# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_2837
_database_code_depnum_ccdc_archive 'CCDC 1914741'
loop_
_audit_author_name
_audit_author_address
'Yan Geng'
;Shandong Normal University
China
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-08-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H25 B F2 O4'
_chemical_formula_sum            'C25 H25 B F2 O4'
_chemical_formula_weight         438.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1 B1 F1'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.8130(6)
_cell_length_b                   9.3837(6)
_cell_length_c                   16.3462(11)
_cell_angle_alpha                101.355(6)
_cell_angle_beta                 97.002(6)
_cell_angle_gamma                104.391(6)
_cell_volume                     1119.52(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2430
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6480
_cell_measurement_theta_min      10.3100
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7135
_diffrn_reflns_theta_full        67.05
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         5.01
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9784
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00  80.00   1.00    1.10    --   54.00 -37.00 -30.00   69
  2  ω     36.00 124.00   1.00    1.10    --   54.00  37.00   0.00   88
  3  ω    142.00 168.00   1.00    1.10    --  108.00  63.00 -60.00   26
  4  ω    117.00 142.00   1.00    1.10    --  108.00 -25.00 -60.00   25
  5  ω     93.00 127.00   1.00    1.10    --  108.00 -37.00 -60.00   34
  6  ω     88.00 114.00   1.00    1.10    --  108.00-111.00  30.00   26
  7  ω     65.00 113.00   1.00    1.10    --  108.00-111.00 -90.00   48
  8  ω     55.00  81.00   1.00    1.10    --   54.00-125.00-180.00   26
  9  ω     38.00 127.00   1.00    1.10    --  108.00 -50.00-180.00   89
 10  ω     51.00  79.00   1.00    1.10    --  108.00 -37.00 -60.00   28
 11  ω     38.00 131.00   1.00    1.10    --  108.00 -77.00 -60.00   93
 12  ω     44.00 111.00   1.00    1.10    --   54.00-125.00 -30.00   67
 13  ω     39.00 129.00   1.00    1.10    --  108.00 -50.00  60.00   90
 14  ω     88.00 155.00   1.00    1.10    --  108.00  63.00 -30.00   67
 15  ω     37.00 145.00   1.00    1.10    --  108.00 -91.00  90.00  108
 16  ω     36.00 175.00   1.00    1.10    --  108.00  12.00 -60.00  139
 17  ω     35.00  86.00   1.00    1.10    --  108.00 -25.00 -60.00   51
 18  ω     23.00  48.00   1.00    1.10    --   54.00 -57.00 -60.00   25
 19  ω     -2.00  30.00   1.00    1.00    --    0.00 -77.00-120.00   32
 20  ω    -10.00  80.00   1.00    1.10    --   54.00 -37.00-180.00   90
 21  ω     24.00  72.00   1.00    1.10    --   54.00-125.00-150.00   48
 22  ω    -69.00 -13.00   1.00    1.00    --    0.00 -77.00-120.00   56
 23  ω     25.00  70.00   1.00    1.00    --    0.00  77.00 -60.00   45
 24  ω     31.00 104.00   1.00    1.10    --   54.00  37.00 150.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1340833000
_diffrn_orient_matrix_UB_12      -0.1424427000
_diffrn_orient_matrix_UB_13      0.0116589000
_diffrn_orient_matrix_UB_21      0.1338124000
_diffrn_orient_matrix_UB_22      -0.0045540000
_diffrn_orient_matrix_UB_23      0.0762372000
_diffrn_orient_matrix_UB_31      -0.0833178000
_diffrn_orient_matrix_UB_32      0.1005777000
_diffrn_orient_matrix_UB_33      0.0600130000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3093
_reflns_number_total             4005
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.2060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C12(H12), C16(H16), C17(H17),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
B1 B 1.2894(3) 0.4667(2) 0.30378(14) 0.0542(6) Uani 1 1 d . . .
C1 C 1.2476(3) 0.4581(3) -0.21090(15) 0.0715(6) Uani 1 1 d . . .
H1A H 1.2004 0.5431 -0.1964 0.107 Uiso 1 1 calc . . GR
H1B H 1.2415 0.4312 -0.2712 0.107 Uiso 1 1 calc . . GR
H1C H 1.3704 0.4843 -0.1829 0.107 Uiso 1 1 calc . . GR
C2 C 1.1448(2) 0.3426(2) -0.10059(12) 0.0470(4) Uani 1 1 d . . .
C3 C 1.0520(3) 0.2111(2) -0.08028(12) 0.0501(5) Uani 1 1 d . . .
H3 H 0.9933 0.1255 -0.1232 0.060 Uiso 1 1 calc . . R
C4 C 1.0466(2) 0.20714(19) 0.00246(11) 0.0453(4) Uani 1 1 d . . .
H4 H 0.9840 0.1182 0.0149 0.054 Uiso 1 1 calc . . R
C5 C 1.1327(2) 0.33326(18) 0.06904(11) 0.0404(4) Uani 1 1 d . . .
C6 C 1.2263(3) 0.46362(19) 0.04718(12) 0.0494(5) Uani 1 1 d . . .
H6 H 1.2862 0.5491 0.0900 0.059 Uiso 1 1 calc . . R
C7 C 1.2323(3) 0.4693(2) -0.03602(12) 0.0516(5) Uani 1 1 d . . .
H7 H 1.2949 0.5579 -0.0488 0.062 Uiso 1 1 calc . . R
C8 C 1.1361(2) 0.32807(18) 0.15794(11) 0.0408(4) Uani 1 1 d . . .
C9 C 1.0039(2) 0.22815(18) 0.18616(10) 0.0392(4) Uani 1 1 d . . .
C10 C 0.8257(2) 0.15475(18) 0.14263(11) 0.0402(4) Uani 1 1 d . . .
H10 H 0.7779 0.1656 0.0900 0.048 Uiso 1 1 calc . . R
C11 C 0.7323(2) 0.06395(18) 0.18983(10) 0.0386(4) Uani 1 1 d . . .
C12 C 0.8525(2) 0.07332(19) 0.26242(10) 0.0411(4) Uani 1 1 d . . .
H12 H 0.8261 0.0202 0.3038 0.049 Uiso 1 1 calc . . R
C13 C 1.0202(2) 0.17506(19) 0.26389(10) 0.0406(4) Uani 1 1 d . . .
C14 C 1.1698(2) 0.21247(19) 0.32917(10) 0.0420(4) Uani 1 1 d . . .
C15 C 1.1918(2) 0.1185(2) 0.38846(10) 0.0430(4) Uani 1 1 d . . .
C16 C 1.1294(2) -0.0388(2) 0.36428(11) 0.0478(4) Uani 1 1 d . . .
H16 H 1.0669 -0.0851 0.3095 0.057 Uiso 1 1 calc . . R
C17 C 1.1581(3) -0.1274(2) 0.41953(12) 0.0525(5) Uani 1 1 d . . .
H17 H 1.1162 -0.2323 0.4020 0.063 Uiso 1 1 calc . . R
C18 C 1.2499(3) -0.0588(2) 0.50143(11) 0.0519(5) Uani 1 1 d . . .
C19 C 1.3136(3) 0.0988(2) 0.52699(12) 0.0572(5) Uani 1 1 d . . .
H19 H 1.3743 0.1449 0.5821 0.069 Uiso 1 1 calc . . R
C20 C 1.2870(3) 0.1856(2) 0.47118(11) 0.0515(5) Uani 1 1 d . . .
H20 H 1.3325 0.2904 0.4883 0.062 Uiso 1 1 calc . . R
C21 C 1.2240(4) -0.2949(3) 0.54070(16) 0.0907(9) Uani 1 1 d . . .
H21A H 1.0953 -0.3257 0.5261 0.136 Uiso 1 1 calc . . GR
H21B H 1.2604 -0.3322 0.5887 0.136 Uiso 1 1 calc . . GR
H21C H 1.2735 -0.3353 0.4934 0.136 Uiso 1 1 calc . . GR
C22 C 0.5341(2) -0.0203(2) 0.16765(11) 0.0428(4) Uani 1 1 d . . .
C23 C 0.4760(3) -0.1079(3) 0.23374(13) 0.0676(6) Uani 1 1 d . . .
H23A H 0.5457 -0.1781 0.2379 0.101 Uiso 1 1 calc . . GR
H23B H 0.3510 -0.1622 0.2171 0.101 Uiso 1 1 calc . . GR
H23C H 0.4950 -0.0383 0.2878 0.101 Uiso 1 1 calc . . GR
C24 C 0.4277(3) 0.0957(2) 0.16288(16) 0.0671(6) Uani 1 1 d . . .
H24A H 0.4516 0.1659 0.2170 0.101 Uiso 1 1 calc . . GR
H24B H 0.3016 0.0443 0.1479 0.101 Uiso 1 1 calc . . GR
H24C H 0.4632 0.1495 0.1207 0.101 Uiso 1 1 calc . . GR
C25 C 0.4948(3) -0.1328(2) 0.08142(12) 0.0530(5) Uani 1 1 d . . .
H25A H 0.5394 -0.0808 0.0400 0.079 Uiso 1 1 calc . . GR
H25B H 0.3675 -0.1776 0.0645 0.079 Uiso 1 1 calc . . GR
H25C H 0.5529 -0.2107 0.0857 0.079 Uiso 1 1 calc . . GR
F1 F 1.44835(18) 0.57595(13) 0.33484(8) 0.0772(4) Uani 1 1 d . . .
F2 F 1.14347(18) 0.51375(13) 0.32318(8) 0.0714(4) Uani 1 1 d . . .
O1 O 1.1442(2) 0.33244(16) -0.18441(8) 0.0647(4) Uani 1 1 d . . .
O2 O 1.27680(16) 0.42321(13) 0.20987(8) 0.0497(3) Uani 1 1 d . . .
O3 O 1.30164(16) 0.33658(14) 0.34140(8) 0.0512(3) Uani 1 1 d . . .
O4 O 1.2874(2) -0.13379(17) 0.56141(9) 0.0708(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.364(2) . ?
B1 F2 1.370(3) . ?
B1 O2 1.493(3) . ?
B1 O3 1.489(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.430(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.386(3) . ?
C2 O1 1.354(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(2) . ?
C5 C6 1.396(2) . ?
C5 C8 1.461(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(2) . ?
C8 O2 1.3086(19) . ?
C9 C10 1.417(2) . ?
C9 C13 1.456(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(2) . ?
C11 C12 1.395(2) . ?
C11 C22 1.515(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.411(2) . ?
C13 C14 1.404(2) . ?
C14 C15 1.455(2) . ?
C14 O3 1.311(2) . ?
C15 C16 1.392(2) . ?
C15 C20 1.401(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(3) . ?
C18 C19 1.397(3) . ?
C18 O4 1.359(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.367(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 O4 1.425(3) . ?
C22 C23 1.527(2) . ?
C22 C24 1.533(3) . ?
C22 C25 1.531(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
F1 B1 F2 113.11(18) . . ?
F1 B1 O2 106.54(17) . . ?
F1 B1 O3 106.27(18) . . ?
F2 B1 O2 110.31(18) . . ?
F2 B1 O3 110.22(17) . . ?
O3 B1 O2 110.25(16) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
C7 C2 C3 119.34(17) . . ?
O1 C2 C3 115.15(16) . . ?
O1 C2 C7 125.49(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.29(16) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.77(16) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C8 122.28(15) . . ?
C6 C5 C4 116.93(16) . . ?
C6 C5 C8 120.67(15) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 121.90(16) . . ?
C7 C6 H6 119.0 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.76(17) . . ?
C6 C7 H7 120.1 . . ?
C9 C8 C5 123.72(15) . . ?
O2 C8 C5 114.14(14) . . ?
O2 C8 C9 122.12(16) . . ?
C8 C9 C10 126.26(16) . . ?
C8 C9 C13 127.99(15) . . ?
C10 C9 C13 105.74(14) . . ?
C9 C10 H10 124.8 . . ?
C11 C10 C9 110.38(15) . . ?
C11 C10 H10 124.8 . . ?
C10 C11 C12 107.13(15) . . ?
C10 C11 C22 125.50(15) . . ?
C12 C11 C22 127.27(15) . . ?
C11 C12 H12 124.9 . . ?
C11 C12 C13 110.10(15) . . ?
C13 C12 H12 124.9 . . ?
C12 C13 C9 106.58(14) . . ?
C14 C13 C9 128.85(16) . . ?
C14 C13 C12 124.57(16) . . ?
C13 C14 C15 123.39(15) . . ?
O3 C14 C13 122.04(16) . . ?
O3 C14 C15 114.57(15) . . ?
C16 C15 C14 121.87(15) . . ?
C16 C15 C20 118.13(17) . . ?
C20 C15 C14 119.91(16) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.61(16) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.41(18) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C19 119.90(18) . . ?
O4 C18 C17 124.90(18) . . ?
O4 C18 C19 115.20(17) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.20(17) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.73(18) . . ?
C19 C20 H20 119.6 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C21 H21A 109.5 . . ?
O4 C21 H21B 109.5 . . ?
O4 C21 H21C 109.5 . . ?
C11 C22 C23 111.51(15) . . ?
C11 C22 C24 108.18(15) . . ?
C11 C22 C25 109.66(14) . . ?
C23 C22 C24 109.66(17) . . ?
C23 C22 C25 108.41(16) . . ?
C25 C22 C24 109.40(16) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C2 O1 C1 119.13(16) . . ?
C8 O2 B1 123.85(15) . . ?
C14 O3 B1 123.87(15) . . ?
C18 O4 C21 118.57(17) . . ?

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
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C3 C2 O1 C1 -175.17(18) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C8 -176.64(17) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C4 C5 C8 C9 -26.8(3) . . . . ?
C4 C5 C8 O2 151.68(17) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C5 C8 C9 C10 -21.7(3) . . . . ?
C5 C8 C9 C13 156.64(17) . . . . ?
C5 C8 O2 B1 164.22(16) . . . . ?
C6 C5 C8 C9 157.31(17) . . . . ?
C6 C5 C8 O2 -24.2(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C7 C2 O1 C1 3.2(3) . . . . ?
C8 C5 C6 C7 176.92(17) . . . . ?
C8 C9 C10 C11 -179.90(16) . . . . ?
C8 C9 C13 C12 -178.41(17) . . . . ?
C8 C9 C13 C14 1.0(3) . . . . ?
C9 C8 O2 B1 -17.3(3) . . . . ?
C9 C10 C11 C12 -2.57(19) . . . . ?
C9 C10 C11 C22 174.04(16) . . . . ?
C9 C13 C14 C15 -158.77(17) . . . . ?
C9 C13 C14 O3 21.3(3) . . . . ?
C10 C9 C13 C12 0.20(18) . . . . ?
C10 C9 C13 C14 179.65(17) . . . . ?
C10 C11 C12 C13 2.7(2) . . . . ?
C10 C11 C22 C23 -179.58(18) . . . . ?
C10 C11 C22 C24 -58.9(2) . . . . ?
C10 C11 C22 C25 60.3(2) . . . . ?
C11 C12 C13 C9 -1.8(2) . . . . ?
C11 C12 C13 C14 178.73(16) . . . . ?
C12 C11 C22 C23 -3.7(3) . . . . ?
C12 C11 C22 C24 117.0(2) . . . . ?
C12 C11 C22 C25 -123.74(19) . . . . ?
C12 C13 C14 C15 20.6(3) . . . . ?
C12 C13 C14 O3 -159.31(17) . . . . ?
C13 C9 C10 C11 1.46(19) . . . . ?
C13 C14 C15 C16 34.0(3) . . . . ?
C13 C14 C15 C20 -149.66(18) . . . . ?
C13 C14 O3 B1 15.6(3) . . . . ?
C14 C15 C16 C17 176.89(17) . . . . ?
C14 C15 C20 C19 -178.06(18) . . . . ?
C15 C14 O3 B1 -164.34(16) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C16 C17 C18 O4 -179.57(18) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C17 C18 O4 C21 -2.1(3) . . . . ?
C18 C19 C20 C15 1.6(3) . . . . ?
C19 C18 O4 C21 178.9(2) . . . . ?
C20 C15 C16 C17 0.5(3) . . . . ?
C22 C11 C12 C13 -173.84(16) . . . . ?
F1 B1 O2 C8 -175.21(16) . . . . ?
F1 B1 O3 C14 176.66(15) . . . . ?
F2 B1 O2 C8 -52.1(2) . . . . ?
F2 B1 O3 C14 53.8(2) . . . . ?
O1 C2 C3 C4 178.68(17) . . . . ?
O1 C2 C7 C6 -178.30(18) . . . . ?
O2 B1 O3 C14 -68.3(2) . . . . ?
O2 C8 C9 C10 159.97(17) . . . . ?
O2 C8 C9 C13 -21.7(3) . . . . ?
O3 B1 O2 C8 69.9(2) . . . . ?
O3 C14 C15 C16 -146.11(17) . . . . ?
O3 C14 C15 C20 30.2(2) . . . . ?
O4 C18 C19 C20 178.58(19) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.010
_oxdiff_exptl_absorpt_empirical_full_min 0.825

####################################################################### 
# 
# 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_3232
_database_code_depnum_ccdc_archive 'CCDC 1914742'
loop_
_audit_author_name
_audit_author_address
'Yan Geng'
;Shandong Normal University
China
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C31 H26 O2'
_chemical_formula_sum            'C31 H26 O2'
_chemical_formula_weight         430.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.6358(7)
_cell_length_b                   10.2626(6)
_cell_length_c                   12.5875(8)
_cell_angle_alpha                75.480(5)
_cell_angle_beta                 73.810(6)
_cell_angle_gamma                83.749(6)
_cell_volume                     1156.20(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3338
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9460
_cell_measurement_theta_min      7.9690
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0295
_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       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7623
_diffrn_reflns_theta_full        71.26
_diffrn_reflns_theta_max         71.26
_diffrn_reflns_theta_min         3.76
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9942
_diffrn_measured_fraction_theta_max 0.9657
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00  39.00   1.00    1.00    --    0.00 -19.00 -30.00   28
  2  ω     28.00 122.00   1.00    1.00    --   54.00  37.00  30.00   94
  3  ω     79.00 157.00   1.00    1.00    --  108.00  77.00 -60.00   78
  4  ω    130.00 177.00   1.00    1.00    --  108.00  37.00 -90.00   47
  5  ω     99.00 129.00   1.00    1.00    --  108.00 -50.00 -60.00   30
  6  ω     90.00 116.00   1.00    1.00    --  108.00-111.00 -90.00   26
  7  ω     58.00 107.00   1.00    1.00    --   54.00-125.00-120.00   49
  8  ω     61.00  96.00   1.00    1.00    --  108.00 -50.00 -60.00   35
  9  ω     59.00 128.00   1.00    1.00    --  108.00 -77.00-120.00   69
 10  ω     43.00 128.00   1.00    1.00    --  108.00 -50.00  30.00   85
 11  ω     63.00 113.00   1.00    1.00    --  108.00 -77.00  60.00   50
 12  ω     35.00  85.00   1.00    1.00    --   54.00-125.00  90.00   50
 13  ω     36.00 112.00   1.00    1.00    --  108.00-111.00  60.00   76
 14  ω     36.00 134.00   1.00    1.00    --  108.00   0.00 120.00   98
 15  ω     79.00 169.00   1.00    1.00    --  108.00  77.00 -30.00   90
 16  ω     96.00 121.00   1.00    1.00    --   54.00  57.00 -90.00   25
 17  ω     90.00 123.00   1.00    1.00    --  108.00  37.00 -90.00   33
 18  ω     41.00 125.00   1.00    1.00    --  108.00 -50.00-180.00   84
 19  ω     40.00 108.00   1.00    1.00    --  108.00-111.00-150.00   68
 20  ω    -15.00  35.00   1.00    1.00    --   54.00 -77.00  90.00   50
 21  ω    -15.00  74.00   1.00    1.00    --   54.00 -57.00 120.00   89
 22  ω     43.00  69.00   1.00    1.00    --    0.00  57.00 150.00   26
 23  ω      0.00  33.00   1.00    1.00    --    0.00  57.00 150.00   33
 24  ω    -60.00  -8.00   1.00    1.00    --    0.00 -19.00 -30.00   52
 25  ω    -15.00  76.00   1.00    1.00    --   54.00 -37.00-150.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1445368000
_diffrn_orient_matrix_UB_12      -0.0790259000
_diffrn_orient_matrix_UB_13      0.0041194000
_diffrn_orient_matrix_UB_21      -0.0116572000
_diffrn_orient_matrix_UB_22      -0.0649675000
_diffrn_orient_matrix_UB_23      -0.0948634000
_diffrn_orient_matrix_UB_31      0.0820842000
_diffrn_orient_matrix_UB_32      0.1167140000
_diffrn_orient_matrix_UB_33      -0.0902198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3498
_reflns_number_total             4339
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0567P)²+0.4796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1374
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C23(H23), C13(H13), C19(H19), C30(H30), C31(H31), C1(H1A), C25(H25),
 C4(H4), C9(H9), C10(H10), C28(H28), C2(H2), C26(H26), C27(H27), C3(H3)
2.b Tetrahedral OH refined with riding coordinates:
 O1(H1)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28858(17) 0.05564(13) 0.15391(11) 0.0536(4) Uani 1 1 d . . .
H1 H 0.3223 0.0660 0.0851 0.080 Uiso 1 1 calc R . .
O2 O 0.36527(19) 0.09244(13) -0.05510(11) 0.0594(4) Uani 1 1 d . . .
C7 C 0.2544(2) 0.09929(18) 0.37588(14) 0.0389(4) Uani 1 1 d . . .
H7 H 0.3449 0.0598 0.3494 0.047 Uiso 1 1 calc R . .
C23 C 0.2834(2) 0.33654(18) -0.27813(15) 0.0402(4) Uani 1 1 d . . .
H23 H 0.1977 0.3699 -0.2361 0.048 Uiso 1 1 calc R . .
C20 C 0.29293(18) 0.31313(17) -0.02981(13) 0.0355(4) Uani 1 1 d . . .
C13 C 0.21606(18) 0.41957(17) 0.11800(14) 0.0358(4) Uani 1 1 d . . .
H13 H 0.1820 0.4359 0.1905 0.043 Uiso 1 1 calc R . .
C6 C 0.1983(2) 0.09051(17) 0.49395(14) 0.0385(4) Uani 1 1 d . . .
C19 C 0.29205(19) 0.45345(18) -0.07190(14) 0.0367(4) Uani 1 1 d . . .
H19 H 0.3178 0.4965 -0.1486 0.044 Uiso 1 1 calc R . .
C8 C 0.1775(2) 0.16524(17) 0.29985(14) 0.0370(4) Uani 1 1 d . . .
C5 C 0.0587(2) 0.14662(18) 0.53346(15) 0.0406(4) Uani 1 1 d . . .
C30 C 0.5418(2) 0.2389(2) -0.40190(16) 0.0443(4) Uani 1 1 d . . .
H30 H 0.6296 0.2073 -0.4426 0.053 Uiso 1 1 calc R . .
C29 C 0.4471(2) 0.31993(19) -0.46118(15) 0.0410(4) Uani 1 1 d . . .
C12 C 0.24345(18) 0.29050(17) 0.09432(13) 0.0347(4) Uani 1 1 d . . .
C14 C 0.24722(18) 0.51943(17) 0.01731(14) 0.0346(4) Uani 1 1 d . . .
C22 C 0.3771(2) 0.25732(18) -0.22275(14) 0.0385(4) Uani 1 1 d . . .
C24 C 0.3145(2) 0.36886(18) -0.39865(15) 0.0402(4) Uani 1 1 d . . .
C31 C 0.5074(2) 0.20598(19) -0.28600(15) 0.0433(4) Uani 1 1 d . . .
H31 H 0.5698 0.1496 -0.2485 0.052 Uiso 1 1 calc R . .
C11 C 0.23871(19) 0.16962(18) 0.17694(14) 0.0377(4) Uani 1 1 d . . .
C1 C 0.2766(2) 0.0253(2) 0.57392(16) 0.0482(5) Uani 1 1 d . . .
H1A H 0.3687 -0.0121 0.5489 0.058 Uiso 1 1 calc R . .
C25 C 0.2177(2) 0.4469(2) -0.45749(17) 0.0509(5) Uani 1 1 d . . .
H25 H 0.1300 0.4788 -0.4170 0.061 Uiso 1 1 calc R . .
C4 C 0.0005(3) 0.1341(2) 0.65238(16) 0.0531(5) Uani 1 1 d . . .
H4 H -0.0920 0.1695 0.6796 0.064 Uiso 1 1 calc R . .
C9 C 0.0393(2) 0.22323(19) 0.34015(15) 0.0429(4) Uani 1 1 d . . .
H9 H -0.0128 0.2687 0.2889 0.051 Uiso 1 1 calc R . .
C10 C -0.0184(2) 0.21305(19) 0.45388(16) 0.0443(4) Uani 1 1 d . . .
H10 H -0.1103 0.2507 0.4792 0.053 Uiso 1 1 calc R . .
C15 C 0.2386(2) 0.67084(18) 0.00502(15) 0.0398(4) Uani 1 1 d . . .
C21 C 0.3423(2) 0.21707(18) -0.09657(15) 0.0406(4) Uani 1 1 d . . .
C28 C 0.4782(2) 0.3528(2) -0.58172(16) 0.0523(5) Uani 1 1 d . . .
H28 H 0.5650 0.3217 -0.6241 0.063 Uiso 1 1 calc R . .
C2 C 0.2182(3) 0.0169(2) 0.68715(17) 0.0583(6) Uani 1 1 d . . .
H2 H 0.2713 -0.0248 0.7387 0.070 Uiso 1 1 calc R . .
C26 C 0.2518(3) 0.4761(2) -0.57368(18) 0.0605(6) Uani 1 1 d . . .
H26 H 0.1870 0.5278 -0.6115 0.073 Uiso 1 1 calc R . .
C27 C 0.3828(3) 0.4291(2) -0.63592(17) 0.0593(6) Uani 1 1 d . . .
H27 H 0.4050 0.4500 -0.7149 0.071 Uiso 1 1 calc R . .
C3 C 0.0788(3) 0.0707(2) 0.72639(17) 0.0599(6) Uani 1 1 d . . .
H3 H 0.0394 0.0630 0.8040 0.072 Uiso 1 1 calc R . .
C18 C 0.3706(3) 0.7345(2) -0.0840(2) 0.0671(6) Uani 1 1 d . . .
H18A H 0.4569 0.6914 -0.0650 0.101 Uiso 1 1 calc R . .
H18B H 0.3685 0.8287 -0.0859 0.101 Uiso 1 1 calc R . .
H18C H 0.3696 0.7233 -0.1573 0.101 Uiso 1 1 calc R . .
C17 C 0.1030(3) 0.7304(3) -0.0317(3) 0.0864(9) Uani 1 1 d . . .
H17A H 0.1060 0.7098 -0.1026 0.130 Uiso 1 1 calc R . .
H17B H 0.0984 0.8264 -0.0409 0.130 Uiso 1 1 calc R . .
H17C H 0.0192 0.6927 0.0251 0.130 Uiso 1 1 calc R . .
C16 C 0.2355(4) 0.7045(2) 0.1167(2) 0.0943(11) Uani 1 1 d . . .
H16A H 0.1511 0.6687 0.1739 0.141 Uiso 1 1 calc R . .
H16B H 0.2331 0.8006 0.1067 0.141 Uiso 1 1 calc R . .
H16C H 0.3206 0.6656 0.1401 0.141 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 H1 0.8200 . ?
O1 C11 1.286(2) . ?
O2 C21 1.275(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.416(2) . ?
C7 C8 1.373(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.367(2) . ?
C23 C24 1.420(2) . ?
C20 C19 1.404(2) . ?
C20 C12 1.466(2) . ?
C20 C21 1.412(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.411(2) . ?
C13 C14 1.396(2) . ?
C6 C5 1.411(3) . ?
C6 C1 1.417(2) . ?
C19 H19 0.9300 . ?
C19 C14 1.398(2) . ?
C8 C11 1.485(2) . ?
C8 C9 1.409(3) . ?
C5 C4 1.422(3) . ?
C5 C10 1.408(3) . ?
C30 H30 0.9300 . ?
C30 C29 1.409(3) . ?
C30 C31 1.364(2) . ?
C29 C24 1.415(3) . ?
C29 C28 1.420(2) . ?
C12 C11 1.400(2) . ?
C14 C15 1.518(2) . ?
C22 C31 1.413(3) . ?
C22 C21 1.487(2) . ?
C24 C25 1.409(3) . ?
C31 H31 0.9300 . ?
C1 H1A 0.9300 . ?
C1 C2 1.363(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.357(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.365(3) . ?
C10 H10 0.9300 . ?
C15 C18 1.523(3) . ?
C15 C17 1.522(3) . ?
C15 C16 1.522(3) . ?
C28 H28 0.9300 . ?
C28 C27 1.360(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.395(3) . ?
C27 H27 0.9300 . ?
C3 H3 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C11 O1 H1 109.5 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C8 C7 C6 121.08(17) . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.25(17) . . ?
C24 C23 H23 119.4 . . ?
C19 C20 C12 106.10(15) . . ?
C19 C20 C21 125.22(16) . . ?
C21 C20 C12 128.54(16) . . ?
C12 C13 H13 124.8 . . ?
C14 C13 H13 124.8 . . ?
C14 C13 C12 110.44(15) . . ?
C7 C6 C1 122.20(18) . . ?
C5 C6 C7 118.89(16) . . ?
C5 C6 C1 118.90(17) . . ?
C20 C19 H19 124.7 . . ?
C14 C19 C20 110.65(15) . . ?
C14 C19 H19 124.7 . . ?
C7 C8 C11 119.44(16) . . ?
C7 C8 C9 119.47(16) . . ?
C9 C8 C11 121.05(15) . . ?
C6 C5 C4 118.88(18) . . ?
C10 C5 C6 118.92(16) . . ?
C10 C5 C4 122.21(18) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C31 C30 C29 121.31(18) . . ?
C30 C29 C24 119.00(16) . . ?
C30 C29 C28 122.57(18) . . ?
C24 C29 C28 118.42(18) . . ?
C13 C12 C20 105.96(14) . . ?
C11 C12 C20 129.13(16) . . ?
C11 C12 C13 124.52(15) . . ?
C13 C14 C19 106.83(15) . . ?
C13 C14 C15 127.42(15) . . ?
C19 C14 C15 125.74(15) . . ?
C23 C22 C31 119.72(16) . . ?
C23 C22 C21 121.68(16) . . ?
C31 C22 C21 118.51(16) . . ?
C29 C24 C23 118.51(16) . . ?
C25 C24 C23 122.30(18) . . ?
C25 C24 C29 119.19(17) . . ?
C30 C31 C22 120.15(17) . . ?
C30 C31 H31 119.9 . . ?
C22 C31 H31 119.9 . . ?
O1 C11 C8 114.84(15) . . ?
O1 C11 C12 123.61(16) . . ?
C12 C11 C8 121.53(16) . . ?
C6 C1 H1A 119.7 . . ?
C2 C1 C6 120.6(2) . . ?
C2 C1 H1A 119.7 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.7 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.43(17) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.18(18) . . ?
C9 C10 H10 119.4 . . ?
C14 C15 C18 110.27(16) . . ?
C14 C15 C17 109.39(17) . . ?
C14 C15 C16 110.72(15) . . ?
C17 C15 C18 109.01(19) . . ?
C17 C15 C16 109.8(2) . . ?
C16 C15 C18 107.6(2) . . ?
O2 C21 C20 123.55(16) . . ?
O2 C21 C22 115.16(16) . . ?
C20 C21 C22 121.24(16) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 C29 120.9(2) . . ?
C27 C28 H28 119.5 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.6(2) . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 120.36(19) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C4 C3 C2 120.66(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.65 2.4675(18) 171.5 .

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
C7 C6 C5 C4 178.04(17) . . . . ?
C7 C6 C5 C10 -1.9(3) . . . . ?
C7 C6 C1 C2 -178.96(19) . . . . ?
C7 C8 C11 O1 47.5(2) . . . . ?
C7 C8 C11 C12 -131.10(19) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C23 C22 C31 C30 2.2(3) . . . . ?
C23 C22 C21 O2 132.9(2) . . . . ?
C23 C22 C21 C20 -49.5(3) . . . . ?
C23 C24 C25 C26 179.85(19) . . . . ?
C20 C19 C14 C13 -1.2(2) . . . . ?
C20 C19 C14 C15 177.38(16) . . . . ?
C20 C12 C11 O1 4.7(3) . . . . ?
C20 C12 C11 C8 -176.78(17) . . . . ?
C13 C12 C11 O1 -167.01(17) . . . . ?
C13 C12 C11 C8 11.5(3) . . . . ?
C13 C14 C15 C18 136.5(2) . . . . ?
C13 C14 C15 C17 -103.7(2) . . . . ?
C13 C14 C15 C16 17.5(3) . . . . ?
C6 C7 C8 C11 -178.66(16) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C6 C5 C4 C3 0.9(3) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C19 C20 C12 C13 0.08(18) . . . . ?
C19 C20 C12 C11 -172.82(18) . . . . ?
C19 C20 C21 O2 167.35(19) . . . . ?
C19 C20 C21 C22 -10.0(3) . . . . ?
C19 C14 C15 C18 -41.9(2) . . . . ?
C19 C14 C15 C17 78.0(2) . . . . ?
C19 C14 C15 C16 -160.9(2) . . . . ?
C8 C7 C6 C5 2.3(3) . . . . ?
C8 C7 C6 C1 -178.78(17) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C30 C29 C24 C23 1.3(3) . . . . ?
C30 C29 C24 C25 -178.31(17) . . . . ?
C30 C29 C28 C27 178.65(19) . . . . ?
C29 C30 C31 C22 -2.4(3) . . . . ?
C29 C24 C25 C26 -0.5(3) . . . . ?
C29 C28 C27 C26 -0.3(3) . . . . ?
C12 C20 C19 C14 0.70(19) . . . . ?
C12 C20 C21 O2 -7.8(3) . . . . ?
C12 C20 C21 C22 174.89(17) . . . . ?
C12 C13 C14 C19 1.28(19) . . . . ?
C12 C13 C14 C15 -177.30(16) . . . . ?
C14 C13 C12 C20 -0.84(19) . . . . ?
C14 C13 C12 C11 172.48(16) . . . . ?
C22 C23 C24 C29 -1.6(3) . . . . ?
C22 C23 C24 C25 178.04(18) . . . . ?
C24 C23 C22 C31 -0.1(3) . . . . ?
C24 C23 C22 C21 -176.79(17) . . . . ?
C24 C29 C28 C27 -0.2(3) . . . . ?
C24 C25 C26 C27 0.0(3) . . . . ?
C31 C30 C29 C24 0.7(3) . . . . ?
C31 C30 C29 C28 -178.21(19) . . . . ?
C31 C22 C21 O2 -43.8(3) . . . . ?
C31 C22 C21 C20 133.78(19) . . . . ?
C11 C8 C9 C10 176.96(18) . . . . ?
C1 C6 C5 C4 -0.9(3) . . . . ?
C1 C6 C5 C10 179.13(17) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
C4 C5 C10 C9 -179.64(19) . . . . ?
C9 C8 C11 O1 -130.04(19) . . . . ?
C9 C8 C11 C12 51.3(3) . . . . ?
C10 C5 C4 C3 -179.17(19) . . . . ?
C21 C20 C19 C14 -175.31(16) . . . . ?
C21 C20 C12 C13 175.92(17) . . . . ?
C21 C20 C12 C11 3.0(3) . . . . ?
C21 C22 C31 C30 178.91(17) . . . . ?
C28 C29 C24 C23 -179.76(17) . . . . ?
C28 C29 C24 C25 0.6(3) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.537
_oxdiff_exptl_absorpt_empirical_full_min 0.620

####################################################################### 
# 
# 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_3249
_database_code_depnum_ccdc_archive 'CCDC 1914743'
loop_
_audit_author_name
_audit_author_address
'Yan Geng'
;Shandong Normal University
China
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C31 H25 B F2 O2'
_chemical_formula_sum            'C31 H25 B F2 O2'
_chemical_formula_weight         478.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1'
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.5441(19)
_cell_length_b                   12.1699(4)
_cell_length_c                   20.6663(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.726(11)
_cell_angle_gamma                90.00
_cell_volume                     5134.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5105
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6670
_cell_measurement_theta_min      5.6590
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16290
_diffrn_reflns_theta_full        67.07
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.23
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9873
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00 126.00   1.00    1.50    --   54.00  37.00  90.00   98
  2  ω    117.00 142.00   1.00    1.50    --  108.00 -25.00 150.00   25
  3  ω    100.00 127.00   1.00    1.50    --  108.00 -50.00 120.00   27
  4  ω     81.00 107.00   1.00    1.50    --  108.00 -25.00 150.00   26
  5  ω     77.00 141.00   1.00    1.50    --  108.00 -91.00 150.00   64
  6  ω     94.00 120.00   1.00    1.50    --  108.00-123.00 118.00   26
  7  ω     70.00 108.00   1.00    1.50    --  108.00-111.00   0.00   38
  8  ω     91.00 116.00   1.00    1.50    --  108.00-111.00-120.00   25
  9  ω     63.00  89.00   1.00    1.50    --  108.00-111.00-180.00   26
 10  ω     44.00  70.00   1.00    1.50    --  108.00-111.00-120.00   26
 11  ω     38.00 127.00   1.00    1.50    --  108.00 -50.00-120.00   89
 12  ω     91.00 177.00   1.00    1.50    --  108.00  50.00 -30.00   86
 13  ω    153.00 178.00   1.00    1.50    --  108.00 111.00  60.00   25
 14  ω    100.00 178.00   1.00    1.50    --  108.00 111.00 -90.00   78
 15  ω    100.00 126.00   1.00    1.50    --  108.00 111.00  60.00   26
 16  ω     74.00 122.00   1.00    1.50    --   54.00  57.00 -30.00   48
 17  ω     74.00 177.00   1.00    1.50    --  108.00  25.00  60.00  103
 18  ω     42.00 111.00   1.00    1.50    --   54.00-125.00-180.00   69
 19  ω     40.00 130.00   1.00    1.50    --  108.00 -77.00   0.00   90
 20  ω     45.00  81.00   1.00    1.50    --  108.00 -50.00 120.00   36
 21  ω     41.00  71.00   1.00    1.50    --  108.00 -25.00 150.00   30
 22  ω     26.00  64.00   1.00    1.50    --   54.00-125.00  30.00   38
 23  ω     40.00  67.00   1.00    1.50    --   54.00-123.00 118.00   27
 24  ω     38.00 118.00   1.00    1.50    --  108.00 -37.00   0.00   80
 25  ω     31.00  59.00   1.00    1.50    --    0.00  57.00-150.00   28
 26  ω    -21.00  27.00   1.00    1.50    --    0.00  57.00-150.00   48
 27  ω    -32.00  10.00   1.00    1.50    --    0.00 -57.00   0.00   42
 28  ω    -36.00  -9.00   1.00    1.50    --    0.00 -57.00  90.00   27
 29  ω    -12.00  74.00   1.00    1.50    --   54.00 -37.00 150.00   86
 30  ω    -15.00  24.00   1.00    1.50    --   54.00 -57.00 120.00   39
 31  ω    -16.00  42.00   1.00    1.50    --   54.00 -77.00 -60.00   58
 32  ω    -69.00 -40.00   1.00    1.50    --    0.00 -57.00  90.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0211557000
_diffrn_orient_matrix_UB_12      -0.0568033000
_diffrn_orient_matrix_UB_13      -0.0493111000
_diffrn_orient_matrix_UB_21      0.0721450000
_diffrn_orient_matrix_UB_22      0.0266819000
_diffrn_orient_matrix_UB_23      0.0628360000
_diffrn_orient_matrix_UB_31      0.0065993000
_diffrn_orient_matrix_UB_32      -0.1099498000
_diffrn_orient_matrix_UB_33      0.0407198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3406
_reflns_number_total             4594
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.00044(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4594
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0745
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1386P)²+4.2806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2210
_refine_ls_wR_factor_ref         0.2422
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C16' \\sim C17' \\sim C18': within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.005
3. Others
 Sof(C16')=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17')=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=Sof(C18')=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
4.a Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16'(H16D,H16E,
 H16F), C17'(H17D,H17E,H17F), C18'(H18D,H18E,H18F)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C19(H19),
 C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.3006(3) 0.4842(3) 0.3914(4) 0.0980(18) Uani 1 1 d . . .
C1 C 0.39744(15) 0.5429(3) 0.24196(19) 0.0661(8) Uani 1 1 d . . .
H1 H 0.4001 0.4685 0.2338 0.079 Uiso 1 1 calc R . .
C2 C 0.40866(15) 0.6232(3) 0.19936(18) 0.0686(8) Uani 1 1 d . . .
C3 C 0.42219(18) 0.5917(4) 0.1452(2) 0.0840(10) Uani 1 1 d . . .
H3 H 0.4240 0.5175 0.1358 0.101 Uiso 1 1 calc R . .
C4 C 0.4329(2) 0.6685(5) 0.1055(3) 0.1008(14) Uani 1 1 d . . .
H4 H 0.4419 0.6470 0.0692 0.121 Uiso 1 1 calc R . .
C5 C 0.4303(2) 0.7822(5) 0.1202(3) 0.1135(17) Uani 1 1 d . . .
H5 H 0.4384 0.8346 0.0938 0.136 Uiso 1 1 calc R . .
C6 C 0.4165(2) 0.8145(4) 0.1707(3) 0.1079(15) Uani 1 1 d . . .
H6 H 0.4144 0.8891 0.1787 0.129 Uiso 1 1 calc R . .
C7 C 0.40471(18) 0.7342(3) 0.2137(2) 0.0780(9) Uani 1 1 d . . .
C8 C 0.3901(2) 0.7655(3) 0.2668(3) 0.0907(12) Uani 1 1 d . . .
H8 H 0.3884 0.8397 0.2763 0.109 Uiso 1 1 calc R . .
C9 C 0.37831(19) 0.6886(3) 0.3050(2) 0.0798(10) Uani 1 1 d . . .
H9 H 0.3669 0.7107 0.3390 0.096 Uiso 1 1 calc R . .
C10 C 0.38309(15) 0.5744(3) 0.29385(19) 0.0632(8) Uani 1 1 d . . .
C11 C 0.36687(16) 0.4944(2) 0.33415(18) 0.0602(7) Uani 1 1 d . . .
C12 C 0.39887(14) 0.3936(2) 0.36313(17) 0.0574(7) Uani 1 1 d . . .
C13 C 0.45761(15) 0.3616(2) 0.37182(18) 0.0618(7) Uani 1 1 d . . .
H13 H 0.4825 0.4064 0.3613 0.074 Uiso 1 1 calc R . .
C14 C 0.47343(14) 0.2537(3) 0.39830(19) 0.0626(7) Uani 1 1 d . A .
C15 C 0.5326(2) 0.1890(4) 0.4162(3) 0.0954(11) Uani 1 1 d U . .
C16 C 0.5733(4) 0.2529(7) 0.3918(6) 0.1075(18) Uani 0.577(5) 1 d PU A 1
H16A H 0.6094 0.2084 0.4016 0.161 Uiso 0.577(5) 1 calc PR A 1
H16B H 0.5896 0.3197 0.4213 0.161 Uiso 0.577(5) 1 calc PR A 1
H16C H 0.5460 0.2702 0.3373 0.161 Uiso 0.577(5) 1 calc PR A 1
C17 C 0.5056(4) 0.0888(7) 0.3587(6) 0.111(2) Uani 0.577(5) 1 d PU A 1
H17A H 0.4766 0.1149 0.3064 0.167 Uiso 0.577(5) 1 calc PR A 1
H17B H 0.4823 0.0402 0.3717 0.167 Uiso 0.577(5) 1 calc PR A 1
H17C H 0.5415 0.0501 0.3628 0.167 Uiso 0.577(5) 1 calc PR A 1
C18 C 0.5667(5) 0.1443(9) 0.4935(7) 0.134(3) Uani 0.577(5) 1 d PU A 1
H18A H 0.5368 0.1021 0.4997 0.202 Uiso 0.577(5) 1 calc PR A 1
H18B H 0.5844 0.2032 0.5307 0.202 Uiso 0.577(5) 1 calc PR A 1
H18C H 0.6017 0.0978 0.5018 0.202 Uiso 0.577(5) 1 calc PR A 1
C19 C 0.42380(14) 0.2152(2) 0.40578(18) 0.0585(7) Uani 1 1 d . . .
H19 H 0.4219 0.1447 0.4218 0.070 Uiso 1 1 calc R A .
C20 C 0.37681(15) 0.2978(2) 0.38571(17) 0.0551(7) Uani 1 1 d . A .
C21 C 0.32099(15) 0.2856(2) 0.38635(18) 0.0575(7) Uani 1 1 d . . .
C22 C 0.29880(14) 0.1779(2) 0.39648(17) 0.0536(7) Uani 1 1 d . A .
C23 C 0.29631(13) 0.0864(2) 0.35720(17) 0.0543(7) Uani 1 1 d . . .
H23 H 0.3101 0.0905 0.3234 0.065 Uiso 1 1 calc R A .
C24 C 0.27320(13) -0.0150(2) 0.36665(16) 0.0514(6) Uani 1 1 d . A .
C25 C 0.26801(16) -0.1103(2) 0.32497(19) 0.0648(8) Uani 1 1 d . . .
H25 H 0.2811 -0.1082 0.2905 0.078 Uiso 1 1 calc R A .
C26 C 0.24408(18) -0.2054(3) 0.3345(2) 0.0748(9) Uani 1 1 d . A .
H26 H 0.2408 -0.2676 0.3064 0.090 Uiso 1 1 calc R . .
C27 C 0.22425(17) -0.2103(3) 0.3865(2) 0.0735(9) Uani 1 1 d . . .
H27 H 0.2079 -0.2757 0.3926 0.088 Uiso 1 1 calc R A .
C28 C 0.22878(15) -0.1207(2) 0.4276(2) 0.0661(8) Uani 1 1 d . A .
H28 H 0.2157 -0.1251 0.4620 0.079 Uiso 1 1 calc R . .
C29 C 0.25325(13) -0.0194(2) 0.41915(17) 0.0532(7) Uani 1 1 d . . .
C30 C 0.25721(15) 0.0757(2) 0.45993(19) 0.0628(8) Uani 1 1 d . A .
H30 H 0.2453 0.0726 0.4954 0.075 Uiso 1 1 calc R . .
C31 C 0.27826(16) 0.1722(2) 0.4482(2) 0.0630(8) Uani 1 1 d . . .
H31 H 0.2792 0.2351 0.4743 0.076 Uiso 1 1 calc R A .
C16' C 0.5427(6) 0.0791(10) 0.4575(9) 0.117(3) Uani 0.423(5) 1 d PU A 2
H16D H 0.5063 0.0314 0.4244 0.175 Uiso 0.423(5) 1 calc PR A 2
H16E H 0.5455 0.0913 0.5051 0.175 Uiso 0.423(5) 1 calc PR A 2
H16F H 0.5824 0.0456 0.4687 0.175 Uiso 0.423(5) 1 calc PR A 2
C17' C 0.5956(5) 0.2579(10) 0.4691(9) 0.115(2) Uani 0.423(5) 1 d PU A 2
H17D H 0.6323 0.2215 0.4736 0.173 Uiso 0.423(5) 1 calc PR A 2
H17E H 0.6032 0.2655 0.5197 0.173 Uiso 0.423(5) 1 calc PR A 2
H17F H 0.5902 0.3293 0.4465 0.173 Uiso 0.423(5) 1 calc PR A 2
C18' C 0.5319(6) 0.1696(11) 0.3441(9) 0.120(2) Uani 0.423(5) 1 d PU A 2
H18D H 0.5003 0.1138 0.3131 0.180 Uiso 0.423(5) 1 calc PR A 2
H18E H 0.5745 0.1461 0.3583 0.180 Uiso 0.423(5) 1 calc PR A 2
H18F H 0.5204 0.2365 0.3147 0.180 Uiso 0.423(5) 1 calc PR A 2
F1 F 0.2464(2) 0.53839(19) 0.3742(3) 0.1645(18) Uani 1 1 d . . .
F2 F 0.3514(2) 0.4991(2) 0.4661(2) 0.1488(15) Uani 1 1 d . . .
O1 O 0.31876(12) 0.52745(17) 0.33879(15) 0.0729(7) Uani 1 1 d . . .
O2 O 0.28360(13) 0.36654(16) 0.37958(17) 0.0802(8) Uani 1 1 d . A .


_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
B1 F1 1.345(6) . ?
B1 F2 1.355(8) . ?
B1 O1 1.481(5) . ?
B1 O2 1.473(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.440(4) . ?
C1 C10 1.357(5) . ?
C2 C3 1.387(5) . ?
C2 C7 1.398(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.426(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.321(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.455(5) . ?
C7 C8 1.384(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.355(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.424(5) . ?
C10 C11 1.472(4) . ?
C11 C12 1.400(4) . ?
C11 O1 1.300(4) . ?
C12 C13 1.405(4) . ?
C12 C20 1.466(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 C15 1.507(5) . ?
C14 C19 1.392(4) . ?
C15 C16 1.555(8) . ?
C15 C17 1.569(10) . ?
C15 C18 1.436(12) . ?
C15 C16' 1.531(13) . ?
C15 C17' 1.553(12) . ?
C15 C18' 1.499(15) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C20 1.408(4) . ?
C20 C21 1.385(4) . ?
C21 C22 1.478(4) . ?
C21 O2 1.300(3) . ?
C22 C23 1.360(4) . ?
C22 C31 1.413(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.416(4) . ?
C24 C25 1.408(4) . ?
C24 C29 1.418(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.361(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.406(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.348(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.424(4) . ?
C29 C30 1.403(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.358(4) . ?
C31 H31 0.9300 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 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
F1 B1 F2 112.6(4) . . ?
F1 B1 O1 106.8(4) . . ?
F1 B1 O2 106.5(4) . . ?
F2 B1 O1 109.2(4) . . ?
F2 B1 O2 108.4(4) . . ?
O2 B1 O1 113.4(3) . . ?
C2 C1 H1 119.6 . . ?
C10 C1 H1 119.6 . . ?
C10 C1 C2 120.9(3) . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 C7 120.9(3) . . ?
C7 C2 C1 117.8(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(5) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 117.3(4) . . ?
C8 C7 C2 120.9(3) . . ?
C8 C7 C6 121.8(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.1(4) . . ?
C10 C9 H9 119.4 . . ?
C1 C10 C9 118.9(3) . . ?
C1 C10 C11 122.1(3) . . ?
C9 C10 C11 118.8(3) . . ?
C12 C11 C10 123.9(3) . . ?
O1 C11 C10 112.3(3) . . ?
O1 C11 C12 123.8(3) . . ?
C11 C12 C13 126.1(3) . . ?
C11 C12 C20 127.9(3) . . ?
C13 C12 C20 105.9(2) . . ?
C12 C13 H13 124.6 . . ?
C14 C13 C12 110.7(3) . . ?
C14 C13 H13 124.6 . . ?
C13 C14 C15 127.6(3) . . ?
C19 C14 C13 106.9(3) . . ?
C19 C14 C15 125.4(3) . . ?
C14 C15 C16 111.3(4) . . ?
C14 C15 C17 106.0(4) . . ?
C14 C15 C16' 115.4(5) . . ?
C14 C15 C17' 109.7(5) . . ?
C16 C15 C17 102.7(6) . . ?
C18 C15 C14 111.0(6) . . ?
C18 C15 C16 117.9(7) . . ?
C18 C15 C17 106.8(7) . . ?
C18 C15 C16' 40.2(6) . . ?
C18 C15 C17' 71.6(7) . . ?
C18 C15 C18' 136.4(7) . . ?
C16' C15 C16 133.2(6) . . ?
C16' C15 C17 67.2(7) . . ?
C16' C15 C17' 106.9(8) . . ?
C17' C15 C16 52.4(6) . . ?
C17' C15 C17 142.1(6) . . ?
C18' C15 C14 111.1(6) . . ?
C18' C15 C16 53.9(6) . . ?
C18' C15 C17 50.0(6) . . ?
C18' C15 C16' 109.0(8) . . ?
C18' C15 C17' 104.0(8) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19 124.7 . . ?
C14 C19 C20 110.5(3) . . ?
C20 C19 H19 124.7 . . ?
C19 C20 C12 105.9(2) . . ?
C21 C20 C12 129.0(3) . . ?
C21 C20 C19 125.0(2) . . ?
C20 C21 C22 122.7(2) . . ?
O2 C21 C20 124.1(2) . . ?
O2 C21 C22 113.2(2) . . ?
C23 C22 C21 122.7(2) . . ?
C23 C22 C31 119.6(2) . . ?
C31 C22 C21 117.7(2) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.3(3) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C29 118.3(2) . . ?
C25 C24 C23 122.7(3) . . ?
C25 C24 C29 119.0(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.5 . . ?
C27 C28 C29 121.1(3) . . ?
C29 C28 H28 119.5 . . ?
C24 C29 C28 118.4(3) . . ?
C30 C29 C24 119.3(2) . . ?
C30 C29 C28 122.3(3) . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.8(3) . . ?
C31 C30 H30 119.6 . . ?
C22 C31 H31 119.7 . . ?
C30 C31 C22 120.6(3) . . ?
C30 C31 H31 119.7 . . ?
C15 C16' H16D 109.5 . . ?
C15 C16' H16E 109.5 . . ?
C15 C16' H16F 109.5 . . ?
H16D C16' H16E 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C15 C17' H17D 109.5 . . ?
C15 C17' H17E 109.5 . . ?
C15 C17' H17F 109.5 . . ?
H17D C17' H17E 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C15 C18' H18D 109.5 . . ?
C15 C18' H18E 109.5 . . ?
C15 C18' H18F 109.5 . . ?
H18D C18' H18E 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C11 O1 B1 126.8(3) . . ?
C21 O2 B1 126.9(3) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.640

