# 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_cu_ca210516_1_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1517154'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,-z
_cell_length_a                   12.6297(2)
_cell_length_b                   11.1898(2)
_cell_length_c                   14.5794(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.0660(10)
_cell_angle_gamma                90
_cell_volume                     2048.88
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O3A O 0.8141(3) 0.7117(4) 1.0730(3)
O2A O 0.8726(4) 0.6326(6) 1.2122(3)
N1A N 0.6937(4) 0.6578(5) 1.1673(3)
O1A O 0.5672(4) 0.5942(7) 1.2543(3)
C3A C 0.8022(5) 0.6660(6) 1.1550(4)
C13A C 0.6065(5) 0.5949(5) 1.0165(4)
H13A H 0.6598 0.5357 1.0127
C4A C 0.9209(4) 0.7111(6) 1.0382(4)
C12A C 0.5225(4) 0.6038(5) 0.9471(4)
H12A H 0.5189 0.5505 0.8961
O5A O 0.2157(5) 0.6081(9) 0.9643(5)
C8A C 0.6125(4) 0.6721(6) 1.0912(4)
C11A C 0.4437(4) 0.6897(6) 0.9513(4)
C14A C 0.3498(5) 0.6979(7) 0.8775(5)
C19A C 0.3136(5) 0.5512(7) 0.7554(5)
O4A O 0.2256(5) 0.8457(8) 0.9424(5)
H4A H 0.1802 0.7909 0.9432
C10A C 0.4514(5) 0.7661(7) 1.0285(5)
H10A H 0.3979 0.8247 1.0335
C18A C 0.3722(5) 0.6658(7) 0.7796(5)
H18A H 0.4503 0.6565 0.7755
C9A C 0.5345(5) 0.7575(7) 1.0963(5)
H9A H 0.5385 0.8107 1.1473
C21A C 0.2668(5) 0.6057(8) 0.8966(6)
C7A C 0.9968(6) 0.7900(8) 1.0982(5)
H7AA H 0.9659 0.8700 1.1020
H7AB H 1.0646 0.7957 1.0714
H7AC H 1.0091 0.7556 1.1602
C6A C 0.9591(6) 0.5845(7) 1.0326(7)
H6AA H 0.9840 0.5557 1.0947
H6AB H 1.0178 0.5812 0.9938
H6AC H 0.9005 0.5339 1.0059
C5A C 0.8963(5) 0.7668(9) 0.9447(5)
H5AA H 0.8486 0.7142 0.9057
H5AB H 0.9626 0.7782 0.9163
H5AC H 0.8617 0.8443 0.9510
C20A C 0.2573(6) 0.5190(8) 0.8226(7)
H20A H 0.2159 0.4481 0.8224
C22A C 0.3193(7) 0.4925(11) 0.6642(7)
H22G H 0.2907 0.5467 0.6148
H22H H 0.2773 0.4187 0.6612
H22I H 0.3936 0.4736 0.6566
C2A C 0.6592(6) 0.6229(9) 1.2529(5)
C17A C 0.3256(8) 0.7736(9) 0.7194(6)
H17E H 0.3808 0.8348 0.7128
H17F H 0.2959 0.7465 0.6573
C1A C 0.7348(8) 0.6279(14) 1.3408(5)
H1AA H 0.7867 0.5629 1.3407
H1AB H 0.6943 0.6193 1.3942
H1AC H 0.7722 0.7048 1.3443
C15A C 0.2935(6) 0.8214(9) 0.8720(6)
H15A H 0.3500 0.8843 0.8759
C16A C 0.2379(7) 0.8222(9) 0.7740(7)
H16E H 0.2165 0.9040 0.7541
H16F H 0.1745 0.7696 0.7681
O1B O 0.5699(4) 0.4408(5) 0.7451(3)
C2B C 0.6578(6) 0.4108(7) 0.7286(5)
O5B O 0.2795(9) 0.1536(9) 0.3577(8)
N1B N 0.6666(10) 0.3552(11) 0.6429(7)
C11B C 0.4119(5) 0.3746(5) 0.4345(4)
C19B C 0.3546(10) 0.3647(15) 0.2017(8)
C8B C 0.5820(5) 0.3739(5) 0.5728(4)
C21B C 0.3158(15) 0.2444(14) 0.3171(12)
O4B O 0.1766(13) 0.3207(12) 0.4578(9)
H4B H 0.1757 0.2540 0.4313
C14B C 0.3194(7) 0.3740(7) 0.3607(5)
O3B O 0.8363(8) 0.3641(10) 0.6308(7)
C16B C 0.147(2) 0.446(4) 0.314(3)
H16A H 0.0872 0.4976 0.3283
H16B H 0.1178 0.3760 0.2777
O2B O 0.7399(7) 0.2377(8) 0.5360(6)
C15B C 0.2163(15) 0.4072(17) 0.4016(15)
H15B H 0.2315 0.4803 0.4402
C18B C 0.3361(14) 0.4534(13) 0.2755(9)
H18B H 0.3966 0.5108 0.2882
C20B C 0.3411(9) 0.2509(13) 0.2272(9)
H20B H 0.3480 0.1836 0.1885
C1B C 0.7506(8) 0.4084(12) 0.7985(7)
H1BA H 0.8036 0.4663 0.7820
H1BB H 0.7819 0.3281 0.8013
H1BC H 0.7282 0.4291 0.8589
C17B C 0.2273(15) 0.5169(17) 0.2600(12)
H17A H 0.2021 0.5190 0.1934
H17B H 0.2337 0.6002 0.2829
C3B C 0.7515(10) 0.3118(12) 0.5948(7)
C10B C 0.4027(8) 0.2962(7) 0.5061(5)
H10B H 0.3422 0.2468 0.5103
C12B C 0.4921(7) 0.4568(7) 0.4281(6)
H12B H 0.4920 0.5124 0.3788
C7B C 0.9753(8) 0.2250(12) 0.5848(9)
H7BA H 0.9833 0.2026 0.6501
H7BB H 1.0447 0.2207 0.5605
H7BC H 0.9255 0.1700 0.5502
C4B C 0.9324(9) 0.3516(11) 0.5746(10)
C13B C 0.5717(7) 0.4510(8) 0.4988(6)
H13B H 0.6274 0.5077 0.4968
C9B C 0.4904(7) 0.2971(8) 0.5713(6)
H9B H 0.4903 0.2411 0.6203
C22B C 0.3780(11) 0.4118(16) 0.1127(8)
H22A H 0.3194 0.4633 0.0872
H22B H 0.3863 0.3454 0.0702
H22C H 0.4441 0.4583 0.1209
C5B C 1.0134(13) 0.4322(16) 0.6337(13)
H5BA H 0.9829 0.5121 0.6392
H5BB H 1.0793 0.4382 0.6041
H5BC H 1.0290 0.3972 0.6953
C6B C 0.9102(11) 0.3935(18) 0.4797(11)
H6BA H 0.8818 0.3274 0.4404
H6BB H 0.9761 0.4229 0.4577
H6BC H 0.8578 0.4583 0.4773
N1C N 0.6817(12) 0.3970(15) 0.6376(11)
C3C C 0.7880(17) 0.393(2) 0.607(2)
O3C O 0.8599(13) 0.447(2) 0.6578(19)
O2C O 0.8016(11) 0.3492(12) 0.5431(14)
C6C C 1.007(2) 0.325(2) 0.618(2)
H6CA H 1.0285 0.3024 0.6822
H6CB H 1.0691 0.3222 0.5830
H6CC H 0.9523 0.2703 0.5908
C4C C 0.9627(18) 0.452(2) 0.6154(17)
C5C C 0.9615(17) 0.504(2) 0.5215(16)
H5CA H 0.9073 0.5667 0.5132
H5CB H 0.9448 0.4410 0.4754
H5CC H 1.0315 0.5379 0.5140
C7C C 1.019(2) 0.530(3) 0.6894(18)
H7CA H 0.9744 0.6002 0.6990
H7CB H 1.0871 0.5569 0.6704
H7CC H 1.0312 0.4850 0.7470
C13C C 0.5434(10) 0.4868(7) 0.5450(8)
H13C H 0.5697 0.5604 0.5707
C12C C 0.4621(10) 0.4758(8) 0.4751(9)
H12C H 0.4353 0.5496 0.4501
C10C C 0.4690(10) 0.2729(8) 0.4710(8)
H10C H 0.4445 0.1990 0.4446
C9C C 0.5534(10) 0.2631(8) 0.5381(9)
H9C H 0.5872 0.1902 0.5577
C18C C 0.310(2) 0.4864(18) 0.2865(13)
H18C H 0.3631 0.5494 0.3067
C17C C 0.197(2) 0.540(3) 0.276(2)
H17C H 0.1760 0.5670 0.2117
H17D H 0.1915 0.6088 0.3182
C21C C 0.319(2) 0.277(2) 0.2866(15)
C20C C 0.3397(16) 0.310(2) 0.2007(13)
H20C H 0.3534 0.2570 0.1523
C19C C 0.3379(15) 0.4273(19) 0.1957(12)
C22C C 0.3563(17) 0.490(2) 0.1077(12)
H22D H 0.3158 0.5645 0.1028
H22E H 0.3329 0.4382 0.0551
H22F H 0.4324 0.5072 0.1078
O5C O 0.2990(14) 0.1765(16) 0.3191(12)
C16C C 0.127(3) 0.433(5) 0.302(4)
H16C H 0.0580 0.4597 0.3212
H16D H 0.1153 0.3740 0.2518
C15C C 0.202(2) 0.386(3) 0.384(3)
H15C H 0.2025 0.4480 0.4330
O4C O 0.162(2) 0.2824(18) 0.4203(14)
H4C H 0.1643 0.2261 0.3824

#END
_chemical_name_systematic        
'tert-butyl acetyl(4-((3R,3aR,6aR)-3-hydroxy-6-methyl-4-oxo-2,3,4,6a-tetrahydropentalen-3a(1H)-yl)phenyl)carbamate'
_exptl_crystal_colour            'clear colourless'
_chemical_formula_moiety         C22H27NO5
_chemical_formula_sum            C22H27NO5
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylene chloride'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_cu_ca220516_1_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1517155'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_audit_creation_date             2016-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
(3aR,6R,6aR)-6a-(4-fluorophenyl)-6-hydroxy-3-methyl-4,5,6,6a-tetrahydropentalen-1(3aH)-one
_chemical_formula_moiety         'C15 H15 F O2'
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.27
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4982(2)
_cell_length_b                   8.0473(2)
_cell_length_c                   20.6908(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.071(2)
_cell_angle_gamma                90
_cell_volume                     1232.87(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9358
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      66.63
_cell_measurement_theta_min      4.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0643 before and 0.0396 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25303
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.639
_diffrn_reflns_theta_max         66.639
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Apex2 Duo (Cu)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                4278
_reflns_number_total             4301
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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         0.205
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4301
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.4009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0774
_refine_special_details          
;
Other enantiomer cocrystallized (about 12%) on
the same position, observed as disorder of the
hydroxy groups.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1C-C14B = O1D-C14A
 1.4 with sigma of 0.02
 O1C-C14B \\sim O1B-C14B
 with sigma of 0.02
 O1D-C14A \\sim O1A-C14A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O1A, C14A, O1D, O1B, O1C, C14B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H14B)=Sof(H14D)=Sof(O1C)=Sof(H1C)=Sof(O1D)=Sof(H1D)=1-FVAR(1)
 Sof(O1A)=Sof(H1A)=Sof(O1B)=Sof(H1B)=Sof(H14A)=Sof(H14C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11A(H11A), C11B(H11B), C14A(H14A), C14A(H14B), C14B(H14C), C14B(H14D)
5.b Secondary CH2 refined with riding coordinates:
 C12B(H12C,H12D), C12A(H12A,H12B), C13A(H13A,H13B), C13B(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 C1A(H1AA), C9A(H9A), C2A(H2A), C5A(H5A), C4B(H4B), C4A(H4A), C1B(H1BA),
 C5B(H5B), C9B(H9B), C2B(H2B)
5.d Idealised Me refined as rotating group:
 C15A(H15A,H15B,H15C), C15B(H15D,H15E,H15F)
5.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B), O1C(H1C), O1D(H1D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.3, Nqual =  -1, Ralpha = 0.131
;
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
F1A F 1.01905(19) 1.01832(18) 0.89932(7) 0.0314(3) Uani 1 1 d . . . . .
F1B F 1.2938(2) -0.1498(2) 0.73064(8) 0.0373(4) Uani 1 1 d . . . . .
O2A O 0.6680(2) 0.3095(2) 0.80349(8) 0.0225(4) Uani 1 1 d . . . . .
O2B O 1.0632(2) 0.4489(2) 0.53724(8) 0.0263(4) Uani 1 1 d . . . . .
O1A O 0.7188(2) 0.2417(2) 0.93897(8) 0.0195(5) Uani 0.877(4) 1 d D U P A 1
H1A H 0.7342 0.2235 0.9003 0.029 Uiso 0.877(4) 1 calc GR . P A 1
O1B O 0.7455(3) 0.2357(3) 0.48194(9) 0.0245(5) Uani 0.877(4) 1 d D U P A 1
H1B H 0.8094 0.3173 0.4748 0.037 Uiso 0.877(4) 1 calc GR . P A 1
C1A C 0.8303(3) 0.6184(3) 0.93185(11) 0.0189(4) Uani 1 1 d . . . . .
H1AA H 0.8606 0.5239 0.9589 0.023 Uiso 1 1 calc R . . . .
C6A C 0.6676(3) 0.6207(3) 0.88841(11) 0.0170(4) Uani 1 1 d . . . . .
C10A C 0.2527(3) 0.4971(3) 0.80832(11) 0.0182(5) Uani 1 1 d . . . . .
C8A C 0.5389(3) 0.3895(3) 0.81644(10) 0.0174(4) Uani 1 1 d . . . . .
C8B C 0.9411(3) 0.4749(3) 0.56935(11) 0.0197(5) Uani 1 1 d . . . . .
C11A C 0.3337(3) 0.5262(3) 0.87890(10) 0.0177(5) Uani 1 1 d . . . . .
H11A H 0.3213 0.6449 0.8918 0.021 Uiso 1 1 calc R . . . .
C11B C 0.7084(3) 0.4416(3) 0.63738(11) 0.0180(5) Uani 1 1 d . . . . .
H11B H 0.7358 0.4166 0.6853 0.022 Uiso 1 1 calc R . . . .
C6B C 0.9583(3) 0.2122(3) 0.63656(11) 0.0169(4) Uani 1 1 d . . . . .
C3A C 0.9038(3) 0.8859(3) 0.89574(12) 0.0229(5) Uani 1 1 d . . . . .
C7A C 0.5357(3) 0.4758(3) 0.88290(10) 0.0160(4) Uani 1 1 d . . . . .
C9A C 0.3669(3) 0.4177(3) 0.77516(11) 0.0201(5) Uani 1 1 d . . . . .
H9A H 0.3388 0.3844 0.7307 0.024 Uiso 1 1 calc R . . . .
C2A C 0.9491(3) 0.7529(3) 0.93612(11) 0.0211(5) Uani 1 1 d . . . . .
H2A H 1.0585 0.7521 0.9663 0.025 Uiso 1 1 calc R . . . .
C5A C 0.6291(3) 0.7590(3) 0.84781(11) 0.0214(5) Uani 1 1 d . . . . .
H5A H 0.5201 0.7612 0.8174 0.026 Uiso 1 1 calc R . . . .
C10B C 0.7491(3) 0.6207(3) 0.62409(11) 0.0210(5) Uani 1 1 d . . . . .
C3B C 1.1831(3) -0.0300(3) 0.69964(12) 0.0240(5) Uani 1 1 d . . . . .
C4B C 1.1973(3) 0.0080(3) 0.63600(12) 0.0263(5) Uani 1 1 d . . . . .
H4B H 1.2815 -0.0479 0.6139 0.032 Uiso 1 1 calc R . . . .
C4A C 0.7463(3) 0.8932(3) 0.85082(12) 0.0232(5) Uani 1 1 d . . . . .
H4A H 0.7194 0.9868 0.8230 0.028 Uiso 1 1 calc R . . . .
C14A C 0.5681(3) 0.3475(3) 0.93888(11) 0.0212(5) Uani 1 1 d D U . . .
H14A H 0.5878 0.4108 0.9810 0.025 Uiso 0.877(4) 1 calc R . P A 1
H14B H 0.6558 0.2639 0.9268 0.025 Uiso 0.123(4) 1 calc R . P A 2
C7B C 0.8333(3) 0.3398(3) 0.59875(10) 0.0166(4) Uani 1 1 d . . . . .
C1B C 0.9473(3) 0.1665(3) 0.70063(12) 0.0219(5) Uani 1 1 d . . . . .
H1BA H 0.8608 0.2187 0.7228 0.026 Uiso 1 1 calc R . . . .
C14B C 0.6951(3) 0.2520(3) 0.54307(11) 0.0236(5) Uani 1 1 d D U . . .
H14C H 0.6701 0.1381 0.5589 0.028 Uiso 0.877(4) 1 calc R . P A 1
H14D H 0.7420 0.2807 0.5018 0.028 Uiso 0.123(4) 1 calc R . P A 2
C5B C 1.0845(3) 0.1311(3) 0.60482(11) 0.0228(5) Uani 1 1 d . . . . .
H5B H 1.0937 0.1606 0.5610 0.027 Uiso 1 1 calc R . . . .
C12B C 0.5128(3) 0.3928(3) 0.60933(13) 0.0268(5) Uani 1 1 d . . . . .
H12C H 0.4734 0.2950 0.6325 0.032 Uiso 1 1 calc R . . . .
H12D H 0.4287 0.4861 0.6127 0.032 Uiso 1 1 calc R . . . .
C9B C 0.8765(3) 0.6372(3) 0.58618(12) 0.0242(5) Uani 1 1 d . . . . .
H9B H 0.9189 0.7403 0.5722 0.029 Uiso 1 1 calc R . . . .
C12A C 0.2545(3) 0.4063(3) 0.92600(12) 0.0254(5) Uani 1 1 d . . . . .
H12A H 0.2491 0.4606 0.9686 0.030 Uiso 1 1 calc R . . . .
H12B H 0.1317 0.3693 0.9067 0.030 Uiso 1 1 calc R . . . .
C2B C 1.0614(3) 0.0453(3) 0.73282(12) 0.0265(5) Uani 1 1 d . . . . .
H2B H 1.0546 0.0158 0.7768 0.032 Uiso 1 1 calc R . . . .
C13A C 0.3859(3) 0.2607(3) 0.93417(13) 0.0264(5) Uani 1 1 d . . . . .
H13A H 0.3645 0.1851 0.8960 0.032 Uiso 1 1 calc R . . . .
H13B H 0.3769 0.1969 0.9744 0.032 Uiso 1 1 calc R . . . .
C15A C 0.0639(3) 0.5500(3) 0.78344(12) 0.0249(5) Uani 1 1 d . . . . .
H15A H -0.0201 0.4853 0.8053 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.0373 0.5310 0.7361 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.0502 0.6684 0.7926 0.037 Uiso 1 1 calc GR . . . .
C13B C 0.5223(3) 0.3524(4) 0.53877(13) 0.0307(6) Uani 1 1 d . . . . .
H13C H 0.5288 0.4548 0.5128 0.037 Uiso 1 1 calc R . . . .
H13D H 0.4163 0.2863 0.5189 0.037 Uiso 1 1 calc R . . . .
C15B C 0.6516(4) 0.7577(4) 0.65215(14) 0.0336(6) Uani 1 1 d . . . . .
H15D H 0.5253 0.7594 0.6308 0.050 Uiso 1 1 calc GR . . . .
H15E H 0.7088 0.8641 0.6449 0.050 Uiso 1 1 calc GR . . . .
H15F H 0.6567 0.7396 0.6992 0.050 Uiso 1 1 calc GR . . . .
O1C O 0.7021(16) 0.0937(13) 0.5450(6) 0.020(3) Uani 0.123(4) 1 d D U P A 2
H1C H 0.7701 0.0596 0.5192 0.029 Uiso 0.123(4) 1 calc GR . P A 2
O1D O 0.608(3) 0.372(3) 1.0008(7) 0.055(6) Uani 0.123(4) 1 d D U P A 2
H1D H 0.5135 0.3909 1.0165 0.083 Uiso 0.123(4) 1 calc GR . P A 2


_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
F1A C3A 1.367(3) . ?
F1B C3B 1.364(3) . ?
O2A C8A 1.227(3) . ?
O2B C8B 1.231(3) . ?
O1A H1A 0.8400 . ?
O1A C14A 1.415(3) . ?
O1B H1B 0.8400 . ?
O1B C14B 1.382(3) . ?
C1A H1AA 0.9500 . ?
C1A C6A 1.397(3) . ?
C1A C2A 1.395(3) . ?
C6A C7A 1.522(3) . ?
C6A C5A 1.397(3) . ?
C10A C11A 1.509(3) . ?
C10A C9A 1.341(3) . ?
C10A C15A 1.490(3) . ?
C8A C7A 1.544(3) . ?
C8A C9A 1.448(3) . ?
C8B C7B 1.537(3) . ?
C8B C9B 1.454(3) . ?
C11A H11A 1.0000 . ?
C11A C7A 1.557(3) . ?
C11A C12A 1.554(3) . ?
C11B H11B 1.0000 . ?
C11B C10B 1.508(3) . ?
C11B C7B 1.557(3) . ?
C11B C12B 1.541(3) . ?
C6B C7B 1.521(3) . ?
C6B C1B 1.391(3) . ?
C6B C5B 1.396(3) . ?
C3A C2A 1.367(4) . ?
C3A C4A 1.384(3) . ?
C7A C14A 1.542(3) . ?
C9A H9A 0.9500 . ?
C2A H2A 0.9500 . ?
C5A H5A 0.9500 . ?
C5A C4A 1.388(3) . ?
C10B C9B 1.335(3) . ?
C10B C15B 1.490(3) . ?
C3B C4B 1.372(3) . ?
C3B C2B 1.368(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.393(3) . ?
C4A H4A 0.9500 . ?
C14A H14A 1.0000 . ?
C14A H14B 1.0000 . ?
C14A C13A 1.523(3) . ?
C14A O1D 1.284(13) . ?
C7B C14B 1.589(3) . ?
C1B H1BA 0.9500 . ?
C1B C2B 1.395(4) . ?
C14B H14C 1.0000 . ?
C14B H14D 1.0000 . ?
C14B C13B 1.518(3) . ?
C14B O1C 1.275(11) . ?
C5B H5B 0.9500 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C12B C13B 1.508(4) . ?
C9B H9B 0.9500 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C12A C13A 1.523(3) . ?
C2B H2B 0.9500 . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
O1C H1C 0.8400 . ?
O1D H1D 0.8400 . ?

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
C14A O1A H1A 109.5 . . ?
C14B O1B H1B 109.5 . . ?
C6A C1A H1AA 119.5 . . ?
C2A C1A H1AA 119.5 . . ?
C2A C1A C6A 121.0(2) . . ?
C1A C6A C7A 122.0(2) . . ?
C1A C6A C5A 118.3(2) . . ?
C5A C6A C7A 119.68(19) . . ?
C9A C10A C11A 112.13(19) . . ?
C9A C10A C15A 127.4(2) . . ?
C15A C10A C11A 120.40(19) . . ?
O2A C8A C7A 123.7(2) . . ?
O2A C8A C9A 127.8(2) . . ?
C9A C8A C7A 108.50(18) . . ?
O2B C8B C7B 125.1(2) . . ?
O2B C8B C9B 125.9(2) . . ?
C9B C8B C7B 108.94(18) . . ?
C10A C11A H11A 111.4 . . ?
C10A C11A C7A 104.54(17) . . ?
C10A C11A C12A 112.05(19) . . ?
C7A C11A H11A 111.4 . . ?
C12A C11A H11A 111.4 . . ?
C12A C11A C7A 105.66(18) . . ?
C10B C11B H11B 110.9 . . ?
C10B C11B C7B 104.72(17) . . ?
C10B C11B C12B 112.52(19) . . ?
C7B C11B H11B 110.9 . . ?
C12B C11B H11B 110.9 . . ?
C12B C11B C7B 106.66(18) . . ?
C1B C6B C7B 123.0(2) . . ?
C1B C6B C5B 118.1(2) . . ?
C5B C6B C7B 118.81(19) . . ?
F1A C3A C2A 118.9(2) . . ?
F1A C3A C4A 118.0(2) . . ?
C2A C3A C4A 123.1(2) . . ?
C6A C7A C8A 108.05(17) . . ?
C6A C7A C11A 114.84(18) . . ?
C6A C7A C14A 115.68(18) . . ?
C8A C7A C11A 102.79(17) . . ?
C14A C7A C8A 110.18(18) . . ?
C14A C7A C11A 104.52(17) . . ?
C10A C9A C8A 110.7(2) . . ?
C10A C9A H9A 124.6 . . ?
C8A C9A H9A 124.6 . . ?
C1A C2A H2A 120.8 . . ?
C3A C2A C1A 118.3(2) . . ?
C3A C2A H2A 120.8 . . ?
C6A C5A H5A 119.2 . . ?
C4A C5A C6A 121.6(2) . . ?
C4A C5A H5A 119.2 . . ?
C9B C10B C11B 112.7(2) . . ?
C9B C10B C15B 126.6(2) . . ?
C15B C10B C11B 120.7(2) . . ?
F1B C3B C4B 118.4(2) . . ?
F1B C3B C2B 118.8(2) . . ?
C2B C3B C4B 122.8(2) . . ?
C3B C4B H4B 121.0 . . ?
C3B C4B C5B 118.0(2) . . ?
C5B C4B H4B 121.0 . . ?
C3A C4A C5A 117.7(2) . . ?
C3A C4A H4A 121.2 . . ?
C5A C4A H4A 121.2 . . ?
O1A C14A C7A 115.79(19) . . ?
O1A C14A H14A 107.3 . . ?
O1A C14A C13A 115.6(2) . . ?
C7A C14A H14A 107.3 . . ?
C7A C14A H14B 107.1 . . ?
C13A C14A C7A 103.03(18) . . ?
C13A C14A H14A 107.3 . . ?
C13A C14A H14B 107.1 . . ?
O1D C14A C7A 129.0(11) . . ?
O1D C14A H14B 107.1 . . ?
O1D C14A C13A 101.7(10) . . ?
C8B C7B C11B 103.15(18) . . ?
C8B C7B C14B 110.58(18) . . ?
C11B C7B C14B 103.29(17) . . ?
C6B C7B C8B 111.18(17) . . ?
C6B C7B C11B 117.58(18) . . ?
C6B C7B C14B 110.57(18) . . ?
C6B C1B H1BA 119.5 . . ?
C6B C1B C2B 121.1(2) . . ?
C2B C1B H1BA 119.5 . . ?
O1B C14B C7B 117.7(2) . . ?
O1B C14B H14C 107.7 . . ?
O1B C14B C13B 110.5(2) . . ?
C7B C14B H14C 107.7 . . ?
C7B C14B H14D 103.8 . . ?
C13B C14B C7B 105.01(19) . . ?
C13B C14B H14C 107.7 . . ?
C13B C14B H14D 103.8 . . ?
O1C C14B C7B 113.8(6) . . ?
O1C C14B H14D 103.8 . . ?
O1C C14B C13B 124.3(6) . . ?
C6B C5B H5B 119.3 . . ?
C4B C5B C6B 121.4(2) . . ?
C4B C5B H5B 119.3 . . ?
C11B C12B H12C 111.1 . . ?
C11B C12B H12D 111.1 . . ?
H12C C12B H12D 109.0 . . ?
C13B C12B C11B 103.43(19) . . ?
C13B C12B H12C 111.1 . . ?
C13B C12B H12D 111.1 . . ?
C8B C9B H9B 124.8 . . ?
C10B C9B C8B 110.4(2) . . ?
C10B C9B H9B 124.8 . . ?
C11A C12A H12A 110.9 . . ?
C11A C12A H12B 110.9 . . ?
H12A C12A H12B 109.0 . . ?
C13A C12A C11A 104.04(18) . . ?
C13A C12A H12A 110.9 . . ?
C13A C12A H12B 110.9 . . ?
C3B C2B C1B 118.5(2) . . ?
C3B C2B H2B 120.7 . . ?
C1B C2B H2B 120.7 . . ?
C14A C13A H13A 111.3 . . ?
C14A C13A H13B 111.3 . . ?
C12A C13A C14A 102.2(2) . . ?
C12A C13A H13A 111.3 . . ?
C12A C13A H13B 111.3 . . ?
H13A C13A H13B 109.2 . . ?
C10A C15A H15A 109.5 . . ?
C10A C15A H15B 109.5 . . ?
C10A C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C14B C13B H13C 111.1 . . ?
C14B C13B H13D 111.1 . . ?
C12B C13B C14B 103.19(19) . . ?
C12B C13B H13C 111.1 . . ?
C12B C13B H13D 111.1 . . ?
H13C C13B H13D 109.1 . . ?
C10B C15B H15D 109.5 . . ?
C10B C15B H15E 109.5 . . ?
C10B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C14B O1C H1C 109.5 . . ?
C14A O1D H1D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1A C3A C2A C1A -179.87(19) . . . . ?
F1A C3A C4A C5A -179.4(2) . . . . ?
F1B C3B C4B C5B -179.7(2) . . . . ?
F1B C3B C2B C1B -179.4(2) . . . . ?
O2A C8A C7A C6A 69.3(3) . . . . ?
O2A C8A C7A C11A -168.9(2) . . . . ?
O2A C8A C7A C14A -57.9(3) . . . . ?
O2A C8A C9A C10A 173.8(2) . . . . ?
O2B C8B C7B C11B 176.4(2) . . . . ?
O2B C8B C7B C6B 49.5(3) . . . . ?
O2B C8B C7B C14B -73.8(3) . . . . ?
O2B C8B C9B C10B -176.9(2) . . . . ?
O1A C14A C13A C12A -172.68(19) . . . . ?
O1B C14B C13B C12B -166.8(2) . . . . ?
C1A C6A C7A C8A -109.4(2) . . . . ?
C1A C6A C7A C11A 136.5(2) . . . . ?
C1A C6A C7A C14A 14.6(3) . . . . ?
C1A C6A C5A C4A -1.2(3) . . . . ?
C6A C1A C2A C3A -1.3(3) . . . . ?
C6A C7A C14A O1A -73.0(3) . . . . ?
C6A C7A C14A C13A 159.82(19) . . . . ?
C6A C7A C14A O1D 42.8(13) . . . . ?
C6A C5A C4A C3A -0.1(3) . . . . ?
C10A C11A C7A C6A 106.1(2) . . . . ?
C10A C11A C7A C8A -11.0(2) . . . . ?
C10A C11A C7A C14A -126.08(19) . . . . ?
C10A C11A C12A C13A 93.3(2) . . . . ?
C8A C7A C14A O1A 49.9(3) . . . . ?
C8A C7A C14A C13A -77.3(2) . . . . ?
C8A C7A C14A O1D 165.7(12) . . . . ?
C8B C7B C14B O1B 33.0(3) . . . . ?
C8B C7B C14B C13B -90.4(2) . . . . ?
C8B C7B C14B O1C 130.4(7) . . . . ?
C11A C10A C9A C8A -2.6(3) . . . . ?
C11A C7A C14A O1A 159.72(19) . . . . ?
C11A C7A C14A C13A 32.5(2) . . . . ?
C11A C7A C14A O1D -84.5(12) . . . . ?
C11A C12A C13A C14A 40.3(2) . . . . ?
C11B C10B C9B C8B -0.8(3) . . . . ?
C11B C7B C14B O1B 142.8(2) . . . . ?
C11B C7B C14B C13B 19.4(2) . . . . ?
C11B C7B C14B O1C -119.8(7) . . . . ?
C11B C12B C13B C14B 43.0(3) . . . . ?
C6B C7B C14B O1B -90.6(3) . . . . ?
C6B C7B C14B C13B 146.0(2) . . . . ?
C6B C7B C14B O1C 6.9(7) . . . . ?
C6B C1B C2B C3B -1.0(4) . . . . ?
C7A C6A C5A C4A -179.5(2) . . . . ?
C7A C8A C9A C10A -5.1(3) . . . . ?
C7A C11A C12A C13A -19.9(2) . . . . ?
C7A C14A C13A C12A -45.4(2) . . . . ?
C9A C10A C11A C7A 9.0(2) . . . . ?
C9A C10A C11A C12A -105.0(2) . . . . ?
C9A C8A C7A C6A -111.8(2) . . . . ?
C9A C8A C7A C11A 10.1(2) . . . . ?
C9A C8A C7A C14A 121.0(2) . . . . ?
C2A C1A C6A C7A -179.9(2) . . . . ?
C2A C1A C6A C5A 1.9(3) . . . . ?
C2A C3A C4A C5A 0.9(4) . . . . ?
C5A C6A C7A C8A 68.7(2) . . . . ?
C5A C6A C7A C11A -45.3(3) . . . . ?
C5A C6A C7A C14A -167.3(2) . . . . ?
C10B C11B C7B C8B 2.6(2) . . . . ?
C10B C11B C7B C6B 125.3(2) . . . . ?
C10B C11B C7B C14B -112.64(19) . . . . ?
C10B C11B C12B C13B 83.5(2) . . . . ?
C3B C4B C5B C6B -1.1(4) . . . . ?
C4B C3B C2B C1B -0.3(4) . . . . ?
C4A C3A C2A C1A -0.2(3) . . . . ?
C7B C8B C9B C10B 2.6(3) . . . . ?
C7B C11B C10B C9B -1.3(3) . . . . ?
C7B C11B C10B C15B 178.8(2) . . . . ?
C7B C11B C12B C13B -30.7(3) . . . . ?
C7B C6B C1B C2B 178.1(2) . . . . ?
C7B C6B C5B C4B -177.2(2) . . . . ?
C7B C14B C13B C12B -38.9(3) . . . . ?
C1B C6B C7B C8B 128.0(2) . . . . ?
C1B C6B C7B C11B 9.5(3) . . . . ?
C1B C6B C7B C14B -108.8(2) . . . . ?
C1B C6B C5B C4B -0.1(4) . . . . ?
C5B C6B C7B C8B -55.1(3) . . . . ?
C5B C6B C7B C11B -173.6(2) . . . . ?
C5B C6B C7B C14B 68.1(3) . . . . ?
C5B C6B C1B C2B 1.2(3) . . . . ?
C12B C11B C10B C9B -116.7(2) . . . . ?
C12B C11B C10B C15B 63.3(3) . . . . ?
C12B C11B C7B C8B 122.05(19) . . . . ?
C12B C11B C7B C6B -115.2(2) . . . . ?
C12B C11B C7B C14B 6.8(2) . . . . ?
C9B C8B C7B C11B -3.1(2) . . . . ?
C9B C8B C7B C6B -130.0(2) . . . . ?
C9B C8B C7B C14B 106.7(2) . . . . ?
C12A C11A C7A C6A -135.51(19) . . . . ?
C12A C11A C7A C8A 107.41(19) . . . . ?
C12A C11A C7A C14A -7.7(2) . . . . ?
C2B C3B C4B C5B 1.3(4) . . . . ?
C15A C10A C11A C7A -173.0(2) . . . . ?
C15A C10A C11A C12A 73.1(3) . . . . ?
C15A C10A C9A C8A 179.5(2) . . . . ?
C15B C10B C9B C8B 179.2(2) . . . . ?
O1C C14B C13B C12B 94.6(8) . . . . ?
O1D C14A C13A C12A 89.7(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-25
_olex2_date_sample_submission    2016-05-23
_olex2_submission_original_sample_id ca220516_1_1
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylene chloride'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_ca131218_1_1
_database_code_depnum_ccdc_archive 'CCDC 1913669'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Zurich
Switzerland
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-07-22 downloaded from the CCDC.
;
_audit_creation_date             2018-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 O2'
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H18O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.76169(11)
_cell_length_b                   6.20905(4)
_cell_length_c                   14.27446(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.4272(6)
_cell_angle_gamma                90
_cell_volume                     1302.475(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22908
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.2610
_cell_measurement_theta_min      6.0090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -9 0.0685
-2 0 9 0.0704
5 -2 6 0.1179
1 4 0 0.1072
-9 1 -2 0.1233
-9 -1 -2 0.1153
-2 -4 0 0.1096
-9 -1 2 0.1164
-10 0 1 0.1101
2 4 -4 0.1159
9 1 -2 0.1081
-1 -4 4 0.1138
-9 0 3 0.1115
-9 2 0 0.1214
0 -3 6 0.1043
-6 -1 8 0.1092
-1 -2 8 0.0954
8 0 -6 0.0938
-2 -1 9 0.0827
1 -1 9 0.0874
-2 2 8 0.0858
3 0 9 0.0793
1 -2 -8 0.0924
3 2 8 0.1020
6 0 6 0.0955
-2 -3 -4 0.1046
-1 4 3 0.1064
7 2 5 0.1165
6 3 1 0.1257
-6 -3 -1 0.1227
9 0 1 0.0939
8 2 0 0.1188
0 -4 2 0.1083
2 2 -8 0.0928
4 -1 -9 0.0828
-3 -4 -3 0.1063

_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.139
loop_
_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
2.0000 -0.0000 -9.0000 0.0796 0.9731 0.0589
-2.0000 0.0000 9.0000 -0.0796 -0.9731 -0.0589
5.0000 -2.0000 6.0000 -0.1114 -0.5144 -0.8557
1.0000 4.0000 -0.0000 0.8910 -0.0875 0.4409
-9.0000 1.0000 -2.0000 -0.3089 0.0660 0.9688
-9.0000 -1.0000 -2.0000 -0.7260 0.1164 0.7048
-2.0000 -4.0000 0.0000 -0.9477 0.0743 -0.3537
-9.0000 -1.0000 2.0000 -0.7111 -0.3044 0.6011
-10.0000 0.0000 1.0000 -0.5629 -0.2376 0.8462
2.0000 4.0000 -4.0000 0.9327 0.3464 0.4574
9.0000 1.0000 -2.0000 0.7111 0.3044 -0.6011
-1.0000 -4.0000 4.0000 -0.8761 -0.3332 -0.5446
-9.0000 0.0000 3.0000 -0.4987 -0.4347 0.7072
-9.0000 2.0000 0.0000 -0.0928 -0.1696 1.0490
-0.0000 -3.0000 6.0000 -0.6033 -0.5555 -0.5516
-6.0000 -1.0000 8.0000 -0.5186 -0.8957 0.1839
-1.0000 -2.0000 8.0000 -0.4439 -0.8043 -0.3842
8.0000 -0.0000 -6.0000 0.4308 0.7370 -0.5422
-2.0000 -1.0000 9.0000 -0.2882 -0.9479 -0.1909
1.0000 -1.0000 9.0000 -0.1182 -0.9081 -0.4526
-2.0000 2.0000 8.0000 0.3338 -0.9183 0.2311
3.0000 0.0000 9.0000 0.2037 -0.9069 -0.4950
1.0000 -2.0000 -8.0000 -0.3905 0.9050 -0.1439
3.0000 2.0000 8.0000 0.6171 -0.8521 -0.2050
6.0000 0.0000 6.0000 0.3624 -0.5516 -0.6788
-2.0000 -3.0000 -4.0000 -0.7541 0.4698 -0.1179
-1.0000 4.0000 3.0000 0.7889 -0.4296 0.5375
7.0000 2.0000 5.0000 0.8325 -0.4836 -0.4761
6.0000 3.0000 1.0000 0.9695 -0.1013 -0.1531
-6.0000 -3.0000 -1.0000 -0.9695 0.1013 0.1531
9.0000 -0.0000 1.0000 0.5137 0.0140 -0.8109
8.0000 2.0000 -0.0000 0.8705 0.0556 -0.4337
-0.0000 -4.0000 2.0000 -0.8269 -0.1096 -0.5799
2.0000 2.0000 -8.0000 0.5006 0.8175 0.2970
4.0000 -1.0000 -9.0000 -0.0156 1.0248 -0.2475
-3.0000 -4.0000 -3.0000 -1.0156 0.3766 -0.1887

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.490
_diffrn_reflns_theta_min         3.110
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 125.00   0.50    0.10    --   58.00  80.00 -85.35  184
  2  ω     38.00 128.00   0.50    0.10    --   62.00  78.00 -36.58  180
  3  ω     53.00 142.00   0.50    0.10    --   74.00  70.00-101.30  178
  4  ω     86.00 177.00   0.50    0.10    --  110.00  77.00 -90.00  182
  5  ω     86.00 177.00   0.50    0.10    --  110.00  77.00-180.00  182
  6  ω     86.00 177.00   0.50    0.10    --  110.00  77.00 -60.00  182
  7  ω     86.00 177.00   0.50    0.10    --  110.00  77.00  90.00  182
  8  ω     94.00 178.00   0.50    0.10    --  110.00  57.00  60.00  168
  9  ω     86.00 177.00   0.50    0.10    --  110.00  77.00 120.00  182
 10  ω     86.00 177.00   0.50    0.10    --  110.00  77.00  30.00  182
 11  ω     94.00 178.00   0.50    0.10    --  110.00  57.00   0.00  168
 12  ω     98.00 178.00   0.50    0.10    --  110.00  38.00 -90.00  160
 13  ω     94.00 178.00   0.50    0.10    --  110.00  57.00-150.00  168
 14  ω     86.00 177.00   0.50    0.10    --  110.00  77.00 -30.00  182
 15  ω     94.00 178.00   0.50    0.10    --  110.00  57.00-180.00  168
 16  ω     86.00 177.00   0.50    0.10    --  110.00  77.00   0.00  182
 17  ω     59.00 120.00   0.50    0.10    --   49.37 178.00 -30.00  122
 18  ω     98.00 124.00   0.50    0.10    --  110.00  38.00   0.00   52
 19  ω    101.00 137.00   0.50    0.10    --  110.00  38.00 120.00   72
 20  ω    115.00 141.00   0.50    0.10    --  110.00  38.00-180.00   52
 21  ω    100.00 127.00   0.50    0.10    --  110.00  38.00  60.00   54
 22  ω     98.00 178.00   0.50    0.10    --  110.00  38.00 150.00  160
 23  ω     86.00 177.00   0.50    0.10    --  110.00  77.00  60.00  182
 24  ω     94.00 178.00   0.50    0.10    --  110.00  57.00 150.00  168
 25  ω     86.00 177.00   0.50    0.10    --  110.00  77.00-150.00  182
 26  ω     86.00 177.00   0.50    0.10    --  110.00  77.00-120.00  182
 27  ω     26.00 116.00   0.50    0.10    --   49.37  77.00 -90.00  180
 28  ω     26.00 116.00   0.50    0.10    --   49.37  77.00-180.00  180
 29  ω     37.00 125.00   0.50    0.10    --   49.37  38.00  30.00  176
 30  ω     26.00 116.00   0.50    0.10    --   49.37  77.00   0.00  180
 31  ω    -63.00  26.00   0.50    0.10    --  -49.37  38.00   0.00  178
 32  ω    -94.00  -3.00   0.50    0.10    --  -70.00  77.00 150.00  182
 33  ω     38.00  84.00   0.50    0.10    --  110.00 -57.00 150.00   92
 34  ω     38.00  84.00   0.50    0.10    --  110.00 -57.00 -90.00   92
 35  ω     38.00  84.00   0.50    0.10    --  110.00 -57.00-120.00   92
 36  ω   -125.00 -36.00   0.50    0.10    --  -49.37 -38.00 -90.00  178
 37  ω   -128.00 -38.00   0.50    0.10    --  -62.00 -78.00-148.48  180
 38  ω   -129.00 -41.00   0.50    0.10    --  -62.00 -71.00  72.40  176
 39  ω   -136.00 -45.00   0.50    0.10    --  -70.00 -79.00 -59.20  182
 40  ω   -138.00 -50.00   0.50    0.10    --  -70.00 -68.00  88.57  176
 41  ω   -136.00 -46.00   0.50    0.10    --  -70.00 -78.00  46.96  180
 42  ω   -137.00 -46.00   0.50    0.10    --  -70.00 -77.00 -74.85  182
 43  ω   -136.00 -47.00   0.50    0.10    --  -70.00 -74.00 173.85  178
 44  ω   -137.00 -46.00   0.50    0.10    --  -70.00 -77.00  60.00  182
 45  ω   -137.00 -46.00   0.50    0.10    --  -70.00 -77.00-120.00  182
 46  ω   -139.00 -51.00   0.50    0.10    --  -70.00 -65.00 106.15  176
 47  ω   -137.00 -48.00   0.50    0.10    --  -70.00 -73.00   2.43  178
 48  ω   -137.00 -48.00   0.50    0.10    --  -70.00 -72.00 151.19  178
 49  ω   -137.00 -46.00   0.50    0.10    --  -70.00 -77.00 150.00  182
 50  ω   -140.00 -82.00   0.50    0.10    --  -70.00 -99.00-180.00  116
 51  ω   -124.00 -36.00   0.50    0.10    --  -49.37 -45.00-147.88  176
 52  ω   -121.00 -34.00   0.50    0.10    --  -49.37 -57.00 -30.00  174
 53  ω   -121.00 -34.00   0.50    0.10    --  -49.37 -57.00-180.00  174
 54  ω   -116.00 -26.00   0.50    0.10    --  -49.37 -77.00  60.00  180
 55  ω   -121.00 -34.00   0.50    0.10    --  -49.37 -57.00 120.00  174
 56  ω   -123.00 -26.00   0.50    0.10    --  -49.37  -6.00-111.12  194
 57  ω   -116.00 -26.00   0.50    0.10    --  -49.37 -77.00-150.00  180
 58  ω     39.00 122.00   0.50    0.10    --  110.00-125.00 150.00  166
 59  ω     40.00 110.00   0.50    0.10    --  110.00 -99.00   0.00  140
 60  ω     40.00 110.00   0.50    0.10    --  110.00 -99.00  60.00  140
 61  ω     40.00 110.00   0.50    0.10    --  110.00 -99.00-180.00  140
 62  ω     40.00 110.00   0.50    0.10    --  110.00 -99.00 -90.00  140
 63  ω     40.00 110.00   0.50    0.10    --  110.00 -99.00 120.00  140
 64  ω     52.00 105.00   0.50    0.10    --  110.00 -99.00  30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0566631000
_diffrn_orient_matrix_UB_12      0.2085928000
_diffrn_orient_matrix_UB_13      0.0037435000
_diffrn_orient_matrix_UB_21      0.0132439000
_diffrn_orient_matrix_UB_22      -0.0251975000
_diffrn_orient_matrix_UB_23      -0.1051764000
_diffrn_orient_matrix_UB_31      -0.0872148000
_diffrn_orient_matrix_UB_32      0.1320219000
_diffrn_orient_matrix_UB_33      -0.0259257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2768
_reflns_number_total             2793
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1225 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.074
_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)+(0.0415P)²+0.4195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          
'Disorder of the proton involved in hydrogen OH..O hydrogen bonding.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H9 of C9, H11 of C11, H12 of C12, H14 of C14, H15 of C15,
   H8 of C8, H6 of C6, H7 of C7
 At 1.5 times of:
  All C(H,H,H) groups, H2B of C16, All O(H) groups
2. Restrained distances
 O2-H2A = O2-H2B
 0.93 with sigma of 0.02
 O2-H2A \\sim O2-H2B
 with sigma of 0.02
3. Others
 Fixed Sof: H2A(0.5) H2B(0.5)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C13(H13A,H13B), C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
4.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35269(9) 0.87492(19) 0.87688(9) 0.0346(3) Uani 1 1 d . . . . .
O2 O 0.41738(8) 0.3083(2) 0.94402(9) 0.0389(3) Uani 1 1 d D . . . .
H2A H 0.465(3) 0.313(9) 0.992(3) 0.058 Uiso 0.5 1 d D . P A 1
C1 C 0.31332(11) 0.7028(3) 0.86469(10) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.34821(10) 0.5185(2) 0.80741(11) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.20524(10) 0.4401(3) 0.86879(10) 0.0241(3) Uani 1 1 d . . . . .
C4 C 0.21788(10) 0.3332(3) 0.70175(12) 0.0266(3) Uani 1 1 d . . . . .
C5 C 0.38723(11) 0.5895(3) 0.71663(11) 0.0265(3) Uani 1 1 d . . . . .
H5A H 0.418263 0.730379 0.725524 0.032 Uiso 1 1 calc R . . . .
H5B H 0.338261 0.602310 0.664536 0.032 Uiso 1 1 calc R . . . .
C6 C 0.23030(11) 0.6341(3) 0.90304(11) 0.0264(3) Uani 1 1 d . . . . .
H6 H 0.198506 0.714859 0.946023 0.032 Uiso 1 1 calc R . . . .
C7 C 0.16188(11) 0.4979(3) 0.66347(12) 0.0297(4) Uani 1 1 d . . . . .
H7 H 0.155948 0.626523 0.698384 0.036 Uiso 1 1 calc R . . . .
C8 C 0.26832(10) 0.3547(3) 0.79903(11) 0.0242(3) Uani 1 1 d . . . . .
H8 H 0.291699 0.210045 0.820526 0.029 Uiso 1 1 calc R . . . .
C9 C 0.43493(11) 0.4234(3) 0.86219(12) 0.0288(4) Uani 1 1 d . . . . .
H9 H 0.476298 0.546047 0.882023 0.035 Uiso 1 1 calc R . . . .
C10 C 0.12391(11) 0.3128(4) 0.88903(13) 0.0354(4) Uani 1 1 d . . . . .
H10A H 0.091760 0.387950 0.936381 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.143204 0.170437 0.912908 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.083223 0.296250 0.831139 0.053 Uiso 1 1 calc GR . . . .
C11 C 0.11458(12) 0.4769(4) 0.57507(13) 0.0390(5) Uani 1 1 d . . . . .
H11 H 0.076554 0.590542 0.550062 0.047 Uiso 1 1 calc R . . . .
C12 C 0.22620(13) 0.1476(3) 0.64825(16) 0.0394(5) Uani 1 1 d . . . . .
H12 H 0.264485 0.033793 0.672589 0.047 Uiso 1 1 calc R . . . .
C13 C 0.47979(12) 0.2930(3) 0.78849(14) 0.0373(4) Uani 1 1 d . . . . .
H13A H 0.455812 0.144042 0.784993 0.045 Uiso 1 1 calc R . . . .
H13B H 0.546577 0.287480 0.803818 0.045 Uiso 1 1 calc R . . . .
C14 C 0.12287(13) 0.2899(4) 0.52327(14) 0.0475(6) Uani 1 1 d . . . . .
H14 H 0.089981 0.274215 0.463169 0.057 Uiso 1 1 calc R . . . .
C15 C 0.17900(16) 0.1274(4) 0.55952(17) 0.0510(6) Uani 1 1 d . . . . .
H15 H 0.185630 0.000314 0.523732 0.061 Uiso 1 1 calc R . . . .
C16 C 0.45551(13) 0.4125(4) 0.69510(14) 0.0396(4) Uani 1 1 d . . . . .
H16A H 0.427701 0.312420 0.646587 0.047 Uiso 1 1 calc R . . . .
H16B H 0.510610 0.476889 0.672086 0.047 Uiso 1 1 calc R . . . .
H2B H 0.395(4) 0.171(5) 0.925(4) 0.059 Uiso 0.5 1 d D . P B 2


_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 1.221(2) . ?
O2 H2A 0.93(2) . ?
O2 C9 1.4141(19) . ?
O2 H2B 0.95(2) . ?
C1 C2 1.524(2) . ?
C1 C6 1.453(2) . ?
C2 C5 1.532(2) . ?
C2 C8 1.553(2) . ?
C2 C9 1.552(2) . ?
C3 C6 1.339(3) . ?
C3 C8 1.522(2) . ?
C3 C10 1.488(2) . ?
C4 C7 1.393(2) . ?
C4 C8 1.518(2) . ?
C4 C12 1.394(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C16 1.542(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C11 1.389(2) . ?
C8 H8 1.0000 . ?
C9 H9 1.0000 . ?
C9 C13 1.527(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C14 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C15 1.392(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C16 1.538(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.375(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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 O2 H2A 114(3) . . ?
C9 O2 H2B 108(4) . . ?
O1 C1 C2 123.59(15) . . ?
O1 C1 C6 127.61(16) . . ?
C6 C1 C2 108.76(14) . . ?
C1 C2 C5 114.25(13) . . ?
C1 C2 C8 103.90(13) . . ?
C1 C2 C9 108.65(13) . . ?
C5 C2 C8 117.82(13) . . ?
C5 C2 C9 100.22(12) . . ?
C9 C2 C8 111.96(13) . . ?
C6 C3 C8 112.80(14) . . ?
C6 C3 C10 127.37(16) . . ?
C10 C3 C8 119.79(16) . . ?
C7 C4 C8 121.04(14) . . ?
C7 C4 C12 118.12(16) . . ?
C12 C4 C8 120.84(16) . . ?
C2 C5 H5A 110.6 . . ?
C2 C5 H5B 110.6 . . ?
C2 C5 C16 105.58(13) . . ?
H5A C5 H5B 108.8 . . ?
C16 C5 H5A 110.6 . . ?
C16 C5 H5B 110.6 . . ?
C1 C6 H6 125.1 . . ?
C3 C6 C1 109.89(15) . . ?
C3 C6 H6 125.1 . . ?
C4 C7 H7 119.5 . . ?
C11 C7 C4 121.07(17) . . ?
C11 C7 H7 119.5 . . ?
C2 C8 H8 109.1 . . ?
C3 C8 C2 103.22(13) . . ?
C3 C8 H8 109.1 . . ?
C4 C8 C2 115.55(13) . . ?
C4 C8 C3 110.59(12) . . ?
C4 C8 H8 109.1 . . ?
O2 C9 C2 113.68(12) . . ?
O2 C9 H9 107.8 . . ?
O2 C9 C13 115.23(15) . . ?
C2 C9 H9 107.8 . . ?
C13 C9 C2 104.20(14) . . ?
C13 C9 H9 107.8 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11 120.0 . . ?
C14 C11 C7 120.0(2) . . ?
C14 C11 H11 120.0 . . ?
C4 C12 H12 119.7 . . ?
C15 C12 C4 120.7(2) . . ?
C15 C12 H12 119.7 . . ?
C9 C13 H13A 110.7 . . ?
C9 C13 H13B 110.7 . . ?
C9 C13 C16 105.11(14) . . ?
H13A C13 H13B 108.8 . . ?
C16 C13 H13A 110.7 . . ?
C16 C13 H13B 110.7 . . ?
C11 C14 H14 120.2 . . ?
C15 C14 C11 119.58(18) . . ?
C15 C14 H14 120.2 . . ?
C12 C15 H15 119.7 . . ?
C14 C15 C12 120.53(18) . . ?
C14 C15 H15 119.7 . . ?
C5 C16 H16A 110.6 . . ?
C5 C16 H16B 110.6 . . ?
C13 C16 C5 105.91(14) . . ?
C13 C16 H16A 110.6 . . ?
C13 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?

_olex2_date_sample_submission    2018-12-13
_olex2_submission_original_sample_id ca131218_1_1
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.884
_exptl_crystal_recrystallization_method 
'vapour diffusion from hexanes into methylene chloride at 4 °C'
