# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_psu-735(fa999)
_database_code_depnum_ccdc_archive 'CCDC 2117819'
loop_
_audit_author_name
_audit_author_address
'Aleksandr Rubtsov'
;Perm State University
Russia
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
2-phenyl-2,3,4,5-tetrahydro-2,5-epoxybenzo[b]oxepine
_chemical_formula_moiety         'C16 H14 O2'
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27
_chemical_melting_point          379
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   9.970(3)
_cell_length_b                   21.704(5)
_cell_length_c                   11.259(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.57(2)
_cell_angle_gamma                90
_cell_volume                     2436.1(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1566
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.1220
_cell_measurement_theta_min      3.3140
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11345
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.482
_diffrn_reflns_theta_min         2.873
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   13.00   43.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  -77.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -61.00   53.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  -19.0000   60.0000 114

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   25.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3197  -99.0000 -150.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0613441000
_diffrn_orient_matrix_UB_12      -0.0165651000
_diffrn_orient_matrix_UB_13      0.0026268000
_diffrn_orient_matrix_UB_21      0.0357874000
_diffrn_orient_matrix_UB_22      -0.0282137000
_diffrn_orient_matrix_UB_23      -0.0020460000
_diffrn_orient_matrix_UB_31      0.0045756000
_diffrn_orient_matrix_UB_32      -0.0002657000
_diffrn_orient_matrix_UB_33      0.0628569000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2449
_reflns_number_total             5626
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0056(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.2061
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C2A(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C3A(H3AA,H3AB), C4A(H4AA,H4AB)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C12A(H12A), C13A(H13A),
 C14A(H14A), C15A(H15A), C16A(H16A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.2172(3) 0.22831(13) 0.4562(2) 0.0407(7) Uani 1 1 d . . . . .
O1 O 0.12609(19) 0.25094(9) 0.54063(15) 0.0433(5) Uani 1 1 d . . . . .
C2 C 0.1842(3) 0.30991(14) 0.5752(2) 0.0451(8) Uani 1 1 d . . . . .
H2 H 0.142968 0.326180 0.647314 0.054 Uiso 1 1 calc R U . . .
O2 O 0.2003(2) 0.26419(9) 0.34694(14) 0.0475(6) Uani 1 1 d . . . . .
C3 C 0.3326(3) 0.29426(14) 0.5955(2) 0.0514(8) Uani 1 1 d . . . . .
H3A H 0.349381 0.281825 0.677010 0.062 Uiso 1 1 calc R U . . .
H3B H 0.389447 0.329151 0.576820 0.062 Uiso 1 1 calc R U . . .
C4 C 0.3567(3) 0.24068(14) 0.5095(2) 0.0481(8) Uani 1 1 d . . . . .
H4A H 0.390639 0.204744 0.551298 0.058 Uiso 1 1 calc R U . . .
H4B H 0.419860 0.252193 0.448345 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1763(3) 0.32644(13) 0.3608(2) 0.0393(7) Uani 1 1 d . . . . .
C6 C 0.1654(3) 0.35253(14) 0.4725(2) 0.0429(7) Uani 1 1 d . . . . .
C7 C 0.1401(3) 0.41540(14) 0.4799(3) 0.0527(8) Uani 1 1 d . . . . .
H7 H 0.131752 0.433548 0.554305 0.063 Uiso 1 1 calc R U . . .
C8 C 0.1271(3) 0.45143(15) 0.3798(3) 0.0586(9) Uani 1 1 d . . . . .
H8 H 0.110740 0.493473 0.386420 0.070 Uiso 1 1 calc R U . . .
C9 C 0.1385(3) 0.42430(15) 0.2698(3) 0.0576(9) Uani 1 1 d . . . . .
H9 H 0.130901 0.448330 0.201720 0.069 Uiso 1 1 calc R U . . .
C10 C 0.1613(3) 0.36158(14) 0.2597(2) 0.0499(8) Uani 1 1 d . . . . .
H10 H 0.166421 0.343338 0.185133 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1831(3) 0.16325(13) 0.4224(2) 0.0403(7) Uani 1 1 d . . . . .
C12 C 0.0527(3) 0.14098(16) 0.4330(3) 0.0575(9) Uani 1 1 d . . . . .
H12 H -0.013993 0.166105 0.463811 0.069 Uiso 1 1 calc R U . . .
C13 C 0.0225(4) 0.08144(17) 0.3976(3) 0.0736(11) Uani 1 1 d . . . . .
H13 H -0.064537 0.066586 0.405112 0.088 Uiso 1 1 calc R U . . .
C14 C 0.1209(4) 0.04412(17) 0.3514(3) 0.0700(11) Uani 1 1 d . . . . .
H14 H 0.100033 0.004183 0.327624 0.084 Uiso 1 1 calc R U . . .
C15 C 0.2491(4) 0.06568(16) 0.3404(3) 0.0645(10) Uani 1 1 d . . . . .
H15 H 0.315281 0.040400 0.309059 0.077 Uiso 1 1 calc R U . . .
C16 C 0.2806(3) 0.12509(14) 0.3758(3) 0.0521(8) Uani 1 1 d . . . . .
H16 H 0.367952 0.139482 0.368262 0.063 Uiso 1 1 calc R U . . .
C1A C 0.7190(3) 0.26633(13) 0.2783(2) 0.0410(7) Uani 1 1 d . . . . .
O1A O 0.62756(19) 0.24377(9) 0.19312(15) 0.0464(6) Uani 1 1 d . . . . .
C2A C 0.6858(3) 0.18509(14) 0.1599(2) 0.0480(8) Uani 1 1 d . . . . .
H2A H 0.643729 0.168820 0.087402 0.058 Uiso 1 1 calc R U . . .
O2A O 0.7001(2) 0.23136(9) 0.38790(14) 0.0485(6) Uani 1 1 d . . . . .
C3A C 0.8333(3) 0.20053(15) 0.1401(2) 0.0532(9) Uani 1 1 d . . . . .
H3AA H 0.848668 0.213275 0.058778 0.064 Uiso 1 1 calc R U . . .
H3AB H 0.890509 0.165632 0.158688 0.064 Uiso 1 1 calc R U . . .
C4A C 0.8575(3) 0.25369(14) 0.2268(3) 0.0531(9) Uani 1 1 d . . . . .
H4AA H 0.920783 0.241904 0.288803 0.064 Uiso 1 1 calc R U . . .
H4AB H 0.891636 0.289670 0.185935 0.064 Uiso 1 1 calc R U . . .
C5A C 0.6758(3) 0.16900(13) 0.3746(2) 0.0434(7) Uani 1 1 d . . . . .
C6A C 0.6662(3) 0.14212(15) 0.2630(2) 0.0465(8) Uani 1 1 d . . . . .
C7A C 0.6413(3) 0.07928(16) 0.2562(3) 0.0632(10) Uani 1 1 d . . . . .
H7A H 0.634951 0.060432 0.182185 0.076 Uiso 1 1 calc R U . . .
C8A C 0.6257(3) 0.04450(17) 0.3570(4) 0.0713(11) Uani 1 1 d . . . . .
H8A H 0.609349 0.002426 0.350975 0.086 Uiso 1 1 calc R U . . .
C9A C 0.6343(4) 0.07185(16) 0.4666(3) 0.0681(10) Uani 1 1 d . . . . .
H9A H 0.624000 0.048275 0.534897 0.082 Uiso 1 1 calc R U . . .
C10A C 0.6582(3) 0.13436(15) 0.4758(3) 0.0558(9) Uani 1 1 d . . . . .
H10A H 0.662316 0.153023 0.550048 0.067 Uiso 1 1 calc R U . . .
C11A C 0.6842(3) 0.33111(14) 0.3114(2) 0.0411(7) Uani 1 1 d . . . . .
C12A C 0.5521(3) 0.35158(15) 0.3103(3) 0.0544(8) Uani 1 1 d . . . . .
H12A H 0.484464 0.325370 0.283472 0.065 Uiso 1 1 calc R U . . .
C13A C 0.5190(4) 0.41065(16) 0.3487(3) 0.0638(10) Uani 1 1 d . . . . .
H13A H 0.429999 0.423451 0.347720 0.077 Uiso 1 1 calc R U . . .
C14A C 0.6180(4) 0.45006(16) 0.3880(3) 0.0655(10) Uani 1 1 d . . . . .
H14A H 0.596700 0.489592 0.413537 0.079 Uiso 1 1 calc R U . . .
C15A C 0.7492(4) 0.43003(16) 0.3891(3) 0.0658(10) Uani 1 1 d . . . . .
H15A H 0.816668 0.456324 0.415829 0.079 Uiso 1 1 calc R U . . .
C16A C 0.7820(3) 0.37130(15) 0.3509(3) 0.0559(9) Uani 1 1 d . . . . .
H16A H 0.871230 0.358824 0.351884 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.410(3) . ?
C1 O2 1.464(3) . ?
C1 C4 1.533(4) . ?
C1 C11 1.500(4) . ?
O1 C2 1.456(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.533(4) . ?
C2 C6 1.491(4) . ?
O2 C5 1.381(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.534(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.384(3) . ?
C5 C10 1.377(4) . ?
C6 C7 1.390(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(4) . ?
C11 C16 1.384(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9300 . ?
C1A O1A 1.405(3) . ?
C1A O2A 1.462(3) . ?
C1A C4A 1.528(4) . ?
C1A C11A 1.496(4) . ?
O1A C2A 1.450(3) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.527(4) . ?
C2A C6A 1.503(4) . ?
O2A C5A 1.383(3) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A C4A 1.529(4) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C5A C6A 1.387(4) . ?
C5A C10A 1.378(4) . ?
C6A C7A 1.388(4) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.373(4) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.371(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.381(4) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.391(4) . ?
C11A C16A 1.378(4) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.394(4) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.376(4) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.378(4) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.386(4) . ?
C16A H16A 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
O1 C1 O2 108.2(2) . . ?
O1 C1 C4 105.2(2) . . ?
O1 C1 C11 110.6(2) . . ?
O2 C1 C4 109.4(2) . . ?
O2 C1 C11 105.3(2) . . ?
C11 C1 C4 117.8(2) . . ?
C1 O1 C2 103.2(2) . . ?
O1 C2 H2 111.6 . . ?
O1 C2 C3 103.1(2) . . ?
O1 C2 C6 106.9(2) . . ?
C3 C2 H2 111.6 . . ?
C6 C2 H2 111.6 . . ?
C6 C2 C3 111.5(2) . . ?
C5 O2 C1 116.37(19) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C2 C3 C4 103.4(2) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C1 C4 H4A 111.1 . . ?
C1 C4 H4B 111.1 . . ?
C3 C4 C1 103.4(2) . . ?
C3 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
O2 C5 C6 121.2(2) . . ?
C10 C5 O2 117.8(2) . . ?
C10 C5 C6 121.0(3) . . ?
C5 C6 C2 116.1(3) . . ?
C5 C6 C7 118.2(3) . . ?
C7 C6 C2 125.7(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 C9 119.5(3) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C1 121.0(3) . . ?
C16 C11 C1 120.0(3) . . ?
C16 C11 C12 119.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(3) . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.6(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O1A C1A O2A 107.9(2) . . ?
O1A C1A C4A 105.1(2) . . ?
O1A C1A C11A 110.3(2) . . ?
O2A C1A C4A 110.6(2) . . ?
O2A C1A C11A 104.2(2) . . ?
C11A C1A C4A 118.4(2) . . ?
C1A O1A C2A 102.9(2) . . ?
O1A C2A H2A 111.2 . . ?
O1A C2A C3A 103.5(2) . . ?
O1A C2A C6A 106.9(2) . . ?
C3A C2A H2A 111.2 . . ?
C6A C2A H2A 111.2 . . ?
C6A C2A C3A 112.4(2) . . ?
C5A O2A C1A 116.1(2) . . ?
C2A C3A H3AA 111.2 . . ?
C2A C3A H3AB 111.2 . . ?
C2A C3A C4A 102.6(2) . . ?
H3AA C3A H3AB 109.2 . . ?
C4A C3A H3AA 111.2 . . ?
C4A C3A H3AB 111.2 . . ?
C1A C4A C3A 103.9(2) . . ?
C1A C4A H4AA 111.0 . . ?
C1A C4A H4AB 111.0 . . ?
C3A C4A H4AA 111.0 . . ?
C3A C4A H4AB 111.0 . . ?
H4AA C4A H4AB 109.0 . . ?
O2A C5A C6A 121.4(3) . . ?
C10A C5A O2A 117.9(2) . . ?
C10A C5A C6A 120.7(3) . . ?
C5A C6A C2A 115.5(3) . . ?
C5A C6A C7A 118.3(3) . . ?
C7A C6A C2A 126.3(3) . . ?
C6A C7A H7A 119.5 . . ?
C8A C7A C6A 121.1(3) . . ?
C8A C7A H7A 119.5 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A C7A 120.0(3) . . ?
C9A C8A H8A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C8A C9A C10A 120.1(3) . . ?
C10A C9A H9A 120.0 . . ?
C5A C10A C9A 119.9(3) . . ?
C5A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C12A C11A C1A 121.3(3) . . ?
C16A C11A C1A 120.7(3) . . ?
C16A C11A C12A 117.9(3) . . ?
C11A C12A H12A 119.4 . . ?
C11A C12A C13A 121.2(3) . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 120.1(3) . . ?
C14A C13A H13A 120.0 . . ?
C13A C14A H14A 120.5 . . ?
C13A C14A C15A 119.0(3) . . ?
C15A C14A H14A 120.5 . . ?
C14A C15A H15A 119.5 . . ?
C14A C15A C16A 121.0(3) . . ?
C16A C15A H15A 119.5 . . ?
C11A C16A C15A 120.9(3) . . ?
C11A C16A H16A 119.5 . . ?
C15A C16A H16A 119.5 . . ?

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
C1 O1 C2 C3 -46.3(2) . . . . ?
C1 O1 C2 C6 71.4(3) . . . . ?
C1 O2 C5 C6 -1.7(4) . . . . ?
C1 O2 C5 C10 179.4(2) . . . . ?
C1 C11 C12 C13 177.8(3) . . . . ?
C1 C11 C16 C15 -177.6(3) . . . . ?
O1 C1 O2 C5 38.2(3) . . . . ?
O1 C1 C4 C3 -24.0(3) . . . . ?
O1 C1 C11 C12 25.2(3) . . . . ?
O1 C1 C11 C16 -157.3(2) . . . . ?
O1 C2 C3 C4 29.8(3) . . . . ?
O1 C2 C6 C5 -35.9(3) . . . . ?
O1 C2 C6 C7 145.0(3) . . . . ?
C2 C3 C4 C1 -4.1(3) . . . . ?
C2 C6 C7 C8 178.5(3) . . . . ?
O2 C1 O1 C2 -72.9(2) . . . . ?
O2 C1 C4 C3 92.0(2) . . . . ?
O2 C1 C11 C12 -91.4(3) . . . . ?
O2 C1 C11 C16 86.1(3) . . . . ?
O2 C5 C6 C2 1.4(4) . . . . ?
O2 C5 C6 C7 -179.5(3) . . . . ?
O2 C5 C10 C9 -179.3(3) . . . . ?
C3 C2 C6 C5 76.0(3) . . . . ?
C3 C2 C6 C7 -103.0(3) . . . . ?
C4 C1 O1 C2 44.0(3) . . . . ?
C4 C1 O2 C5 -75.9(3) . . . . ?
C4 C1 C11 C12 146.3(3) . . . . ?
C4 C1 C11 C16 -36.2(4) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C6 C2 C3 C4 -84.6(3) . . . . ?
C6 C5 C10 C9 1.8(4) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C8 C9 C10 C5 -1.8(5) . . . . ?
C10 C5 C6 C2 -179.7(3) . . . . ?
C10 C5 C6 C7 -0.6(4) . . . . ?
C11 C1 O1 C2 172.2(2) . . . . ?
C11 C1 O2 C5 156.5(2) . . . . ?
C11 C1 C4 C3 -147.8(2) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C11 C16 C15 -0.1(4) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C11 -0.1(5) . . . . ?
C16 C11 C12 C13 0.3(4) . . . . ?
C1A O1A C2A C3A -46.9(2) . . . . ?
C1A O1A C2A C6A 72.0(3) . . . . ?
C1A O2A C5A C6A -1.8(4) . . . . ?
C1A O2A C5A C10A 179.7(2) . . . . ?
C1A C11A C12A C13A 175.7(3) . . . . ?
C1A C11A C16A C15A -175.7(3) . . . . ?
O1A C1A O2A C5A 39.2(3) . . . . ?
O1A C1A C4A C3A -23.5(3) . . . . ?
O1A C1A C11A C12A 31.4(3) . . . . ?
O1A C1A C11A C16A -152.5(2) . . . . ?
O1A C2A C3A C4A 30.6(3) . . . . ?
O1A C2A C6A C5A -35.5(3) . . . . ?
O1A C2A C6A C7A 145.1(3) . . . . ?
C2A C3A C4A C1A -4.8(3) . . . . ?
C2A C6A C7A C8A 179.7(3) . . . . ?
O2A C1A O1A C2A -74.3(2) . . . . ?
O2A C1A C4A C3A 92.6(3) . . . . ?
O2A C1A C11A C12A -84.1(3) . . . . ?
O2A C1A C11A C16A 91.9(3) . . . . ?
O2A C5A C6A C2A 0.8(4) . . . . ?
O2A C5A C6A C7A -179.8(3) . . . . ?
O2A C5A C10A C9A -179.7(3) . . . . ?
C3A C2A C6A C5A 77.4(3) . . . . ?
C3A C2A C6A C7A -102.0(4) . . . . ?
C4A C1A O1A C2A 43.8(3) . . . . ?
C4A C1A O2A C5A -75.3(3) . . . . ?
C4A C1A C11A C12A 152.5(3) . . . . ?
C4A C1A C11A C16A -31.4(4) . . . . ?
C5A C6A C7A C8A 0.3(5) . . . . ?
C6A C2A C3A C4A -84.4(3) . . . . ?
C6A C5A C10A C9A 1.8(5) . . . . ?
C6A C7A C8A C9A 0.2(5) . . . . ?
C7A C8A C9A C10A 0.2(5) . . . . ?
C8A C9A C10A C5A -1.2(5) . . . . ?
C10A C5A C6A C2A 179.2(3) . . . . ?
C10A C5A C6A C7A -1.3(4) . . . . ?
C11A C1A O1A C2A 172.5(2) . . . . ?
C11A C1A O2A C5A 156.4(2) . . . . ?
C11A C1A C4A C3A -147.2(2) . . . . ?
C11A C12A C13A C14A 0.3(5) . . . . ?
C12A C11A C16A C15A 0.5(4) . . . . ?
C12A C13A C14A C15A -0.2(5) . . . . ?
C13A C14A C15A C16A 0.2(5) . . . . ?
C14A C15A C16A C11A -0.4(5) . . . . ?
C16A C11A C12A C13A -0.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
####################################################################### 
# 
# 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_psu-987(fa-1302)
_database_code_depnum_ccdc_archive 'CCDC 2117821'
loop_
_audit_author_name
_audit_author_address
'Aleksandr Rubtsov'
;Perm State University
Russia
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
1-(4-methoxyphenyl)-2-(5-nitro-2,3-dihydrobenzofuran-2-yl)ethan-1-one
_chemical_formula_moiety         'C17 H15 N O5'
_chemical_formula_sum            'C17 H15 N O5'
_chemical_formula_weight         313.30
_chemical_melting_point          437
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   17.805(8)
_cell_length_b                   11.018(4)
_cell_length_c                   7.659(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.15(4)
_cell_angle_gamma                90
_cell_volume                     1478.9(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    981
_cell_measurement_temperature    295.15
_cell_measurement_theta_max      21.7950
_cell_measurement_theta_min      3.2930
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7295
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.398
_diffrn_reflns_theta_min         2.970
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   89.00   1.0000  155.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6947   77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -95.00   16.00   1.0000  155.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3197  -77.0000    0.0000 111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0376592000
_diffrn_orient_matrix_UB_12      0.0187869000
_diffrn_orient_matrix_UB_13      -0.0350970000
_diffrn_orient_matrix_UB_21      0.0025173000
_diffrn_orient_matrix_UB_22      0.0461532000
_diffrn_orient_matrix_UB_23      0.0653804000
_diffrn_orient_matrix_UB_31      0.0142901000
_diffrn_orient_matrix_UB_32      0.0409201000
_diffrn_orient_matrix_UB_33      -0.0579267000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1298
_reflns_number_total             3486
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3486
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2477
_refine_ls_R_factor_gt           0.1097
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1747P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2903
_refine_ls_wR_factor_ref         0.3749
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.5613(3) 0.3483(4) 0.1398(6) 0.0522(13) Uani 1 1 d . . . . .
N1 N 0.9953(5) 0.2228(8) 0.6689(10) 0.120(2) Uani 1 1 d . . . . .
O1 O 0.5807(2) 0.2663(3) 0.0517(4) 0.0729(12) Uani 1 1 d . . . . .
C2 C 0.6198(3) 0.4311(4) 0.2453(6) 0.0580(13) Uani 1 1 d . . . . .
H2A H 0.609073 0.513881 0.205625 0.070 Uiso 1 1 calc R U . . .
H2B H 0.614836 0.426907 0.369215 0.070 Uiso 1 1 calc R U . . .
O2 O 0.7487(2) 0.4900(3) 0.3380(6) 0.0864(13) Uani 1 1 d . . . . .
C3 C 0.7001(3) 0.4010(4) 0.2296(7) 0.0597(14) Uani 1 1 d . . . . .
H3 H 0.706334 0.409147 0.105502 0.072 Uiso 1 1 calc R U . . .
O3 O 0.9857(4) 0.1081(8) 0.6281(10) 0.163(3) Uani 1 1 d . . . . .
C4 C 0.7267(3) 0.2743(4) 0.2976(6) 0.0509(12) Uani 1 1 d . . . . .
H4A H 0.693218 0.240076 0.371929 0.061 Uiso 1 1 calc R U . . .
H4B H 0.730079 0.219042 0.200717 0.061 Uiso 1 1 calc R U . . .
O4 O 1.0447(3) 0.2628(8) 0.7561(9) 0.167(4) Uani 1 1 d . . . . .
C5 C 0.8033(3) 0.3031(5) 0.4016(6) 0.0603(14) Uani 1 1 d . . . . .
O5 O 0.2511(2) 0.4194(4) 0.1656(5) 0.0872(13) Uani 1 1 d . . . . .
C6 C 0.8104(3) 0.4276(6) 0.4212(7) 0.0726(16) Uani 1 1 d . . . . .
C7 C 0.8722(4) 0.4847(7) 0.5196(9) 0.101(2) Uani 1 1 d . . . . .
H7 H 0.874647 0.568394 0.534900 0.121 Uiso 1 1 calc R U . . .
C8 C 0.9285(4) 0.4103(7) 0.5918(10) 0.099(2) Uani 1 1 d . . . . .
H8 H 0.971926 0.445617 0.657397 0.119 Uiso 1 1 calc R U . . .
C9 C 0.9276(3) 0.2861(6) 0.5770(7) 0.0703(16) Uani 1 1 d . . . . .
C10 C 0.8615(4) 0.2290(7) 0.4785(8) 0.091(2) Uani 1 1 d . . . . .
H10 H 0.858071 0.145020 0.467174 0.109 Uiso 1 1 calc R U . . .
C11 C 0.4801(3) 0.3677(4) 0.1492(6) 0.0518(13) Uani 1 1 d . . . . .
C12 C 0.4259(3) 0.2840(4) 0.0658(6) 0.0577(13) Uani 1 1 d . . . . .
H12 H 0.442368 0.217399 0.008082 0.069 Uiso 1 1 calc R U . . .
C13 C 0.3494(3) 0.2978(5) 0.0671(6) 0.0609(14) Uani 1 1 d . . . . .
H13 H 0.314310 0.241833 0.010111 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3252(3) 0.3962(5) 0.1545(6) 0.0606(14) Uani 1 1 d . . . . .
C15 C 0.3774(3) 0.4791(4) 0.2409(6) 0.0585(13) Uani 1 1 d . . . . .
H15 H 0.360864 0.544420 0.301220 0.070 Uiso 1 1 calc R U . . .
C16 C 0.4528(3) 0.4645(4) 0.2370(6) 0.0592(14) Uani 1 1 d . . . . .
H16 H 0.487372 0.520888 0.294871 0.071 Uiso 1 1 calc R U . . .
C17 C 0.1926(3) 0.3446(7) 0.0660(10) 0.107(2) Uani 1 1 d . . . . .
H17A H 0.196110 0.348087 -0.057559 0.161 Uiso 1 1 calc R U . . .
H17B H 0.143449 0.373560 0.082212 0.161 Uiso 1 1 calc R U . . .
H17C H 0.199188 0.262284 0.106839 0.161 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.213(5) . ?
C1 C2 1.507(7) . ?
C1 C11 1.477(7) . ?
N1 O3 1.306(9) . ?
N1 O4 1.099(9) . ?
N1 C9 1.460(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.493(7) . ?
O2 C3 1.465(6) . ?
O2 C6 1.356(7) . ?
C3 H3 0.9800 . ?
C3 C4 1.535(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.488(7) . ?
C5 C6 1.383(8) . ?
C5 C10 1.369(8) . ?
O5 C14 1.361(6) . ?
O5 C17 1.437(7) . ?
C6 C7 1.371(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.338(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(9) . ?
C9 C10 1.428(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.404(6) . ?
C11 C16 1.393(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(7) . ?
C14 C15 1.385(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.358(7) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 C1 C2 120.8(5) . . ?
O1 C1 C11 120.8(4) . . ?
C11 C1 C2 118.4(4) . . ?
O3 N1 C9 106.6(8) . . ?
O4 N1 O3 126.2(9) . . ?
O4 N1 C9 127.3(9) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 C1 113.8(4) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C6 O2 C3 106.0(4) . . ?
C2 C3 H3 109.4 . . ?
C2 C3 C4 114.6(4) . . ?
O2 C3 C2 106.6(4) . . ?
O2 C3 H3 109.4 . . ?
O2 C3 C4 107.5(4) . . ?
C4 C3 H3 109.4 . . ?
C3 C4 H4A 111.6 . . ?
C3 C4 H4B 111.6 . . ?
H4A C4 H4B 109.4 . . ?
C5 C4 C3 100.7(4) . . ?
C5 C4 H4A 111.6 . . ?
C5 C4 H4B 111.6 . . ?
C6 C5 C4 109.1(4) . . ?
C10 C5 C4 131.0(6) . . ?
C10 C5 C6 119.8(6) . . ?
C14 O5 C17 118.7(5) . . ?
O2 C6 C5 113.6(5) . . ?
O2 C6 C7 122.0(6) . . ?
C7 C6 C5 124.3(6) . . ?
C6 C7 H7 122.7 . . ?
C8 C7 C6 114.6(7) . . ?
C8 C7 H7 122.7 . . ?
C7 C8 H8 117.3 . . ?
C7 C8 C9 125.5(7) . . ?
C9 C8 H8 117.3 . . ?
C8 C9 N1 116.1(7) . . ?
C8 C9 C10 118.6(6) . . ?
C10 C9 N1 125.3(7) . . ?
C5 C10 C9 117.1(6) . . ?
C5 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C12 C11 C1 118.8(4) . . ?
C16 C11 C1 124.2(5) . . ?
C16 C11 C12 116.9(5) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(5) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(5) . . ?
C14 C13 H13 120.5 . . ?
O5 C14 C13 124.4(5) . . ?
O5 C14 C15 115.0(5) . . ?
C13 C14 C15 120.6(5) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 H16 118.9 . . ?
C15 C16 C11 122.1(5) . . ?
C15 C16 H16 118.9 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C1 C2 C3 O2 179.6(4) . . . . ?
C1 C2 C3 C4 -61.7(5) . . . . ?
C1 C11 C12 C13 -179.0(4) . . . . ?
C1 C11 C16 C15 179.5(4) . . . . ?
N1 C9 C10 C5 179.8(5) . . . . ?
O1 C1 C2 C3 -0.3(6) . . . . ?
O1 C1 C11 C12 5.0(7) . . . . ?
O1 C1 C11 C16 -175.3(4) . . . . ?
C2 C1 C11 C12 -173.8(4) . . . . ?
C2 C1 C11 C16 5.9(7) . . . . ?
C2 C3 C4 C5 -135.1(4) . . . . ?
O2 C3 C4 C5 -16.9(5) . . . . ?
O2 C6 C7 C8 -179.4(5) . . . . ?
C3 O2 C6 C5 -9.2(6) . . . . ?
C3 O2 C6 C7 172.8(5) . . . . ?
C3 C4 C5 C6 11.7(5) . . . . ?
C3 C4 C5 C10 -170.6(5) . . . . ?
O3 N1 C9 C8 -175.4(6) . . . . ?
O3 N1 C9 C10 6.1(8) . . . . ?
C4 C5 C6 O2 -2.1(6) . . . . ?
C4 C5 C6 C7 175.8(5) . . . . ?
C4 C5 C10 C9 -177.5(4) . . . . ?
O4 N1 C9 C8 4.9(10) . . . . ?
O4 N1 C9 C10 -173.7(7) . . . . ?
C5 C6 C7 C8 2.8(9) . . . . ?
O5 C14 C15 C16 -179.7(4) . . . . ?
C6 O2 C3 C2 139.8(4) . . . . ?
C6 O2 C3 C4 16.5(5) . . . . ?
C6 C5 C10 C9 0.1(7) . . . . ?
C6 C7 C8 C9 -1.4(10) . . . . ?
C7 C8 C9 N1 -179.2(6) . . . . ?
C7 C8 C9 C10 -0.6(9) . . . . ?
C8 C9 C10 C5 1.3(7) . . . . ?
C10 C5 C6 O2 179.8(4) . . . . ?
C10 C5 C6 C7 -2.3(8) . . . . ?
C11 C1 C2 C3 178.5(4) . . . . ?
C11 C12 C13 C14 -0.6(7) . . . . ?
C12 C11 C16 C15 -0.8(7) . . . . ?
C12 C13 C14 O5 -179.8(4) . . . . ?
C12 C13 C14 C15 -0.6(7) . . . . ?
C13 C14 C15 C16 1.1(7) . . . . ?
C14 C15 C16 C11 -0.4(7) . . . . ?
C16 C11 C12 C13 1.3(7) . . . . ?
C17 O5 C14 C13 -6.6(8) . . . . ?
C17 O5 C14 C15 174.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
####################################################################### 
# 
# 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_psu-1014(mu-330)
_database_code_depnum_ccdc_archive 'CCDC 2117822'
loop_
_audit_author_name
_audit_author_address
'Aleksandr Rubtsov'
;Perm State University
Russia
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
2-(2,3-dihydrobenzofuran-2-yl)-2,3-dihydro-1H-inden-1-one
_chemical_formula_moiety         'C17 H14 O2'
_chemical_formula_sum            'C17 H14 O2'
_chemical_formula_weight         250.28
_chemical_melting_point          373
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   15.015(4)
_cell_length_b                   6.0331(12)
_cell_length_c                   15.540(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.39(4)
_cell_angle_gamma                90
_cell_volume                     1261.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2019
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.7130
_cell_measurement_theta_min      3.5940
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6616
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.195
_diffrn_reflns_theta_min         2.927
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -7.00   19.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978  -99.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   62.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978   57.0000 -120.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00   12.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978  -38.0000   90.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0363458000
_diffrn_orient_matrix_UB_12      -0.0096640000
_diffrn_orient_matrix_UB_13      0.0483356000
_diffrn_orient_matrix_UB_21      0.0382546000
_diffrn_orient_matrix_UB_22      0.0071298000
_diffrn_orient_matrix_UB_23      -0.0149628000
_diffrn_orient_matrix_UB_31      0.0008934000
_diffrn_orient_matrix_UB_32      0.1169972000
_diffrn_orient_matrix_UB_33      0.0050762000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2120
_reflns_number_total             2984
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.1923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.18031(11) 0.0237(3) -0.01717(11) 0.0506(4) Uani 1 1 d . . . . .
H1 H 0.142383 0.114495 -0.074154 0.061 Uiso 1 1 calc R U . . .
O1 O 0.19434(9) 0.14842(18) 0.06886(8) 0.0573(3) Uani 1 1 d . . . . .
C2 C 0.11905(12) -0.1825(3) -0.01990(12) 0.0581(5) Uani 1 1 d . . . . .
H2A H 0.053285 -0.176490 -0.073654 0.070 Uiso 1 1 calc R U . . .
H2B H 0.152088 -0.317156 -0.024341 0.070 Uiso 1 1 calc R U . . .
O2 O 0.31165(10) 0.3430(2) -0.05391(9) 0.0733(4) Uani 1 1 d . . . . .
C3 C 0.11357(11) -0.1703(3) 0.07433(11) 0.0495(4) Uani 1 1 d . . . . .
C4 C 0.15723(10) 0.0248(3) 0.11952(11) 0.0456(4) Uani 1 1 d . . . . .
C5 C 0.16312(11) 0.0839(3) 0.20755(12) 0.0530(4) Uani 1 1 d . . . . .
H5 H 0.192236 0.216979 0.236763 0.064 Uiso 1 1 calc R U . . .
C6 C 0.12437(12) -0.0609(3) 0.25085(12) 0.0593(5) Uani 1 1 d . . . . .
H6 H 0.127023 -0.024494 0.310106 0.071 Uiso 1 1 calc R U . . .
C7 C 0.08211(13) -0.2570(4) 0.20809(13) 0.0704(5) Uani 1 1 d . . . . .
H7 H 0.057003 -0.352970 0.238780 0.084 Uiso 1 1 calc R U . . .
C8 C 0.07640(13) -0.3139(3) 0.11937(13) 0.0668(5) Uani 1 1 d . . . . .
H8 H 0.047782 -0.447565 0.090534 0.080 Uiso 1 1 calc R U . . .
C9 C 0.28139(11) -0.0280(3) -0.01217(10) 0.0466(4) Uani 1 1 d . . . . .
H9 H 0.270292 -0.104209 -0.071794 0.056 Uiso 1 1 calc R U . . .
C10 C 0.34243(12) 0.1787(3) -0.00448(10) 0.0477(4) Uani 1 1 d . . . . .
C11 C 0.44313(11) 0.1416(2) 0.07170(10) 0.0447(4) Uani 1 1 d . . . . .
C12 C 0.44735(11) -0.0610(2) 0.11449(11) 0.0450(4) Uani 1 1 d . . . . .
C13 C 0.34813(11) -0.1755(3) 0.07132(12) 0.0543(4) Uani 1 1 d . . . . .
H13A H 0.322020 -0.188876 0.118064 0.065 Uiso 1 1 calc R U . . .
H13B H 0.353626 -0.322332 0.048718 0.065 Uiso 1 1 calc R U . . .
C14 C 0.53575(12) -0.1317(3) 0.18946(13) 0.0570(4) Uani 1 1 d . . . . .
H14 H 0.539413 -0.267981 0.218790 0.068 Uiso 1 1 calc R U . . .
C15 C 0.61751(13) 0.0031(3) 0.21945(13) 0.0661(5) Uani 1 1 d . . . . .
H15 H 0.677005 -0.043176 0.269639 0.079 Uiso 1 1 calc R U . . .
C16 C 0.61362(13) 0.2061(3) 0.17687(13) 0.0659(5) Uani 1 1 d . . . . .
H16 H 0.670227 0.294288 0.198452 0.079 Uiso 1 1 calc R U . . .
C17 C 0.52646(13) 0.2784(3) 0.10273(12) 0.0582(5) Uani 1 1 d . . . . .
H17 H 0.523181 0.415287 0.073970 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9800 . ?
C1 O1 1.4655(19) . ?
C1 C2 1.537(2) . ?
C1 C9 1.517(2) . ?
O1 C4 1.3701(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.505(2) . ?
O2 C10 1.2126(19) . ?
C3 C4 1.378(2) . ?
C3 C8 1.378(2) . ?
C4 C5 1.378(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.367(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.521(2) . ?
C9 C13 1.524(2) . ?
C10 C11 1.465(2) . ?
C11 C12 1.379(2) . ?
C11 C17 1.394(2) . ?
C12 C13 1.503(2) . ?
C12 C14 1.388(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.370(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 H17 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
O1 C1 H1 109.1 . . ?
O1 C1 C2 106.42(12) . . ?
O1 C1 C9 108.90(12) . . ?
C2 C1 H1 109.1 . . ?
C9 C1 H1 109.1 . . ?
C9 C1 C2 114.07(14) . . ?
C4 O1 C1 108.32(12) . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 C1 102.97(12) . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C4 C3 C2 108.57(14) . . ?
C8 C3 C2 132.32(15) . . ?
C8 C3 C4 119.10(16) . . ?
O1 C4 C3 113.28(14) . . ?
O1 C4 C5 124.49(14) . . ?
C3 C4 C5 122.23(15) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.72(16) . . ?
C6 C5 H5 121.1 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.08(17) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.53(17) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 119.32(17) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C1 C9 H9 107.6 . . ?
C1 C9 C10 112.94(13) . . ?
C1 C9 C13 115.32(13) . . ?
C10 C9 H9 107.6 . . ?
C10 C9 C13 105.46(12) . . ?
C13 C9 H9 107.6 . . ?
O2 C10 C9 125.02(15) . . ?
O2 C10 C11 127.05(15) . . ?
C11 C10 C9 107.93(13) . . ?
C12 C11 C10 109.54(13) . . ?
C12 C11 C17 121.07(16) . . ?
C17 C11 C10 129.39(15) . . ?
C11 C12 C13 111.60(14) . . ?
C11 C12 C14 119.91(15) . . ?
C14 C12 C13 128.46(15) . . ?
C9 C13 H13A 110.8 . . ?
C9 C13 H13B 110.8 . . ?
C12 C13 C9 104.94(13) . . ?
C12 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C12 C14 H14 120.6 . . ?
C15 C14 C12 118.77(17) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.51(17) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.32(17) . . ?
C17 C16 H16 119.8 . . ?
C11 C17 H17 120.8 . . ?
C16 C17 C11 118.41(17) . . ?
C16 C17 H17 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C4 C3 -3.28(17) . . . . ?
C1 O1 C4 C5 175.87(14) . . . . ?
C1 C2 C3 C4 4.85(17) . . . . ?
C1 C2 C3 C8 -173.87(17) . . . . ?
C1 C9 C10 O2 -46.9(2) . . . . ?
C1 C9 C10 C11 133.43(13) . . . . ?
C1 C9 C13 C12 -132.39(14) . . . . ?
O1 C1 C2 C3 -6.59(16) . . . . ?
O1 C1 C9 C10 -58.42(16) . . . . ?
O1 C1 C9 C13 62.95(17) . . . . ?
O1 C4 C5 C6 -178.41(14) . . . . ?
C2 C1 O1 C4 6.23(16) . . . . ?
C2 C1 C9 C10 -177.11(12) . . . . ?
C2 C1 C9 C13 -55.74(17) . . . . ?
C2 C3 C4 O1 -1.21(18) . . . . ?
C2 C3 C4 C5 179.62(14) . . . . ?
C2 C3 C8 C7 179.80(17) . . . . ?
O2 C10 C11 C12 176.83(15) . . . . ?
O2 C10 C11 C17 -2.5(3) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C3 C8 C7 1.2(3) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C8 C3 C4 O1 177.71(14) . . . . ?
C8 C3 C4 C5 -1.5(2) . . . . ?
C9 C1 O1 C4 -117.16(13) . . . . ?
C9 C1 C2 C3 113.51(14) . . . . ?
C9 C10 C11 C12 -3.53(16) . . . . ?
C9 C10 C11 C17 177.16(15) . . . . ?
C10 C9 C13 C12 -7.05(16) . . . . ?
C10 C11 C12 C13 -1.18(18) . . . . ?
C10 C11 C12 C14 -179.63(13) . . . . ?
C10 C11 C17 C16 179.67(15) . . . . ?
C11 C12 C13 C9 5.32(18) . . . . ?
C11 C12 C14 C15 0.0(2) . . . . ?
C12 C11 C17 C16 0.4(2) . . . . ?
C12 C14 C15 C16 0.0(3) . . . . ?
C13 C9 C10 O2 -173.72(15) . . . . ?
C13 C9 C10 C11 6.63(16) . . . . ?
C13 C12 C14 C15 -178.13(15) . . . . ?
C14 C12 C13 C9 -176.39(15) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C11 -0.4(3) . . . . ?
C17 C11 C12 C13 178.19(14) . . . . ?
C17 C11 C12 C14 -0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
