553 -0.5405 0.3157 0.069 Uiso 1 1 calc R U . . .
C15 C 0.51758(18) -0.2587(12) 0.3379(3) 0.0526(16) Uani 1 1 d . . . . .
H15A H 0.4958 -0.2900 0.3072 0.063 Uiso 1 1 calc R U . . .
C16 C 0.51337(19) -0.0592(11) 0.3775(3) 0.0457(14) Uani 1 1 d . . . . .
C17 C 0.4758(2) 0.1118(12) 0.3659(3) 0.0544(16) Uani 1 1 d . . . . .
H17A H 0.4772 0.2575 0.3879 0.065 Uiso 1 1 calc R U . . .
C18 C 0.4419(2) 0.0808(13) 0.3290(3) 0.0613(18) Uani 1 1 d . . . . .
H18A H 0.4394 -0.0646 0.3069 0.074 Uiso 1 1 calc R U . . .
C19 C 0.4066(2) 0.2608(12) 0.3195(3) 0.0549(16) Uani 1 1 d . . . . .
C20 C 0.36899(18) 0.1980(10) 0.2749(3) 0.0444(14) Uani 1 1 d . . . . .
C21 C 0.3668(2) -0.0060(12) 0.2384(3) 0.069(2) Uani 1 1 d . . . . .
H21A H 0.3887 -0.1225 0.2426 0.083 Uiso 1 1 calc R U . . .
C22 C 0.3327(2) -0.0409(12) 0.1957(3) 0.068(2) Uani 1 1 d . . . . .
H22A H 0.3322 -0.1741 0.1688 0.082 Uiso 1 1 calc R U . . .
C23 C 0.29948(19) 0.1249(13) 0.1935(3) 0.0545(17) Uani 1 1 d . . . . .
C24 C 0.2996(2) 0.3282(14) 0.2290(3) 0.067(2) Uani 1 1 d . . . . .
H24A H 0.2768 0.4397 0.2253 0.081 Uiso 1 1 calc R U . . .
C25 C 0.3347(2) 0.3655(12) 0.2714(3) 0.0612(18) Uani 1 1 d . . . . .
H25A H 0.3354 0.5014 0.2974 0.073 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
Cl C23 1.759(6) . ?
O C19 1.203(7) . ?
C1 C16 1.412(7) . ?
C1 C2 1.412(7) . ?
C1 C6 1.430(7) . ?
C2 C3 1.352(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.400(8) . ?
C3 H3A 0.9300 . ?
C4 C7 1.411(8) . ?
C4 C5 1.433(9) . ?
C5 C6 1.412(8) . ?
C5 C10 1.418(8) . ?
C6 C13 1.412(8) . ?
C7 C8 1.400(10) . ?
C7 H7A 0.9300 . ?
C8 C9 1.351(10) . ?
C8 H8A 0.9300 . ?
C9 C10 1.402(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.447(10) . ?
C11 C12 1.311(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.446(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.353(8) . ?
C14 C15 1.373(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.395(8) . ?
C15 H15A 0.9300 . ?
C16 C17 1.500(8) . ?
C17 C18 1.290(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.475(8) . ?
C18 H18A 0.9300 . ?
C19 C20 1.503(8) . ?
C20 C21 1.366(8) . ?
C20 C25 1.397(8) . ?
C21 C22 1.370(8) . ?
C21 H21A 0.9300 . ?
C22 C23 1.368(9) . ?
C22 H22A 0.9300 . ?
C23 C24 1.351(9) . ?
C24 C25 1.393(8) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?

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
C16 C1 C2 125.4(6) . . ?
C16 C1 C6 116.1(5) . . ?
C2 C1 C6 118.5(5) . . ?
C3 C2 C1 122.8(6) . . ?
C3 C2 H2A 118.6 . . ?
C1 C2 H2A 118.6 . . ?
C2 C3 C4 120.9(6) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C7 123.4(6) . . ?
C3 C4 C5 118.0(5) . . ?
C7 C4 C5 118.6(6) . . ?
C6 C5 C10 119.6(6) . . ?
C6 C5 C4 121.6(6) . . ?
C10 C5 C4 118.9(6) . . ?
C13 C6 C5 120.2(6) . . ?
C13 C6 C1 121.7(5) . . ?
C5 C6 C1 118.1(6) . . ?
C8 C7 C4 120.1(7) . . ?
C8 C7 H7A 119.9 . . ?
C4 C7 H7A 119.9 . . ?
C9 C8 C7 121.9(6) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C8 C9 C10 120.0(7) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C5 120.5(7) . . ?
C9 C10 C11 121.1(7) . . ?
C5 C10 C11 118.3(6) . . ?
C12 C11 C10 122.2(6) . . ?
C12 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
C11 C12 C13 120.8(7) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C6 119.5(6) . . ?
C14 C13 C12 121.6(6) . . ?
C6 C13 C12 118.9(6) . . ?
C13 C14 C15 120.7(6) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C14 C15 C16 121.5(5) . . ?
C14 C15 H15A 119.2 . . ?
C16 C15 H15A 119.2 . . ?
C15 C16 C1 120.4(5) . . ?
C15 C16 C17 119.0(5) . . ?
C1 C16 C17 120.6(5) . . ?
C18 C17 C16 127.8(6) . . ?
C18 C17 H17A 116.1 . . ?
C16 C17 H17A 116.1 . . ?
C17 C18 C19 124.3(6) . . ?
C17 C18 H18A 117.8 . . ?
C19 C18 H18A 117.8 . . ?
O C19 C18 119.6(6) . . ?
O C19 C20 122.2(6) . . ?
C18 C19 C20 118.1(6) . . ?
C21 C20 C25 119.6(6) . . ?
C21 C20 C19 124.5(6) . . ?
C25 C20 C19 115.9(6) . . ?
C20 C21 C22 120.8(6) . . ?
C20 C21 H21A 119.6 . . ?
C22 C21 H21A 119.6 . . ?
C23 C22 C21 118.4(6) . . ?
C23 C22 H22A 120.8 . . ?
C21 C22 H22A 120.8 . . ?
C24 C23 C22 123.4(6) . . ?
C24 C23 Cl 118.4(5) . . ?
C22 C23 Cl 118.1(5) . . ?
C23 C24 C25 118.0(6) . . ?
C23 C24 H24A 121.0 . . ?
C25 C24 H24A 121.0 . . ?
C24 C25 C20 119.8(6) . . ?
C24 C25 H25A 120.1 . . ?
C20 C25 H25A 120.1 . . ?

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
C16 C1 C2 C3 -179.2(6) . . . . ?
C6 C1 C2 C3 2.5(9) . . . . ?
C1 C2 C3 C4 -0.2(10) . . . . ?
C2 C3 C4 C7 -179.7(6) . . . . ?
C2 C3 C4 C5 -1.5(9) . . . . ?
C3 C4 C5 C6 0.9(9) . . . . ?
C7 C4 C5 C6 179.1(6) . . . . ?
C3 C4 C5 C10 179.6(6) . . . . ?
C7 C4 C5 C10 -2.1(8) . . . . ?
C10 C5 C6 C13 1.9(9) . . . . ?
C4 C5 C6 C13 -179.4(6) . . . . ?
C10 C5 C6 C1 -177.4(5) . . . . ?
C4 C5 C6 C1 1.4(8) . . . . ?
C16 C1 C6 C13 -0.7(8) . . . . ?
C2 C1 C6 C13 177.8(6) . . . . ?
C16 C1 C6 C5 178.6(5) . . . . ?
C2 C1 C6 C5 -3.0(8) . . . . ?
C3 C4 C7 C8 -179.4(7) . . . . ?
C5 C4 C7 C8 2.4(10) . . . . ?
C4 C7 C8 C9 -2.5(12) . . . . ?
C7 C8 C9 C10 2.2(12) . . . . ?
C8 C9 C10 C5 -1.9(11) . . . . ?
C8 C9 C10 C11 -178.3(7) . . . . ?
C6 C5 C10 C9 -179.4(6) . . . . ?
C4 C5 C10 C9 1.9(8) . . . . ?
C6 C5 C10 C11 -2.9(8) . . . . ?
C4 C5 C10 C11 178.4(6) . . . . ?
C9 C10 C11 C12 178.6(7) . . . . ?
C5 C10 C11 C12 2.1(9) . . . . ?
C10 C11 C12 C13 -0.3(10) . . . . ?
C5 C6 C13 C14 179.3(5) . . . . ?
C1 C6 C13 C14 -1.5(10) . . . . ?
C5 C6 C13 C12 -0.1(9) . . . . ?
C1 C6 C13 C12 179.2(5) . . . . ?
C11 C12 C13 C14 179.9(6) . . . . ?
C11 C12 C13 C6 -0.8(10) . . . . ?
C6 C13 C14 C15 1.4(10) . . . . ?
C12 C13 C14 C15 -179.3(6) . . . . ?
C13 C14 C15 C16 0.9(10) . . . . ?
C14 C15 C16 C1 -3.2(9) . . . . ?
C14 C15 C16 C17 174.7(6) . . . . ?
C2 C1 C16 C15 -175.4(6) . . . . ?
C6 C1 C16 C15 2.9(8) . . . . ?
C2 C1 C16 C17 6.7(9) . . . . ?
C6 C1 C16 C17 -174.9(5) . . . . ?
C15 C16 C17 C18 11.8(10) . . . . ?
C1 C16 C17 C18 -170.3(6) . . . . ?
C16 C17 C18 C19 -179.0(6) . . . . ?
C17 C18 C19 O 4.6(12) . . . . ?
C17 C18 C19 C20 -179.9(6) . . . . ?
O C19 C20 C21 169.7(7) . . . . ?
C18 C19 C20 C21 -5.7(10) . . . . ?
O C19 C20 C25 -9.6(10) . . . . ?
C18 C19 C20 C25 174.9(6) . . . . ?
C25 C20 C21 C22 4.1(11) . . . . ?
C19 C20 C21 C22 -175.3(7) . . . . ?
C20 C21 C22 C23 -4.5(11) . . . . ?
C21 C22 C23 C24 3.6(11) . . . . ?
C21 C22 C23 Cl 179.7(6) . . . . ?
C22 C23 C24 C25 -2.2(11) . . . . ?
Cl C23 C24 C25 -178.3(5) . . . . ?
C23 C24 C25 C20 1.7(11) . . . . ?
C21 C20 C25 C24 -2.6(10) . . . . ?
C19 C20 C25 C24 176.8(6) . . . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acette/acetic acid'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1473288'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ' 1-phenyl-3-(1-pyrenyl) prop-2-en-1-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H32 O2'
_chemical_formula_weight         664.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

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

_cell_length_a                   28.811(6)
_cell_length_b                   5.4880(11)
_cell_length_c                   21.784(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.25(3)
_cell_angle_gamma                90
_cell_volume                     3389.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6346
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.436
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6172
_reflns_number_gt                2566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0320P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6172
_refine_ls_number_parameters     469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1715
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.002
_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 0.45294(11) 0.5174(6) 0.06783(14) 0.0459(8) Uani 1 1 d . . . . .
O1 O 0.59852(8) 0.0372(5) 0.17417(13) 0.0891(9) Uani 1 1 d . . . . .
O2 O -0.08728(9) 0.9944(5) 0.13777(14) 0.0922(9) Uani 1 1 d . . . . .
C2 C 0.45589(11) 0.3311(6) 0.02341(16) 0.0563(10) Uani 1 1 d . . . . .
H2A H 0.4815 0.2252 0.0304 0.068 Uiso 1 1 calc R U . . .
C3 C 0.42280(12) 0.3015(7) -0.02876(16) 0.0605(10) Uani 1 1 d . . . . .
H3A H 0.4263 0.1783 -0.0569 0.073 Uiso 1 1 calc R U . . .
C4 C 0.38248(12) 0.4584(7) -0.04087(15) 0.0534(9) Uani 1 1 d . . . . .
C5 C 0.37814(11) 0.6471(7) 0.00150(15) 0.0495(9) Uani 1 1 d . . . . .
C6 C 0.41331(11) 0.6779(6) 0.05595(14) 0.0466(9) Uani 1 1 d . . . . .
C7 C 0.34712(13) 0.4287(8) -0.09398(16) 0.0733(12) Uani 1 1 d . . . . .
H7A H 0.3495 0.3050 -0.1224 0.088 Uiso 1 1 calc R U . . .
C8 C 0.30875(14) 0.5857(9) -0.10349(19) 0.0833(14) Uani 1 1 d . . . . .
H8A H 0.2853 0.5649 -0.1384 0.100 Uiso 1 1 calc R U . . .
C9 C 0.30456(13) 0.7712(8) -0.06245(19) 0.0776(13) Uani 1 1 d . . . . .
H9A H 0.2786 0.8746 -0.0705 0.093 Uiso 1 1 calc R U . . .
C10 C 0.33844(11) 0.8070(7) -0.00912(17) 0.0578(10) Uani 1 1 d . . . . .
C11 C 0.33542(12) 1.0008(7) 0.03334(18) 0.0654(11) Uani 1 1 d . . . . .
H11A H 0.3100 1.1076 0.0258 0.078 Uiso 1 1 calc R U . . .
C12 C 0.36894(12) 1.0317(7) 0.08436(17) 0.0625(10) Uani 1 1 d . . . . .
H12A H 0.3661 1.1582 0.1119 0.075 Uiso 1 1 calc R U . . .
C13 C 0.40893(11) 0.8721(7) 0.09682(15) 0.0512(9) Uani 1 1 d . . . . .
C14 C 0.44397(11) 0.9062(7) 0.14957(16) 0.0597(10) Uani 1 1 d . . . . .
H14A H 0.4417 1.0343 0.1768 0.072 Uiso 1 1 calc R U . . .
C15 C 0.48168(11) 0.7498(6) 0.16082(15) 0.0568(10) Uani 1 1 d . . . . .
H15A H 0.5047 0.7758 0.1959 0.068 Uiso 1 1 calc R U . . .
C16 C 0.48691(11) 0.5552(6) 0.12224(15) 0.0487(9) Uani 1 1 d . . . . .
C17 C 0.52678(11) 0.3871(7) 0.13906(15) 0.0569(10) Uani 1 1 d . . . . .
H17A H 0.5258 0.2441 0.1159 0.068 Uiso 1 1 calc R U . . .
C18 C 0.56391(12) 0.4180(7) 0.18369(16) 0.0677(11) Uani 1 1 d . . . . .
H18A H 0.5666 0.5636 0.2059 0.081 Uiso 1 1 calc R U . . .
C19 C 0.60078(12) 0.2357(7) 0.19981(17) 0.0565(10) Uani 1 1 d . . . . .
C20 C 0.64223(11) 0.2925(6) 0.25007(15) 0.0474(9) Uani 1 1 d . . . . .
C21 C 0.64458(12) 0.4957(7) 0.28748(16) 0.0621(10) Uani 1 1 d . . . . .
H21A H 0.6203 0.6093 0.2806 0.074 Uiso 1 1 calc R U . . .
C22 C 0.68269(12) 0.5342(7) 0.33547(17) 0.0669(11) Uani 1 1 d . . . . .
H22A H 0.6834 0.6694 0.3614 0.080 Uiso 1 1 calc R U . . .
C23 C 0.71919(12) 0.3710(7) 0.34414(16) 0.0614(10) Uani 1 1 d . . . . .
H23A H 0.7451 0.3980 0.3755 0.074 Uiso 1 1 calc R U . . .
C24 C 0.71791(12) 0.1691(7) 0.30729(17) 0.0650(11) Uani 1 1 d . . . . .
H24A H 0.7428 0.0587 0.3136 0.078 Uiso 1 1 calc R U . . .
C25 C 0.67933(11) 0.1295(7) 0.26038(16) 0.0620(10) Uani 1 1 d . . . . .
H25A H 0.6784 -0.0088 0.2355 0.074 Uiso 1 1 calc R U . . .
C26 C 0.05040(10) 0.4924(6) 0.08709(14) 0.0459(8) Uani 1 1 d . . . . .
C27 C 0.04495(11) 0.6769(7) 0.04004(15) 0.0566(10) Uani 1 1 d . . . . .
H27A H 0.0192 0.7815 0.0363 0.068 Uiso 1 1 calc R U . . .
C28 C 0.07589(12) 0.7043(7) 0.00095(16) 0.0616(10) Uani 1 1 d . . . . .
H28A H 0.0711 0.8276 -0.0288 0.074 Uiso 1 1 calc R U . . .
C29 C 0.11572(12) 0.5486(7) 0.00418(16) 0.0575(10) Uani 1 1 d . . . . .
C30 C 0.12214(11) 0.3597(7) 0.04961(16) 0.0522(9) Uani 1 1 d . . . . .
C31 C 0.08903(11) 0.3297(7) 0.09039(15) 0.0474(9) Uani 1 1 d . . . . .
C32 C 0.14864(14) 0.5772(8) -0.03523(17) 0.0795(13) Uani 1 1 d . . . . .
H32A H 0.1450 0.7029 -0.0643 0.095 Uiso 1 1 calc R U . . .
C33 C 0.18657(15) 0.4197(10) -0.0313(2) 0.0915(16) Uani 1 1 d . . . . .
H33A H 0.2083 0.4399 -0.0578 0.110 Uiso 1 1 calc R U . . .
C34 C 0.19230(13) 0.2331(9) 0.0117(2) 0.0853(15) Uani 1 1 d . . . . .
H34A H 0.2179 0.1283 0.0134 0.102 Uiso 1 1 calc R U . . .
C35 C 0.16083(12) 0.1966(8) 0.05285(19) 0.0658(11) Uani 1 1 d . . . . .
C36 C 0.16580(12) 0.0055(8) 0.0985(2) 0.0750(13) Uani 1 1 d . . . . .
H36A H 0.1910 -0.1021 0.1012 0.090 Uiso 1 1 calc R U . . .
C37 C 0.13519(12) -0.0208(7) 0.13684(17) 0.0699(12) Uani 1 1 d . . . . .
H37A H 0.1396 -0.1455 0.1662 0.084 Uiso 1 1 calc R U . . .
C38 C 0.09561(11) 0.1376(7) 0.13404(16) 0.0528(9) Uani 1 1 d . . . . .
C39 C 0.06290(12) 0.1063(7) 0.17366(16) 0.0643(10) Uani 1 1 d . . . . .
H39A H 0.0666 -0.0207 0.2024 0.077 Uiso 1 1 calc R U . . .
C40 C 0.02526(12) 0.2623(7) 0.17035(15) 0.0591(10) Uani 1 1 d . . . . .
H40A H 0.0034 0.2362 0.1964 0.071 Uiso 1 1 calc R U . . .
C41 C 0.01882(11) 0.4588(6) 0.12904(15) 0.0492(9) Uani 1 1 d . U . . .
C42 C -0.02010(11) 0.6292(7) 0.13107(15) 0.0567(9) Uani 1 1 d . U . . .
H42A H -0.0185 0.7768 0.1106 0.068 Uiso 1 1 calc R U . . .
C43 C -0.05713(11) 0.5990(7) 0.15844(16) 0.0604(10) Uani 1 1 d . . . . .
H43A H -0.0608 0.4521 0.1783 0.072 Uiso 1 1 calc R U . . .
C44 C -0.09262(12) 0.7919(7) 0.15829(16) 0.0573(10) Uani 1 1 d . . . . .
C45 C -0.13574(11) 0.7387(6) 0.18543(15) 0.0474(9) Uani 1 1 d . . . . .
C46 C -0.14106(12) 0.5358(7) 0.22050(16) 0.0617(10) Uani 1 1 d . . . . .
H46A H -0.1169 0.4217 0.2281 0.074 Uiso 1 1 calc R U . . .
C47 C -0.18169(12) 0.4981(7) 0.24477(17) 0.0678(11) Uani 1 1 d . . . . .
H47A H -0.1845 0.3614 0.2691 0.081 Uiso 1 1 calc R U . . .
C48 C -0.21770(12) 0.6626(7) 0.23280(16) 0.0603(10) Uani 1 1 d . . . . .
H48A H -0.2453 0.6366 0.2485 0.072 Uiso 1 1 calc R U . . .
C49 C -0.21342(12) 0.8669(7) 0.19758(16) 0.0661(11) Uani 1 1 d . . . . .
H49A H -0.2380 0.9786 0.1895 0.079 Uiso 1 1 calc R U . . .
C50 C -0.17241(12) 0.9056(7) 0.17430(15) 0.0611(10) Uani 1 1 d . . . . .
H50A H -0.1694 1.0447 0.1510 0.073 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 C16 1.412(4) . ?
C1 C2 1.421(4) . ?
C1 C6 1.428(4) . ?
O1 C19 1.221(4) . ?
O2 C44 1.217(4) . ?
C2 C3 1.357(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.432(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.407(4) . ?
C4 C7 1.408(4) . ?
C5 C6 1.426(4) . ?
C5 C10 1.428(4) . ?
C6 C13 1.409(4) . ?
C7 C8 1.388(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.374(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.392(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.422(5) . ?
C11 C12 1.347(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.434(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.401(4) . ?
C14 C15 1.372(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.468(4) . ?
C17 C18 1.322(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.456(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.502(4) . ?
C20 C21 1.375(4) . ?
C20 C25 1.381(4) . ?
C21 C22 1.391(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.369(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.365(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.387(4) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 C41 1.412(4) . ?
C26 C31 1.419(4) . ?
C26 C27 1.430(4) . ?
C27 C28 1.346(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.423(4) . ?
C28 H28A 0.9300 . ?
C29 C32 1.397(4) . ?
C29 C30 1.422(5) . ?
C30 C35 1.421(4) . ?
C30 C31 1.424(4) . ?
C31 C38 1.409(4) . ?
C32 C33 1.384(5) . ?
C32 H32A 0.9300 . ?
C33 C34 1.378(5) . ?
C33 H33A 0.9300 . ?
C34 C35 1.398(5) . ?
C34 H34A 0.9300 . ?
C35 C36 1.434(5) . ?
C36 C37 1.326(5) . ?
C36 H36A 0.9300 . ?
C37 C38 1.427(4) . ?
C37 H37A 0.9300 . ?
C38 C39 1.397(4) . ?
C39 C40 1.374(4) . ?
C39 H39A 0.9300 . ?
C40 C41 1.396(4) . ?
C40 H40A 0.9300 . ?
C41 C42 1.467(4) . ?
C42 C43 1.322(4) . ?
C42 H42A 0.9300 . ?
C43 C44 1.472(4) . ?
C43 H43A 0.9300 . ?
C44 C45 1.497(4) . ?
C45 C46 1.374(4) . ?
C45 C50 1.386(4) . ?
C46 C47 1.383(4) . ?
C46 H46A 0.9300 . ?
C47 C48 1.365(4) . ?
C47 H47A 0.9300 . ?
C48 C49 1.377(4) . ?
C48 H48A 0.9300 . ?
C49 C50 1.382(4) . ?
C49 H49A 0.9300 . ?
C50 H50A 0.9300 . ?

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
C16 C1 C2 124.1(3) . . ?
C16 C1 C6 118.3(3) . . ?
C2 C1 C6 117.6(3) . . ?
C3 C2 C1 122.6(3) . . ?
C3 C2 H2A 118.7 . . ?
C1 C2 H2A 118.7 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C7 119.2(3) . . ?
C5 C4 C3 119.0(3) . . ?
C7 C4 C3 121.7(4) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 C10 120.5(3) . . ?
C6 C5 C10 119.5(3) . . ?
C13 C6 C5 119.0(3) . . ?
C13 C6 C1 120.7(3) . . ?
C5 C6 C1 120.3(3) . . ?
C8 C7 C4 119.4(4) . . ?
C8 C7 H7A 120.3 . . ?
C4 C7 H7A 120.3 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C9 C10 C11 122.2(4) . . ?
C9 C10 C5 118.1(4) . . ?
C11 C10 C5 119.6(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C6 119.2(3) . . ?
C14 C13 C12 120.7(4) . . ?
C6 C13 C12 120.1(3) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 122.9(3) . . ?
C14 C15 H15A 118.6 . . ?
C16 C15 H15A 118.6 . . ?
C15 C16 C1 119.3(3) . . ?
C15 C16 C17 119.9(3) . . ?
C1 C16 C17 120.8(3) . . ?
C18 C17 C16 126.7(3) . . ?
C18 C17 H17A 116.7 . . ?
C16 C17 H17A 116.7 . . ?
C17 C18 C19 123.3(3) . . ?
C17 C18 H18A 118.3 . . ?
C19 C18 H18A 118.3 . . ?
O1 C19 C18 121.7(3) . . ?
O1 C19 C20 119.3(3) . . ?
C18 C19 C20 119.0(3) . . ?
C21 C20 C25 118.3(3) . . ?
C21 C20 C19 123.3(3) . . ?
C25 C20 C19 118.4(3) . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H21A 119.4 . . ?
C22 C21 H21A 119.4 . . ?
C23 C22 C21 119.2(4) . . ?
C23 C22 H22A 120.4 . . ?
C21 C22 H22A 120.4 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C25 119.7(3) . . ?
C23 C24 H24A 120.2 . . ?
C25 C24 H24A 120.2 . . ?
C20 C25 C24 120.9(3) . . ?
C20 C25 H25A 119.5 . . ?
C24 C25 H25A 119.5 . . ?
C41 C26 C31 118.4(3) . . ?
C41 C26 C27 123.7(3) . . ?
C31 C26 C27 117.9(3) . . ?
C28 C27 C26 122.1(3) . . ?
C28 C27 H27A 118.9 . . ?
C26 C27 H27A 118.9 . . ?
C27 C28 C29 121.4(4) . . ?
C27 C28 H28A 119.3 . . ?
C29 C28 H28A 119.3 . . ?
C32 C29 C30 119.4(4) . . ?
C32 C29 C28 122.2(4) . . ?
C30 C29 C28 118.4(3) . . ?
C35 C30 C29 119.8(4) . . ?
C35 C30 C31 120.2(4) . . ?
C29 C30 C31 120.0(3) . . ?
C38 C31 C26 121.0(3) . . ?
C38 C31 C30 118.9(3) . . ?
C26 C31 C30 120.1(3) . . ?
C33 C32 C29 120.5(4) . . ?
C33 C32 H32A 119.8 . . ?
C29 C32 H32A 119.8 . . ?
C34 C33 C32 120.3(4) . . ?
C34 C33 H33A 119.9 . . ?
C32 C33 H33A 119.9 . . ?
C33 C34 C35 122.0(4) . . ?
C33 C34 H34A 119.0 . . ?
C35 C34 H34A 119.0 . . ?
C34 C35 C30 118.1(4) . . ?
C34 C35 C36 123.5(4) . . ?
C30 C35 C36 118.4(4) . . ?
C37 C36 C35 121.4(4) . . ?
C37 C36 H36A 119.3 . . ?
C35 C36 H36A 119.3 . . ?
C36 C37 C38 121.5(4) . . ?
C36 C37 H37A 119.2 . . ?
C38 C37 H37A 119.2 . . ?
C39 C38 C31 119.0(3) . . ?
C39 C38 C37 121.4(4) . . ?
C31 C38 C37 119.7(3) . . ?
C40 C39 C38 120.3(4) . . ?
C40 C39 H39A 119.9 . . ?
C38 C39 H39A 119.9 . . ?
C39 C40 C41 121.9(3) . . ?
C39 C40 H40A 119.0 . . ?
C41 C40 H40A 119.0 . . ?
C40 C41 C26 119.4(3) . . ?
C40 C41 C42 119.2(3) . . ?
C26 C41 C42 121.4(3) . . ?
C43 C42 C41 128.1(4) . . ?
C43 C42 H42A 116.0 . . ?
C41 C42 H42A 116.0 . . ?
C42 C43 C44 121.7(4) . . ?
C42 C43 H43A 119.2 . . ?
C44 C43 H43A 119.2 . . ?
O2 C44 C43 121.6(3) . . ?
O2 C44 C45 119.4(3) . . ?
C43 C44 C45 119.0(3) . . ?
C46 C45 C50 118.4(3) . . ?
C46 C45 C44 124.1(3) . . ?
C50 C45 C44 117.5(3) . . ?
C45 C46 C47 121.3(3) . . ?
C45 C46 H46A 119.3 . . ?
C47 C46 H46A 119.3 . . ?
C48 C47 C46 119.6(4) . . ?
C48 C47 H47A 120.2 . . ?
C46 C47 H47A 120.2 . . ?
C47 C48 C49 120.3(3) . . ?
C47 C48 H48A 119.8 . . ?
C49 C48 H48A 119.8 . . ?
C48 C49 C50 119.8(3) . . ?
C48 C49 H49A 120.1 . . ?
C50 C49 H49A 120.1 . . ?
C49 C50 C45 120.6(4) . . ?
C49 C50 H50A 119.7 . . ?
C45 C50 H50A 119.7 . . ?

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
C16 C1 C2 C3 -179.3(3) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C2 C3 C4 C7 -178.7(3) . . . . ?
C7 C4 C5 C6 179.2(3) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C7 C4 C5 C10 -0.1(5) . . . . ?
C3 C4 C5 C10 180.0(3) . . . . ?
C4 C5 C6 C13 178.2(3) . . . . ?
C10 C5 C6 C13 -2.5(4) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C10 C5 C6 C1 179.1(3) . . . . ?
C16 C1 C6 C13 1.5(4) . . . . ?
C2 C1 C6 C13 -177.8(3) . . . . ?
C16 C1 C6 C5 179.9(3) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C5 C4 C7 C8 0.0(5) . . . . ?
C3 C4 C7 C8 180.0(3) . . . . ?
C4 C7 C8 C9 0.5(6) . . . . ?
C7 C8 C9 C10 -0.9(6) . . . . ?
C8 C9 C10 C11 178.6(4) . . . . ?
C8 C9 C10 C5 0.7(5) . . . . ?
C4 C5 C10 C9 -0.3(5) . . . . ?
C6 C5 C10 C9 -179.6(3) . . . . ?
C4 C5 C10 C11 -178.2(3) . . . . ?
C6 C5 C10 C11 2.5(5) . . . . ?
C9 C10 C11 C12 -179.6(3) . . . . ?
C5 C10 C11 C12 -1.7(5) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C5 C6 C13 C14 -178.5(3) . . . . ?
C1 C6 C13 C14 -0.1(5) . . . . ?
C5 C6 C13 C12 1.6(4) . . . . ?
C1 C6 C13 C12 -180.0(3) . . . . ?
C11 C12 C13 C14 179.3(3) . . . . ?
C11 C12 C13 C6 -0.8(5) . . . . ?
C6 C13 C14 C15 -0.4(5) . . . . ?
C12 C13 C14 C15 179.4(3) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C1 1.8(5) . . . . ?
C14 C15 C16 C17 -176.5(3) . . . . ?
C2 C1 C16 C15 176.9(3) . . . . ?
C6 C1 C16 C15 -2.3(4) . . . . ?
C2 C1 C16 C17 -4.8(5) . . . . ?
C6 C1 C16 C17 176.0(3) . . . . ?
C15 C16 C17 C18 -11.0(5) . . . . ?
C1 C16 C17 C18 170.6(3) . . . . ?
C16 C17 C18 C19 176.4(3) . . . . ?
C17 C18 C19 O1 -2.8(6) . . . . ?
C17 C18 C19 C20 178.2(3) . . . . ?
O1 C19 C20 C21 -170.4(4) . . . . ?
C18 C19 C20 C21 8.6(5) . . . . ?
O1 C19 C20 C25 7.8(5) . . . . ?
C18 C19 C20 C25 -173.2(3) . . . . ?
C25 C20 C21 C22 -1.5(5) . . . . ?
C19 C20 C21 C22 176.7(3) . . . . ?
C20 C21 C22 C23 2.2(5) . . . . ?
C21 C22 C23 C24 -1.6(5) . . . . ?
C22 C23 C24 C25 0.3(5) . . . . ?
C21 C20 C25 C24 0.1(5) . . . . ?
C19 C20 C25 C24 -178.2(3) . . . . ?
C23 C24 C25 C20 0.5(5) . . . . ?
C41 C26 C27 C28 179.7(3) . . . . ?
C31 C26 C27 C28 -2.2(5) . . . . ?
C26 C27 C28 C29 0.5(5) . . . . ?
C27 C28 C29 C32 -178.8(3) . . . . ?
C27 C28 C29 C30 0.6(5) . . . . ?
C32 C29 C30 C35 -2.4(5) . . . . ?
C28 C29 C30 C35 178.2(3) . . . . ?
C32 C29 C30 C31 179.5(3) . . . . ?
C28 C29 C30 C31 0.1(4) . . . . ?
C41 C26 C31 C38 0.6(4) . . . . ?
C27 C26 C31 C38 -177.6(3) . . . . ?
C41 C26 C31 C30 -179.0(3) . . . . ?
C27 C26 C31 C30 2.9(4) . . . . ?
C35 C30 C31 C38 0.5(4) . . . . ?
C29 C30 C31 C38 178.6(3) . . . . ?
C35 C30 C31 C26 -179.9(3) . . . . ?
C29 C30 C31 C26 -1.9(4) . . . . ?
C30 C29 C32 C33 1.6(5) . . . . ?
C28 C29 C32 C33 -179.0(3) . . . . ?
C29 C32 C33 C34 -0.1(6) . . . . ?
C32 C33 C34 C35 -0.5(6) . . . . ?
C33 C34 C35 C30 -0.3(6) . . . . ?
C33 C34 C35 C36 -179.6(4) . . . . ?
C29 C30 C35 C34 1.8(5) . . . . ?
C31 C30 C35 C34 179.8(3) . . . . ?
C29 C30 C35 C36 -178.9(3) . . . . ?
C31 C30 C35 C36 -0.9(5) . . . . ?
C34 C35 C36 C37 179.5(4) . . . . ?
C30 C35 C36 C37 0.2(5) . . . . ?
C35 C36 C37 C38 0.7(6) . . . . ?
C26 C31 C38 C39 1.1(5) . . . . ?
C30 C31 C38 C39 -179.3(3) . . . . ?
C26 C31 C38 C37 -179.1(3) . . . . ?
C30 C31 C38 C37 0.4(4) . . . . ?
C36 C37 C38 C39 178.7(3) . . . . ?
C36 C37 C38 C31 -1.1(5) . . . . ?
C31 C38 C39 C40 -0.7(5) . . . . ?
C37 C38 C39 C40 179.5(3) . . . . ?
C38 C39 C40 C41 -1.5(5) . . . . ?
C39 C40 C41 C26 3.3(5) . . . . ?
C39 C40 C41 C42 -175.5(3) . . . . ?
C31 C26 C41 C40 -2.7(4) . . . . ?
C27 C26 C41 C40 175.3(3) . . . . ?
C31 C26 C41 C42 176.0(3) . . . . ?
C27 C26 C41 C42 -6.0(5) . . . . ?
C40 C41 C42 C43 -15.3(5) . . . . ?
C26 C41 C42 C43 166.0(3) . . . . ?
C41 C42 C43 C44 177.7(3) . . . . ?
C42 C43 C44 O2 -6.5(6) . . . . ?
C42 C43 C44 C45 174.9(3) . . . . ?
O2 C44 C45 C46 -166.7(3) . . . . ?
C43 C44 C45 C46 11.9(5) . . . . ?
O2 C44 C45 C50 13.3(5) . . . . ?
C43 C44 C45 C50 -168.1(3) . . . . ?
C50 C45 C46 C47 -0.5(5) . . . . ?
C44 C45 C46 C47 179.4(3) . . . . ?
C45 C46 C47 C48 1.3(5) . . . . ?
C46 C47 C48 C49 -1.0(5) . . . . ?
C47 C48 C49 C50 -0.1(5) . . . . ?
C48 C49 C50 C45 0.8(5) . . . . ?
C46 C45 C50 C49 -0.5(5) . . . . ?
C44 C45 C50 C49 179.5(3) . . . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate/ethanol'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1473292'
_audit_update_record             
;
2017-01-16 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'3-(1-pyrenyl)-1-(4-nitrophenyl) prop-2-en-1-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H15 N O3'
_chemical_formula_weight         377.38

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.3870(15)
_cell_length_b                   7.8470(16)
_cell_length_c                   32.089(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.00(3)
_cell_angle_gamma                90
_cell_volume                     1855.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       needlelike
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3526
_diffrn_reflns_av_unetI/netI     0.1144
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         25.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3268
_reflns_number_gt                1310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0430P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3268
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2004
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
N N 0.4235(6) 0.0447(7) -0.19953(15) 0.0806(14) Uani 1 1 d . . . . .
C1 C 0.1692(5) 0.6976(5) 0.07048(11) 0.0436(10) Uani 1 1 d . . . . .
O1 O 0.2388(5) 0.6766(5) -0.08530(9) 0.1005(13) Uani 1 1 d . . . . .
C2 C 0.1085(5) 0.8613(5) 0.05582(12) 0.0524(11) Uani 1 1 d . . . . .
H2A H 0.1048 0.8832 0.0273 0.063 Uiso 1 1 calc R U . . .
O2 O 0.4011(5) 0.0900(5) -0.23550(11) 0.1123(15) Uani 1 1 d . . . . .
C3 C 0.0562(5) 0.9862(5) 0.08161(11) 0.0551(12) Uani 1 1 d . . . . .
H3A H 0.0177 1.0907 0.0706 0.066 Uiso 1 1 calc R U . . .
O3 O 0.4794(6) -0.0957(5) -0.18875(12) 0.1132(16) Uani 1 1 d . . . . .
C4 C 0.0599(5) 0.9579(5) 0.12605(11) 0.0447(11) Uani 1 1 d . . . . .
C5 C 0.1180(5) 0.7995(5) 0.14167(10) 0.0428(10) Uani 1 1 d . . . . .
C6 C 0.1721(5) 0.6687(5) 0.11407(11) 0.0424(10) Uani 1 1 d . . . . .
C7 C 0.0068(6) 1.0831(5) 0.15329(13) 0.0615(13) Uani 1 1 d . . . . .
H7A H -0.0318 1.1887 0.1430 0.074 Uiso 1 1 calc R U . . .
C8 C 0.0111(6) 1.0508(6) 0.19572(13) 0.0666(14) Uani 1 1 d . . . . .
H8A H -0.0239 1.1357 0.2137 0.080 Uiso 1 1 calc R U . . .
C9 C 0.0668(6) 0.8945(6) 0.21181(13) 0.0622(13) Uani 1 1 d . . . . .
H9A H 0.0678 0.8744 0.2404 0.075 Uiso 1 1 calc R U . . .
C10 C 0.1206(5) 0.7686(6) 0.18550(12) 0.0513(11) Uani 1 1 d . . . . .
C11 C 0.1798(6) 0.6060(6) 0.20041(13) 0.0594(12) Uani 1 1 d . . . . .
H11A H 0.1838 0.5847 0.2290 0.071 Uiso 1 1 calc R U . . .
C12 C 0.2304(5) 0.4814(6) 0.17473(12) 0.0572(12) Uani 1 1 d . . . . .
H12A H 0.2664 0.3764 0.1859 0.069 Uiso 1 1 calc R U . . .
C13 C 0.2297(5) 0.5073(5) 0.13087(12) 0.0473(10) Uani 1 1 d . . . . .
C14 C 0.2827(6) 0.3846(6) 0.10317(13) 0.0636(13) Uani 1 1 d . . . . .
H14A H 0.3218 0.2791 0.1135 0.076 Uiso 1 1 calc R U . . .
C15 C 0.2792(6) 0.4142(6) 0.06102(14) 0.0632(13) Uani 1 1 d . . . . .
H15A H 0.3148 0.3276 0.0436 0.076 Uiso 1 1 calc R U . . .
C16 C 0.2247(5) 0.5683(5) 0.04364(12) 0.0471(11) Uani 1 1 d . . . . .
C17 C 0.2302(5) 0.5945(6) -0.00099(12) 0.0574(12) Uani 1 1 d . . . . .
H17A H 0.2056 0.7049 -0.0103 0.069 Uiso 1 1 calc R U . . .
C18 C 0.2657(5) 0.4825(6) -0.03044(12) 0.0620(13) Uani 1 1 d . . . . .
H18A H 0.2888 0.3698 -0.0228 0.074 Uiso 1 1 calc R U . . .
C19 C 0.2694(6) 0.5311(6) -0.07456(13) 0.0572(12) Uani 1 1 d . . . . .
C20 C 0.3097(5) 0.3994(6) -0.10608(12) 0.0546(12) Uani 1 1 d . . . . .
C21 C 0.3635(6) 0.2373(6) -0.09560(12) 0.0617(13) Uani 1 1 d . . . . .
H21A H 0.3749 0.2056 -0.0676 0.074 Uiso 1 1 calc R U . . .
C22 C 0.4015(6) 0.1186(6) -0.12622(15) 0.0678(14) Uani 1 1 d . . . . .
H22A H 0.4362 0.0079 -0.1190 0.081 Uiso 1 1 calc R U . . .
C23 C 0.3864(6) 0.1692(7) -0.16661(14) 0.0572(12) Uani 1 1 d . . . . .
C24 C 0.3354(5) 0.3290(6) -0.17842(13) 0.0606(13) Uani 1 1 d . . . . .
H24A H 0.3272 0.3598 -0.2065 0.073 Uiso 1 1 calc R U . . .
C25 C 0.2956(6) 0.4456(6) -0.14794(12) 0.0634(13) Uani 1 1 d . . . . .
H25A H 0.2594 0.5554 -0.1556 0.076 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
N O2 1.208(5) . ?
N O3 1.218(5) . ?
N C23 1.479(5) . ?
C1 C16 1.410(5) . ?
C1 C6 1.416(5) . ?
C1 C2 1.429(5) . ?
O1 C19 1.209(5) . ?
C2 C3 1.357(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.442(5) . ?
C3 H3A 0.9300 . ?
C4 C7 1.389(5) . ?
C4 C5 1.397(5) . ?
C5 C10 1.426(5) . ?
C5 C6 1.431(5) . ?
C6 C13 1.430(5) . ?
C7 C8 1.383(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.382(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.376(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.421(5) . ?
C11 C12 1.348(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.422(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(5) . ?
C14 C15 1.371(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.381(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.450(5) . ?
C17 C18 1.330(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.468(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.490(5) . ?
C20 C21 1.368(5) . ?
C20 C25 1.388(5) . ?
C21 C22 1.397(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.353(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.356(6) . ?
C24 C25 1.386(5) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?

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
O2 N O3 124.0(5) . . ?
O2 N C23 117.9(5) . . ?
O3 N C23 118.1(5) . . ?
C16 C1 C6 120.2(4) . . ?
C16 C1 C2 122.9(4) . . ?
C6 C1 C2 116.9(4) . . ?
C3 C2 C1 123.0(4) . . ?
C3 C2 H2A 118.5 . . ?
C1 C2 H2A 118.5 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C7 C4 C5 119.8(4) . . ?
C7 C4 C3 121.8(4) . . ?
C5 C4 C3 118.4(4) . . ?
C4 C5 C10 119.2(4) . . ?
C4 C5 C6 120.6(3) . . ?
C10 C5 C6 120.3(4) . . ?
C1 C6 C13 119.9(4) . . ?
C1 C6 C5 120.8(4) . . ?
C13 C6 C5 119.4(4) . . ?
C8 C7 C4 120.1(4) . . ?
C8 C7 H7A 119.9 . . ?
C4 C7 H7A 119.9 . . ?
C9 C8 C7 121.1(4) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 122.2(4) . . ?
C9 C10 C5 119.9(4) . . ?
C11 C10 C5 117.9(4) . . ?
C12 C11 C10 122.5(4) . . ?
C12 C11 H11A 118.7 . . ?
C10 C11 H11A 118.7 . . ?
C11 C12 C13 121.3(4) . . ?
C11 C12 H12A 119.3 . . ?
C13 C12 H12A 119.3 . . ?
C14 C13 C12 123.7(4) . . ?
C14 C13 C6 117.6(4) . . ?
C12 C13 C6 118.7(4) . . ?
C15 C14 C13 121.9(4) . . ?
C15 C14 H14A 119.0 . . ?
C13 C14 H14A 119.0 . . ?
C14 C15 C16 122.1(4) . . ?
C14 C15 H15A 118.9 . . ?
C16 C15 H15A 118.9 . . ?
C15 C16 C1 118.2(4) . . ?
C15 C16 C17 119.7(4) . . ?
C1 C16 C17 122.1(4) . . ?
C18 C17 C16 129.0(4) . . ?
C18 C17 H17A 115.5 . . ?
C16 C17 H17A 115.5 . . ?
C17 C18 C19 122.1(4) . . ?
C17 C18 H18A 118.9 . . ?
C19 C18 H18A 118.9 . . ?
O1 C19 C18 120.3(4) . . ?
O1 C19 C20 120.2(4) . . ?
C18 C19 C20 119.5(4) . . ?
C21 C20 C25 118.8(4) . . ?
C21 C20 C19 123.1(4) . . ?
C25 C20 C19 118.1(4) . . ?
C20 C21 C22 121.1(4) . . ?
C20 C21 H21A 119.4 . . ?
C22 C21 H21A 119.4 . . ?
C23 C22 C21 118.1(5) . . ?
C23 C22 H22A 120.9 . . ?
C21 C22 H22A 120.9 . . ?
C22 C23 C24 122.8(5) . . ?
C22 C23 N 118.9(5) . . ?
C24 C23 N 118.2(5) . . ?
C23 C24 C25 118.8(4) . . ?
C23 C24 H24A 120.6 . . ?
C25 C24 H24A 120.6 . . ?
C24 C25 C20 120.3(4) . . ?
C24 C25 H25A 119.8 . . ?
C20 C25 H25A 119.8 . . ?

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
C16 C1 C2 C3 -179.5(4) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C2 C3 C4 C7 -179.9(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C7 C4 C5 C10 0.4(6) . . . . ?
C3 C4 C5 C10 -179.3(3) . . . . ?
C7 C4 C5 C6 179.6(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C16 C1 C6 C13 -0.7(5) . . . . ?
C2 C1 C6 C13 179.4(4) . . . . ?
C16 C1 C6 C5 179.3(4) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C10 C5 C6 C1 179.6(3) . . . . ?
C4 C5 C6 C13 -179.5(4) . . . . ?
C10 C5 C6 C13 -0.4(5) . . . . ?
C5 C4 C7 C8 -0.1(6) . . . . ?
C3 C4 C7 C8 179.6(4) . . . . ?
C4 C7 C8 C9 -0.4(7) . . . . ?
C7 C8 C9 C10 0.6(7) . . . . ?
C8 C9 C10 C11 179.7(4) . . . . ?
C8 C9 C10 C5 -0.3(6) . . . . ?
C4 C5 C10 C9 -0.2(6) . . . . ?
C6 C5 C10 C9 -179.4(4) . . . . ?
C4 C5 C10 C11 179.8(4) . . . . ?
C6 C5 C10 C11 0.6(5) . . . . ?
C9 C10 C11 C12 179.1(4) . . . . ?
C5 C10 C11 C12 -0.9(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C14 179.1(4) . . . . ?
C11 C12 C13 C6 -0.7(6) . . . . ?
C1 C6 C13 C14 0.6(5) . . . . ?
C5 C6 C13 C14 -179.4(4) . . . . ?
C1 C6 C13 C12 -179.6(3) . . . . ?
C5 C6 C13 C12 0.4(5) . . . . ?
C12 C13 C14 C15 179.6(4) . . . . ?
C6 C13 C14 C15 -0.6(6) . . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C14 C15 C16 C1 -0.8(6) . . . . ?
C14 C15 C16 C17 177.7(4) . . . . ?
C6 C1 C16 C15 0.8(6) . . . . ?
C2 C1 C16 C15 -179.4(4) . . . . ?
C6 C1 C16 C17 -177.7(3) . . . . ?
C2 C1 C16 C17 2.2(6) . . . . ?
C15 C16 C17 C18 7.3(7) . . . . ?
C1 C16 C17 C18 -174.3(4) . . . . ?
C16 C17 C18 C19 -178.7(4) . . . . ?
C17 C18 C19 O1 -0.4(7) . . . . ?
C17 C18 C19 C20 -179.9(4) . . . . ?
O1 C19 C20 C21 173.1(5) . . . . ?
C18 C19 C20 C21 -7.4(6) . . . . ?
O1 C19 C20 C25 -5.4(6) . . . . ?
C18 C19 C20 C25 174.1(4) . . . . ?
C25 C20 C21 C22 -0.9(6) . . . . ?
C19 C20 C21 C22 -179.3(4) . . . . ?
C20 C21 C22 C23 1.0(6) . . . . ?
C21 C22 C23 C24 -0.3(7) . . . . ?
C21 C22 C23 N -179.1(4) . . . . ?
O2 N C23 C22 176.6(5) . . . . ?
O3 N C23 C22 -5.3(7) . . . . ?
O2 N C23 C24 -2.2(6) . . . . ?
O3 N C23 C24 175.8(5) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
N C23 C24 C25 178.3(4) . . . . ?
C23 C24 C25 C20 0.6(6) . . . . ?
C21 C20 C25 C24 0.1(6) . . . . ?
C19 C20 C25 C24 178.6(4) . . . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile/dichloromethane'
_exptl_crystal_preparation       ', Luminescent'
