# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_303
_database_code_depnum_ccdc_archive 'CCDC 1915415'
loop_
_audit_author_name
_audit_author_address
'Lu Liu'
;East China Normal University
China
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_audit_creation_date             2018-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_weight         316.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2055(2)
_cell_length_b                   17.4289(3)
_cell_length_c                   10.2408(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.039(2)
_cell_angle_gamma                90
_cell_volume                     1642.01(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7516
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0270
_cell_measurement_theta_min      4.9930
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.744
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15545
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         5.011
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  19.00   1.00    1.00    --    0.00 -57.00   0.00   45
  2  ω     62.00  89.00   1.00    1.00    --    0.00  38.00-120.00   27
  3  ω    -45.00 -19.00   1.00    1.00    --    0.00 -57.00 120.00   26
  4  ω    -87.00 -34.00   1.00    1.00    --    0.00 -57.00   0.00   53
  5  ω    -67.00  16.00   1.00    1.00    --    0.00 -19.00-120.00   83
  6  ω    -19.00  45.00   1.00    1.00    --    0.00  38.00-120.00   64
  7  ω      6.00  61.00   1.00    1.00    --   95.80 -77.00 -90.00   55
  8  ω    117.00 184.00   1.00    1.00    --   95.80  30.00  90.00   67
  9  ω      6.00  99.00   1.00    1.00    --   95.80 -45.00 -90.00   93
 10  ω     69.00 101.00   1.00    1.00    --   95.80 -82.00 -90.00   32
 11  ω     36.00 121.00   1.00    1.00    --   95.80 -82.00  30.00   85
 12  ω     79.00 104.00   1.00    1.00    --   95.80  30.00   0.00   25
 13  ω    122.00 185.00   1.00    1.00    --   95.80  30.00   0.00   63
 14  ω     38.00  64.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 15  ω     18.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  110
 16  ω     28.00 119.00   1.00    1.00    --   95.80 -15.00   0.00   91
 17  ω     14.00 118.00   1.00    1.00    --   95.80 -61.00 150.00  104
 18  ω     21.00 106.00   1.00    1.00    --   95.80 -61.00  30.00   85
 19  ω     82.00 107.00   1.00    1.00    --   95.80 -77.00 -90.00   25
 20  ω     80.00 105.00   1.00    1.00    --   95.80 -82.00 -60.00   25
 21  ω     76.00 184.00   1.00    1.00    --   95.80  30.00  30.00  108
 22  ω    126.00 152.00   1.00    1.00    --   95.80  30.00 -90.00   26
 23  ω     78.00 103.00   1.00    1.00    --   95.80 -82.00  90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0233122000
_diffrn_orient_matrix_UB_12      -0.0303541000
_diffrn_orient_matrix_UB_13      -0.1404501000
_diffrn_orient_matrix_UB_21      0.0217054000
_diffrn_orient_matrix_UB_22      -0.0827386000
_diffrn_orient_matrix_UB_23      0.0498351000
_diffrn_orient_matrix_UB_31      -0.1644463000
_diffrn_orient_matrix_UB_32      -0.0066504000
_diffrn_orient_matrix_UB_33      0.0210343000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2505
_reflns_number_total             2918
_reflns_odcompleteness_completeness 99.93
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.167
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2918
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.068
_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)+(0.0500P)²+0.2580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1142
_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:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C11(H11), C16(H16), C3(H3), C14(H14), C12(H12), C13(H13), C6(H6),
 C4(H4), C5(H5)
2.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
O1 O 0.42620(12) 0.24313(6) 0.44699(11) 0.0578(3) Uani 1 1 d . . . . .
O2 O 0.53219(12) 0.38391(7) 0.31179(10) 0.0595(3) Uani 1 1 d . . . . .
O3 O 0.66045(13) 0.38047(8) 0.50210(12) 0.0703(4) Uani 1 1 d . . . . .
C9 C 0.26972(15) 0.35273(7) 0.44447(13) 0.0406(3) Uani 1 1 d . . . . .
C10 C 0.17366(15) 0.39712(7) 0.34755(13) 0.0418(3) Uani 1 1 d . . . . .
C18 C 0.32226(15) 0.27491(8) 0.39304(13) 0.0430(3) Uani 1 1 d . . . . .
C1 C 0.40117(15) 0.40021(7) 0.50213(13) 0.0424(3) Uani 1 1 d . . . . .
H1 H 0.378419 0.454230 0.484463 0.051 Uiso 1 1 calc R . . . .
C15 C 0.11566(15) 0.36129(8) 0.23466(13) 0.0456(3) Uani 1 1 d . . . . .
C2 C 0.39774(17) 0.39032(8) 0.64831(13) 0.0460(4) Uani 1 1 d . . . . .
C8 C 0.18393(17) 0.33008(8) 0.56701(14) 0.0479(4) Uani 1 1 d . . . . .
C20 C 0.54615(17) 0.38497(8) 0.44288(14) 0.0483(4) Uani 1 1 d . . . . .
C17 C 0.24270(17) 0.24054(8) 0.28331(15) 0.0507(4) Uani 1 1 d . . . . .
H17 H 0.257117 0.188982 0.264309 0.061 Uiso 1 1 calc R . . . .
C11 C 0.13461(17) 0.47278(8) 0.37158(15) 0.0523(4) Uani 1 1 d . . . . .
H11 H 0.169282 0.496856 0.447510 0.063 Uiso 1 1 calc R . . . .
C16 C 0.14958(17) 0.28118(9) 0.20931(15) 0.0528(4) Uani 1 1 d . . . . .
H16 H 0.103811 0.257290 0.137811 0.063 Uiso 1 1 calc R . . . .
C7 C 0.27377(17) 0.35135(8) 0.68278(14) 0.0496(4) Uani 1 1 d . . . . .
C3 C 0.49504(19) 0.41927(9) 0.74295(15) 0.0583(4) Uani 1 1 d . . . . .
H3 H 0.577709 0.445885 0.719514 0.070 Uiso 1 1 calc R . . . .
C14 C 0.02497(18) 0.40249(10) 0.14797(16) 0.0581(4) Uani 1 1 d . . . . .
H14 H -0.012719 0.378686 0.072877 0.070 Uiso 1 1 calc R . . . .
C12 C 0.04504(18) 0.51271(9) 0.28431(17) 0.0615(4) Uani 1 1 d . . . . .
H12 H 0.021352 0.563514 0.301432 0.074 Uiso 1 1 calc R . . . .
C13 C -0.00941(19) 0.47787(10) 0.17218(17) 0.0635(4) Uani 1 1 d . . . . .
H13 H -0.068920 0.505078 0.113311 0.076 Uiso 1 1 calc R . . . .
C19 C 0.05401(19) 0.29846(10) 0.56228(19) 0.0683(5) Uani 1 1 d . . . . .
H19A H 0.008049 0.286859 0.639243 0.082 Uiso 1 1 calc R . . . .
H19B H 0.008176 0.287711 0.481961 0.082 Uiso 1 1 calc R . . . .
C6 C 0.2451(2) 0.33958(10) 0.81488(16) 0.0663(5) Uani 1 1 d . . . . .
H6 H 0.162487 0.313167 0.839083 0.080 Uiso 1 1 calc R . . . .
C4 C 0.4655(2) 0.40739(11) 0.87301(17) 0.0723(5) Uani 1 1 d . . . . .
H4 H 0.529371 0.426105 0.937782 0.087 Uiso 1 1 calc R . . . .
C5 C 0.3426(3) 0.36821(12) 0.90793(17) 0.0771(6) Uani 1 1 d . . . . .
H5 H 0.325202 0.360949 0.995968 0.092 Uiso 1 1 calc R . . . .
C21 C 0.6663(2) 0.37956(13) 0.24347(19) 0.0789(6) Uani 1 1 d . . . . .
H21A H 0.645138 0.371691 0.151985 0.118 Uiso 1 1 calc GR . . . .
H21B H 0.723560 0.337529 0.277337 0.118 Uiso 1 1 calc GR . . . .
H21C H 0.719469 0.426553 0.255639 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 C18 1.2207(17) . ?
O2 C20 1.3442(18) . ?
O2 C21 1.443(2) . ?
O3 C20 1.1981(18) . ?
C9 C10 1.5176(19) . ?
C9 C18 1.5392(18) . ?
C9 C1 1.5642(18) . ?
C9 C8 1.5572(18) . ?
C10 C15 1.4027(19) . ?
C10 C11 1.391(2) . ?
C18 C17 1.449(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.5084(19) . ?
C1 C20 1.509(2) . ?
C15 C16 1.456(2) . ?
C15 C14 1.396(2) . ?
C2 C7 1.384(2) . ?
C2 C3 1.391(2) . ?
C8 C7 1.469(2) . ?
C8 C19 1.316(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.328(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C16 H16 0.9300 . ?
C7 C6 1.403(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.376(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(2) . ?
C13 H13 0.9300 . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C20 O2 C21 115.59(14) . . ?
C10 C9 C18 114.09(11) . . ?
C10 C9 C1 113.72(10) . . ?
C10 C9 C8 110.85(11) . . ?
C18 C9 C1 110.31(11) . . ?
C18 C9 C8 103.11(10) . . ?
C8 C9 C1 103.75(11) . . ?
C15 C10 C9 120.53(12) . . ?
C11 C10 C9 121.04(12) . . ?
C11 C10 C15 118.34(13) . . ?
O1 C18 C9 119.72(12) . . ?
O1 C18 C17 122.00(13) . . ?
C17 C18 C9 118.25(12) . . ?
C9 C1 H1 106.3 . . ?
C2 C1 C9 105.72(11) . . ?
C2 C1 H1 106.3 . . ?
C2 C1 C20 115.40(12) . . ?
C20 C1 C9 116.01(11) . . ?
C20 C1 H1 106.3 . . ?
C10 C15 C16 119.74(13) . . ?
C14 C15 C10 119.78(14) . . ?
C14 C15 C16 120.48(13) . . ?
C7 C2 C1 110.84(12) . . ?
C7 C2 C3 121.10(14) . . ?
C3 C2 C1 127.91(14) . . ?
C7 C8 C9 107.42(12) . . ?
C19 C8 C9 124.24(15) . . ?
C19 C8 C7 128.34(14) . . ?
O2 C20 C1 110.45(13) . . ?
O3 C20 O2 123.75(14) . . ?
O3 C20 C1 125.54(14) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 C18 121.35(13) . . ?
C16 C17 H17 119.3 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.99(15) . . ?
C12 C11 H11 119.5 . . ?
C15 C16 H16 118.4 . . ?
C17 C16 C15 123.20(13) . . ?
C17 C16 H16 118.4 . . ?
C2 C7 C8 111.32(12) . . ?
C2 C7 C6 120.19(15) . . ?
C6 C7 C8 128.44(15) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.18(17) . . ?
C4 C3 H3 120.9 . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.86(15) . . ?
C13 C14 H14 119.6 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.53(15) . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.47(15) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C8 C19 H19A 120.0 . . ?
C8 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C7 C6 H6 120.9 . . ?
C5 C6 C7 118.24(18) . . ?
C5 C6 H6 120.9 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.98(17) . . ?
C5 C4 H4 119.5 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.31(16) . . ?
C4 C5 H5 119.3 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_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 2.553
_oxdiff_exptl_absorpt_empirical_full_min 0.450
####################################################################### 
# 
# 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_322
_database_code_depnum_ccdc_archive 'CCDC 1915417'
loop_
_audit_author_name
_audit_author_address
'Lu Liu'
;East China Normal University
China
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_audit_creation_date             2018-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 O3'
_chemical_formula_sum            'C21 H16 O3'
_chemical_formula_weight         316.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.12640(10)
_cell_length_b                   13.3342(3)
_cell_length_c                   14.6256(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.275(2)
_cell_angle_gamma                90
_cell_volume                     1582.23(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14090
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2080
_cell_measurement_theta_min      4.4650
_shelx_estimated_absorpt_T_max   0.826
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1159
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34794
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         4.491
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  19.00   1.00    1.00    --    0.00 -57.00  90.00   26
  2  ω    -14.00  12.00   1.00    1.00    --    0.00  57.00  30.00   26
  3  ω    -19.00  24.00   1.00    1.00    --    0.00  38.00-180.00   43
  4  ω    -80.00 -42.00   1.00    1.00    --    0.00 -57.00  90.00   38
  5  ω    -19.00  18.00   1.00    1.00    --    0.00  38.00  90.00   37
  6  ω     25.00  88.00   1.00    1.00    --    0.00  38.00-120.00   63
  7  ω     56.00  86.00   1.00    1.00    --    0.00  38.00  90.00   30
  8  ω     32.00  89.00   1.00    1.00    --    0.00  38.00-180.00   57
  9  ω    -29.00  63.00   1.00    1.00    --    0.00  77.00 -60.00   92
 10  ω     23.00  78.00   1.00    1.00    --    0.00  77.00  90.00   55
 11  ω    -19.00  17.00   1.00    1.00    --    0.00  38.00-120.00   36
 12  ω     30.00  80.00   1.00    1.00    --    0.00  57.00  30.00   50
 13  ω     52.00  82.00   1.00    1.00    --    0.00  38.00   0.00   30
 14  ω    -17.00  22.00   1.00    1.00    --    0.00  38.00   0.00   39
 15  ω    -29.00   2.00   1.00    1.00    --    0.00  77.00  90.00   31
 16  ω     65.00  97.00   1.00    2.00    --   95.80  82.00 -60.00   32
 17  ω     58.00 128.00   1.00    2.00    --   95.80 -82.00 -90.00   70
 18  ω    136.00 179.00   1.00    2.00    --   95.80  82.00-110.98   43
 19  ω     70.00 185.00   1.00    2.00    --   95.80  64.00  72.11  115
 20  ω     69.00 180.00   1.00    2.00    --   95.80  66.00  35.65  111
 21  ω     63.00  89.00   1.00    2.00    --   95.80  82.00-110.98   26
 22  ω     75.00 185.00   1.00    2.00    --   95.80  46.00 139.90  110
 23  ω     75.00 108.00   1.00    2.00    --   95.80  45.00 -60.00   33
 24  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -30.00   25
 25  ω     63.00  88.00   1.00    2.00    --   95.80  82.00-150.00   25
 26  ω     71.00 116.00   1.00    2.00    --   95.80  61.00  90.00   45
 27  ω    155.00 185.00   1.00    2.00    --   95.80  61.00  90.00   30
 28  ω     75.00 107.00   1.00    2.00    --   95.80  45.00 -30.00   32
 29  ω    126.00 184.00   1.00    2.00    --   95.80  45.00 -30.00   58
 30  ω     65.00  91.00   1.00    2.00    --   95.80  77.00-120.00   26
 31  ω     50.00 123.00   1.00    2.00    --   95.80 -82.00  60.00   73
 32  ω    126.00 151.00   1.00    2.00    --   95.80  76.00  24.87   25
 33  ω     32.00 127.00   1.00    2.00    --   95.80 -82.00-150.00   95
 34  ω    107.00 185.00   1.00    2.00    --   95.80  82.00 -90.00   78
 35  ω     65.00  90.00   1.00    2.00    --   95.80  76.00  24.87   25
 36  ω    154.00 179.00   1.00    2.00    --   95.80  75.00  -3.07   25
 37  ω     63.00 124.00   1.00    2.00    --   95.80 -82.00 120.00   61
 38  ω     65.00  97.00   1.00    2.00    --   95.80  82.00 -90.00   32
 39  ω     63.00  89.00   1.00    2.00    --   95.80  82.00 -30.00   26
 40  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-180.00   25
 41  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -60.00   26
 42  ω    141.00 167.00   1.00    2.00    --   95.80  77.00 -60.00   26
 43  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 44  ω     64.00  90.00   1.00    2.00    --   95.80  82.00  90.00   26
 45  ω     82.00 113.00   1.00    2.00    --   95.80 -82.00   0.00   31
 46  ω     67.00  92.00   1.00    2.00    --   95.80  73.00 177.27   25
 47  ω     26.00  77.00   1.00    2.00    --   95.80 -82.00   0.00   51
 48  ω     75.00 158.00   1.00    2.00    --   95.80  45.00   0.00   83
 49  ω     72.00  98.00   1.00    2.00    --   95.80  61.00 -90.00   26
 50  ω     65.00 173.00   1.00    2.00    --   95.80  77.00-150.00  108
 51  ω     65.00  99.00   1.00    2.00    --   95.80  77.00 120.00   34
 52  ω     72.00 109.00   1.00    2.00    --   95.80  61.00   0.00   37
 53  ω     65.00  91.00   1.00    2.00    --   95.80  77.00 -90.00   26
 54  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 150.00   25
 55  ω     63.00  88.00   1.00    2.00    --   95.80  82.00  30.00   25
 56  ω     68.00  94.00   1.00    2.00    --   95.80  82.00  60.00   26
 57  ω    122.00 179.00   1.00    2.00    --   95.80  82.00  60.00   57
 58  ω     63.00  89.00   1.00    2.00    --   95.80  82.00 120.00   26
 59  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  90.00   25
 60  ω    150.00 182.00   1.00    2.00    --   95.80  82.00 150.00   32
 61  ω    111.00 136.00   1.00    2.00    --   95.80  77.00   0.00   25
 62  ω     71.00  97.00   1.00    2.00    --   95.80  61.00  30.00   26
 63  ω     68.00  93.00   1.00    2.00    --   95.80  77.00   0.00   25
 64  ω     63.00 106.00   1.00    2.00    --   95.80  82.00 150.00   43
 65  ω    160.00 185.00   1.00    2.00    --   95.80  82.00 -60.00   25
 66  ω     63.00 176.00   1.00    2.00    --   95.80  81.00-165.45  113
 67  ω     71.00 106.00   1.00    2.00    --   95.80  61.00  60.00   35
 68  ω     66.00  92.00   1.00    2.00    --   95.80  75.00  -3.07   26
 69  ω     71.00 156.00   1.00    2.00    --   95.80  62.00 157.78   85
 70  ω     76.00 183.00   1.00    2.00    --   95.80  35.00 -82.24  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0731973000
_diffrn_orient_matrix_UB_12      0.0230917000
_diffrn_orient_matrix_UB_13      -0.0972282000
_diffrn_orient_matrix_UB_21      -0.1721672000
_diffrn_orient_matrix_UB_22      0.0114705000
_diffrn_orient_matrix_UB_23      0.0376972000
_diffrn_orient_matrix_UB_31      0.0324504000
_diffrn_orient_matrix_UB_32      0.1126108000
_diffrn_orient_matrix_UB_33      0.0161399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2525
_reflns_number_total             2816
_reflns_odcompleteness_completeness 99.93
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.198
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.015
_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)+(0.0558P)²+0.6493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1100
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
O1 O 0.95859(14) 0.10826(8) 0.56383(7) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.44493(13) 0.29162(9) 0.62652(7) 0.0290(3) Uani 1 1 d . . . . .
O3 O 0.52320(13) 0.15269(8) 0.55273(7) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.96655(18) 0.33447(11) 0.53742(10) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.93238(18) 0.38831(11) 0.62226(10) 0.0210(3) Uani 1 1 d . . . . .
C3 C 1.0184(2) 0.46857(12) 0.66330(11) 0.0277(4) Uani 1 1 d . . . . .
H3 H 1.110200 0.495272 0.636975 0.033 Uiso 1 1 calc R . . . .
C4 C 0.9642(2) 0.50776(13) 0.74412(11) 0.0307(4) Uani 1 1 d . . . . .
H4 H 1.019393 0.561864 0.771844 0.037 Uiso 1 1 calc R . . . .
C5 C 0.8284(2) 0.46693(13) 0.78404(11) 0.0298(4) Uani 1 1 d . . . . .
H5 H 0.794237 0.493692 0.838529 0.036 Uiso 1 1 calc R . . . .
C6 C 0.74282(19) 0.38661(12) 0.74364(10) 0.0243(3) Uani 1 1 d . . . . .
H6 H 0.652279 0.359222 0.770717 0.029 Uiso 1 1 calc R . . . .
C7 C 0.79540(18) 0.34809(11) 0.66193(9) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.73462(18) 0.25674(11) 0.60963(9) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.780461 0.198698 0.643384 0.023 Uiso 1 1 calc R . . . .
C9 C 0.82252(17) 0.25999(11) 0.51681(9) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.89586(18) 0.15610(11) 0.49927(10) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.89427(19) 0.11755(11) 0.40608(10) 0.0225(3) Uani 1 1 d . . . . .
H11 H 0.951079 0.058858 0.394222 0.027 Uiso 1 1 calc R . . . .
C12 C 0.81171(18) 0.16575(11) 0.33697(10) 0.0223(3) Uani 1 1 d . . . . .
H12 H 0.813484 0.138778 0.278389 0.027 Uiso 1 1 calc R . . . .
C13 C 0.71993(17) 0.25775(11) 0.34912(9) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.63386(18) 0.30245(12) 0.27408(10) 0.0213(3) Uani 1 1 d . . . . .
H14 H 0.636187 0.273001 0.216531 0.026 Uiso 1 1 calc R . . . .
C15 C 0.54576(19) 0.38958(12) 0.28460(10) 0.0244(3) Uani 1 1 d . . . . .
H15 H 0.489443 0.418894 0.234302 0.029 Uiso 1 1 calc R . . . .
C16 C 0.5413(2) 0.43338(13) 0.37025(10) 0.0288(4) Uani 1 1 d . . . . .
H16 H 0.481281 0.491901 0.377651 0.035 Uiso 1 1 calc R . . . .
C17 C 0.6269(2) 0.38973(12) 0.44538(10) 0.0255(4) Uani 1 1 d . . . . .
H17 H 0.623626 0.419791 0.502631 0.031 Uiso 1 1 calc R . . . .
C18 C 0.71663(17) 0.30243(11) 0.43628(9) 0.0177(3) Uani 1 1 d . . . . .
C19 C 1.09282(19) 0.34774(12) 0.48522(11) 0.0261(4) Uani 1 1 d . . . . .
H19A H 1.172531 0.395706 0.501003 0.031 Uiso 1 1 calc R . . . .
H19B H 1.101704 0.309087 0.432801 0.031 Uiso 1 1 calc R . . . .
C20 C 0.55140(18) 0.23924(11) 0.59812(9) 0.0200(3) Uani 1 1 d . . . . .
C21 C 0.35226(19) 0.12448(13) 0.53503(12) 0.0310(4) Uani 1 1 d . . . . .
H21A H 0.302970 0.166580 0.487769 0.046 Uiso 1 1 calc GR . . . .
H21B H 0.294282 0.132428 0.589945 0.046 Uiso 1 1 calc GR . . . .
H21C H 0.346200 0.055736 0.515626 0.046 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 C10 1.2260(17) . ?
O2 C20 1.2043(18) . ?
O3 C20 1.3444(18) . ?
O3 C21 1.4482(18) . ?
C1 C2 1.474(2) . ?
C1 C9 1.551(2) . ?
C1 C19 1.325(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.390(2) . ?
C7 C8 1.506(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.5703(19) . ?
C8 C20 1.507(2) . ?
C9 C10 1.535(2) . ?
C9 C18 1.5271(18) . ?
C10 C11 1.456(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.344(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.452(2) . ?
C13 C14 1.400(2) . ?
C13 C18 1.4088(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(2) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C20 O3 C21 116.48(12) . . ?
C2 C1 C9 107.40(12) . . ?
C19 C1 C2 127.54(14) . . ?
C19 C1 C9 125.02(14) . . ?
C3 C2 C1 128.48(14) . . ?
C7 C2 C1 110.91(13) . . ?
C7 C2 C3 120.60(14) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.72(16) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.59(15) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.91(15) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.62(15) . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C8 110.29(12) . . ?
C6 C7 C2 120.55(14) . . ?
C6 C7 C8 128.84(14) . . ?
C7 C8 H8 106.2 . . ?
C7 C8 C9 105.34(12) . . ?
C7 C8 C20 118.37(12) . . ?
C9 C8 H8 106.2 . . ?
C20 C8 H8 106.2 . . ?
C20 C8 C9 113.76(11) . . ?
C1 C9 C8 103.00(11) . . ?
C10 C9 C1 108.32(11) . . ?
C10 C9 C8 108.64(11) . . ?
C18 C9 C1 107.35(11) . . ?
C18 C9 C8 114.39(11) . . ?
C18 C9 C10 114.36(11) . . ?
O1 C10 C9 119.28(13) . . ?
O1 C10 C11 121.21(13) . . ?
C11 C10 C9 119.48(12) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.83(14) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 118.3 . . ?
C11 C12 C13 123.34(13) . . ?
C13 C12 H12 118.3 . . ?
C14 C13 C12 120.05(13) . . ?
C14 C13 C18 119.65(13) . . ?
C18 C13 C12 120.30(13) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.72(13) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.81(13) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.98(14) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.15(14) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 C9 120.15(13) . . ?
C17 C18 C9 120.95(13) . . ?
C17 C18 C13 118.69(13) . . ?
C1 C19 H19A 120.0 . . ?
C1 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
O2 C20 O3 124.24(14) . . ?
O2 C20 C8 126.61(14) . . ?
O3 C20 C8 109.12(12) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_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 16.993
_oxdiff_exptl_absorpt_empirical_full_min 0.275
####################################################################### 
# 
# 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_624
_database_code_depnum_ccdc_archive 'CCDC 1915418'
loop_
_audit_author_name
_audit_author_address
'Lu Liu'
;East China Normal University
China
;
_audit_update_record             
;
2019-05-11 deposited with the CCDC.	2020-05-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H16 O3)'
_chemical_formula_sum            'C42 H32 O6'
_chemical_formula_weight         632.67
_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      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                   10.5466(2)
_cell_length_b                   10.5720(2)
_cell_length_c                   14.2364(2)
_cell_angle_alpha                88.0490(10)
_cell_angle_beta                 84.2170(10)
_cell_angle_gamma                86.2990(10)
_cell_volume                     1575.36(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.1210
_cell_measurement_theta_min      4.1920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37195
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.357
_diffrn_reflns_theta_min         4.192
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  24.00   1.00    1.00    --    0.00  38.00 -30.00   43
  2  ω      5.00  61.00   1.00    1.00    --    0.00  38.00-180.00   56
  3  ω    -29.00  -3.00   1.00    1.00    --    0.00  82.00-180.00   26
  4  ω     14.00  65.00   1.00    1.00    --    0.00  77.00 120.00   51
  5  ω     53.00  81.00   1.00    1.00    --    0.00  38.00  30.00   28
  6  ω    -14.00  41.00   1.00    1.00    --    0.00  38.00  30.00   55
  7  ω     52.00  88.00   1.00    1.00    --    0.00  19.00 -60.00   36
  8  ω    -18.00  13.00   1.00    1.00    --    0.00  38.00  90.00   31
  9  ω    -23.00  35.00   1.00    1.00    --    0.00  19.00 -60.00   58
 10  ω    -26.00  11.00   1.00    1.00    --    0.00  77.00 120.00   37
 11  ω    -12.00  19.00   1.00    1.00    --    0.00 -38.00 150.00   31
 12  ω    -65.00 -20.00   1.00    1.00    --    0.00 -38.00 150.00   45
 13  ω     23.00  87.00   1.00    1.00    --    0.00  82.00-180.00   64
 14  ω     29.00  79.00   1.00    1.00    --    0.00  38.00  90.00   50
 15  ω     36.00  62.00   1.00    1.00    --    0.00  38.00 -30.00   26
 16  ω      6.00 128.00   1.00    1.00    --   95.80 -82.00 150.00  122
 17  ω     87.00 125.00   1.00    1.00    --   95.80 -82.00 -30.00   38
 18  ω    155.00 181.00   1.00    1.00    --   95.80  79.00 163.51   26
 19  ω      7.00  79.00   1.00    1.00    --   95.80 -82.00 -30.00   72
 20  ω     75.00 132.00   1.00    1.00    --   95.80  45.00 -60.00   57
 21  ω     64.00  90.00   1.00    1.00    --   95.80  79.00 163.51   26
 22  ω     70.00 183.00   1.00    1.00    --   95.80  63.00 164.45  113
 23  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 -30.00   26
 24  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 25  ω     64.00  98.00   1.00    1.00    --   95.80  82.00 -60.00   34
 26  ω     66.00  92.00   1.00    1.00    --   95.80  82.00-120.00   26
 27  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 28  ω     63.00  89.00   1.00    1.00    --   95.80  82.00   0.00   26
 29  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 30  ω     78.00 130.00   1.00    1.00    --   95.80  30.00 120.00   52
 31  ω     86.00 128.00   1.00    1.00    --   95.80 -82.00  30.00   42
 32  ω     24.00 101.00   1.00    1.00    --   95.80 -61.00 150.00   77
 33  ω    158.00 184.00   1.00    1.00    --   95.80  77.00 120.00   26
 34  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 35  ω    125.00 184.00   1.00    1.00    --   95.80  80.00  17.73   59
 36  ω    140.00 166.00   1.00    1.00    --   95.80  60.00  72.97   26
 37  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -90.00   26
 38  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -60.00   26
 39  ω     52.00 103.00   1.00    1.00    --   95.80 -82.00  90.00   51
 40  ω     76.00 182.00   1.00    1.00    --   95.80  45.00 120.00  106
 41  ω     71.00  96.00   1.00    1.00    --   95.80  61.00 -60.00   25
 42  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 43  ω     63.00 132.00   1.00    1.00    --   95.80  82.00  30.00   69
 44  ω     64.00  97.00   1.00    1.00    --   95.80  82.00  60.00   33
 45  ω     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 46  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 47  ω    136.00 162.00   1.00    1.00    --   95.80  82.00-150.00   26
 48  ω     64.00  89.00   1.00    1.00    --   95.80  82.00  90.00   25
 49  ω    108.00 171.00   1.00    1.00    --   95.80  61.00-120.00   63
 50  ω     43.00  87.00   1.00    1.00    --   95.80 -82.00 -60.00   44
 51  ω     97.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   31
 52  ω     64.00 101.00   1.00    1.00    --   95.80  80.00  17.73   37
 53  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 54  ω     76.00 112.00   1.00    1.00    --   95.80  45.00 150.00   36
 55  ω    134.00 178.00   1.00    1.00    --   95.80  45.00 150.00   44
 56  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 57  ω     71.00 100.00   1.00    1.00    --   95.80  61.00-120.00   29
 58  ω     65.00 177.00   1.00    1.00    --   95.80  77.00-180.00  112
 59  ω     75.00 173.00   1.00    1.00    --   95.80  45.00   0.00   98
 60  ω     77.00 181.00   1.00    1.00    --   95.80  45.00 -30.00  104
 61  ω     68.00 118.00   1.00    1.00    --   95.80  68.00   3.15   50
 62  ω     71.00 105.00   1.00    1.00    --   95.80  60.00  72.97   34
 63  ω     70.00 182.00   1.00    1.00    --   95.80  63.00-106.81  112
 64  ω     12.00 119.00   1.00    1.00    --   95.80 -82.00 -90.00  107
 65  ω     69.00 184.00   1.00    1.00    --   95.80  67.00-147.14  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0634768000
_diffrn_orient_matrix_UB_12      0.0166251000
_diffrn_orient_matrix_UB_13      -0.0928414000
_diffrn_orient_matrix_UB_21      0.1307633000
_diffrn_orient_matrix_UB_22      -0.0266556000
_diffrn_orient_matrix_UB_23      -0.0566705000
_diffrn_orient_matrix_UB_31      -0.0225696000
_diffrn_orient_matrix_UB_32      -0.1426635000
_diffrn_orient_matrix_UB_33      0.0028606000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6047
_reflns_number_total             6305
_reflns_odcompleteness_completeness 99.61
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.250
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.058
_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)+(0.0477P)²+0.7482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1018
_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:
 C18(H18), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C24(H24), C25(H25), C26(H26), C27(H27), C31(H31), C32(H32), C34(H34),
  C35(H35), C36(H36), C37(H37)
2.c X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C42(H42A,H42B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C41(H41A,H41B,H41C)
;
_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
O1 O 0.20866(9) -0.03659(8) 0.34630(6) 0.0215(2) Uani 1 1 d . . . . .
O2 O 0.06660(8) 0.20793(9) 0.40917(6) 0.02027(19) Uani 1 1 d . . . . .
O3 O 0.20176(9) 0.19594(10) 0.52141(6) 0.0277(2) Uani 1 1 d . . . . .
C1 C 0.18236(11) 0.03889(11) 0.28309(8) 0.0167(2) Uani 1 1 d . . . . .
C2 C 0.08002(11) 0.01759(12) 0.22213(8) 0.0171(2) Uani 1 1 d . . . . .
C3 C 0.01697(12) -0.09476(13) 0.23315(9) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.039994 -0.155813 0.277931 0.026 Uiso 1 1 calc R . . . .
C4 C -0.08002(13) -0.11581(13) 0.17750(10) 0.0247(3) Uani 1 1 d . . . . .
H4 H -0.120835 -0.191452 0.184137 0.030 Uiso 1 1 calc R . . . .
C5 C -0.11589(12) -0.02342(14) 0.11184(10) 0.0250(3) Uani 1 1 d . . . . .
H5 H -0.181271 -0.037311 0.074904 0.030 Uiso 1 1 calc R . . . .
C6 C -0.05507(12) 0.08909(13) 0.10100(9) 0.0229(3) Uani 1 1 d . . . . .
H6 H -0.080476 0.150505 0.057250 0.027 Uiso 1 1 calc R . . . .
C7 C 0.04427(12) 0.11119(12) 0.15529(9) 0.0186(2) Uani 1 1 d . . . . .
C8 C 0.10891(12) 0.22975(12) 0.14525(9) 0.0202(3) Uani 1 1 d . . . . .
H8 H 0.082067 0.291687 0.102388 0.024 Uiso 1 1 calc R . . . .
C9 C 0.20480(12) 0.25245(12) 0.19514(9) 0.0186(2) Uani 1 1 d . . . . .
H9 H 0.239454 0.331275 0.187645 0.022 Uiso 1 1 calc R . . . .
C10 C 0.25988(11) 0.15685(11) 0.26305(8) 0.0166(2) Uani 1 1 d . . . . .
C11 C 0.39382(12) 0.10322(12) 0.22198(9) 0.0189(2) Uani 1 1 d . . . . .
C12 C 0.47948(12) 0.10468(11) 0.29715(9) 0.0181(2) Uani 1 1 d . . . . .
C13 C 0.60567(12) 0.05515(12) 0.29630(10) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.646642 0.016397 0.242891 0.026 Uiso 1 1 calc R . . . .
C14 C 0.66881(12) 0.06471(12) 0.37640(10) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.752246 0.030645 0.377129 0.029 Uiso 1 1 calc R . . . .
C15 C 0.60835(13) 0.12485(13) 0.45565(10) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.651700 0.130232 0.508981 0.030 Uiso 1 1 calc R . . . .
C16 C 0.48356(12) 0.17712(12) 0.45603(9) 0.0211(3) Uani 1 1 d . . . . .
H16 H 0.444010 0.218996 0.508556 0.025 Uiso 1 1 calc R . . . .
C17 C 0.41918(11) 0.16550(11) 0.37634(9) 0.0176(2) Uani 1 1 d . . . . .
C18 C 0.28634(11) 0.21687(11) 0.35764(8) 0.0165(2) Uani 1 1 d . . . . .
H18 H 0.291727 0.308044 0.344403 0.020 Uiso 1 1 calc R . . . .
C19 C 0.18372(12) 0.20314(12) 0.43933(9) 0.0178(2) Uani 1 1 d . . . . .
C20 C -0.03719(12) 0.19983(15) 0.48339(10) 0.0269(3) Uani 1 1 d . . . . .
H20A H -0.116694 0.200496 0.455894 0.040 Uiso 1 1 calc GR . . . .
H20B H -0.038384 0.270985 0.523675 0.040 Uiso 1 1 calc GR . . . .
H20C H -0.025320 0.122652 0.519822 0.040 Uiso 1 1 calc GR . . . .
C21 C 0.42003(14) 0.06104(14) 0.13506(10) 0.0274(3) Uani 1 1 d . . . . .
H21A H 0.501553 0.027076 0.115426 0.033 Uiso 1 1 calc R . . . .
H21B H 0.356868 0.065425 0.093742 0.033 Uiso 1 1 calc R . . . .
O4 O 0.44412(8) 0.43228(8) 0.23220(6) 0.02045(19) Uani 1 1 d . . . . .
O5 O 0.17272(9) 0.55370(11) 0.35410(7) 0.0302(2) Uani 1 1 d . . . . .
O6 O 0.36043(9) 0.60006(9) 0.40165(6) 0.0224(2) Uani 1 1 d . . . . .
C22 C 0.31964(11) 0.67228(12) 0.24934(8) 0.0167(2) Uani 1 1 d . . . . .
H22 H 0.298247 0.762489 0.260363 0.020 Uiso 1 1 calc R . . . .
C23 C 0.26164(12) 0.64049(11) 0.16093(9) 0.0174(2) Uani 1 1 d . . . . .
C24 C 0.13625(12) 0.61575(12) 0.15010(9) 0.0207(3) Uani 1 1 d . . . . .
H24 H 0.075133 0.614266 0.201929 0.025 Uiso 1 1 calc R . . . .
C25 C 0.10423(13) 0.59332(13) 0.06026(10) 0.0244(3) Uani 1 1 d . . . . .
H25 H 0.020651 0.576586 0.051942 0.029 Uiso 1 1 calc R . . . .
C26 C 0.19516(14) 0.59544(14) -0.01761(10) 0.0267(3) Uani 1 1 d . . . . .
H26 H 0.171918 0.579460 -0.077185 0.032 Uiso 1 1 calc R . . . .
C27 C 0.32069(13) 0.62130(13) -0.00708(9) 0.0240(3) Uani 1 1 d . . . . .
H27 H 0.381560 0.623512 -0.059037 0.029 Uiso 1 1 calc R . . . .
C28 C 0.35295(12) 0.64380(12) 0.08326(9) 0.0185(2) Uani 1 1 d . . . . .
C29 C 0.47820(12) 0.67090(12) 0.11244(9) 0.0184(2) Uani 1 1 d . . . . .
C30 C 0.46623(11) 0.65670(11) 0.22208(8) 0.0159(2) Uani 1 1 d . . . . .
C31 C 0.54041(12) 0.75064(12) 0.26679(9) 0.0182(2) Uani 1 1 d . . . . .
H31 H 0.504454 0.832681 0.274881 0.022 Uiso 1 1 calc R . . . .
C32 C 0.65536(12) 0.72204(12) 0.29545(8) 0.0184(2) Uani 1 1 d . . . . .
H32 H 0.697880 0.785155 0.320848 0.022 Uiso 1 1 calc R . . . .
C33 C 0.71658(11) 0.59452(12) 0.28815(8) 0.0169(2) Uani 1 1 d . . . . .
C34 C 0.84211(12) 0.56743(13) 0.31061(9) 0.0198(3) Uani 1 1 d . . . . .
H34 H 0.888506 0.632242 0.329634 0.024 Uiso 1 1 calc R . . . .
C35 C 0.89784(12) 0.44527(13) 0.30480(9) 0.0214(3) Uani 1 1 d . . . . .
H35 H 0.982014 0.429212 0.318077 0.026 Uiso 1 1 calc R . . . .
C36 C 0.82837(12) 0.34628(12) 0.27914(9) 0.0204(3) Uani 1 1 d . . . . .
H36 H 0.865777 0.264235 0.275973 0.025 Uiso 1 1 calc R . . . .
C37 C 0.70309(12) 0.37064(12) 0.25833(8) 0.0185(2) Uani 1 1 d . . . . .
H37 H 0.655832 0.304462 0.242762 0.022 Uiso 1 1 calc R . . . .
C38 C 0.64818(11) 0.49395(12) 0.26075(8) 0.0160(2) Uani 1 1 d . . . . .
C39 C 0.51379(11) 0.51833(11) 0.23951(8) 0.0156(2) Uani 1 1 d . . . . .
C40 C 0.27429(12) 0.60010(12) 0.33883(9) 0.0186(2) Uani 1 1 d . . . . .
C41 C 0.32699(14) 0.53654(14) 0.49145(9) 0.0263(3) Uani 1 1 d . . . . .
H41A H 0.335113 0.446432 0.483717 0.040 Uiso 1 1 calc GR . . . .
H41B H 0.240473 0.561639 0.513995 0.040 Uiso 1 1 calc GR . . . .
H41C H 0.383194 0.559373 0.536253 0.040 Uiso 1 1 calc GR . . . .
C42 C 0.58369(13) 0.69711(14) 0.05864(10) 0.0263(3) Uani 1 1 d . . . . .
H42A H 0.584229 0.700048 -0.006760 0.032 Uiso 1 1 calc R . . . .
H42B H 0.657215 0.712565 0.086272 0.032 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
O1 C1 1.2232(15) . ?
O2 C19 1.3453(15) . ?
O2 C20 1.4473(15) . ?
O3 C19 1.2018(16) . ?
C1 C2 1.4840(17) . ?
C1 C10 1.5380(16) . ?
C2 C3 1.3950(18) . ?
C2 C7 1.4096(17) . ?
C3 H3 0.9300 . ?
C3 C4 1.3886(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.3989(18) . ?
C7 C8 1.4610(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.3313(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.5048(16) . ?
C10 C11 1.5529(16) . ?
C10 C18 1.5655(16) . ?
C11 C12 1.4694(17) . ?
C11 C21 1.3264(19) . ?
C12 C13 1.3974(17) . ?
C12 C17 1.3932(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.3938(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.3923(17) . ?
C17 C18 1.5151(16) . ?
C18 H18 0.9800 . ?
C18 C19 1.5166(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9300 . ?
C21 H21B 0.9300 . ?
O4 C39 1.2192(15) . ?
O5 C40 1.2037(16) . ?
O6 C40 1.3375(15) . ?
O6 C41 1.4460(15) . ?
C22 H22 0.9800 . ?
C22 C23 1.5106(16) . ?
C22 C30 1.5552(16) . ?
C22 C40 1.5140(17) . ?
C23 C24 1.3890(17) . ?
C23 C28 1.3922(17) . ?
C24 H24 0.9300 . ?
C24 C25 1.3872(18) . ?
C25 H25 0.9300 . ?
C25 C26 1.391(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.3926(19) . ?
C27 H27 0.9300 . ?
C27 C28 1.3949(18) . ?
C28 C29 1.4722(17) . ?
C29 C30 1.5561(16) . ?
C29 C42 1.3247(18) . ?
C30 C31 1.4991(16) . ?
C30 C39 1.5358(17) . ?
C31 H31 0.9300 . ?
C31 C32 1.3310(18) . ?
C32 H32 0.9300 . ?
C32 C33 1.4590(17) . ?
C33 C34 1.4026(17) . ?
C33 C38 1.4096(17) . ?
C34 H34 0.9300 . ?
C34 C35 1.3855(19) . ?
C35 H35 0.9300 . ?
C35 C36 1.3944(19) . ?
C36 H36 0.9300 . ?
C36 C37 1.3890(18) . ?
C37 H37 0.9300 . ?
C37 C38 1.3919(18) . ?
C38 C39 1.4835(16) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9300 . ?
C42 H42B 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
C19 O2 C20 114.79(10) . . ?
O1 C1 C2 121.72(11) . . ?
O1 C1 C10 119.73(11) . . ?
C2 C1 C10 118.51(10) . . ?
C3 C2 C1 119.41(11) . . ?
C3 C2 C7 120.10(11) . . ?
C7 C2 C1 120.48(11) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.25(12) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.77(12) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.52(12) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.56(12) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C8 119.91(11) . . ?
C6 C7 C2 118.78(12) . . ?
C6 C7 C8 121.29(12) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.47(12) . . ?
C9 C8 H8 118.8 . . ?
C8 C9 H9 118.4 . . ?
C8 C9 C10 123.24(11) . . ?
C10 C9 H9 118.4 . . ?
C1 C10 C11 104.31(9) . . ?
C1 C10 C18 110.55(9) . . ?
C9 C10 C1 114.34(10) . . ?
C9 C10 C11 110.54(10) . . ?
C9 C10 C18 112.70(10) . . ?
C11 C10 C18 103.53(9) . . ?
C12 C11 C10 107.55(10) . . ?
C21 C11 C10 124.15(12) . . ?
C21 C11 C12 128.26(12) . . ?
C13 C12 C11 128.40(12) . . ?
C17 C12 C11 111.10(11) . . ?
C17 C12 C13 120.51(12) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 118.93(12) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.54(12) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.75(12) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.79(12) . . ?
C17 C16 H16 120.6 . . ?
C12 C17 C18 110.30(11) . . ?
C16 C17 C12 120.46(11) . . ?
C16 C17 C18 129.16(11) . . ?
C10 C18 H18 106.5 . . ?
C17 C18 C10 105.43(10) . . ?
C17 C18 H18 106.5 . . ?
C17 C18 C19 115.55(10) . . ?
C19 C18 C10 115.69(10) . . ?
C19 C18 H18 106.5 . . ?
O2 C19 C18 111.40(10) . . ?
O3 C19 O2 123.16(11) . . ?
O3 C19 C18 125.31(11) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C21 H21A 120.0 . . ?
C11 C21 H21B 120.0 . . ?
H21A C21 H21B 120.0 . . ?
C40 O6 C41 116.02(10) . . ?
C23 C22 H22 107.2 . . ?
C23 C22 C30 104.53(9) . . ?
C23 C22 C40 116.31(10) . . ?
C30 C22 H22 107.2 . . ?
C40 C22 H22 107.2 . . ?
C40 C22 C30 114.04(10) . . ?
C24 C23 C22 128.98(11) . . ?
C24 C23 C28 120.77(11) . . ?
C28 C23 C22 110.19(10) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.52(12) . . ?
C25 C24 H24 120.7 . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 121.05(12) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.54(12) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 120.8 . . ?
C26 C27 C28 118.42(12) . . ?
C28 C27 H27 120.8 . . ?
C23 C28 C27 120.69(12) . . ?
C23 C28 C29 110.76(11) . . ?
C27 C28 C29 128.55(12) . . ?
C28 C29 C30 106.20(10) . . ?
C42 C29 C28 128.58(12) . . ?
C42 C29 C30 125.17(12) . . ?
C22 C30 C29 103.10(9) . . ?
C31 C30 C22 113.82(10) . . ?
C31 C30 C29 112.54(10) . . ?
C31 C30 C39 113.44(10) . . ?
C39 C30 C22 109.72(10) . . ?
C39 C30 C29 103.24(9) . . ?
C30 C31 H31 118.5 . . ?
C32 C31 C30 123.02(11) . . ?
C32 C31 H31 118.5 . . ?
C31 C32 H32 119.1 . . ?
C31 C32 C33 121.90(11) . . ?
C33 C32 H32 119.1 . . ?
C34 C33 C32 121.65(11) . . ?
C34 C33 C38 118.25(12) . . ?
C38 C33 C32 120.07(11) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.80(12) . . ?
C35 C34 H34 119.6 . . ?
C34 C35 H35 119.8 . . ?
C34 C35 C36 120.35(12) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 120.1 . . ?
C37 C36 C35 119.77(12) . . ?
C37 C36 H36 120.1 . . ?
C36 C37 H37 119.9 . . ?
C36 C37 C38 120.10(12) . . ?
C38 C37 H37 119.9 . . ?
C33 C38 C39 119.72(11) . . ?
C37 C38 C33 120.68(11) . . ?
C37 C38 C39 119.51(11) . . ?
O4 C39 C30 120.50(11) . . ?
O4 C39 C38 121.88(11) . . ?
C38 C39 C30 117.56(10) . . ?
O5 C40 O6 123.94(12) . . ?
O5 C40 C22 125.43(12) . . ?
O6 C40 C22 110.54(10) . . ?
O6 C41 H41A 109.5 . . ?
O6 C41 H41B 109.5 . . ?
O6 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C29 C42 H42A 120.0 . . ?
C29 C42 H42B 120.0 . . ?
H42A C42 H42B 120.0 . . ?

_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 4.574
_oxdiff_exptl_absorpt_empirical_full_min 0.490
