# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1476770'
_audit_update_record             
;
2016-04-27 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H16'
_chemical_formula_iupac          ?
_chemical_formula_weight         364.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.856(2)
_cell_length_b                   7.3071(12)
_cell_length_c                   20.186(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.412(5)
_cell_angle_gamma                90
_cell_volume                     1737.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2279
_cell_measurement_theta_min      2.5156
_cell_measurement_theta_max      21.6891
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            38966
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             4307
_reflns_number_gt                2739
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1308
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_number_reflns         4307
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.7761P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.88633(17) 0.3550(3) 0.33946(10) 0.0252(5) Uani d . . . 1 . .
C C2 0.94647(17) 0.5061(3) 0.31773(10) 0.0268(5) Uani d . . . 1 . .
H H2 1.0256 0.4958 0.3146 0.032 Uiso calc U . R 1 . .
C C3 0.89186(17) 0.6677(3) 0.30115(10) 0.0258(5) Uani d . . . 1 . .
H H3 0.9332 0.7664 0.285 0.031 Uiso calc U . R 1 . .
C C4 0.77532(16) 0.6901(3) 0.30760(10) 0.0226(4) Uani d . . . 1 . .
C C5 0.71799(17) 0.8563(3) 0.28968(10) 0.0254(5) Uani d . . . 1 . .
H H5 0.7587 0.9555 0.2733 0.03 Uiso calc U . R 1 . .
C C6 0.60566(16) 0.8755(3) 0.29556(10) 0.0236(4) Uani d . . . 1 . .
H H6 0.5687 0.9862 0.2813 0.028 Uiso calc U . R 1 . .
C C7 0.54170(16) 0.7347(2) 0.32249(9) 0.0204(4) Uani d . . . 1 . .
C C8 0.42184(16) 0.7662(2) 0.32972(9) 0.0206(4) Uani d . . . 1 . .
C C9 0.35971(17) 0.9360(3) 0.33002(10) 0.0238(4) Uani d . . . 1 . .
H H9 0.3909 1.0429 0.3124 0.029 Uiso calc U . R 1 . .
C C10 0.25601(16) 0.9479(3) 0.35517(10) 0.0247(4) Uani d . . . 1 . .
H H10 0.2175 1.0621 0.3535 0.03 Uiso calc U . R 1 . .
C C11 0.20485(16) 0.7922(3) 0.38380(10) 0.0234(4) Uani d . . . 1 . .
C C12 0.12367(17) 0.7861(3) 0.43202(11) 0.0275(5) Uani d . . . 1 . .
H H12 0.0773 0.8901 0.437 0.033 Uiso calc U . R 1 . .
C C13 0.11140(17) 0.6342(3) 0.47110(11) 0.0266(5) Uani d . . . 1 . .
H H13 0.0564 0.6365 0.5019 0.032 Uiso calc U . R 1 . .
C C14 0.17975(16) 0.4713(3) 0.46665(10) 0.0237(4) Uani d . . . 1 . .
C C15 0.20629(17) 0.3277(3) 0.51523(10) 0.0258(5) Uani d . . . 1 . .
H H15 0.1544 0.3021 0.5466 0.031 Uiso calc U . R 1 . .
C C16 0.30523(17) 0.2269(3) 0.51710(10) 0.0249(4) Uani d . . . 1 . .
H H16 0.3199 0.1343 0.55 0.03 Uiso calc U . R 1 . .
C C17 0.38684(16) 0.2587(2) 0.47041(10) 0.0222(4) Uani d . . . 1 . .
C C18 0.50719(16) 0.2270(3) 0.47692(10) 0.0236(4) Uani d . . . 1 . .
H H18 0.5395 0.1468 0.5109 0.028 Uiso calc U . R 1 . .
C C19 0.57748(17) 0.3089(2) 0.43562(10) 0.0222(4) Uani d . . . 1 . .
H H19 0.6564 0.2827 0.4424 0.027 Uiso calc U . R 1 . .
C C20 0.53628(16) 0.4333(2) 0.38230(9) 0.0200(4) Uani d . . . 1 . .
C C21 0.59746(16) 0.5682(2) 0.34489(10) 0.0210(4) Uani d . . . 1 . .
C C22 0.71435(16) 0.5429(3) 0.33317(10) 0.0212(4) Uani d . . . 1 . .
C C23 0.77255(17) 0.3739(3) 0.34562(10) 0.0240(4) Uani d . . . 1 . .
H H23 0.7315 0.2707 0.3586 0.029 Uiso calc U . R 1 . .
C C24 0.36416(16) 0.6164(2) 0.34892(9) 0.0202(4) Uani d . . . 1 . .
C C25 0.25828(16) 0.6277(3) 0.37472(10) 0.0216(4) Uani d . . . 1 . .
C C26 0.24708(16) 0.4730(2) 0.41564(10) 0.0212(4) Uani d . . . 1 . .
C C27 0.34814(16) 0.3687(2) 0.41697(10) 0.0204(4) Uani d . . . 1 . .
C C28 0.42040(16) 0.4540(2) 0.37522(9) 0.0196(4) Uani d . . . 1 . .
C C29 0.94801(18) 0.1773(3) 0.35677(12) 0.0317(5) Uani d . . . 1 . .
H H29A 0.8967 0.0916 0.3757 0.048 Uiso calc U . R 1 . .
H H29B 1.0139 0.2009 0.3894 0.048 Uiso calc U . R 1 . .
H H29C 0.9734 0.1242 0.3164 0.048 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C23 . 1.375(3) ?
C1 C2 . 1.411(3) ?
C1 C29 . 1.512(3) ?
C2 C3 . 1.370(3) ?
C3 C4 . 1.412(3) ?
C4 C5 . 1.418(3) ?
C4 C22 . 1.425(3) ?
C5 C6 . 1.357(3) ?
C6 C7 . 1.422(3) ?
C7 C21 . 1.433(3) ?
C7 C8 . 1.463(3) ?
C8 C24 . 1.369(3) ?
C8 C9 . 1.443(3) ?
C9 C10 . 1.384(3) ?
C10 C11 . 1.441(3) ?
C11 C25 . 1.380(3) ?
C11 C12 . 1.444(3) ?
C12 C13 . 1.379(3) ?
C13 C14 . 1.448(3) ?
C14 C26 . 1.372(3) ?
C14 C15 . 1.447(3) ?
C15 C16 . 1.382(3) ?
C16 C17 . 1.443(3) ?
C17 C27 . 1.382(3) ?
C17 C18 . 1.437(3) ?
C18 C19 . 1.379(3) ?
C19 C20 . 1.451(3) ?
C20 C28 . 1.374(3) ?
C20 C21 . 1.480(3) ?
C21 C22 . 1.444(3) ?
C22 C23 . 1.423(3) ?
C24 C25 . 1.414(3) ?
C24 C28 . 1.434(3) ?
C25 C26 . 1.415(3) ?
C26 C27 . 1.418(3) ?
C27 C28 . 1.412(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 C1 C2 . . 118.97(18) ?
C23 C1 C29 . . 121.29(18) ?
C2 C1 C29 . . 119.73(18) ?
C3 C2 C1 . . 120.60(18) ?
C2 C3 C4 . . 121.23(19) ?
C3 C4 C5 . . 121.48(18) ?
C3 C4 C22 . . 119.13(18) ?
C5 C4 C22 . . 119.39(18) ?
C6 C5 C4 . . 120.85(18) ?
C5 C6 C7 . . 121.96(18) ?
C6 C7 C21 . . 119.19(17) ?
C6 C7 C8 . . 119.33(17) ?
C21 C7 C8 . . 121.41(17) ?
C24 C8 C9 . . 114.50(17) ?
C24 C8 C7 . . 115.07(16) ?
C9 C8 C7 . . 129.63(17) ?
C10 C9 C8 . . 122.02(18) ?
C9 C10 C11 . . 121.90(17) ?
C25 C11 C10 . . 114.48(18) ?
C25 C11 C12 . . 114.42(18) ?
C10 C11 C12 . . 129.55(18) ?
C13 C12 C11 . . 122.08(18) ?
C12 C13 C14 . . 122.04(19) ?
C26 C14 C15 . . 114.49(18) ?
C26 C14 C13 . . 114.59(18) ?
C15 C14 C13 . . 129.41(19) ?
C16 C15 C14 . . 121.65(19) ?
C15 C16 C17 . . 121.71(18) ?
C27 C17 C18 . . 113.86(18) ?
C27 C17 C16 . . 114.52(17) ?
C18 C17 C16 . . 130.24(18) ?
C19 C18 C17 . . 122.40(18) ?
C18 C19 C20 . . 122.94(18) ?
C28 C20 C19 . . 113.35(17) ?
C28 C20 C21 . . 114.51(16) ?
C19 C20 C21 . . 130.69(17) ?
C7 C21 C22 . . 118.33(17) ?
C7 C21 C20 . . 119.42(17) ?
C22 C21 C20 . . 122.16(17) ?
C23 C22 C4 . . 117.62(17) ?
C23 C22 C21 . . 122.53(17) ?
C4 C22 C21 . . 119.84(17) ?
C1 C23 C22 . . 122.16(18) ?
C8 C24 C25 . . 123.32(17) ?
C8 C24 C28 . . 122.69(17) ?
C25 C24 C28 . . 107.90(17) ?
C11 C25 C24 . . 122.65(18) ?
C11 C25 C26 . . 122.94(18) ?
C24 C25 C26 . . 108.24(16) ?
C14 C26 C25 . . 123.05(18) ?
C14 C26 C27 . . 122.86(18) ?
C25 C26 C27 . . 107.84(17) ?
C17 C27 C28 . . 123.51(18) ?
C17 C27 C26 . . 122.25(18) ?
C28 C27 C26 . . 108.61(16) ?
C20 C28 C27 . . 123.75(17) ?
C20 C28 C24 . . 123.25(17) ?
C27 C28 C24 . . 107.36(16) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1476771'
_audit_update_record             
;
2016-04-27 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_chemical_name_systematic        
acenaphtho[3',2',1',8':9,10,11,12]chryseno[2,1-b]benzo[d]thiophene
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H14 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         406.47
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
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                   9.2775(6)
_cell_length_b                   26.8593(15)
_cell_length_c                   7.3125(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1822.18(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2785
_cell_measurement_theta_min      2.6684
_cell_measurement_theta_max      25.2694
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840

_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10184
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             3608
_reflns_number_gt                2585
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1161
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     281
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.2386P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.361
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(18)

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5480(5) 0.20600(17) 0.4104(7) 0.0121(11) Uani d . . . 1 . .
C C2 0.5257(6) 0.25177(18) 0.4888(7) 0.0153(12) Uani d . . . 1 . .
C C3 0.3919(5) 0.25549(18) 0.5897(7) 0.0145(12) Uani d . . . 1 . .
H H3 0.3655 0.2868 0.6398 0.017 Uiso calc U . R 1 . .
C C4 0.3014(5) 0.21568(16) 0.6162(7) 0.0146(12) Uani d . . . 1 . .
H H4 0.2141 0.2206 0.6816 0.018 Uiso calc U . R 1 . .
C C5 0.3349(5) 0.16632(18) 0.5475(7) 0.0149(12) Uani d . . . 1 . .
C C6 0.4553(5) 0.16493(17) 0.4389(7) 0.0116(12) Uani d . . . 1 . .
C C7 0.5337(5) 0.12088(17) 0.4051(7) 0.0135(11) Uani d . . . 1 . .
C C8 0.4961(5) 0.07560(18) 0.4815(7) 0.0138(11) Uani d . . . 1 . .
C C9 0.3594(5) 0.07550(19) 0.5766(7) 0.0175(13) Uani d . . . 1 . .
H H9 0.3218 0.0448 0.6201 0.021 Uiso calc U . R 1 . .
C C10 0.2828(5) 0.11819(17) 0.6060(7) 0.0145(12) Uani d . . . 1 . .
H H10 0.1924 0.1162 0.6667 0.017 Uiso calc U . R 1 . .
C C11 0.6127(6) 0.03968(18) 0.4853(8) 0.0187(13) Uani d . . . 1 . .
H H11 0.5923 0.0061 0.5169 0.022 Uiso calc U . R 1 . .
C C12 0.7509(6) 0.05284(18) 0.4446(6) 0.0154(12) Uani d . . . 1 . .
H H12 0.8236 0.028 0.4492 0.018 Uiso calc U . R 1 . .
C C13 0.7913(5) 0.10280(17) 0.3951(8) 0.0147(11) Uani d . . . 1 . .
C C14 0.6761(5) 0.13389(17) 0.3626(6) 0.0106(11) Uani d . . . 1 . .
C C15 0.6871(5) 0.18631(17) 0.3663(7) 0.0129(11) Uani d . . . 1 . .
C C16 0.8114(5) 0.21073(17) 0.4096(7) 0.0132(11) Uani d . . . 1 . .
C C17 0.9363(5) 0.17929(18) 0.4195(7) 0.0164(12) Uani d . . . 1 . .
H H17 1.0286 0.1942 0.4326 0.02 Uiso calc U . R 1 . .
C C18 0.9265(5) 0.12817(18) 0.4108(7) 0.0172(12) Uani d . . . 1 . .
H H18 1.0125 0.109 0.4153 0.021 Uiso calc U . R 1 . .
C C19 0.7946(6) 0.26322(18) 0.4648(7) 0.0155(12) Uani d . . . 1 . .
C C20 0.6534(6) 0.28434(18) 0.4899(7) 0.0158(12) Uani d . . . 1 . .
C C21 0.6447(6) 0.33640(19) 0.5305(7) 0.0168(13) Uani d . . . 1 . .
C C22 0.7727(6) 0.36180(18) 0.5756(7) 0.0202(13) Uani d . . . 1 . .
C C23 0.9077(6) 0.3404(2) 0.5618(7) 0.0189(13) Uani d . . . 1 . .
H H23 0.9919 0.3587 0.5931 0.023 Uiso calc U . R 1 . .
C C24 0.9170(6) 0.29213(19) 0.5018(7) 0.0186(12) Uani d . . . 1 . .
H H24 1.0096 0.2778 0.4847 0.022 Uiso calc U . R 1 . .
C C25 0.5237(6) 0.37046(19) 0.5178(7) 0.0176(13) Uani d . . . 1 . .
C C26 0.3866(6) 0.36421(19) 0.4405(7) 0.0200(13) Uani d . . . 1 . .
H H26 0.3579 0.3322 0.3989 0.024 Uiso calc U . R 1 . .
C C27 0.2927(6) 0.40382(18) 0.4237(8) 0.0246(14) Uani d . . . 1 . .
H H27 0.2015 0.3991 0.3671 0.029 Uiso calc U . R 1 . .
C C28 0.3307(7) 0.4507(2) 0.4890(8) 0.0296(15) Uani d . . . 1 . .
H H28 0.2637 0.4773 0.4813 0.035 Uiso calc U . R 1 . .
C C29 0.4645(7) 0.4587(2) 0.5648(8) 0.0283(16) Uani d . . . 1 . .
H H29 0.4909 0.4907 0.6087 0.034 Uiso calc U . R 1 . .
C C30 0.5605(6) 0.41883(19) 0.5757(6) 0.0206(13) Uani d . . . 1 . .
S S1 0.74102(19) 0.42364(4) 0.6378(2) 0.0251(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.372(6) ?
C1 C6 . 1.414(6) ?
C1 C15 . 1.432(7) ?
C2 C3 . 1.448(7) ?
C2 C20 . 1.473(7) ?
C3 C4 . 1.373(6) ?
C4 C5 . 1.451(6) ?
C5 C6 . 1.371(7) ?
C5 C10 . 1.445(6) ?
C6 C7 . 1.411(6) ?
C7 C8 . 1.383(6) ?
C7 C14 . 1.402(6) ?
C8 C9 . 1.446(7) ?
C8 C11 . 1.450(7) ?
C9 C10 . 1.366(7) ?
C11 C12 . 1.362(7) ?
C12 C13 . 1.440(6) ?
C13 C14 . 1.377(6) ?
C13 C18 . 1.432(6) ?
C14 C15 . 1.412(6) ?
C15 C16 . 1.364(6) ?
C16 C17 . 1.436(6) ?
C16 C19 . 1.475(6) ?
C17 C18 . 1.377(6) ?
C19 C24 . 1.402(7) ?
C19 C20 . 1.439(7) ?
C20 C21 . 1.432(6) ?
C21 C22 . 1.408(7) ?
C21 C25 . 1.451(7) ?
C22 C23 . 1.381(8) ?
C22 S1 . 1.747(5) ?
C23 C24 . 1.372(7) ?
C25 C26 . 1.402(7) ?
C25 C30 . 1.408(7) ?
C26 C27 . 1.381(7) ?
C27 C28 . 1.392(7) ?
C28 C29 . 1.376(8) ?
C29 C30 . 1.395(7) ?
C30 S1 . 1.740(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 123.1(5) ?
C2 C1 C15 . . 124.1(5) ?
C6 C1 C15 . . 107.1(4) ?
C1 C2 C3 . . 113.8(5) ?
C1 C2 C20 . . 114.4(5) ?
C3 C2 C20 . . 130.2(5) ?
C4 C3 C2 . . 122.8(5) ?
C3 C4 C5 . . 122.1(5) ?
C6 C5 C10 . . 114.8(5) ?
C6 C5 C4 . . 113.6(5) ?
C10 C5 C4 . . 130.0(5) ?
C5 C6 C7 . . 123.0(5) ?
C5 C6 C1 . . 124.0(5) ?
C7 C6 C1 . . 108.3(4) ?
C8 C7 C14 . . 123.1(4) ?
C8 C7 C6 . . 122.5(5) ?
C14 C7 C6 . . 108.4(4) ?
C7 C8 C9 . . 114.6(5) ?
C7 C8 C11 . . 113.9(4) ?
C9 C8 C11 . . 130.1(5) ?
C10 C9 C8 . . 122.0(5) ?
C9 C10 C5 . . 122.0(5) ?
C12 C11 C8 . . 121.7(5) ?
C11 C12 C13 . . 122.8(4) ?
C14 C13 C18 . . 113.9(4) ?
C14 C13 C12 . . 114.0(4) ?
C18 C13 C12 . . 130.7(5) ?
C13 C14 C7 . . 122.8(4) ?
C13 C14 C15 . . 123.0(5) ?
C7 C14 C15 . . 108.2(4) ?
C16 C15 C14 . . 123.1(4) ?
C16 C15 C1 . . 122.2(4) ?
C14 C15 C1 . . 107.9(4) ?
C15 C16 C17 . . 114.3(4) ?
C15 C16 C19 . . 115.7(4) ?
C17 C16 C19 . . 129.3(4) ?
C18 C17 C16 . . 122.0(5) ?
C17 C18 C13 . . 122.4(5) ?
C24 C19 C20 . . 119.6(5) ?
C24 C19 C16 . . 119.8(5) ?
C20 C19 C16 . . 120.5(4) ?
C21 C20 C19 . . 117.6(5) ?
C21 C20 C2 . . 122.4(5) ?
C19 C20 C2 . . 119.8(4) ?
C22 C21 C20 . . 118.3(5) ?
C22 C21 C25 . . 111.2(5) ?
C20 C21 C25 . . 130.3(5) ?
C23 C22 C21 . . 123.1(5) ?
C23 C22 S1 . . 124.5(4) ?
C21 C22 S1 . . 112.3(4) ?
C24 C23 C22 . . 118.2(5) ?
C23 C24 C19 . . 122.3(5) ?
C26 C25 C30 . . 116.8(5) ?
C26 C25 C21 . . 130.7(5) ?
C30 C25 C21 . . 112.0(5) ?
C27 C26 C25 . . 121.1(5) ?
C26 C27 C28 . . 120.4(6) ?
C29 C28 C27 . . 120.6(6) ?
C28 C29 C30 . . 118.6(5) ?
C29 C30 C25 . . 122.4(5) ?
C29 C30 S1 . . 124.9(4) ?
C25 C30 S1 . . 112.3(4) ?
C30 S1 C22 . . 91.3(3) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1476773'
_audit_update_record             
;
2016-04-27 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_chemical_name_systematic        
acenaphtho[3,2,1,8-stuva]picen-8-yl(methyl)sulfane
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H16 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         396.48

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.111(5)
_cell_length_b                   7.318(3)
_cell_length_c                   18.169(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.411(10)
_cell_angle_gamma                90
_cell_volume                     1845.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1854
_cell_measurement_theta_min      2.2794
_cell_measurement_theta_max      22.3496
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            30616
_diffrn_reflns_av_R_equivalents  0.3024
_diffrn_reflns_av_unetI/netI     0.1909
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3311
_reflns_number_gt                1442
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2103
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1865
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.337
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3211(3) 0.5450(7) 0.4361(3) 0.0219(13) Uani d . . . 1 . .
C C2 0.3864(4) 0.5478(6) 0.3888(3) 0.0191(12) Uani d . . . 1 . .
C C3 0.4665(4) 0.6710(7) 0.4117(3) 0.0239(13) Uani d . . . 1 . .
H H3 0.5129 0.6846 0.3801 0.029 Uiso calc U . R 1 . .
C C4 0.4784(4) 0.7710(7) 0.4783(3) 0.0248(13) Uani d . . . 1 . .
H H4 0.5325 0.8498 0.4905 0.03 Uiso calc U . R 1 . .
C C5 0.4113(4) 0.7579(7) 0.5286(3) 0.0233(13) Uani d . . . 1 . .
C C6 0.3323(4) 0.6474(7) 0.5037(3) 0.0210(13) Uani d . . . 1 . .
C C7 0.2802(4) 0.5603(7) 0.5532(3) 0.0221(13) Uani d . . . 1 . .
C C8 0.3026(4) 0.5810(7) 0.6305(3) 0.0245(13) Uani d . . . 1 . .
C C9 0.3707(4) 0.7266(8) 0.6554(3) 0.0308(14) Uani d . . . 1 . .
H H9 0.3786 0.767 0.7059 0.037 Uiso calc U . R 1 . .
C C10 0.4242(4) 0.8079(7) 0.6081(3) 0.0274(14) Uani d . . . 1 . .
H H10 0.4705 0.8983 0.6273 0.033 Uiso calc U . R 1 . .
C C11 0.2696(4) 0.4318(8) 0.6717(3) 0.0286(14) Uani d . . . 1 . .
H H11 0.2734 0.4447 0.7242 0.034 Uiso calc U . R 1 . .
C C12 0.2331(4) 0.2722(8) 0.6380(3) 0.0325(14) Uani d . . . 1 . .
H H12 0.2152 0.1766 0.6681 0.039 Uiso calc U . R 1 . .
C C13 0.2213(4) 0.2457(7) 0.5580(3) 0.0253(13) Uani d . . . 1 . .
C C14 0.2383(3) 0.3984(7) 0.5178(3) 0.0215(13) Uani d . . . 1 . .
C C15 0.2629(4) 0.3884(7) 0.4453(3) 0.0221(13) Uani d . . . 1 . .
C C16 0.2685(3) 0.2259(7) 0.4080(3) 0.0200(12) Uani d . . . 1 . .
C C17 0.2374(3) 0.0691(7) 0.4442(3) 0.0245(13) Uani d . . . 1 . .
H H17 0.2315 -0.0444 0.4184 0.029 Uiso calc U . R 1 . .
C C18 0.2153(4) 0.0771(8) 0.5159(3) 0.0280(14) Uani d . . . 1 . .
H H18 0.1958 -0.0314 0.5377 0.034 Uiso calc U . R 1 . .
C C19 0.3183(3) 0.2383(7) 0.3437(3) 0.0212(12) Uani d . . . 1 . .
C C20 0.3719(4) 0.3991(7) 0.3319(3) 0.0212(12) Uani d . . . 1 . .
C C21 0.4140(3) 0.4071(7) 0.2647(3) 0.0240(13) Uani d . . . 1 . .
C C22 0.4564(3) 0.5693(7) 0.2418(3) 0.0241(13) Uani d . . . 1 . .
H H22 0.4536 0.6781 0.2699 0.029 Uiso calc U . R 1 . .
C C23 0.5015(4) 0.5742(7) 0.1800(3) 0.0246(13) Uani d . . . 1 . .
C C24 0.5324(4) 0.8094(8) 0.0667(3) 0.0422(17) Uani d . . . 1 . .
H H24A 0.5535 0.7048 0.0401 0.063 Uiso calc U . R 1 . .
H H24B 0.5633 0.9209 0.0528 0.063 Uiso calc U . R 1 . .
H H24C 0.4623 0.8221 0.0533 0.063 Uiso calc U . R 1 . .
C C25 0.4985(4) 0.4161(8) 0.1348(3) 0.0271(14) Uani d . . . 1 . .
H H25 0.5286 0.4174 0.0921 0.033 Uiso calc U . R 1 . .
C C26 0.4525(4) 0.2608(8) 0.1521(3) 0.0317(14) Uani d . . . 1 . .
H H26 0.4499 0.1572 0.1203 0.038 Uiso calc U . R 1 . .
C C27 0.4087(3) 0.2521(7) 0.2162(3) 0.0237(13) Uani d . . . 1 . .
C C28 0.3628(4) 0.0908(7) 0.2345(3) 0.0256(13) Uani d . . . 1 . .
H H28 0.363 -0.015 0.2043 0.031 Uiso calc U . R 1 . .
C C29 0.3183(4) 0.0854(7) 0.2947(3) 0.0242(13) Uani d . . . 1 . .
H H29 0.2862 -0.0234 0.3046 0.029 Uiso calc U . R 1 . .
S S1 0.56541(11) 0.7737(2) 0.16504(8) 0.0396(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.370(6) ?
C1 C6 . 1.423(7) ?
C1 C15 . 1.436(7) ?
C2 C3 . 1.447(7) ?
C2 C20 . 1.490(7) ?
C3 C4 . 1.397(7) ?
C4 C5 . 1.435(7) ?
C5 C6 . 1.385(7) ?
C5 C10 . 1.469(7) ?
C6 C7 . 1.411(7) ?
C7 C8 . 1.392(7) ?
C7 C14 . 1.425(7) ?
C8 C11 . 1.447(7) ?
C8 C9 . 1.451(7) ?
C9 C10 . 1.378(7) ?
C11 C12 . 1.376(7) ?
C12 C13 . 1.445(7) ?
C13 C14 . 1.381(7) ?
C13 C18 . 1.447(7) ?
C14 C15 . 1.423(7) ?
C15 C16 . 1.378(7) ?
C16 C17 . 1.430(6) ?
C16 C19 . 1.471(7) ?
C17 C18 . 1.394(7) ?
C19 C29 . 1.430(7) ?
C19 C20 . 1.436(7) ?
C20 C21 . 1.453(7) ?
C21 C22 . 1.425(7) ?
C21 C27 . 1.431(7) ?
C22 C23 . 1.387(7) ?
C23 C25 . 1.415(7) ?
C23 S1 . 1.764(5) ?
C24 S1 . 1.781(5) ?
C25 C26 . 1.373(7) ?
C26 C27 . 1.415(7) ?
C27 C28 . 1.415(7) ?
C28 C29 . 1.355(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 123.4(5) ?
C2 C1 C15 . . 123.2(5) ?
C6 C1 C15 . . 107.3(4) ?
C1 C2 C3 . . 114.1(4) ?
C1 C2 C20 . . 113.6(4) ?
C3 C2 C20 . . 131.1(5) ?
C4 C3 C2 . . 122.7(5) ?
C3 C4 C5 . . 121.8(5) ?
C6 C5 C4 . . 114.6(4) ?
C6 C5 C10 . . 114.6(4) ?
C4 C5 C10 . . 129.2(5) ?
C5 C6 C7 . . 122.5(5) ?
C5 C6 C1 . . 123.2(5) ?
C7 C6 C1 . . 108.8(5) ?
C8 C7 C6 . . 123.0(5) ?
C8 C7 C14 . . 123.1(5) ?
C6 C7 C14 . . 108.1(4) ?
C7 C8 C11 . . 113.9(5) ?
C7 C8 C9 . . 114.3(5) ?
C11 C8 C9 . . 130.5(5) ?
C10 C9 C8 . . 121.9(5) ?
C9 C10 C5 . . 121.4(5) ?
C12 C11 C8 . . 122.6(5) ?
C11 C12 C13 . . 121.9(5) ?
C14 C13 C12 . . 115.1(5) ?
C14 C13 C18 . . 114.1(5) ?
C12 C13 C18 . . 129.2(5) ?
C13 C14 C15 . . 122.9(5) ?
C13 C14 C7 . . 122.1(5) ?
C15 C14 C7 . . 108.0(4) ?
C16 C15 C14 . . 123.0(5) ?
C16 C15 C1 . . 123.1(5) ?
C14 C15 C1 . . 107.8(5) ?
C15 C16 C17 . . 114.6(4) ?
C15 C16 C19 . . 114.6(4) ?
C17 C16 C19 . . 130.2(5) ?
C18 C17 C16 . . 122.4(5) ?
C17 C18 C13 . . 121.9(5) ?
C29 C19 C20 . . 119.3(4) ?
C29 C19 C16 . . 120.0(5) ?
C20 C19 C16 . . 120.6(4) ?
C19 C20 C21 . . 117.7(4) ?
C19 C20 C2 . . 120.4(4) ?
C21 C20 C2 . . 121.9(4) ?
C22 C21 C27 . . 117.3(5) ?
C22 C21 C20 . . 122.4(5) ?
C27 C21 C20 . . 120.2(5) ?
C23 C22 C21 . . 122.4(5) ?
C22 C23 C25 . . 118.6(5) ?
C22 C23 S1 . . 118.0(4) ?
C25 C23 S1 . . 123.3(4) ?
C26 C25 C23 . . 120.7(5) ?
C25 C26 C27 . . 121.3(5) ?
C26 C27 C28 . . 121.2(5) ?
C26 C27 C21 . . 119.3(5) ?
C28 C27 C21 . . 119.4(4) ?
C29 C28 C27 . . 120.9(5) ?
C28 C29 C19 . . 122.1(5) ?
C23 S1 C24 . . 103.2(3) ?

####################################################################### 
# 
# 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_ms16
_database_code_depnum_ccdc_archive 'CCDC 1476774'
_audit_update_record             
;
2016-04-27 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_chemical_name_systematic        
N,N-dimethylacenaphtho[3,2,1,8-stuva]picen-8-amine
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H19 N'
_chemical_formula_iupac          ?
_chemical_formula_weight         393.46

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.3543(10)
_cell_length_b                   7.4826(4)
_cell_length_c                   17.7472(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.963(4)
_cell_angle_gamma                90
_cell_volume                     1887.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3582
_cell_measurement_theta_min      2.8657
_cell_measurement_theta_max      26.0486
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            39021
_diffrn_reflns_av_R_equivalents  0.1107
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             4136
_reflns_number_gt                2450
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.2127
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         4136
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1127P)²+0.4867P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 -0.0495(7) 0.2402(9) 0.3478(2) 0.0409(18) Uani d . P . 0.90(3) A 1
N N1A -0.003(5) 0.296(6) 0.3555(15) 0.032(12) Uani d . P . 0.10(3) A 2
C C1 0.18281(19) -0.2327(3) 0.15701(15) 0.0300(6) Uani d . . . 1.0 . .
C C2 0.12878(18) -0.0782(3) 0.17060(14) 0.0290(6) Uani d . . . 1.0 . .
C C3 0.11320(19) 0.0623(3) 0.11144(14) 0.0286(6) Uani d . . . 1.0 . .
C C4 0.0339(2) 0.1790(3) 0.09036(15) 0.0324(6) Uani d . . . 1.0 . .
H H4 -0.0098 0.1926 0.124 0.039 Uiso calc U . R 1.0 . .
C C5 0.0200(2) 0.2715(3) 0.02230(15) 0.0328(6) Uani d . . . 1.0 . .
H H5 -0.0322 0.3459 0.0124 0.039 Uiso calc U . R 1.0 . .
C C6 0.08244(19) 0.2574(3) -0.03354(15) 0.0321(7) Uani d . . . 1.0 . .
C C7 0.0670(2) 0.2975(4) -0.11395(16) 0.0360(7) Uani d . . . 1.0 . .
H H7 0.0228 0.3838 -0.1318 0.043 Uiso calc U . R 1.0 . .
C C8 0.1157(2) 0.2123(4) -0.16484(16) 0.0374(7) Uani d . . . 1.0 . .
H H8 0.104 0.2434 -0.216 0.045 Uiso calc U . R 1.0 . .
C C9 0.1842(2) 0.0762(4) -0.14111(16) 0.0351(7) Uani d . . . 1.0 . .
C C10 0.2148(2) -0.0717(4) -0.18339(17) 0.0399(7) Uani d . . . 1.0 . .
H H10 0.2072 -0.0649 -0.2362 0.048 Uiso calc U . R 1.0 . .
C C11 0.2548(2) -0.2229(4) -0.14844(17) 0.0411(7) Uani d . . . 1.0 . .
H H11 0.273 -0.3152 -0.1783 0.049 Uiso calc U . R 1.0 . .
C C12 0.2694(2) -0.2419(4) -0.06691(17) 0.0355(7) Uani d . . . 1.0 . .
C C13 0.2773(2) -0.4030(4) -0.02191(17) 0.0387(7) Uani d . . . 1.0 . .
H H13 0.2957 -0.5084 -0.0434 0.046 Uiso calc U . R 1.0 . .
C C14 0.2584(2) -0.4049(4) 0.05215(16) 0.0368(7) Uani d . . . 1.0 . .
H H14 0.2648 -0.5116 0.0793 0.044 Uiso calc U . R 1.0 . .
C C15 0.22908(19) -0.2473(3) 0.08888(15) 0.0311(6) Uani d . . . 1.0 . .
C C16 0.23246(19) -0.0918(3) 0.04834(15) 0.0303(6) Uani d . . . 1.0 . .
C C17 0.17481(19) 0.0588(3) 0.05891(14) 0.0287(6) Uani d . . . 1.0 . .
C C18 0.16109(19) 0.1528(3) -0.01061(15) 0.0301(6) Uani d . . . 1.0 . .
C C19 0.21028(19) 0.0642(3) -0.06347(15) 0.0320(6) Uani d . . . 1.0 . .
C C20 0.25294(19) -0.0888(3) -0.02730(15) 0.0322(6) Uani d . . . 1.0 . .
C C21 0.1907(2) -0.3753(4) 0.20992(16) 0.0346(7) Uani d . . . 1.0 . .
H H21 0.224 -0.4772 0.2 0.042 Uiso calc U . R 1.0 . .
C C22 0.1510(2) -0.3670(4) 0.27451(15) 0.0356(7) Uani d . . . 1.0 . .
H H22 0.1571 -0.4633 0.3079 0.043 Uiso calc U . R 1.0 . .
C C23 0.1005(2) -0.2147(3) 0.29202(15) 0.0332(6) Uani d . . . 1.0 . .
C C24 0.0590(2) -0.2043(4) 0.35953(16) 0.0395(7) Uani d . . . 1.0 . .
H H24 0.0652 -0.3004 0.3931 0.047 Uiso calc U . R 1.0 . .
C C25 0.0101(2) -0.0578(4) 0.37693(16) 0.0412(7) Uani d . . . 1.0 . .
H H25 -0.0193 -0.0576 0.4205 0.049 Uiso calc U . R 1.0 . .
C C26 0.0037(2) 0.0945(4) 0.32911(16) 0.0390(7) Uani d . . . 1.0 . .
C C27 0.0456(2) 0.0879(4) 0.26376(15) 0.0345(7) Uani d . . . 1.0 . .
H H27 0.0443 0.1895 0.2334 0.041 Uiso calc U . R 1.0 . .
C C28 0.09034(19) -0.0676(3) 0.24118(15) 0.0312(6) Uani d . . . 1.0 . .
C C29 -0.0598(2) 0.3885(4) 0.29456(18) 0.0463(8) Uani d . . . 1.0 . .
H H29A 0.0005 0.4422 0.2925 0.069 Uiso calc U . R 1.0 A 1
H H29B -0.1017 0.4757 0.311 0.069 Uiso calc U . R 1.0 A 1
H H29C -0.085 0.3456 0.2449 0.069 Uiso calc U . R 1.0 A 1
C C30 -0.0366(3) 0.2976(5) 0.42711(18) 0.0543(9) Uani d . . . 1.0 . .
H H30A -0.05 0.1997 0.4589 0.081 Uiso calc U . R 1.0 A 1
H H30B -0.0786 0.3949 0.4331 0.081 Uiso calc U . R 1.0 A 1
H H30C 0.0272 0.3361 0.4415 0.081 Uiso calc U . R 1.0 A 1


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C26 . 1.397(4) ?
N1 C29 . 1.451(5) ?
N1 C30 . 1.459(6) ?
N1A C30 . 1.42(3) ?
N1A C29 . 1.44(3) ?
N1A C26 . 1.59(4) ?
C1 C21 . 1.416(4) ?
C1 C2 . 1.431(4) ?
C1 C15 . 1.462(4) ?
C2 C28 . 1.439(4) ?
C2 C3 . 1.481(3) ?
C3 C17 . 1.371(4) ?
C3 C4 . 1.442(4) ?
C4 C5 . 1.382(4) ?
C5 C6 . 1.430(4) ?
C6 C18 . 1.387(4) ?
C6 C7 . 1.445(4) ?
C7 C8 . 1.373(4) ?
C8 C9 . 1.438(4) ?
C9 C19 . 1.380(4) ?
C9 C10 . 1.439(4) ?
C10 C11 . 1.377(4) ?
C11 C12 . 1.440(4) ?
C12 C20 . 1.382(4) ?
C12 C13 . 1.441(4) ?
C13 C14 . 1.379(4) ?
C14 C15 . 1.438(4) ?
C15 C16 . 1.372(4) ?
C16 C20 . 1.413(4) ?
C16 C17 . 1.426(4) ?
C17 C18 . 1.410(4) ?
C18 C19 . 1.415(4) ?
C19 C20 . 1.410(4) ?
C21 C22 . 1.350(4) ?
C22 C23 . 1.408(4) ?
C23 C24 . 1.412(4) ?
C23 C28 . 1.418(4) ?
C24 C25 . 1.360(4) ?
C25 C26 . 1.416(4) ?
C26 C27 . 1.379(4) ?
C27 C28 . 1.414(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C26 N1 C29 . . 116.9(3) ?
C26 N1 C30 . . 117.3(4) ?
C29 N1 C30 . . 113.0(5) ?
C30 N1A C29 . . 116.(3) ?
C30 N1A C26 . . 108.(3) ?
C29 N1A C26 . . 107.(3) ?
C21 C1 C2 . . 119.5(3) ?
C21 C1 C15 . . 119.3(2) ?
C2 C1 C15 . . 121.2(2) ?
C1 C2 C28 . . 118.3(2) ?
C1 C2 C3 . . 119.1(2) ?
C28 C2 C3 . . 122.6(2) ?
C17 C3 C4 . . 113.3(2) ?
C17 C3 C2 . . 114.8(2) ?
C4 C3 C2 . . 130.5(3) ?
C5 C4 C3 . . 122.9(3) ?
C4 C5 C6 . . 122.7(3) ?
C18 C6 C5 . . 113.7(2) ?
C18 C6 C7 . . 114.4(2) ?
C5 C6 C7 . . 130.1(3) ?
C8 C7 C6 . . 122.1(3) ?
C7 C8 C9 . . 121.7(3) ?
C19 C9 C8 . . 114.7(3) ?
C19 C9 C10 . . 114.2(3) ?
C8 C9 C10 . . 129.6(3) ?
C11 C10 C9 . . 122.4(3) ?
C10 C11 C12 . . 121.8(3) ?
C20 C12 C11 . . 114.7(3) ?
C20 C12 C13 . . 114.7(3) ?
C11 C12 C13 . . 129.0(3) ?
C14 C13 C12 . . 121.7(2) ?
C13 C14 C15 . . 122.2(2) ?
C16 C15 C14 . . 115.1(2) ?
C16 C15 C1 . . 115.1(2) ?
C14 C15 C1 . . 129.1(2) ?
C15 C16 C20 . . 122.6(2) ?
C15 C16 C17 . . 122.5(2) ?
C20 C16 C17 . . 108.3(2) ?
C3 C17 C18 . . 124.1(2) ?
C3 C17 C16 . . 123.1(2) ?
C18 C17 C16 . . 107.0(2) ?
C6 C18 C17 . . 123.2(3) ?
C6 C18 C19 . . 122.0(2) ?
C17 C18 C19 . . 108.9(2) ?
C9 C19 C20 . . 123.2(3) ?
C9 C19 C18 . . 122.7(3) ?
C20 C19 C18 . . 107.7(2) ?
C12 C20 C19 . . 122.4(3) ?
C12 C20 C16 . . 122.9(2) ?
C19 C20 C16 . . 108.1(2) ?
C22 C21 C1 . . 121.6(3) ?
C21 C22 C23 . . 121.0(2) ?
C22 C23 C24 . . 121.5(2) ?
C22 C23 C28 . . 119.9(2) ?
C24 C23 C28 . . 118.6(2) ?
C25 C24 C23 . . 121.9(3) ?
C24 C25 C26 . . 120.3(3) ?
C27 C26 N1 . . 122.9(3) ?
C27 C26 C25 . . 118.4(3) ?
N1 C26 C25 . . 118.5(3) ?
C27 C26 N1A . . 109.5(16) ?
C25 C26 N1A . . 126.2(10) ?
C26 C27 C28 . . 122.4(3) ?
C27 C28 C23 . . 118.0(2) ?
C27 C28 C2 . . 122.5(2) ?
C23 C28 C2 . . 119.5(2) ?

