# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1a_270k
_database_code_depnum_ccdc_archive 'CCDC 1857573'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-anisyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C23 H22 O3'
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H22 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.7826(5)
_cell_length_b                   9.2243(2)
_cell_length_c                   15.0346(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.733(4)
_cell_angle_gamma                90
_cell_volume                     1775.55(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4221
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      31.5380
_cell_measurement_theta_min      2.7840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.39
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16837
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.646
_diffrn_ambient_temperature      270.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -57.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
  3 omega   45.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -178.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega   44.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega   11.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   57.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  7 omega  -44.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -19.0000    0.0000 110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0515860000
_diffrn_orient_matrix_UB_12      -0.0004514000
_diffrn_orient_matrix_UB_13      0.0002879000
_diffrn_orient_matrix_UB_21      -0.0135488000
_diffrn_orient_matrix_UB_22      0.0561707000
_diffrn_orient_matrix_UB_23      -0.0346752000
_diffrn_orient_matrix_UB_31      0.0149897000
_diffrn_orient_matrix_UB_32      0.0524842000
_diffrn_orient_matrix_UB_33      0.0371131000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3543
_reflns_number_total             4727
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.3220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1245
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C7(H7), C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C21(H21), C19(H19), C11(H11), C8(H8), C9(H9), C12(H12),
 C15(H15), C6(H6), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63623(7) 0.85577(10) 0.44154(6) 0.0342(2) Uani 1 1 d . . . . .
H1 H 0.635030 0.941160 0.426004 0.051 Uiso 1 1 calc GR . . . .
O3 O 0.66618(9) 0.17920(11) 0.49418(7) 0.0447(3) Uani 1 1 d . . . . .
C20 C 0.66696(10) 0.32355(14) 0.47170(9) 0.0320(3) Uani 1 1 d . . . . .
C1 C 0.67109(9) 0.76840(13) 0.38030(8) 0.0277(3) Uani 1 1 d . . . . .
C10 C 0.86440(9) 0.81878(14) 0.48131(9) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.77728(10) 0.82573(14) 0.38490(9) 0.0296(3) Uani 1 1 d . . . . .
C17 C 0.67467(9) 0.61262(13) 0.41501(8) 0.0274(3) Uani 1 1 d . . . . .
C18 C 0.63150(10) 0.57639(14) 0.48193(9) 0.0316(3) Uani 1 1 d . . . . .
H18 H 0.604676 0.649594 0.508699 0.038 Uiso 1 1 calc R . . . .
C22 C 0.71730(10) 0.50011(14) 0.37931(9) 0.0337(3) Uani 1 1 d . . . . .
H22 H 0.748889 0.521182 0.335857 0.040 Uiso 1 1 calc R . . . .
C7 C 0.59067(11) 0.78418(14) 0.27590(9) 0.0348(3) Uani 1 1 d . . . . .
H7 H 0.522832 0.743981 0.270296 0.042 Uiso 1 1 calc R . . . .
C21 C 0.71369(11) 0.35809(14) 0.40700(9) 0.0348(3) Uani 1 1 d . . . . .
H21 H 0.742763 0.285096 0.382117 0.042 Uiso 1 1 calc R . . . .
C19 C 0.62711(11) 0.43367(14) 0.51022(9) 0.0340(3) Uani 1 1 d . . . . .
H19 H 0.597362 0.412529 0.555042 0.041 Uiso 1 1 calc R . . . .
C11 C 0.87525(11) 0.92557(16) 0.54909(10) 0.0378(3) Uani 1 1 d . . . . .
H11 H 0.831222 1.005711 0.532336 0.045 Uiso 1 1 calc R . . . .
C3 C 0.76885(11) 0.96077(15) 0.32560(10) 0.0377(3) Uani 1 1 d . . . . .
H3 H 0.825698 1.031082 0.351546 0.045 Uiso 1 1 calc R . . . .
C8 C 0.58004(12) 0.94161(16) 0.24730(10) 0.0411(3) Uani 1 1 d . . . . .
H8 H 0.514734 0.982036 0.214267 0.049 Uiso 1 1 calc R . . . .
C9 C 0.66632(12) 1.02154(15) 0.27042(9) 0.0409(3) Uani 1 1 d . . . . .
H9 H 0.661176 1.117915 0.251051 0.049 Uiso 1 1 calc R . . . .
C12 C 0.94997(11) 0.91674(17) 0.64148(10) 0.0430(3) Uani 1 1 d . . . . .
H12 H 0.955046 0.989134 0.686037 0.052 Uiso 1 1 calc R . . . .
C15 C 0.93456(11) 0.70372(16) 0.50756(11) 0.0427(3) Uani 1 1 d . . . . .
H15 H 0.930607 0.631794 0.462995 0.051 Uiso 1 1 calc R . . . .
C6 C 0.62774(13) 0.71676(16) 0.20305(10) 0.0443(4) Uani 1 1 d . . . . .
H6 H 0.581960 0.663301 0.152426 0.053 Uiso 1 1 calc R . . . .
O2 O 1.09177(9) 0.77619(15) 0.75531(8) 0.0656(4) Uani 1 1 d . . . . .
C13 C 1.01638(11) 0.79904(17) 0.66599(10) 0.0431(4) Uani 1 1 d . . . . .
C4 C 0.80064(12) 0.80822(16) 0.29519(10) 0.0402(3) Uani 1 1 d . . . . .
H4 H 0.874521 0.796754 0.304738 0.048 Uiso 1 1 calc R . . . .
C5 C 0.72627(14) 0.73425(17) 0.21170(10) 0.0463(4) Uani 1 1 d . . . . .
H5 H 0.748298 0.699209 0.164295 0.056 Uiso 1 1 calc R . . . .
C14 C 1.00985(12) 0.69434(18) 0.59841(12) 0.0498(4) Uani 1 1 d . . . . .
H14 H 1.056496 0.617055 0.614261 0.060 Uiso 1 1 calc R . . . .
C23 C 0.63555(16) 0.14302(18) 0.57200(12) 0.0585(5) Uani 1 1 d . . . . .
H23A H 0.563918 0.170106 0.556659 0.088 Uiso 1 1 calc GR . . . .
H23B H 0.678918 0.194048 0.628352 0.088 Uiso 1 1 calc GR . . . .
H23C H 0.643133 0.040511 0.583493 0.088 Uiso 1 1 calc GR . . . .
C16 C 1.09465(16) 0.8745(3) 0.82919(12) 0.0752(6) Uani 1 1 d . . . . .
H16A H 1.116119 0.968369 0.815855 0.113 Uiso 1 1 calc GR . . . .
H16B H 1.143372 0.840077 0.889435 0.113 Uiso 1 1 calc GR . . . .
H16C H 1.026400 0.881339 0.832135 0.113 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 H1 0.8200 . ?
O1 C1 1.4337(14) . ?
O3 C20 1.3748(16) . ?
O3 C23 1.4228(18) . ?
C20 C21 1.3880(19) . ?
C20 C19 1.3800(19) . ?
C1 C2 1.5335(17) . ?
C1 C17 1.5233(17) . ?
C1 C7 1.5573(17) . ?
C10 C2 1.5027(17) . ?
C10 C11 1.3850(19) . ?
C10 C15 1.3909(19) . ?
C2 C3 1.5112(18) . ?
C2 C4 1.5069(18) . ?
C17 C18 1.3860(18) . ?
C17 C22 1.3943(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3917(18) . ?
C22 H22 0.9300 . ?
C22 C21 1.3810(19) . ?
C7 H7 0.9800 . ?
C7 C8 1.5061(19) . ?
C7 C6 1.504(2) . ?
C21 H21 0.9300 . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.3919(19) . ?
C3 H3 0.9800 . ?
C3 C9 1.460(2) . ?
C3 C4 1.590(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.331(2) . ?
C9 H9 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.379(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.379(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.325(2) . ?
O2 C13 1.3762(17) . ?
O2 C16 1.423(2) . ?
C13 C14 1.380(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.463(2) . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 O1 H1 109.5 . . ?
C20 O3 C23 117.45(11) . . ?
O3 C20 C21 116.26(12) . . ?
O3 C20 C19 124.70(12) . . ?
C19 C20 C21 119.03(12) . . ?
O1 C1 C2 108.56(10) . . ?
O1 C1 C17 106.64(10) . . ?
O1 C1 C7 108.18(10) . . ?
C2 C1 C7 108.93(10) . . ?
C17 C1 C2 113.61(10) . . ?
C17 C1 C7 110.74(10) . . ?
C11 C10 C2 120.62(12) . . ?
C11 C10 C15 117.37(12) . . ?
C15 C10 C2 121.97(12) . . ?
C10 C2 C1 115.93(10) . . ?
C10 C2 C3 117.62(11) . . ?
C10 C2 C4 119.97(11) . . ?
C3 C2 C1 113.21(10) . . ?
C4 C2 C1 116.07(11) . . ?
C4 C2 C3 63.60(9) . . ?
C18 C17 C1 120.53(11) . . ?
C18 C17 C22 117.08(11) . . ?
C22 C17 C1 122.35(11) . . ?
C17 C18 H18 119.0 . . ?
C17 C18 C19 121.93(12) . . ?
C19 C18 H18 119.0 . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.51(12) . . ?
C21 C22 H22 119.2 . . ?
C1 C7 H7 110.6 . . ?
C8 C7 C1 109.61(10) . . ?
C8 C7 H7 110.6 . . ?
C6 C7 C1 112.86(11) . . ?
C6 C7 H7 110.6 . . ?
C6 C7 C8 102.37(12) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.45(12) . . ?
C22 C21 H21 119.8 . . ?
C20 C19 C18 119.93(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 122.07(13) . . ?
C12 C11 H11 119.0 . . ?
C2 C3 H3 115.8 . . ?
C2 C3 C4 58.07(8) . . ?
C9 C3 C2 119.90(12) . . ?
C9 C3 H3 115.8 . . ?
C9 C3 C4 119.22(12) . . ?
C4 C3 H3 115.8 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.45(13) . . ?
C9 C8 H8 120.8 . . ?
C3 C9 H9 119.4 . . ?
C8 C9 C3 121.25(13) . . ?
C8 C9 H9 119.4 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.03(14) . . ?
C13 C12 H12 120.5 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.20(14) . . ?
C14 C15 H15 119.4 . . ?
C7 C6 H6 120.3 . . ?
C5 C6 C7 119.36(13) . . ?
C5 C6 H6 120.3 . . ?
C13 O2 C16 117.18(14) . . ?
C12 C13 C14 119.87(13) . . ?
O2 C13 C12 124.60(14) . . ?
O2 C13 C14 115.52(14) . . ?
C2 C4 C3 58.33(8) . . ?
C2 C4 H4 115.8 . . ?
C3 C4 H4 115.8 . . ?
C5 C4 C2 120.27(13) . . ?
C5 C4 C3 118.64(13) . . ?
C5 C4 H4 115.8 . . ?
C6 C5 C4 120.54(13) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C15 C14 C13 120.36(14) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a_320k
_database_code_depnum_ccdc_archive 'CCDC 1857574'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-anisyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C23 H22 O3'
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H22 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.8567(6)
_cell_length_b                   9.2431(2)
_cell_length_c                   15.1049(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.846(5)
_cell_angle_gamma                90
_cell_volume                     1795.70(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3993
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.3900
_cell_measurement_theta_min      2.2280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.39
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         2.639
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega   14.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00   60.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -19.0000  -60.0000 109

#__ type_ start__ end____ width___ exp.time_
  6 omega   12.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   57.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   72.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   57.0000  120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0513253000
_diffrn_orient_matrix_UB_12      -0.0004872000
_diffrn_orient_matrix_UB_13      0.0003413000
_diffrn_orient_matrix_UB_21      -0.0135806000
_diffrn_orient_matrix_UB_22      0.0559403000
_diffrn_orient_matrix_UB_23      -0.0346170000
_diffrn_orient_matrix_UB_31      0.0149319000
_diffrn_orient_matrix_UB_32      0.0525304000
_diffrn_orient_matrix_UB_33      0.0368895000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3321
_reflns_number_total             4773
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.050
_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)+(0.0560P)²+0.2130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1298
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13662(8) 0.35572(9) 0.44122(7) 0.0415(2) Uani 1 1 d . . . . .
H1 H 0.135283 0.440856 0.425548 0.062 Uiso 1 1 calc GR . . . .
O2 O 0.59170(10) 0.27674(16) 0.75425(9) 0.0801(4) Uani 1 1 d . . . . .
O3 O 0.16574(9) -0.31970(10) 0.49470(8) 0.0545(3) Uani 1 1 d . . . . .
C1 C 0.17145(10) 0.26819(13) 0.38045(9) 0.0338(3) Uani 1 1 d . . . . .
C2 C 0.27721(10) 0.32535(13) 0.38545(9) 0.0357(3) Uani 1 1 d . . . . .
C3 C 0.26871(12) 0.46019(15) 0.32626(10) 0.0459(3) Uani 1 1 d . . . . .
H3 H 0.325333 0.530343 0.352082 0.055 Uiso 1 1 calc R . . . .
C4 C 0.30049(13) 0.30690(16) 0.29625(11) 0.0491(4) Uani 1 1 d . . . . .
H4 H 0.374018 0.295260 0.305910 0.059 Uiso 1 1 calc R . . . .
C5 C 0.22638(16) 0.23357(17) 0.21296(11) 0.0567(4) Uani 1 1 d . . . . .
H5 H 0.248272 0.198675 0.165783 0.068 Uiso 1 1 calc R . . . .
C6 C 0.12849(15) 0.21637(16) 0.20407(11) 0.0541(4) Uani 1 1 d . . . . .
H6 H 0.082920 0.163096 0.153553 0.065 Uiso 1 1 calc R . . . .
C7 C 0.09145(12) 0.28384(14) 0.27651(10) 0.0427(3) Uani 1 1 d . . . . .
H7 H 0.023852 0.243957 0.270772 0.051 Uiso 1 1 calc R . . . .
C8 C 0.08124(13) 0.44131(16) 0.24775(11) 0.0510(4) Uani 1 1 d . . . . .
H8 H 0.016336 0.481752 0.214449 0.061 Uiso 1 1 calc R . . . .
C9 C 0.16695(14) 0.52065(16) 0.27105(10) 0.0501(4) Uani 1 1 d . . . . .
H9 H 0.161922 0.616815 0.251734 0.060 Uiso 1 1 calc R . . . .
C10 C 0.36405(10) 0.31827(14) 0.48160(10) 0.0379(3) Uani 1 1 d . . . . .
C11 C 0.37504(12) 0.42453(16) 0.54902(11) 0.0461(3) Uani 1 1 d . . . . .
H11 H 0.331193 0.504492 0.532346 0.055 Uiso 1 1 calc R . . . .
C12 C 0.44957(12) 0.41583(17) 0.64104(11) 0.0525(4) Uani 1 1 d . . . . .
H12 H 0.454474 0.487957 0.685444 0.063 Uiso 1 1 calc R . . . .
C13 C 0.51603(12) 0.29886(18) 0.66549(11) 0.0528(4) Uani 1 1 d . . . . .
C14 C 0.50947(13) 0.19498(18) 0.59802(13) 0.0612(5) Uani 1 1 d . . . . .
H14 H 0.556179 0.118182 0.613606 0.073 Uiso 1 1 calc R . . . .
C15 C 0.43420(12) 0.20411(16) 0.50766(12) 0.0524(4) Uani 1 1 d . . . . .
H15 H 0.430302 0.132430 0.463253 0.063 Uiso 1 1 calc R . . . .
C16 C 0.59513(18) 0.3739(3) 0.82815(14) 0.0923(7) Uani 1 1 d . . . . .
H16A H 0.616075 0.467864 0.814948 0.138 Uiso 1 1 calc GR . . . .
H16B H 0.644174 0.339319 0.887876 0.138 Uiso 1 1 calc GR . . . .
H16C H 0.527462 0.380172 0.831590 0.138 Uiso 1 1 calc GR . . . .
C17 C 0.17464(10) 0.11259(12) 0.41533(9) 0.0325(3) Uani 1 1 d . . . . .
C18 C 0.13185(11) 0.07694(14) 0.48173(9) 0.0383(3) Uani 1 1 d . . . . .
H18 H 0.105402 0.150264 0.508339 0.046 Uiso 1 1 calc R . . . .
C19 C 0.12710(11) -0.06541(14) 0.51003(10) 0.0414(3) Uani 1 1 d . . . . .
H19 H 0.097228 -0.086121 0.554456 0.050 Uiso 1 1 calc R . . . .
C20 C 0.16674(11) -0.17564(13) 0.47210(10) 0.0384(3) Uani 1 1 d . . . . .
C21 C 0.21314(12) -0.14158(14) 0.40794(10) 0.0428(3) Uani 1 1 d . . . . .
H21 H 0.242056 -0.214613 0.383357 0.051 Uiso 1 1 calc R . . . .
C22 C 0.21684(11) -0.00021(14) 0.38016(10) 0.0404(3) Uani 1 1 d . . . . .
H22 H 0.248274 0.020349 0.336887 0.049 Uiso 1 1 calc R . . . .
C23 C 0.13443(18) -0.35617(18) 0.57138(14) 0.0711(6) Uani 1 1 d . . . . .
H23A H 0.063274 -0.328219 0.555776 0.107 Uiso 1 1 calc GR . . . .
H23B H 0.177696 -0.306286 0.627988 0.107 Uiso 1 1 calc GR . . . .
H23C H 0.141173 -0.458665 0.582209 0.107 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 H1 0.8200 . ?
O1 C1 1.4351(15) . ?
O2 C13 1.3757(18) . ?
O2 C16 1.419(3) . ?
O3 C20 1.3759(15) . ?
O3 C23 1.4203(19) . ?
C1 C2 1.5329(18) . ?
C1 C7 1.5555(18) . ?
C1 C17 1.5266(17) . ?
C2 C3 1.5128(19) . ?
C2 C4 1.5073(19) . ?
C2 C10 1.5036(18) . ?
C3 H3 0.9800 . ?
C3 C4 1.599(2) . ?
C3 C9 1.456(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.461(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.322(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.506(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.5104(19) . ?
C8 H8 0.9300 . ?
C8 C9 1.327(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 C15 1.389(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.392(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(2) . ?
C13 C14 1.378(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(2) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.3815(18) . ?
C17 C22 1.3938(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3926(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.3793(19) . ?
C20 C21 1.384(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.3792(19) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C13 O2 C16 117.56(16) . . ?
C20 O3 C23 117.80(12) . . ?
O1 C1 C2 108.48(10) . . ?
O1 C1 C7 108.07(10) . . ?
O1 C1 C17 106.49(10) . . ?
C2 C1 C7 109.08(11) . . ?
C17 C1 C2 113.78(10) . . ?
C17 C1 C7 110.74(10) . . ?
C3 C2 C1 113.09(11) . . ?
C4 C2 C1 115.82(12) . . ?
C4 C2 C3 63.92(10) . . ?
C10 C2 C1 116.07(11) . . ?
C10 C2 C3 117.71(11) . . ?
C10 C2 C4 119.86(12) . . ?
C2 C3 H3 115.8 . . ?
C2 C3 C4 57.88(9) . . ?
C4 C3 H3 115.8 . . ?
C9 C3 C2 120.02(13) . . ?
C9 C3 H3 115.8 . . ?
C9 C3 C4 119.21(13) . . ?
C2 C4 C3 58.21(9) . . ?
C2 C4 H4 115.8 . . ?
C3 C4 H4 115.8 . . ?
C5 C4 C2 120.43(14) . . ?
C5 C4 C3 118.41(14) . . ?
C5 C4 H4 115.8 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.60(14) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.38(14) . . ?
C7 C6 H6 120.3 . . ?
C1 C7 H7 110.7 . . ?
C6 C7 C1 112.79(12) . . ?
C6 C7 H7 110.7 . . ?
C6 C7 C8 102.18(12) . . ?
C8 C7 C1 109.59(11) . . ?
C8 C7 H7 110.7 . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.52(14) . . ?
C9 C8 H8 120.7 . . ?
C3 C9 H9 119.3 . . ?
C8 C9 C3 121.34(13) . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C2 120.66(12) . . ?
C11 C10 C15 117.23(13) . . ?
C15 C10 C2 122.08(13) . . ?
C10 C11 H11 118.9 . . ?
C10 C11 C12 122.16(13) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.10(14) . . ?
C13 C12 H12 120.5 . . ?
O2 C13 C12 124.65(16) . . ?
O2 C13 C14 115.70(15) . . ?
C14 C13 C12 119.65(14) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.47(15) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.29(15) . . ?
C14 C15 H15 119.4 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C1 120.67(11) . . ?
C18 C17 C22 116.91(11) . . ?
C22 C17 C1 122.39(12) . . ?
C17 C18 H18 119.0 . . ?
C17 C18 C19 122.03(12) . . ?
C19 C18 H18 119.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.92(13) . . ?
C20 C19 H19 120.0 . . ?
O3 C20 C19 124.71(13) . . ?
O3 C20 C21 116.37(12) . . ?
C19 C20 C21 118.91(12) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.54(12) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.63(13) . . ?
C21 C22 H22 119.2 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a_370k
_database_code_depnum_ccdc_archive 'CCDC 1857575'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-anisyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C23 H22 O3'
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H22 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.9193(8)
_cell_length_b                   9.2488(3)
_cell_length_c                   15.1658(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.938(6)
_cell_angle_gamma                90
_cell_volume                     1811.01(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3300
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1170
_cell_measurement_theta_min      2.7250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.39
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16854
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.994
_diffrn_reflns_theta_min         2.636
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    9.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   57.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   19.0000   30.0000 109

#__ type_ start__ end____ width___ exp.time_
  3 omega   22.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -40.00   44.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -57.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -10.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -100.0000 -180.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0511652000
_diffrn_orient_matrix_UB_12      -0.0005073000
_diffrn_orient_matrix_UB_13      -0.0005411000
_diffrn_orient_matrix_UB_21      0.0134516000
_diffrn_orient_matrix_UB_22      0.0559091000
_diffrn_orient_matrix_UB_23      0.0345132000
_diffrn_orient_matrix_UB_31      -0.0148069000
_diffrn_orient_matrix_UB_32      0.0524840000
_diffrn_orient_matrix_UB_33      -0.0367713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3028
_reflns_number_total             4808
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.021
_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)+(0.0580P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1374
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C7(H7), C3(H3), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C21(H21), C19(H19), C11(H11), C9(H9), C8(H8), C15(H15),
 C12(H12), C6(H6), C5(H5), C14(H14)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.86301(8) 0.85576(10) 0.55912(7) 0.0501(3) Uani 1 1 d . . . . .
H1 H 0.862703 0.940977 0.573931 0.075 Uiso 1 1 calc GR . . . .
C17 C 0.82529(10) 0.61264(13) 0.58433(9) 0.0396(3) Uani 1 1 d . . . . .
O3 O 0.83482(10) 0.18142(11) 0.50471(8) 0.0654(3) Uani 1 1 d . . . . .
C20 C 0.83340(12) 0.32516(14) 0.52727(10) 0.0465(3) Uani 1 1 d . . . . .
C1 C 0.82839(11) 0.76780(13) 0.61935(9) 0.0404(3) Uani 1 1 d . . . . .
C10 C 0.63629(11) 0.81783(15) 0.51828(11) 0.0463(3) Uani 1 1 d . . . . .
C2 C 0.72266(11) 0.82467(14) 0.61406(10) 0.0440(3) Uani 1 1 d . . . . .
C18 C 0.86778(12) 0.57740(15) 0.51831(10) 0.0466(3) Uani 1 1 d . . . . .
H18 H 0.894083 0.650851 0.491933 0.056 Uiso 1 1 calc R . . . .
C22 C 0.78365(12) 0.49955(15) 0.61924(11) 0.0499(4) Uani 1 1 d . . . . .
H22 H 0.752643 0.519573 0.662586 0.060 Uiso 1 1 calc R . . . .
C21 C 0.78731(13) 0.35869(15) 0.59106(11) 0.0520(4) Uani 1 1 d . . . . .
H21 H 0.758457 0.285454 0.615250 0.062 Uiso 1 1 calc R . . . .
C7 C 0.90766(13) 0.78349(15) 0.72318(11) 0.0522(4) Uani 1 1 d . . . . .
H7 H 0.975154 0.743909 0.729245 0.063 Uiso 1 1 calc R . . . .
C19 C 0.87254(13) 0.43577(15) 0.48996(11) 0.0509(4) Uani 1 1 d . . . . .
H19 H 0.902240 0.415566 0.445659 0.061 Uiso 1 1 calc R . . . .
C11 C 0.62547(12) 0.92316(17) 0.45069(12) 0.0565(4) Uani 1 1 d . . . . .
H11 H 0.669853 1.002341 0.466830 0.068 Uiso 1 1 calc R . . . .
C9 C 0.83236(15) 1.01973(17) 0.72837(11) 0.0610(5) Uani 1 1 d . . . . .
H9 H 0.837348 1.115792 0.747711 0.073 Uiso 1 1 calc R . . . .
C3 C 0.73143(14) 0.95946(17) 0.67287(11) 0.0566(4) Uani 1 1 d . . . . .
H3 H 0.675003 1.029547 0.647130 0.068 Uiso 1 1 calc R . . . .
C8 C 0.91744(15) 0.94020(17) 0.75192(12) 0.0632(5) Uani 1 1 d . . . . .
H8 H 0.982029 0.980479 0.785610 0.076 Uiso 1 1 calc R . . . .
C15 C 0.56620(14) 0.70440(18) 0.49191(13) 0.0641(5) Uani 1 1 d . . . . .
H15 H 0.570047 0.632646 0.536066 0.077 Uiso 1 1 calc R . . . .
C12 C 0.55066(13) 0.91495(19) 0.35952(12) 0.0645(5) Uani 1 1 d . . . . .
H12 H 0.545433 0.987399 0.315433 0.077 Uiso 1 1 calc R . . . .
C13 C 0.48443(13) 0.7988(2) 0.33503(13) 0.0648(5) Uani 1 1 d . . . . .
O2 O 0.40861(11) 0.77705(17) 0.24673(10) 0.0968(5) Uani 1 1 d . . . . .
C6 C 0.87081(17) 0.71634(17) 0.79505(12) 0.0661(5) Uani 1 1 d . . . . .
H6 H 0.916256 0.663702 0.845746 0.079 Uiso 1 1 calc R . . . .
C4 C 0.69972(14) 0.80574(18) 0.70282(12) 0.0611(4) Uani 1 1 d . . . . .
H4 H 0.626474 0.794208 0.693133 0.073 Uiso 1 1 calc R . . . .
C5 C 0.77307(18) 0.73283(18) 0.78550(12) 0.0686(5) Uani 1 1 d . . . . .
H5 H 0.751019 0.697419 0.832172 0.082 Uiso 1 1 calc R . . . .
C23 C 0.86628(19) 0.14481(19) 0.42888(15) 0.0845(7) Uani 1 1 d . . . . .
H23A H 0.823351 0.194501 0.372296 0.127 Uiso 1 1 calc GR . . . .
H23B H 0.859635 0.042344 0.418211 0.127 Uiso 1 1 calc GR . . . .
H23C H 0.937197 0.172754 0.444729 0.127 Uiso 1 1 calc GR . . . .
C14 C 0.49125(15) 0.6953(2) 0.40229(15) 0.0745(5) Uani 1 1 d . . . . .
H14 H 0.444703 0.618588 0.386881 0.089 Uiso 1 1 calc R . . . .
C16 C 0.4047(2) 0.8736(3) 0.17303(16) 0.1113(9) Uani 1 1 d . . . . .
H16A H 0.356075 0.838491 0.113557 0.167 Uiso 1 1 calc GR . . . .
H16B H 0.472126 0.880495 0.169708 0.167 Uiso 1 1 calc GR . . . .
H16C H 0.383406 0.967420 0.185870 0.167 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 H1 0.8200 . ?
O1 C1 1.4344(15) . ?
C17 C1 1.5252(18) . ?
C17 C18 1.3788(19) . ?
C17 C22 1.3926(19) . ?
O3 C20 1.3748(16) . ?
O3 C23 1.416(2) . ?
C20 C21 1.381(2) . ?
C20 C19 1.376(2) . ?
C1 C2 1.5364(19) . ?
C1 C7 1.556(2) . ?
C10 C2 1.502(2) . ?
C10 C11 1.381(2) . ?
C10 C15 1.386(2) . ?
C2 C3 1.511(2) . ?
C2 C4 1.505(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.3879(19) . ?
C22 H22 0.9300 . ?
C22 C21 1.378(2) . ?
C21 H21 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.505(2) . ?
C7 C6 1.502(2) . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.388(2) . ?
C9 H9 0.9300 . ?
C9 C3 1.452(2) . ?
C9 C8 1.325(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.604(2) . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.372(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(2) . ?
C13 O2 1.375(2) . ?
C13 C14 1.376(3) . ?
O2 C16 1.416(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.322(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.454(3) . ?
C5 H5 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C14 H14 0.9300 . ?
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
C1 O1 H1 109.5 . . ?
C18 C17 C1 120.75(11) . . ?
C18 C17 C22 116.80(12) . . ?
C22 C17 C1 122.41(12) . . ?
C20 O3 C23 118.09(12) . . ?
O3 C20 C21 116.43(12) . . ?
O3 C20 C19 124.88(14) . . ?
C19 C20 C21 118.68(13) . . ?
O1 C1 C17 106.52(10) . . ?
O1 C1 C2 108.40(10) . . ?
O1 C1 C7 108.16(11) . . ?
C17 C1 C2 113.70(11) . . ?
C17 C1 C7 110.94(11) . . ?
C2 C1 C7 108.92(11) . . ?
C11 C10 C2 120.95(13) . . ?
C11 C10 C15 116.75(15) . . ?
C15 C10 C2 122.27(14) . . ?
C10 C2 C1 116.18(11) . . ?
C10 C2 C3 117.69(12) . . ?
C10 C2 C4 119.97(13) . . ?
C3 C2 C1 112.77(12) . . ?
C4 C2 C1 115.63(13) . . ?
C4 C2 C3 64.25(10) . . ?
C17 C18 H18 119.0 . . ?
C17 C18 C19 122.07(13) . . ?
C19 C18 H18 119.0 . . ?
C17 C22 H22 119.2 . . ?
C21 C22 C17 121.56(13) . . ?
C21 C22 H22 119.2 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.68(13) . . ?
C22 C21 H21 119.7 . . ?
C1 C7 H7 110.7 . . ?
C8 C7 C1 109.65(12) . . ?
C8 C7 H7 110.7 . . ?
C6 C7 C1 113.00(13) . . ?
C6 C7 H7 110.7 . . ?
C6 C7 C8 101.91(13) . . ?
C20 C19 C18 120.15(13) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C10 C11 H11 118.9 . . ?
C10 C11 C12 122.28(15) . . ?
C12 C11 H11 118.9 . . ?
C3 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C3 121.12(15) . . ?
C2 C3 H3 115.8 . . ?
C2 C3 C4 57.71(9) . . ?
C9 C3 C2 120.41(14) . . ?
C9 C3 H3 115.8 . . ?
C9 C3 C4 119.02(14) . . ?
C4 C3 H3 115.8 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.80(16) . . ?
C9 C8 H8 120.6 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.65(16) . . ?
C14 C15 H15 119.2 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.36(16) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 O2 124.84(17) . . ?
C12 C13 C14 119.36(17) . . ?
O2 C13 C14 115.80(17) . . ?
C13 O2 C16 117.72(18) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 C7 119.30(16) . . ?
C5 C6 H6 120.4 . . ?
C2 C4 C3 58.05(9) . . ?
C2 C4 H4 115.8 . . ?
C3 C4 H4 115.8 . . ?
C5 C4 C2 120.66(15) . . ?
C5 C4 C3 118.46(15) . . ?
C5 C4 H4 115.8 . . ?
C6 C5 C4 120.70(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C14 C13 120.53(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a_16srv452
_database_code_depnum_ccdc_archive 'CCDC 1857576'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2016-11-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-anisyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;

_chemical_formula_moiety         'C23 H22 O3'
_chemical_formula_sum            'C23 H22 O3'
_chemical_formula_weight         346.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.5882(7)
_cell_length_b                   9.2068(5)
_cell_length_c                   14.8687(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.2938(18)
_cell_angle_gamma                90
_cell_volume                     1733.14(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9789
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.52
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0855 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.9402.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_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             736
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34653
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         2.656
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3992
_reflns_number_total             4609
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.044
_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)+(0.0550P)²+0.7300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.13513(6) 0.35567(8) 0.44218(5) 0.01393(16) Uani 1 1 d . . . . .
O2 O 0.59168(7) 0.27553(11) 0.75727(6) 0.0261(2) Uani 1 1 d . . . . .
O3 O 0.16755(7) -0.32310(8) 0.49295(6) 0.01847(18) Uani 1 1 d . . . . .
C1 C 0.17046(8) 0.26899(11) 0.37966(7) 0.01120(19) Uani 1 1 d . . . . .
C2 C 0.27767(8) 0.32708(11) 0.38349(7) 0.01209(19) Uani 1 1 d . . . . .
C3 C 0.26872(9) 0.46276(12) 0.32354(8) 0.0152(2) Uani 1 1 d . . . . .
C4 C 0.30157(9) 0.31016(12) 0.29256(8) 0.0159(2) Uani 1 1 d . . . . .
C5 C 0.22631(10) 0.23573(12) 0.20835(8) 0.0186(2) Uani 1 1 d . . . . .
C6 C 0.12617(9) 0.21689(12) 0.20044(8) 0.0182(2) Uani 1 1 d . . . . .
C7 C 0.08864(8) 0.28453(11) 0.27498(8) 0.0139(2) Uani 1 1 d . . . . .
C8 C 0.07704(9) 0.44269(12) 0.24635(8) 0.0166(2) Uani 1 1 d . . . . .
C9 C 0.16444(9) 0.52366(12) 0.26881(7) 0.0165(2) Uani 1 1 d . . . . .
C10 C 0.36533(8) 0.32039(11) 0.48015(7) 0.0128(2) Uani 1 1 d . . . . .
C11 C 0.37609(8) 0.42881(12) 0.54826(8) 0.0158(2) Uani 1 1 d . . . . .
C12 C 0.45088(9) 0.41945(12) 0.64178(8) 0.0173(2) Uani 1 1 d . . . . .
C13 C 0.51703(8) 0.29887(13) 0.66724(8) 0.0174(2) Uani 1 1 d . . . . .
C14 C 0.51060(9) 0.19287(13) 0.59878(9) 0.0197(2) Uani 1 1 d . . . . .
C15 C 0.43511(9) 0.20306(12) 0.50667(8) 0.0174(2) Uani 1 1 d . . . . .
C16 C 0.59337(11) 0.37501(18) 0.83126(9) 0.0299(3) Uani 1 1 d . . . . .
C17 C 0.17470(8) 0.11270(11) 0.41445(7) 0.01123(19) Uani 1 1 d . . . . .
C18 C 0.13102(8) 0.07522(11) 0.48248(7) 0.0129(2) Uani 1 1 d . . . . .
C19 C 0.12708(8) -0.06854(12) 0.51066(7) 0.0143(2) Uani 1 1 d . . . . .
C20 C 0.16786(8) -0.17817(11) 0.47049(7) 0.0132(2) Uani 1 1 d . . . . .
C21 C 0.21517(8) -0.14258(11) 0.40451(8) 0.0141(2) Uani 1 1 d . . . . .
C22 C 0.21848(8) 0.00061(11) 0.37707(7) 0.0137(2) Uani 1 1 d . . . . .
C23 C 0.13886(11) -0.35898(13) 0.57381(9) 0.0239(3) Uani 1 1 d . . . . .
H1 H 0.1354(13) 0.444(2) 0.4248(12) 0.033(4) Uiso 1 1 d . . . . .
H3 H 0.3259(11) 0.5305(16) 0.3475(10) 0.018(3) Uiso 1 1 d . . . . .
H4 H 0.3768(12) 0.3048(16) 0.3010(10) 0.021(4) Uiso 1 1 d . . . . .
H5 H 0.2509(12) 0.2063(17) 0.1583(11) 0.025(4) Uiso 1 1 d . . . . .
H6 H 0.0754(12) 0.1692(17) 0.1437(11) 0.024(4) Uiso 1 1 d . . . . .
H7 H 0.0211(11) 0.2444(15) 0.2731(10) 0.017(3) Uiso 1 1 d . . . . .
H8 H 0.0069(12) 0.4788(17) 0.2072(11) 0.026(4) Uiso 1 1 d . . . . .
H9 H 0.1609(11) 0.6238(17) 0.2473(10) 0.020(3) Uiso 1 1 d . . . . .
H11 H 0.3313(12) 0.5135(18) 0.5314(11) 0.027(4) Uiso 1 1 d . . . . .
H12 H 0.4542(12) 0.4932(17) 0.6871(11) 0.023(4) Uiso 1 1 d . . . . .
H14 H 0.5604(13) 0.1115(18) 0.6185(11) 0.028(4) Uiso 1 1 d . . . . .
H15 H 0.4300(12) 0.1264(17) 0.4605(11) 0.024(4) Uiso 1 1 d . . . . .
H16A H 0.6183(14) 0.470(2) 0.8213(12) 0.035(4) Uiso 1 1 d . . . . .
H16B H 0.5213(14) 0.3846(19) 0.8348(12) 0.037(4) Uiso 1 1 d . . . . .
H16C H 0.6422(15) 0.333(2) 0.8910(13) 0.040(5) Uiso 1 1 d . . . . .
H18 H 0.1039(11) 0.1507(16) 0.5109(10) 0.019(3) Uiso 1 1 d . . . . .
H19 H 0.0972(12) -0.0886(16) 0.5600(11) 0.024(4) Uiso 1 1 d . . . . .
H21 H 0.2456(11) -0.2191(16) 0.3797(10) 0.018(3) Uiso 1 1 d . . . . .
H22 H 0.2513(11) 0.0231(15) 0.3308(10) 0.016(3) Uiso 1 1 d . . . . .
H23A H 0.1486(12) -0.4623(18) 0.5811(11) 0.024(4) Uiso 1 1 d . . . . .
H23B H 0.0641(14) -0.3341(18) 0.5625(12) 0.034(4) Uiso 1 1 d . . . . .
H23C H 0.1839(14) -0.3083(19) 0.6321(13) 0.035(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4337(12) . ?
O1 H1 0.852(18) . ?
O2 C13 1.3715(13) . ?
O2 C16 1.4253(17) . ?
O3 C20 1.3759(13) . ?
O3 C23 1.4307(14) . ?
C1 C2 1.5334(14) . ?
C1 C7 1.5563(14) . ?
C1 C17 1.5231(14) . ?
C2 C3 1.5137(14) . ?
C2 C4 1.5088(14) . ?
C2 C10 1.4982(14) . ?
C3 C4 1.5920(15) . ?
C3 C9 1.4653(15) . ?
C3 H3 0.958(15) . ?
C4 C5 1.4673(16) . ?
C4 H4 0.986(15) . ?
C5 C6 1.3339(17) . ?
C5 H5 0.958(15) . ?
C6 C7 1.5122(15) . ?
C6 H6 0.979(16) . ?
C7 C8 1.5092(15) . ?
C7 H7 0.980(14) . ?
C8 C9 1.3377(16) . ?
C8 H8 0.978(16) . ?
C9 H9 0.971(15) . ?
C10 C11 1.3915(15) . ?
C10 C15 1.3964(15) . ?
C11 C12 1.3955(15) . ?
C11 H11 0.965(16) . ?
C12 C13 1.3916(16) . ?
C12 H12 0.946(15) . ?
C13 C14 1.3898(16) . ?
C14 C15 1.3844(15) . ?
C14 H14 0.980(17) . ?
C15 H15 0.970(16) . ?
C16 H16A 0.965(19) . ?
C16 H16B 1.003(18) . ?
C16 H16C 0.975(19) . ?
C17 C18 1.3894(14) . ?
C17 C22 1.4028(14) . ?
C18 C19 1.3952(15) . ?
C18 H18 0.954(15) . ?
C19 C20 1.3867(15) . ?
C19 H19 0.977(15) . ?
C20 C21 1.3932(15) . ?
C21 C22 1.3855(15) . ?
C21 H21 0.956(15) . ?
C22 H22 0.969(14) . ?
C23 H23A 0.961(16) . ?
C23 H23B 0.994(18) . ?
C23 H23C 0.979(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 107.2(12) . . ?
C13 O2 C16 116.85(10) . . ?
C20 O3 C23 116.98(9) . . ?
O1 C1 C2 108.61(8) . . ?
O1 C1 C7 108.14(8) . . ?
O1 C1 C17 106.61(8) . . ?
C2 C1 C7 109.21(8) . . ?
C17 C1 C2 113.50(8) . . ?
C17 C1 C7 110.59(8) . . ?
C3 C2 C1 113.20(8) . . ?
C4 C2 C1 116.20(9) . . ?
C4 C2 C3 63.57(7) . . ?
C10 C2 C1 115.78(8) . . ?
C10 C2 C3 117.69(9) . . ?
C10 C2 C4 120.03(9) . . ?
C2 C3 C4 58.06(7) . . ?
C2 C3 H3 116.0(9) . . ?
C4 C3 H3 114.0(9) . . ?
C9 C3 C2 119.83(9) . . ?
C9 C3 C4 119.55(9) . . ?
C9 C3 H3 116.5(9) . . ?
C2 C4 C3 58.36(7) . . ?
C2 C4 H4 116.3(8) . . ?
C3 C4 H4 113.2(9) . . ?
C5 C4 C2 120.18(9) . . ?
C5 C4 C3 118.51(9) . . ?
C5 C4 H4 117.0(9) . . ?
C4 C5 H5 117.6(9) . . ?
C6 C5 C4 120.56(10) . . ?
C6 C5 H5 121.8(9) . . ?
C5 C6 C7 119.12(10) . . ?
C5 C6 H6 120.8(9) . . ?
C7 C6 H6 119.8(9) . . ?
C1 C7 H7 108.4(8) . . ?
C6 C7 C1 112.74(9) . . ?
C6 C7 H7 112.6(8) . . ?
C8 C7 C1 109.53(8) . . ?
C8 C7 C6 102.65(9) . . ?
C8 C7 H7 110.8(8) . . ?
C7 C8 H8 118.4(9) . . ?
C9 C8 C7 118.36(10) . . ?
C9 C8 H8 123.0(9) . . ?
C3 C9 H9 117.9(9) . . ?
C8 C9 C3 121.14(10) . . ?
C8 C9 H9 120.9(9) . . ?
C11 C10 C2 120.37(9) . . ?
C11 C10 C15 117.93(10) . . ?
C15 C10 C2 121.63(9) . . ?
C10 C11 C12 121.80(10) . . ?
C10 C11 H11 120.1(9) . . ?
C12 C11 H11 118.1(9) . . ?
C11 C12 H12 119.6(9) . . ?
C13 C12 C11 119.02(10) . . ?
C13 C12 H12 121.3(9) . . ?
O2 C13 C12 124.48(10) . . ?
O2 C13 C14 115.62(10) . . ?
C14 C13 C12 119.90(10) . . ?
C13 C14 H14 117.7(9) . . ?
C15 C14 C13 120.26(10) . . ?
C15 C14 H14 122.0(9) . . ?
C10 C15 H15 119.8(9) . . ?
C14 C15 C10 121.00(10) . . ?
C14 C15 H15 119.2(9) . . ?
O2 C16 H16A 111.7(10) . . ?
O2 C16 H16B 110.7(10) . . ?
O2 C16 H16C 105.3(11) . . ?
H16A C16 H16B 109.4(14) . . ?
H16A C16 H16C 109.6(15) . . ?
H16B C16 H16C 110.0(14) . . ?
C18 C17 C1 120.56(9) . . ?
C18 C17 C22 117.42(9) . . ?
C22 C17 C1 121.98(9) . . ?
C17 C18 C19 121.83(9) . . ?
C17 C18 H18 118.5(9) . . ?
C19 C18 H18 119.6(9) . . ?
C18 C19 H19 118.5(9) . . ?
C20 C19 C18 119.75(10) . . ?
C20 C19 H19 121.7(9) . . ?
O3 C20 C19 124.36(10) . . ?
O3 C20 C21 116.23(9) . . ?
C19 C20 C21 119.39(10) . . ?
C20 C21 H21 118.2(9) . . ?
C22 C21 C20 120.25(10) . . ?
C22 C21 H21 121.5(9) . . ?
C17 C22 H22 119.7(8) . . ?
C21 C22 C17 121.30(10) . . ?
C21 C22 H22 119.0(8) . . ?
O3 C23 H23A 104.7(9) . . ?
O3 C23 H23B 112.2(10) . . ?
O3 C23 H23C 111.1(10) . . ?
H23A C23 H23B 109.8(13) . . ?
H23A C23 H23C 110.8(14) . . ?
H23B C23 H23C 108.2(14) . . ?

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 O3 0.852(18) 2.345(18) 3.0446(11) 139.6(15) 1_565

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
C1 C2 C3 C4 -108.87(10) . . . . ?
C1 C2 C3 C9 -0.66(13) . . . . ?
C1 C2 C4 C3 104.22(10) . . . . ?
C1 C2 C4 C5 -2.65(14) . . . . ?
C1 C2 C10 C11 -82.95(12) . . . . ?
C1 C2 C10 C15 93.83(12) . . . . ?
C1 C7 C6 C5 -41.90(14) . . . . ?
C1 C7 C8 C9 43.24(13) . . . . ?
C2 C1 C7 C6 52.92(11) . . . . ?
C2 C1 C7 C8 -60.70(11) . . . . ?
C2 C1 C17 C18 130.05(10) . . . . ?
C2 C1 C17 C22 -52.48(12) . . . . ?
C2 C3 C4 C5 109.72(11) . . . . ?
C2 C3 C9 C8 -20.36(16) . . . . ?
C2 C4 C3 C2 0.000(1) . . . . ?
C2 C4 C3 C9 -108.69(11) . . . . ?
C2 C4 C5 C6 18.03(16) . . . . ?
C3 C2 C1 O1 -78.24(10) . . . . ?
C3 C2 C1 C7 39.49(11) . . . . ?
C3 C2 C1 C17 163.37(8) . . . . ?
C3 C2 C4 C5 -106.87(11) . . . . ?
C3 C2 C10 C11 55.42(13) . . . . ?
C3 C2 C10 C15 -127.80(11) . . . . ?
C3 C4 C2 C3 0.000(0) . . . . ?
C3 C4 C2 C10 -108.18(10) . . . . ?
C3 C4 C5 C6 -49.98(15) . . . . ?
C3 C9 C8 C7 -2.64(16) . . . . ?
C4 C2 C1 O1 -149.05(9) . . . . ?
C4 C2 C1 C7 -31.31(12) . . . . ?
C4 C2 C1 C17 92.57(10) . . . . ?
C4 C2 C3 C9 108.21(11) . . . . ?
C4 C2 C10 C11 129.32(11) . . . . ?
C4 C2 C10 C15 -53.90(14) . . . . ?
C4 C3 C2 C4 0.000(0) . . . . ?
C4 C3 C2 C10 111.74(10) . . . . ?
C4 C3 C9 C8 47.56(15) . . . . ?
C4 C5 C6 C7 5.25(16) . . . . ?
C5 C4 C2 C10 144.95(10) . . . . ?
C5 C4 C3 C9 1.03(14) . . . . ?
C5 C6 C7 C8 75.84(12) . . . . ?
C6 C7 C1 O1 170.94(9) . . . . ?
C6 C7 C1 C17 -72.67(11) . . . . ?
C6 C7 C8 C9 -76.76(12) . . . . ?
C7 C1 C2 C10 179.70(8) . . . . ?
C7 C1 C17 C18 -106.81(10) . . . . ?
C7 C1 C17 C22 70.65(12) . . . . ?
C8 C7 C1 O1 57.33(11) . . . . ?
C8 C7 C1 C17 173.72(9) . . . . ?
C9 C3 C2 C10 -140.05(10) . . . . ?
C10 C2 C1 O1 61.97(11) . . . . ?
C10 C2 C1 C17 -56.42(11) . . . . ?
C12 C13 O2 C16 6.52(17) . . . . ?
C14 C13 O2 C16 -174.22(11) . . . . ?
C18 C17 C1 O1 10.52(12) . . . . ?
C19 C20 O3 C23 -10.47(16) . . . . ?
C21 C20 O3 C23 167.92(10) . . . . ?
C22 C17 C1 O1 -172.01(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
####################################################################### 
# 
# 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_1b_370k
_database_code_depnum_ccdc_archive 'CCDC 1857583'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1


_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-fluorophenyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C21 H16 F2 O'
_chemical_formula_sum            'C21 H16 F2 O'
_chemical_formula_weight         322.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H16 F2 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.8240(5)
_cell_length_b                   6.3040(4)
_cell_length_c                   25.0331(18)
_cell_angle_alpha                90
_cell_angle_beta                 90.602(5)
_cell_angle_gamma                90
_cell_volume                     1550.22(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2121
_cell_measurement_temperature    370(2)
_cell_measurement_theta_max      25.2050
_cell_measurement_theta_min      2.4330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14864
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         3.187
_diffrn_ambient_temperature      370.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    6.00  104.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029   77.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   59.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   56.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029  178.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega   44.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029   77.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029 -100.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega  -19.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029 -100.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
  7 omega  -39.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029    0.0000 -150.0000 128
;
_diffrn_measurement_device       'Xcalibur, Sapphire3'
_diffrn_measurement_device_type  '4-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0370685000
_diffrn_orient_matrix_UB_12      0.0657660000
_diffrn_orient_matrix_UB_13      -0.0176870000
_diffrn_orient_matrix_UB_21      -0.0600131000
_diffrn_orient_matrix_UB_22      0.0173652000
_diffrn_orient_matrix_UB_23      -0.0153450000
_diffrn_orient_matrix_UB_31      -0.0154331000
_diffrn_orient_matrix_UB_32      0.0896252000
_diffrn_orient_matrix_UB_33      0.0159563000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tubeEnhance (Mo) X-ray Source'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2158
_reflns_number_total             4124
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.012
_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)+(0.0490P)²+0.0370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C6(H6), C21(H21), C15(H15), C5(H5), C18(H18), C7(H7), C11(H11),
 C20(H20), C8(H8), C14(H14), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.90082(16) 1.0009(2) 0.59992(7) 0.0495(4) Uani 1 1 d . . . . .
O1 O 0.93935(15) 1.21558(19) 0.61146(6) 0.0654(4) Uani 1 1 d . . . . .
C1 C 0.82497(16) 0.9078(2) 0.65058(7) 0.0516(4) Uani 1 1 d . . . . .
C16 C 1.03142(16) 0.8809(2) 0.58838(6) 0.0479(4) Uani 1 1 d . . . . .
C10 C 0.92130(18) 0.8925(3) 0.69802(7) 0.0559(5) Uani 1 1 d . . . . .
C3 C 0.80364(17) 1.0018(3) 0.55290(7) 0.0569(5) Uani 1 1 d . . . . .
H3 H 0.841246 1.050636 0.518943 0.068 Uiso 1 1 calc R . . . .
C17 C 1.02897(17) 0.6833(3) 0.56390(7) 0.0550(4) Uani 1 1 d . . . . .
H17 H 0.945704 0.625767 0.553407 0.066 Uiso 1 1 calc R . . . .
C6 C 0.75483(18) 0.7003(3) 0.63677(9) 0.0609(5) Uani 1 1 d . . . . .
H6 H 0.755488 0.590416 0.661575 0.073 Uiso 1 1 calc R . . . .
C21 C 1.15727(19) 0.9627(3) 0.60267(8) 0.0646(5) Uani 1 1 d . . . . .
H21 H 1.162478 1.095123 0.618927 0.078 Uiso 1 1 calc R . . . .
C15 C 0.9981(2) 0.7102(3) 0.70711(8) 0.0659(5) Uani 1 1 d . . . . .
H15 H 0.987503 0.594680 0.684333 0.079 Uiso 1 1 calc R . . . .
F2 F 1.38362(11) 0.5461(2) 0.55967(6) 0.1082(5) Uani 1 1 d . . . . .
C5 C 0.69266(18) 0.6724(3) 0.59008(10) 0.0663(5) Uani 1 1 d . . . . .
H5 H 0.644901 0.547365 0.583695 0.080 Uiso 1 1 calc R . . . .
C18 C 1.14661(18) 0.5696(3) 0.55467(8) 0.0642(5) Uani 1 1 d . . . . .
H18 H 1.143203 0.436371 0.538736 0.077 Uiso 1 1 calc R . . . .
C7 C 0.70151(19) 1.0475(3) 0.66040(9) 0.0638(5) Uani 1 1 d . . . . .
H7 H 0.678387 1.083985 0.695137 0.077 Uiso 1 1 calc R . . . .
C9 C 0.66150(19) 1.0732(3) 0.56471(9) 0.0666(5) Uani 1 1 d . . . . .
H9 H 0.615695 1.158620 0.537191 0.080 Uiso 1 1 calc R . . . .
C19 C 1.26695(19) 0.6573(4) 0.56945(8) 0.0693(5) Uani 1 1 d . . . . .
C4 C 0.69772(18) 0.8322(3) 0.54902(8) 0.0645(5) Uani 1 1 d . . . . .
H4 H 0.671612 0.786859 0.512889 0.077 Uiso 1 1 calc R . . . .
C11 C 0.9409(2) 1.0617(3) 0.73248(8) 0.0697(5) Uani 1 1 d . . . . .
H11 H 0.891480 1.185727 0.727016 0.084 Uiso 1 1 calc R . . . .
C20 C 1.2754(2) 0.8504(4) 0.59314(9) 0.0765(6) Uani 1 1 d . . . . .
H20 H 1.359657 0.906642 0.602837 0.092 Uiso 1 1 calc R . . . .
C8 C 0.62637(19) 1.1177(3) 0.61953(9) 0.0654(5) Uani 1 1 d . . . . .
H8 H 0.549018 1.197830 0.626437 0.078 Uiso 1 1 calc R . . . .
C14 C 1.0897(2) 0.6973(4) 0.74931(9) 0.0763(6) Uani 1 1 d . . . . .
H14 H 1.140197 0.574647 0.755264 0.092 Uiso 1 1 calc R . . . .
F1 F 1.19356(16) 0.8567(3) 0.82359(6) 0.1173(5) Uani 1 1 d . . . . .
C13 C 1.1041(2) 0.8693(4) 0.78198(9) 0.0795(6) Uani 1 1 d . . . . .
C12 C 1.0322(2) 1.0510(4) 0.77480(9) 0.0802(6) Uani 1 1 d . . . . .
H12 H 1.043969 1.165596 0.797794 0.096 Uiso 1 1 calc R . . . .
H1 H 0.869(3) 1.290(4) 0.6122(11) 0.120(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.4340(19) . ?
C2 C1 1.590(2) . ?
C2 C16 1.520(2) . ?
C2 C3 1.508(2) . ?
O1 H1 0.83(3) . ?
C1 C10 1.514(3) . ?
C1 C6 1.517(2) . ?
C1 C7 1.521(2) . ?
C16 C17 1.389(2) . ?
C16 C21 1.383(2) . ?
C10 C15 1.392(2) . ?
C10 C11 1.384(2) . ?
C3 H3 0.9800 . ?
C3 C9 1.500(2) . ?
C3 C4 1.494(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.325(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.383(3) . ?
F2 C19 1.368(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.441(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.353(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.331(3) . ?
C9 H9 0.9800 . ?
C9 C4 1.610(3) . ?
C9 C8 1.446(3) . ?
C19 C20 1.356(3) . ?
C4 H4 0.9800 . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C20 H20 0.9300 . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.364(3) . ?
F1 C13 1.358(2) . ?
C13 C12 1.357(3) . ?
C12 H12 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
O1 C2 C1 108.21(13) . . ?
O1 C2 C16 106.64(13) . . ?
O1 C2 C3 108.50(14) . . ?
C16 C2 C1 111.82(13) . . ?
C3 C2 C1 109.02(13) . . ?
C3 C2 C16 112.49(13) . . ?
C2 O1 H1 108.6(18) . . ?
C10 C1 C2 110.78(13) . . ?
C10 C1 C6 113.74(15) . . ?
C10 C1 C7 113.78(15) . . ?
C6 C1 C2 110.61(14) . . ?
C6 C1 C7 100.08(14) . . ?
C7 C1 C2 107.25(13) . . ?
C17 C16 C2 121.31(14) . . ?
C21 C16 C2 121.31(16) . . ?
C21 C16 C17 117.37(16) . . ?
C15 C10 C1 120.92(17) . . ?
C11 C10 C1 121.46(16) . . ?
C11 C10 C15 117.55(19) . . ?
C2 C3 H3 115.9 . . ?
C9 C3 C2 115.50(15) . . ?
C9 C3 H3 115.9 . . ?
C4 C3 C2 118.87(15) . . ?
C4 C3 H3 115.9 . . ?
C4 C3 C9 65.06(12) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 121.92(16) . . ?
C18 C17 H17 119.0 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.31(17) . . ?
C5 C6 H6 119.3 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.98(19) . . ?
C20 C21 H21 119.5 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.17(17) . . ?
C4 C5 H5 119.4 . . ?
C17 C18 H18 120.9 . . ?
C19 C18 C17 118.18(18) . . ?
C19 C18 H18 120.9 . . ?
C1 C7 H7 119.8 . . ?
C8 C7 C1 120.35(17) . . ?
C8 C7 H7 119.8 . . ?
C3 C9 H9 116.6 . . ?
C3 C9 C4 57.31(11) . . ?
C4 C9 H9 116.6 . . ?
C8 C9 C3 118.52(18) . . ?
C8 C9 H9 116.6 . . ?
C8 C9 C4 118.06(16) . . ?
C18 C19 F2 118.2(2) . . ?
C18 C19 C20 122.40(18) . . ?
C20 C19 F2 119.38(18) . . ?
C3 C4 C9 57.62(11) . . ?
C3 C4 H4 116.4 . . ?
C5 C4 C3 118.90(17) . . ?
C5 C4 C9 118.46(16) . . ?
C5 C4 H4 116.4 . . ?
C9 C4 H4 116.4 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 119.1 . . ?
C21 C20 H20 120.4 . . ?
C19 C20 C21 119.15(18) . . ?
C19 C20 H20 120.4 . . ?
C7 C8 C9 121.92(17) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C15 C14 H14 120.9 . . ?
C13 C14 C15 118.3(2) . . ?
C13 C14 H14 120.9 . . ?
F1 C13 C14 118.4(2) . . ?
C12 C13 C14 122.8(2) . . ?
C12 C13 F1 118.9(2) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.4(2) . . ?
C13 C12 H12 120.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d_18srv108
_database_code_depnum_ccdc_archive 'CCDC 1857579'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)9-(4-anisyl)-1-(4-Fluorophenyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C22 H19 F O2'
_chemical_formula_sum            'C22 H19 F O2'
_chemical_formula_weight         334.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.8480(7)
_cell_length_b                   7.4991(3)
_cell_length_c                   12.2152(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.6909(15)
_cell_angle_gamma                90
_cell_volume                     1644.88(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.23
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;    
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0975 before and 0.0423 after correction. 
The Ratio of minimum to maximum transmission is 0.9594. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.268
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3800
_reflns_number_total             4798
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1068
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.50096(4) 0.83292(9) 0.06386(6) 0.02327(16) Uani 1 1 d . . . . .
O1 O 0.71729(4) 0.70198(10) 0.57554(7) 0.01805(17) Uani 1 1 d . . . . .
O2 O 0.98099(5) 0.77660(14) 0.37282(9) 0.0319(2) Uani 1 1 d . . . . .
C1 C 0.68375(5) 1.00263(13) 0.50881(9) 0.01387(19) Uani 1 1 d . . . . .
C2 C 0.63812(6) 1.07206(14) 0.58290(9) 0.0161(2) Uani 1 1 d . . . . .
C3 C 0.65519(6) 1.01403(14) 0.70244(9) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.72182(7) 0.94658(15) 0.75900(10) 0.0200(2) Uani 1 1 d . . . . .
C5 C 0.78097(6) 0.94412(15) 0.69826(9) 0.0178(2) Uani 1 1 d . . . . .
C6 C 0.80517(6) 1.13595(16) 0.70303(10) 0.0208(2) Uani 1 1 d . . . . .
C7 C 0.76226(6) 1.25393(15) 0.63121(10) 0.0202(2) Uani 1 1 d . . . . .
C8 C 0.69404(6) 1.19593(14) 0.54339(10) 0.0170(2) Uani 1 1 d . . . . .
C9 C 0.74715(6) 0.87740(13) 0.57265(9) 0.0141(2) Uani 1 1 d . . . . .
C10 C 0.80842(5) 0.85784(14) 0.51618(9) 0.0150(2) Uani 1 1 d . . . . .
C11 C 0.84896(6) 0.69847(15) 0.52957(10) 0.0193(2) Uani 1 1 d . . . . .
C12 C 0.90633(6) 0.67585(16) 0.48194(11) 0.0234(2) Uani 1 1 d . . . . .
C13 C 0.92500(6) 0.81268(17) 0.41932(10) 0.0213(2) Uani 1 1 d . . . . .
C14 C 0.88674(6) 0.97291(17) 0.40665(10) 0.0210(2) Uani 1 1 d . . . . .
C15 C 0.82907(6) 0.99412(15) 0.45522(10) 0.0182(2) Uani 1 1 d . . . . .
C16 C 1.00055(8) 0.9151(2) 0.30696(12) 0.0345(3) Uani 1 1 d . . . . .
C17 C 0.63844(5) 0.95528(14) 0.38819(9) 0.0142(2) Uani 1 1 d . . . . .
C18 C 0.64926(6) 1.03528(14) 0.29148(9) 0.0150(2) Uani 1 1 d . . . . .
C19 C 0.60324(6) 0.99448(14) 0.18150(9) 0.0160(2) Uani 1 1 d . . . . .
C20 C 0.54684(6) 0.87285(14) 0.17088(9) 0.0161(2) Uani 1 1 d . . . . .
C21 C 0.53398(6) 0.78978(15) 0.26342(10) 0.0177(2) Uani 1 1 d . . . . .
C22 C 0.58035(6) 0.83233(14) 0.37231(9) 0.0170(2) Uani 1 1 d . . . . .
H1 H 0.6925(11) 0.712(3) 0.6227(16) 0.051(5) Uiso 1 1 d . . . . .
H2 H 0.5861(8) 1.097(2) 0.5426(12) 0.022(3) Uiso 1 1 d . . . . .
H3 H 0.6156(8) 1.0284(19) 0.7373(12) 0.022(3) Uiso 1 1 d . . . . .
H4 H 0.7350(8) 0.908(2) 0.8378(13) 0.024(4) Uiso 1 1 d . . . . .
H5 H 0.8241(8) 0.868(2) 0.7380(12) 0.022(3) Uiso 1 1 d . . . . .
H6 H 0.8501(9) 1.172(2) 0.7650(13) 0.031(4) Uiso 1 1 d . . . . .
H7 H 0.7726(8) 1.380(2) 0.6372(12) 0.026(4) Uiso 1 1 d . . . . .
H8 H 0.6698(7) 1.2815(19) 0.4862(12) 0.017(3) Uiso 1 1 d . . . . .
H11 H 0.8355(8) 0.604(2) 0.5716(12) 0.023(3) Uiso 1 1 d . . . . .
H12 H 0.9334(9) 0.566(2) 0.4920(14) 0.039(4) Uiso 1 1 d . . . . .
H14 H 0.9004(8) 1.071(2) 0.3651(13) 0.029(4) Uiso 1 1 d . . . . .
H15 H 0.8045(8) 1.107(2) 0.4466(12) 0.023(3) Uiso 1 1 d . . . . .
H16A H 1.0405(10) 0.860(3) 0.2799(15) 0.047(5) Uiso 1 1 d . . . . .
H16B H 1.0205(9) 1.022(2) 0.3550(14) 0.033(4) Uiso 1 1 d . . . . .
H16C H 0.9574(9) 0.951(2) 0.2417(15) 0.037(4) Uiso 1 1 d . . . . .
H18 H 0.6875(7) 1.1210(18) 0.2989(11) 0.016(3) Uiso 1 1 d . . . . .
H19 H 0.6100(8) 1.0534(19) 0.1147(12) 0.023(3) Uiso 1 1 d . . . . .
H21 H 0.4932(8) 0.7040(19) 0.2530(12) 0.023(3) Uiso 1 1 d . . . . .
H22 H 0.5713(7) 0.7759(19) 0.4392(12) 0.019(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C20 1.3636(12) . ?
O1 C9 1.4355(12) . ?
O1 H1 0.85(2) . ?
O2 C13 1.3689(13) . ?
O2 C16 1.4289(19) . ?
C1 C2 1.5175(14) . ?
C1 C8 1.5058(15) . ?
C1 C9 1.5335(14) . ?
C1 C17 1.5038(14) . ?
C2 C3 1.4627(15) . ?
C2 C8 1.5863(15) . ?
C2 H2 0.972(14) . ?
C3 C4 1.3353(16) . ?
C3 H3 0.971(14) . ?
C4 C5 1.5155(16) . ?
C4 H4 0.962(14) . ?
C5 C6 1.5050(16) . ?
C5 C9 1.5545(15) . ?
C5 H5 0.994(14) . ?
C6 C7 1.3324(17) . ?
C6 H6 0.987(16) . ?
C7 C8 1.4679(16) . ?
C7 H7 0.965(16) . ?
C8 H8 0.957(14) . ?
C9 C10 1.5216(14) . ?
C10 C11 1.4010(15) . ?
C10 C15 1.3880(15) . ?
C11 C12 1.3852(16) . ?
C11 H11 0.956(15) . ?
C12 C13 1.3876(18) . ?
C12 H12 0.954(18) . ?
C13 C14 1.3856(17) . ?
C14 C15 1.3967(15) . ?
C14 H14 0.970(16) . ?
C15 H15 0.956(15) . ?
C16 H16A 1.001(18) . ?
C16 H16B 0.996(16) . ?
C16 H16C 0.988(17) . ?
C17 C18 1.3941(14) . ?
C17 C22 1.3990(14) . ?
C18 C19 1.3938(15) . ?
C18 H18 0.949(14) . ?
C19 C20 1.3766(15) . ?
C19 H19 0.970(14) . ?
C20 C21 1.3752(15) . ?
C21 C22 1.3886(15) . ?
C21 H21 0.981(15) . ?
C22 H22 0.981(14) . ?

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
C9 O1 H1 103.8(13) . . ?
C13 O2 C16 116.95(11) . . ?
C2 C1 C9 113.71(9) . . ?
C8 C1 C2 63.29(7) . . ?
C8 C1 C9 115.64(9) . . ?
C17 C1 C2 114.16(8) . . ?
C17 C1 C8 119.25(9) . . ?
C17 C1 C9 118.45(9) . . ?
C1 C2 C8 57.99(7) . . ?
C1 C2 H2 115.5(8) . . ?
C3 C2 C1 120.05(9) . . ?
C3 C2 C8 120.87(9) . . ?
C3 C2 H2 116.4(8) . . ?
C8 C2 H2 113.4(8) . . ?
C2 C3 H3 116.1(8) . . ?
C4 C3 C2 121.08(10) . . ?
C4 C3 H3 122.9(8) . . ?
C3 C4 C5 117.87(10) . . ?
C3 C4 H4 123.1(8) . . ?
C5 C4 H4 118.8(8) . . ?
C4 C5 C9 110.19(9) . . ?
C4 C5 H5 112.5(8) . . ?
C6 C5 C4 103.23(9) . . ?
C6 C5 C9 111.99(9) . . ?
C6 C5 H5 109.9(8) . . ?
C9 C5 H5 109.0(8) . . ?
C5 C6 H6 118.3(9) . . ?
C7 C6 C5 119.54(10) . . ?
C7 C6 H6 121.9(9) . . ?
C6 C7 C8 120.40(10) . . ?
C6 C7 H7 122.3(9) . . ?
C8 C7 H7 117.2(9) . . ?
C1 C8 C2 58.71(7) . . ?
C1 C8 H8 116.7(8) . . ?
C2 C8 H8 113.7(8) . . ?
C7 C8 C1 119.99(9) . . ?
C7 C8 C2 117.82(9) . . ?
C7 C8 H8 116.9(8) . . ?
O1 C9 C1 108.85(8) . . ?
O1 C9 C5 108.48(8) . . ?
O1 C9 C10 106.26(8) . . ?
C1 C9 C5 109.10(8) . . ?
C10 C9 C1 114.21(8) . . ?
C10 C9 C5 109.78(8) . . ?
C11 C10 C9 119.44(9) . . ?
C15 C10 C9 123.19(9) . . ?
C15 C10 C11 117.31(10) . . ?
C10 C11 H11 118.3(9) . . ?
C12 C11 C10 121.54(11) . . ?
C12 C11 H11 120.2(9) . . ?
C11 C12 C13 120.14(11) . . ?
C11 C12 H12 120.4(10) . . ?
C13 C12 H12 119.5(10) . . ?
O2 C13 C12 116.06(11) . . ?
O2 C13 C14 124.45(11) . . ?
C14 C13 C12 119.49(10) . . ?
C13 C14 C15 119.81(11) . . ?
C13 C14 H14 120.2(9) . . ?
C15 C14 H14 120.0(9) . . ?
C10 C15 C14 121.69(10) . . ?
C10 C15 H15 120.5(9) . . ?
C14 C15 H15 117.8(9) . . ?
O2 C16 H16A 103.6(11) . . ?
O2 C16 H16B 111.6(9) . . ?
O2 C16 H16C 111.4(10) . . ?
H16A C16 H16B 109.9(14) . . ?
H16A C16 H16C 111.3(14) . . ?
H16B C16 H16C 109.0(13) . . ?
C18 C17 C1 122.88(9) . . ?
C18 C17 C22 118.42(10) . . ?
C22 C17 C1 118.62(9) . . ?
C17 C18 H18 120.8(8) . . ?
C19 C18 C17 120.93(10) . . ?
C19 C18 H18 118.2(8) . . ?
C18 C19 H19 120.6(9) . . ?
C20 C19 C18 118.22(10) . . ?
C20 C19 H19 121.2(8) . . ?
F1 C20 C19 118.85(9) . . ?
F1 C20 C21 118.02(9) . . ?
C21 C20 C19 123.13(10) . . ?
C20 C21 C22 117.81(10) . . ?
C20 C21 H21 121.2(8) . . ?
C22 C21 H21 121.0(8) . . ?
C17 C22 H22 119.8(8) . . ?
C21 C22 C17 121.49(10) . . ?
C21 C22 H22 118.7(8) . . ?

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
C1 C2 C3 C4 20.55(16) . . . . ?
C1 C2 C8 C7 -109.92(11) . . . . ?
C1 C8 C2 C1 0.000(0) . . . . ?
C1 C8 C2 C3 108.32(11) . . . . ?
C1 C9 C5 C4 59.74(11) . . . . ?
C1 C9 C5 C6 -54.56(11) . . . . ?
C1 C9 C10 C11 -150.78(10) . . . . ?
C1 C9 C10 C15 32.19(14) . . . . ?
C2 C1 C8 C7 106.25(11) . . . . ?
C2 C1 C9 O1 81.53(10) . . . . ?
C2 C1 C9 C5 -36.67(11) . . . . ?
C2 C1 C9 C10 -159.92(9) . . . . ?
C2 C1 C17 C18 120.68(11) . . . . ?
C2 C1 C17 C22 -55.93(12) . . . . ?
C2 C3 C4 C5 4.24(16) . . . . ?
C2 C8 C1 C2 0.000(0) . . . . ?
C2 C8 C1 C9 -104.94(10) . . . . ?
C2 C8 C1 C17 104.08(10) . . . . ?
C3 C2 C1 C8 -109.72(11) . . . . ?
C3 C2 C1 C9 -1.77(14) . . . . ?
C3 C2 C1 C17 138.33(10) . . . . ?
C3 C2 C8 C7 -1.60(15) . . . . ?
C3 C4 C5 C6 75.00(12) . . . . ?
C3 C4 C5 C9 -44.75(13) . . . . ?
C4 C3 C2 C8 -47.89(15) . . . . ?
C4 C5 C6 C7 -77.16(13) . . . . ?
C4 C5 C9 O1 -58.70(11) . . . . ?
C4 C5 C9 C10 -174.41(9) . . . . ?
C5 C6 C7 C8 -3.60(17) . . . . ?
C5 C9 C1 C8 33.83(12) . . . . ?
C5 C9 C1 C17 -174.94(9) . . . . ?
C5 C9 C10 C11 86.33(11) . . . . ?
C5 C9 C10 C15 -90.70(12) . . . . ?
C6 C5 C9 O1 -173.00(8) . . . . ?
C6 C5 C9 C10 71.29(11) . . . . ?
C7 C6 C5 C9 41.35(14) . . . . ?
C7 C8 C1 C9 1.31(14) . . . . ?
C7 C8 C1 C17 -149.67(10) . . . . ?
C8 C1 C9 O1 152.04(9) . . . . ?
C8 C1 C9 C10 -89.42(11) . . . . ?
C8 C1 C17 C18 48.94(14) . . . . ?
C8 C1 C17 C22 -127.67(11) . . . . ?
C8 C2 C1 C8 0.000(0) . . . . ?
C8 C2 C1 C9 107.95(10) . . . . ?
C8 C2 C1 C17 -111.95(10) . . . . ?
C9 C1 C17 C18 -101.23(12) . . . . ?
C9 C1 C17 C22 82.16(12) . . . . ?
C10 C9 C1 C17 61.81(12) . . . . ?
C11 C10 C9 O1 -30.78(12) . . . . ?
C12 C13 O2 C16 179.36(11) . . . . ?
C14 C13 O2 C16 -0.04(17) . . . . ?
C15 C10 C9 O1 152.19(10) . . . . ?
C17 C1 C9 O1 -56.74(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1b_17srv108
_database_code_depnum_ccdc_archive 'CCDC 1857577'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;

_audit_creation_date             2017-03-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5332)
;
_shelx_SHELXL_version_number     2014/7

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-fluorophenyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C21 H16 F2 O'
_chemical_formula_sum            'C21 H16 F2 O'
_chemical_formula_weight         322.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H16 F2 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.7695(8)
_cell_length_b                   6.1770(5)
_cell_length_c                   24.650(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.360(7)
_cell_angle_gamma                90
_cell_volume                     1487.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1991
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.4520
_cell_measurement_theta_min      3.2190
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12156
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0756
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega    5.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00   59.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00   35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.4900    0.0000  -30.0000 126

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  120.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0327492000
_diffrn_orient_matrix_UB_12      -0.0282171000
_diffrn_orient_matrix_UB_13      0.0247591000
_diffrn_orient_matrix_UB_21      0.0645865000
_diffrn_orient_matrix_UB_22      0.0061493000
_diffrn_orient_matrix_UB_23      -0.0128894000
_diffrn_orient_matrix_UB_31      0.0047492000
_diffrn_orient_matrix_UB_32      0.1111402000
_diffrn_orient_matrix_UB_33      0.0070476000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2161
_reflns_number_total             3394
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0541
_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     
'w=1/[σ²(Fo²)+(0.0300P)²+0.0250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.69789(14) 0.3654(2) 0.32532(6) 0.0387(4) Uani 1 1 d . . . . .
F2 F 0.88702(13) 0.0431(2) 0.05984(6) 0.0361(4) Uani 1 1 d . . . . .
O1 O 0.43725(16) 0.7242(2) 0.11052(7) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.3223(2) 0.4099(3) 0.15055(9) 0.0186(5) Uani 1 1 d . . . . .
C2 C 0.3987(2) 0.5046(3) 0.09914(9) 0.0183(5) Uani 1 1 d . . . . .
C3 C 0.3011(2) 0.5033(3) 0.05100(10) 0.0199(5) Uani 1 1 d . . . . .
C4 C 0.1942(2) 0.3300(3) 0.04766(10) 0.0212(5) Uani 1 1 d . . . . .
C5 C 0.1905(2) 0.1649(3) 0.09006(10) 0.0233(5) Uani 1 1 d . . . . .
C6 C 0.2547(2) 0.1948(3) 0.13730(10) 0.0201(5) Uani 1 1 d . . . . .
C7 C 0.1979(2) 0.5524(3) 0.16109(10) 0.0213(5) Uani 1 1 d . . . . .
C8 C 0.1212(2) 0.6213(3) 0.11945(10) 0.0220(5) Uani 1 1 d . . . . .
C9 C 0.1566(2) 0.5729(3) 0.06326(10) 0.0223(5) Uani 1 1 d . . . . .
C10 C 0.4198(2) 0.3962(3) 0.19881(9) 0.0203(5) Uani 1 1 d . . . . .
C11 C 0.4997(2) 0.2110(4) 0.20725(10) 0.0224(5) Uani 1 1 d . . . . .
C12 C 0.5929(2) 0.1991(4) 0.24973(10) 0.0265(6) Uani 1 1 d . . . . .
C13 C 0.6062(2) 0.3761(4) 0.28331(10) 0.0278(6) Uani 1 1 d . . . . .
C14 C 0.5317(2) 0.5629(4) 0.27652(10) 0.0280(6) Uani 1 1 d . . . . .
C15 C 0.4390(2) 0.5699(4) 0.23370(10) 0.0247(5) Uani 1 1 d . . . . .
C16 C 0.5306(2) 0.3839(3) 0.08750(9) 0.0169(5) Uani 1 1 d . . . . .
C17 C 0.6573(2) 0.4698(4) 0.10229(10) 0.0229(5) Uani 1 1 d . . . . .
C18 C 0.7775(2) 0.3568(4) 0.09319(10) 0.0257(5) Uani 1 1 d . . . . .
C19 C 0.7691(2) 0.1560(4) 0.06916(9) 0.0236(5) Uani 1 1 d . . . . .
C20 C 0.6468(2) 0.0635(4) 0.05429(9) 0.0215(5) Uani 1 1 d . . . . .
C21 C 0.5282(2) 0.1802(3) 0.06306(9) 0.0198(5) Uani 1 1 d . . . . .
H1 H 0.358(3) 0.798(4) 0.1140(12) 0.061(10) Uiso 1 1 d . . . . .
H3 H 0.340(2) 0.554(3) 0.0204(9) 0.021(6) Uiso 1 1 d . . . . .
H4 H 0.165(2) 0.291(3) 0.0117(10) 0.026(6) Uiso 1 1 d . . . . .
H5 H 0.133(2) 0.035(3) 0.0828(9) 0.022(6) Uiso 1 1 d . . . . .
H6 H 0.248(2) 0.087(3) 0.1669(10) 0.030(7) Uiso 1 1 d . . . . .
H7 H 0.173(2) 0.578(3) 0.1992(10) 0.022(6) Uiso 1 1 d . . . . .
H8 H 0.036(2) 0.702(3) 0.1265(9) 0.021(6) Uiso 1 1 d . . . . .
H9 H 0.107(2) 0.642(3) 0.0345(9) 0.016(6) Uiso 1 1 d . . . . .
H11 H 0.490(2) 0.087(3) 0.1836(9) 0.026(6) Uiso 1 1 d . . . . .
H12 H 0.652(2) 0.069(4) 0.2565(10) 0.042(7) Uiso 1 1 d . . . . .
H14 H 0.545(2) 0.686(4) 0.3016(10) 0.035(7) Uiso 1 1 d . . . . .
H15 H 0.387(2) 0.697(3) 0.2288(9) 0.025(6) Uiso 1 1 d . . . . .
H17 H 0.661(2) 0.612(3) 0.1200(9) 0.025(6) Uiso 1 1 d . . . . .
H18 H 0.864(2) 0.421(3) 0.1015(9) 0.029(6) Uiso 1 1 d . . . . .
H21 H 0.440(2) 0.117(3) 0.0529(9) 0.027(6) Uiso 1 1 d . . . . .
H20 H 0.644(2) -0.076(4) 0.0368(10) 0.036(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.366(2) . ?
F2 C19 1.367(2) . ?
O1 C2 1.435(2) . ?
O1 H1 0.90(3) . ?
C1 C2 1.587(3) . ?
C1 C6 1.518(3) . ?
C1 C7 1.524(3) . ?
C1 C10 1.522(3) . ?
C2 C3 1.518(3) . ?
C2 C16 1.517(3) . ?
C3 C4 1.497(3) . ?
C3 C9 1.508(3) . ?
C3 H3 0.90(2) . ?
C4 C5 1.461(3) . ?
C4 C9 1.592(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.332(3) . ?
C5 H5 1.00(2) . ?
C6 H6 0.99(2) . ?
C7 C8 1.337(3) . ?
C7 H7 0.98(2) . ?
C8 C9 1.461(3) . ?
C8 H8 0.98(2) . ?
C9 H9 0.957(19) . ?
C10 C11 1.399(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.97(2) . ?
C12 C13 1.377(3) . ?
C12 H12 1.00(2) . ?
C13 C14 1.374(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.99(2) . ?
C15 H15 0.94(2) . ?
C16 C17 1.394(3) . ?
C16 C21 1.395(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.98(2) . ?
C18 C19 1.376(3) . ?
C18 H18 0.95(2) . ?
C19 C20 1.372(3) . ?
C20 C21 1.383(3) . ?
C20 H20 0.96(2) . ?
C21 H21 0.98(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 105.6(18) . . ?
C6 C1 C2 110.93(18) . . ?
C6 C1 C7 101.30(16) . . ?
C6 C1 C10 112.87(18) . . ?
C7 C1 C2 107.64(17) . . ?
C10 C1 C2 110.44(17) . . ?
C10 C1 C7 113.25(19) . . ?
O1 C2 C1 108.46(17) . . ?
O1 C2 C3 108.71(16) . . ?
O1 C2 C16 106.24(16) . . ?
C3 C2 C1 109.01(17) . . ?
C16 C2 C1 111.97(17) . . ?
C16 C2 C3 112.31(19) . . ?
C2 C3 H3 112.7(13) . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 C9 63.99(15) . . ?
C4 C3 H3 119.8(14) . . ?
C9 C3 C2 115.2(2) . . ?
C9 C3 H3 118.0(13) . . ?
C3 C4 C9 58.35(14) . . ?
C3 C4 H4 115.7(14) . . ?
C5 C4 C3 118.70(19) . . ?
C5 C4 C9 118.6(2) . . ?
C5 C4 H4 118.5(13) . . ?
C9 C4 H4 113.0(13) . . ?
C4 C5 H5 116.9(12) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 122.0(12) . . ?
C1 C6 H6 117.6(13) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 121.0(12) . . ?
C1 C7 H7 117.2(12) . . ?
C8 C7 C1 119.8(2) . . ?
C8 C7 H7 122.7(12) . . ?
C7 C8 C9 121.9(2) . . ?
C7 C8 H8 119.6(13) . . ?
C9 C8 H8 118.5(13) . . ?
C3 C9 C4 57.66(14) . . ?
C3 C9 H9 116.8(13) . . ?
C4 C9 H9 111.1(12) . . ?
C8 C9 C3 118.4(2) . . ?
C8 C9 C4 118.6(2) . . ?
C8 C9 H9 119.2(13) . . ?
C11 C10 C1 120.5(2) . . ?
C15 C10 C1 121.53(19) . . ?
C15 C10 C11 117.9(2) . . ?
C10 C11 H11 120.2(13) . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 118.5(12) . . ?
C11 C12 H12 122.8(14) . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 H12 119.0(14) . . ?
F1 C13 C12 118.4(2) . . ?
F1 C13 C14 118.5(2) . . ?
C14 C13 C12 123.1(2) . . ?
C13 C14 C15 117.5(2) . . ?
C13 C14 H14 120.2(13) . . ?
C15 C14 H14 122.3(13) . . ?
C10 C15 C14 122.2(2) . . ?
C10 C15 H15 119.7(13) . . ?
C14 C15 H15 118.2(13) . . ?
C17 C16 C2 121.15(19) . . ?
C17 C16 C21 117.9(2) . . ?
C21 C16 C2 120.89(18) . . ?
C16 C17 H17 119.3(12) . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.5(12) . . ?
C17 C18 H18 120.4(13) . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 H18 121.1(13) . . ?
F2 C19 C18 119.0(2) . . ?
F2 C19 C20 118.4(2) . . ?
C20 C19 C18 122.6(2) . . ?
C19 C20 C21 118.0(2) . . ?
C19 C20 H20 121.2(14) . . ?
C21 C20 H20 120.7(14) . . ?
C16 C21 H21 118.9(13) . . ?
C20 C21 C16 121.8(2) . . ?
C20 C21 H21 119.3(13) . . ?

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 C1 C10 C7 120.8(2) . . . . ?
C5 C2 C1 C6 17.54(12) . . . . ?
C5 C2 C1 C10 143.46(18) . . . . ?
C5 C2 C1 C12 123.77(11) . . . . ?
C6 C1 C2 F1 -125.63(17) . . . . ?
C6 C1 C2 C4 35.33(15) . . . . ?
C6 C1 C10 C7 -114.4(3) . . . . ?
C10 C1 C2 F1 0.29(11) . . . . ?
C10 C1 C2 C4 161.25(15) . . . . ?
C12 C1 C2 F1 -19.40(5) . . . . ?
C12 C1 C2 C4 141.56(9) . . . . ?
C12 C1 C10 C7 -153.2(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3 0 -5 0.0306 -3.0000 0.0001 -5.0000 -0.2220 -0.1293 -0.0495
3 0 5 0.0306 3.0000 -0.0001 5.0000 0.2220 0.1293 0.0495
1 3 -5 0.1410 1.0000 3.0000 -4.9996 -0.1757 0.1475 0.3029
-1 -3 5 0.1410 -1.0000 -3.0000 4.9996 0.1757 -0.1475 -0.3029
-1 0 5 0.0741 -1.0000 -0.0000 5.0000 0.0910 -0.1290 0.0305
0 -1 -5 0.0725 -0.0000 -1.0000 -5.0001 -0.0956 0.0583 -0.1464
0 3 5 0.1303 0.0001 2.9999 5.0004 0.0392 -0.0460 0.3687

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1e_18srv274
_database_code_depnum_ccdc_archive 'CCDC 1857580'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2018-06-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1


_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)9-(4-Fluorophenyl)-1-phenyltricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C21 H17 F O'
_chemical_formula_sum            'C21 H17 F O'
_chemical_formula_weight         304.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.7901(6)
_cell_length_b                   6.2016(4)
_cell_length_c                   24.0401(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.931(2)
_cell_angle_gamma                90
_cell_volume                     1457.67(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5033
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;    
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1358 before and 0.0530 after correction. 
The Ratio of minimum to maximum transmission is 0.8948. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26251
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         2.209
_diffrn_ambient_temperature      130.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2638
_reflns_number_total             3888
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker AXS, 2016)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.031
_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)+(0.0400P)²+0.4900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.38963(8) 0.04977(17) 0.43908(4) 0.0335(3) Uani 1 1 d . . . . .
O1 O 0.05510(11) 0.72321(17) 0.38730(4) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.19440(14) 0.5014(2) 0.44834(6) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.30115(14) 0.3280(2) 0.45233(7) 0.0201(3) Uani 1 1 d . . . . .
C3 C 0.30186(14) 0.1660(2) 0.40850(7) 0.0213(3) Uani 1 1 d . . . . .
C4 C 0.23594(14) 0.1975(2) 0.35934(6) 0.0193(3) Uani 1 1 d . . . . .
C5 C 0.16740(14) 0.4124(2) 0.34591(6) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.29066(14) 0.5541(2) 0.33690(6) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.36969(15) 0.6220(2) 0.38017(7) 0.0211(3) Uani 1 1 d . . . . .
C8 C 0.33792(15) 0.5706(2) 0.43751(6) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.09441(14) 0.5045(2) 0.39825(6) 0.0158(3) Uani 1 1 d . . . . .
C10 C -0.03620(14) 0.3835(2) 0.40951(6) 0.0155(3) Uani 1 1 d . . . . .
C11 C -0.03147(14) 0.1804(2) 0.43401(6) 0.0171(3) Uani 1 1 d . . . . .
C12 C -0.14966(14) 0.0661(3) 0.44342(6) 0.0196(3) Uani 1 1 d . . . . .
C13 C -0.27278(14) 0.1609(3) 0.42898(6) 0.0214(3) Uani 1 1 d . . . . .
C14 C -0.28364(15) 0.3610(3) 0.40500(6) 0.0228(3) Uani 1 1 d . . . . .
C15 C -0.16389(15) 0.4718(3) 0.39488(6) 0.0193(3) Uani 1 1 d . . . . .
C16 C 0.06693(14) 0.4029(2) 0.29559(6) 0.0191(3) Uani 1 1 d . . . . .
C17 C -0.01171(15) 0.2193(3) 0.28425(6) 0.0220(3) Uani 1 1 d . . . . .
C18 C -0.10665(16) 0.2142(3) 0.23913(6) 0.0259(4) Uani 1 1 d . . . . .
C19 C -0.12442(17) 0.3934(3) 0.20504(7) 0.0281(4) Uani 1 1 d . . . . .
C20 C -0.04697(17) 0.5760(3) 0.21589(7) 0.0287(4) Uani 1 1 d . . . . .
C21 C 0.04775(16) 0.5807(3) 0.26084(6) 0.0235(3) Uani 1 1 d . . . . .
H1 H 0.131(2) 0.791(3) 0.3838(8) 0.046(6) Uiso 1 1 d . . . . .
H1A H 0.1576(14) 0.549(2) 0.4830(6) 0.012(4) Uiso 1 1 d . . . . .
H2 H 0.3345(15) 0.290(3) 0.4893(7) 0.020(4) Uiso 1 1 d . . . . .
H3 H 0.3532(15) 0.039(3) 0.4163(6) 0.022(4) Uiso 1 1 d . . . . .
H4 H 0.2406(16) 0.091(3) 0.3308(7) 0.024(4) Uiso 1 1 d . . . . .
H6 H 0.3186(15) 0.578(2) 0.2981(6) 0.017(4) Uiso 1 1 d . . . . .
H7 H 0.4535(16) 0.703(3) 0.3744(6) 0.020(4) Uiso 1 1 d . . . . .
H8 H 0.3898(15) 0.644(3) 0.4678(7) 0.021(4) Uiso 1 1 d . . . . .
H15 H -0.1687(16) 0.614(3) 0.3773(7) 0.026(4) Uiso 1 1 d . . . . .
H11 H 0.0563(15) 0.117(2) 0.4439(6) 0.016(4) Uiso 1 1 d . . . . .
H12 H -0.1459(16) -0.080(3) 0.4589(7) 0.024(4) Uiso 1 1 d . . . . .
H14 H -0.3724(17) 0.424(3) 0.3957(7) 0.029(5) Uiso 1 1 d . . . . .
H17 H 0.0000(16) 0.091(3) 0.3083(7) 0.024(4) Uiso 1 1 d . . . . .
H18 H -0.1616(17) 0.082(3) 0.2321(7) 0.033(5) Uiso 1 1 d . . . . .
H19 H -0.1955(15) 0.390(2) 0.1720(6) 0.015(4) Uiso 1 1 d . . . . .
H20 H -0.0604(18) 0.704(3) 0.1918(7) 0.036(5) Uiso 1 1 d . . . . .
H21 H 0.0996(16) 0.711(3) 0.2678(6) 0.021(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.3678(16) . ?
O1 C9 1.4307(17) . ?
O1 H1 0.87(2) . ?
C1 C2 1.499(2) . ?
C1 C8 1.5046(19) . ?
C1 C9 1.513(2) . ?
C1 H1A 0.971(15) . ?
C2 C3 1.456(2) . ?
C2 C8 1.591(2) . ?
C2 H2 0.961(16) . ?
C3 C4 1.332(2) . ?
C3 H3 0.947(16) . ?
C4 C5 1.519(2) . ?
C4 H4 0.957(17) . ?
C5 C6 1.518(2) . ?
C5 C9 1.5851(19) . ?
C5 C16 1.521(2) . ?
C6 C7 1.332(2) . ?
C6 H6 0.997(15) . ?
C7 C8 1.464(2) . ?
C7 H7 0.978(16) . ?
C8 H8 0.979(16) . ?
C9 C10 1.5186(19) . ?
C10 C11 1.391(2) . ?
C10 C15 1.393(2) . ?
C11 C12 1.385(2) . ?
C11 H11 0.962(15) . ?
C12 C13 1.370(2) . ?
C12 H12 0.978(17) . ?
C13 C14 1.370(2) . ?
C14 C15 1.391(2) . ?
C14 H14 0.968(17) . ?
C15 H15 0.975(17) . ?
C16 C17 1.393(2) . ?
C16 C21 1.390(2) . ?
C17 C18 1.392(2) . ?
C17 H17 0.986(17) . ?
C18 C19 1.387(2) . ?
C18 H18 0.992(18) . ?
C19 C20 1.380(2) . ?
C19 H19 1.029(15) . ?
C20 C21 1.388(2) . ?
C20 H20 0.986(19) . ?
C21 H21 0.966(17) . ?

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
C9 O1 H1 104.8(14) . . ?
C2 C1 C8 63.98(10) . . ?
C2 C1 C9 118.75(13) . . ?
C2 C1 H1A 116.8(8) . . ?
C8 C1 C9 115.51(12) . . ?
C8 C1 H1A 116.9(8) . . ?
C9 C1 H1A 115.2(8) . . ?
C1 C2 C8 58.18(9) . . ?
C1 C2 H2 116.0(9) . . ?
C3 C2 C1 118.53(13) . . ?
C3 C2 C8 118.73(13) . . ?
C3 C2 H2 119.1(10) . . ?
C8 C2 H2 111.7(10) . . ?
C2 C3 H3 116.8(10) . . ?
C4 C3 C2 121.40(14) . . ?
C4 C3 H3 121.7(10) . . ?
C3 C4 C5 120.39(14) . . ?
C3 C4 H4 119.8(10) . . ?
C5 C4 H4 119.4(10) . . ?
C4 C5 C9 111.07(12) . . ?
C4 C5 C16 113.32(12) . . ?
C6 C5 C4 101.10(11) . . ?
C6 C5 C9 107.37(11) . . ?
C6 C5 C16 113.31(12) . . ?
C16 C5 C9 110.24(11) . . ?
C5 C6 H6 118.6(9) . . ?
C7 C6 C5 120.38(13) . . ?
C7 C6 H6 120.5(9) . . ?
C6 C7 C8 121.58(14) . . ?
C6 C7 H7 120.7(9) . . ?
C8 C7 H7 117.7(9) . . ?
C1 C8 C2 57.83(9) . . ?
C1 C8 H8 117.3(9) . . ?
C2 C8 H8 112.9(10) . . ?
C7 C8 C1 118.06(13) . . ?
C7 C8 C2 118.56(13) . . ?
C7 C8 H8 118.1(9) . . ?
O1 C9 C1 108.40(11) . . ?
O1 C9 C5 108.88(11) . . ?
O1 C9 C10 106.26(11) . . ?
C1 C9 C5 109.13(11) . . ?
C1 C9 C10 111.61(11) . . ?
C10 C9 C5 112.42(11) . . ?
C11 C10 C9 120.86(12) . . ?
C11 C10 C15 118.23(13) . . ?
C15 C10 C9 120.91(13) . . ?
C10 C11 H11 118.9(9) . . ?
C12 C11 C10 121.51(13) . . ?
C12 C11 H11 119.6(9) . . ?
C11 C12 H12 121.3(9) . . ?
C13 C12 C11 118.09(15) . . ?
C13 C12 H12 120.6(9) . . ?
F1 C13 C12 118.17(14) . . ?
F1 C13 C14 118.90(13) . . ?
C12 C13 C14 122.92(14) . . ?
C13 C14 C15 118.24(14) . . ?
C13 C14 H14 120.8(10) . . ?
C15 C14 H14 120.9(10) . . ?
C10 C15 H15 119.1(10) . . ?
C14 C15 C10 120.99(14) . . ?
C14 C15 H15 119.9(10) . . ?
C17 C16 C5 121.04(13) . . ?
C21 C16 C5 120.62(13) . . ?
C21 C16 C17 118.29(14) . . ?
C16 C17 H17 119.9(9) . . ?
C18 C17 C16 120.76(15) . . ?
C18 C17 H17 119.4(9) . . ?
C17 C18 H18 119.1(10) . . ?
C19 C18 C17 120.05(16) . . ?
C19 C18 H18 120.8(10) . . ?
C18 C19 H19 119.8(8) . . ?
C20 C19 C18 119.65(15) . . ?
C20 C19 H19 120.5(8) . . ?
C19 C20 C21 120.20(16) . . ?
C19 C20 H20 119.5(10) . . ?
C21 C20 H20 120.3(11) . . ?
C16 C21 H21 120.5(9) . . ?
C20 C21 C16 121.04(16) . . ?
C20 C21 H21 118.5(9) . . ?

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
C1 C2 C3 C4 17.4(2) . . . . ?
C1 C2 C8 C7 -106.88(15) . . . . ?
C1 C8 C2 C1 0.000(0) . . . . ?
C1 C8 C2 C3 107.51(15) . . . . ?
C1 C8 C7 C6 -18.9(2) . . . . ?
C1 C9 C5 C4 50.64(15) . . . . ?
C1 C9 C5 C6 -59.04(14) . . . . ?
C1 C9 C5 C16 177.10(12) . . . . ?
C1 C9 C10 C11 -47.05(17) . . . . ?
C1 C9 C10 C15 133.85(14) . . . . ?
C2 C1 C8 C7 107.74(15) . . . . ?
C2 C1 C9 O1 -149.93(12) . . . . ?
C2 C1 C9 C5 -31.49(17) . . . . ?
C2 C1 C9 C10 93.37(15) . . . . ?
C2 C3 C4 C5 5.0(2) . . . . ?
C2 C8 C1 C2 0.000(0) . . . . ?
C2 C8 C1 C9 -111.11(14) . . . . ?
C2 C8 C7 C6 47.8(2) . . . . ?
C3 C2 C1 C8 -107.85(15) . . . . ?
C3 C2 C1 C9 -1.66(19) . . . . ?
C3 C2 C8 C7 0.6(2) . . . . ?
C3 C4 C5 C6 73.62(16) . . . . ?
C3 C4 C5 C9 -40.07(18) . . . . ?
C3 C4 C5 C16 -164.80(13) . . . . ?
C4 C3 C2 C8 -49.83(19) . . . . ?
C4 C5 C6 C7 -75.01(16) . . . . ?
C4 C5 C9 O1 168.79(11) . . . . ?
C4 C5 C9 C10 -73.75(15) . . . . ?
C4 C5 C16 C17 34.87(18) . . . . ?
C4 C5 C16 C21 -147.47(13) . . . . ?
C5 C6 C7 C8 -2.6(2) . . . . ?
C5 C9 C1 C8 41.50(16) . . . . ?
C5 C9 C10 C11 75.95(16) . . . . ?
C5 C9 C10 C15 -103.15(15) . . . . ?
C6 C5 C9 O1 59.10(14) . . . . ?
C6 C5 C9 C10 176.57(11) . . . . ?
C6 C5 C16 C17 149.33(13) . . . . ?
C6 C5 C16 C21 -33.01(18) . . . . ?
C7 C6 C5 C9 41.44(17) . . . . ?
C7 C6 C5 C16 163.40(13) . . . . ?
C7 C8 C1 C9 -3.36(19) . . . . ?
C8 C1 C9 O1 -76.94(15) . . . . ?
C8 C1 C9 C10 166.36(12) . . . . ?
C8 C2 C1 C8 0.000(0) . . . . ?
C8 C2 C1 C9 106.19(14) . . . . ?
C9 C5 C16 C17 -90.32(16) . . . . ?
C9 C5 C16 C21 87.34(15) . . . . ?
C10 C9 C5 C16 52.71(15) . . . . ?
C11 C10 C9 O1 -165.04(12) . . . . ?
C15 C10 C9 O1 15.86(17) . . . . ?
C16 C5 C9 O1 -64.75(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1b_270k
_database_code_depnum_ccdc_archive 'CCDC 1857581'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;


_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-fluorophenyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C21 H16 F2 O'
_chemical_formula_sum            'C21 H16 F2 O'
_chemical_formula_weight         322.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H16 F2 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.8084(3)
_cell_length_b                   6.2441(2)
_cell_length_c                   24.8702(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.457(3)
_cell_angle_gamma                90
_cell_volume                     1523.11(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3418
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      31.4230
_cell_measurement_theta_min      2.4600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         3.205
_diffrn_ambient_temperature      270.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029  -57.0000    0.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029 -100.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029 -100.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega   16.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029   38.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029   57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   82.00  111.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029  178.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00  102.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029   57.0000  150.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0362255000
_diffrn_orient_matrix_UB_12      0.0664440000
_diffrn_orient_matrix_UB_13      0.0180628000
_diffrn_orient_matrix_UB_21      0.0607889000
_diffrn_orient_matrix_UB_22      0.0174669000
_diffrn_orient_matrix_UB_23      0.0150102000
_diffrn_orient_matrix_UB_31      0.0148667000
_diffrn_orient_matrix_UB_32      0.0904992000
_diffrn_orient_matrix_UB_33      -0.0161774000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2858
_reflns_number_total             4049
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.241
_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   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.017
_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)+(0.0420P)²+0.3120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C6(H6), C5(H5), C17(H17), C7(H7), C11(H11), C15(H15), C20(H20),
 C8(H8), C18(H18), C14(H14), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43813(12) 0.21936(15) 0.11093(4) 0.0424(3) Uani 1 1 d . . . . .
C2 C 0.39969(13) 0.00248(19) 0.09952(5) 0.0315(3) Uani 1 1 d . . . . .
C1 C 0.32342(14) -0.0918(2) 0.15065(5) 0.0335(3) Uani 1 1 d . . . . .
C16 C 0.53105(13) -0.1178(2) 0.08796(5) 0.0314(3) Uani 1 1 d . . . . .
C3 C 0.30264(14) 0.0021(2) 0.05214(5) 0.0365(3) Uani 1 1 d . . . . .
H3 H 0.340328 0.051426 0.017931 0.044 Uiso 1 1 calc R . . . .
C10 C 0.42075(15) -0.1064(2) 0.19824(5) 0.0372(3) Uani 1 1 d . . . . .
C21 C 0.52883(14) -0.3184(2) 0.06347(5) 0.0360(3) Uani 1 1 d . . . . .
H21 H 0.445620 -0.376713 0.052846 0.043 Uiso 1 1 calc R . . . .
C6 C 0.25499(14) -0.3033(2) 0.13700(6) 0.0385(3) Uani 1 1 d . . . . .
H6 H 0.257144 -0.414401 0.161896 0.046 Uiso 1 1 calc R . . . .
C5 C 0.19213(14) -0.3321(2) 0.09006(6) 0.0422(3) Uani 1 1 d . . . . .
H5 H 0.144723 -0.458725 0.083757 0.051 Uiso 1 1 calc R . . . .
C17 C 0.65719(15) -0.0338(2) 0.10268(6) 0.0423(3) Uani 1 1 d . . . . .
H17 H 0.661545 0.099712 0.119175 0.051 Uiso 1 1 calc R . . . .
C7 C 0.19992(15) 0.0493(2) 0.16055(6) 0.0408(3) Uani 1 1 d . . . . .
H7 H 0.177286 0.087273 0.195525 0.049 Uiso 1 1 calc R . . . .
F2 F 0.88539(10) -0.45511(19) 0.05974(5) 0.0732(3) Uani 1 1 d . . . . .
C11 C 0.43992(16) 0.0659(2) 0.23306(6) 0.0456(4) Uani 1 1 d . . . . .
H11 H 0.389829 0.190635 0.227663 0.055 Uiso 1 1 calc R . . . .
C15 C 0.49830(16) -0.2900(2) 0.20710(6) 0.0430(3) Uani 1 1 d . . . . .
H15 H 0.487657 -0.406630 0.184211 0.052 Uiso 1 1 calc R . . . .
C20 C 0.64712(15) -0.4332(2) 0.05453(6) 0.0417(3) Uani 1 1 d . . . . .
H20 H 0.644052 -0.568254 0.038794 0.050 Uiso 1 1 calc R . . . .
C9 C 0.15916(15) 0.0713(2) 0.06380(6) 0.0415(3) Uani 1 1 d . . . . .
H9 H 0.113217 0.156676 0.035994 0.050 Uiso 1 1 calc R . . . .
C4 C 0.19615(15) -0.1689(2) 0.04833(6) 0.0410(3) Uani 1 1 d . . . . .
H4 H 0.170413 -0.215153 0.011983 0.049 Uiso 1 1 calc R . . . .
C8 C 0.12374(15) 0.1192(2) 0.11953(6) 0.0417(3) Uani 1 1 d . . . . .
H8 H 0.046322 0.200258 0.126512 0.050 Uiso 1 1 calc R . . . .
C19 C 0.76823(15) -0.3433(3) 0.06938(6) 0.0466(4) Uani 1 1 d . . . . .
F1 F 0.69535(12) -0.1396(2) 0.32442(4) 0.0775(3) Uani 1 1 d . . . . .
C18 C 0.77668(16) -0.1460(3) 0.09315(6) 0.0506(4) Uani 1 1 d . . . . .
H18 H 0.860838 -0.088261 0.102731 0.061 Uiso 1 1 calc R . . . .
C14 C 0.59124(17) -0.3025(3) 0.24943(6) 0.0509(4) Uani 1 1 d . . . . .
H14 H 0.642745 -0.425617 0.255112 0.061 Uiso 1 1 calc R . . . .
C13 C 0.60490(17) -0.1282(3) 0.28261(6) 0.0523(4) Uani 1 1 d . . . . .
C12 C 0.53201(18) 0.0557(3) 0.27559(6) 0.0534(4) Uani 1 1 d . . . . .
H12 H 0.543726 0.171327 0.298729 0.064 Uiso 1 1 calc R . . . .
H1 H 0.362(3) 0.295(4) 0.1128(9) 0.100(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.4334(15) . ?
O1 H1 0.89(3) . ?
C2 C1 1.5932(17) . ?
C2 C16 1.5207(18) . ?
C2 C3 1.5089(18) . ?
C1 C10 1.5173(19) . ?
C1 C6 1.5187(18) . ?
C1 C7 1.5197(19) . ?
C16 C21 1.3931(18) . ?
C16 C17 1.3901(19) . ?
C3 H3 0.9800 . ?
C3 C9 1.5027(19) . ?
C3 C4 1.496(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.392(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.3833(19) . ?
C6 H6 0.9300 . ?
C6 C5 1.328(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.455(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.333(2) . ?
F2 C19 1.3675(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.389(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.362(2) . ?
C9 H9 0.9800 . ?
C9 C4 1.591(2) . ?
C9 C8 1.462(2) . ?
C4 H4 0.9800 . ?
C8 H8 0.9300 . ?
C19 C18 1.369(2) . ?
F1 C13 1.3634(18) . ?
C18 H18 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.371(2) . ?
C13 C12 1.363(2) . ?
C12 H12 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
C2 O1 H1 107.2(16) . . ?
O1 C2 C1 108.39(10) . . ?
O1 C2 C16 106.38(11) . . ?
O1 C2 C3 108.63(10) . . ?
C16 C2 C1 111.86(10) . . ?
C3 C2 C1 108.99(10) . . ?
C3 C2 C16 112.44(10) . . ?
C10 C1 C2 110.38(11) . . ?
C10 C1 C6 113.35(11) . . ?
C10 C1 C7 113.94(11) . . ?
C6 C1 C2 110.63(10) . . ?
C6 C1 C7 100.90(11) . . ?
C7 C1 C2 107.16(10) . . ?
C21 C16 C2 121.09(12) . . ?
C17 C16 C2 121.17(12) . . ?
C17 C16 C21 117.72(12) . . ?
C2 C3 H3 115.9 . . ?
C9 C3 C2 115.76(11) . . ?
C9 C3 H3 115.9 . . ?
C4 C3 C2 119.11(11) . . ?
C4 C3 H3 115.9 . . ?
C4 C3 C9 64.10(10) . . ?
C11 C10 C1 121.30(13) . . ?
C15 C10 C1 120.84(12) . . ?
C15 C10 C11 117.81(14) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 C16 121.73(13) . . ?
C20 C21 H21 119.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.03(12) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.14(13) . . ?
C4 C5 H5 119.4 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.06(14) . . ?
C18 C17 H17 119.5 . . ?
C1 C7 H7 119.7 . . ?
C8 C7 C1 120.55(12) . . ?
C8 C7 H7 119.7 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.50(15) . . ?
C12 C11 H11 119.3 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.39(14) . . ?
C14 C15 H15 119.3 . . ?
C21 C20 H20 120.9 . . ?
C19 C20 C21 118.26(14) . . ?
C19 C20 H20 120.9 . . ?
C3 C9 H9 116.5 . . ?
C3 C9 C4 57.74(9) . . ?
C4 C9 H9 116.5 . . ?
C8 C9 C3 118.15(13) . . ?
C8 C9 H9 116.5 . . ?
C8 C9 C4 118.58(12) . . ?
C3 C4 C9 58.16(9) . . ?
C3 C4 H4 116.3 . . ?
C5 C4 C3 118.51(12) . . ?
C5 C4 C9 118.68(12) . . ?
C5 C4 H4 116.3 . . ?
C9 C4 H4 116.3 . . ?
C7 C8 C9 121.49(13) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
F2 C19 C18 119.16(14) . . ?
C20 C19 F2 118.30(14) . . ?
C20 C19 C18 122.54(14) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.67(14) . . ?
C19 C18 H18 120.7 . . ?
C15 C14 H14 120.9 . . ?
C13 C14 C15 118.13(15) . . ?
C13 C14 H14 120.9 . . ?
F1 C13 C14 118.51(15) . . ?
C12 C13 F1 118.62(16) . . ?
C12 C13 C14 122.87(15) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.30(15) . . ?
C13 C12 H12 120.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3b_17srv359
_database_code_depnum_ccdc_archive 'CCDC 1857874'
_audit_update_record             
;
2018-07-24 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-12-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1

_chemical_name_common            ?
_chemical_name_systematic        
;
1-(4-Fluorophenyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-one
;
_chemical_formula_moiety         'C15 H11 F O'
_chemical_formula_sum            'C15 H11 F O'
_chemical_formula_weight         226.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.9209(4)
_cell_length_b                   9.9803(4)
_cell_length_c                   11.1024(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1099.29(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7547
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.15
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0898 before and 0.0396 after correction. The Ratio of minimum to maximum transmission is 0.9450. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17800
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.498
_diffrn_reflns_theta_min         2.744
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2730
_reflns_number_total             3073
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.048
_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)+(0.0470P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0824
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.41599(11) 0.88696(10) 0.33241(10) 0.0256(3) Uani 1 1 d . . . . .
O1 O 0.37254(13) 0.40169(13) 0.66821(12) 0.0230(3) Uani 1 1 d . . . . .
C1 C 0.56691(15) 0.39915(16) 0.54300(14) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.71445(16) 0.36545(17) 0.56833(16) 0.0189(4) Uani 1 1 d . . . . .
C3 C 0.74811(18) 0.29998(18) 0.68336(18) 0.0233(4) Uani 1 1 d . . . . .
C4 C 0.6578(2) 0.22876(19) 0.74344(17) 0.0237(4) Uani 1 1 d . . . . .
C5 C 0.51831(18) 0.21118(17) 0.68846(15) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.53750(18) 0.10947(18) 0.58808(16) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.59569(18) 0.14865(17) 0.48623(16) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.63709(17) 0.28942(17) 0.46900(15) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.47446(17) 0.34419(17) 0.63589(14) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.53025(16) 0.52853(16) 0.48536(14) 0.0139(3) Uani 1 1 d . . . . .
C11 C 0.41567(17) 0.53584(17) 0.41194(15) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.37685(17) 0.65637(18) 0.35987(16) 0.0192(3) Uani 1 1 d . . . . .
C13 C 0.45381(18) 0.76841(17) 0.38323(15) 0.0186(3) Uani 1 1 d . . . . .
C14 C 0.56662(17) 0.76596(17) 0.45509(16) 0.0183(3) Uani 1 1 d . . . . .
C15 C 0.60455(16) 0.64439(17) 0.50571(15) 0.0163(3) Uani 1 1 d . . . . .
H2 H 0.778(2) 0.429(2) 0.5397(19) 0.017(5) Uiso 1 1 d . . . . .
H3 H 0.839(2) 0.310(2) 0.714(2) 0.030(6) Uiso 1 1 d . . . . .
H4 H 0.676(2) 0.184(2) 0.815(2) 0.035(6) Uiso 1 1 d . . . . .
H5 H 0.450(2) 0.184(2) 0.746(2) 0.024(5) Uiso 1 1 d . . . . .
H6 H 0.518(2) 0.020(2) 0.6062(18) 0.019(5) Uiso 1 1 d . . . . .
H7 H 0.615(2) 0.088(2) 0.422(2) 0.023(5) Uiso 1 1 d . . . . .
H8 H 0.658(2) 0.318(2) 0.3874(18) 0.016(5) Uiso 1 1 d . . . . .
H11 H 0.365(2) 0.460(2) 0.4017(19) 0.022(5) Uiso 1 1 d . . . . .
H12 H 0.301(2) 0.661(2) 0.309(2) 0.030(6) Uiso 1 1 d . . . . .
H14 H 0.620(2) 0.850(2) 0.4700(19) 0.023(5) Uiso 1 1 d . . . . .
H15 H 0.684(2) 0.643(2) 0.551(2) 0.021(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.3635(19) . ?
O1 C9 1.217(2) . ?
C1 C2 1.528(2) . ?
C1 C8 1.536(2) . ?
C1 C9 1.485(2) . ?
C1 C10 1.486(2) . ?
C2 C3 1.473(3) . ?
C2 C8 1.543(2) . ?
C2 H2 0.95(2) . ?
C3 C4 1.324(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.522(3) . ?
C4 H4 0.93(3) . ?
C5 C6 1.520(2) . ?
C5 C9 1.514(2) . ?
C5 H5 0.97(2) . ?
C6 C7 1.328(2) . ?
C6 H6 0.94(2) . ?
C7 C8 1.476(2) . ?
C7 H7 0.96(2) . ?
C8 H8 0.97(2) . ?
C10 C11 1.401(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.389(2) . ?
C11 H11 0.91(2) . ?
C12 C13 1.379(2) . ?
C12 H12 0.94(2) . ?
C13 C14 1.375(2) . ?
C14 C15 1.389(2) . ?
C14 H14 1.01(2) . ?
C15 H15 0.94(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 60.48(11) . . ?
C9 C1 C2 112.49(14) . . ?
C9 C1 C8 112.83(13) . . ?
C9 C1 C10 117.95(14) . . ?
C10 C1 C2 120.33(14) . . ?
C10 C1 C8 120.01(14) . . ?
C1 C2 C8 60.02(10) . . ?
C1 C2 H2 115.5(12) . . ?
C3 C2 C1 118.32(15) . . ?
C3 C2 C8 120.95(15) . . ?
C3 C2 H2 115.7(12) . . ?
C8 C2 H2 114.8(13) . . ?
C2 C3 H3 118.1(13) . . ?
C4 C3 C2 121.43(16) . . ?
C4 C3 H3 120.5(13) . . ?
C3 C4 C5 118.36(16) . . ?
C3 C4 H4 123.9(15) . . ?
C5 C4 H4 117.6(15) . . ?
C4 C5 H5 113.6(13) . . ?
C6 C5 C4 104.90(14) . . ?
C6 C5 H5 112.6(13) . . ?
C9 C5 C4 108.35(14) . . ?
C9 C5 C6 109.82(14) . . ?
C9 C5 H5 107.6(13) . . ?
C5 C6 H6 117.1(13) . . ?
C7 C6 C5 118.82(16) . . ?
C7 C6 H6 123.6(13) . . ?
C6 C7 C8 120.75(16) . . ?
C6 C7 H7 122.6(13) . . ?
C8 C7 H7 116.6(13) . . ?
C1 C8 C2 59.51(10) . . ?
C1 C8 H8 112.5(12) . . ?
C2 C8 H8 114.4(12) . . ?
C7 C8 C1 118.89(14) . . ?
C7 C8 C2 120.91(15) . . ?
C7 C8 H8 117.5(12) . . ?
O1 C9 C1 122.94(16) . . ?
O1 C9 C5 122.59(15) . . ?
C1 C9 C5 114.46(14) . . ?
C11 C10 C1 119.63(14) . . ?
C15 C10 C1 121.54(14) . . ?
C15 C10 C11 118.79(15) . . ?
C10 C11 H11 118.2(13) . . ?
C12 C11 C10 120.82(15) . . ?
C12 C11 H11 120.9(13) . . ?
C11 C12 H12 121.0(13) . . ?
C13 C12 C11 118.07(15) . . ?
C13 C12 H12 120.9(13) . . ?
F1 C13 C12 118.27(15) . . ?
F1 C13 C14 118.66(15) . . ?
C14 C13 C12 123.07(15) . . ?
C13 C14 C15 118.09(16) . . ?
C13 C14 H14 120.7(12) . . ?
C15 C14 H14 121.2(12) . . ?
C10 C15 H15 121.5(13) . . ?
C14 C15 C10 121.15(15) . . ?
C14 C15 H15 117.3(13) . . ?

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
C1 C2 C3 C4 24.2(3) . . . . ?
C1 C2 C8 C7 -107.51(17) . . . . ?
C1 C8 C2 C1 0.000(0) . . . . ?
C1 C8 C2 C3 107.02(18) . . . . ?
C1 C8 C7 C6 -23.6(2) . . . . ?
C1 C9 C5 C4 58.17(18) . . . . ?
C1 C9 C5 C6 -55.88(18) . . . . ?
C2 C1 C9 O1 145.32(16) . . . . ?
C2 C8 C1 C2 0.000(0) . . . . ?
C3 C4 C5 C6 75.2(2) . . . . ?
C4 C5 C9 O1 -121.11(18) . . . . ?
C5 C4 C3 C2 2.3(3) . . . . ?
C5 C9 C1 C2 -33.95(19) . . . . ?
C6 C5 C9 O1 124.85(17) . . . . ?
C6 C7 C8 C2 46.2(2) . . . . ?
C7 C6 C5 C4 -75.53(19) . . . . ?
C7 C8 C1 C2 110.86(18) . . . . ?
C7 C8 C2 C3 -0.5(2) . . . . ?
C8 C1 C2 C3 -111.32(18) . . . . ?
C8 C1 C9 O1 -148.54(16) . . . . ?
C8 C1 C9 C5 32.20(19) . . . . ?
C8 C2 C1 C8 0.000(0) . . . . ?
C8 C2 C3 C4 -46.0(3) . . . . ?
C8 C7 C6 C5 -2.0(3) . . . . ?
C9 C1 C2 C3 -6.9(2) . . . . ?
C9 C1 C2 C8 104.37(15) . . . . ?
C9 C1 C8 C2 -103.80(15) . . . . ?
C9 C1 C8 C7 7.1(2) . . . . ?
C9 C5 C4 C3 -42.1(2) . . . . ?
C9 C5 C6 C7 40.7(2) . . . . ?
C10 C1 C2 C3 139.13(16) . . . . ?
C10 C1 C2 C8 -109.54(17) . . . . ?
C10 C1 C8 C2 110.06(17) . . . . ?
C10 C1 C8 C7 -139.08(16) . . . . ?
C10 C1 C9 O1 -1.6(2) . . . . ?
C10 C1 C9 C5 179.09(14) . . . . ?
C11 C10 C1 C2 149.48(16) . . . . ?
C11 C10 C1 C8 78.23(19) . . . . ?
C11 C10 C1 C9 -66.2(2) . . . . ?
C15 C10 C1 C2 -32.7(2) . . . . ?
C15 C10 C1 C8 -103.97(18) . . . . ?
C15 C10 C1 C9 111.57(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1c_17srv234
_database_code_depnum_ccdc_archive 'CCDC 1857578'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)9-(4-Fluorophenyl)-1-(4-anisyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C22 H19 F O2'
_chemical_formula_sum            'C22 H19 F O2'
_chemical_formula_weight         334.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.0612(11)
_cell_length_b                   7.1500(5)
_cell_length_c                   14.5266(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.455(3)
_cell_angle_gamma                90
_cell_volume                     1650.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6640
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1399 before and 0.0560 after correction. 
The Ratio of minimum to maximum transmission is 0.9131. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            32917
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.495
_diffrn_reflns_theta_min         2.564
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3185
_reflns_number_total             4596
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2016)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4596
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.022
_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)+(0.0400P)²+0.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.00965(6) 0.85318(16) 0.68426(7) 0.0384(3) Uani 1 1 d . . . . .
O1 O 0.29031(7) 0.86045(14) 0.46251(7) 0.0184(2) Uani 1 1 d . . . . .
O2 O 0.44916(6) 0.53086(14) 0.86918(7) 0.0191(2) Uani 1 1 d . . . . .
C1 C 0.29547(8) 0.52802(19) 0.49186(10) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.27088(9) 0.3414(2) 0.44822(10) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.34633(9) 0.4585(2) 0.41891(10) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.33631(10) 0.5467(2) 0.32683(10) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.26775(10) 0.6453(2) 0.29518(11) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.19923(9) 0.6614(2) 0.35531(10) 0.0175(3) Uani 1 1 d . . . . .
C7 C 0.15519(10) 0.4743(2) 0.34209(10) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.19235(9) 0.3238(2) 0.38353(10) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.23922(9) 0.69531(19) 0.45837(10) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.17168(9) 0.7346(2) 0.51880(10) 0.0165(3) Uani 1 1 d . . . . .
C11 C 0.15271(10) 0.9183(2) 0.54003(11) 0.0219(3) Uani 1 1 d . . . . .
C12 C 0.09090(10) 0.9588(3) 0.59429(12) 0.0262(4) Uani 1 1 d . . . . .
C13 C 0.04914(9) 0.8136(3) 0.62819(11) 0.0260(4) Uani 1 1 d . . . . .
C14 C 0.06460(10) 0.6300(3) 0.60859(12) 0.0276(4) Uani 1 1 d . . . . .
C15 C 0.12604(10) 0.5919(2) 0.55318(12) 0.0231(3) Uani 1 1 d . . . . .
C16 C 0.33790(8) 0.52933(19) 0.59108(10) 0.0137(3) Uani 1 1 d . . . . .
C17 C 0.40882(9) 0.63793(19) 0.61817(10) 0.0152(3) Uani 1 1 d . . . . .
C18 C 0.44898(9) 0.64095(19) 0.70976(10) 0.0149(3) Uani 1 1 d . . . . .
C19 C 0.41655(9) 0.53403(19) 0.77602(10) 0.0142(3) Uani 1 1 d . . . . .
C20 C 0.34613(9) 0.4230(2) 0.75037(10) 0.0161(3) Uani 1 1 d . . . . .
C21 C 0.30787(9) 0.4198(2) 0.65887(10) 0.0158(3) Uani 1 1 d . . . . .
C22 C 0.52506(10) 0.6345(2) 0.89641(12) 0.0222(3) Uani 1 1 d . . . . .
H1 H 0.3271(13) 0.852(3) 0.4253(15) 0.041(6) Uiso 1 1 d . . . . .
H2 H 0.2894(9) 0.234(2) 0.4845(11) 0.014(4) Uiso 1 1 d . . . . .
H3 H 0.4020(10) 0.408(2) 0.4434(11) 0.020(4) Uiso 1 1 d . . . . .
H4 H 0.3814(10) 0.527(2) 0.2896(12) 0.023(4) Uiso 1 1 d . . . . .
H5 H 0.2594(10) 0.699(2) 0.2347(13) 0.024(4) Uiso 1 1 d . . . . .
H6 H 0.1602(10) 0.761(2) 0.3359(11) 0.017(4) Uiso 1 1 d . . . . .
H7 H 0.1037(11) 0.461(2) 0.2992(12) 0.026(5) Uiso 1 1 d . . . . .
H8 H 0.1690(10) 0.194(2) 0.3720(11) 0.021(4) Uiso 1 1 d . . . . .
H11 H 0.1841(10) 1.015(2) 0.5157(11) 0.019(4) Uiso 1 1 d . . . . .
H12 H 0.0779(11) 1.080(3) 0.6072(13) 0.031(5) Uiso 1 1 d . . . . .
H14 H 0.0326(12) 0.532(3) 0.6338(13) 0.034(5) Uiso 1 1 d . . . . .
H15 H 0.1361(10) 0.462(3) 0.5382(11) 0.021(4) Uiso 1 1 d . . . . .
H17 H 0.4319(9) 0.714(2) 0.5719(11) 0.015(4) Uiso 1 1 d . . . . .
H18 H 0.4994(10) 0.718(2) 0.7269(11) 0.018(4) Uiso 1 1 d . . . . .
H20 H 0.3254(10) 0.351(2) 0.7969(12) 0.024(4) Uiso 1 1 d . . . . .
H21 H 0.2583(10) 0.339(2) 0.6423(11) 0.018(4) Uiso 1 1 d . . . . .
H22A H 0.5408(11) 0.615(2) 0.9639(13) 0.030(5) Uiso 1 1 d . . . . .
H22B H 0.5719(11) 0.588(2) 0.8642(12) 0.025(5) Uiso 1 1 d . . . . .
H22C H 0.5164(11) 0.769(3) 0.8825(12) 0.026(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.3641(18) . ?
O1 C9 1.4341(17) . ?
O1 H1 0.86(2) . ?
O2 C19 1.3776(17) . ?
O2 C22 1.4317(18) . ?
C1 C2 1.5048(19) . ?
C1 C3 1.514(2) . ?
C1 C9 1.5344(19) . ?
C1 C16 1.5009(19) . ?
C2 C3 1.582(2) . ?
C2 C8 1.463(2) . ?
C2 H2 0.955(16) . ?
C3 C4 1.466(2) . ?
C3 H3 0.982(16) . ?
C4 C5 1.331(2) . ?
C4 H4 0.975(17) . ?
C5 C6 1.507(2) . ?
C5 H5 0.949(18) . ?
C6 C7 1.513(2) . ?
C6 C9 1.559(2) . ?
C6 H6 0.961(16) . ?
C7 C8 1.331(2) . ?
C7 H7 0.963(18) . ?
C8 H8 1.008(17) . ?
C9 C10 1.519(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.391(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.954(17) . ?
C12 C13 1.366(2) . ?
C12 H12 0.92(2) . ?
C13 C14 1.374(2) . ?
C14 C15 1.389(2) . ?
C14 H14 0.974(19) . ?
C15 H15 0.970(18) . ?
C16 C17 1.387(2) . ?
C16 C21 1.398(2) . ?
C17 C18 1.391(2) . ?
C17 H17 0.978(16) . ?
C18 C19 1.389(2) . ?
C18 H18 0.981(16) . ?
C19 C20 1.387(2) . ?
C20 C21 1.380(2) . ?
C20 H20 0.950(17) . ?
C21 H21 0.984(16) . ?
C22 H22A 0.985(19) . ?
C22 H22B 1.000(18) . ?
C22 H22C 0.988(18) . ?

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
C9 O1 H1 110.9(14) . . ?
C19 O2 C22 116.63(11) . . ?
C2 C1 C3 63.20(9) . . ?
C2 C1 C9 116.85(12) . . ?
C3 C1 C9 112.78(12) . . ?
C16 C1 C2 117.65(12) . . ?
C16 C1 C3 117.30(12) . . ?
C16 C1 C9 117.56(12) . . ?
C1 C2 C3 58.69(9) . . ?
C1 C2 H2 116.2(9) . . ?
C3 C2 H2 112.7(9) . . ?
C8 C2 C1 119.68(13) . . ?
C8 C2 C3 119.66(13) . . ?
C8 C2 H2 117.0(9) . . ?
C1 C3 C2 58.12(9) . . ?
C1 C3 H3 115.1(10) . . ?
C2 C3 H3 113.5(10) . . ?
C4 C3 C1 119.95(13) . . ?
C4 C3 C2 119.18(13) . . ?
C4 C3 H3 117.5(10) . . ?
C3 C4 H4 116.9(10) . . ?
C5 C4 C3 121.14(14) . . ?
C5 C4 H4 121.9(10) . . ?
C4 C5 C6 118.55(14) . . ?
C4 C5 H5 122.0(10) . . ?
C6 C5 H5 119.3(10) . . ?
C5 C6 C7 103.10(12) . . ?
C5 C6 C9 109.61(12) . . ?
C5 C6 H6 112.8(9) . . ?
C7 C6 C9 112.23(12) . . ?
C7 C6 H6 110.0(9) . . ?
C9 C6 H6 109.0(10) . . ?
C6 C7 H7 120.5(11) . . ?
C8 C7 C6 119.19(14) . . ?
C8 C7 H7 120.0(11) . . ?
C2 C8 H8 116.8(9) . . ?
C7 C8 C2 120.51(14) . . ?
C7 C8 H8 122.7(9) . . ?
O1 C9 C1 108.78(11) . . ?
O1 C9 C6 108.70(11) . . ?
O1 C9 C10 106.05(11) . . ?
C1 C9 C6 108.89(11) . . ?
C10 C9 C1 113.45(11) . . ?
C10 C9 C6 110.82(12) . . ?
C11 C10 C9 120.02(13) . . ?
C15 C10 C9 122.08(13) . . ?
C15 C10 C11 117.90(14) . . ?
C10 C11 H11 117.2(10) . . ?
C12 C11 C10 121.40(15) . . ?
C12 C11 H11 121.4(10) . . ?
C11 C12 H12 121.1(12) . . ?
C13 C12 C11 118.49(16) . . ?
C13 C12 H12 120.4(11) . . ?
F1 C13 C12 118.50(15) . . ?
F1 C13 C14 118.95(15) . . ?
C12 C13 C14 122.54(15) . . ?
C13 C14 C15 118.24(16) . . ?
C13 C14 H14 119.3(11) . . ?
C15 C14 H14 122.4(11) . . ?
C10 C15 H15 120.4(10) . . ?
C14 C15 C10 121.40(16) . . ?
C14 C15 H15 118.2(10) . . ?
C17 C16 C1 120.93(12) . . ?
C17 C16 C21 117.87(13) . . ?
C21 C16 C1 121.20(12) . . ?
C16 C17 C18 121.75(13) . . ?
C16 C17 H17 119.6(9) . . ?
C18 C17 H17 118.7(9) . . ?
C17 C18 H18 120.1(10) . . ?
C19 C18 C17 119.07(13) . . ?
C19 C18 H18 120.8(10) . . ?
O2 C19 C18 124.24(13) . . ?
O2 C19 C20 115.57(12) . . ?
C20 C19 C18 120.18(13) . . ?
C19 C20 H20 118.6(10) . . ?
C21 C20 C19 119.88(13) . . ?
C21 C20 H20 121.5(11) . . ?
C16 C21 H21 120.4(9) . . ?
C20 C21 C16 121.22(13) . . ?
C20 C21 H21 118.4(9) . . ?
O2 C22 H22A 106.6(10) . . ?
O2 C22 H22B 111.5(10) . . ?
O2 C22 H22C 111.0(10) . . ?
H22A C22 H22B 108.6(14) . . ?
H22A C22 H22C 110.2(14) . . ?
H22B C22 H22C 108.8(14) . . ?

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
_geom_hbond_publ_flag
O1 H1 O2 0.86(2) 2.38(2) 3.1574(15) 150.1(18) 4_575 yes

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
C1 C2 C3 C4 -109.02(15) . . . . ?
C1 C2 C8 C7 19.6(2) . . . . ?
C1 C3 C2 C1 0.000(0) . . . . ?
C1 C3 C2 C8 108.69(15) . . . . ?
C1 C3 C4 C5 -20.5(2) . . . . ?
C1 C9 C6 C5 -61.11(14) . . . . ?
C1 C9 C6 C7 52.81(16) . . . . ?
C1 C9 C10 C11 139.43(14) . . . . ?
C1 C9 C10 C15 -41.74(19) . . . . ?
C2 C1 C3 C4 107.71(15) . . . . ?
C2 C1 C9 O1 -147.89(12) . . . . ?
C2 C1 C9 C6 -29.57(16) . . . . ?
C2 C1 C9 C10 94.35(15) . . . . ?
C2 C1 C16 C17 134.36(14) . . . . ?
C2 C1 C16 C21 -44.94(18) . . . . ?
C2 C3 C1 C2 0.000(0) . . . . ?
C2 C3 C1 C9 -109.68(13) . . . . ?
C2 C3 C1 C16 108.92(14) . . . . ?
C2 C3 C4 C5 47.3(2) . . . . ?
C2 C8 C7 C6 5.9(2) . . . . ?
C3 C1 C2 C8 -108.67(15) . . . . ?
C3 C1 C9 O1 -77.49(14) . . . . ?
C3 C1 C9 C6 40.82(15) . . . . ?
C3 C1 C9 C10 164.74(12) . . . . ?
C3 C1 C16 C17 61.96(17) . . . . ?
C3 C1 C16 C21 -117.33(14) . . . . ?
C3 C2 C1 C3 0.000(0) . . . . ?
C3 C2 C1 C9 103.32(14) . . . . ?
C3 C2 C1 C16 -108.39(14) . . . . ?
C3 C2 C8 C7 -49.1(2) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C4 C3 C1 C9 -1.97(18) . . . . ?
C4 C3 C1 C16 -143.36(13) . . . . ?
C4 C3 C2 C8 -0.3(2) . . . . ?
C4 C5 C6 C7 -77.46(16) . . . . ?
C4 C5 C6 C9 42.22(18) . . . . ?
C5 C6 C7 C8 74.49(17) . . . . ?
C5 C6 C9 O1 57.26(15) . . . . ?
C5 C6 C9 C10 173.43(12) . . . . ?
C6 C9 C1 C16 -177.89(12) . . . . ?
C6 C9 C10 C11 -97.71(15) . . . . ?
C6 C9 C10 C15 81.12(17) . . . . ?
C7 C6 C9 O1 171.18(12) . . . . ?
C7 C6 C9 C10 -72.65(15) . . . . ?
C8 C2 C1 C9 -5.34(19) . . . . ?
C8 C2 C1 C16 142.95(13) . . . . ?
C8 C7 C6 C9 -43.37(19) . . . . ?
C9 C1 C16 C17 -77.58(17) . . . . ?
C9 C1 C16 C21 103.12(15) . . . . ?
C10 C9 C1 C16 -53.97(16) . . . . ?
C11 C10 C9 O1 20.09(18) . . . . ?
C15 C10 C9 O1 -161.08(13) . . . . ?
C16 C1 C9 O1 63.80(15) . . . . ?
C18 C19 O2 C22 -4.9(2) . . . . ?
C20 C19 O2 C22 176.00(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1b_320k
_database_code_depnum_ccdc_archive 'CCDC 1857582'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-10-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1

_chemical_name_common            ?
_chemical_name_systematic        
;
(+/-)1,9-Bis(4-fluorophenyl)tricyclo[3.3.1.0^2,8^]nona-3,6-dien-9-ol
;
_chemical_formula_moiety         'C21 H16 F2 O'
_chemical_formula_sum            'C21 H16 F2 O'
_chemical_formula_weight         322.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H16 F2 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.8199(3)
_cell_length_b                   6.2643(2)
_cell_length_c                   24.9393(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.510(3)
_cell_angle_gamma                90
_cell_volume                     1534.09(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3162
_cell_measurement_temperature    320(2)
_cell_measurement_theta_max      29.5030
_cell_measurement_theta_min      2.4680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         3.197
_diffrn_ambient_temperature      320.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029  -57.0000  -60.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega   72.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029 -178.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00  113.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029 -178.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega  -24.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029 -100.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega  -36.00  107.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029    0.0000  120.0000 143

#__ type_ start__ end____ width___ exp.time_
  6 omega   60.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       31.9029  178.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega  -77.00  -52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -31.1216 -178.0000  150.0000 25
;
_diffrn_measurement_device       'Xcalibur, Sapphire3'
_diffrn_measurement_device_type  '4-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0361734000
_diffrn_orient_matrix_UB_12      0.0662390000
_diffrn_orient_matrix_UB_13      0.0180245000
_diffrn_orient_matrix_UB_21      0.0607235000
_diffrn_orient_matrix_UB_22      0.0173533000
_diffrn_orient_matrix_UB_23      0.0149763000
_diffrn_orient_matrix_UB_31      0.0148705000
_diffrn_orient_matrix_UB_32      0.0901971000
_diffrn_orient_matrix_UB_33      -0.0161139000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tubeEnhance (Mo) X-ray Source'
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2710
_reflns_number_total             4085
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.023
_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)+(0.0430P)²+0.2120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1174
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C6(H6), C5(H5), C11(H11), C7(H7), C20(H20), C17(H17), C15(H15),
 C8(H8), C18(H18), C12(H12), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.40024(14) 0.5015(2) 0.09975(5) 0.0383(3) Uani 1 1 d . . . . .
O1 O 0.43876(13) 0.71754(16) 0.11120(4) 0.0518(3) Uani 1 1 d . . . . .
C1 C 0.32398(14) 0.4077(2) 0.15063(5) 0.0411(3) Uani 1 1 d . . . . .
C16 C 0.53122(14) 0.3817(2) 0.08810(5) 0.0380(3) Uani 1 1 d . . . . .
C10 C 0.42097(16) 0.3930(2) 0.19812(5) 0.0451(3) Uani 1 1 d . . . . .
C3 C 0.30322(15) 0.5018(2) 0.05252(6) 0.0444(3) Uani 1 1 d . . . . .
H3 H 0.340893 0.551011 0.018430 0.053 Uiso 1 1 calc R . . . .
C21 C 0.52888(15) 0.1824(2) 0.06365(6) 0.0435(3) Uani 1 1 d . . . . .
H21 H 0.445720 0.124273 0.053075 0.052 Uiso 1 1 calc R . . . .
C6 C 0.25508(15) 0.1978(2) 0.13698(6) 0.0473(4) Uani 1 1 d . . . . .
H6 H 0.256643 0.087076 0.161830 0.057 Uiso 1 1 calc R . . . .
C5 C 0.19258(15) 0.1696(2) 0.09012(7) 0.0518(4) Uani 1 1 d . . . . .
H5 H 0.145153 0.043480 0.083753 0.062 Uiso 1 1 calc R . . . .
C11 C 0.49824(17) 0.2100(3) 0.20703(6) 0.0523(4) Uani 1 1 d . . . . .
H11 H 0.487857 0.093806 0.184128 0.063 Uiso 1 1 calc R . . . .
C7 C 0.20055(16) 0.5483(2) 0.16042(6) 0.0500(4) Uani 1 1 d . . . . .
H7 H 0.177589 0.585565 0.195287 0.060 Uiso 1 1 calc R . . . .
C20 C 0.64707(16) 0.0681(3) 0.05462(6) 0.0509(4) Uani 1 1 d . . . . .
H20 H 0.643889 -0.066331 0.038819 0.061 Uiso 1 1 calc R . . . .
F2 F 0.88456(10) 0.0455(2) 0.05971(5) 0.0888(4) Uani 1 1 d . . . . .
C17 C 0.65731(16) 0.4648(3) 0.10275(6) 0.0515(4) Uani 1 1 d . . . . .
H17 H 0.661974 0.597773 0.119230 0.062 Uiso 1 1 calc R . . . .
C15 C 0.44041(18) 0.5641(3) 0.23287(6) 0.0562(4) Uani 1 1 d . . . . .
H15 H 0.390523 0.688557 0.227514 0.067 Uiso 1 1 calc R . . . .
C9 C 0.16005(16) 0.5716(2) 0.06417(6) 0.0518(4) Uani 1 1 d . . . . .
H9 H 0.114159 0.657045 0.036496 0.062 Uiso 1 1 calc R . . . .
C4 C 0.19681(16) 0.3316(2) 0.04865(7) 0.0509(4) Uani 1 1 d . . . . .
H4 H 0.171021 0.285636 0.012401 0.061 Uiso 1 1 calc R . . . .
C8 C 0.12519(16) 0.6184(2) 0.11958(7) 0.0515(4) Uani 1 1 d . . . . .
H8 H 0.048051 0.699520 0.126556 0.062 Uiso 1 1 calc R . . . .
C19 C 0.76791(16) 0.1571(3) 0.06941(7) 0.0559(4) Uani 1 1 d . . . . .
C18 C 0.77624(17) 0.3526(3) 0.09317(7) 0.0612(5) Uani 1 1 d . . . . .
H18 H 0.860367 0.409764 0.102796 0.073 Uiso 1 1 calc R . . . .
F1 F 0.69443(14) 0.3591(2) 0.32403(5) 0.0947(4) Uani 1 1 d . . . . .
C13 C 0.60437(19) 0.3706(3) 0.28237(7) 0.0636(5) Uani 1 1 d . . . . .
C12 C 0.59037(18) 0.1973(3) 0.24935(7) 0.0614(5) Uani 1 1 d . . . . .
H12 H 0.641343 0.074185 0.255165 0.074 Uiso 1 1 calc R . . . .
C14 C 0.5321(2) 0.5537(3) 0.27523(7) 0.0654(5) Uani 1 1 d . . . . .
H14 H 0.544045 0.669096 0.298247 0.079 Uiso 1 1 calc R . . . .
H1 H 0.364(2) 0.795(4) 0.1108(9) 0.098(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O1 1.4333(16) . ?
C2 C1 1.5915(18) . ?
C2 C16 1.5195(19) . ?
C2 C3 1.5082(19) . ?
O1 H1 0.88(2) . ?
C1 C10 1.516(2) . ?
C1 C6 1.516(2) . ?
C1 C7 1.520(2) . ?
C16 C21 1.3896(19) . ?
C16 C17 1.389(2) . ?
C10 C11 1.392(2) . ?
C10 C15 1.390(2) . ?
C3 H3 0.9800 . ?
C3 C9 1.503(2) . ?
C3 C4 1.496(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.384(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.327(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.450(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.328(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.359(2) . ?
F2 C19 1.3653(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(2) . ?
C9 H9 0.9800 . ?
C9 C4 1.595(2) . ?
C9 C8 1.456(2) . ?
C4 H4 0.9800 . ?
C8 H8 0.9300 . ?
C19 C18 1.363(3) . ?
C18 H18 0.9300 . ?
F1 C13 1.360(2) . ?
C13 C12 1.369(3) . ?
C13 C14 1.359(3) . ?
C12 H12 0.9300 . ?
C14 H14 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
O1 C2 C1 108.35(11) . . ?
O1 C2 C16 106.39(11) . . ?
O1 C2 C3 108.55(11) . . ?
C16 C2 C1 112.03(11) . . ?
C3 C2 C1 108.94(11) . . ?
C3 C2 C16 112.42(11) . . ?
C2 O1 H1 107.3(15) . . ?
C10 C1 C2 110.39(11) . . ?
C10 C1 C6 113.49(12) . . ?
C10 C1 C7 113.96(12) . . ?
C6 C1 C2 110.69(11) . . ?
C6 C1 C7 100.59(12) . . ?
C7 C1 C2 107.21(11) . . ?
C21 C16 C2 121.13(12) . . ?
C17 C16 C2 121.24(13) . . ?
C17 C16 C21 117.60(13) . . ?
C11 C10 C1 120.83(13) . . ?
C15 C10 C1 121.48(14) . . ?
C15 C10 C11 117.64(15) . . ?
C2 C3 H3 115.9 . . ?
C9 C3 C2 115.78(12) . . ?
C9 C3 H3 115.9 . . ?
C4 C3 C2 119.05(12) . . ?
C4 C3 H3 115.9 . . ?
C4 C3 C9 64.25(10) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 C16 121.71(14) . . ?
C20 C21 H21 119.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.99(13) . . ?
C5 C6 H6 119.5 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.28(14) . . ?
C4 C5 H5 119.4 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.32(16) . . ?
C12 C11 H11 119.3 . . ?
C1 C7 H7 119.7 . . ?
C8 C7 C1 120.52(14) . . ?
C8 C7 H7 119.7 . . ?
C21 C20 H20 120.8 . . ?
C19 C20 C21 118.37(15) . . ?
C19 C20 H20 120.8 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.02(15) . . ?
C18 C17 H17 119.5 . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.64(16) . . ?
C14 C15 H15 119.2 . . ?
C3 C9 H9 116.6 . . ?
C3 C9 C4 57.64(10) . . ?
C4 C9 H9 116.6 . . ?
C8 C9 C3 118.03(14) . . ?
C8 C9 H9 116.6 . . ?
C8 C9 C4 118.40(13) . . ?
C3 C4 C9 58.10(10) . . ?
C3 C4 H4 116.3 . . ?
C5 C4 C3 118.52(14) . . ?
C5 C4 C9 118.62(13) . . ?
C5 C4 H4 116.3 . . ?
C9 C4 H4 116.3 . . ?
C7 C8 C9 121.81(14) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C20 C19 F2 118.28(16) . . ?
C20 C19 C18 122.38(15) . . ?
C18 C19 F2 119.34(15) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 118.91(15) . . ?
C19 C18 H18 120.5 . . ?
F1 C13 C12 118.58(17) . . ?
C14 C13 F1 118.69(18) . . ?
C14 C13 C12 122.73(17) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.29(17) . . ?
C13 C12 H12 120.9 . . ?
C15 C14 H14 120.8 . . ?
C13 C14 C15 118.37(17) . . ?
C13 C14 H14 120.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
