# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_Cou-Nap
_database_code_depnum_ccdc_archive 'CCDC 1509578'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2017-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
7,7'-(Naphthalene-1,8-diyl)bis(4-methylcoumarin)
_chemical_name_common            ?
_chemical_melting_point          '220-222 degree C'
_chemical_formula_moiety         'C30 H20 O4'
_chemical_formula_sum            'C30 H20 O4'
_chemical_formula_weight         444.46

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

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

_cell_length_a                   9.0080(4)
_cell_length_b                   15.3830(6)
_cell_length_c                   15.6270(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2165.43(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3069
_cell_measurement_theta_min      2.607
_cell_measurement_theta_max      28.299

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22106
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.607
_diffrn_reflns_theta_max         28.299
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5372
_reflns_number_gt                3069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5372
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2629(2) 0.11168(13) -0.09586(11) 0.0453(5) Uani 1 1 d . . . . .
O2 O 0.3851(3) 0.12408(16) 0.02485(14) 0.0661(7) Uani 1 1 d . . . . .
O3 O 0.2665(2) 0.34202(13) -0.07270(12) 0.0484(6) Uani 1 1 d . . . . .
O4 O 0.3731(3) 0.37076(18) 0.04998(14) 0.0722(8) Uani 1 1 d . . . . .
C1 C -0.0185(4) 0.1241(2) -0.36036(18) 0.0418(8) Uani 1 1 d . . . . .
C2 C -0.0932(4) 0.0578(2) -0.4004(2) 0.0528(9) Uani 1 1 d . . . . .
H2 H -0.0556 0.0016 -0.3961 0.063 Uiso 1 1 calc R U . . .
C3 C -0.2232(4) 0.0711(2) -0.4472(2) 0.0587(10) Uani 1 1 d . . . . .
H3 H -0.2706 0.0246 -0.4737 0.070 Uiso 1 1 calc R U . . .
C4 C -0.2793(4) 0.1522(2) -0.45347(19) 0.0527(9) Uani 1 1 d . . . . .
H4 H -0.3686 0.1610 -0.4820 0.063 Uiso 1 1 calc R U . . .
C5 C -0.2045(3) 0.2238(2) -0.41745(17) 0.0431(8) Uani 1 1 d . . . . .
C6 C -0.0710(3) 0.2119(2) -0.36956(17) 0.0387(7) Uani 1 1 d . . . . .
C7 C -0.2620(4) 0.3080(2) -0.43040(18) 0.0533(9) Uani 1 1 d . . . . .
H7 H -0.3486 0.3149 -0.4620 0.064 Uiso 1 1 calc R U . . .
C8 C -0.1940(4) 0.3786(2) -0.3979(2) 0.0601(10) Uani 1 1 d . . . . .
H8 H -0.2334 0.4337 -0.4068 0.072 Uiso 1 1 calc R U . . .
C9 C -0.0637(4) 0.3682(2) -0.3506(2) 0.0524(9) Uani 1 1 d . . . . .
H9 H -0.0181 0.4173 -0.3280 0.063 Uiso 1 1 calc R U . . .
C10 C -0.0006(3) 0.2887(2) -0.33625(18) 0.0400(7) Uani 1 1 d . . . . .
C11 C 0.1162(4) 0.09826(18) -0.31110(18) 0.0415(8) Uani 1 1 d . . . . .
C12 C 0.2361(4) 0.0599(2) -0.3533(2) 0.0505(9) Uani 1 1 d . . . . .
H12 H 0.2278 0.0465 -0.4112 0.061 Uiso 1 1 calc R U . . .
C13 C 0.3653(4) 0.0418(2) -0.3114(2) 0.0527(9) Uani 1 1 d . . . . .
H13 H 0.4436 0.0168 -0.3413 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3822(4) 0.05996(19) -0.22449(19) 0.0435(8) Uani 1 1 d . . . . .
C15 C 0.2578(4) 0.09266(17) -0.18220(17) 0.0391(8) Uani 1 1 d . . . . .
C16 C 0.1267(4) 0.11043(18) -0.22305(18) 0.0408(8) Uani 1 1 d . . . . .
H16 H 0.0453 0.1305 -0.1922 0.049 Uiso 1 1 calc R U . . .
C17 C 0.5204(4) 0.05236(19) -0.1772(2) 0.0458(8) Uani 1 1 d . . . . .
C18 C 0.5209(4) 0.0753(2) -0.0942(2) 0.0497(9) Uani 1 1 d . . . . .
H18 H 0.6099 0.0715 -0.0643 0.060 Uiso 1 1 calc R U . . .
C19 C 0.3929(4) 0.1049(2) -0.0496(2) 0.0471(8) Uani 1 1 d . . . . .
C20 C 0.6597(4) 0.0224(3) -0.2203(2) 0.0696(11) Uani 1 1 d . . . . .
H20A H 0.6468 -0.0362 -0.2401 0.104 Uiso 1 1 calc R U . . .
H20B H 0.7406 0.0246 -0.1804 0.104 Uiso 1 1 calc R U . . .
H20C H 0.6809 0.0596 -0.2681 0.104 Uiso 1 1 calc R U . . .
C21 C 0.1422(3) 0.29008(19) -0.28726(18) 0.0395(7) Uani 1 1 d . . . . .
C22 C 0.2768(4) 0.2712(2) -0.32679(18) 0.0463(8) Uani 1 1 d . . . . .
H22 H 0.2782 0.2562 -0.3844 0.056 Uiso 1 1 calc R U . . .
C23 C 0.4070(4) 0.2745(2) -0.28199(18) 0.0449(8) Uani 1 1 d . . . . .
H23 H 0.4956 0.2617 -0.3098 0.054 Uiso 1 1 calc R U . . .
C24 C 0.4097(3) 0.29696(18) -0.19478(18) 0.0388(7) Uani 1 1 d . . . . .
C25 C 0.2741(4) 0.31770(18) -0.15775(18) 0.0389(7) Uani 1 1 d . . . . .
C26 C 0.1420(4) 0.31522(18) -0.20187(18) 0.0411(8) Uani 1 1 d . . . . .
H26 H 0.0536 0.3302 -0.1749 0.049 Uiso 1 1 calc R U . . .
C27 C 0.5427(3) 0.29985(19) -0.1433(2) 0.0440(8) Uani 1 1 d . . . . .
C28 C 0.5290(4) 0.3217(2) -0.0606(2) 0.0511(9) Uani 1 1 d . . . . .
H28 H 0.6136 0.3211 -0.0264 0.061 Uiso 1 1 calc R U . . .
C29 C 0.3910(4) 0.3459(2) -0.0223(2) 0.0502(8) Uani 1 1 d . . . . .
C30 C 0.6911(4) 0.2793(3) -0.1820(2) 0.0626(10) Uani 1 1 d . . . . .
H30A H 0.6869 0.2235 -0.2096 0.094 Uiso 1 1 calc R U . . .
H30B H 0.7652 0.2781 -0.1379 0.094 Uiso 1 1 calc R U . . .
H30C H 0.7162 0.3230 -0.2234 0.094 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
O1 C19 1.379(3) . ?
O1 C15 1.381(3) . ?
O2 C19 1.203(4) . ?
O3 C29 1.372(4) . ?
O3 C25 1.382(3) . ?
O4 C29 1.204(3) . ?
C1 C2 1.373(4) . ?
C1 C6 1.439(4) . ?
C1 C11 1.490(4) . ?
C2 C3 1.397(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.350(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(4) . ?
C4 H4 0.9300 . ?
C5 C7 1.409(4) . ?
C5 C6 1.428(4) . ?
C6 C10 1.438(4) . ?
C7 C8 1.347(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.395(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9300 . ?
C10 C21 1.497(4) . ?
C11 C16 1.392(4) . ?
C11 C12 1.397(4) . ?
C12 C13 1.365(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(4) . ?
C14 C17 1.452(4) . ?
C15 C16 1.370(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.344(4) . ?
C17 C20 1.497(5) . ?
C18 C19 1.422(4) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.389(4) . ?
C21 C22 1.391(4) . ?
C22 C23 1.367(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.406(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(4) . ?
C24 C27 1.444(4) . ?
C25 C26 1.376(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.342(4) . ?
C27 C30 1.501(4) . ?
C28 C29 1.429(5) . ?
C28 H28 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 C15 121.6(3) . . ?
C29 O3 C25 121.5(3) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 C11 115.9(3) . . ?
C6 C1 C11 124.7(3) . . ?
C1 C2 C3 122.7(3) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C7 119.0(3) . . ?
C4 C5 C6 120.8(3) . . ?
C7 C5 C6 120.2(3) . . ?
C5 C6 C10 117.1(3) . . ?
C5 C6 C1 116.7(3) . . ?
C10 C6 C1 126.2(3) . . ?
C8 C7 C5 121.3(3) . . ?
C8 C7 H7 119.4 . . ?
C5 C7 H7 119.4 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 122.7(3) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C6 119.4(3) . . ?
C9 C10 C21 115.4(3) . . ?
C6 C10 C21 125.2(3) . . ?
C16 C11 C12 118.1(3) . . ?
C16 C11 C1 122.0(3) . . ?
C12 C11 C1 119.9(3) . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 116.5(3) . . ?
C13 C14 C17 125.0(3) . . ?
C15 C14 C17 118.5(3) . . ?
C16 C15 O1 116.2(3) . . ?
C16 C15 C14 122.9(3) . . ?
O1 C15 C14 120.8(3) . . ?
C15 C16 C11 119.5(3) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C18 C17 C14 118.2(3) . . ?
C18 C17 C20 120.8(3) . . ?
C14 C17 C20 120.9(3) . . ?
C17 C18 C19 123.6(3) . . ?
C17 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
O2 C19 O1 116.0(3) . . ?
O2 C19 C18 126.8(3) . . ?
O1 C19 C18 117.1(3) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 119.1(3) . . ?
C26 C21 C10 119.6(3) . . ?
C22 C21 C10 121.2(3) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 121.4(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 116.4(3) . . ?
C25 C24 C27 119.4(3) . . ?
C23 C24 C27 124.2(3) . . ?
C26 C25 O3 116.5(3) . . ?
C26 C25 C24 123.1(3) . . ?
O3 C25 C24 120.5(3) . . ?
C25 C26 C21 119.2(3) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?
C28 C27 C24 117.9(3) . . ?
C28 C27 C30 121.5(3) . . ?
C24 C27 C30 120.6(3) . . ?
C27 C28 C29 123.3(3) . . ?
C27 C28 H28 118.4 . . ?
C29 C28 H28 118.4 . . ?
O4 C29 O3 116.3(3) . . ?
O4 C29 C28 126.3(3) . . ?
O3 C29 C28 117.4(3) . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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 -2.9(5) . . . . ?
C11 C1 C2 C3 178.4(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 3.4(5) . . . . ?
C3 C4 C5 C7 175.9(3) . . . . ?
C3 C4 C5 C6 -3.2(5) . . . . ?
C4 C5 C6 C10 179.0(3) . . . . ?
C7 C5 C6 C10 0.0(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C7 C5 C6 C1 -179.1(3) . . . . ?
C2 C1 C6 C5 3.0(4) . . . . ?
C11 C1 C6 C5 -178.4(3) . . . . ?
C2 C1 C6 C10 -176.0(3) . . . . ?
C11 C1 C6 C10 2.6(5) . . . . ?
C4 C5 C7 C8 -179.5(3) . . . . ?
C6 C5 C7 C8 -0.4(5) . . . . ?
C5 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C8 C9 C10 C6 -1.0(5) . . . . ?
C8 C9 C10 C21 177.6(3) . . . . ?
C5 C6 C10 C9 0.7(4) . . . . ?
C1 C6 C10 C9 179.7(3) . . . . ?
C5 C6 C10 C21 -177.8(3) . . . . ?
C1 C6 C10 C21 1.2(5) . . . . ?
C2 C1 C11 C16 -117.5(3) . . . . ?
C6 C1 C11 C16 63.9(4) . . . . ?
C2 C1 C11 C12 62.0(4) . . . . ?
C6 C1 C11 C12 -116.7(3) . . . . ?
C16 C11 C12 C13 -5.7(5) . . . . ?
C1 C11 C12 C13 174.8(3) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 3.6(5) . . . . ?
C12 C13 C14 C17 -172.4(3) . . . . ?
C19 O1 C15 C16 -173.4(3) . . . . ?
C19 O1 C15 C14 4.5(4) . . . . ?
C13 C14 C15 C16 -3.0(4) . . . . ?
C17 C14 C15 C16 173.4(3) . . . . ?
C13 C14 C15 O1 179.2(3) . . . . ?
C17 C14 C15 O1 -4.5(4) . . . . ?
O1 C15 C16 C11 175.9(2) . . . . ?
C14 C15 C16 C11 -2.0(4) . . . . ?
C12 C11 C16 C15 6.3(4) . . . . ?
C1 C11 C16 C15 -174.2(3) . . . . ?
C13 C14 C17 C18 177.6(3) . . . . ?
C15 C14 C17 C18 1.6(4) . . . . ?
C13 C14 C17 C20 -0.6(5) . . . . ?
C15 C14 C17 C20 -176.6(3) . . . . ?
C14 C17 C18 C19 1.3(5) . . . . ?
C20 C17 C18 C19 179.5(3) . . . . ?
C15 O1 C19 O2 179.1(3) . . . . ?
C15 O1 C19 C18 -1.6(4) . . . . ?
C17 C18 C19 O2 177.9(3) . . . . ?
C17 C18 C19 O1 -1.3(5) . . . . ?
C9 C10 C21 C26 67.3(4) . . . . ?
C6 C10 C21 C26 -114.2(3) . . . . ?
C9 C10 C21 C22 -109.2(3) . . . . ?
C6 C10 C21 C22 69.4(4) . . . . ?
C26 C21 C22 C23 2.1(4) . . . . ?
C10 C21 C22 C23 178.6(3) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C22 C23 C24 C25 -1.7(4) . . . . ?
C22 C23 C24 C27 178.6(3) . . . . ?
C29 O3 C25 C26 179.3(3) . . . . ?
C29 O3 C25 C24 -0.5(4) . . . . ?
C23 C24 C25 C26 1.4(4) . . . . ?
C27 C24 C25 C26 -178.9(3) . . . . ?
C23 C24 C25 O3 -178.9(3) . . . . ?
C27 C24 C25 O3 0.8(4) . . . . ?
O3 C25 C26 C21 -179.1(3) . . . . ?
C24 C25 C26 C21 0.7(4) . . . . ?
C22 C21 C26 C25 -2.4(4) . . . . ?
C10 C21 C26 C25 -178.9(3) . . . . ?
C25 C24 C27 C28 0.8(4) . . . . ?
C23 C24 C27 C28 -179.5(3) . . . . ?
C25 C24 C27 C30 -178.9(3) . . . . ?
C23 C24 C27 C30 0.7(5) . . . . ?
C24 C27 C28 C29 -2.9(5) . . . . ?
C30 C27 C28 C29 176.8(3) . . . . ?
C25 O3 C29 O4 177.4(3) . . . . ?
C25 O3 C29 C28 -1.5(4) . . . . ?
C27 C28 C29 O4 -175.5(3) . . . . ?
C27 C28 C29 O3 3.3(5) . . . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
_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_Cou-Dur
_database_code_depnum_ccdc_archive 'CCDC 1509579'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2017-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
7-(2,3,5,6-Tetramethylphenyl)-4-methylcoumarin
_chemical_name_common            ?
_chemical_melting_point          '158-160 degree C'
_chemical_formula_moiety         'C20 H20 O2'
_chemical_formula_sum            'C20 H20 O2'
_chemical_formula_weight         292.36

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                   11.798(5)
_cell_length_b                   12.109(5)
_cell_length_c                   12.211(5)
_cell_angle_alpha                95.007(5)
_cell_angle_beta                 102.009(5)
_cell_angle_gamma                110.256(5)
_cell_volume                     1576.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4632
_cell_measurement_theta_min      2.084
_cell_measurement_theta_max      28.426

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23585
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         28.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7893
_reflns_number_gt                4632
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'



_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1226P)²+2.4639P] 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         7893
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2558
_refine_ls_wR_factor_gt          0.2180
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35785(19) 0.41023(19) 0.24749(18) 0.0237(5) Uani 1 1 d . . . . .
O3 O 0.06425(19) 0.20891(18) 0.92663(18) 0.0230(5) Uani 1 1 d . . . . .
O2 O 0.4430(2) 0.3149(2) 0.1484(2) 0.0315(6) Uani 1 1 d . . . . .
O4 O -0.0923(2) 0.1976(2) 1.0027(2) 0.0323(6) Uani 1 1 d . . . . .
C11 C 0.1937(3) 0.6411(3) 0.4716(3) 0.0209(6) Uani 1 1 d . . . . .
C6 C 0.2745(3) 0.5191(3) 0.3540(2) 0.0201(6) Uani 1 1 d . . . . .
H6 H 0.3452 0.5870 0.3599 0.024 Uiso 1 1 calc R U . . .
C25 C 0.1759(3) 0.2749(3) 0.9040(2) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.2455(3) 0.2004(3) 0.1732(3) 0.0247(7) Uani 1 1 d . . . . .
H2 H 0.2412 0.1303 0.1316 0.030 Uiso 1 1 calc R U . . .
C28 C 0.3939(3) 0.3964(3) 0.8485(2) 0.0206(6) Uani 1 1 d . . . . .
H28 H 0.4673 0.4380 0.8289 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2616(3) 0.4110(3) 0.2949(2) 0.0184(6) Uani 1 1 d . . . . .
C24 C 0.2324(3) 0.3981(3) 0.9409(2) 0.0197(6) Uani 1 1 d . . . . .
C23 C 0.1749(3) 0.4558(3) 1.0093(2) 0.0207(6) Uani 1 1 d . . . . .
C12 C 0.2395(3) 0.6626(3) 0.5903(3) 0.0218(6) Uani 1 1 d . . . . .
C14 C 0.2214(3) 0.8537(3) 0.5961(3) 0.0244(7) Uani 1 1 d . . . . .
H14 H 0.2340 0.9270 0.6376 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1568(3) 0.3068(3) 0.2828(2) 0.0204(6) Uani 1 1 d . . . . .
C32 C 0.3918(3) 0.2214(3) 0.6341(3) 0.0227(7) Uani 1 1 d . . . . .
C7 C 0.1814(3) 0.5260(3) 0.4044(2) 0.0217(6) Uani 1 1 d . . . . .
C13 C 0.2533(3) 0.7704(3) 0.6535(3) 0.0232(7) Uani 1 1 d . . . . .
C15 C 0.1718(3) 0.8322(3) 0.4801(3) 0.0264(7) Uani 1 1 d . . . . .
C31 C 0.3998(3) 0.2113(3) 0.7492(2) 0.0196(6) Uani 1 1 d . . . . .
C22 C 0.0678(3) 0.3887(3) 1.0312(3) 0.0238(7) Uani 1 1 d . . . . .
H22 H 0.0315 0.4256 1.0757 0.029 Uiso 1 1 calc R U . . .
C34 C 0.5339(3) 0.1194(3) 0.6341(3) 0.0235(7) Uani 1 1 d . . . . .
H34 H 0.5799 0.0891 0.5956 0.028 Uiso 1 1 calc R U . . .
C36 C 0.4723(3) 0.1533(3) 0.8057(2) 0.0201(6) Uani 1 1 d . . . . .
C3 C 0.1502(3) 0.1970(3) 0.2187(3) 0.0226(7) Uani 1 1 d . . . . .
C40 C 0.4801(3) 0.1432(3) 0.9292(3) 0.0273(7) Uani 1 1 d . . . . .
H40A H 0.4267 0.0646 0.9346 0.041 Uiso 1 1 calc R U . . .
H40B H 0.4540 0.2015 0.9636 0.041 Uiso 1 1 calc R U . . .
H40C H 0.5648 0.1572 0.9680 0.041 Uiso 1 1 calc R U . . .
C16 C 0.1572(3) 0.7241(3) 0.4163(3) 0.0235(7) Uani 1 1 d . . . . .
C9 C 0.0639(3) 0.3163(3) 0.3328(3) 0.0264(7) Uani 1 1 d . . . . .
H9 H -0.0075 0.2489 0.3258 0.032 Uiso 1 1 calc R U . . .
C35 C 0.5400(3) 0.1064(3) 0.7473(3) 0.0234(7) Uani 1 1 d . . . . .
C29 C 0.3428(3) 0.4580(3) 0.9111(2) 0.0206(6) Uani 1 1 d . . . . .
H29 H 0.3825 0.5403 0.9336 0.025 Uiso 1 1 calc R U . . .
C27 C 0.3373(3) 0.2728(3) 0.8143(2) 0.0208(6) Uani 1 1 d . . . . .
C26 C 0.2268(3) 0.2120(3) 0.8419(2) 0.0215(6) Uani 1 1 d . . . . .
H26 H 0.1871 0.1297 0.8190 0.026 Uiso 1 1 calc R U . . .
C1 C 0.3540(3) 0.3072(3) 0.1858(3) 0.0226(7) Uani 1 1 d . . . . .
C37 C 0.3120(4) 0.2816(3) 0.5726(3) 0.0330(8) Uani 1 1 d . . . . .
H37A H 0.2703 0.3075 0.6231 0.049 Uiso 1 1 calc R U . . .
H37B H 0.3637 0.3494 0.5469 0.049 Uiso 1 1 calc R U . . .
H37C H 0.2510 0.2262 0.5083 0.049 Uiso 1 1 calc R U . . .
C8 C 0.0752(3) 0.4228(3) 0.3921(3) 0.0281(7) Uani 1 1 d . . . . .
H8 H 0.0116 0.4264 0.4244 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2986(3) 0.7955(3) 0.7804(3) 0.0346(8) Uani 1 1 d . . . . .
H18A H 0.3164 0.7292 0.8061 0.052 Uiso 1 1 calc R U . . .
H18B H 0.3732 0.8664 0.8035 0.052 Uiso 1 1 calc R U . . .
H18C H 0.2353 0.8072 0.8129 0.052 Uiso 1 1 calc R U . . .
C30 C 0.2369(3) 0.5866(3) 1.0546(3) 0.0265(7) Uani 1 1 d . . . . .
H30A H 0.3120 0.6186 1.0298 0.040 Uiso 1 1 calc R U . . .
H30B H 0.1813 0.6259 1.0269 0.040 Uiso 1 1 calc R U . . .
H30C H 0.2571 0.5995 1.1362 0.040 Uiso 1 1 calc R U . . .
C33 C 0.4620(3) 0.1759(3) 0.5770(3) 0.0221(6) Uani 1 1 d . . . . .
C10 C 0.0390(3) 0.0848(3) 0.2040(3) 0.0305(8) Uani 1 1 d . . . . .
H10A H -0.0184 0.1004 0.2425 0.046 Uiso 1 1 calc R U . . .
H10B H -0.0012 0.0568 0.1245 0.046 Uiso 1 1 calc R U . . .
H10C H 0.0652 0.0251 0.2356 0.046 Uiso 1 1 calc R U . . .
C17 C 0.2706(3) 0.5692(3) 0.6508(3) 0.0323(8) Uani 1 1 d . . . . .
H17A H 0.2563 0.5008 0.5959 0.049 Uiso 1 1 calc R U . . .
H17B H 0.3567 0.6018 0.6928 0.049 Uiso 1 1 calc R U . . .
H17C H 0.2185 0.5455 0.7020 0.049 Uiso 1 1 calc R U . . .
C39 C 0.6216(3) 0.0447(3) 0.8050(3) 0.0299(8) Uani 1 1 d . . . . .
H39A H 0.6586 0.0166 0.7512 0.045 Uiso 1 1 calc R U . . .
H39B H 0.5717 -0.0217 0.8335 0.045 Uiso 1 1 calc R U . . .
H39C H 0.6863 0.1002 0.8669 0.045 Uiso 1 1 calc R U . . .
C21 C 0.0059(3) 0.2623(3) 0.9892(3) 0.0236(7) Uani 1 1 d . . . . .
C19 C 0.1316(4) 0.9234(3) 0.4242(3) 0.0397(9) Uani 1 1 d . . . . .
H19A H 0.0994 0.8950 0.3438 0.060 Uiso 1 1 calc R U . . .
H19B H 0.0678 0.9360 0.4552 0.060 Uiso 1 1 calc R U . . .
H19C H 0.2020 0.9974 0.4379 0.060 Uiso 1 1 calc R U . . .
C38 C 0.4605(3) 0.1886(3) 0.4549(3) 0.0310(8) Uani 1 1 d . . . . .
H38A H 0.4063 0.2295 0.4280 0.047 Uiso 1 1 calc R U . . .
H38B H 0.5435 0.2335 0.4499 0.047 Uiso 1 1 calc R U . . .
H38C H 0.4306 0.1107 0.4090 0.047 Uiso 1 1 calc R U . . .
C20 C 0.0999(4) 0.6979(4) 0.2901(3) 0.0373(9) Uani 1 1 d . . . . .
H20A H 0.0966 0.6209 0.2590 0.056 Uiso 1 1 calc R U . . .
H20B H 0.0169 0.6982 0.2757 0.056 Uiso 1 1 calc R U . . .
H20C H 0.1497 0.7580 0.2549 0.056 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
O1 C5 1.380(3) . ?
O1 C1 1.381(4) . ?
O3 C25 1.383(4) . ?
O3 C21 1.385(4) . ?
O2 C1 1.207(4) . ?
O4 C21 1.207(4) . ?
C11 C16 1.396(4) . ?
C11 C12 1.404(4) . ?
C11 C7 1.499(4) . ?
C6 C5 1.382(4) . ?
C6 C7 1.389(4) . ?
C6 H6 0.9300 . ?
C25 C26 1.385(4) . ?
C25 C24 1.394(4) . ?
C2 C3 1.344(4) . ?
C2 C1 1.440(4) . ?
C2 H2 0.9300 . ?
C28 C29 1.381(4) . ?
C28 C27 1.394(4) . ?
C28 H28 0.9300 . ?
C5 C4 1.398(4) . ?
C24 C29 1.394(4) . ?
C24 C23 1.452(4) . ?
C23 C22 1.341(4) . ?
C23 C30 1.492(4) . ?
C12 C13 1.396(4) . ?
C12 C17 1.509(4) . ?
C14 C15 1.380(5) . ?
C14 C13 1.388(4) . ?
C14 H14 0.9300 . ?
C4 C9 1.393(4) . ?
C4 C3 1.452(4) . ?
C32 C33 1.401(4) . ?
C32 C31 1.408(4) . ?
C32 C37 1.503(4) . ?
C7 C8 1.400(4) . ?
C13 C18 1.497(4) . ?
C15 C16 1.400(5) . ?
C15 C19 1.507(5) . ?
C31 C36 1.398(4) . ?
C31 C27 1.500(4) . ?
C22 C21 1.439(5) . ?
C22 H22 0.9300 . ?
C34 C33 1.382(4) . ?
C34 C35 1.395(4) . ?
C34 H34 0.9300 . ?
C36 C35 1.396(4) . ?
C36 C40 1.510(4) . ?
C3 C10 1.491(4) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C16 C20 1.506(4) . ?
C9 C8 1.371(5) . ?
C9 H9 0.9300 . ?
C35 C39 1.512(4) . ?
C29 H29 0.9300 . ?
C27 C26 1.384(4) . ?
C26 H26 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C8 H8 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C33 C38 1.510(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C5 O1 C1 121.5(2) . . ?
C25 O3 C21 121.2(2) . . ?
C16 C11 C12 120.9(3) . . ?
C16 C11 C7 120.0(3) . . ?
C12 C11 C7 119.1(3) . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
O3 C25 C26 116.4(3) . . ?
O3 C25 C24 121.3(3) . . ?
C26 C25 C24 122.4(3) . . ?
C3 C2 C1 123.1(3) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C29 C28 C27 121.0(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
O1 C5 C6 116.7(3) . . ?
O1 C5 C4 121.0(3) . . ?
C6 C5 C4 122.3(3) . . ?
C29 C24 C25 117.4(3) . . ?
C29 C24 C23 124.1(3) . . ?
C25 C24 C23 118.5(3) . . ?
C22 C23 C24 118.5(3) . . ?
C22 C23 C30 121.9(3) . . ?
C24 C23 C30 119.6(3) . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 C17 119.6(3) . . ?
C11 C12 C17 120.8(3) . . ?
C15 C14 C13 122.7(3) . . ?
C15 C14 H14 118.7 . . ?
C13 C14 H14 118.7 . . ?
C9 C4 C5 116.9(3) . . ?
C9 C4 C3 124.2(3) . . ?
C5 C4 C3 118.8(3) . . ?
C33 C32 C31 118.8(3) . . ?
C33 C32 C37 119.8(3) . . ?
C31 C32 C37 121.5(3) . . ?
C6 C7 C8 118.7(3) . . ?
C6 C7 C11 121.1(3) . . ?
C8 C7 C11 120.2(3) . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 C18 120.2(3) . . ?
C12 C13 C18 121.3(3) . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 C19 119.9(3) . . ?
C16 C15 C19 121.0(3) . . ?
C36 C31 C32 121.3(3) . . ?
C36 C31 C27 119.6(3) . . ?
C32 C31 C27 118.8(3) . . ?
C23 C22 C21 123.3(3) . . ?
C23 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
C33 C34 C35 122.4(3) . . ?
C33 C34 H34 118.8 . . ?
C35 C34 H34 118.8 . . ?
C31 C36 C35 119.3(3) . . ?
C31 C36 C40 120.8(3) . . ?
C35 C36 C40 119.8(3) . . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 C10 121.9(3) . . ?
C4 C3 C10 119.8(3) . . ?
C36 C40 H40A 109.5 . . ?
C36 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C36 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C15 C16 C11 119.2(3) . . ?
C15 C16 C20 119.7(3) . . ?
C11 C16 C20 121.1(3) . . ?
C8 C9 C4 121.6(3) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
C34 C35 C36 118.8(3) . . ?
C34 C35 C39 119.7(3) . . ?
C36 C35 C39 121.4(3) . . ?
C28 C29 C24 120.8(3) . . ?
C28 C29 H29 119.6 . . ?
C24 C29 H29 119.6 . . ?
C26 C27 C28 119.0(3) . . ?
C26 C27 C31 122.9(3) . . ?
C28 C27 C31 118.1(3) . . ?
C27 C26 C25 119.4(3) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
O2 C1 O1 116.8(3) . . ?
O2 C1 C2 125.9(3) . . ?
O1 C1 C2 117.3(3) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C34 C33 C32 119.2(3) . . ?
C34 C33 C38 119.9(3) . . ?
C32 C33 C38 120.8(3) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C35 C39 H39A 109.5 . . ?
C35 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C35 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O4 C21 O3 116.2(3) . . ?
O4 C21 C22 126.7(3) . . ?
O3 C21 C22 117.1(3) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C33 C38 H38A 109.5 . . ?
C33 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C33 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C21 O3 C25 C26 179.1(3) . . . . ?
C21 O3 C25 C24 -1.6(4) . . . . ?
C1 O1 C5 C6 -179.4(3) . . . . ?
C1 O1 C5 C4 0.5(4) . . . . ?
C7 C6 C5 O1 -179.6(3) . . . . ?
C7 C6 C5 C4 0.5(4) . . . . ?
O3 C25 C24 C29 -178.0(3) . . . . ?
C26 C25 C24 C29 1.2(4) . . . . ?
O3 C25 C24 C23 3.2(4) . . . . ?
C26 C25 C24 C23 -177.6(3) . . . . ?
C29 C24 C23 C22 179.2(3) . . . . ?
C25 C24 C23 C22 -2.1(4) . . . . ?
C29 C24 C23 C30 -1.6(4) . . . . ?
C25 C24 C23 C30 177.1(3) . . . . ?
C16 C11 C12 C13 -2.5(4) . . . . ?
C7 C11 C12 C13 179.0(3) . . . . ?
C16 C11 C12 C17 175.8(3) . . . . ?
C7 C11 C12 C17 -2.8(4) . . . . ?
O1 C5 C4 C9 -179.5(3) . . . . ?
C6 C5 C4 C9 0.4(4) . . . . ?
O1 C5 C4 C3 -0.3(4) . . . . ?
C6 C5 C4 C3 179.6(3) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C5 C6 C7 C11 178.5(3) . . . . ?
C16 C11 C7 C6 85.5(4) . . . . ?
C12 C11 C7 C6 -96.0(4) . . . . ?
C16 C11 C7 C8 -94.9(4) . . . . ?
C12 C11 C7 C8 83.6(4) . . . . ?
C15 C14 C13 C12 2.9(5) . . . . ?
C15 C14 C13 C18 -175.8(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C17 C12 C13 C14 -178.6(3) . . . . ?
C11 C12 C13 C18 178.4(3) . . . . ?
C17 C12 C13 C18 0.1(5) . . . . ?
C13 C14 C15 C16 -2.6(5) . . . . ?
C13 C14 C15 C19 176.1(3) . . . . ?
C33 C32 C31 C36 -2.4(5) . . . . ?
C37 C32 C31 C36 178.7(3) . . . . ?
C33 C32 C31 C27 172.7(3) . . . . ?
C37 C32 C31 C27 -6.1(5) . . . . ?
C24 C23 C22 C21 -0.7(4) . . . . ?
C30 C23 C22 C21 -179.8(3) . . . . ?
C32 C31 C36 C35 1.3(4) . . . . ?
C27 C31 C36 C35 -173.8(3) . . . . ?
C32 C31 C36 C40 179.9(3) . . . . ?
C27 C31 C36 C40 4.9(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C10 180.0(3) . . . . ?
C9 C4 C3 C2 179.0(3) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C9 C4 C3 C10 -0.5(5) . . . . ?
C5 C4 C3 C10 -179.6(3) . . . . ?
C14 C15 C16 C11 -0.2(5) . . . . ?
C19 C15 C16 C11 -179.0(3) . . . . ?
C14 C15 C16 C20 178.3(3) . . . . ?
C19 C15 C16 C20 -0.4(5) . . . . ?
C12 C11 C16 C15 2.8(4) . . . . ?
C7 C11 C16 C15 -178.7(3) . . . . ?
C12 C11 C16 C20 -175.8(3) . . . . ?
C7 C11 C16 C20 2.7(4) . . . . ?
C5 C4 C9 C8 -0.6(5) . . . . ?
C3 C4 C9 C8 -179.7(3) . . . . ?
C33 C34 C35 C36 -0.8(5) . . . . ?
C33 C34 C35 C39 -179.4(3) . . . . ?
C31 C36 C35 C34 0.4(4) . . . . ?
C40 C36 C35 C34 -178.3(3) . . . . ?
C31 C36 C35 C39 178.9(3) . . . . ?
C40 C36 C35 C39 0.2(5) . . . . ?
C27 C28 C29 C24 -0.5(4) . . . . ?
C25 C24 C29 C28 -0.7(4) . . . . ?
C23 C24 C29 C28 178.0(3) . . . . ?
C29 C28 C27 C26 1.3(4) . . . . ?
C29 C28 C27 C31 -178.4(3) . . . . ?
C36 C31 C27 C26 -79.9(4) . . . . ?
C32 C31 C27 C26 104.9(4) . . . . ?
C36 C31 C27 C28 99.8(3) . . . . ?
C32 C31 C27 C28 -75.4(4) . . . . ?
C28 C27 C26 C25 -0.8(4) . . . . ?
C31 C27 C26 C25 178.9(3) . . . . ?
O3 C25 C26 C27 178.8(3) . . . . ?
C24 C25 C26 C27 -0.5(4) . . . . ?
C5 O1 C1 O2 -179.4(3) . . . . ?
C5 O1 C1 C2 -0.2(4) . . . . ?
C3 C2 C1 O2 178.8(3) . . . . ?
C3 C2 C1 O1 -0.3(4) . . . . ?
C4 C9 C8 C7 -0.1(5) . . . . ?
C6 C7 C8 C9 1.0(5) . . . . ?
C11 C7 C8 C9 -178.7(3) . . . . ?
C35 C34 C33 C32 -0.3(5) . . . . ?
C35 C34 C33 C38 179.2(3) . . . . ?
C31 C32 C33 C34 1.9(5) . . . . ?
C37 C32 C33 C34 -179.2(3) . . . . ?
C31 C32 C33 C38 -177.7(3) . . . . ?
C37 C32 C33 C38 1.2(5) . . . . ?
C25 O3 C21 O4 178.8(3) . . . . ?
C25 O3 C21 C22 -1.1(4) . . . . ?
C23 C22 C21 O4 -177.6(3) . . . . ?
C23 C22 C21 O3 2.2(4) . . . . ?

_refine_diff_density_max         0.619
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.080


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
_exptl_crystal_preparation       ', Luminescent'
