# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_20171225nlg_0m_a_sq
_audit_block_doi                 10.5517/ccdc.csd.cc21c890
_database_code_depnum_ccdc_archive 'CCDC 1887661'
loop_
_audit_author_name
_audit_author_address
Tetrahydro-epoxyhexacene
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2019-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        5,6,15,16-Tetrahydro-5,16-epoxyhexacene
_chemical_name_common            ?
_chemical_melting_point          275-277
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 O'
_chemical_formula_weight         346.40

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           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                   42.263(3)
_cell_length_b                   7.4986(7)
_cell_length_c                   12.0012(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.813(3)
_cell_angle_gamma                90
_cell_volume                     3794.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3795
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      28.24
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10901
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.759
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3339
_reflns_number_gt                2536
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0864P)²+12.1273P] 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         3339
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.82390(7) 0.5026(4) 0.4815(2) 0.0184(6) Uani 1 1 d . . . . .
H1 H 0.820805 0.569450 0.416463 0.022 Uiso 1 1 calc R U . . .
C2 C 0.85382(7) 0.4514(4) 0.5170(2) 0.0209(6) Uani 1 1 d . . . . .
H2 H 0.870907 0.484448 0.476544 0.025 Uiso 1 1 calc R U . . .
C3 C 0.85901(7) 0.3476(4) 0.6158(2) 0.0207(6) Uani 1 1 d . . . . .
H3 H 0.879524 0.313979 0.639865 0.025 Uiso 1 1 calc R U . . .
C4 C 0.83419(6) 0.2971(4) 0.6755(2) 0.0185(6) Uani 1 1 d . . . . .
H4 H 0.837954 0.227944 0.739379 0.022 Uiso 1 1 calc R U . . .
C5 C 0.80246(6) 0.3488(4) 0.6414(2) 0.0148(6) Uani 1 1 d . . . . .
C6 C 0.77655(6) 0.2980(4) 0.7003(2) 0.0155(6) Uani 1 1 d . . . . .
H6 H 0.779925 0.227953 0.763978 0.019 Uiso 1 1 calc R U . . .
C7 C 0.74571(6) 0.3496(4) 0.6661(2) 0.0130(6) Uani 1 1 d . . . . .
C8 C 0.71897(6) 0.2977(4) 0.7241(2) 0.0143(6) Uani 1 1 d . . . . .
H8 H 0.722155 0.226795 0.787445 0.017 Uiso 1 1 calc R U . . .
C9 C 0.68872(6) 0.3479(4) 0.6904(2) 0.0141(6) Uani 1 1 d . . . . .
C10 C 0.66165(6) 0.2792(4) 0.7553(2) 0.0172(6) Uani 1 1 d . . . . .
H10A H 0.659847 0.151163 0.745415 0.021 Uiso 1 1 calc R U . . .
H10B H 0.666295 0.302622 0.834185 0.021 Uiso 1 1 calc R U . . .
C11 C 0.63099(6) 0.3644(4) 0.7184(2) 0.0192(6) Uani 1 1 d . . . . .
C12 C 0.59807(7) 0.3298(4) 0.7608(3) 0.0227(7) Uani 1 1 d . . . . .
H12 H 0.597649 0.290803 0.838627 0.027 Uiso 1 1 calc R U . . .
C13 C 0.58022(6) 0.2110(4) 0.6730(2) 0.0195(6) Uani 1 1 d . . . . .
C14 C 0.56950(7) 0.0389(4) 0.6722(3) 0.0234(7) Uani 1 1 d . . . . .
H14 H 0.572727 -0.034101 0.734583 0.028 Uiso 1 1 calc R U . . .
C15 C 0.55334(7) -0.0235(4) 0.5732(3) 0.0256(7) Uani 1 1 d . . . . .
H15 H 0.545337 -0.139070 0.570538 0.031 Uiso 1 1 calc R U . . .
C16 C 0.54926(7) 0.0846(4) 0.4803(3) 0.0254(7) Uani 1 1 d . . . . .
H16 H 0.538820 0.040084 0.415559 0.030 Uiso 1 1 calc R U . . .
C17 C 0.56059(6) 0.2607(4) 0.4818(3) 0.0227(7) Uani 1 1 d . . . . .
H17 H 0.557964 0.333492 0.419152 0.027 Uiso 1 1 calc R U . . .
C18 C 0.57567(6) 0.3214(4) 0.5793(2) 0.0195(6) Uani 1 1 d . . . . .
C19 C 0.59032(7) 0.4992(4) 0.6163(3) 0.0223(7) Uani 1 1 d . . . . .
H19 H 0.583311 0.603469 0.572091 0.027 Uiso 1 1 calc R U . . .
C20 C 0.62621(6) 0.4691(4) 0.6301(2) 0.0175(6) Uani 1 1 d . . . . .
C21 C 0.65046(6) 0.5233(4) 0.5527(2) 0.0163(6) Uani 1 1 d . . . . .
H21A H 0.650564 0.652285 0.546181 0.020 Uiso 1 1 calc R U . . .
H21B H 0.644931 0.474169 0.479185 0.020 Uiso 1 1 calc R U . . .
C22 C 0.68348(6) 0.4594(4) 0.5931(2) 0.0134(6) Uani 1 1 d . . . . .
C23 C 0.70879(6) 0.5103(3) 0.5357(2) 0.0139(6) Uani 1 1 d . . . . .
H23 H 0.705169 0.581845 0.472817 0.017 Uiso 1 1 calc R U . . .
C24 C 0.74048(6) 0.4585(4) 0.5679(2) 0.0132(6) Uani 1 1 d . . . . .
C25 C 0.76636(7) 0.5074(4) 0.5081(2) 0.0154(6) Uani 1 1 d . . . . .
H25 H 0.762928 0.576160 0.443916 0.018 Uiso 1 1 calc R U . . .
C26 C 0.79727(6) 0.4557(4) 0.5422(2) 0.0145(6) Uani 1 1 d . . . . .
O1 O 0.58279(5) 0.5006(3) 0.73323(18) 0.0282(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.362(4) . ?
C1 C26 1.424(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.423(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.429(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(4) . ?
C5 C26 1.441(4) . ?
C6 C7 1.395(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.420(4) . ?
C7 C24 1.439(4) . ?
C8 C9 1.368(4) . ?
C8 H8 0.9300 . ?
C9 C22 1.441(4) . ?
C9 C10 1.516(4) . ?
C10 C11 1.485(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C20 1.323(4) . ?
C11 C12 1.535(4) . ?
C12 O1 1.463(4) . ?
C12 C13 1.538(4) . ?
C12 H12 0.9800 . ?
C13 C14 1.367(4) . ?
C13 C18 1.399(4) . ?
C14 C15 1.410(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.404(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.524(4) . ?
C19 O1 1.459(4) . ?
C19 C20 1.531(4) . ?
C19 H19 0.9800 . ?
C20 C21 1.486(4) . ?
C21 C22 1.524(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.365(4) . ?
C23 C24 1.423(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.397(4) . ?
C25 C26 1.398(4) . ?
C25 H25 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 C26 121.3(3) . . ?
C2 C1 H1 119.3 . . ?
C26 C1 H1 119.3 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 122.3(3) . . ?
C6 C5 C26 119.3(2) . . ?
C4 C5 C26 118.4(2) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 122.5(2) . . ?
C6 C7 C24 119.2(2) . . ?
C8 C7 C24 118.2(2) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C22 119.3(2) . . ?
C8 C9 C10 118.5(2) . . ?
C22 C9 C10 122.2(2) . . ?
C11 C10 C9 112.0(2) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C20 C11 C10 125.3(3) . . ?
C20 C11 C12 105.8(2) . . ?
C10 C11 C12 128.3(3) . . ?
O1 C12 C11 100.0(2) . . ?
O1 C12 C13 99.4(2) . . ?
C11 C12 C13 106.6(2) . . ?
O1 C12 H12 116.2 . . ?
C11 C12 H12 116.2 . . ?
C13 C12 H12 116.2 . . ?
C14 C13 C18 121.7(3) . . ?
C14 C13 C12 134.3(3) . . ?
C18 C13 C12 104.0(3) . . ?
C13 C14 C15 117.4(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 C19 134.0(3) . . ?
C13 C18 C19 104.6(3) . . ?
O1 C19 C18 100.1(2) . . ?
O1 C19 C20 100.1(2) . . ?
C18 C19 C20 106.4(2) . . ?
O1 C19 H19 116.0 . . ?
C18 C19 H19 116.0 . . ?
C20 C19 H19 116.0 . . ?
C11 C20 C21 126.0(3) . . ?
C11 C20 C19 105.8(2) . . ?
C21 C20 C19 127.7(3) . . ?
C20 C21 C22 111.7(2) . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C9 119.2(2) . . ?
C23 C22 C21 118.9(2) . . ?
C9 C22 C21 121.9(2) . . ?
C22 C23 C24 122.8(2) . . ?
C22 C23 H23 118.6 . . ?
C24 C23 H23 118.6 . . ?
C25 C24 C23 122.9(3) . . ?
C25 C24 C7 119.2(2) . . ?
C23 C24 C7 117.9(2) . . ?
C24 C25 C26 121.7(3) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C25 C26 C1 122.5(3) . . ?
C25 C26 C5 119.0(2) . . ?
C1 C26 C5 118.5(2) . . ?
C19 O1 C12 95.2(2) . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.067



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
