# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_181010_s2_yc
_database_code_depnum_ccdc_archive 'CCDC 1949886'
loop_
_audit_author_name
_audit_author_address
haotaotao
;Si Chuan University
China
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 O'
_chemical_formula_sum            'C23 H24 O'
_chemical_formula_weight         316.42
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.0783(3)
_cell_length_b                   7.9438(4)
_cell_length_c                   36.1259(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1744.33(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1900
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5860
_cell_measurement_theta_min      4.0320
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            9136
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.072
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  71.10   0.30    1.50    --   16.69  57.00   0.00  237
  2  ω      1.00  37.90   0.30    1.50    --   16.69  57.00-150.00  123
  3  ω     44.00  78.80   0.30    1.50    --   16.69  57.00-150.00  116
  4  ω    -25.00   0.20   0.30    1.50    --  -14.97 -99.00 -90.00   84
  5  ω     21.00  45.90   0.30    1.50    --   16.69-144.00 -10.00   83
  6  ω     23.00  47.90   0.30    1.50    --   16.69-126.00 158.00   83
  7  ω    -76.00 -51.70   0.30    1.50    --  -14.97 -57.00 120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0077843000
_diffrn_orient_matrix_UB_12      -0.0253592000
_diffrn_orient_matrix_UB_13      -0.0187751000
_diffrn_orient_matrix_UB_21      0.0005370000
_diffrn_orient_matrix_UB_22      0.0855749000
_diffrn_orient_matrix_UB_23      -0.0055961000
_diffrn_orient_matrix_UB_31      0.1164738000
_diffrn_orient_matrix_UB_32      -0.0020989000
_diffrn_orient_matrix_UB_33      -0.0012286000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2656
_reflns_number_total             3468
_reflns_odcompleteness_completeness 99.58
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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         0.140
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 796 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.047
_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)+(0.0540P)²+0.0192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1167
_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:
 C7(H7), C8(H8), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C)
;
_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
O1 O 0.1024(4) -0.0151(3) 0.47924(5) 0.0607(6) Uani 1 1 d . . . . .
C1 C 0.0903(5) 0.1258(4) 0.45736(7) 0.0473(7) Uani 1 1 d . . . . .
C2 C -0.0614(5) 0.2533(4) 0.46171(7) 0.0574(8) Uani 1 1 d . . . . .
H2 H -0.1645 0.2487 0.4807 0.069 Uiso 1 1 calc R . . . .
C3 C -0.0583(5) 0.3885(4) 0.43740(8) 0.0624(8) Uani 1 1 d . . . . .
H3 H -0.1601 0.4748 0.4405 0.075 Uiso 1 1 calc R . . . .
C4 C 0.0900(5) 0.3987(4) 0.40904(8) 0.0570(8) Uani 1 1 d . . . . .
H4 H 0.0874 0.4895 0.3928 0.068 Uiso 1 1 calc R . . . .
C5 C 0.2452(4) 0.2708(3) 0.40482(7) 0.0449(6) Uani 1 1 d . . . . .
C6 C 0.4202(4) 0.2500(3) 0.37694(7) 0.0434(6) Uani 1 1 d . . . . .
C7 C 0.5503(4) 0.0933(3) 0.38700(7) 0.0408(6) Uani 1 1 d . . . . .
H7 H 0.7034 0.1213 0.3929 0.049 Uiso 1 1 calc R . . . .
C8 C 0.5377(5) -0.0497(3) 0.35828(7) 0.0464(7) Uani 1 1 d . . . . .
H8 H 0.5578 -0.0138 0.3326 0.056 Uiso 1 1 calc R . . . .
C9 C 0.6901(5) -0.1926(4) 0.37068(9) 0.0616(9) Uani 1 1 d . . . . .
H9A H 0.8343 -0.1499 0.3774 0.074 Uiso 1 1 calc R . . . .
H9B H 0.7065 -0.2764 0.3513 0.074 Uiso 1 1 calc R . . . .
C10 C 0.5707(5) -0.2665(4) 0.40468(8) 0.0559(7) Uani 1 1 d . . . . .
H10A H 0.5353 -0.3843 0.4009 0.067 Uiso 1 1 calc R . . . .
H10B H 0.6598 -0.2556 0.4268 0.067 Uiso 1 1 calc R . . . .
C11 C 0.3621(4) -0.1602(3) 0.40749(7) 0.0440(6) Uani 1 1 d . . . . .
H11 H 0.2416 -0.2123 0.4214 0.053 Uiso 1 1 calc R . . . .
C12 C 0.4308(4) 0.0159(3) 0.42123(7) 0.0409(6) Uani 1 1 d . . . . .
H12 H 0.5310 0.0073 0.4424 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2474(4) 0.1363(3) 0.42920(7) 0.0413(6) Uani 1 1 d . . . . .
C14 C 0.3115(4) -0.1245(4) 0.36687(7) 0.0498(7) Uani 1 1 d . . . . .
H14A H 0.1931 -0.0440 0.3637 0.060 Uiso 1 1 calc R . . . .
H14B H 0.2813 -0.2260 0.3528 0.060 Uiso 1 1 calc R . . . .
C15 C -0.0701(6) -0.0423(5) 0.50528(8) 0.0758(10) Uani 1 1 d . . . . .
H15A H -0.2093 -0.0393 0.4927 0.114 Uiso 1 1 calc GR . . . .
H15B H -0.0662 0.0442 0.5238 0.114 Uiso 1 1 calc GR . . . .
H15C H -0.0511 -0.1502 0.5168 0.114 Uiso 1 1 calc GR . . . .
C16 C 0.4439(5) 0.3498(4) 0.34699(7) 0.0516(7) Uani 1 1 d . . . . .
H16 H 0.3444 0.4384 0.3454 0.062 Uiso 1 1 calc R . . . .
C17 C 0.6023(5) 0.3396(4) 0.31668(7) 0.0510(7) Uani 1 1 d . . . . .
C18 C 0.8117(5) 0.2709(4) 0.31943(8) 0.0580(8) Uani 1 1 d . . . . .
H18 H 0.8614 0.2333 0.3423 0.070 Uiso 1 1 calc R . . . .
C19 C 0.9473(5) 0.2569(4) 0.28920(8) 0.0630(8) Uani 1 1 d . . . . .
H19 H 1.0863 0.2099 0.2922 0.076 Uiso 1 1 calc R . . . .
C20 C 0.8841(5) 0.3100(5) 0.25463(8) 0.0628(9) Uani 1 1 d . . . . .
C21 C 0.6792(6) 0.3846(5) 0.25169(9) 0.0738(10) Uani 1 1 d . . . . .
H21 H 0.6327 0.4247 0.2288 0.089 Uiso 1 1 calc R . . . .
C22 C 0.5422(5) 0.4011(5) 0.28190(9) 0.0684(9) Uani 1 1 d . . . . .
H22 H 0.4070 0.4544 0.2791 0.082 Uiso 1 1 calc R . . . .
C23 C 1.0327(6) 0.2888(6) 0.22129(9) 0.0884(12) Uani 1 1 d . . . . .
H23A H 1.1795 0.3227 0.2276 0.133 Uiso 1 1 calc GR . . . .
H23B H 0.9795 0.3574 0.2013 0.133 Uiso 1 1 calc GR . . . .
H23C H 1.0332 0.1729 0.2138 0.133 Uiso 1 1 calc GR . . . .


_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 C1 1.372(3) . ?
O1 C15 1.425(3) . ?
C1 C2 1.379(4) . ?
C1 C13 1.398(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.367(4) . ?
C4 C5 1.395(4) . ?
C5 C6 1.474(4) . ?
C5 C13 1.385(4) . ?
C6 C7 1.519(4) . ?
C6 C16 1.349(3) . ?
C7 C8 1.540(4) . ?
C7 C12 1.561(3) . ?
C8 C9 1.532(4) . ?
C8 C14 1.529(4) . ?
C9 C10 1.543(4) . ?
C10 C11 1.527(4) . ?
C11 C12 1.542(4) . ?
C11 C14 1.526(4) . ?
C12 C13 1.497(3) . ?
C16 C17 1.460(4) . ?
C17 C18 1.389(4) . ?
C17 C22 1.397(4) . ?
C18 C19 1.372(4) . ?
C19 C20 1.373(4) . ?
C20 C21 1.384(5) . ?
C20 C23 1.515(4) . ?
C21 C22 1.379(4) . ?

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 O1 C15 117.7(2) . . ?
O1 C1 C2 124.7(2) . . ?
O1 C1 C13 115.6(2) . . ?
C2 C1 C13 119.8(3) . . ?
C1 C2 C3 119.2(3) . . ?
C4 C3 C2 122.0(3) . . ?
C3 C4 C5 119.0(3) . . ?
C4 C5 C6 130.1(3) . . ?
C13 C5 C4 119.9(2) . . ?
C13 C5 C6 110.0(2) . . ?
C5 C6 C7 107.7(2) . . ?
C16 C6 C5 124.0(3) . . ?
C16 C6 C7 128.1(2) . . ?
C6 C7 C8 114.7(2) . . ?
C6 C7 C12 105.7(2) . . ?
C8 C7 C12 102.71(19) . . ?
C9 C8 C7 108.6(2) . . ?
C14 C8 C7 101.2(2) . . ?
C14 C8 C9 101.3(2) . . ?
C8 C9 C10 103.3(2) . . ?
C11 C10 C9 103.5(2) . . ?
C10 C11 C12 107.3(2) . . ?
C14 C11 C10 101.9(2) . . ?
C14 C11 C12 101.3(2) . . ?
C11 C12 C7 103.20(19) . . ?
C13 C12 C7 104.3(2) . . ?
C13 C12 C11 116.1(2) . . ?
C1 C13 C12 127.6(2) . . ?
C5 C13 C1 120.1(2) . . ?
C5 C13 C12 112.2(2) . . ?
C11 C14 C8 94.9(2) . . ?
C6 C16 C17 129.7(3) . . ?
C18 C17 C16 124.9(2) . . ?
C18 C17 C22 116.2(3) . . ?
C22 C17 C16 118.9(3) . . ?
C19 C18 C17 121.7(3) . . ?
C18 C19 C20 122.1(3) . . ?
C19 C20 C21 117.0(3) . . ?
C19 C20 C23 121.5(3) . . ?
C21 C20 C23 121.6(3) . . ?
C22 C21 C20 121.6(3) . . ?
C21 C22 C17 121.4(3) . . ?

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
O1 C1 C2 C3 -179.2(3) . . . . ?
O1 C1 C13 C5 177.9(2) . . . . ?
O1 C1 C13 C12 -2.6(4) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C1 C13 C5 -2.6(4) . . . . ?
C2 C1 C13 C12 176.8(3) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C3 C4 C5 C6 179.5(3) . . . . ?
C3 C4 C5 C13 -0.1(4) . . . . ?
C4 C5 C6 C7 176.4(3) . . . . ?
C4 C5 C6 C16 -7.6(4) . . . . ?
C4 C5 C13 C1 1.9(4) . . . . ?
C4 C5 C13 C12 -177.6(2) . . . . ?
C5 C6 C7 C8 116.0(2) . . . . ?
C5 C6 C7 C12 3.7(2) . . . . ?
C5 C6 C16 C17 -177.2(3) . . . . ?
C6 C5 C13 C1 -177.7(2) . . . . ?
C6 C5 C13 C12 2.7(3) . . . . ?
C6 C7 C8 C9 175.6(2) . . . . ?
C6 C7 C8 C14 -78.2(3) . . . . ?
C6 C7 C12 C11 119.6(2) . . . . ?
C6 C7 C12 C13 -2.1(2) . . . . ?
C6 C16 C17 C18 -28.0(5) . . . . ?
C6 C16 C17 C22 151.3(3) . . . . ?
C7 C6 C16 C17 -2.0(5) . . . . ?
C7 C8 C9 C10 70.6(3) . . . . ?
C7 C8 C14 C11 -56.6(2) . . . . ?
C7 C12 C13 C1 -179.8(2) . . . . ?
C7 C12 C13 C5 -0.3(3) . . . . ?
C8 C7 C12 C11 -0.9(2) . . . . ?
C8 C7 C12 C13 -122.6(2) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C8 C14 C11 55.2(2) . . . . ?
C9 C10 C11 C12 -72.1(3) . . . . ?
C9 C10 C11 C14 33.9(3) . . . . ?
C10 C11 C12 C7 71.9(2) . . . . ?
C10 C11 C12 C13 -174.7(2) . . . . ?
C10 C11 C14 C8 -54.7(2) . . . . ?
C11 C12 C13 C1 67.4(3) . . . . ?
C11 C12 C13 C5 -113.1(3) . . . . ?
C12 C7 C8 C9 -70.2(3) . . . . ?
C12 C7 C8 C14 35.9(2) . . . . ?
C12 C11 C14 C8 55.9(2) . . . . ?
C13 C1 C2 C3 1.4(4) . . . . ?
C13 C5 C6 C7 -4.0(3) . . . . ?
C13 C5 C6 C16 172.0(3) . . . . ?
C14 C8 C9 C10 -35.4(3) . . . . ?
C14 C11 C12 C7 -34.5(2) . . . . ?
C14 C11 C12 C13 78.9(3) . . . . ?
C15 O1 C1 C2 8.3(4) . . . . ?
C15 O1 C1 C13 -172.3(3) . . . . ?
C16 C6 C7 C8 -59.8(3) . . . . ?
C16 C6 C7 C12 -172.2(3) . . . . ?
C16 C17 C18 C19 176.2(3) . . . . ?
C16 C17 C22 C21 -175.6(3) . . . . ?
C17 C18 C19 C20 0.1(5) . . . . ?
C18 C17 C22 C21 3.8(5) . . . . ?
C18 C19 C20 C21 2.3(5) . . . . ?
C18 C19 C20 C23 -178.1(3) . . . . ?
C19 C20 C21 C22 -1.6(5) . . . . ?
C20 C21 C22 C17 -1.5(6) . . . . ?
C22 C17 C18 C19 -3.1(4) . . . . ?
C23 C20 C21 C22 178.8(4) . . . . ?

_olex2_date_sample_data_collection 2009-06-05
_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 1.345
_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_exp_3112
_database_code_depnum_ccdc_archive 'CCDC 1949916'
loop_
_audit_author_name
_audit_author_address
haotaotao
;Si Chuan University
China
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2018-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H24 O'
_chemical_formula_sum            'C23 H24 O'
_chemical_formula_weight         316.42
_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 0.0033 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      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                   9.4684(6)
_cell_length_b                   10.1128(6)
_cell_length_c                   11.1589(9)
_cell_angle_alpha                111.746(7)
_cell_angle_beta                 114.773(7)
_cell_angle_gamma                91.316(5)
_cell_volume                     880.77(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5090
_cell_measurement_theta_min      3.5540
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6849
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.986
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   86.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   79.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -       16.8419   77.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega  -23.00   86.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -       16.8419    0.0000 -150.0000 109

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   18.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega  -42.00    1.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000  120.0000 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0338288000
_diffrn_orient_matrix_UB_12      0.0150916000
_diffrn_orient_matrix_UB_13      -0.0622757000
_diffrn_orient_matrix_UB_21      0.0426874000
_diffrn_orient_matrix_UB_22      0.0732886000
_diffrn_orient_matrix_UB_23      0.0430038000
_diffrn_orient_matrix_UB_31      0.0644867000
_diffrn_orient_matrix_UB_32      -0.0192282000
_diffrn_orient_matrix_UB_33      -0.0146763000
_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                2636
_reflns_number_total             3587
_reflns_odcompleteness_completeness 99.83
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.030
_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)+(0.0552P)²+0.1526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1276
_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:
 C7(H7), C8(H8), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C)
;
_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
O1 O 0.94285(14) 0.23253(14) 0.29099(15) 0.0608(4) Uani 1 1 d . . . . .
C1 C 0.84063(19) 0.12729(18) 0.28270(18) 0.0454(4) Uani 1 1 d . . . . .
C2 C 0.8844(2) 0.01437(19) 0.32213(19) 0.0513(4) Uani 1 1 d . . . . .
H2 H 0.9902 0.0057 0.3584 0.062 Uiso 1 1 calc R . . . .
C3 C 0.7684(2) -0.08610(18) 0.30686(19) 0.0509(4) Uani 1 1 d . . . . .
H3 H 0.7979 -0.1632 0.3314 0.061 Uiso 1 1 calc R . . . .
C4 C 0.6121(2) -0.07524(17) 0.25683(18) 0.0463(4) Uani 1 1 d . . . . .
H4 H 0.5367 -0.1430 0.2488 0.056 Uiso 1 1 calc R . . . .
C5 C 0.56772(18) 0.03985(16) 0.21792(16) 0.0393(4) Uani 1 1 d . . . . .
C6 C 0.40993(19) 0.07333(16) 0.15196(16) 0.0405(4) Uani 1 1 d . . . . .
C7 C 0.43087(18) 0.19873(17) 0.11263(17) 0.0414(4) Uani 1 1 d . . . . .
H7 H 0.3717 0.1690 0.0075 0.050 Uiso 1 1 calc R . . . .
C8 C 0.3920(2) 0.33959(18) 0.1966(2) 0.0506(4) Uani 1 1 d . . . . .
H8 H 0.2922 0.3254 0.2017 0.061 Uiso 1 1 calc R . . . .
C9 C 0.4054(2) 0.4503(2) 0.1359(2) 0.0623(5) Uani 1 1 d . . . . .
H9A H 0.3602 0.5327 0.1701 0.075 Uiso 1 1 calc R . . . .
H9B H 0.3524 0.4058 0.0305 0.075 Uiso 1 1 calc R . . . .
C10 C 0.5872(2) 0.4969(2) 0.1968(2) 0.0630(5) Uani 1 1 d . . . . .
H10A H 0.6160 0.4764 0.1189 0.076 Uiso 1 1 calc R . . . .
H10B H 0.6247 0.6000 0.2608 0.076 Uiso 1 1 calc R . . . .
C11 C 0.6552(2) 0.40409(18) 0.28029(19) 0.0497(4) Uani 1 1 d . . . . .
H11 H 0.7677 0.4401 0.3521 0.060 Uiso 1 1 calc R . . . .
C12 C 0.61272(18) 0.24515(17) 0.16806(17) 0.0409(4) Uani 1 1 d . . . . .
H12 H 0.6358 0.2385 0.0885 0.049 Uiso 1 1 calc R . . . .
C13 C 0.68184(19) 0.13836(16) 0.22809(16) 0.0397(4) Uani 1 1 d . . . . .
C14 C 0.5408(2) 0.40151(19) 0.3433(2) 0.0571(5) Uani 1 1 d . . . . .
H14A H 0.5413 0.4979 0.4073 0.068 Uiso 1 1 calc R . . . .
H14B H 0.5588 0.3370 0.3921 0.068 Uiso 1 1 calc R . . . .
C15 C 1.1069(2) 0.2405(2) 0.3646(2) 0.0668(5) Uani 1 1 d . . . . .
H15A H 1.1334 0.1537 0.3130 0.100 Uiso 1 1 calc GR . . . .
H15B H 1.1350 0.2494 0.4610 0.100 Uiso 1 1 calc GR . . . .
H15C H 1.1646 0.3238 0.3703 0.100 Uiso 1 1 calc GR . . . .
C16 C 0.26692(19) 0.01030(18) 0.12299(17) 0.0460(4) Uani 1 1 d . . . . .
H16 H 0.1817 0.0393 0.0654 0.055 Uiso 1 1 calc R . . . .
C17 C 0.22214(18) -0.09771(17) 0.16740(18) 0.0432(4) Uani 1 1 d . . . . .
C18 C 0.0913(2) -0.21099(19) 0.07002(19) 0.0520(4) Uani 1 1 d . . . . .
H18 H 0.0366 -0.2228 -0.0258 0.062 Uiso 1 1 calc R . . . .
C19 C 0.0404(2) -0.30673(19) 0.1123(2) 0.0560(5) Uani 1 1 d . . . . .
H19 H -0.0474 -0.3823 0.0440 0.067 Uiso 1 1 calc R . . . .
C20 C 0.1164(2) -0.29331(18) 0.2537(2) 0.0503(4) Uani 1 1 d . . . . .
C21 C 0.2464(2) -0.17972(19) 0.35145(19) 0.0510(4) Uani 1 1 d . . . . .
H21 H 0.3005 -0.1680 0.4473 0.061 Uiso 1 1 calc R . . . .
C22 C 0.2979(2) -0.08337(18) 0.31011(18) 0.0492(4) Uani 1 1 d . . . . .
H22 H 0.3851 -0.0072 0.3789 0.059 Uiso 1 1 calc R . . . .
C23 C 0.0593(3) -0.3975(2) 0.2994(3) 0.0787(6) Uani 1 1 d . . . . .
H23A H 0.1467 -0.4358 0.3478 0.118 Uiso 1 1 calc GR . . . .
H23B H -0.0224 -0.4760 0.2152 0.118 Uiso 1 1 calc GR . . . .
H23C H 0.0172 -0.3472 0.3644 0.118 Uiso 1 1 calc GR . . . .


_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 C1 1.3722(19) . ?
O1 C15 1.404(2) . ?
C1 C2 1.382(2) . ?
C1 C13 1.391(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(2) . ?
C5 C6 1.475(2) . ?
C5 C13 1.392(2) . ?
C6 C7 1.521(2) . ?
C6 C16 1.336(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.538(2) . ?
C7 C12 1.557(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.535(2) . ?
C8 C14 1.525(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.547(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.529(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.540(2) . ?
C11 C14 1.523(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.498(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.475(2) . ?
C17 C18 1.383(2) . ?
C17 C22 1.392(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(2) . ?
C20 C21 1.381(2) . ?
C20 C23 1.505(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(2) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 O1 C15 118.02(14) . . ?
O1 C1 C2 124.98(15) . . ?
O1 C1 C13 115.32(14) . . ?
C2 C1 C13 119.69(15) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.18(16) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.12(15) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.77(15) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 130.96(14) . . ?
C13 C5 C4 119.66(14) . . ?
C13 C5 C6 109.15(13) . . ?
C5 C6 C7 107.79(12) . . ?
C16 C6 C5 130.53(14) . . ?
C16 C6 C7 121.65(14) . . ?
C6 C7 H7 111.1 . . ?
C6 C7 C8 114.55(12) . . ?
C6 C7 C12 106.29(12) . . ?
C8 C7 H7 111.1 . . ?
C8 C7 C12 102.26(13) . . ?
C12 C7 H7 111.1 . . ?
C7 C8 H8 114.5 . . ?
C9 C8 C7 108.09(14) . . ?
C9 C8 H8 114.5 . . ?
C14 C8 C7 101.90(13) . . ?
C14 C8 H8 114.6 . . ?
C14 C8 C9 101.73(14) . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C8 C9 C10 102.91(14) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.2 . . ?
C10 C9 H9B 111.2 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 103.38(14) . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C10 C11 H11 114.9 . . ?
C10 C11 C12 107.62(14) . . ?
C12 C11 H11 114.9 . . ?
C14 C11 C10 101.04(15) . . ?
C14 C11 H11 114.9 . . ?
C14 C11 C12 101.97(13) . . ?
C7 C12 H12 111.1 . . ?
C11 C12 C7 103.51(13) . . ?
C11 C12 H12 111.1 . . ?
C13 C12 C7 103.59(12) . . ?
C13 C12 C11 115.75(13) . . ?
C13 C12 H12 111.1 . . ?
C1 C13 C5 120.51(14) . . ?
C1 C13 C12 126.33(14) . . ?
C5 C13 C12 113.07(13) . . ?
C8 C14 H14A 112.8 . . ?
C8 C14 H14B 112.8 . . ?
C11 C14 C8 94.81(13) . . ?
C11 C14 H14A 112.8 . . ?
C11 C14 H14B 112.8 . . ?
H14A C14 H14B 110.2 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16 114.7 . . ?
C6 C16 C17 130.52(15) . . ?
C17 C16 H16 114.7 . . ?
C18 C17 C16 120.36(15) . . ?
C18 C17 C22 117.03(15) . . ?
C22 C17 C16 122.32(14) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.26(16) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.74(16) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C23 121.44(17) . . ?
C21 C20 C19 117.15(16) . . ?
C21 C20 C23 121.41(17) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.49(16) . . ?
C22 C21 H21 119.3 . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.33(15) . . ?
C21 C22 H22 119.3 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C1 C2 C3 -179.33(16) . . . . ?
O1 C1 C13 C5 -178.43(14) . . . . ?
O1 C1 C13 C12 5.1(2) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C1 C13 C5 2.4(2) . . . . ?
C2 C1 C13 C12 -174.03(15) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 175.05(15) . . . . ?
C3 C4 C5 C13 1.2(2) . . . . ?
C4 C5 C6 C7 -171.39(16) . . . . ?
C4 C5 C6 C16 6.8(3) . . . . ?
C4 C5 C13 C1 -2.9(2) . . . . ?
C4 C5 C13 C12 173.96(13) . . . . ?
C5 C6 C7 C8 -115.66(15) . . . . ?
C5 C6 C7 C12 -3.53(15) . . . . ?
C5 C6 C16 C17 10.9(3) . . . . ?
C6 C5 C13 C1 -177.96(13) . . . . ?
C6 C5 C13 C12 -1.09(17) . . . . ?
C6 C7 C8 C9 -175.37(14) . . . . ?
C6 C7 C8 C14 77.92(16) . . . . ?
C6 C7 C12 C11 -118.38(13) . . . . ?
C6 C7 C12 C13 2.80(15) . . . . ?
C6 C16 C17 C18 -139.41(18) . . . . ?
C6 C16 C17 C22 46.9(3) . . . . ?
C7 C6 C16 C17 -171.16(15) . . . . ?
C7 C8 C9 C10 -73.22(18) . . . . ?
C7 C8 C14 C11 56.28(14) . . . . ?
C7 C12 C13 C1 175.52(15) . . . . ?
C7 C12 C13 C5 -1.13(17) . . . . ?
C8 C7 C12 C11 2.05(14) . . . . ?
C8 C7 C12 C13 123.22(13) . . . . ?
C8 C9 C10 C11 1.80(19) . . . . ?
C9 C8 C14 C11 -55.30(15) . . . . ?
C9 C10 C11 C12 69.89(18) . . . . ?
C9 C10 C11 C14 -36.59(18) . . . . ?
C10 C11 C12 C7 -72.67(15) . . . . ?
C10 C11 C12 C13 174.74(13) . . . . ?
C10 C11 C14 C8 56.30(15) . . . . ?
C11 C12 C13 C1 -71.9(2) . . . . ?
C11 C12 C13 C5 111.42(16) . . . . ?
C12 C7 C8 C9 70.12(16) . . . . ?
C12 C7 C8 C14 -36.58(14) . . . . ?
C12 C11 C14 C8 -54.59(14) . . . . ?
C13 C1 C2 C3 -0.2(3) . . . . ?
C13 C5 C6 C7 2.92(16) . . . . ?
C13 C5 C6 C16 -178.88(16) . . . . ?
C14 C8 C9 C10 33.60(18) . . . . ?
C14 C11 C12 C7 33.16(15) . . . . ?
C14 C11 C12 C13 -79.43(17) . . . . ?
C15 O1 C1 C2 -10.1(3) . . . . ?
C15 O1 C1 C13 170.75(15) . . . . ?
C16 C6 C7 C8 65.9(2) . . . . ?
C16 C6 C7 C12 178.07(14) . . . . ?
C16 C17 C18 C19 -175.10(16) . . . . ?
C16 C17 C22 C21 175.09(16) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C17 C22 C21 1.2(2) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C18 C19 C20 C23 179.48(18) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C17 -0.9(3) . . . . ?
C22 C17 C18 C19 -1.1(3) . . . . ?
C23 C20 C21 C22 -179.36(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_190531_s1_htt_447_2a
_database_code_depnum_ccdc_archive 'CCDC 1949917'
loop_
_audit_author_name
_audit_author_address
haotaotao
;Si Chuan University
China
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_audit_creation_date             2019-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C26 H25 O'
_chemical_formula_sum            'C26 H25 O'
_chemical_formula_weight         353.46
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3cl1
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           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   11.9345(13)
_cell_length_b                   7.2394(8)
_cell_length_c                   22.679(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.029(11)
_cell_angle_gamma                90
_cell_volume                     1935.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.3060
_cell_measurement_theta_min      3.4400
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4757
_diffrn_reflns_point_group_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.957
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   50.00   77.00   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   57.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   84.40   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   57.0000 -180.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   85.00   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762   77.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -34.00   11.90   0.9000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       17.0762  -57.0000 -180.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0345150000
_diffrn_orient_matrix_UB_12      0.0021096000
_diffrn_orient_matrix_UB_13      -0.0285062000
_diffrn_orient_matrix_UB_21      0.0493523000
_diffrn_orient_matrix_UB_22      0.0019311000
_diffrn_orient_matrix_UB_23      -0.0138082000
_diffrn_orient_matrix_UB_31      0.0002236000
_diffrn_orient_matrix_UB_32      -0.0978245000
_diffrn_orient_matrix_UB_33      -0.0008870000
_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         0.463
_reflns_Friedel_fraction_full    0.574
_reflns_Friedel_fraction_max     0.545
_reflns_number_gt                2361
_reflns_number_total             3120
_reflns_odcompleteness_completeness 99.81
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 630 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.7(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0530
_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)+(0.0611P)²+0.2259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1344
_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:
 C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C19(H19), C21(H21),
 C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.0220(2) 0.5065(4) 0.23459(11) 0.0523(7) Uani 1 1 d . . . . .
C1 C 0.1277(3) 0.6464(5) 0.31828(15) 0.0367(8) Uani 1 1 d . . . . .
C2 C 0.1185(3) 0.5044(6) 0.27665(16) 0.0420(9) Uani 1 1 d . . . . .
C3 C 0.2029(3) 0.3745(6) 0.27951(17) 0.0526(11) Uani 1 1 d . . . . .
H3 H 0.1964 0.2776 0.2523 0.063 Uiso 1 1 calc R . . . .
C4 C 0.2977(4) 0.3881(6) 0.32296(17) 0.0546(11) Uani 1 1 d . . . . .
H4 H 0.3549 0.3003 0.3244 0.066 Uiso 1 1 calc R . . . .
C5 C 0.3090(3) 0.5296(6) 0.36438(16) 0.0467(10) Uani 1 1 d . . . . .
H5 H 0.3727 0.5370 0.3937 0.056 Uiso 1 1 calc R . . . .
C6 C 0.2231(3) 0.6604(5) 0.36127(15) 0.0389(9) Uani 1 1 d . . . . .
C7 C 0.2176(3) 0.8284(5) 0.39739(15) 0.0371(8) Uani 1 1 d . . . . .
C8 C 0.1056(3) 0.9230(5) 0.37471(14) 0.0358(8) Uani 1 1 d . . . . .
H8 H 0.1168 1.0494 0.3613 0.043 Uiso 1 1 calc R . . . .
C9 C 0.0232(3) 0.9168(6) 0.42088(15) 0.0410(9) Uani 1 1 d . . . . .
H9 H 0.0585 0.9469 0.4617 0.049 Uiso 1 1 calc R . . . .
C10 C -0.0853(3) 1.0281(6) 0.39849(16) 0.0448(9) Uani 1 1 d . . . . .
H10 H -0.1328 1.0327 0.4300 0.054 Uiso 1 1 calc R . . . .
C11 C -0.0753(4) 1.2206(6) 0.37357(19) 0.0578(11) Uani 1 1 d . . . . .
H11 H -0.0460 1.3261 0.3938 0.069 Uiso 1 1 calc R . . . .
C12 C -0.1229(4) 1.2018(7) 0.3096(2) 0.0618(12) Uani 1 1 d . . . . .
H12 H -0.1267 1.2993 0.2826 0.074 Uiso 1 1 calc R . . . .
C13 C -0.1593(4) 1.0352(7) 0.29437(19) 0.0582(12) Uani 1 1 d . . . . .
H13 H -0.1906 1.0018 0.2557 0.070 Uiso 1 1 calc R . . . .
C14 C -0.1451(3) 0.9057(6) 0.34574(17) 0.0452(10) Uani 1 1 d . . . . .
H14 H -0.2194 0.8645 0.3539 0.054 Uiso 1 1 calc R . . . .
C15 C -0.0644(3) 0.7391(5) 0.34581(15) 0.0408(9) Uani 1 1 d . . . . .
H15 H -0.1001 0.6278 0.3267 0.049 Uiso 1 1 calc R . . . .
C16 C 0.0449(3) 0.7991(5) 0.32270(15) 0.0379(9) Uani 1 1 d . . . . .
H16 H 0.0280 0.8683 0.2852 0.045 Uiso 1 1 calc R . . . .
C17 C -0.0215(3) 0.7187(6) 0.41300(15) 0.0450(9) Uani 1 1 d . . . . .
H17A H -0.0820 0.6937 0.4359 0.054 Uiso 1 1 calc R . . . .
H17B H 0.0380 0.6269 0.4217 0.054 Uiso 1 1 calc R . . . .
C18 C 0.0102(4) 0.3630(7) 0.19128(19) 0.0659(13) Uani 1 1 d . . . . .
H18A H 0.0173 0.2454 0.2111 0.099 Uiso 1 1 calc GR . . . .
H18B H 0.0684 0.3751 0.1667 0.099 Uiso 1 1 calc GR . . . .
H18C H -0.0629 0.3718 0.1668 0.099 Uiso 1 1 calc GR . . . .
C19 C 0.2967(3) 0.8774(6) 0.44320(16) 0.0444(10) Uani 1 1 d . . . . .
H19 H 0.3563 0.7939 0.4519 0.053 Uiso 1 1 calc R . . . .
C20 C 0.3055(3) 1.0397(6) 0.48193(16) 0.0422(9) Uani 1 1 d . . . . .
C21 C 0.2471(4) 1.2039(6) 0.46889(17) 0.0527(11) Uani 1 1 d . . . . .
H21 H 0.1966 1.2136 0.4334 0.063 Uiso 1 1 calc R . . . .
C22 C 0.2617(4) 1.3532(7) 0.50701(18) 0.0571(11) Uani 1 1 d . . . . .
H22 H 0.2212 1.4612 0.4967 0.069 Uiso 1 1 calc R . . . .
C23 C 0.3353(3) 1.3449(6) 0.56013(19) 0.0536(11) Uani 1 1 d . . . . .
C24 C 0.3942(4) 1.1848(7) 0.5734(2) 0.0667(14) Uani 1 1 d . . . . .
H24 H 0.4448 1.1769 0.6090 0.080 Uiso 1 1 calc R . . . .
C25 C 0.3807(4) 1.0345(7) 0.53565(19) 0.0623(12) Uani 1 1 d . . . . .
H25 H 0.4225 0.9278 0.5461 0.075 Uiso 1 1 calc R . . . .
C26 C 0.3509(4) 1.5087(8) 0.6024(2) 0.0764(15) Uani 1 1 d . . . . .
H26A H 0.3490 1.6210 0.5797 0.115 Uiso 1 1 calc GR . . . .
H26B H 0.4226 1.4986 0.6281 0.115 Uiso 1 1 calc GR . . . .
H26C H 0.2908 1.5102 0.6260 0.115 Uiso 1 1 calc GR . . . .


_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 C2 1.375(4) . ?
O1 C18 1.421(5) . ?
C1 C2 1.388(5) . ?
C1 C6 1.382(5) . ?
C1 C16 1.496(5) . ?
C2 C3 1.372(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(5) . ?
C6 C7 1.474(5) . ?
C7 C8 1.518(5) . ?
C7 C19 1.337(5) . ?
C8 H8 0.9800 . ?
C8 C9 1.545(4) . ?
C8 C16 1.566(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.543(5) . ?
C9 C17 1.531(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.516(6) . ?
C10 C14 1.568(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.479(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.310(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.484(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.543(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.543(5) . ?
C15 C17 1.537(5) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.461(5) . ?
C20 C21 1.385(6) . ?
C20 C25 1.396(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(5) . ?
C23 C24 1.365(6) . ?
C23 C26 1.517(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.379(6) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C2 O1 C18 116.9(3) . . ?
C2 C1 C16 127.6(3) . . ?
C6 C1 C2 120.1(3) . . ?
C6 C1 C16 112.2(3) . . ?
O1 C2 C1 115.6(3) . . ?
C3 C2 O1 124.7(3) . . ?
C3 C2 C1 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 C7 110.4(3) . . ?
C5 C6 C7 129.2(3) . . ?
C6 C7 C8 107.3(3) . . ?
C19 C7 C6 124.3(3) . . ?
C19 C7 C8 128.3(3) . . ?
C7 C8 H8 111.7 . . ?
C7 C8 C9 112.2(3) . . ?
C7 C8 C16 106.0(3) . . ?
C9 C8 H8 111.7 . . ?
C9 C8 C16 103.0(3) . . ?
C16 C8 H8 111.7 . . ?
C8 C9 H9 114.1 . . ?
C10 C9 C8 110.6(3) . . ?
C10 C9 H9 114.1 . . ?
C17 C9 C8 101.3(3) . . ?
C17 C9 H9 114.1 . . ?
C17 C9 C10 101.0(3) . . ?
C9 C10 H10 109.2 . . ?
C9 C10 C14 102.4(3) . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 H10 109.2 . . ?
C11 C10 C14 106.8(3) . . ?
C14 C10 H10 109.2 . . ?
C10 C11 H11 128.0 . . ?
C12 C11 C10 103.9(4) . . ?
C12 C11 H11 128.0 . . ?
C11 C12 H12 123.1 . . ?
C13 C12 C11 113.8(4) . . ?
C13 C12 H12 123.1 . . ?
C12 C13 H13 123.7 . . ?
C12 C13 C14 112.5(4) . . ?
C14 C13 H13 123.7 . . ?
C10 C14 H14 110.2 . . ?
C13 C14 C10 102.9(3) . . ?
C13 C14 H14 110.2 . . ?
C13 C14 C15 119.3(3) . . ?
C15 C14 C10 103.4(3) . . ?
C15 C14 H14 110.2 . . ?
C14 C15 H15 114.4 . . ?
C16 C15 C14 109.9(3) . . ?
C16 C15 H15 114.4 . . ?
C17 C15 C14 100.8(3) . . ?
C17 C15 H15 114.4 . . ?
C17 C15 C16 101.3(3) . . ?
C1 C16 C8 104.0(3) . . ?
C1 C16 C15 114.7(3) . . ?
C1 C16 H16 111.6 . . ?
C8 C16 H16 111.6 . . ?
C15 C16 C8 102.8(3) . . ?
C15 C16 H16 111.6 . . ?
C9 C17 C15 94.7(3) . . ?
C9 C17 H17A 112.8 . . ?
C9 C17 H17B 112.8 . . ?
C15 C17 H17A 112.8 . . ?
C15 C17 H17B 112.8 . . ?
H17A C17 H17B 110.2 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 H19 114.5 . . ?
C7 C19 C20 130.9(4) . . ?
C20 C19 H19 114.5 . . ?
C21 C20 C19 125.1(3) . . ?
C21 C20 C25 116.3(4) . . ?
C25 C20 C19 118.6(4) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 C20 121.9(4) . . ?
C22 C21 H21 119.0 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.0(4) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C26 121.1(4) . . ?
C24 C23 C22 117.8(4) . . ?
C24 C23 C26 121.1(4) . . ?
C23 C24 H24 119.1 . . ?
C23 C24 C25 121.8(4) . . ?
C25 C24 H24 119.1 . . ?
C20 C25 H25 119.4 . . ?
C24 C25 C20 121.2(4) . . ?
C24 C25 H25 119.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
O1 C2 C3 C4 178.5(4) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
C1 C6 C7 C8 1.5(4) . . . . ?
C1 C6 C7 C19 178.6(3) . . . . ?
C2 C1 C6 C5 -2.0(5) . . . . ?
C2 C1 C6 C7 175.8(3) . . . . ?
C2 C1 C16 C8 -175.7(3) . . . . ?
C2 C1 C16 C15 72.9(4) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?
C4 C5 C6 C7 -176.1(3) . . . . ?
C5 C6 C7 C8 179.1(4) . . . . ?
C5 C6 C7 C19 -3.8(6) . . . . ?
C6 C1 C2 O1 -177.9(3) . . . . ?
C6 C1 C2 C3 2.1(5) . . . . ?
C6 C1 C16 C8 2.6(4) . . . . ?
C6 C1 C16 C15 -108.8(3) . . . . ?
C6 C7 C8 C9 111.8(3) . . . . ?
C6 C7 C8 C16 0.1(4) . . . . ?
C6 C7 C19 C20 178.1(4) . . . . ?
C7 C8 C9 C10 175.2(3) . . . . ?
C7 C8 C9 C17 -78.3(3) . . . . ?
C7 C8 C16 C1 -1.6(3) . . . . ?
C7 C8 C16 C15 118.2(3) . . . . ?
C7 C19 C20 C21 -18.6(6) . . . . ?
C7 C19 C20 C25 163.6(4) . . . . ?
C8 C7 C19 C20 -5.5(6) . . . . ?
C8 C9 C10 C11 -47.7(4) . . . . ?
C8 C9 C10 C14 69.9(4) . . . . ?
C8 C9 C17 C15 -56.3(3) . . . . ?
C9 C8 C16 C1 -119.5(3) . . . . ?
C9 C8 C16 C15 0.3(3) . . . . ?
C9 C10 C11 C12 113.0(4) . . . . ?
C9 C10 C14 C13 -123.6(3) . . . . ?
C9 C10 C14 C15 1.2(4) . . . . ?
C10 C9 C17 C15 57.6(3) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C10 C14 C15 C16 -71.7(3) . . . . ?
C10 C14 C15 C17 34.6(4) . . . . ?
C11 C10 C14 C13 2.7(4) . . . . ?
C11 C10 C14 C15 127.4(3) . . . . ?
C11 C12 C13 C14 0.8(6) . . . . ?
C12 C13 C14 C10 -2.2(5) . . . . ?
C12 C13 C14 C15 -115.8(4) . . . . ?
C13 C14 C15 C16 41.7(5) . . . . ?
C13 C14 C15 C17 148.0(4) . . . . ?
C14 C10 C11 C12 -2.3(4) . . . . ?
C14 C15 C16 C1 -177.5(3) . . . . ?
C14 C15 C16 C8 70.4(3) . . . . ?
C14 C15 C17 C9 -56.5(3) . . . . ?
C16 C1 C2 O1 0.4(5) . . . . ?
C16 C1 C2 C3 -179.6(4) . . . . ?
C16 C1 C6 C5 179.4(3) . . . . ?
C16 C1 C6 C7 -2.7(4) . . . . ?
C16 C8 C9 C10 -71.2(4) . . . . ?
C16 C8 C9 C17 35.3(3) . . . . ?
C16 C15 C17 C9 56.6(3) . . . . ?
C17 C9 C10 C11 -154.3(3) . . . . ?
C17 C9 C10 C14 -36.7(3) . . . . ?
C17 C15 C16 C1 76.5(4) . . . . ?
C17 C15 C16 C8 -35.6(4) . . . . ?
C18 O1 C2 C1 179.9(3) . . . . ?
C18 O1 C2 C3 -0.1(6) . . . . ?
C19 C7 C8 C9 -65.1(5) . . . . ?
C19 C7 C8 C16 -176.8(3) . . . . ?
C19 C20 C21 C22 -178.4(4) . . . . ?
C19 C20 C25 C24 178.7(4) . . . . ?
C20 C21 C22 C23 -0.2(7) . . . . ?
C21 C20 C25 C24 0.8(6) . . . . ?
C21 C22 C23 C24 0.7(7) . . . . ?
C21 C22 C23 C26 -179.5(4) . . . . ?
C22 C23 C24 C25 -0.5(7) . . . . ?
C23 C24 C25 C20 -0.2(7) . . . . ?
C25 C20 C21 C22 -0.6(6) . . . . ?
C26 C23 C24 C25 179.8(4) . . . . ?

_olex2_date_sample_data_collection 2009-06-29
_olex2_submission_special_instructions 'No special instructions were received'
