# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_zhangmch_210125_3
_database_code_depnum_ccdc_archive 'CCDC 2101411'
loop_
_audit_author_name
_audit_author_address
'Yunyun chen'
;sysu
China
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3-(2-chlorophenyl)-5-(5-oxo-1,5-diphenylpent-1-yn-3-yl)furan-2(5H)-one
_chemical_formula_moiety         'C27 H19 Cl O3'
_chemical_formula_sum            'C27 H19 Cl O3'
_chemical_formula_weight         426.87
_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'
Cl Cl 0.3639 0.7018 '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                   9.4913(2)
_cell_length_b                   11.5055(2)
_cell_length_c                   19.8764(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.697(2)
_cell_angle_gamma                90
_cell_volume                     2159.82(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7176
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.7810
_cell_measurement_theta_min      4.4290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15091
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.100
_diffrn_reflns_theta_min         4.446
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -27.00   0.50    3.00    -- -100.00  61.00  60.00   60
  2  ω    -56.00 -31.00   0.50    3.00    -- -100.00  61.00   0.00   50
  3  ω    -27.00  15.00   0.50    0.50    --  -46.62  30.00   7.00   84
  4  ω    -57.00 -27.00   0.50    3.00    -- -100.00  61.00  90.00   60
  5  ω    -55.00 -27.00   0.50    3.00    -- -100.00  61.00 120.00   56
  6  ω    -65.00 -28.00   0.50    3.00    -- -100.00  61.00 150.00   74
  7  ω    -39.00  22.00   0.50    0.50    --  -46.62  38.00 150.00  122
  8  ω    -12.00  18.00   0.50    0.50    --  -46.62  19.00 150.00   60
  9  ω     38.00 112.00   0.50    0.50    --   46.62  30.00   7.00  148
 10  ω     94.00 178.00   0.50    3.00    --  105.44  30.00   7.00  168
 11  ω     57.00  84.00   0.50    3.00    --  105.44 -94.00  60.00   54
 12  ω     68.00 107.00   0.50    3.00    --  105.44 -77.00  30.00   78
 13  ω     41.00  66.00   0.50    3.00    --  105.44 -61.00  90.00   50
 14  ω     36.00  64.00   0.50    3.00    --  105.44 -77.00  30.00   56
 15  ω     35.00  68.00   0.50    3.00    --  105.44 -61.00 -60.00   66
 16  ω     33.00 105.00   0.50    3.00    --  105.44 -94.00-120.00  144
 17  ω     34.00  73.00   0.50    3.00    --  105.44 -61.00-120.00   78
 18  ω     34.00  73.00   0.50    3.00    --  105.44 -61.00 -90.00   78
 19  ω     34.00  73.00   0.50    3.00    --  105.44 -61.00-150.00   78
 20  ω    -20.00   5.00   0.50    0.50    --   46.62 -30.00-153.00   50
 21  ω   -106.00 -35.00   0.50    0.50    --  -46.62 -30.00-153.00  142
 22  ω    -67.00 -28.00   0.50    3.00    -- -100.00  61.00-180.00   78
 23  ω    -63.00 -27.00   0.50    3.00    -- -100.00  77.00-180.00   72
 24  ω    -82.00 -40.00   0.50    3.00    -- -100.00 125.00 -90.00   84
 25  ω    -99.00 -74.00   0.50    3.00    -- -100.00  77.00-180.00   50
 26  ω   -114.00 -89.00   0.50    3.00    -- -100.00 -30.00-153.00   50
 27  ω   -119.00 -94.00   0.50    0.50    --  -46.62-125.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0520803000
_diffrn_orient_matrix_UB_12      0.0153086000
_diffrn_orient_matrix_UB_13      -0.0753855000
_diffrn_orient_matrix_UB_21      0.1415876000
_diffrn_orient_matrix_UB_22      -0.0484738000
_diffrn_orient_matrix_UB_23      -0.0195723000
_diffrn_orient_matrix_UB_31      -0.0619032000
_diffrn_orient_matrix_UB_32      -0.1238933000
_diffrn_orient_matrix_UB_33      -0.0016563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3698
_reflns_number_total             4305
_reflns_odcompleteness_completeness 99.80
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.825
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.051
_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)+(0.1188P)²+0.9771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1844
_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:
 C12(H12), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C25(H25), C6(H6), C21(H21), C5(H5), C24(H24), C23(H23), C3(H3),
 C4(H4), C22(H22), C29(H29), C31(H31), C30(H30), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl19 Cl -0.00742(6) 0.70043(5) 0.64525(3) 0.0347(2) Uani 1 1 d . . . . .
O7 O 0.51563(17) 0.63460(14) 0.71773(8) 0.0264(4) Uani 1 1 d . . . . .
O18 O 0.48250(19) 0.79539(15) 0.77761(9) 0.0322(4) Uani 1 1 d . . . . .
O15 O 0.71450(18) 0.44688(15) 0.51764(9) 0.0312(4) Uani 1 1 d . . . . .
C1 C 0.2204(2) 0.8424(2) 0.67793(11) 0.0237(5) Uani 1 1 d . . . . .
C20 C 0.9131(2) 0.40878(19) 0.59557(12) 0.0257(5) Uani 1 1 d . . . . .
C10 C 0.3172(2) 0.7419(2) 0.67993(11) 0.0232(5) Uani 1 1 d . . . . .
C12 C 0.5503(2) 0.56667(19) 0.60402(12) 0.0246(5) Uani 1 1 d . . . . .
H12 H 0.502498 0.524322 0.565492 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4471(2) 0.5769(2) 0.65883(12) 0.0251(5) Uani 1 1 d . . . . .
H8 H 0.416746 0.499076 0.671362 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7661(3) 0.45113(19) 0.57646(12) 0.0249(5) Uani 1 1 d . . . . .
C11 C 0.4434(2) 0.7325(2) 0.73058(11) 0.0246(5) Uani 1 1 d . . . . .
C9 C 0.3204(2) 0.6501(2) 0.63887(12) 0.0259(5) Uani 1 1 d . . . . .
H9 H 0.252977 0.634204 0.602856 0.031 Uiso 1 1 calc R U . . .
C25 C 0.9719(3) 0.4013(2) 0.66265(13) 0.0292(5) Uani 1 1 d . . . . .
H25 H 0.917634 0.420696 0.697490 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2763(3) 0.9531(2) 0.69218(11) 0.0249(5) Uani 1 1 d . . . . .
H6 H 0.372717 0.960813 0.705013 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6815(2) 0.4971(2) 0.63134(12) 0.0245(5) Uani 1 1 d . . . . .
H13A H 0.742098 0.546402 0.661372 0.029 Uiso 1 1 calc R U . . .
H13B H 0.651797 0.432178 0.657688 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5881(2) 0.6832(2) 0.58059(12) 0.0264(5) Uani 1 1 d . . . . .
C26 C 0.6531(3) 0.9002(2) 0.55377(13) 0.0299(5) Uani 1 1 d . . . . .
C21 C 0.9969(3) 0.3808(2) 0.54429(13) 0.0311(5) Uani 1 1 d . . . . .
H21 H 0.958587 0.384726 0.499428 0.037 Uiso 1 1 calc R U . . .
C2 C 0.0745(3) 0.8348(2) 0.66024(12) 0.0263(5) Uani 1 1 d . . . . .
C17 C 0.6180(3) 0.7809(2) 0.56686(13) 0.0293(5) Uani 1 1 d . . . . .
C5 C 0.1917(3) 1.0517(2) 0.68770(13) 0.0303(5) Uani 1 1 d . . . . .
H5 H 0.231503 1.124397 0.697347 0.036 Uiso 1 1 calc R U . . .
C24 C 1.1109(3) 0.3651(2) 0.67753(14) 0.0337(6) Uani 1 1 d . . . . .
H24 H 1.148505 0.358145 0.722361 0.040 Uiso 1 1 calc R U . . .
C23 C 1.1938(3) 0.3394(2) 0.62619(15) 0.0334(6) Uani 1 1 d . . . . .
H23 H 1.287640 0.317028 0.636429 0.040 Uiso 1 1 calc R U . . .
C3 C -0.0109(3) 0.9335(2) 0.65587(13) 0.0325(6) Uani 1 1 d . . . . .
H3 H -0.107851 0.926351 0.644166 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0478(3) 1.0416(2) 0.66882(14) 0.0339(6) Uani 1 1 d . . . . .
H4 H -0.009020 1.107569 0.664901 0.041 Uiso 1 1 calc R U . . .
C22 C 1.1367(3) 0.3470(2) 0.55926(15) 0.0355(6) Uani 1 1 d . . . . .
H22 H 1.192133 0.329581 0.524553 0.043 Uiso 1 1 calc R U . . .
C29 C 0.7226(3) 1.1323(2) 0.53156(15) 0.0398(6) Uani 1 1 d . . . . .
H29 H 0.744807 1.209707 0.524143 0.048 Uiso 1 1 calc R U . . .
C31 C 0.7464(4) 0.9291(2) 0.50618(14) 0.0433(7) Uani 1 1 d . . . . .
H31 H 0.784754 0.870720 0.481222 0.052 Uiso 1 1 calc R U . . .
C30 C 0.7823(4) 1.0445(3) 0.49593(15) 0.0448(7) Uani 1 1 d . . . . .
H30 H 0.846457 1.062858 0.465104 0.054 Uiso 1 1 calc R U . . .
C27 C 0.5955(3) 0.9892(3) 0.58847(17) 0.0430(7) Uani 1 1 d . . . . .
H27 H 0.531879 0.971859 0.619716 0.052 Uiso 1 1 calc R U . . .
C28 C 0.6309(4) 1.1039(3) 0.57758(19) 0.0505(8) Uani 1 1 d . . . . .
H28 H 0.591551 1.162468 0.602007 0.061 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
Cl19 C2 1.743(2) . ?
O7 C8 1.443(3) . ?
O7 C11 1.356(3) . ?
O18 C11 1.211(3) . ?
O15 C14 1.223(3) . ?
C1 C10 1.475(3) . ?
C1 C6 1.397(3) . ?
C1 C2 1.398(3) . ?
C20 C14 1.491(3) . ?
C20 C25 1.396(3) . ?
C20 C21 1.391(3) . ?
C10 C11 1.490(3) . ?
C10 C9 1.337(3) . ?
C12 H12 0.9800 . ?
C12 C8 1.540(3) . ?
C12 C13 1.534(3) . ?
C12 C16 1.475(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.490(3) . ?
C14 C13 1.512(3) . ?
C9 H9 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.387(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 C17 1.198(4) . ?
C26 C17 1.442(4) . ?
C26 C31 1.398(4) . ?
C26 C27 1.377(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(4) . ?
C2 C3 1.393(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.385(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.381(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.389(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C22 H22 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.387(4) . ?
C29 C28 1.363(5) . ?
C31 H31 0.9300 . ?
C31 C30 1.391(4) . ?
C30 H30 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.385(4) . ?
C28 H28 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
C11 O7 C8 109.85(17) . . ?
C6 C1 C10 119.1(2) . . ?
C6 C1 C2 117.1(2) . . ?
C2 C1 C10 123.8(2) . . ?
C25 C20 C14 122.6(2) . . ?
C21 C20 C14 118.5(2) . . ?
C21 C20 C25 118.8(2) . . ?
C1 C10 C11 122.2(2) . . ?
C9 C10 C1 130.9(2) . . ?
C9 C10 C11 106.8(2) . . ?
C8 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C13 C12 C8 109.89(19) . . ?
C16 C12 H12 108.3 . . ?
C16 C12 C8 110.24(19) . . ?
C16 C12 C13 111.80(19) . . ?
O7 C8 C12 110.01(18) . . ?
O7 C8 H8 109.5 . . ?
O7 C8 C9 104.02(18) . . ?
C12 C8 H8 109.5 . . ?
C9 C8 C12 114.07(19) . . ?
C9 C8 H8 109.5 . . ?
O15 C14 C20 120.4(2) . . ?
O15 C14 C13 120.9(2) . . ?
C20 C14 C13 118.7(2) . . ?
O7 C11 C10 108.73(19) . . ?
O18 C11 O7 121.3(2) . . ?
O18 C11 C10 129.9(2) . . ?
C10 C9 C8 110.6(2) . . ?
C10 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 C12 113.43(19) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C17 C16 C12 174.6(3) . . ?
C31 C26 C17 121.4(2) . . ?
C27 C26 C17 120.4(2) . . ?
C27 C26 C31 118.2(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 119.6 . . ?
C1 C2 Cl19 120.86(18) . . ?
C3 C2 Cl19 117.76(19) . . ?
C3 C2 C1 121.4(2) . . ?
C16 C17 C26 177.1(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C24 C23 H23 120.1 . . ?
C24 C23 C22 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C28 C29 C30 119.2(3) . . ?
C26 C31 H31 119.8 . . ?
C30 C31 C26 120.4(3) . . ?
C30 C31 H31 119.8 . . ?
C29 C30 C31 120.2(3) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 121.1(3) . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 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
Cl19 C2 C3 C4 178.4(2) . . . . ?
O7 C8 C9 C10 1.7(3) . . . . ?
O15 C14 C13 C12 -16.5(3) . . . . ?
C1 C10 C11 O7 -176.75(19) . . . . ?
C1 C10 C11 O18 4.5(4) . . . . ?
C1 C10 C9 C8 175.0(2) . . . . ?
C1 C6 C5 C4 0.2(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C20 C14 C13 C12 164.69(19) . . . . ?
C20 C25 C24 C23 1.9(4) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C10 C1 C6 C5 176.6(2) . . . . ?
C10 C1 C2 Cl19 5.2(3) . . . . ?
C10 C1 C2 C3 -176.7(2) . . . . ?
C12 C8 C9 C10 -118.2(2) . . . . ?
C8 O7 C11 O18 -179.5(2) . . . . ?
C8 O7 C11 C10 1.6(2) . . . . ?
C8 C12 C13 C14 162.27(19) . . . . ?
C14 C20 C25 C24 -177.8(2) . . . . ?
C14 C20 C21 C22 176.5(2) . . . . ?
C11 O7 C8 C12 120.6(2) . . . . ?
C11 O7 C8 C9 -2.0(2) . . . . ?
C11 C10 C9 C8 -0.7(3) . . . . ?
C9 C10 C11 O7 -0.5(3) . . . . ?
C9 C10 C11 O18 -179.3(3) . . . . ?
C25 C20 C14 O15 -173.7(2) . . . . ?
C25 C20 C14 C13 5.2(3) . . . . ?
C25 C20 C21 C22 -0.6(4) . . . . ?
C25 C24 C23 C22 -1.6(4) . . . . ?
C6 C1 C10 C11 36.8(3) . . . . ?
C6 C1 C10 C9 -138.4(3) . . . . ?
C6 C1 C2 Cl19 -177.02(17) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C6 C5 C4 C3 1.2(4) . . . . ?
C13 C12 C8 O7 59.5(2) . . . . ?
C13 C12 C8 C9 175.96(19) . . . . ?
C16 C12 C8 O7 -64.1(2) . . . . ?
C16 C12 C8 C9 52.3(3) . . . . ?
C16 C12 C13 C14 -75.0(3) . . . . ?
C26 C31 C30 C29 -1.8(5) . . . . ?
C26 C27 C28 C29 0.8(5) . . . . ?
C21 C20 C14 O15 9.4(3) . . . . ?
C21 C20 C14 C13 -171.8(2) . . . . ?
C21 C20 C25 C24 -0.8(4) . . . . ?
C2 C1 C10 C11 -145.4(2) . . . . ?
C2 C1 C10 C9 39.4(4) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C17 C26 C31 C30 -178.0(3) . . . . ?
C17 C26 C27 C28 178.5(3) . . . . ?
C24 C23 C22 C21 0.2(4) . . . . ?
C31 C26 C27 C28 -1.2(5) . . . . ?
C30 C29 C28 C27 -0.8(5) . . . . ?
C27 C26 C31 C30 1.7(4) . . . . ?
C28 C29 C30 C31 1.3(5) . . . . ?

_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 3.642
_oxdiff_exptl_absorpt_empirical_full_min 0.655
####################################################################### 
# 
# 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_zhangmch_201103
_database_code_depnum_ccdc_archive 'CCDC 2101905'
loop_
_audit_author_name
_audit_author_address
'Yunyun chen'
;sysu
China
;
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2020-11-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H20 O3'
_chemical_formula_sum            'C27 H20 O3'
_chemical_formula_weight         392.43
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   23.3680(5)
_cell_length_b                   13.3744(3)
_cell_length_c                   12.7991(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.115(2)
_cell_angle_gamma                90
_cell_volume                     3984.21(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4615
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8920
_cell_measurement_theta_min      3.7780
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14734
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.816
_diffrn_reflns_theta_min         3.798
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  -5.00   0.50    0.10    --  -46.62  27.00 -66.00   54
  2  ω   -121.00 -32.00   0.50    0.10    --  -46.62 -27.00 130.00  178
  3  ω     58.00  88.00   0.50    0.10    --   46.62  27.00 -66.00   60
  4  ω    -18.00  60.00   0.50    0.10    --   46.62 -27.00 130.00  156
  5  ω   -174.00 -87.00   0.50    0.50    -- -100.00 -27.00 130.00  174
  6  ω   -106.00 -25.00   0.50    0.50    -- -100.00  27.00 -66.00  162
  7  ω     52.00  77.00   0.50    0.50    --  107.00 -27.00 130.00   50
  8  ω    101.00 134.00   0.50    0.50    --  107.00  27.00 -66.00   66
  9  ω    -14.00  27.00   0.50    0.10    --  -46.62  38.00 -60.00   82
 10  ω     33.00  95.00   0.50    0.10    --   46.62-125.00   0.00  124
 11  ω    -88.00 -30.00   0.50    0.50    -- -100.00  77.00 120.00  116
 12  ω   -122.00 -92.00   0.50    0.50    -- -100.00  77.00 120.00   60
 13  ω     34.00  89.00   0.50    0.50    --  107.00 -94.00 -60.00  110
 14  ω     37.00 123.00   0.50    0.50    --  107.00 -30.00 -60.00  172
 15  ω     94.00 175.00   0.50    0.50    --  107.00  61.00-120.00  162
 16  ω     32.00 123.00   0.50    0.50    --  107.00 -15.00 -90.00  182
 17  ω     73.00 103.00   0.50    0.50    --  107.00 -94.00 -30.00   60
 18  ω     83.00 108.00   0.50    0.50    --  107.00 -94.00-150.00   50
 19  ω     44.00 104.00   0.50    0.50    --  107.00 -94.00  90.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0214765000
_diffrn_orient_matrix_UB_12      -0.0344831000
_diffrn_orient_matrix_UB_13      0.1044966000
_diffrn_orient_matrix_UB_21      -0.0597188000
_diffrn_orient_matrix_UB_22      -0.0214343000
_diffrn_orient_matrix_UB_23      -0.0565252000
_diffrn_orient_matrix_UB_31      0.0187686000
_diffrn_orient_matrix_UB_32      -0.1078042000
_diffrn_orient_matrix_UB_33      -0.0221852000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3074
_reflns_number_total             4057
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00015(6)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+1.4726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1259
_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:
 C9(H9), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C6(H6), C2(H2), C16(H16), C5(H5), C14(H14), C18(H18), C24(H24),
 C17(H17), C3(H3), C15(H15), C20(H20), C4(H4), C23(H23), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O29 O 0.64553(5) 0.45471(9) 0.69619(10) 0.0315(3) Uani 1 1 d . . . . .
O30 O 0.69434(5) 0.31177(9) 0.69233(11) 0.0371(3) Uani 1 1 d . . . . .
O12 O 0.60182(6) 0.67200(10) 0.42215(10) 0.0383(3) Uani 1 1 d . . . . .
C27 C 0.58963(7) 0.31409(12) 0.65887(13) 0.0269(3) Uani 1 1 d . . . . .
C1 C 0.66835(7) 0.78903(12) 0.50039(14) 0.0288(4) Uani 1 1 d . . . . .
C26 C 0.55378(7) 0.39220(13) 0.66011(13) 0.0280(4) Uani 1 1 d . . . . .
H26 H 0.514019 0.388089 0.647842 0.034 Uiso 1 1 calc R U . . .
C19 C 0.57646(7) 0.20779(13) 0.63977(13) 0.0285(4) Uani 1 1 d . . . . .
C11 C 0.47473(7) 0.64544(12) 0.60372(14) 0.0296(4) Uani 1 1 d . . . . .
C9 C 0.57827(7) 0.56440(12) 0.59546(14) 0.0288(4) Uani 1 1 d . . . . .
H9 H 0.581080 0.530139 0.528431 0.035 Uiso 1 1 calc R U . . .
C28 C 0.64851(7) 0.35371(13) 0.68386(14) 0.0289(4) Uani 1 1 d . . . . .
C6 C 0.70578(7) 0.81729(13) 0.58655(14) 0.0300(4) Uani 1 1 d . . . . .
H6 H 0.705800 0.782403 0.649405 0.036 Uiso 1 1 calc R U . . .
C13 C 0.42239(7) 0.69958(13) 0.61450(13) 0.0291(4) Uani 1 1 d . . . . .
C2 C 0.66901(7) 0.84226(13) 0.40647(14) 0.0311(4) Uani 1 1 d . . . . .
H2 H 0.644129 0.824236 0.348774 0.037 Uiso 1 1 calc R U . . .
C8 C 0.62384(7) 0.64797(13) 0.60579(14) 0.0298(4) Uani 1 1 d . . . . .
H8A H 0.613735 0.695918 0.657958 0.036 Uiso 1 1 calc R U . . .
H8B H 0.660818 0.619297 0.629814 0.036 Uiso 1 1 calc R U . . .
C16 C 0.32308(8) 0.81020(14) 0.63422(15) 0.0345(4) Uani 1 1 d . . . . .
H16 H 0.289897 0.847322 0.640347 0.041 Uiso 1 1 calc R U . . .
C10 C 0.52040(7) 0.60664(12) 0.59549(14) 0.0297(4) Uani 1 1 d . . . . .
C7 C 0.62865(7) 0.70138(13) 0.50269(14) 0.0298(4) Uani 1 1 d . . . . .
C5 C 0.74295(7) 0.89739(13) 0.57849(15) 0.0338(4) Uani 1 1 d . . . . .
H5 H 0.767792 0.916010 0.636006 0.041 Uiso 1 1 calc R U . . .
C14 C 0.36849(7) 0.65522(13) 0.59518(14) 0.0314(4) Uani 1 1 d . . . . .
H14 H 0.365645 0.588296 0.575675 0.038 Uiso 1 1 calc R U . . .
C25 C 0.58632(7) 0.48660(13) 0.68382(14) 0.0292(4) Uani 1 1 d . . . . .
H25 H 0.575441 0.515454 0.749599 0.035 Uiso 1 1 calc R U . . .
C18 C 0.42586(7) 0.79983(13) 0.64515(14) 0.0323(4) Uani 1 1 d . . . . .
H18 H 0.461605 0.829833 0.659427 0.039 Uiso 1 1 calc R U . . .
C24 C 0.61980(8) 0.13722(13) 0.63022(14) 0.0325(4) Uani 1 1 d . . . . .
H24 H 0.657949 0.157736 0.633717 0.039 Uiso 1 1 calc R U . . .
C17 C 0.37643(8) 0.85459(14) 0.65436(15) 0.0349(4) Uani 1 1 d . . . . .
H17 H 0.379007 0.921462 0.674137 0.042 Uiso 1 1 calc R U . . .
C3 C 0.70635(8) 0.92142(13) 0.39883(15) 0.0338(4) Uani 1 1 d . . . . .
H3 H 0.706883 0.955905 0.335833 0.041 Uiso 1 1 calc R U . . .
C15 C 0.31906(8) 0.71076(14) 0.60500(15) 0.0351(4) Uani 1 1 d . . . . .
H15 H 0.283169 0.681000 0.591898 0.042 Uiso 1 1 calc R U . . .
C20 C 0.51934(8) 0.17505(14) 0.63192(15) 0.0346(4) Uani 1 1 d . . . . .
H20 H 0.489849 0.221228 0.635846 0.041 Uiso 1 1 calc R U . . .
C4 C 0.74314(8) 0.94964(13) 0.48509(16) 0.0354(4) Uani 1 1 d . . . . .
H4 H 0.767873 1.003572 0.480101 0.042 Uiso 1 1 calc R U . . .
C23 C 0.60646(9) 0.03710(14) 0.61561(15) 0.0384(4) Uani 1 1 d . . . . .
H23 H 0.635590 -0.009177 0.608717 0.046 Uiso 1 1 calc R U . . .
C21 C 0.50634(9) 0.07510(15) 0.61843(16) 0.0412(4) Uani 1 1 d . . . . .
H21 H 0.468260 0.054096 0.614156 0.049 Uiso 1 1 calc R U . . .
C22 C 0.55000(9) 0.00576(14) 0.61123(16) 0.0417(5) Uani 1 1 d . . . . .
H22 H 0.541233 -0.061805 0.603456 0.050 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
O29 C28 1.362(2) . ?
O29 C25 1.4431(19) . ?
O30 C28 1.205(2) . ?
O12 C7 1.223(2) . ?
C27 C26 1.340(2) . ?
C27 C19 1.470(2) . ?
C27 C28 1.483(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.398(3) . ?
C1 C7 1.497(2) . ?
C26 H26 0.9300 . ?
C26 C25 1.491(2) . ?
C19 C24 1.398(2) . ?
C19 C20 1.400(2) . ?
C11 C13 1.439(2) . ?
C11 C10 1.200(2) . ?
C9 H9 0.9800 . ?
C9 C8 1.541(2) . ?
C9 C10 1.466(2) . ?
C9 C25 1.536(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.389(3) . ?
C13 C14 1.394(2) . ?
C13 C18 1.397(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.513(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(3) . ?
C16 C15 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.385(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(3) . ?
C25 H25 0.9800 . ?
C18 H18 0.9300 . ?
C18 C17 1.382(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.384(3) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C15 H15 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.378(3) . ?
C4 H4 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(3) . ?
C22 H22 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
C28 O29 C25 109.80(12) . . ?
C26 C27 C19 129.34(15) . . ?
C26 C27 C28 106.74(15) . . ?
C19 C27 C28 123.91(14) . . ?
C6 C1 C2 119.13(16) . . ?
C6 C1 C7 122.81(16) . . ?
C2 C1 C7 118.03(15) . . ?
C27 C26 H26 124.6 . . ?
C27 C26 C25 110.77(14) . . ?
C25 C26 H26 124.6 . . ?
C24 C19 C27 121.67(15) . . ?
C24 C19 C20 118.44(16) . . ?
C20 C19 C27 119.89(15) . . ?
C10 C11 C13 175.36(18) . . ?
C8 C9 H9 108.3 . . ?
C10 C9 H9 108.3 . . ?
C10 C9 C8 110.55(14) . . ?
C10 C9 C25 108.26(14) . . ?
C25 C9 H9 108.3 . . ?
C25 C9 C8 112.94(14) . . ?
O29 C28 C27 108.86(13) . . ?
O30 C28 O29 120.35(15) . . ?
O30 C28 C27 130.79(16) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.11(17) . . ?
C5 C6 H6 119.9 . . ?
C14 C13 C11 122.08(16) . . ?
C14 C13 C18 119.14(15) . . ?
C18 C13 C11 118.77(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.44(17) . . ?
C3 C2 H2 119.8 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 C9 111.83(14) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.09(16) . . ?
C11 C10 C9 174.13(18) . . ?
O12 C7 C1 120.48(16) . . ?
O12 C7 C8 120.74(16) . . ?
C1 C7 C8 118.75(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.23(17) . . ?
C4 C5 H5 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.13(17) . . ?
C15 C14 H14 119.9 . . ?
O29 C25 C26 103.80(13) . . ?
O29 C25 C9 109.53(13) . . ?
O29 C25 H25 110.0 . . ?
C26 C25 C9 113.39(14) . . ?
C26 C25 H25 110.0 . . ?
C9 C25 H25 110.0 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.30(16) . . ?
C17 C18 H18 119.8 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.60(17) . . ?
C23 C24 H24 119.7 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.18(17) . . ?
C18 C17 H17 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.14(17) . . ?
C4 C3 H3 119.9 . . ?
C16 C15 C14 120.14(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.69(17) . . ?
C21 C20 H20 119.7 . . ?
C5 C4 C3 119.95(17) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C24 C23 H23 119.9 . . ?
C22 C23 C24 120.14(18) . . ?
C22 C23 H23 119.9 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.08(18) . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.00(18) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?

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
C27 C26 C25 O29 0.09(19) . . . . ?
C27 C26 C25 C9 118.87(16) . . . . ?
C27 C19 C24 C23 177.92(16) . . . . ?
C27 C19 C20 C21 -177.26(17) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C26 C27 C19 C24 172.97(18) . . . . ?
C26 C27 C19 C20 -7.8(3) . . . . ?
C26 C27 C28 O29 -1.67(19) . . . . ?
C26 C27 C28 O30 179.42(19) . . . . ?
C19 C27 C26 C25 179.53(16) . . . . ?
C19 C27 C28 O29 179.62(15) . . . . ?
C19 C27 C28 O30 0.7(3) . . . . ?
C19 C24 C23 C22 -0.6(3) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C11 C13 C14 C15 -179.01(17) . . . . ?
C11 C13 C18 C17 178.78(17) . . . . ?
C9 C8 C7 O12 -5.8(2) . . . . ?
C9 C8 C7 C1 176.18(14) . . . . ?
C28 O29 C25 C26 -1.17(18) . . . . ?
C28 O29 C25 C9 -122.56(15) . . . . ?
C28 C27 C26 C25 0.91(19) . . . . ?
C28 C27 C19 C24 -8.6(3) . . . . ?
C28 C27 C19 C20 170.65(16) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C6 C1 C7 O12 -171.02(16) . . . . ?
C6 C1 C7 C8 7.0(2) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C13 C18 C17 C16 0.6(3) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C1 C7 O12 6.8(2) . . . . ?
C2 C1 C7 C8 -175.16(15) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C8 C9 C25 O29 -48.62(19) . . . . ?
C8 C9 C25 C26 -164.04(14) . . . . ?
C10 C9 C8 C7 -78.59(18) . . . . ?
C10 C9 C25 O29 -171.37(13) . . . . ?
C10 C9 C25 C26 73.21(18) . . . . ?
C7 C1 C6 C5 177.88(16) . . . . ?
C7 C1 C2 C3 -177.56(15) . . . . ?
C14 C13 C18 C17 -1.1(3) . . . . ?
C25 O29 C28 O30 -179.20(16) . . . . ?
C25 O29 C28 C27 1.75(18) . . . . ?
C25 C9 C8 C7 159.94(14) . . . . ?
C18 C13 C14 C15 0.9(3) . . . . ?
C24 C19 C20 C21 2.0(3) . . . . ?
C24 C23 C22 C21 1.9(3) . . . . ?
C17 C16 C15 C14 -0.4(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C20 C19 C24 C23 -1.4(3) . . . . ?
C20 C21 C22 C23 -1.2(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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.895
####################################################################### 
# 
# 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_zhangmch_02_200821
_database_code_depnum_ccdc_archive 'CCDC 2104320'
loop_
_audit_author_name
_audit_author_address
'Yunyun chen'
;sysu
China
;
_audit_update_record             
;
2021-08-19 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_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         'C25 H19 N O5'
_chemical_formula_sum            'C25 H19 N O5'
_chemical_formula_weight         413.41
_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'
N N 0.0311 0.0180 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6080(3)
_cell_length_b                   10.7491(3)
_cell_length_c                   13.6882(4)
_cell_angle_alpha                104.255(2)
_cell_angle_beta                 103.185(3)
_cell_angle_gamma                102.624(3)
_cell_volume                     1010.58(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6091
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.7540
_cell_measurement_theta_min      4.6890
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11939
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.086
_diffrn_reflns_theta_min         4.714
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -82.00   0.50    0.05    --  -46.62-163.00-132.00   50
  2  ω    -74.00 -38.00   0.50    0.05    --  -46.62 116.00 104.00   72
  3  ω     41.00  89.00   0.50    0.05    --   46.62-116.00  16.00   96
  4  ω     77.00 107.00   0.50    0.05    --   46.62-163.00-132.00   60
  5  ω     51.00 103.00   0.50    0.05    --   46.62 163.00-107.00  104
  6  ω   -138.00-112.00   0.50    0.10    -- -100.00-116.00  16.00   52
  7  ω   -111.00 -48.00   0.50    0.10    -- -100.00 116.00 104.00  126
  8  ω    -87.00 -48.00   0.50    0.10    -- -100.00 163.00-107.00   78
  9  ω   -130.00 -92.00   0.50    0.10    -- -100.00 163.00-107.00   76
 10  ω   -128.00-103.00   0.50    0.10    -- -100.00-163.00-132.00   50
 11  ω     91.00 117.00   0.50    0.10    --  105.44 163.00-107.00   52
 12  ω     98.00 124.00   0.50    0.10    --  105.44 116.00 104.00   52
 13  ω     91.00 142.00   0.50    0.10    --  105.44-163.00-132.00  102
 14  ω     34.00 109.00   0.50    0.10    --  105.44-116.00  16.00  150
 15  ω    -79.00 -54.00   0.50    0.05    --  -46.62 163.00-107.00   50
 16  ω   -117.00 -82.00   0.50    0.05    --  -46.62-125.00  60.00   70
 17  ω   -119.00 -25.00   0.50    0.05    --  -46.62 -77.00   0.00  188
 18  ω   -119.00 -90.00   0.50    0.05    --  -46.62-125.00 150.00   58
 19  ω   -119.00 -73.00   0.50    0.05    --  -46.62-125.00 -30.00   92
 20  ω   -118.00 -76.00   0.50    0.05    --  -46.62-125.00-180.00   84
 21  ω     89.00 120.00   0.50    0.05    --   46.62  38.00 -30.00   62
 22  ω   -120.00 -82.00   0.50    0.10    -- -100.00 -61.00 -60.00   76
 23  ω   -162.00-130.00   0.50    0.10    -- -100.00 -61.00 -60.00   64
 24  ω   -108.00 -82.00   0.50    0.10    -- -100.00 -61.00  90.00   52
 25  ω    -70.00 -27.00   0.50    0.10    -- -100.00  61.00 -60.00   86
 26  ω   -117.00 -78.00   0.50    0.10    -- -100.00  61.00 -60.00   78
 27  ω   -172.00-125.00   0.50    0.10    -- -100.00 -61.00  90.00   94
 28  ω    -98.00 -29.00   0.50    0.10    -- -100.00  61.00 120.00  138
 29  ω     90.00 150.00   0.50    0.10    --  105.44 125.00  60.00  120
 30  ω     31.00 121.00   0.50    0.10    --  105.44 -30.00  90.00  180
 31  ω     34.00 120.00   0.50    0.10    --  105.44 -45.00 -30.00  172
 32  ω    117.00 176.00   0.50    0.10    --  105.44  30.00-120.00  118
 33  ω     42.00  97.00   0.50    0.10    --  105.44 -30.00 -60.00  110
 34  ω     33.00  93.00   0.50    0.10    --  105.44 -94.00-150.00  120
 35  ω     71.00 105.00   0.50    0.10    --  105.44 -94.00-120.00   68
 36  ω     60.00 120.00   0.50    0.10    --  105.44 -45.00 150.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1861286000
_diffrn_orient_matrix_UB_12      -0.1122894000
_diffrn_orient_matrix_UB_13      -0.0604616000
_diffrn_orient_matrix_UB_21      0.0500163000
_diffrn_orient_matrix_UB_22      -0.0095763000
_diffrn_orient_matrix_UB_23      -0.1039826000
_diffrn_orient_matrix_UB_31      0.1005686000
_diffrn_orient_matrix_UB_32      -0.1057869000
_diffrn_orient_matrix_UB_33      0.0181983000
_diffrn_oxdiff_digest_frames     
;
01dd42b14ffe357d95f4bc33780d1d7e3e00050666e
;
_diffrn_oxdiff_digest_hkl        
;
015f89d9fab975cdedb965be2bc635ba21b1d5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3357
_reflns_number_total             4008
_reflns_odcompleteness_completeness 99.67
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0021(5)
_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   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.099
_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)+(0.0564P)²+0.2797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1224
_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:
 C21(H21), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C22(H22), C5(H5), C30(H30), C6(H6), C3(H3), C15(H15), C26(H26),
 C29(H29), C28(H28), C27(H27), C19(H19), C18(H18), C17(H17), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O20 O -0.45618(13) -0.25870(10) -0.47107(8) 0.0247(2) Uani 1 1 d . . . . .
O31 O -0.76594(14) -0.31263(11) -0.55000(9) 0.0314(3) Uani 1 1 d . . . . .
O10 O 0.12252(15) -0.11571(11) -0.33736(9) 0.0329(3) Uani 1 1 d . . . . .
O13 O -0.74474(19) -0.76545(12) -0.91404(10) 0.0427(3) Uani 1 1 d . . . . .
O12 O -0.69379(19) -0.60911(14) -0.98703(9) 0.0486(4) Uani 1 1 d . . . . .
N11 N -0.66672(19) -0.65142(14) -0.91055(10) 0.0322(3) Uani 1 1 d . . . . .
C25 C -0.6610(2) -0.11878(14) -0.67887(11) 0.0242(3) Uani 1 1 d . . . . .
C1 C -0.28953(19) -0.38006(14) -0.62044(11) 0.0237(3) Uani 1 1 d . . . . .
C23 C -0.5396(2) -0.15346(14) -0.59569(11) 0.0244(3) Uani 1 1 d . . . . .
C14 C 0.1087(2) -0.26325(16) -0.23505(12) 0.0278(3) Uani 1 1 d . . . . .
C9 C 0.0516(2) -0.22720(15) -0.33388(12) 0.0265(3) Uani 1 1 d . . . . .
C2 C -0.3890(2) -0.50780(15) -0.62562(11) 0.0259(3) Uani 1 1 d . . . . .
H2 H -0.372986 -0.533074 -0.564653 0.031 Uiso 1 1 calc R . . . .
C24 C -0.6080(2) -0.24901(14) -0.54109(11) 0.0248(3) Uani 1 1 d . . . . .
C8 C -0.0964(2) -0.33186(15) -0.42920(11) 0.0248(3) Uani 1 1 d . . . . .
H8A H -0.201684 -0.372217 -0.407326 0.030 Uiso 1 1 calc R . . . .
H8B H -0.043112 -0.402034 -0.457008 0.030 Uiso 1 1 calc R . . . .
C21 C -0.2839(2) -0.17896(14) -0.47967(12) 0.0244(3) Uani 1 1 d . . . . .
H21 H -0.209918 -0.112548 -0.411113 0.029 Uiso 1 1 calc R . . . .
C7 C -0.1690(2) -0.27443(14) -0.51656(11) 0.0238(3) Uani 1 1 d . . . . .
H7 H -0.059410 -0.221312 -0.529415 0.029 Uiso 1 1 calc R . . . .
C22 C -0.3512(2) -0.11056(14) -0.55608(12) 0.0254(3) Uani 1 1 d . . . . .
H22 H -0.272889 -0.046299 -0.574170 0.030 Uiso 1 1 calc R . . . .
C5 C -0.4358(2) -0.43332(16) -0.80879(12) 0.0296(3) Uani 1 1 d . . . . .
H5 H -0.451194 -0.409024 -0.870193 0.036 Uiso 1 1 calc R . . . .
C30 C -0.5819(2) -0.01832(15) -0.71726(12) 0.0278(3) Uani 1 1 d . . . . .
H30 H -0.453738 0.027035 -0.689009 0.033 Uiso 1 1 calc R . . . .
C6 C -0.3134(2) -0.34543(16) -0.71361(12) 0.0271(3) Uani 1 1 d . . . . .
H6 H -0.245180 -0.261196 -0.711530 0.033 Uiso 1 1 calc R . . . .
C4 C -0.5346(2) -0.55806(15) -0.81010(11) 0.0271(3) Uani 1 1 d . . . . .
C3 C -0.5120(2) -0.59814(15) -0.72037(12) 0.0274(3) Uani 1 1 d . . . . .
H3 H -0.577544 -0.683596 -0.723530 0.033 Uiso 1 1 calc R . . . .
C15 C 0.0382(2) -0.39097(17) -0.22871(12) 0.0311(3) Uani 1 1 d . . . . .
H15 H -0.046119 -0.458152 -0.288122 0.037 Uiso 1 1 calc R . . . .
C26 C -0.8533(2) -0.18638(16) -0.72337(12) 0.0313(3) Uani 1 1 d . . . . .
H26 H -0.908764 -0.254094 -0.699239 0.038 Uiso 1 1 calc R . . . .
C29 C -0.6917(2) 0.01487(16) -0.79704(12) 0.0307(3) Uani 1 1 d . . . . .
H29 H -0.637084 0.082482 -0.821537 0.037 Uiso 1 1 calc R . . . .
C28 C -0.8831(2) -0.05252(17) -0.84047(12) 0.0334(4) Uani 1 1 d . . . . .
H28 H -0.956940 -0.030151 -0.893797 0.040 Uiso 1 1 calc R . . . .
C27 C -0.9623(2) -0.15267(18) -0.80385(13) 0.0365(4) Uani 1 1 d . . . . .
H27 H -1.090152 -0.198457 -0.833156 0.044 Uiso 1 1 calc R . . . .
C19 C 0.2370(2) -0.16353(18) -0.14535(13) 0.0344(4) Uani 1 1 d . . . . .
H19 H 0.285410 -0.077866 -0.148581 0.041 Uiso 1 1 calc R . . . .
C18 C 0.2920(3) -0.1922(2) -0.05161(13) 0.0409(4) Uani 1 1 d . . . . .
H18 H 0.378183 -0.125896 0.007688 0.049 Uiso 1 1 calc R . . . .
C17 C 0.2193(3) -0.3187(2) -0.04596(13) 0.0413(4) Uani 1 1 d . . . . .
H17 H 0.255356 -0.336835 0.017446 0.050 Uiso 1 1 calc R . . . .
C16 C 0.0928(2) -0.41898(19) -0.13438(13) 0.0376(4) Uani 1 1 d . . . . .
H16 H 0.044822 -0.504383 -0.130537 0.045 Uiso 1 1 calc R . . . .


_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
O20 C24 1.3637(17) . ?
O20 C21 1.4478(17) . ?
O31 C24 1.2082(18) . ?
O10 C9 1.2193(18) . ?
O13 N11 1.2235(18) . ?
O12 N11 1.2338(17) . ?
N11 C4 1.469(2) . ?
C25 C23 1.472(2) . ?
C25 C30 1.394(2) . ?
C25 C26 1.396(2) . ?
C1 C2 1.392(2) . ?
C1 C7 1.519(2) . ?
C1 C6 1.398(2) . ?
C23 C24 1.485(2) . ?
C23 C22 1.340(2) . ?
C14 C9 1.494(2) . ?
C14 C15 1.392(2) . ?
C14 C19 1.399(2) . ?
C9 C8 1.513(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.5256(19) . ?
C21 H21 0.9800 . ?
C21 C7 1.552(2) . ?
C21 C22 1.482(2) . ?
C7 H7 0.9800 . ?
C22 H22 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.383(2) . ?
C5 C4 1.380(2) . ?
C30 H30 0.9300 . ?
C30 C29 1.387(2) . ?
C6 H6 0.9300 . ?
C4 C3 1.386(2) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.394(2) . ?
C29 H29 0.9300 . ?
C29 C28 1.389(2) . ?
C28 H28 0.9300 . ?
C28 C27 1.376(2) . ?
C27 H27 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.387(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.379(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.388(3) . ?
C16 H16 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
C24 O20 C21 109.67(11) . . ?
O13 N11 O12 123.62(14) . . ?
O13 N11 C4 118.92(12) . . ?
O12 N11 C4 117.45(14) . . ?
C30 C25 C23 119.50(13) . . ?
C30 C25 C26 118.46(14) . . ?
C26 C25 C23 122.01(13) . . ?
C2 C1 C7 122.32(12) . . ?
C2 C1 C6 118.35(14) . . ?
C6 C1 C7 119.16(13) . . ?
C25 C23 C24 124.96(13) . . ?
C22 C23 C25 128.46(14) . . ?
C22 C23 C24 106.57(13) . . ?
C15 C14 C9 122.70(14) . . ?
C15 C14 C19 119.09(14) . . ?
C19 C14 C9 118.21(14) . . ?
O10 C9 C14 120.62(14) . . ?
O10 C9 C8 120.84(13) . . ?
C14 C9 C8 118.54(13) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.07(13) . . ?
C3 C2 H2 119.5 . . ?
O20 C24 C23 108.67(12) . . ?
O31 C24 O20 120.46(13) . . ?
O31 C24 C23 130.86(13) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C9 C8 C7 112.93(12) . . ?
H8A C8 H8B 107.8 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
O20 C21 H21 110.0 . . ?
O20 C21 C7 108.34(11) . . ?
O20 C21 C22 103.71(11) . . ?
C7 C21 H21 110.0 . . ?
C22 C21 H21 110.0 . . ?
C22 C21 C7 114.46(12) . . ?
C1 C7 C8 114.08(12) . . ?
C1 C7 C21 109.07(11) . . ?
C1 C7 H7 107.9 . . ?
C8 C7 C21 109.87(11) . . ?
C8 C7 H7 107.9 . . ?
C21 C7 H7 107.9 . . ?
C23 C22 C21 111.11(13) . . ?
C23 C22 H22 124.4 . . ?
C21 C22 H22 124.4 . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.15(14) . . ?
C25 C30 H30 119.6 . . ?
C29 C30 C25 120.88(14) . . ?
C29 C30 H30 119.6 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.65(14) . . ?
C5 C6 H6 119.2 . . ?
C5 C4 N11 118.53(13) . . ?
C5 C4 C3 122.26(14) . . ?
C3 C4 N11 119.21(14) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.49(14) . . ?
C4 C3 H3 120.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.59(15) . . ?
C16 C15 H15 119.7 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.21(15) . . ?
C27 C26 H26 119.9 . . ?
C30 C29 H29 119.9 . . ?
C30 C29 C28 120.23(15) . . ?
C28 C29 H29 119.9 . . ?
C29 C28 H28 120.3 . . ?
C27 C28 C29 119.39(15) . . ?
C27 C28 H28 120.3 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.82(15) . . ?
C28 C27 H27 119.6 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.11(16) . . ?
C18 C19 H19 119.9 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.26(16) . . ?
C17 C18 H18 119.9 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.37(16) . . ?
C16 C17 H17 119.8 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.58(17) . . ?
C17 C16 H16 120.2 . . ?

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
O20 C21 C7 C1 57.19(14) . . . . ?
O20 C21 C7 C8 -68.53(14) . . . . ?
O20 C21 C22 C23 -5.16(16) . . . . ?
O10 C9 C8 C7 -11.05(19) . . . . ?
O13 N11 C4 C5 174.86(14) . . . . ?
O13 N11 C4 C3 -4.6(2) . . . . ?
O12 N11 C4 C5 -5.7(2) . . . . ?
O12 N11 C4 C3 174.81(14) . . . . ?
N11 C4 C3 C2 -178.85(13) . . . . ?
C25 C23 C24 O20 178.49(12) . . . . ?
C25 C23 C24 O31 -1.7(2) . . . . ?
C25 C23 C22 C21 -175.15(14) . . . . ?
C25 C30 C29 C28 -0.4(2) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C23 C25 C30 C29 178.73(13) . . . . ?
C23 C25 C26 C27 -178.38(14) . . . . ?
C14 C9 C8 C7 168.74(12) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C14 C19 C18 C17 -0.6(3) . . . . ?
C9 C14 C15 C16 -178.72(14) . . . . ?
C9 C14 C19 C18 179.19(14) . . . . ?
C9 C8 C7 C1 169.22(11) . . . . ?
C9 C8 C7 C21 -67.96(15) . . . . ?
C2 C1 C7 C8 25.36(19) . . . . ?
C2 C1 C7 C21 -97.88(15) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C24 O20 C21 C7 -116.96(12) . . . . ?
C24 O20 C21 C22 5.03(14) . . . . ?
C24 C23 C22 C21 3.28(16) . . . . ?
C21 O20 C24 O31 176.87(13) . . . . ?
C21 O20 C24 C23 -3.31(15) . . . . ?
C7 C1 C2 C3 173.91(13) . . . . ?
C7 C1 C6 C5 -173.64(13) . . . . ?
C7 C21 C22 C23 112.66(14) . . . . ?
C22 C23 C24 O20 -0.01(16) . . . . ?
C22 C23 C24 O31 179.78(15) . . . . ?
C22 C21 C7 C1 -57.96(15) . . . . ?
C22 C21 C7 C8 176.31(12) . . . . ?
C5 C4 C3 C2 1.7(2) . . . . ?
C30 C25 C23 C24 174.09(13) . . . . ?
C30 C25 C23 C22 -7.7(2) . . . . ?
C30 C25 C26 C27 -0.4(2) . . . . ?
C30 C29 C28 C27 -0.2(2) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
C6 C1 C7 C8 -159.54(13) . . . . ?
C6 C1 C7 C21 77.21(15) . . . . ?
C6 C5 C4 N11 179.26(13) . . . . ?
C6 C5 C4 C3 -1.3(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C15 C14 C9 O10 -176.98(14) . . . . ?
C15 C14 C9 C8 3.2(2) . . . . ?
C15 C14 C19 C18 -0.2(2) . . . . ?
C26 C25 C23 C24 -7.9(2) . . . . ?
C26 C25 C23 C22 170.24(15) . . . . ?
C26 C25 C30 C29 0.7(2) . . . . ?
C29 C28 C27 C26 0.5(3) . . . . ?
C19 C14 C9 O10 3.7(2) . . . . ?
C19 C14 C9 C8 -176.12(13) . . . . ?
C19 C14 C15 C16 0.6(2) . . . . ?
C19 C18 C17 C16 1.0(3) . . . . ?
C18 C17 C16 C15 -0.5(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 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.828
