# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2419977'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2025-01-27 deposited with the CCDC.	2025-03-21 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2019/2

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Lucia Trevisan'
_cambridge_user_crsid            lt459
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             LT-224
_cambridge_data_id               CH_B1_0050
#-------------------------------------------------------------------------------
# start Validation Reply Form
_vrf_THETM01_3                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was a very thin needle and diffraction was weak.
I/sigma(I) falls below 3.0 around 1.25 angstrom. The data are
integrated to 0.95 angstrom (where I/sigma(I) = 0.5). The full intensity
statistics are included in _reflns_special_details.
;
_vrf_RINTA01_3                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: This follows from the description of the weak data in response to
_vrf_THETM01.
;
_vrf_PLAT020_3                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.200 Report
RESPONSE: This follows from the description of the weak data in response to
_vrf_THETM01.
;
_vrf_PLAT026_3                   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        39% Check 
RESPONSE: This follows from the description of the weak data in response to
_vrf_THETM01.
;
_vrf_PLAT340_3                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01194 Ang.  
RESPONSE: This follows from the description of the weak data in response to
_vrf_THETM01.
;
# end Validation Reply Form
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 F O2'
_chemical_formula_sum            'C11 H15 F O2'
_chemical_formula_weight         198.23

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5600(11)
_cell_length_b                   14.795(3)
_cell_length_c                   17.736(3)
_cell_angle_alpha                100.253(6)
_cell_angle_beta                 98.746(6)
_cell_angle_gamma                100.247(6)
_cell_volume                     1636.6(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    1480
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      50.61

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.772
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5207
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15674
_diffrn_reflns_av_unetI/netI     0.1942
_diffrn_reflns_av_R_equivalents  0.1999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.578
_diffrn_reflns_theta_max         54.170
_diffrn_reflns_theta_full        54.170
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3889
_reflns_number_gt                1525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.

#===============================================================================
INTENSITY STATISTICS FOR DATASET # 1  CH_B1_0050_0m.hkl
#===============================================================================
 Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 3.82      59     65     90.8     3.77    190.51   16.76  0.0345  0.0492
 3.82 - 2.57     136    136    100.0     5.10     78.46   14.61  0.0449  0.0474
 2.57 - 2.05     200    200    100.0     5.32     48.22   14.34  0.0583  0.0539
 2.05 - 1.79     195    197     99.0     5.46     25.81   11.03  0.1049  0.0673
 1.79 - 1.62     193    197     98.0     5.00     20.15    8.81  0.1305  0.0836
 1.62 - 1.51     203    205     99.0     4.70     10.08    5.38  0.2413  0.1469
 1.51 - 1.43     184    187     98.4     4.68      6.29    3.73  0.3511  0.2138
 1.43 - 1.35     194    198     98.0     4.73      5.07    3.32  0.3842  0.2490
 1.35 - 1.29     203    204     99.5     4.51      6.79    3.25  0.3587  0.2365
 1.29 - 1.24     206    209     98.6     4.22      4.61    2.45  0.4926  0.3587
 1.24 - 1.20     180    186     96.8     3.93      6.33    2.73  0.4332  0.3129
 1.20 - 1.16     212    217     97.7     3.64      4.45    1.88  0.5172  0.4358
 1.16 - 1.13     163    164     99.4     3.70      5.26    2.16  0.4676  0.3678
 1.13 - 1.10     198    200     99.0     3.82      4.73    1.82  0.5643  0.4343
 1.10 - 1.07     220    222     99.1     3.66      4.36    1.20  0.7083  0.6135
 1.07 - 1.05     176    180     97.8     3.41      4.20    1.05  0.8362  0.6226
 1.05 - 1.02     266    269     98.9     3.45      3.33    0.92  0.8655  0.7799
 1.02 - 1.00     198    200     99.0     2.94      2.79    0.73  0.8493  0.8997
 1.00 - 0.98     205    208     98.6     2.60      1.75    0.59  0.8583  1.3497
 0.98 - 0.97     118    119     99.2     2.36      1.49    0.62  0.8960  1.2547
 0.97 - 0.95     180    220     81.8     1.71      2.31    0.53  0.9057  1.1433
#-------------------------------------------------------------------------------
 1.05 - 0.95     967   1016     95.2     2.67      2.47    0.70  0.8666  0.9916
  Inf - 0.95    3889   3983     97.6     3.94     14.13    4.12  0.1594  0.1567
#===============================================================================
;

_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
The H atoms of the OH groups are are placed in idealised positions (they are
not located). The intramolecular H-bonds are unambiguous because there are no
competing H-bond acceptors. The intermolecular H-bonds are ambiguous: the
cooperative chain could run in either direction along the a axis.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0973P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0077(9)
_refine_ls_number_reflns         3889
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2263
_refine_ls_R_factor_gt           0.0986
_refine_ls_wR_factor_ref         0.2314
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048

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 1.2767(7) 0.9965(3) 0.4138(2) 0.0925(15) Uani 1 1 d . . . . .
O1A O 0.6974(8) 0.7409(3) 0.5028(3) 0.0846(16) Uani 1 1 d . . . . .
H1A H 0.595396 0.719420 0.465267 0.127 Uiso 1 1 d R U . . .
O2A O 0.4795(7) 0.7177(4) 0.3513(3) 0.0858(17) Uani 1 1 d . . . . .
H2A H 0.556021 0.711003 0.316960 0.129 Uiso 1 1 d R U . . .
C1A C 0.8467(12) 0.8071(5) 0.4820(4) 0.069(2) Uani 1 1 d . . . . .
C2A C 0.7833(12) 0.8441(5) 0.4176(4) 0.069(2) Uani 1 1 d . . . . .
C3A C 0.9317(14) 0.9083(5) 0.3940(4) 0.075(2) Uani 1 1 d . . . . .
H3A H 0.894088 0.933236 0.349266 0.090 Uiso 1 1 calc R U . . .
C4A C 1.1298(13) 0.9337(5) 0.4365(5) 0.075(2) Uani 1 1 d . . . . .
C5A C 1.1906(12) 0.8995(5) 0.5011(5) 0.073(2) Uani 1 1 d . . . . .
H5A H 1.331895 0.919881 0.529000 0.088 Uiso 1 1 calc R U . . .
C6A C 1.0490(13) 0.8350(5) 0.5271(4) 0.066(2) Uani 1 1 d . . . . .
C7A C 1.1155(12) 0.7970(6) 0.5999(5) 0.075(2) Uani 1 1 d . . . . .
C8A C 1.3430(12) 0.8448(6) 0.6409(4) 0.096(3) Uani 1 1 d . . . . .
H8A H 1.352162 0.912420 0.658041 0.143 Uiso 1 1 calc R U . . .
H8B H 1.439044 0.834658 0.604436 0.143 Uiso 1 1 calc R U . . .
H8C H 1.382547 0.817936 0.686217 0.143 Uiso 1 1 calc R U . . .
C9A C 1.1030(13) 0.6908(6) 0.5785(4) 0.091(3) Uani 1 1 d . . . . .
H9A H 0.959040 0.658927 0.552207 0.137 Uiso 1 1 calc R U . . .
H9B H 1.140433 0.667550 0.626076 0.137 Uiso 1 1 calc R U . . .
H9C H 1.201425 0.677930 0.543572 0.137 Uiso 1 1 calc R U . . .
C10A C 0.9711(13) 0.8182(5) 0.6588(4) 0.092(3) Uani 1 1 d . . . . .
H10A H 0.825844 0.784617 0.636169 0.138 Uiso 1 1 calc R U . . .
H10B H 0.976198 0.885933 0.671093 0.138 Uiso 1 1 calc R U . . .
H10C H 1.019476 0.797567 0.706732 0.138 Uiso 1 1 calc R U . . .
C11A C 0.5573(12) 0.8192(5) 0.3767(4) 0.082(2) Uani 1 1 d . . . . .
H11A H 0.469571 0.845158 0.412261 0.098 Uiso 1 1 calc R U . . .
H11B H 0.543170 0.848520 0.330613 0.098 Uiso 1 1 calc R U . . .
F1B F -0.1091(7) 0.5797(3) 0.0313(2) 0.0978(15) Uani 1 1 d . . . . .
O1B O 0.6097(8) 0.8344(3) 0.1827(2) 0.0864(17) Uani 1 1 d . . . . .
H1B H 0.695895 0.807256 0.205023 0.130 Uiso 1 1 d R U . . .
O2B O 0.7237(7) 0.6965(3) 0.2435(3) 0.0805(16) Uani 1 1 d . . . . .
H2B H 0.846367 0.686625 0.252587 0.121 Uiso 1 1 d R U . . .
C1B C 0.4268(12) 0.7690(6) 0.1458(4) 0.070(2) Uani 1 1 d . . . . .
C2B C 0.4190(12) 0.6731(6) 0.1408(4) 0.067(2) Uani 1 1 d . . . . .
C3B C 0.2329(13) 0.6091(5) 0.1020(4) 0.072(2) Uani 1 1 d . . . . .
H3B H 0.222537 0.543421 0.097779 0.086 Uiso 1 1 calc R U . . .
C4B C 0.0697(13) 0.6423(7) 0.0710(4) 0.078(3) Uani 1 1 d . . . . .
C5B C 0.0740(12) 0.7359(6) 0.0752(4) 0.076(2) Uani 1 1 d . . . . .
H5B H -0.045816 0.755197 0.051204 0.091 Uiso 1 1 calc R U . . .
C6B C 0.2528(13) 0.8029(6) 0.1145(4) 0.070(2) Uani 1 1 d . . . . .
C7B C 0.2564(13) 0.9087(6) 0.1233(4) 0.082(2) Uani 1 1 d . . . . .
C8B C 0.0487(14) 0.9255(5) 0.0813(4) 0.105(3) Uani 1 1 d . . . . .
H8D H 0.025429 0.896163 0.025739 0.157 Uiso 1 1 calc R U . . .
H8E H 0.056120 0.993197 0.087128 0.157 Uiso 1 1 calc R U . . .
H8F H -0.068114 0.897860 0.104098 0.157 Uiso 1 1 calc R U . . .
C9B C 0.2827(13) 0.9554(5) 0.2106(4) 0.102(3) Uani 1 1 d . . . . .
H9D H 0.162849 0.927053 0.231578 0.154 Uiso 1 1 calc R U . . .
H9E H 0.287935 1.022905 0.215747 0.154 Uiso 1 1 calc R U . . .
H9F H 0.413878 0.945868 0.239603 0.154 Uiso 1 1 calc R U . . .
C10B C 0.4344(14) 0.9587(6) 0.0889(5) 0.105(3) Uani 1 1 d . . . . .
H10D H 0.430697 0.923669 0.036188 0.158 Uiso 1 1 calc R U . . .
H10E H 0.570636 0.961806 0.121967 0.158 Uiso 1 1 calc R U . . .
H10F H 0.415629 1.022456 0.086716 0.158 Uiso 1 1 calc R U . . .
C11B C 0.6104(13) 0.6378(5) 0.1697(4) 0.091(3) Uani 1 1 d . . . . .
H11C H 0.567146 0.572497 0.176229 0.109 Uiso 1 1 calc R U . . .
H11D H 0.704033 0.637652 0.130917 0.109 Uiso 1 1 calc R U . . .
F1C F 0.3382(9) 0.4306(3) 0.3854(3) 0.1172(17) Uani 1 1 d . . . . .
O1C O 0.9404(8) 0.4567(3) 0.2043(3) 0.0883(17) Uani 1 1 d . . . . .
H1C H 1.014825 0.511347 0.214762 0.132 Uiso 1 1 d R U . . .
O2C O 1.0725(7) 0.6350(3) 0.2912(3) 0.0874(17) Uani 1 1 d . . . . .
H2C H 1.178410 0.678877 0.309419 0.131 Uiso 1 1 d R U . . .
C1C C 0.7888(13) 0.4521(5) 0.2504(5) 0.069(2) Uani 1 1 d . . . . .
C2C C 0.8215(14) 0.5136(5) 0.3216(5) 0.074(2) Uani 1 1 d . . . . .
C3C C 0.6699(16) 0.5078(6) 0.3672(5) 0.082(2) Uani 1 1 d . . . . .
H3C H 0.688443 0.550351 0.415892 0.098 Uiso 1 1 calc R U . . .
C4C C 0.4876(15) 0.4374(6) 0.3396(6) 0.081(2) Uani 1 1 d . . . . .
C5C C 0.4540(14) 0.3774(6) 0.2691(6) 0.087(3) Uani 1 1 d . . . . .
H5C H 0.325186 0.332145 0.252131 0.104 Uiso 1 1 calc R U . . .
C6C C 0.6029(14) 0.3806(5) 0.2214(5) 0.074(2) Uani 1 1 d . . . . .
C7C C 0.5648(13) 0.3123(6) 0.1419(4) 0.079(2) Uani 1 1 d . . . . .
C8C C 0.3523(12) 0.2410(5) 0.1246(4) 0.103(3) Uani 1 1 d . . . . .
H8G H 0.236281 0.274551 0.122121 0.155 Uiso 1 1 calc R U . . .
H8H H 0.347093 0.205355 0.166085 0.155 Uiso 1 1 calc R U . . .
H8I H 0.338689 0.197689 0.074470 0.155 Uiso 1 1 calc R U . . .
C9C C 0.5602(14) 0.3680(6) 0.0763(4) 0.106(3) Uani 1 1 d . . . . .
H9G H 0.442845 0.400787 0.076212 0.158 Uiso 1 1 calc R U . . .
H9H H 0.541543 0.324702 0.025863 0.158 Uiso 1 1 calc R U . . .
H9J H 0.693419 0.414061 0.085022 0.158 Uiso 1 1 calc R U . . .
C10C C 0.7403(13) 0.2549(6) 0.1393(4) 0.101(3) Uani 1 1 d . . . . .
H10G H 0.878233 0.297925 0.149652 0.151 Uiso 1 1 calc R U . . .
H10H H 0.717755 0.213916 0.087537 0.151 Uiso 1 1 calc R U . . .
H10I H 0.735911 0.216557 0.178945 0.151 Uiso 1 1 calc R U . . .
C11C C 1.0234(12) 0.5851(5) 0.3519(4) 0.087(3) Uani 1 1 d . . . . .
H11E H 1.008901 0.629995 0.398277 0.104 Uiso 1 1 calc R U . . .
H11F H 1.139232 0.553529 0.367541 0.104 Uiso 1 1 calc R U . . .


_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 C4A 1.373(8) . ?
O1A C1A 1.397(8) . ?
O1A H1A 0.8399 . ?
O2A C11A 1.462(7) . ?
O2A H2A 0.8501 . ?
C1A C6A 1.391(9) . ?
C1A C2A 1.392(9) . ?
C2A C3A 1.400(9) . ?
C2A C11A 1.498(9) . ?
C3A C4A 1.352(9) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.368(9) . ?
C5A C6A 1.399(9) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.531(9) . ?
C7A C9A 1.534(10) . ?
C7A C8A 1.539(9) . ?
C7A C10A 1.543(10) . ?
C8A H8A 0.9800 . ?
C8A H8B 0.9800 . ?
C8A H8C 0.9800 . ?
C9A H9A 0.9800 . ?
C9A H9B 0.9800 . ?
C9A H9C 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
F1B C4B 1.364(8) . ?
O1B C1B 1.389(7) . ?
O1B H1B 0.8400 . ?
O2B C11B 1.445(7) . ?
O2B H2B 0.8400 . ?
C1B C2B 1.397(9) . ?
C1B C6B 1.404(9) . ?
C2B C3B 1.401(9) . ?
C2B C11B 1.498(9) . ?
C3B C4B 1.340(10) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.367(9) . ?
C5B C6B 1.391(9) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.542(10) . ?
C7B C10B 1.533(10) . ?
C7B C8B 1.533(10) . ?
C7B C9B 1.549(9) . ?
C8B H8D 0.9800 . ?
C8B H8E 0.9800 . ?
C8B H8F 0.9800 . ?
C9B H9D 0.9800 . ?
C9B H9E 0.9800 . ?
C9B H9F 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
F1C C4C 1.366(9) . ?
O1C C1C 1.381(9) . ?
O1C H1C 0.8400 . ?
O2C C11C 1.452(8) . ?
O2C H2C 0.8400 . ?
C1C C2C 1.381(9) . ?
C1C C6C 1.424(9) . ?
C2C C3C 1.374(10) . ?
C2C C11C 1.499(9) . ?
C3C C4C 1.397(10) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.361(10) . ?
C5C C6C 1.386(10) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.538(10) . ?
C7C C9C 1.541(9) . ?
C7C C8C 1.544(9) . ?
C7C C10C 1.549(10) . ?
C8C H8G 0.9800 . ?
C8C H8H 0.9800 . ?
C8C H8I 0.9800 . ?
C9C H9G 0.9800 . ?
C9C H9H 0.9800 . ?
C9C H9J 0.9800 . ?
C10C H10G 0.9800 . ?
C10C H10H 0.9800 . ?
C10C H10I 0.9800 . ?
C11C H11E 0.9900 . ?
C11C H11F 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
C1A O1A H1A 109.5 . . ?
C11A O2A H2A 95.0 . . ?
C6A C1A C2A 122.9(8) . . ?
C6A C1A O1A 119.2(7) . . ?
C2A C1A O1A 117.9(7) . . ?
C1A C2A C3A 119.0(7) . . ?
C1A C2A C11A 120.4(8) . . ?
C3A C2A C11A 120.5(8) . . ?
C4A C3A C2A 118.2(7) . . ?
C4A C3A H3A 120.9 . . ?
C2A C3A H3A 120.9 . . ?
C3A C4A C5A 122.8(8) . . ?
C3A C4A F1A 118.7(8) . . ?
C5A C4A F1A 118.5(7) . . ?
C4A C5A C6A 121.4(7) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
C1A C6A C5A 115.6(7) . . ?
C1A C6A C7A 122.7(7) . . ?
C5A C6A C7A 121.6(7) . . ?
C6A C7A C9A 110.8(6) . . ?
C6A C7A C8A 111.3(6) . . ?
C9A C7A C8A 108.2(7) . . ?
C6A C7A C10A 109.6(7) . . ?
C9A C7A C10A 109.7(6) . . ?
C8A C7A C10A 107.2(6) . . ?
C7A C8A H8A 109.5 . . ?
C7A C8A H8B 109.5 . . ?
H8A C8A H8B 109.5 . . ?
C7A C8A H8C 109.5 . . ?
H8A C8A H8C 109.5 . . ?
H8B C8A H8C 109.5 . . ?
C7A C9A H9A 109.5 . . ?
C7A C9A H9B 109.5 . . ?
H9A C9A H9B 109.5 . . ?
C7A C9A H9C 109.5 . . ?
H9A C9A H9C 109.5 . . ?
H9B C9A H9C 109.5 . . ?
C7A C10A H10A 109.5 . . ?
C7A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C7A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
O2A C11A C2A 112.1(6) . . ?
O2A C11A H11A 109.2 . . ?
C2A C11A H11A 109.2 . . ?
O2A C11A H11B 109.2 . . ?
C2A C11A H11B 109.2 . . ?
H11A C11A H11B 107.9 . . ?
C1B O1B H1B 109.4 . . ?
C11B O2B H2B 109.6 . . ?
O1B C1B C2B 120.3(8) . . ?
O1B C1B C6B 117.7(8) . . ?
C2B C1B C6B 122.0(7) . . ?
C1B C2B C3B 118.7(8) . . ?
C1B C2B C11B 121.2(7) . . ?
C3B C2B C11B 119.9(8) . . ?
C4B C3B C2B 118.6(7) . . ?
C4B C3B H3B 120.7 . . ?
C2B C3B H3B 120.7 . . ?
C3B C4B F1B 118.5(8) . . ?
C3B C4B C5B 123.6(7) . . ?
F1B C4B C5B 117.9(8) . . ?
C4B C5B C6B 120.4(8) . . ?
C4B C5B H5B 119.8 . . ?
C6B C5B H5B 119.8 . . ?
C5B C6B C1B 116.6(7) . . ?
C5B C6B C7B 121.1(8) . . ?
C1B C6B C7B 122.3(7) . . ?
C10B C7B C8B 107.2(7) . . ?
C10B C7B C6B 112.0(7) . . ?
C8B C7B C6B 111.2(6) . . ?
C10B C7B C9B 109.3(7) . . ?
C8B C7B C9B 107.0(7) . . ?
C6B C7B C9B 110.0(6) . . ?
C7B C8B H8D 109.5 . . ?
C7B C8B H8E 109.5 . . ?
H8D C8B H8E 109.5 . . ?
C7B C8B H8F 109.5 . . ?
H8D C8B H8F 109.5 . . ?
H8E C8B H8F 109.5 . . ?
C7B C9B H9D 109.5 . . ?
C7B C9B H9E 109.5 . . ?
H9D C9B H9E 109.5 . . ?
C7B C9B H9F 109.5 . . ?
H9D C9B H9F 109.5 . . ?
H9E C9B H9F 109.5 . . ?
C7B C10B H10D 109.5 . . ?
C7B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C7B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
O2B C11B C2B 110.6(6) . . ?
O2B C11B H11C 109.5 . . ?
C2B C11B H11C 109.5 . . ?
O2B C11B H11D 109.5 . . ?
C2B C11B H11D 109.5 . . ?
H11C C11B H11D 108.1 . . ?
C1C O1C H1C 109.5 . . ?
C11C O2C H2C 109.6 . . ?
O1C C1C C2C 120.6(7) . . ?
O1C C1C C6C 116.7(8) . . ?
C2C C1C C6C 122.7(9) . . ?
C3C C2C C1C 120.0(8) . . ?
C3C C2C C11C 118.8(8) . . ?
C1C C2C C11C 121.2(9) . . ?
C2C C3C C4C 117.8(8) . . ?
C2C C3C H3C 121.1 . . ?
C4C C3C H3C 121.1 . . ?
C5C C4C F1C 119.7(9) . . ?
C5C C4C C3C 122.4(9) . . ?
F1C C4C C3C 117.9(9) . . ?
C4C C5C C6C 121.7(8) . . ?
C4C C5C H5C 119.2 . . ?
C6C C5C H5C 119.2 . . ?
C5C C6C C1C 115.4(8) . . ?
C5C C6C C7C 121.5(8) . . ?
C1C C6C C7C 123.0(9) . . ?
C6C C7C C9C 109.6(6) . . ?
C6C C7C C8C 112.8(7) . . ?
C9C C7C C8C 106.9(6) . . ?
C6C C7C C10C 110.4(6) . . ?
C9C C7C C10C 110.1(7) . . ?
C8C C7C C10C 107.0(7) . . ?
C7C C8C H8G 109.5 . . ?
C7C C8C H8H 109.5 . . ?
H8G C8C H8H 109.5 . . ?
C7C C8C H8I 109.5 . . ?
H8G C8C H8I 109.5 . . ?
H8H C8C H8I 109.5 . . ?
C7C C9C H9G 109.5 . . ?
C7C C9C H9H 109.5 . . ?
H9G C9C H9H 109.5 . . ?
C7C C9C H9J 109.5 . . ?
H9G C9C H9J 109.5 . . ?
H9H C9C H9J 109.5 . . ?
C7C C10C H10G 109.5 . . ?
C7C C10C H10H 109.5 . . ?
H10G C10C H10H 109.5 . . ?
C7C C10C H10I 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 109.5 . . ?
O2C C11C C2C 109.3(6) . . ?
O2C C11C H11E 109.8 . . ?
C2C C11C H11E 109.8 . . ?
O2C C11C H11F 109.8 . . ?
C2C C11C H11F 109.8 . . ?
H11E C11C H11F 108.3 . . ?

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
C6A C1A C2A C3A 3.7(11) . . . . ?
O1A C1A C2A C3A -177.9(7) . . . . ?
C6A C1A C2A C11A -173.3(7) . . . . ?
O1A C1A C2A C11A 5.2(10) . . . . ?
C1A C2A C3A C4A -1.9(11) . . . . ?
C11A C2A C3A C4A 175.0(7) . . . . ?
C2A C3A C4A C5A 0.0(12) . . . . ?
C2A C3A C4A F1A 179.9(6) . . . . ?
C3A C4A C5A C6A 0.2(12) . . . . ?
F1A C4A C5A C6A -179.6(7) . . . . ?
C2A C1A C6A C5A -3.3(11) . . . . ?
O1A C1A C6A C5A 178.2(6) . . . . ?
C2A C1A C6A C7A 177.5(7) . . . . ?
O1A C1A C6A C7A -0.9(11) . . . . ?
C4A C5A C6A C1A 1.4(11) . . . . ?
C4A C5A C6A C7A -179.4(7) . . . . ?
C1A C6A C7A C9A 63.3(10) . . . . ?
C5A C6A C7A C9A -115.8(8) . . . . ?
C1A C6A C7A C8A -176.3(7) . . . . ?
C5A C6A C7A C8A 4.6(10) . . . . ?
C1A C6A C7A C10A -58.0(9) . . . . ?
C5A C6A C7A C10A 122.9(7) . . . . ?
C1A C2A C11A O2A -55.4(9) . . . . ?
C3A C2A C11A O2A 127.7(7) . . . . ?
O1B C1B C2B C3B -179.0(6) . . . . ?
C6B C1B C2B C3B 1.2(11) . . . . ?
O1B C1B C2B C11B -4.4(11) . . . . ?
C6B C1B C2B C11B 175.9(7) . . . . ?
C1B C2B C3B C4B 0.2(11) . . . . ?
C11B C2B C3B C4B -174.5(7) . . . . ?
C2B C3B C4B F1B 178.1(6) . . . . ?
C2B C3B C4B C5B -0.2(12) . . . . ?
C3B C4B C5B C6B -1.2(12) . . . . ?
F1B C4B C5B C6B -179.6(7) . . . . ?
C4B C5B C6B C1B 2.5(11) . . . . ?
C4B C5B C6B C7B -176.9(7) . . . . ?
O1B C1B C6B C5B 177.7(6) . . . . ?
C2B C1B C6B C5B -2.5(11) . . . . ?
O1B C1B C6B C7B -2.9(11) . . . . ?
C2B C1B C6B C7B 176.9(7) . . . . ?
C5B C6B C7B C10B -122.4(8) . . . . ?
C1B C6B C7B C10B 58.2(9) . . . . ?
C5B C6B C7B C8B -2.5(10) . . . . ?
C1B C6B C7B C8B 178.1(7) . . . . ?
C5B C6B C7B C9B 115.9(8) . . . . ?
C1B C6B C7B C9B -63.5(10) . . . . ?
C1B C2B C11B O2B 42.3(10) . . . . ?
C3B C2B C11B O2B -143.1(6) . . . . ?
O1C C1C C2C C3C -179.5(7) . . . . ?
C6C C1C C2C C3C -0.9(11) . . . . ?
O1C C1C C2C C11C -1.5(11) . . . . ?
C6C C1C C2C C11C 177.2(7) . . . . ?
C1C C2C C3C C4C 1.3(11) . . . . ?
C11C C2C C3C C4C -176.7(7) . . . . ?
C2C C3C C4C C5C -2.1(12) . . . . ?
C2C C3C C4C F1C 179.0(7) . . . . ?
F1C C4C C5C C6C -178.8(7) . . . . ?
C3C C4C C5C C6C 2.3(12) . . . . ?
C4C C5C C6C C1C -1.6(11) . . . . ?
C4C C5C C6C C7C 179.7(7) . . . . ?
O1C C1C C6C C5C 179.6(7) . . . . ?
C2C C1C C6C C5C 0.9(11) . . . . ?
O1C C1C C6C C7C -1.6(10) . . . . ?
C2C C1C C6C C7C 179.6(7) . . . . ?
C5C C6C C7C C9C 117.1(8) . . . . ?
C1C C6C C7C C9C -61.6(10) . . . . ?
C5C C6C C7C C8C -1.9(10) . . . . ?
C1C C6C C7C C8C 179.4(7) . . . . ?
C5C C6C C7C C10C -121.6(8) . . . . ?
C1C C6C C7C C10C 59.8(10) . . . . ?
C3C C2C C11C O2C -132.9(7) . . . . ?
C1C C2C C11C O2C 49.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1A H1A O2A 0.84 2.04 2.776(6) 145.7 . yes
O2A H2A O2B 0.85 1.84 2.687(7) 179.4 . yes
O1B H1B O2B 0.84 1.91 2.638(6) 144.2 . yes
O2B H2B O2C 0.84 1.88 2.685(7) 160.0 . yes
O1C H1C O2C 0.84 2.01 2.724(6) 142.3 . yes
O2C H2C O2A 0.84 1.94 2.696(6) 148.4 1_655 yes

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2419978'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2025-01-27 deposited with the CCDC.	2025-03-21 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2019/2

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Lucia Trevisan'
_cambridge_user_crsid            lt459
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             LT-262
_cambridge_data_id               CH_B1_0045
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N O4'
_chemical_formula_sum            'C11 H15 N O4'
_chemical_formula_weight         225.24

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   13.7547(6)
_cell_length_b                   19.2286(9)
_cell_length_c                   8.4326(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2230.28(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2518
_cell_measurement_theta_min      3.95
_cell_measurement_theta_max      66.09

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.856
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6222
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17509
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.951
_diffrn_reflns_theta_max         66.639
_diffrn_reflns_theta_full        66.639
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1964
_reflns_number_gt                1550
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.

#===============================================================================
INTENSITY STATISTICS FOR DATASET # 1  CH_B1_0045_0m.hkl
#===============================================================================
 Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 3.94      36     37     97.3     3.41     84.64   20.38  0.0123  0.0269
 3.94 - 2.51      78     78    100.0     5.03     46.86   31.42  0.0227  0.0235
 2.51 - 1.91     119    119    100.0     7.24     22.42   33.22  0.0320  0.0201
 1.91 - 1.66     107    107    100.0     9.45     15.32   30.35  0.0393  0.0185
 1.66 - 1.49     115    115    100.0    11.82      6.88   23.88  0.0626  0.0249
 1.49 - 1.37     120    120    100.0    12.36      6.65   24.13  0.0700  0.0268
 1.37 - 1.29     107    107    100.0    12.09      4.66   20.72  0.0863  0.0335
 1.29 - 1.21     126    126    100.0    11.70      4.77   19.02  0.0997  0.0354
 1.21 - 1.16     107    107    100.0    11.34      6.61   21.34  0.0765  0.0288
 1.16 - 1.11     122    122    100.0    10.55      4.42   17.67  0.1036  0.0390
 1.11 - 1.07     106    106    100.0    10.63      3.38   12.58  0.1335  0.0493
 1.07 - 1.04     104    104    100.0    10.17      2.26   11.10  0.1729  0.0615
 1.04 - 1.00     145    145    100.0     9.34      2.15   11.01  0.1762  0.0676
 1.00 - 0.98      84     84    100.0     7.40      1.71    9.30  0.1994  0.0827
 0.98 - 0.95     129    129    100.0     6.60      2.13   10.45  0.1329  0.0664
 0.95 - 0.93      99     99    100.0     6.00      1.08    6.83  0.1918  0.1133
 0.93 - 0.91     109    109    100.0     5.98      1.06    6.52  0.1974  0.1128
 0.91 - 0.89     128    128    100.0     5.54      0.82    5.17  0.2370  0.1458
 0.89 - 0.87     123    123    100.0     5.54      0.68    5.46  0.2724  0.1487
 0.87 - 0.85     141    141    100.0     4.69      0.73    5.54  0.2226  0.1471
 0.85 - 0.84      71     74     95.9     4.00      0.75    5.61  0.2340  0.1497
#-------------------------------------------------------------------------------
 0.94 - 0.84     625    628     99.5     5.28      0.81    5.66  0.2282  0.1385
  Inf - 0.84    2276   2280     99.8     8.38      7.40   15.46  0.0684  0.0315
#===============================================================================
;

_computing_data_collection       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_refine_special_details          
;
H atoms of the OH groups are located and refined freely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.8307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_number_reflns         1964
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045

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 0.40722(10) 0.69367(7) 0.55662(18) 0.0463(4) Uani 1 1 d . . . . .
H1 H 0.348(2) 0.6901(15) 0.511(4) 0.092(10) Uiso 1 1 d . . . . .
O2 O 0.26570(11) 0.65508(8) 0.3570(2) 0.0601(5) Uani 1 1 d . . . . .
H2 H 0.240(2) 0.6131(17) 0.356(4) 0.100(10) Uiso 1 1 d . . . . .
O3 O 0.69911(14) 0.46712(9) 0.3343(3) 0.0830(6) Uani 1 1 d . . . . .
O4 O 0.63179(14) 0.49220(10) 0.1085(2) 0.0855(7) Uani 1 1 d . . . . .
N1 N 0.63986(15) 0.49971(10) 0.2537(3) 0.0619(6) Uani 1 1 d . . . . .
C1 C 0.46456(12) 0.64612(8) 0.4827(2) 0.0323(4) Uani 1 1 d . . . . .
C2 C 0.43685(13) 0.62162(9) 0.3324(2) 0.0372(4) Uani 1 1 d . . . . .
C3 C 0.49417(15) 0.57296(10) 0.2573(2) 0.0421(5) Uani 1 1 d . . . . .
H3A H 0.476880 0.555564 0.155684 0.050 Uiso 1 1 calc R U . . .
C4 C 0.57709(14) 0.55006(9) 0.3326(2) 0.0400(5) Uani 1 1 d . . . . .
C5 C 0.60542(13) 0.57464(8) 0.4794(2) 0.0347(4) Uani 1 1 d . . . . .
H5A H 0.662942 0.557083 0.527222 0.042 Uiso 1 1 calc R U . . .
C6 C 0.55077(11) 0.62477(8) 0.55810(19) 0.0288(4) Uani 1 1 d . . . . .
C7 C 0.34778(16) 0.65228(12) 0.2535(3) 0.0578(6) Uani 1 1 d . . . . .
H7A H 0.363117 0.699890 0.216512 0.069 Uiso 1 1 calc R U . . .
H7B H 0.331018 0.623933 0.159431 0.069 Uiso 1 1 calc R U . . .
C8 C 0.58496(13) 0.65634(9) 0.7156(2) 0.0332(4) Uani 1 1 d . . . . .
C9 C 0.50945(16) 0.64360(11) 0.8464(2) 0.0511(6) Uani 1 1 d . . . . .
H9A H 0.447419 0.664752 0.815720 0.077 Uiso 1 1 calc R U . . .
H9B H 0.532158 0.664461 0.945761 0.077 Uiso 1 1 calc R U . . .
H9C H 0.500558 0.593455 0.861240 0.077 Uiso 1 1 calc R U . . .
C10 C 0.60168(14) 0.73480(9) 0.6944(2) 0.0389(5) Uani 1 1 d . . . . .
H10A H 0.540315 0.757272 0.665101 0.058 Uiso 1 1 calc R U . . .
H10B H 0.649831 0.742497 0.610602 0.058 Uiso 1 1 calc R U . . .
H10C H 0.625565 0.754678 0.794117 0.058 Uiso 1 1 calc R U . . .
C11 C 0.68123(15) 0.62436(11) 0.7707(3) 0.0512(5) Uani 1 1 d . . . . .
H11A H 0.731210 0.632232 0.689888 0.077 Uiso 1 1 calc R U . . .
H11B H 0.672684 0.574268 0.787012 0.077 Uiso 1 1 calc R U . . .
H11C H 0.701365 0.646124 0.870561 0.077 Uiso 1 1 calc R U . . .


_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 1.359(2) . ?
O1 H1 0.90(3) . ?
O2 C7 1.428(3) . ?
O2 H2 0.88(3) . ?
O3 N1 1.233(3) . ?
O4 N1 1.238(3) . ?
N1 C4 1.458(3) . ?
C1 C2 1.405(2) . ?
C1 C6 1.407(2) . ?
C2 C3 1.378(3) . ?
C2 C7 1.514(3) . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(3) . ?
C5 C6 1.391(2) . ?
C5 H5A 0.9500 . ?
C6 C8 1.534(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C11 1.532(3) . ?
C8 C9 1.534(3) . ?
C8 C10 1.537(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 105.9(19) . . ?
C7 O2 H2 106(2) . . ?
O3 N1 O4 123.1(2) . . ?
O3 N1 C4 118.5(2) . . ?
O4 N1 C4 118.4(2) . . ?
O1 C1 C2 118.81(16) . . ?
O1 C1 C6 118.58(15) . . ?
C2 C1 C6 122.59(16) . . ?
C3 C2 C1 119.16(17) . . ?
C3 C2 C7 121.71(18) . . ?
C1 C2 C7 119.04(18) . . ?
C4 C3 C2 118.61(17) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 122.51(17) . . ?
C3 C4 N1 119.47(19) . . ?
C5 C4 N1 117.98(19) . . ?
C4 C5 C6 120.81(17) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 116.24(15) . . ?
C5 C6 C8 121.44(15) . . ?
C1 C6 C8 122.28(15) . . ?
O2 C7 C2 112.73(17) . . ?
O2 C7 H7A 109.0 . . ?
C2 C7 H7A 109.0 . . ?
O2 C7 H7B 109.0 . . ?
C2 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C11 C8 C9 107.64(16) . . ?
C11 C8 C6 111.63(15) . . ?
C9 C8 C6 110.59(14) . . ?
C11 C8 C10 107.46(15) . . ?
C9 C8 C10 109.98(15) . . ?
C6 C8 C10 109.49(14) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O1 C1 C2 C3 -179.44(15) . . . . ?
C6 C1 C2 C3 2.3(2) . . . . ?
O1 C1 C2 C7 3.8(2) . . . . ?
C6 C1 C2 C7 -174.42(16) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C7 C2 C3 C4 176.52(16) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C2 C3 C4 N1 -178.68(16) . . . . ?
O3 N1 C4 C3 -162.43(18) . . . . ?
O4 N1 C4 C3 18.3(3) . . . . ?
O3 N1 C4 C5 19.6(3) . . . . ?
O4 N1 C4 C5 -159.70(17) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
N1 C4 C5 C6 177.44(16) . . . . ?
C4 C5 C6 C1 2.5(2) . . . . ?
C4 C5 C6 C8 -175.63(15) . . . . ?
O1 C1 C6 C5 178.30(15) . . . . ?
C2 C1 C6 C5 -3.4(2) . . . . ?
O1 C1 C6 C8 -3.6(2) . . . . ?
C2 C1 C6 C8 174.67(15) . . . . ?
C3 C2 C7 O2 135.11(19) . . . . ?
C1 C2 C7 O2 -48.3(2) . . . . ?
C5 C6 C8 C11 -1.5(2) . . . . ?
C1 C6 C8 C11 -179.47(16) . . . . ?
C5 C6 C8 C9 -121.27(18) . . . . ?
C1 C6 C8 C9 60.7(2) . . . . ?
C5 C6 C8 C10 117.40(17) . . . . ?
C1 C6 C8 C10 -60.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.90(3) 1.85(3) 2.678(2) 152(3) . yes
O2 H2 O3 0.88(3) 2.30(3) 2.994(2) 136(3) 4_465 yes
O2 H2 O4 0.88(3) 2.53(3) 3.391(3) 165(3) 4_465 yes

