# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a20210346_iiq
_database_code_depnum_ccdc_archive 'CCDC 2145250'
loop_
_audit_author_name
_audit_author_address
'Leire San Felices'
;Universidad del Pais Vasco UPV EHU
Spain
;
_audit_update_record             
;
2022-01-28 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;

_audit_creation_date             2022-01-18T22:01:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C20 H20 O2'
_chemical_formula_sum            'C20 H20 O2'
_chemical_formula_weight         292.36
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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                   5.82822(4)
_cell_length_b                   13.81370(9)
_cell_length_c                   18.94391(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1525.159(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.99(13)
_cell_measurement_reflns_used    16736
_cell_measurement_theta_min      3.923
_cell_measurement_theta_max      72.547

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.062
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 1 0.1068
0 -2 -5 0.041
3 0 -5 0.1252
0 1 2 0.0345
-4 0 1 0.1022
0 -7 8 0.0301
4 -1 0 0.1324
0 7 -8 0.0317


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.965

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      150.99(13)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0319057
_diffrn_orient_matrix_ub_12      0.0457356
_diffrn_orient_matrix_ub_13      0.0735425
_diffrn_orient_matrix_ub_21      -0.0621706
_diffrn_orient_matrix_ub_22      0.1000019
_diffrn_orient_matrix_ub_23      -0.0305142
_diffrn_orient_matrix_ub_31      -0.2548195
_diffrn_orient_matrix_ub_32      -0.0186723
_diffrn_orient_matrix_ub_33      0.0166457
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_number            27285
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.961
_diffrn_reflns_theta_max         68.996
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_coverage         0.701
_reflns_number_total             2818
_reflns_number_gt                2695
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  41.00   1.00    1.00    --  -37.50  38.00-150.00  110
  2  ω   -124.00 -80.00   1.00    1.00    --  -37.50 -99.00 -60.00   44
  3  ω    -63.00   5.00   1.00    1.00    --  -37.50  38.00   0.00   68
  4  ω    -99.00  -9.00   1.00    1.00    --  -37.50 -38.00  30.00   90
  5  ω    -91.00 -39.00   1.00    1.00    --  -37.50 -38.00 -90.00   52
  6  ω   -116.00 -19.00   1.00    1.00    --  -37.50 -38.00-150.00   97
  7  ω     81.00 108.00   1.00    1.00    --   37.50 125.00  30.00   27
  8  ω     38.00  65.00   1.00    1.00    --   37.50  57.00 -30.00   27
  9  ω     45.00  77.00   1.00    1.00    --  110.55 -45.00-150.00   32
 10  ω     25.00  76.00   1.00    1.00    --  110.55-111.00 150.00   51
 11  ω     29.00  75.00   1.00    1.00    --  110.55 -45.00  90.00   46
 12  ω     36.00  64.00   1.00    1.00    --  110.55 -30.00 -30.00   28
 13  ω    123.00 157.00   1.00    1.00    --  110.55  61.00-120.00   34
 14  ω     82.00 108.00   1.00    1.00    --  110.55 -94.00 -30.00   26
 15  ω     64.00 149.00   1.00    1.00    --  110.55   0.00-150.00   85
 16  ω     71.00  98.00   1.00    1.00    --  110.55  77.00-120.00   27
 17  ω    115.00 149.00   1.00    1.00    --  110.55  61.00-150.00   34
 18  ω     38.00  63.00   1.00    1.00    --  110.55 -45.00  60.00   25
 19  ω     74.00 105.00   1.00    1.00    --  110.55  61.00-150.00   31
 20  ω     34.00  61.00   1.00    1.00    --  110.55 -30.00 -60.00   27
 21  ω     39.00  77.00   1.00    1.00    --  110.55 -45.00-120.00   38
 22  ω     76.00 101.00   1.00    1.00    --  110.55  61.00 -90.00   25
 23  ω     76.00 147.00   1.00    1.00    --  110.55  61.00  90.00   71
 24  ω    100.00 127.00   1.00    1.00    --  110.55  77.00 -90.00   27
 25  ω     40.00  67.00   1.00    1.00    --  110.55 -30.00-180.00   27
 26  ω     78.00 105.00   1.00    1.00    --  110.55  61.00-120.00   27
 27  ω     76.00 103.00   1.00    1.00    --  110.55  45.00 -90.00   27
 28  ω     74.00 153.00   1.00    1.00    --  110.55  61.00 -60.00   79
 29  ω     72.00  99.00   1.00    1.00    --  110.55  77.00 -90.00   27
 30  ω     29.00 148.00   1.00    1.00    --  110.55 -61.00 -60.00  119
 31  ω     28.00  55.00   1.00    1.00    --  110.55   0.00-150.00   27
 32  ω     66.00  93.00   1.00    1.00    --  110.55  30.00 -90.00   27
 33  ω     80.00 105.00   1.00    1.00    --  110.55  30.00 -60.00   25
 34  ω     67.00  92.00   1.00    1.00    --  110.55  30.00 -30.00   25
 35  ω    120.00 155.00   1.00    1.00    --  110.55  30.00 -30.00   35
 36  ω     72.00  99.00   1.00    1.00    --  110.55  36.00 -48.46   27
 37  ω    -94.00 -26.00   1.00    1.00    --  -37.50 125.00-180.00   68
 38  ω    -38.00  26.00   1.00    1.00    --   37.50 -77.00-150.00   64
 39  ω      5.00  99.00   1.00    1.00    --   37.50-125.00  60.00   94
 40  ω     45.00  77.00   1.00    1.00    --  110.55 -45.00 120.00   32
 41  ω     60.00 101.00   1.00    1.00    --  110.55 -94.00  60.00   41
 42  ω     63.00 110.00   1.00    1.00    --  110.55-111.00-180.00   47
 43  ω     53.00  80.00   1.00    1.00    --  110.55-111.00 -90.00   27
 44  ω     55.00 112.00   1.00    1.00    --  110.55-111.00 -30.00   57
 45  ω     51.00 109.00   1.00    1.00    --  110.55 -94.00-150.00   58
 46  ω   -129.00   2.00   1.00    1.00    --  -37.50 -77.00   0.00  131
 47  ω   -129.00   2.00   1.00    1.00    --  -37.50 -77.00-180.00  131
 48  ω   -100.00  -2.00   1.00    1.00    --  -37.50 125.00  30.00   98
 49  ω   -121.00 -73.00   1.00    1.00    --  -37.50-125.00 120.00   48
 50  ω     -2.00  99.00   1.00    1.00    --   37.50  77.00 150.00  101
 51  ω     73.00 121.00   1.00    1.00    --   37.50 125.00-180.00   48
 52  ω   -126.00 -79.00   1.00    1.00    --  -37.50 -99.00  90.00   47
 53  ω   -129.00   2.00   1.00    1.00    --  -37.50 -77.00 120.00  131
 54  ω   -129.00   2.00   1.00    1.00    --  -37.50 -77.00-120.00  131
 55  ω   -122.00   0.00   1.00    1.00    --  -37.50 -38.00   0.00  122
 56  ω    -77.00  54.00   1.00    1.00    --  -37.50  77.00 -30.00  131
 57  ω   -122.00  -1.00   1.00    1.00    --  -37.50 -56.00  22.00  121
 58  ω   -122.00   0.00   1.00    1.00    --  -37.50 -38.00 120.00  122
 59  ω   -122.00  -1.00   1.00    1.00    --  -37.50 -57.00   0.00  121
 60  ω   -126.00  46.00   1.00    1.00    --  -37.50 -19.00-150.00  172
 61  ω   -100.00  -2.00   1.00    1.00    --  -37.50 125.00-150.00   98
 62  ω    -71.00  47.00   1.00    1.00    --  -37.50  38.00 -60.00  118
 63  ω   -122.00  -1.00   1.00    1.00    --  -37.50 -57.00 120.00  121
 64  ω   -122.00   0.00   1.00    1.00    --  -37.50 -38.00-180.00  122
 65  ω   -126.00 -79.00   1.00    1.00    --  -37.50 -99.00  60.00   47
 66  ω     -2.00 129.00   1.00    1.00    --   37.50  77.00  30.00  131
 67  ω    -58.00 133.00   1.00    1.00    --   37.50   0.00-180.00  191
 68  ω      1.00 122.00   1.00    1.00    --   37.50  57.00  30.00  121
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 shelx_SHELXL_version_number            2018/3

 The Friedel pair coverage of the experiment is almost complete (100%).
 Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON (Spek, 2009).
 The results indicated that the absolute structure had been correctly
 assigned. The method calculated that the probability that the structure 
 is inverted is smaller than 10-24. The absolute structure parameter y 
 (Hooft, Straver & Spek, 2008) was calculated using PLATON (Spek,
 2010). The resulting value was y=-0.06(8), which together with Flack
 parameter value, indicate that the absolute structure has sureley been
 determined correctly.

 Flack, H. D. (1983), Acta Cryst. A39, 876-881
 Flack & G. Bernardinelli, Acta Cryst. 1999, A55, 908-915;  
 H. D. Flack & G. Bernardinelli, J. Appl. Cryst. 2000, 33, 1143-1148.

 R. W. W. Hooft, L. H. Straver & A. L. Spek, J. Appl. Cryst. 2008, 41, 
 96-103
 Dolomanov, O.V. (2009) OLEX2, J. Appl. Cryst., 42, 339-341. 
 Spek, A.L. (2003). J. Appl. Cryst. 36, 7-13.
 Spek, A.L. (2009). Acta Cryst. D65, 148-155.
 A. L. Spek (2010) PLATON, Utrecht, The Netherlands; 
 A. L. Spek, J. Appl. Cryst. 2003, 36, 7-13
 A. L. Thompson & D. J. Watkin, Tetrahedron: Asymmetry 2009, 20, 712--717


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.2760P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2818
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
  Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 The Friedel pair coverage of the experiment is almost complete 
 (100%). Analysis of the absolute structure using likelihood methods
 (Hooft, Straver & Spek, 2008) was performed using PLATON
 (Spek, 2009). The resulting value was y=-0.06(8)
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.1746(2) 0.42739(10) 0.86054(8) 0.0195(3) Uani 1 1 d . . . . .
C2 C -0.0211(3) 0.39505(14) 0.86180(10) 0.0133(4) Uani 1 1 d . . . . .
O12 O -0.5141(3) 0.48812(12) 0.75572(9) 0.0256(4) Uani 1 1 d . . . . .
H12 H -0.607562 0.464879 0.784927 0.038 Uiso 1 1 calc GR . . . .
C15 C -0.0650(4) 0.59600(14) 0.92139(11) 0.0182(4) Uani 1 1 d . . . . .
C17 C -0.1204(4) 0.10384(15) 0.92973(11) 0.0217(5) Uani 1 1 d . . . . .
H17 H -0.144106 0.040169 0.947222 0.026 Uiso 1 1 calc R . . . .
C9 C -0.2686(4) 0.14161(14) 0.87950(11) 0.0191(4) Uani 1 1 d . . . . .
H9 H -0.390183 0.10255 0.862073 0.023 Uiso 1 1 calc R . . . .
C7 C -0.2920(3) 0.44609(15) 0.76688(11) 0.0172(4) Uani 1 1 d . . . . .
C5 C -0.2428(4) 0.23594(14) 0.85395(10) 0.0154(4) Uani 1 1 d . . . . .
C10 C -0.3996(4) 0.26992(15) 0.79520(11) 0.0200(5) Uani 1 1 d . . . . .
H10A H -0.535262 0.301632 0.816542 0.024 Uiso 1 1 calc R . . . .
H10B H -0.454632 0.212606 0.768782 0.024 Uiso 1 1 calc R . . . .
C3 C -0.0622(4) 0.29175(14) 0.88127(10) 0.0134(4) Uani 1 1 d . . . . .
C18 C 0.1443(4) 0.64397(16) 0.92678(12) 0.0235(5) Uani 1 1 d . . . . .
H18 H 0.223108 0.662598 0.885032 0.028 Uiso 1 1 calc R . . . .
C16 C -0.0626(4) 0.59511(15) 0.78200(12) 0.0230(5) Uani 1 1 d . . . . .
H16A H -0.121085 0.658063 0.764671 0.028 Uiso 1 1 calc R . . . .
H16B H 0.105649 0.599981 0.788146 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0615(4) 0.15827(15) 0.95450(12) 0.0217(5) Uani 1 1 d . . . . .
H11 H 0.16512 0.131685 0.988003 0.026 Uiso 1 1 calc R . . . .
C4 C -0.2264(4) 0.45814(14) 0.84595(10) 0.0143(4) Uani 1 1 d . . . . .
H4 H -0.358545 0.439313 0.876702 0.017 Uiso 1 1 calc R . . . .
C19 C -0.1746(4) 0.57117(15) 0.98436(12) 0.0244(5) Uani 1 1 d . . . . .
H19 H -0.319424 0.539768 0.982269 0.029 Uiso 1 1 calc R . . . .
C21 C -0.0796(5) 0.59068(16) 1.04950(13) 0.0331(6) Uani 1 1 d . . . . .
H21 H -0.157441 0.571815 1.091363 0.04 Uiso 1 1 calc R . . . .
C13 C -0.2883(4) 0.34080(15) 0.74275(11) 0.0214(5) Uani 1 1 d . . . . .
H13A H -0.126955 0.321033 0.73496 0.026 Uiso 1 1 calc R . . . .
H13B H -0.369216 0.335896 0.696947 0.026 Uiso 1 1 calc R . . . .
C6 C 0.0914(4) 0.25190(15) 0.93005(10) 0.0177(4) Uani 1 1 d . . . . .
H6 H 0.217222 0.289361 0.946514 0.021 Uiso 1 1 calc R . . . .
C8 C -0.1793(4) 0.56773(14) 0.85263(11) 0.0178(4) Uani 1 1 d . . . . .
H8 H -0.332651 0.600191 0.852459 0.021 Uiso 1 1 calc R . . . .
C22 C 0.1292(5) 0.63781(17) 1.05369(14) 0.0324(6) Uani 1 1 d . . . . .
H22 H 0.195982 0.651304 1.098369 0.039 Uiso 1 1 calc R . . . .
C14 C -0.1227(4) 0.51350(16) 0.72952(11) 0.0219(5) Uani 1 1 d . . . . .
H14A H -0.193075 0.540865 0.686353 0.026 Uiso 1 1 calc R . . . .
H14B H 0.017452 0.477548 0.715913 0.026 Uiso 1 1 calc R . . . .
C20 C 0.2402(4) 0.66513(17) 0.99236(14) 0.0301(5) Uani 1 1 d . . . . .
H20 H 0.382453 0.698493 0.994933 0.036 Uiso 1 1 calc R . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.225(2) . ?
C2 C3 1.493(3) . ?
C2 C4 1.511(3) . ?
O12 H12 0.84 . ?
O12 C7 1.435(2) . ?
C15 C18 1.392(3) . ?
C15 C19 1.396(3) . ?
C15 C8 1.514(3) . ?
C17 H17 0.95 . ?
C17 C9 1.387(3) . ?
C17 C11 1.382(3) . ?
C9 H9 0.95 . ?
C9 C5 1.398(3) . ?
C7 C4 1.555(3) . ?
C7 C13 1.525(3) . ?
C7 C14 1.530(3) . ?
C5 C10 1.515(3) . ?
C5 C3 1.404(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C10 C13 1.539(3) . ?
C3 C6 1.400(3) . ?
C18 H18 0.95 . ?
C18 C20 1.393(3) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C16 C8 1.548(3) . ?
C16 C14 1.543(3) . ?
C11 H11 0.95 . ?
C11 C6 1.385(3) . ?
C4 H4 1 . ?
C4 C8 1.544(3) . ?
C19 H19 0.95 . ?
C19 C21 1.379(4) . ?
C21 H21 0.95 . ?
C21 C22 1.383(4) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C6 H6 0.95 . ?
C8 H8 1 . ?
C22 H22 0.95 . ?
C22 C20 1.382(4) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C20 H20 0.95 . ?

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 C3 120.18(18) . . ?
O1 C2 C4 121.56(17) . . ?
C3 C2 C4 118.23(17) . . ?
C7 O12 H12 109.5 . . ?
C18 C15 C19 117.1(2) . . ?
C18 C15 C8 124.8(2) . . ?
C19 C15 C8 118.1(2) . . ?
C9 C17 H17 119.8 . . ?
C11 C17 H17 119.8 . . ?
C11 C17 C9 120.40(19) . . ?
C17 C9 H9 119.3 . . ?
C17 C9 C5 121.4(2) . . ?
C5 C9 H9 119.3 . . ?
O12 C7 C4 108.69(17) . . ?
O12 C7 C13 110.77(17) . . ?
O12 C7 C14 105.52(16) . . ?
C13 C7 C4 112.80(16) . . ?
C13 C7 C14 115.63(18) . . ?
C14 C7 C4 102.83(16) . . ?
C9 C5 C10 118.57(19) . . ?
C9 C5 C3 117.71(19) . . ?
C3 C5 C10 123.58(17) . . ?
C5 C10 H10A 108.6 . . ?
C5 C10 H10B 108.6 . . ?
C5 C10 C13 114.65(18) . . ?
H10A C10 H10B 107.6 . . ?
C13 C10 H10A 108.6 . . ?
C13 C10 H10B 108.6 . . ?
C5 C3 C2 123.66(18) . . ?
C6 C3 C2 115.86(19) . . ?
C6 C3 C5 120.47(18) . . ?
C15 C18 H18 119.4 . . ?
C15 C18 C20 121.1(2) . . ?
C20 C18 H18 119.4 . . ?
H16A C16 H16B 108.7 . . ?
C8 C16 H16A 110.5 . . ?
C8 C16 H16B 110.5 . . ?
C14 C16 H16A 110.5 . . ?
C14 C16 H16B 110.5 . . ?
C14 C16 C8 106.19(17) . . ?
C17 C11 H11 120.3 . . ?
C17 C11 C6 119.4(2) . . ?
C6 C11 H11 120.3 . . ?
C2 C4 C7 108.93(16) . . ?
C2 C4 H4 110.1 . . ?
C2 C4 C8 114.10(17) . . ?
C7 C4 H4 110.1 . . ?
C8 C4 C7 103.16(16) . . ?
C8 C4 H4 110.1 . . ?
C15 C19 H19 118.9 . . ?
C21 C19 C15 122.2(2) . . ?
C21 C19 H19 118.9 . . ?
C19 C21 H21 120.1 . . ?
C19 C21 C22 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C7 C13 C10 114.04(17) . . ?
C7 C13 H13A 108.7 . . ?
C7 C13 H13B 108.7 . . ?
C10 C13 H13A 108.7 . . ?
C10 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C3 C6 H6 119.8 . . ?
C11 C6 C3 120.5(2) . . ?
C11 C6 H6 119.8 . . ?
C15 C8 C16 119.17(18) . . ?
C15 C8 C4 113.68(16) . . ?
C15 C8 H8 106.3 . . ?
C16 C8 H8 106.3 . . ?
C4 C8 C16 104.29(17) . . ?
C4 C8 H8 106.3 . . ?
C21 C22 H22 120.3 . . ?
C20 C22 C21 119.5(2) . . ?
C20 C22 H22 120.3 . . ?
C7 C14 C16 107.03(16) . . ?
C7 C14 H14A 110.3 . . ?
C7 C14 H14B 110.3 . . ?
C16 C14 H14A 110.3 . . ?
C16 C14 H14B 110.3 . . ?
H14A C14 H14B 108.6 . . ?
C18 C20 H20 119.8 . . ?
C22 C20 C18 120.3(2) . . ?
C22 C20 H20 119.8 . . ?

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
O1 C2 C3 C5 -148.4(2) . . . . ?
O1 C2 C3 C6 32.1(3) . . . . ?
O1 C2 C4 C7 95.6(2) . . . . ?
O1 C2 C4 C8 -19.0(3) . . . . ?
C2 C3 C6 C11 176.59(19) . . . . ?
C2 C4 C8 C15 -50.2(2) . . . . ?
C2 C4 C8 C16 81.2(2) . . . . ?
O12 C7 C4 C2 167.21(15) . . . . ?
O12 C7 C4 C8 -71.22(19) . . . . ?
O12 C7 C13 C10 -78.3(2) . . . . ?
O12 C7 C14 C16 85.4(2) . . . . ?
C15 C18 C20 C22 0.6(3) . . . . ?
C15 C19 C21 C22 1.1(4) . . . . ?
C17 C9 C5 C10 175.5(2) . . . . ?
C17 C9 C5 C3 -0.5(3) . . . . ?
C17 C11 C6 C3 0.7(3) . . . . ?
C9 C17 C11 C6 1.6(3) . . . . ?
C9 C5 C10 C13 -146.1(2) . . . . ?
C9 C5 C3 C2 -176.73(18) . . . . ?
C9 C5 C3 C6 2.8(3) . . . . ?
C7 C4 C8 C15 -168.23(17) . . . . ?
C7 C4 C8 C16 -36.9(2) . . . . ?
C5 C10 C13 C7 -84.1(2) . . . . ?
C5 C3 C6 C11 -2.9(3) . . . . ?
C10 C5 C3 C2 7.6(3) . . . . ?
C10 C5 C3 C6 -172.94(19) . . . . ?
C3 C2 C4 C7 -86.1(2) . . . . ?
C3 C2 C4 C8 159.28(17) . . . . ?
C3 C5 C10 C13 29.6(3) . . . . ?
C18 C15 C19 C21 -1.5(3) . . . . ?
C18 C15 C8 C16 -1.5(3) . . . . ?
C18 C15 C8 C4 122.1(2) . . . . ?
C11 C17 C9 C5 -1.8(3) . . . . ?
C4 C2 C3 C5 33.3(3) . . . . ?
C4 C2 C3 C6 -146.19(19) . . . . ?
C4 C7 C13 C10 43.7(2) . . . . ?
C4 C7 C14 C16 -28.5(2) . . . . ?
C19 C15 C18 C20 0.6(3) . . . . ?
C19 C15 C8 C16 179.49(19) . . . . ?
C19 C15 C8 C4 -56.9(3) . . . . ?
C19 C21 C22 C20 0.2(4) . . . . ?
C21 C22 C20 C18 -1.1(4) . . . . ?
C13 C7 C4 C2 44.0(2) . . . . ?
C13 C7 C4 C8 165.54(17) . . . . ?
C13 C7 C14 C16 -151.85(18) . . . . ?
C8 C15 C18 C20 -178.4(2) . . . . ?
C8 C15 C19 C21 177.6(2) . . . . ?
C8 C16 C14 C7 5.9(2) . . . . ?
C14 C7 C4 C2 -81.27(19) . . . . ?
C14 C7 C4 C8 40.3(2) . . . . ?
C14 C7 C13 C10 161.70(17) . . . . ?
C14 C16 C8 C15 147.39(19) . . . . ?
C14 C16 C8 C4 19.3(2) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_a20210296_e487f1
_database_code_depnum_ccdc_archive 'CCDC 2145251'
loop_
_audit_author_name
_audit_author_address
'Leire San Felices'
;Universidad del Pais Vasco UPV EHU
Spain
;
_audit_update_record             
;
2022-01-28 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;

_audit_creation_date             2022-01-14T12:24:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.38
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.0597(2)
_cell_length_b                   9.4699(2)
_cell_length_c                   11.8919(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.096(3)
_cell_angle_gamma                90
_cell_volume                     782.72(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.3(3)
_cell_measurement_reflns_used    4725
_cell_measurement_theta_min      3.735
_cell_measurement_theta_max      72.71

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.035
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method 'Crystallization in organic solvent'
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.66043
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_ambient_temperature      150.3(3)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0254735
_diffrn_orient_matrix_ub_12      -0.0273008
_diffrn_orient_matrix_ub_13      -0.1295002
_diffrn_orient_matrix_ub_21      0.1628236
_diffrn_orient_matrix_ub_22      -0.1103025
_diffrn_orient_matrix_ub_23      0.0208343
_diffrn_orient_matrix_ub_31      -0.1481092
_diffrn_orient_matrix_ub_32      -0.1164586
_diffrn_orient_matrix_ub_33      0.0106897
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_number            8452
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.78
_diffrn_reflns_theta_max         68.97
_diffrn_reflns_theta_full        68.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2909
_reflns_number_gt                2667
_reflns_threshold_expression     >2sigma(I)
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -111.00 -20.00   1.00    1.00    --  -42.13 -38.00  90.00   91
  2  ω    -32.00  71.00   1.00    1.00    --   42.13 -77.00 -60.00  103
  3  ω     42.00  67.00   1.00    1.00    --   42.13-125.00-120.00   25
  4  ω     36.00  67.00   1.00    4.00    --  107.93 -45.00 150.00   31
  5  ω     39.00  68.00   1.00    4.00    --  107.93 -30.00  30.00   29
  6  ω     59.00 129.00   1.00    4.00    --  107.93 149.00 -72.00   70
  7  ω     48.00  77.00   1.00    4.00    --  107.93 -45.00 -90.00   29
  8  ω     40.00  69.00   1.00    4.00    --  107.93 -30.00-120.00   29
  9  ω     42.00  69.00   1.00    4.00    --  107.93 -30.00   0.00   27
 10  ω     33.00 139.00   1.00    4.00    --  107.93 -77.00 120.00  106
 11  ω     33.00  60.00   1.00    4.00    --  107.93 -30.00-150.00   27
 12  ω     88.00 151.00   1.00    4.00    --  107.93  45.00-120.00   63
 13  ω     82.00 135.00   1.00    4.00    --  107.93 125.00 -90.00   53
 14  ω   -114.00 -26.00   1.00    1.00    --  -42.13 -38.00-180.00   88
 15  ω      6.00  51.00   1.00    1.00    --   42.13-125.00  90.00   45
 16  ω     55.00  96.00   1.00    1.00    --   42.13-125.00-180.00   41
 17  ω     55.00 118.00   1.00    4.00    --  107.93-125.00 120.00   63
 18  ω    120.00 158.00   1.00    4.00    --  107.93  45.00 -90.00   38
 19  ω     36.00  65.00   1.00    4.00    --  107.93 -30.00  60.00   29
 20  ω     79.00 106.00   1.00    4.00    --  107.93-125.00-120.00   27
 21  ω     37.00  64.00   1.00    4.00    --  107.93 -45.00   0.00   27
 22  ω     45.00  77.00   1.00    4.00    --  107.93 -61.00-120.00   32
 23  ω     99.00 128.00   1.00    4.00    --  107.93 -61.00-120.00   29
 24  ω     77.00 116.00   1.00    4.00    --  107.93-125.00 -30.00   39
 25  ω     44.00  91.00   1.00    4.00    --  107.93-125.00  60.00   47
 26  ω    101.00 149.00   1.00    4.00    --  107.93  77.00-180.00   48
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXH-1997 (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.1947P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2909
_refine_ls_number_parameters     267
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.6498(2) 0.5943(2) 0.87190(15) 0.0369(4) Uani 1 d . .
O002 O -0.0032(2) 0.6688(2) 0.80693(15) 0.0430(5) Uani 1 d . .
H002 H -0.0905 0.6521 0.8449 0.064 Uiso 1 calc . .
C003 C 0.5090(3) 0.6567(2) 0.82096(18) 0.0240(5) Uani 1 d . .
C004 C 0.2599(7) 0.3530(4) 0.6993(4) 0.0144(9) Uani 0.710(10) d A 1
C005 C 0.3125(3) 0.4269(2) 0.81137(18) 0.0246(5) Uani 1 d . .
H005 H 0.4436 0.3955 0.849 0.03 Uiso 0.710(10) calc A 1
H00A H 0.4408 0.4057 0.8588 0.03 Uiso 0.290(10) calc A 2
C006 C 0.1752(3) 0.5305(3) 0.9640(2) 0.0321(5) Uani 1 d . .
H00B H 0.2917 0.5319 1.024 0.039 Uiso 1 calc A .
H00C H 0.06 0.538 1.0006 0.039 Uiso 1 calc . .
C007 C 0.3933(5) 0.2609(3) 0.6520(3) 0.0193(8) Uani 0.710(10) d A 1
C00G C 0.5778(5) 0.2359(4) 0.7117(3) 0.0315(11) Uani 0.710(10) d A 1
H00G H 0.6203 0.2811 0.783 0.038 Uiso 0.710(10) calc A 1
C00M C 0.7002(6) 0.1448(3) 0.6672(4) 0.0376(11) Uani 0.710(10) d A 1
H00M H 0.8263 0.1278 0.708 0.045 Uiso 0.710(10) calc A 1
C00K C 0.6381(7) 0.0787(3) 0.5629(4) 0.0366(12) Uani 0.710(10) d A 1
H00K H 0.7217 0.0164 0.5324 0.044 Uiso 0.710(10) calc A 1
C00L C 0.4536(8) 0.1036(3) 0.5032(3) 0.0391(12) Uani 0.710(10) d A 1
H00L H 0.4112 0.0584 0.4319 0.047 Uiso 0.710(10) calc A 1
C00H C 0.3312(6) 0.1947(3) 0.5477(2) 0.0273(10) Uani 0.710(10) d A 1
C008 C 0.3126(3) 0.5888(2) 0.79714(17) 0.0203(4) Uani 1 d A .
H008 H 0.2526 0.6114 0.7166 0.024 Uiso 1 calc . .
C009 C 0.1802(3) 0.6507(3) 0.87805(18) 0.0256(5) Uani 1 d A .
C00A C 0.3408(4) 0.8895(3) 0.7539(2) 0.0322(5) Uani 1 d . .
H00D H 0.2478 0.8387 0.6959 0.039 Uiso 1 calc . .
H00E H 0.368 0.9816 0.7207 0.039 Uiso 1 calc . .
C00B C 0.5259(3) 0.8051(2) 0.7779(2) 0.0298(5) Uani 1 d . .
H00F H 0.5803 0.8003 0.7067 0.036 Uiso 1 calc . .
H00H H 0.619 0.8571 0.8351 0.036 Uiso 1 calc . .
C00C C 0.2476(4) 0.7887(3) 0.93659(19) 0.0322(5) Uani 1 d . .
H00I H 0.38 0.7751 0.9792 0.039 Uiso 1 calc A .
H00J H 0.1642 0.8105 0.9931 0.039 Uiso 1 calc . .
C00D C 0.1681(4) 0.3974(3) 0.8926(2) 0.0361(6) Uani 1 d A .
H00N H 0.037 0.3812 0.849 0.043 Uiso 1 calc . .
H00O H 0.2078 0.314 0.9412 0.043 Uiso 1 calc . .
C00E C 0.0780(8) 0.3721(5) 0.6358(4) 0.0251(10) Uani 0.710(10) d A 1
H00P H -0.0111 0.4304 0.6655 0.03 Uiso 0.710(10) calc A 1
C00F C 0.2476(4) 0.9164(3) 0.8577(2) 0.0392(6) Uani 1 d A .
H00Q H 0.113 0.9467 0.8314 0.047 Uiso 1 calc . .
H00R H 0.3161 0.9951 0.9022 0.047 Uiso 1 calc . .
C00I C 0.1460(9) 0.2196(5) 0.4846(4) 0.0307(12) Uani 0.710(10) d A 1
H00S H 0.1068 0.1761 0.4123 0.037 Uiso 0.710(10) calc A 1
C00J C 0.0212(8) 0.3084(5) 0.5294(3) 0.0294(11) Uani 0.710(10) d A 1
H00T H -0.1037 0.326 0.4872 0.035 Uiso 0.710(10) calc A 1
C2 C 0.235(2) 0.1881(15) 0.4913(12) 0.047(3) Uani 0.290(10) d A 2
H2 H 0.218 0.1359 0.422 0.056 Uiso 0.290(10) calc A 2
C4 C 0.086(2) 0.2659(15) 0.5131(11) 0.033(3) Uani 0.290(10) d A 2
H4 H -0.0344 0.2691 0.463 0.04 Uiso 0.290(10) calc A 2
C6 C 0.4477(15) 0.2534(10) 0.6652(8) 0.039(3) Uani 0.290(10) d A 2
C16 C 0.6251(15) 0.2375(11) 0.7361(8) 0.030(2) Uani 0.290(10) d A 2
H16 H 0.6523 0.2878 0.8062 0.036 Uiso 0.290(10) calc A 2
C5 C 0.7627(15) 0.1480(10) 0.7044(9) 0.049(3) Uani 0.290(10) d A 2
H5 H 0.884 0.1371 0.7529 0.058 Uiso 0.290(10) calc A 2
C3 C 0.7229(16) 0.0744(8) 0.6018(9) 0.048(3) Uani 0.290(10) d A 2
H3 H 0.8169 0.0133 0.5802 0.057 Uiso 0.290(10) calc A 2
C1 C 0.5455(17) 0.0903(8) 0.5309(7) 0.031(3) Uani 0.290(10) d A 2
H1 H 0.5183 0.04 0.4608 0.038 Uiso 0.290(10) calc A 2
C7 C 0.4079(15) 0.1798(10) 0.5626(8) 0.036(3) Uani 0.290(10) d A 2
C9 C 0.126(2) 0.3464(17) 0.6216(15) 0.044(4) Uani 0.290(10) d A 2
H9 H 0.0331 0.4081 0.6442 0.053 Uiso 0.290(10) calc A 2
C0AA C 0.308(2) 0.3258(17) 0.6890(13) 0.036(4) Uani 0.290(10) d A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
O001 C003 1.222(3) . ?
O002 H002 0.84 . ?
O002 C009 1.428(2) . ?
C003 C008 1.509(3) . ?
C003 C00B 1.507(3) . ?
C004 C005 1.493(5) . ?
C004 C007 1.467(5) . ?
C004 C00E 1.383(7) . ?
C005 H005 1 . ?
C005 H00A 1 . ?
C005 C008 1.543(3) . ?
C005 C00D 1.547(3) . ?
C005 C0AA 1.737(18) . ?
C006 H00B 0.99 . ?
C006 H00C 0.99 . ?
C006 C009 1.534(3) . ?
C006 C00D 1.516(4) . ?
C007 C00G 1.39 . ?
C007 C00H 1.39 . ?
C00G H00G 0.95 . ?
C00G C00M 1.39 . ?
C00M H00M 0.95 . ?
C00M C00K 1.39 . ?
C00K H00K 0.95 . ?
C00K C00L 1.39 . ?
C00L H00L 0.95 . ?
C00L C00H 1.39 . ?
C00H C00I 1.409(5) . ?
C008 H008 1 . ?
C008 C009 1.568(3) . ?
C009 C00C 1.518(3) . ?
C00A H00D 0.99 . ?
C00A H00E 0.99 . ?
C00A C00B 1.516(3) . ?
C00A C00F 1.518(4) . ?
C00B H00F 0.99 . ?
C00B H00H 0.99 . ?
C00C H00I 0.99 . ?
C00C H00J 0.99 . ?
C00C C00F 1.530(3) . ?
C00D H00N 0.99 . ?
C00D H00O 0.99 . ?
C00E H00P 0.95 . ?
C00E C00J 1.396(6) . ?
C00F H00Q 0.99 . ?
C00F H00R 0.99 . ?
C00I H00S 0.95 . ?
C00I C00J 1.390(6) . ?
C00J H00T 0.95 . ?
C2 H2 0.95 . ?
C2 C4 1.343(17) . ?
C2 C7 1.363(15) . ?
C4 H4 0.95 . ?
C4 C9 1.48(2) . ?
C6 C16 1.39 . ?
C6 C7 1.39 . ?
C6 C0AA 1.272(16) . ?
C16 H16 0.95 . ?
C16 C5 1.39 . ?
C5 H5 0.95 . ?
C5 C3 1.39 . ?
C3 H3 0.95 . ?
C3 C1 1.39 . ?
C1 H1 0.95 . ?
C1 C7 1.39 . ?
C9 H9 0.95 . ?
C9 C0AA 1.41(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
C009 O002 H002 109.5 . . ?
O001 C003 C008 121.9(2) . . ?
O001 C003 C00B 120.9(2) . . ?
C00B C003 C008 117.26(19) . . ?
C007 C004 C005 123.0(3) . . ?
C00E C004 C005 119.2(4) . . ?
C00E C004 C007 117.7(4) . . ?
C004 C005 H005 109 . . ?
C004 C005 H00A 117.9 . . ?
C004 C005 C008 111.9(2) . . ?
C004 C005 C00D 112.6(2) . . ?
C004 C005 C0AA 13.9(5) . . ?
H005 C005 H00A 8.9 . . ?
C008 C005 H005 109 . . ?
C008 C005 H00A 104.1 . . ?
C008 C005 C00D 105.14(18) . . ?
C008 C005 C0AA 117.1(5) . . ?
C00D C005 H005 109 . . ?
C00D C005 H00A 104.1 . . ?
C00D C005 C0AA 120.4(5) . . ?
C0AA C005 H005 95.2 . . ?
C0AA C005 H00A 104.1 . . ?
H00B C006 H00C 108.9 . . ?
C009 C006 H00B 110.9 . . ?
C009 C006 H00C 110.9 . . ?
C00D C006 H00B 110.9 . . ?
C00D C006 H00C 110.9 . . ?
C00D C006 C009 104.26(18) . . ?
C00G C007 C004 120.8(2) . . ?
C00G C007 C00H 120 . . ?
C00H C007 C004 119.1(2) . . ?
C007 C00G H00G 120 . . ?
C00M C00G C007 120 . . ?
C00M C00G H00G 120 . . ?
C00G C00M H00M 120 . . ?
C00K C00M C00G 120 . . ?
C00K C00M H00M 120 . . ?
C00M C00K H00K 120 . . ?
C00M C00K C00L 120 . . ?
C00L C00K H00K 120 . . ?
C00K C00L H00L 120 . . ?
C00K C00L C00H 120 . . ?
C00H C00L H00L 120 . . ?
C007 C00H C00I 121.2(3) . . ?
C00L C00H C007 120 . . ?
C00L C00H C00I 118.8(3) . . ?
C003 C008 C005 114.90(17) . . ?
C003 C008 H008 108 . . ?
C003 C008 C009 110.64(17) . . ?
C005 C008 H008 108 . . ?
C005 C008 C009 106.99(17) . . ?
C009 C008 H008 108 . . ?
O002 C009 C006 111.06(18) . . ?
O002 C009 C008 104.95(17) . . ?
O002 C009 C00C 110.31(19) . . ?
C006 C009 C008 102.56(17) . . ?
C00C C009 C006 112.05(18) . . ?
C00C C009 C008 115.51(17) . . ?
H00D C00A H00E 107.6 . . ?
C00B C00A H00D 108.6 . . ?
C00B C00A H00E 108.6 . . ?
C00B C00A C00F 114.7(2) . . ?
C00F C00A H00D 108.6 . . ?
C00F C00A H00E 108.6 . . ?
C003 C00B C00A 116.04(18) . . ?
C003 C00B H00F 108.3 . . ?
C003 C00B H00H 108.3 . . ?
C00A C00B H00F 108.3 . . ?
C00A C00B H00H 108.3 . . ?
H00F C00B H00H 107.4 . . ?
C009 C00C H00I 108.4 . . ?
C009 C00C H00J 108.4 . . ?
C009 C00C C00F 115.66(19) . . ?
H00I C00C H00J 107.4 . . ?
C00F C00C H00I 108.4 . . ?
C00F C00C H00J 108.4 . . ?
C005 C00D H00N 111 . . ?
C005 C00D H00O 111 . . ?
C006 C00D C005 103.81(18) . . ?
C006 C00D H00N 111 . . ?
C006 C00D H00O 111 . . ?
H00N C00D H00O 109 . . ?
C004 C00E H00P 119 . . ?
C004 C00E C00J 122.0(5) . . ?
C00J C00E H00P 119 . . ?
C00A C00F C00C 114.4(2) . . ?
C00A C00F H00Q 108.7 . . ?
C00A C00F H00R 108.7 . . ?
C00C C00F H00Q 108.7 . . ?
C00C C00F H00R 108.7 . . ?
H00Q C00F H00R 107.6 . . ?
C00H C00I H00S 120.4 . . ?
C00J C00I C00H 119.3(4) . . ?
C00J C00I H00S 120.4 . . ?
C00E C00J H00T 119.7 . . ?
C00I C00J C00E 120.5(4) . . ?
C00I C00J H00T 119.7 . . ?
C4 C2 H2 118.1 . . ?
C4 C2 C7 123.9(12) . . ?
C7 C2 H2 118.1 . . ?
C2 C4 H4 122.7 . . ?
C2 C4 C9 114.6(11) . . ?
C9 C4 H4 122.7 . . ?
C16 C6 C7 120 . . ?
C0AA C6 C16 125.0(9) . . ?
C0AA C6 C7 114.9(9) . . ?
C6 C16 H16 120 . . ?
C5 C16 C6 120 . . ?
C5 C16 H16 120 . . ?
C16 C5 H5 120 . . ?
C16 C5 C3 120 . . ?
C3 C5 H5 120 . . ?
C5 C3 H3 120 . . ?
C1 C3 C5 120 . . ?
C1 C3 H3 120 . . ?
C3 C1 H1 120 . . ?
C3 C1 C7 120 . . ?
C7 C1 H1 120 . . ?
C2 C7 C6 122.6(8) . . ?
C2 C7 C1 117.4(8) . . ?
C1 C7 C6 120 . . ?
C4 C9 H9 122 . . ?
C0AA C9 C4 116.0(13) . . ?
C0AA C9 H9 122 . . ?
C6 C0AA C005 125.7(10) . . ?
C6 C0AA C9 127.9(14) . . ?
C9 C0AA C005 106.3(12) . . ?

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
O001 C003 C008 C005 -15.9(3) . . . . ?
O001 C003 C008 C009 105.4(2) . . . . ?
O001 C003 C00B C00A -159.6(2) . . . . ?
O002 C009 C00C C00F -52.8(3) . . . . ?
C003 C008 C009 O002 138.49(19) . . . . ?
C003 C008 C009 C006 -105.4(2) . . . . ?
C003 C008 C009 C00C 16.8(2) . . . . ?
C004 C005 C008 C003 -109.9(3) . . . . ?
C004 C005 C008 C009 126.9(3) . . . . ?
C004 C005 C00D C006 -150.0(3) . . . . ?
C004 C005 C0AA C6 180(4) . . . . ?
C004 C005 C0AA C9 2.2(19) . . . . ?
C004 C007 C00G C00M 178.0(3) . . . . ?
C004 C007 C00H C00L -178.1(3) . . . . ?
C004 C007 C00H C00I 2.9(4) . . . . ?
C004 C00E C00J C00I 1.7(7) . . . . ?
C005 C004 C007 C00G 1.1(5) . . . . ?
C005 C004 C007 C00H 179.1(3) . . . . ?
C005 C004 C00E C00J 178.7(4) . . . . ?
C005 C008 C009 O002 -95.66(19) . . . . ?
C005 C008 C009 C006 20.5(2) . . . . ?
C005 C008 C009 C00C 142.64(19) . . . . ?
C006 C009 C00C C00F -177.09(19) . . . . ?
C007 C004 C005 C008 115.4(4) . . . . ?
C007 C004 C005 C00D -126.5(3) . . . . ?
C007 C004 C005 C0AA 0(2) . . . . ?
C007 C004 C00E C00J -0.9(7) . . . . ?
C007 C00G C00M C00K 0 . . . . ?
C007 C00H C00I C00J -2.1(5) . . . . ?
C00G C007 C00H C00L 0 . . . . ?
C00G C007 C00H C00I -179.1(3) . . . . ?
C00G C00M C00K C00L 0 . . . . ?
C00M C00K C00L C00H 0 . . . . ?
C00K C00L C00H C007 0 . . . . ?
C00K C00L C00H C00I 179.1(3) . . . . ?
C00L C00H C00I C00J 178.8(3) . . . . ?
C00H C007 C00G C00M 0 . . . . ?
C00H C00I C00J C00E -0.2(6) . . . . ?
C008 C003 C00B C00A 21.2(3) . . . . ?
C008 C005 C00D C006 -27.9(2) . . . . ?
C008 C005 C0AA C6 108.5(13) . . . . ?
C008 C005 C0AA C9 -68.8(11) . . . . ?
C008 C009 C00C C00F 66.0(2) . . . . ?
C009 C006 C00D C005 41.7(2) . . . . ?
C009 C00C C00F C00A -48.0(3) . . . . ?
C00B C003 C008 C005 163.38(19) . . . . ?
C00B C003 C008 C009 -75.3(2) . . . . ?
C00B C00A C00F C00C -42.3(3) . . . . ?
C00D C005 C008 C003 127.56(19) . . . . ?
C00D C005 C008 C009 4.3(2) . . . . ?
C00D C005 C0AA C6 -121.6(13) . . . . ?
C00D C005 C0AA C9 61.1(12) . . . . ?
C00D C006 C009 O002 73.4(2) . . . . ?
C00D C006 C009 C008 -38.2(2) . . . . ?
C00D C006 C009 C00C -162.70(19) . . . . ?
C00E C004 C005 C008 -64.1(4) . . . . ?
C00E C004 C005 C00D 54.0(4) . . . . ?
C00E C004 C005 C0AA -179(3) . . . . ?
C00E C004 C007 C00G -179.4(3) . . . . ?
C00E C004 C007 C00H -1.4(5) . . . . ?
C00F C00A C00B C003 62.7(3) . . . . ?
C2 C4 C9 C0AA -2.8(19) . . . . ?
C4 C2 C7 C6 -0.8(16) . . . . ?
C4 C2 C7 C1 177.4(10) . . . . ?
C4 C9 C0AA C005 -178.1(11) . . . . ?
C4 C9 C0AA C6 5(2) . . . . ?
C6 C16 C5 C3 0 . . . . ?
C16 C6 C7 C2 178.1(10) . . . . ?
C16 C6 C7 C1 0 . . . . ?
C16 C6 C0AA C005 3.3(19) . . . . ?
C16 C6 C0AA C9 -180.0(12) . . . . ?
C16 C5 C3 C1 0 . . . . ?
C5 C3 C1 C7 0 . . . . ?
C3 C1 C7 C2 -178.2(10) . . . . ?
C3 C1 C7 C6 0 . . . . ?
C7 C2 C4 C9 1.2(19) . . . . ?
C7 C6 C16 C5 0 . . . . ?
C7 C6 C0AA C005 179.2(8) . . . . ?
C7 C6 C0AA C9 -4(2) . . . . ?
C0AA C005 C008 C003 -95.7(6) . . . . ?
C0AA C005 C008 C009 141.1(6) . . . . ?
C0AA C005 C00D C006 -162.9(6) . . . . ?
C0AA C6 C16 C5 175.7(13) . . . . ?
C0AA C6 C7 C2 2.0(12) . . . . ?
C0AA C6 C7 C1 -176.1(12) . . . . ?





# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
