# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_exp_1855
_database_code_depnum_ccdc_archive 'CCDC 1942073'
loop_
_audit_author_name
_audit_author_address
'Jian Li'
;School of Chemistry and  Pharmacy, Northwest A and F University, Yangling, China
China
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2021-06-25 downloaded from the CCDC.
;
_audit_creation_date             2019-06-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 O'
_chemical_formula_sum            'C27 H20 O'
_chemical_formula_weight         360.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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                   16.9512(17)
_cell_length_b                   7.3838(4)
_cell_length_c                   16.2147(15)
_cell_angle_alpha                90
_cell_angle_beta                 116.035(12)
_cell_angle_gamma                90
_cell_volume                     1823.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2354
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3090
_cell_measurement_theta_min      2.8610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6306
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.445
_diffrn_reflns_theta_min         2.901
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  32.00   1.00    1.50    --  -40.73  57.00   0.00   97
  2  ω    -64.00 -13.00   1.00    1.50    --  -40.73 -57.00  30.00   51
  3  ω   -105.00 -17.00   1.00    1.50    --  -40.73 -57.00-150.00   88
  4  ω     70.00 121.00   1.00    2.00    --  106.95-125.00 -60.00   51
  5  ω     74.00 101.00   1.00    2.00    --  106.95 -95.00   0.00   27
  6  ω     31.00 139.00   1.00    2.00    --  106.95 -77.00 120.00  108
  7  ω     82.00 175.00   1.00    2.00    --  106.95  30.00   0.00   93
  8  ω    136.00 161.00   1.00    2.00    --  106.95 125.00  60.00   25
  9  ω     79.00 172.00   1.00    2.00    --  106.95  30.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0743439000
_diffrn_orient_matrix_UB_12      0.0296183000
_diffrn_orient_matrix_UB_13      -0.0288473000
_diffrn_orient_matrix_UB_21      -0.0680733000
_diffrn_orient_matrix_UB_22      0.0571515000
_diffrn_orient_matrix_UB_23      -0.0966040000
_diffrn_orient_matrix_UB_31      0.0085003000
_diffrn_orient_matrix_UB_32      0.1984058000
_diffrn_orient_matrix_UB_33      0.0320529000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2639
_reflns_number_total             3545
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.061
_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)+(0.0301P)²+6.4600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.1882
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C27(H27), C14(H14), C6(H6), C26(H26), C17(H17), C23(H23), C21(H21),
 C3(H3), C24(H24), C25(H25), C18(H18), C4(H4), C5(H5), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.55465(16) 0.6636(3) 0.64920(16) 0.0213(5) Uani 1 1 d . . . . .
C9 C 0.4047(2) 0.8522(5) 0.3680(2) 0.0168(7) Uani 1 1 d . . . . .
C16 C 0.8200(2) 0.5077(4) 0.7149(2) 0.0174(7) Uani 1 1 d . . . . .
C7 C 0.3711(2) 0.8347(4) 0.4940(2) 0.0158(7) Uani 1 1 d . . . . .
C22 C 0.2630(2) 0.9801(4) 0.2444(2) 0.0160(7) Uani 1 1 d . . . . .
C15 C 0.7303(2) 0.5700(4) 0.6905(2) 0.0180(7) Uani 1 1 d . . . . .
H15 H 0.715591 0.590362 0.738667 0.022 Uiso 1 1 calc R . . . .
C1 C 0.3224(2) 0.9208(5) 0.3383(2) 0.0169(7) Uani 1 1 d . . . . .
C2 C 0.3007(2) 0.9153(4) 0.4176(2) 0.0169(7) Uani 1 1 d . . . . .
C13 C 0.5794(2) 0.6629(5) 0.5883(2) 0.0171(7) Uani 1 1 d . . . . .
C12 C 0.5213(2) 0.7268(5) 0.4943(2) 0.0168(7) Uani 1 1 d . . . . .
C27 C 0.1730(2) 0.9473(5) 0.2069(2) 0.0183(7) Uani 1 1 d . . . . .
H27 H 0.149417 0.890999 0.242343 0.022 Uiso 1 1 calc R . . . .
C8 C 0.4395(2) 0.7968(5) 0.4642(2) 0.0166(7) Uani 1 1 d . . . . .
C14 C 0.6679(2) 0.6003(5) 0.6058(2) 0.0191(7) Uani 1 1 d . . . . .
H14 H 0.680630 0.581303 0.556175 0.023 Uiso 1 1 calc R . . . .
C6 C 0.3659(2) 0.8074(5) 0.5761(2) 0.0192(7) Uani 1 1 d . . . . .
H6 H 0.411861 0.752837 0.625609 0.023 Uiso 1 1 calc R . . . .
C26 C 0.1178(2) 0.9978(5) 0.1170(2) 0.0210(7) Uani 1 1 d . . . . .
H26 H 0.057940 0.974370 0.092749 0.025 Uiso 1 1 calc R . . . .
C17 C 0.8821(2) 0.5105(5) 0.8074(2) 0.0221(8) Uani 1 1 d . . . . .
H17 H 0.866841 0.557882 0.851588 0.026 Uiso 1 1 calc R . . . .
C23 C 0.2967(2) 1.0664(5) 0.1894(2) 0.0182(7) Uani 1 1 d . . . . .
H23 H 0.356471 1.090293 0.213076 0.022 Uiso 1 1 calc R . . . .
C21 C 0.8450(2) 0.4388(5) 0.6494(2) 0.0208(7) Uani 1 1 d . . . . .
H21 H 0.805093 0.437996 0.587675 0.025 Uiso 1 1 calc R . . . .
C11 C 0.5495(2) 0.7289(5) 0.4173(2) 0.0190(7) Uani 1 1 d . . . . .
C3 C 0.2276(2) 0.9764(5) 0.4266(2) 0.0193(7) Uani 1 1 d . . . . .
H3 H 0.182304 1.035016 0.378101 0.023 Uiso 1 1 calc R . . . .
C24 C 0.2412(2) 1.1162(5) 0.1000(2) 0.0204(7) Uani 1 1 d . . . . .
H24 H 0.264192 1.172600 0.064029 0.024 Uiso 1 1 calc R . . . .
C25 C 0.1519(2) 1.0826(5) 0.0639(2) 0.0213(7) Uani 1 1 d . . . . .
H25 H 0.115037 1.117013 0.004027 0.026 Uiso 1 1 calc R . . . .
C18 C 0.9660(2) 0.4430(5) 0.8333(3) 0.0266(8) Uani 1 1 d . . . . .
H18 H 1.006685 0.445527 0.894702 0.032 Uiso 1 1 calc R . . . .
C4 C 0.2230(2) 0.9486(5) 0.5096(2) 0.0209(7) Uani 1 1 d . . . . .
H4 H 0.173758 0.988180 0.515798 0.025 Uiso 1 1 calc R . . . .
C5 C 0.2903(2) 0.8632(5) 0.5830(2) 0.0213(7) Uani 1 1 d . . . . .
H5 H 0.285080 0.843014 0.636994 0.026 Uiso 1 1 calc R . . . .
C20 C 0.9289(2) 0.3719(5) 0.6764(3) 0.0241(8) Uani 1 1 d . . . . .
H20 H 0.944951 0.326333 0.632464 0.029 Uiso 1 1 calc R . . . .
C10 C 0.4706(2) 0.8093(6) 0.3327(2) 0.0226(8) Uani 1 1 d . . . . .
C19 C 0.9895(2) 0.3721(5) 0.7683(3) 0.0273(8) Uani 1 1 d . . . . .
H19 H 1.045430 0.324743 0.786008 0.033 Uiso 1 1 calc R . . . .
H11A H 0.606(2) 0.806(5) 0.435(2) 0.014(9) Uiso 1 1 d . . . . .
H11B H 0.566(2) 0.600(5) 0.404(2) 0.020(10) Uiso 1 1 d . . . . .
H10A H 0.445(3) 0.714(7) 0.282(3) 0.040(13) Uiso 1 1 d . . . . .
H10B H 0.488(3) 0.912(6) 0.308(3) 0.033(12) Uiso 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
O1 C13 1.230(4) . ?
C9 C1 1.358(5) . ?
C9 C8 1.462(4) . ?
C9 C10 1.496(5) . ?
C16 C15 1.467(5) . ?
C16 C17 1.405(5) . ?
C16 C21 1.400(5) . ?
C7 C2 1.420(5) . ?
C7 C8 1.465(4) . ?
C7 C6 1.387(5) . ?
C22 C1 1.476(4) . ?
C22 C27 1.394(5) . ?
C22 C23 1.404(5) . ?
C15 C14 1.335(5) . ?
C1 C2 1.484(5) . ?
C2 C3 1.386(5) . ?
C13 C12 1.483(4) . ?
C13 C14 1.474(5) . ?
C12 C8 1.355(5) . ?
C12 C11 1.521(5) . ?
C27 C26 1.393(5) . ?
C6 C5 1.396(5) . ?
C26 C25 1.380(5) . ?
C17 C18 1.387(5) . ?
C23 C24 1.387(5) . ?
C21 C20 1.382(5) . ?
C11 C10 1.552(5) . ?
C3 C4 1.398(5) . ?
C24 C25 1.385(5) . ?
C18 C19 1.382(5) . ?
C4 C5 1.387(5) . ?
C20 C19 1.391(5) . ?

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
C1 C9 C8 110.7(3) . . ?
C1 C9 C10 140.1(3) . . ?
C8 C9 C10 109.2(3) . . ?
C17 C16 C15 119.0(3) . . ?
C21 C16 C15 122.2(3) . . ?
C21 C16 C17 118.8(3) . . ?
C2 C7 C8 106.0(3) . . ?
C6 C7 C2 121.0(3) . . ?
C6 C7 C8 133.0(3) . . ?
C27 C22 C1 121.2(3) . . ?
C27 C22 C23 118.3(3) . . ?
C23 C22 C1 120.4(3) . . ?
C14 C15 C16 126.1(3) . . ?
C9 C1 C22 127.3(3) . . ?
C9 C1 C2 106.8(3) . . ?
C22 C1 C2 125.9(3) . . ?
C7 C2 C1 109.6(3) . . ?
C3 C2 C7 119.5(3) . . ?
C3 C2 C1 130.9(3) . . ?
O1 C13 C12 121.2(3) . . ?
O1 C13 C14 121.6(3) . . ?
C14 C13 C12 117.2(3) . . ?
C13 C12 C11 122.8(3) . . ?
C8 C12 C13 127.2(3) . . ?
C8 C12 C11 110.0(3) . . ?
C26 C27 C22 120.9(3) . . ?
C9 C8 C7 106.9(3) . . ?
C12 C8 C9 111.1(3) . . ?
C12 C8 C7 141.9(3) . . ?
C15 C14 C13 122.0(3) . . ?
C7 C6 C5 118.8(3) . . ?
C25 C26 C27 120.1(3) . . ?
C18 C17 C16 120.4(3) . . ?
C24 C23 C22 120.4(3) . . ?
C20 C21 C16 120.1(3) . . ?
C12 C11 C10 105.6(3) . . ?
C2 C3 C4 119.0(3) . . ?
C25 C24 C23 120.5(3) . . ?
C26 C25 C24 119.8(3) . . ?
C19 C18 C17 120.4(3) . . ?
C5 C4 C3 121.3(3) . . ?
C4 C5 C6 120.3(3) . . ?
C21 C20 C19 120.8(3) . . ?
C9 C10 C11 104.0(3) . . ?
C18 C19 C20 119.5(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.628
