# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_170407_s1_mz
_database_code_depnum_ccdc_archive 'CCDC 1578461'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H16 O2'
_chemical_formula_sum            'C12 H16 O2'
_chemical_formula_weight         192.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.4159(7)
_cell_length_b                   16.6808(9)
_cell_length_c                   17.3970(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.212(4)
_cell_angle_gamma                90
_cell_volume                     4295.8(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5127
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9120
_cell_measurement_theta_min      3.4400
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20240
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.946
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   21.20   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00   51.50   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   57.0000   60.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   21.00   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -72.00    1.80   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -38.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -55.00  -11.80   0.9000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000  120.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0141623000
_diffrn_orient_matrix_UB_12      -0.0377037000
_diffrn_orient_matrix_UB_13      -0.0110355000
_diffrn_orient_matrix_UB_21      0.0432894000
_diffrn_orient_matrix_UB_22      0.0161763000
_diffrn_orient_matrix_UB_23      0.0027352000
_diffrn_orient_matrix_UB_31      0.0147751000
_diffrn_orient_matrix_UB_32      -0.0111857000
_diffrn_orient_matrix_UB_33      0.0409293000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5293
_reflns_number_total             8766
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         8766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          ?
_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.a Ternary CH refined with riding coordinates:
 C5A(H5A), C5B(H5B), C5C(H5C), C5D(H5D)
2.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C6B(H6BA,H6BB), C7B(H7BA,
 H7BB), C8B(H8BA,H8BB), C6C(H6CA,H6CB), C7C(H7CA,H7CB), C8C(H8CA,H8CB),
 C6D(H6DA,H6DB), C7D(H7DA,H7DB), C8D(H8DA,H8DB)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C10A(H10A), C3B(H3B), C10B(H10B), C3C(H3C), C10C(H10C), C3D(H3D),
 C10D(H10D)
2.d Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C), C11B(H11D,H11E,H11F), C12B(H12D,
 H12E,H12F), C11C(H11G,H11H,H11I), C12C(H12G,H12H,H12I), C11D(H11J,H11K,H11L),
 C12D(H12J,H12K,H12L)
2.e Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O2B(H2B), O2C(H2C), O2D(H2D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.24554(8) 0.66516(10) 0.12159(6) 0.0718(4) Uani 1 1 d . . . . .
O2A O 0.35656(8) 0.65360(10) 0.02683(7) 0.0715(4) Uani 1 1 d . . . . .
H2A H 0.3639 0.6814 0.0670 0.107 Uiso 1 1 calc GR . . . .
C1A C 0.21180(12) 0.64181(11) 0.05261(9) 0.0463(4) Uani 1 1 d . . . . .
C2A C 0.26797(11) 0.63407(11) -0.00169(9) 0.0463(4) Uani 1 1 d . . . . .
C3A C 0.23328(12) 0.60633(12) -0.07571(10) 0.0545(5) Uani 1 1 d . . . . .
H3A H 0.2718 0.6019 -0.1082 0.065 Uiso 1 1 calc R . . . .
C4A C 0.13750(11) 0.58186(11) -0.11021(9) 0.0458(4) Uani 1 1 d . . . . .
C5A C 0.09357(12) 0.63420(12) -0.18652(9) 0.0507(5) Uani 1 1 d . . . . .
H5A H 0.0999 0.6903 -0.1693 0.061 Uiso 1 1 calc R . . . .
C6A C -0.00703(13) 0.61785(13) -0.21884(10) 0.0634(6) Uani 1 1 d . . . . .
H6AA H -0.0322 0.6535 -0.2636 0.076 Uiso 1 1 calc R . . . .
H6AB H -0.0157 0.5632 -0.2387 0.076 Uiso 1 1 calc R . . . .
C7A C -0.05785(13) 0.62927(15) -0.15695(11) 0.0706(6) Uani 1 1 d . . . . .
H7AA H -0.1208 0.6149 -0.1799 0.085 Uiso 1 1 calc R . . . .
H7AB H -0.0553 0.6852 -0.1413 0.085 Uiso 1 1 calc R . . . .
C8A C -0.01779(12) 0.57794(14) -0.08375(10) 0.0650(6) Uani 1 1 d . . . . .
H8AA H -0.0473 0.5901 -0.0426 0.078 Uiso 1 1 calc R . . . .
H8AB H -0.0277 0.5217 -0.0977 0.078 Uiso 1 1 calc R . . . .
C9A C 0.08178(11) 0.59407(10) -0.05249(9) 0.0459(4) Uani 1 1 d . . . . .
C10A C 0.11771(11) 0.62173(11) 0.02145(9) 0.0495(5) Uani 1 1 d . . . . .
H10A H 0.0801 0.6284 0.0545 0.059 Uiso 1 1 calc R . . . .
C11A C 0.13648(15) 0.49203(12) -0.13236(12) 0.0797(7) Uani 1 1 d . . . . .
H11A H 0.1540 0.4605 -0.0843 0.120 Uiso 1 1 calc GR . . . .
H11B H 0.1781 0.4828 -0.1634 0.120 Uiso 1 1 calc GR . . . .
H11C H 0.0767 0.4770 -0.1631 0.120 Uiso 1 1 calc GR . . . .
C12A C 0.14022(15) 0.62599(17) -0.25270(10) 0.0876(8) Uani 1 1 d . . . . .
H12A H 0.2031 0.6388 -0.2318 0.131 Uiso 1 1 calc GR . . . .
H12B H 0.1129 0.6621 -0.2956 0.131 Uiso 1 1 calc GR . . . .
H12C H 0.1340 0.5719 -0.2724 0.131 Uiso 1 1 calc GR . . . .
O1B O 0.42308(8) 0.77452(9) 0.14654(6) 0.0652(4) Uani 1 1 d . . . . .
O2B O 0.34472(8) 0.73328(9) 0.26266(6) 0.0632(4) Uani 1 1 d . . . . .
H2B H 0.3299 0.7219 0.2149 0.095 Uiso 1 1 calc GR . . . .
C1B C 0.45126(11) 0.80750(11) 0.21238(9) 0.0447(4) Uani 1 1 d . . . . .
C2B C 0.41301(10) 0.78754(11) 0.27783(9) 0.0433(4) Uani 1 1 d . . . . .
C3B C 0.44501(11) 0.82056(11) 0.34971(9) 0.0463(4) Uani 1 1 d . . . . .
H3B H 0.4196 0.8047 0.3899 0.056 Uiso 1 1 calc R . . . .
C4B C 0.51867(11) 0.88117(11) 0.37044(9) 0.0441(4) Uani 1 1 d . . . . .
C5B C 0.59875(11) 0.84891(11) 0.44113(9) 0.0517(5) Uani 1 1 d . . . . .
H5B H 0.6189 0.7987 0.4224 0.062 Uiso 1 1 calc R . . . .
C6B C 0.67901(13) 0.90477(13) 0.46017(12) 0.0706(6) Uani 1 1 d . . . . .
H6BA H 0.7277 0.8809 0.5017 0.085 Uiso 1 1 calc R . . . .
H6BB H 0.6624 0.9547 0.4809 0.085 Uiso 1 1 calc R . . . .
C7B C 0.71237(12) 0.92260(14) 0.38819(13) 0.0755(7) Uani 1 1 d . . . . .
H7BA H 0.7363 0.8740 0.3713 0.091 Uiso 1 1 calc R . . . .
H7BB H 0.7609 0.9616 0.4027 0.091 Uiso 1 1 calc R . . . .
C8B C 0.63578(12) 0.95544(13) 0.31860(12) 0.0662(6) Uani 1 1 d . . . . .
H8BA H 0.6179 1.0081 0.3324 0.079 Uiso 1 1 calc R . . . .
H8BB H 0.6568 0.9608 0.2713 0.079 Uiso 1 1 calc R . . . .
C9B C 0.55645(11) 0.89995(11) 0.30141(10) 0.0466(4) Uani 1 1 d . . . . .
C10B C 0.52368(11) 0.86527(11) 0.22991(10) 0.0491(5) Uani 1 1 d . . . . .
H10B H 0.5491 0.8792 0.1891 0.059 Uiso 1 1 calc R . . . .
C11B C 0.47783(12) 0.95843(12) 0.39598(10) 0.0583(5) Uani 1 1 d . . . . .
H11D H 0.5241 0.9985 0.4121 0.087 Uiso 1 1 calc GR . . . .
H11E H 0.4538 0.9465 0.4400 0.087 Uiso 1 1 calc GR . . . .
H11F H 0.4304 0.9781 0.3517 0.087 Uiso 1 1 calc GR . . . .
C12B C 0.57248(14) 0.82862(14) 0.51704(10) 0.0742(7) Uani 1 1 d . . . . .
H12D H 0.5530 0.8764 0.5381 0.111 Uiso 1 1 calc GR . . . .
H12E H 0.6237 0.8065 0.5561 0.111 Uiso 1 1 calc GR . . . .
H12F H 0.5242 0.7902 0.5048 0.111 Uiso 1 1 calc GR . . . .
O1C O 0.00914(8) 0.18915(9) 0.34661(6) 0.0606(4) Uani 1 1 d . . . . .
O2C O 0.12168(7) 0.18298(9) 0.25240(6) 0.0603(4) Uani 1 1 d . . . . .
H2C H 0.1289 0.2041 0.2963 0.091 Uiso 1 1 calc GR . . . .
C1C C -0.02254(11) 0.16383(10) 0.27779(9) 0.0424(4) Uani 1 1 d . . . . .
C2C C 0.03459(10) 0.15890(11) 0.22371(9) 0.0429(4) Uani 1 1 d . . . . .
C3C C 0.00175(11) 0.13088(12) 0.14941(9) 0.0487(5) Uani 1 1 d . . . . .
H3C H 0.0409 0.1286 0.1174 0.058 Uiso 1 1 calc R . . . .
C4C C -0.09221(11) 0.10316(11) 0.11398(8) 0.0417(4) Uani 1 1 d . . . . .
C5C C -0.13875(11) 0.15814(11) 0.04037(9) 0.0461(4) Uani 1 1 d . . . . .
H5C H -0.1342 0.2134 0.0602 0.055 Uiso 1 1 calc R . . . .
C6C C -0.23915(12) 0.13976(13) 0.00708(10) 0.0594(5) Uani 1 1 d . . . . .
H6CA H -0.2656 0.1775 -0.0354 0.071 Uiso 1 1 calc R . . . .
H6CB H -0.2461 0.0864 -0.0160 0.071 Uiso 1 1 calc R . . . .
C7C C -0.29000(12) 0.14429(15) 0.06976(11) 0.0710(6) Uani 1 1 d . . . . .
H7CA H -0.3523 0.1283 0.0462 0.085 Uiso 1 1 calc R . . . .
H7CB H -0.2898 0.1991 0.0884 0.085 Uiso 1 1 calc R . . . .
C8C C -0.24711(12) 0.09004(14) 0.14000(10) 0.0625(6) Uani 1 1 d . . . . .
H8CA H -0.2771 0.0972 0.1817 0.075 Uiso 1 1 calc R . . . .
H8CB H -0.2539 0.0345 0.1229 0.075 Uiso 1 1 calc R . . . .
C9C C -0.14866(11) 0.11003(11) 0.17205(9) 0.0440(4) Uani 1 1 d . . . . .
C10C C -0.11467(11) 0.13796(12) 0.24650(9) 0.0489(5) Uani 1 1 d . . . . .
H10C H -0.1525 0.1408 0.2797 0.059 Uiso 1 1 calc R . . . .
C11C C -0.08913(14) 0.01525(12) 0.08752(10) 0.0615(5) Uani 1 1 d . . . . .
H11G H -0.0689 -0.0183 0.1339 0.092 Uiso 1 1 calc GR . . . .
H11H H -0.0482 0.0105 0.0551 0.092 Uiso 1 1 calc GR . . . .
H11I H -0.1484 -0.0012 0.0571 0.092 Uiso 1 1 calc GR . . . .
C12C C -0.09227(13) 0.15586(14) -0.02617(9) 0.0662(6) Uani 1 1 d . . . . .
H12G H -0.0298 0.1699 -0.0048 0.099 Uiso 1 1 calc GR . . . .
H12H H -0.1210 0.1933 -0.0673 0.099 Uiso 1 1 calc GR . . . .
H12I H -0.0968 0.1028 -0.0484 0.099 Uiso 1 1 calc GR . . . .
O1D O 0.19768(9) 0.28488(10) 0.38570(7) 0.0721(4) Uani 1 1 d . . . . .
O2D O 0.12133(8) 0.23280(9) 0.49944(6) 0.0624(4) Uani 1 1 d . . . . .
H2D H 0.1037 0.2273 0.4507 0.094 Uiso 1 1 calc GR . . . .
C1D C 0.22739(11) 0.31283(12) 0.45385(9) 0.0485(5) Uani 1 1 d . . . . .
C2D C 0.18917(11) 0.28757(11) 0.51811(9) 0.0450(4) Uani 1 1 d . . . . .
C3D C 0.22190(10) 0.31625(11) 0.59198(9) 0.0448(4) Uani 1 1 d . . . . .
H3D H 0.1978 0.2963 0.6315 0.054 Uiso 1 1 calc R . . . .
C4D C 0.29449(11) 0.37802(11) 0.61597(9) 0.0427(4) Uani 1 1 d . . . . .
C5D C 0.37483(11) 0.34527(11) 0.68628(9) 0.0466(4) Uani 1 1 d . . . . .
H5D H 0.3944 0.2949 0.6673 0.056 Uiso 1 1 calc R . . . .
C6D C 0.45617(12) 0.40093(13) 0.70542(11) 0.0606(5) Uani 1 1 d . . . . .
H6DA H 0.4404 0.4505 0.7274 0.073 Uiso 1 1 calc R . . . .
H6DB H 0.5051 0.3762 0.7461 0.073 Uiso 1 1 calc R . . . .
C7D C 0.48869(12) 0.42001(14) 0.63321(12) 0.0698(6) Uani 1 1 d . . . . .
H7DA H 0.5098 0.3714 0.6137 0.084 Uiso 1 1 calc R . . . .
H7DB H 0.5388 0.4574 0.6482 0.084 Uiso 1 1 calc R . . . .
C8D C 0.41191(12) 0.45651(13) 0.56733(11) 0.0650(6) Uani 1 1 d . . . . .
H8DA H 0.3946 0.5077 0.5850 0.078 Uiso 1 1 calc R . . . .
H8DB H 0.4319 0.4656 0.5199 0.078 Uiso 1 1 calc R . . . .
C9D C 0.33246(11) 0.40084(11) 0.54790(10) 0.0474(4) Uani 1 1 d . . . . .
C10D C 0.29990(11) 0.37000(12) 0.47481(10) 0.0519(5) Uani 1 1 d . . . . .
H10D H 0.3256 0.3865 0.4350 0.062 Uiso 1 1 calc R . . . .
C11D C 0.25183(13) 0.45269(12) 0.64385(11) 0.0604(5) Uani 1 1 d . . . . .
H11J H 0.2978 0.4922 0.6641 0.091 Uiso 1 1 calc GR . . . .
H11K H 0.2251 0.4376 0.6853 0.091 Uiso 1 1 calc GR . . . .
H11L H 0.2062 0.4746 0.5994 0.091 Uiso 1 1 calc GR . . . .
C12D C 0.34755(13) 0.32503(14) 0.76181(10) 0.0656(6) Uani 1 1 d . . . . .
H12J H 0.3288 0.3730 0.7831 0.098 Uiso 1 1 calc GR . . . .
H12K H 0.3981 0.3020 0.8009 0.098 Uiso 1 1 calc GR . . . .
H12L H 0.2985 0.2873 0.7490 0.098 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.2304(18) . ?
O2A H2A 0.8200 . ?
O2A C2A 1.3560(18) . ?
C1A C2A 1.454(2) . ?
C1A C10A 1.439(2) . ?
C2A C3A 1.332(2) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.487(2) . ?
C4A C5A 1.575(2) . ?
C4A C9A 1.506(2) . ?
C4A C11A 1.546(3) . ?
C5A H5A 0.9800 . ?
C5A C6A 1.519(2) . ?
C5A C12A 1.524(2) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A C7A 1.510(2) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A C8A 1.516(3) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.503(2) . ?
C9A C10A 1.333(2) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
O1B C1B 1.2352(18) . ?
O2B H2B 0.8200 . ?
O2B C2B 1.3572(19) . ?
C1B C2B 1.459(2) . ?
C1B C10B 1.442(2) . ?
C2B C3B 1.329(2) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.488(2) . ?
C4B C5B 1.574(2) . ?
C4B C9B 1.507(2) . ?
C4B C11B 1.553(2) . ?
C5B H5B 0.9800 . ?
C5B C6B 1.510(3) . ?
C5B C12B 1.524(3) . ?
C6B H6BA 0.9700 . ?
C6B H6BB 0.9700 . ?
C6B C7B 1.510(3) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C7B C8B 1.537(3) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C8B C9B 1.496(2) . ?
C9B C10B 1.336(2) . ?
C10B H10B 0.9300 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
O1C C1C 1.2344(17) . ?
O2C H2C 0.8200 . ?
O2C C2C 1.3560(18) . ?
C1C C2C 1.460(2) . ?
C1C C10C 1.438(2) . ?
C2C C3C 1.334(2) . ?
C3C H3C 0.9300 . ?
C3C C4C 1.481(2) . ?
C4C C5C 1.576(2) . ?
C4C C9C 1.511(2) . ?
C4C C11C 1.542(2) . ?
C5C H5C 0.9800 . ?
C5C C6C 1.525(2) . ?
C5C C12C 1.522(2) . ?
C6C H6CA 0.9700 . ?
C6C H6CB 0.9700 . ?
C6C C7C 1.512(2) . ?
C7C H7CA 0.9700 . ?
C7C H7CB 0.9700 . ?
C7C C8C 1.516(3) . ?
C8C H8CA 0.9700 . ?
C8C H8CB 0.9700 . ?
C8C C9C 1.501(2) . ?
C9C C10C 1.338(2) . ?
C10C H10C 0.9300 . ?
C11C H11G 0.9600 . ?
C11C H11H 0.9600 . ?
C11C H11I 0.9600 . ?
C12C H12G 0.9600 . ?
C12C H12H 0.9600 . ?
C12C H12I 0.9600 . ?
O1D C1D 1.2368(19) . ?
O2D H2D 0.8200 . ?
O2D C2D 1.358(2) . ?
C1D C2D 1.464(2) . ?
C1D C10D 1.437(2) . ?
C2D C3D 1.332(2) . ?
C3D H3D 0.9300 . ?
C3D C4D 1.492(2) . ?
C4D C5D 1.576(2) . ?
C4D C9D 1.509(2) . ?
C4D C11D 1.548(2) . ?
C5D H5D 0.9800 . ?
C5D C6D 1.521(2) . ?
C5D C12D 1.525(2) . ?
C6D H6DA 0.9700 . ?
C6D H6DB 0.9700 . ?
C6D C7D 1.511(3) . ?
C7D H7DA 0.9700 . ?
C7D H7DB 0.9700 . ?
C7D C8D 1.526(3) . ?
C8D H8DA 0.9700 . ?
C8D H8DB 0.9700 . ?
C8D C9D 1.499(2) . ?
C9D C10D 1.333(2) . ?
C10D H10D 0.9300 . ?
C11D H11J 0.9600 . ?
C11D H11K 0.9600 . ?
C11D H11L 0.9600 . ?
C12D H12J 0.9600 . ?
C12D H12K 0.9600 . ?
C12D H12L 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A O2A H2A 109.5 . . ?
O1A C1A C2A 119.69(16) . . ?
O1A C1A C10A 123.24(16) . . ?
C10A C1A C2A 117.07(14) . . ?
O2A C2A C1A 117.55(13) . . ?
C3A C2A O2A 121.92(16) . . ?
C3A C2A C1A 120.50(16) . . ?
C2A C3A H3A 117.6 . . ?
C2A C3A C4A 124.82(16) . . ?
C4A C3A H3A 117.6 . . ?
C3A C4A C5A 109.44(15) . . ?
C3A C4A C9A 112.36(13) . . ?
C3A C4A C11A 107.84(16) . . ?
C9A C4A C5A 107.20(14) . . ?
C9A C4A C11A 109.22(16) . . ?
C11A C4A C5A 110.80(13) . . ?
C4A C5A H5A 106.8 . . ?
C6A C5A C4A 111.51(15) . . ?
C6A C5A H5A 106.8 . . ?
C6A C5A C12A 110.63(14) . . ?
C12A C5A C4A 113.84(16) . . ?
C12A C5A H5A 106.8 . . ?
C5A C6A H6AA 109.0 . . ?
C5A C6A H6AB 109.0 . . ?
H6AA C6A H6AB 107.8 . . ?
C7A C6A C5A 113.12(14) . . ?
C7A C6A H6AA 109.0 . . ?
C7A C6A H6AB 109.0 . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
C6A C7A C8A 110.92(17) . . ?
H7AA C7A H7AB 108.0 . . ?
C8A C7A H7AA 109.5 . . ?
C8A C7A H7AB 109.5 . . ?
C7A C8A H8AA 109.7 . . ?
C7A C8A H8AB 109.7 . . ?
H8AA C8A H8AB 108.2 . . ?
C9A C8A C7A 109.77(15) . . ?
C9A C8A H8AA 109.7 . . ?
C9A C8A H8AB 109.7 . . ?
C8A C9A C4A 116.71(13) . . ?
C10A C9A C4A 121.97(15) . . ?
C10A C9A C8A 121.23(16) . . ?
C1A C10A H10A 118.4 . . ?
C9A C10A C1A 123.20(16) . . ?
C9A C10A H10A 118.4 . . ?
C4A C11A H11A 109.5 . . ?
C4A C11A H11B 109.5 . . ?
C4A C11A H11C 109.5 . . ?
H11A C11A H11B 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C5A C12A H12A 109.5 . . ?
C5A C12A H12B 109.5 . . ?
C5A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C2B O2B H2B 109.5 . . ?
O1B C1B C2B 120.52(16) . . ?
O1B C1B C10B 123.03(16) . . ?
C10B C1B C2B 116.43(14) . . ?
O2B C2B C1B 117.44(13) . . ?
C3B C2B O2B 121.56(15) . . ?
C3B C2B C1B 121.00(16) . . ?
C2B C3B H3B 117.7 . . ?
C2B C3B C4B 124.58(16) . . ?
C4B C3B H3B 117.7 . . ?
C3B C4B C5B 109.64(15) . . ?
C3B C4B C9B 112.76(13) . . ?
C3B C4B C11B 106.88(14) . . ?
C9B C4B C5B 107.49(13) . . ?
C9B C4B C11B 109.47(15) . . ?
C11B C4B C5B 110.63(13) . . ?
C4B C5B H5B 106.5 . . ?
C6B C5B C4B 112.10(16) . . ?
C6B C5B H5B 106.5 . . ?
C6B C5B C12B 110.29(15) . . ?
C12B C5B C4B 114.38(14) . . ?
C12B C5B H5B 106.5 . . ?
C5B C6B H6BA 109.0 . . ?
C5B C6B H6BB 109.0 . . ?
C5B C6B C7B 112.80(15) . . ?
H6BA C6B H6BB 107.8 . . ?
C7B C6B H6BA 109.0 . . ?
C7B C6B H6BB 109.0 . . ?
C6B C7B H7BA 109.4 . . ?
C6B C7B H7BB 109.4 . . ?
C6B C7B C8B 111.03(16) . . ?
H7BA C7B H7BB 108.0 . . ?
C8B C7B H7BA 109.4 . . ?
C8B C7B H7BB 109.4 . . ?
C7B C8B H8BA 109.7 . . ?
C7B C8B H8BB 109.7 . . ?
H8BA C8B H8BB 108.2 . . ?
C9B C8B C7B 110.03(17) . . ?
C9B C8B H8BA 109.7 . . ?
C9B C8B H8BB 109.7 . . ?
C8B C9B C4B 116.47(14) . . ?
C10B C9B C4B 121.47(16) . . ?
C10B C9B C8B 121.96(17) . . ?
C1B C10B H10B 118.1 . . ?
C9B C10B C1B 123.74(16) . . ?
C9B C10B H10B 118.1 . . ?
C4B C11B H11D 109.5 . . ?
C4B C11B H11E 109.5 . . ?
C4B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C5B C12B H12D 109.5 . . ?
C5B C12B H12E 109.5 . . ?
C5B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C2C O2C H2C 109.5 . . ?
O1C C1C C2C 119.86(15) . . ?
O1C C1C C10C 123.47(15) . . ?
C10C C1C C2C 116.68(13) . . ?
O2C C2C C1C 117.37(13) . . ?
C3C C2C O2C 121.96(15) . . ?
C3C C2C C1C 120.67(15) . . ?
C2C C3C H3C 117.4 . . ?
C2C C3C C4C 125.11(15) . . ?
C4C C3C H3C 117.4 . . ?
C3C C4C C5C 109.09(14) . . ?
C3C C4C C9C 112.15(12) . . ?
C3C C4C C11C 108.25(15) . . ?
C9C C4C C5C 106.42(13) . . ?
C9C C4C C11C 110.08(15) . . ?
C11C C4C C5C 110.85(12) . . ?
C4C C5C H5C 106.8 . . ?
C6C C5C C4C 112.04(15) . . ?
C6C C5C H5C 106.8 . . ?
C12C C5C C4C 113.53(15) . . ?
C12C C5C H5C 106.8 . . ?
C12C C5C C6C 110.46(13) . . ?
C5C C6C H6CA 109.0 . . ?
C5C C6C H6CB 109.0 . . ?
H6CA C6C H6CB 107.8 . . ?
C7C C6C C5C 113.07(14) . . ?
C7C C6C H6CA 109.0 . . ?
C7C C6C H6CB 109.0 . . ?
C6C C7C H7CA 109.5 . . ?
C6C C7C H7CB 109.5 . . ?
C6C C7C C8C 110.74(16) . . ?
H7CA C7C H7CB 108.1 . . ?
C8C C7C H7CA 109.5 . . ?
C8C C7C H7CB 109.5 . . ?
C7C C8C H8CA 109.8 . . ?
C7C C8C H8CB 109.8 . . ?
H8CA C8C H8CB 108.2 . . ?
C9C C8C C7C 109.57(16) . . ?
C9C C8C H8CA 109.8 . . ?
C9C C8C H8CB 109.8 . . ?
C8C C9C C4C 116.51(13) . . ?
C10C C9C C4C 122.05(15) . . ?
C10C C9C C8C 121.27(15) . . ?
C1C C10C H10C 118.3 . . ?
C9C C10C C1C 123.33(15) . . ?
C9C C10C H10C 118.3 . . ?
C4C C11C H11G 109.5 . . ?
C4C C11C H11H 109.5 . . ?
C4C C11C H11I 109.5 . . ?
H11G C11C H11H 109.5 . . ?
H11G C11C H11I 109.5 . . ?
H11H C11C H11I 109.5 . . ?
C5C C12C H12G 109.5 . . ?
C5C C12C H12H 109.5 . . ?
C5C C12C H12I 109.5 . . ?
H12G C12C H12H 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
C2D O2D H2D 109.5 . . ?
O1D C1D C2D 120.22(17) . . ?
O1D C1D C10D 123.18(17) . . ?
C10D C1D C2D 116.60(15) . . ?
O2D C2D C1D 117.29(14) . . ?
C3D C2D O2D 122.11(16) . . ?
C3D C2D C1D 120.58(17) . . ?
C2D C3D H3D 117.6 . . ?
C2D C3D C4D 124.79(16) . . ?
C4D C3D H3D 117.6 . . ?
C3D C4D C5D 110.08(14) . . ?
C3D C4D C9D 112.31(13) . . ?
C3D C4D C11D 106.99(14) . . ?
C9D C4D C5D 107.67(13) . . ?
C9D C4D C11D 109.55(15) . . ?
C11D C4D C5D 110.26(13) . . ?
C4D C5D H5D 106.5 . . ?
C6D C5D C4D 112.32(15) . . ?
C6D C5D H5D 106.5 . . ?
C6D C5D C12D 110.81(14) . . ?
C12D C5D C4D 113.55(14) . . ?
C12D C5D H5D 106.5 . . ?
C5D C6D H6DA 109.0 . . ?
C5D C6D H6DB 109.0 . . ?
H6DA C6D H6DB 107.8 . . ?
C7D C6D C5D 113.04(14) . . ?
C7D C6D H6DA 109.0 . . ?
C7D C6D H6DB 109.0 . . ?
C6D C7D H7DA 109.7 . . ?
C6D C7D H7DB 109.7 . . ?
C6D C7D C8D 109.92(15) . . ?
H7DA C7D H7DB 108.2 . . ?
C8D C7D H7DA 109.7 . . ?
C8D C7D H7DB 109.7 . . ?
C7D C8D H8DA 109.7 . . ?
C7D C8D H8DB 109.7 . . ?
H8DA C8D H8DB 108.2 . . ?
C9D C8D C7D 109.63(17) . . ?
C9D C8D H8DA 109.7 . . ?
C9D C8D H8DB 109.7 . . ?
C8D C9D C4D 116.81(15) . . ?
C10D C9D C4D 121.73(16) . . ?
C10D C9D C8D 121.38(16) . . ?
C1D C10D H10D 118.1 . . ?
C9D C10D C1D 123.87(16) . . ?
C9D C10D H10D 118.1 . . ?
C4D C11D H11J 109.5 . . ?
C4D C11D H11K 109.5 . . ?
C4D C11D H11L 109.5 . . ?
H11J C11D H11K 109.5 . . ?
H11J C11D H11L 109.5 . . ?
H11K C11D H11L 109.5 . . ?
C5D C12D H12J 109.5 . . ?
C5D C12D H12K 109.5 . . ?
C5D C12D H12L 109.5 . . ?
H12J C12D H12K 109.5 . . ?
H12J C12D H12L 109.5 . . ?
H12K C12D H12L 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
O1A C1A C2A O2A -0.2(3) . . . . ?
O1A C1A C2A C3A 177.74(18) . . . . ?
O1A C1A C10A C9A -177.85(18) . . . . ?
O2A C2A C3A C4A 178.40(18) . . . . ?
C1A C2A C3A C4A 0.6(3) . . . . ?
C2A C1A C10A C9A 2.6(3) . . . . ?
C2A C3A C4A C5A 120.6(2) . . . . ?
C2A C3A C4A C9A 1.7(3) . . . . ?
C2A C3A C4A C11A -118.8(2) . . . . ?
C3A C4A C5A C6A -173.83(15) . . . . ?
C3A C4A C5A C12A 60.1(2) . . . . ?
C3A C4A C9A C8A 174.89(16) . . . . ?
C3A C4A C9A C10A -1.8(2) . . . . ?
C4A C5A C6A C7A 55.2(2) . . . . ?
C4A C9A C10A C1A -0.3(3) . . . . ?
C5A C4A C9A C8A 54.6(2) . . . . ?
C5A C4A C9A C10A -122.05(18) . . . . ?
C5A C6A C7A C8A -55.7(2) . . . . ?
C6A C7A C8A C9A 53.6(2) . . . . ?
C7A C8A C9A C4A -56.7(2) . . . . ?
C7A C8A C9A C10A 120.0(2) . . . . ?
C8A C9A C10A C1A -176.82(17) . . . . ?
C9A C4A C5A C6A -51.72(18) . . . . ?
C9A C4A C5A C12A -177.76(16) . . . . ?
C10A C1A C2A O2A 179.36(17) . . . . ?
C10A C1A C2A C3A -2.7(3) . . . . ?
C11A C4A C5A C6A 67.4(2) . . . . ?
C11A C4A C5A C12A -58.7(2) . . . . ?
C11A C4A C9A C8A -65.5(2) . . . . ?
C11A C4A C9A C10A 117.85(19) . . . . ?
C12A C5A C6A C7A -177.02(19) . . . . ?
O1B C1B C2B O2B -1.5(2) . . . . ?
O1B C1B C2B C3B 177.59(17) . . . . ?
O1B C1B C10B C9B -178.25(18) . . . . ?
O2B C2B C3B C4B -179.09(16) . . . . ?
C1B C2B C3B C4B 1.9(3) . . . . ?
C2B C1B C10B C9B 0.3(3) . . . . ?
C2B C3B C4B C5B -121.64(18) . . . . ?
C2B C3B C4B C9B -1.9(2) . . . . ?
C2B C3B C4B C11B 118.41(18) . . . . ?
C3B C4B C5B C6B 175.07(15) . . . . ?
C3B C4B C5B C12B -58.42(19) . . . . ?
C3B C4B C9B C8B -175.30(16) . . . . ?
C3B C4B C9B C10B 1.2(2) . . . . ?
C4B C5B C6B C7B -55.3(2) . . . . ?
C4B C9B C10B C1B -0.5(3) . . . . ?
C5B C4B C9B C8B -54.3(2) . . . . ?
C5B C4B C9B C10B 122.11(18) . . . . ?
C5B C6B C7B C8B 54.9(2) . . . . ?
C6B C7B C8B C9B -53.0(2) . . . . ?
C7B C8B C9B C4B 55.9(2) . . . . ?
C7B C8B C9B C10B -120.6(2) . . . . ?
C8B C9B C10B C1B 175.80(17) . . . . ?
C9B C4B C5B C6B 52.17(18) . . . . ?
C9B C4B C5B C12B 178.69(16) . . . . ?
C10B C1B C2B O2B 179.99(15) . . . . ?
C10B C1B C2B C3B -1.0(2) . . . . ?
C11B C4B C5B C6B -67.30(19) . . . . ?
C11B C4B C5B C12B 59.2(2) . . . . ?
C11B C4B C9B C8B 65.87(19) . . . . ?
C11B C4B C9B C10B -117.68(18) . . . . ?
C12B C5B C6B C7B 176.04(17) . . . . ?
O1C C1C C2C O2C 0.0(3) . . . . ?
O1C C1C C2C C3C 179.27(17) . . . . ?
O1C C1C C10C C9C -179.54(18) . . . . ?
O2C C2C C3C C4C 179.70(17) . . . . ?
C1C C2C C3C C4C 0.4(3) . . . . ?
C2C C1C C10C C9C 0.3(3) . . . . ?
C2C C3C C4C C5C 117.66(19) . . . . ?
C2C C3C C4C C9C 0.0(3) . . . . ?
C2C C3C C4C C11C -121.6(2) . . . . ?
C3C C4C C5C C6C -172.97(14) . . . . ?
C3C C4C C5C C12C 61.04(18) . . . . ?
C3C C4C C9C C8C 175.02(16) . . . . ?
C3C C4C C9C C10C -0.3(2) . . . . ?
C4C C5C C6C C7C 54.6(2) . . . . ?
C4C C9C C10C C1C 0.1(3) . . . . ?
C5C C4C C9C C8C 55.8(2) . . . . ?
C5C C4C C9C C10C -119.52(18) . . . . ?
C5C C6C C7C C8C -55.0(2) . . . . ?
C6C C7C C8C C9C 54.3(2) . . . . ?
C7C C8C C9C C4C -58.5(2) . . . . ?
C7C C8C C9C C10C 116.83(19) . . . . ?
C8C C9C C10C C1C -174.99(18) . . . . ?
C9C C4C C5C C6C -51.77(18) . . . . ?
C9C C4C C5C C12C -177.76(14) . . . . ?
C10C C1C C2C O2C -179.91(16) . . . . ?
C10C C1C C2C C3C -0.6(3) . . . . ?
C11C C4C C5C C6C 67.92(19) . . . . ?
C11C C4C C5C C12C -58.1(2) . . . . ?
C11C C4C C9C C8C -64.4(2) . . . . ?
C11C C4C C9C C10C 120.30(19) . . . . ?
C12C C5C C6C C7C -177.75(17) . . . . ?
O1D C1D C2D O2D 0.4(3) . . . . ?
O1D C1D C2D C3D 178.75(17) . . . . ?
O1D C1D C10D C9D 179.78(18) . . . . ?
O2D C2D C3D C4D -178.25(15) . . . . ?
C1D C2D C3D C4D 3.4(3) . . . . ?
C2D C1D C10D C9D -0.7(3) . . . . ?
C2D C3D C4D C5D -124.13(17) . . . . ?
C2D C3D C4D C9D -4.2(2) . . . . ?
C2D C3D C4D C11D 116.06(18) . . . . ?
C3D C4D C5D C6D 172.06(14) . . . . ?
C3D C4D C5D C12D -61.21(19) . . . . ?
C3D C4D C9D C8D -174.24(15) . . . . ?
C3D C4D C9D C10D 2.6(2) . . . . ?
C4D C5D C6D C7D -54.4(2) . . . . ?
C4D C9D C10D C1D -0.4(3) . . . . ?
C5D C4D C9D C8D -52.9(2) . . . . ?
C5D C4D C9D C10D 123.90(18) . . . . ?
C5D C6D C7D C8D 56.8(2) . . . . ?
C6D C7D C8D C9D -55.8(2) . . . . ?
C7D C8D C9D C4D 57.5(2) . . . . ?
C7D C8D C9D C10D -119.3(2) . . . . ?
C8D C9D C10D C1D 176.26(17) . . . . ?
C9D C4D C5D C6D 49.33(18) . . . . ?
C9D C4D C5D C12D 176.06(16) . . . . ?
C10D C1D C2D O2D -179.21(16) . . . . ?
C10D C1D C2D C3D -0.8(2) . . . . ?
C11D C4D C5D C6D -70.13(18) . . . . ?
C11D C4D C5D C12D 56.6(2) . . . . ?
C11D C4D C9D C8D 67.03(19) . . . . ?
C11D C4D C9D C10D -116.18(19) . . . . ?
C12D C5D C6D C7D 177.43(16) . . . . ?

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

data_170807_s2_fj
_database_code_depnum_ccdc_archive 'CCDC 1578462'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-08-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H16 O3'
_chemical_formula_sum            'C12 H16 O3'
_chemical_formula_weight         208.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3633(6)
_cell_length_b                   8.6583(8)
_cell_length_c                   9.2145(9)
_cell_angle_alpha                95.128(8)
_cell_angle_beta                 98.931(8)
_cell_angle_gamma                111.272(8)
_cell_volume                     533.98(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1573
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6890
_cell_measurement_theta_min      3.7310
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4508
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.031
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   24.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   24.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   34.00   90.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  178.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega   60.00   89.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856 -178.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00   36.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -38.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega  -33.00   86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       16.6856    0.0000 -180.0000 119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0908274000
_diffrn_orient_matrix_UB_12      -0.0107786000
_diffrn_orient_matrix_UB_13      -0.0009902000
_diffrn_orient_matrix_UB_21      -0.0424596000
_diffrn_orient_matrix_UB_22      -0.0525915000
_diffrn_orient_matrix_UB_23      -0.0700373000
_diffrn_orient_matrix_UB_31      0.0329969000
_diffrn_orient_matrix_UB_32      0.0710267000
_diffrn_orient_matrix_UB_33      -0.0363526000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1599
_reflns_number_total             2184
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.034
_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)+(0.0443P)²+0.1150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          ?
_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.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C9(H9)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5954(2) 0.29499(14) 0.14948(15) 0.0557(4) Uani 1 1 d . . . . .
O2 O 0.4015(2) -0.41847(14) 0.12391(14) 0.0549(4) Uani 1 1 d . . . . .
H2 H 0.3958 -0.3971 0.0388 0.082 Uiso 1 1 calc GR . . . .
O3 O 0.2313(2) 0.26566(17) 0.20411(17) 0.0634(4) Uani 1 1 d . . . . .
H3 H 0.317(4) 0.346(3) 0.178(3) 0.094(9) Uiso 1 1 d . . . . .
C1 C 0.4873(3) 0.15900(18) 0.17756(17) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.5464(2) 0.01637(18) 0.18250(17) 0.0374(4) Uani 1 1 d . . . . .
H2A H 0.6715 0.0289 0.1649 0.045 Uiso 1 1 calc R . . . .
C3 C 0.4299(2) -0.13169(18) 0.21106(16) 0.0326(4) Uani 1 1 d . . . . .
C4 C 0.5125(3) -0.2678(2) 0.22685(19) 0.0418(4) Uani 1 1 d . . . . .
H4 H 0.6502 -0.2247 0.2127 0.050 Uiso 1 1 calc R . . . .
C5 C 0.5104(3) -0.3123(2) 0.3824(2) 0.0465(4) Uani 1 1 d . . . . .
H5A H 0.5470 -0.4087 0.3890 0.056 Uiso 1 1 calc R . . . .
H5B H 0.6084 -0.2190 0.4539 0.056 Uiso 1 1 calc R . . . .
C6 C 0.3083(3) -0.3518(2) 0.42135(19) 0.0431(4) Uani 1 1 d . . . . .
H6A H 0.3150 -0.3743 0.5229 0.052 Uiso 1 1 calc R . . . .
H6B H 0.2134 -0.4526 0.3566 0.052 Uiso 1 1 calc R . . . .
C7 C 0.2343(2) -0.20956(19) 0.40630(18) 0.0386(4) Uani 1 1 d . . . . .
H7 H 0.3320 -0.1105 0.4741 0.046 Uiso 1 1 calc R . . . .
C8 C 0.2268(2) -0.16320(18) 0.24471(18) 0.0352(4) Uani 1 1 d . . . . .
C9 C 0.1764(3) -0.0107(2) 0.2399(2) 0.0441(4) Uani 1 1 d . . . . .
H9 H 0.0541 -0.0186 0.2610 0.053 Uiso 1 1 calc R . . . .
C10 C 0.2919(3) 0.13485(19) 0.20811(19) 0.0415(4) Uani 1 1 d . . . . .
C11 C 0.0382(3) -0.2505(3) 0.4580(3) 0.0660(6) Uani 1 1 d . . . . .
H11A H -0.0028 -0.1574 0.4528 0.099 Uiso 1 1 calc GR . . . .
H11B H 0.0549 -0.2716 0.5588 0.099 Uiso 1 1 calc GR . . . .
H11C H -0.0613 -0.3484 0.3950 0.099 Uiso 1 1 calc GR . . . .
C12 C 0.0623(3) -0.3056(2) 0.1296(2) 0.0534(5) Uani 1 1 d . . . . .
H12A H 0.0756 -0.2826 0.0310 0.080 Uiso 1 1 calc GR . . . .
H12B H -0.0660 -0.3120 0.1453 0.080 Uiso 1 1 calc GR . . . .
H12C H 0.0752 -0.4104 0.1413 0.080 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2352(18) . ?
O2 C4 1.426(2) . ?
O3 C10 1.3607(19) . ?
C1 C2 1.453(2) . ?
C1 C10 1.453(2) . ?
C2 C3 1.334(2) . ?
C3 C4 1.517(2) . ?
C3 C8 1.507(2) . ?
C4 C5 1.518(2) . ?
C5 C6 1.509(2) . ?
C6 C7 1.526(2) . ?
C7 C8 1.574(2) . ?
C7 C11 1.519(2) . ?
C8 C9 1.498(2) . ?
C8 C12 1.548(2) . ?
C9 C10 1.328(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 122.71(16) . . ?
O1 C1 C10 120.73(15) . . ?
C2 C1 C10 116.56(13) . . ?
C3 C2 C1 123.25(15) . . ?
C2 C3 C4 119.05(14) . . ?
C2 C3 C8 122.40(13) . . ?
C8 C3 C4 118.22(12) . . ?
O2 C4 C3 113.60(14) . . ?
O2 C4 C5 107.51(13) . . ?
C3 C4 C5 109.08(13) . . ?
C6 C5 C4 111.69(14) . . ?
C5 C6 C7 112.77(13) . . ?
C6 C7 C8 111.41(13) . . ?
C11 C7 C6 110.48(13) . . ?
C11 C7 C8 113.72(15) . . ?
C3 C8 C7 106.32(12) . . ?
C3 C8 C12 111.39(14) . . ?
C9 C8 C3 111.58(12) . . ?
C9 C8 C7 109.52(13) . . ?
C9 C8 C12 106.72(13) . . ?
C12 C8 C7 111.36(13) . . ?
C10 C9 C8 125.43(16) . . ?
O3 C10 C1 118.18(14) . . ?
C9 C10 O3 121.06(16) . . ?
C9 C10 C1 120.76(14) . . ?

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 -179.23(15) . . . . ?
O1 C1 C10 O3 0.3(2) . . . . ?
O1 C1 C10 C9 -179.25(16) . . . . ?
O2 C4 C5 C6 -71.82(17) . . . . ?
C1 C2 C3 C4 -174.75(15) . . . . ?
C1 C2 C3 C8 -1.5(2) . . . . ?
C2 C1 C10 O3 -179.84(14) . . . . ?
C2 C1 C10 C9 0.6(2) . . . . ?
C2 C3 C4 O2 -121.51(16) . . . . ?
C2 C3 C4 C5 118.58(16) . . . . ?
C2 C3 C8 C7 -118.78(15) . . . . ?
C2 C3 C8 C9 0.6(2) . . . . ?
C2 C3 C8 C12 119.73(16) . . . . ?
C3 C4 C5 C6 51.78(19) . . . . ?
C3 C8 C9 C10 1.0(2) . . . . ?
C4 C3 C8 C7 54.50(17) . . . . ?
C4 C3 C8 C9 173.86(13) . . . . ?
C4 C3 C8 C12 -66.99(18) . . . . ?
C4 C5 C6 C7 -56.1(2) . . . . ?
C5 C6 C7 C8 56.89(18) . . . . ?
C5 C6 C7 C11 -175.68(15) . . . . ?
C6 C7 C8 C3 -52.77(16) . . . . ?
C6 C7 C8 C9 -173.46(13) . . . . ?
C6 C7 C8 C12 68.74(17) . . . . ?
C7 C8 C9 C10 118.41(19) . . . . ?
C8 C3 C4 O2 64.98(18) . . . . ?
C8 C3 C4 C5 -54.93(19) . . . . ?
C8 C9 C10 O3 178.88(16) . . . . ?
C8 C9 C10 C1 -1.5(3) . . . . ?
C10 C1 C2 C3 1.0(2) . . . . ?
C11 C7 C8 C3 -178.42(14) . . . . ?
C11 C7 C8 C9 60.89(18) . . . . ?
C11 C7 C8 C12 -56.91(18) . . . . ?
C12 C8 C9 C10 -120.92(19) . . . . ?

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

data_171113_s3_fj
_database_code_depnum_ccdc_archive 'CCDC 1585496'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-01-03 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H18 O3, H2 O'
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3s1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.0329(6)
_cell_length_b                   7.9949(3)
_cell_length_c                   11.4441(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.344(4)
_cell_angle_gamma                90
_cell_volume                     1364.15(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1488
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2110
_cell_measurement_theta_min      3.5810
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5658
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.117
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    1.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   85.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -19.0000 -150.0000 98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0077711000
_diffrn_orient_matrix_UB_12      -0.0228783000
_diffrn_orient_matrix_UB_13      0.0577218000
_diffrn_orient_matrix_UB_21      0.0449478000
_diffrn_orient_matrix_UB_22      -0.0282645000
_diffrn_orient_matrix_UB_23      0.0122290000
_diffrn_orient_matrix_UB_31      0.0135046000
_diffrn_orient_matrix_UB_32      0.0808994000
_diffrn_orient_matrix_UB_33      0.0206421000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1929
_reflns_number_total             2778
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.038
_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)+(0.0532P)²+0.2369P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.42980(9) 0.6881(2) 0.15354(13) 0.0682(4) Uani 1 1 d . . . . .
H1 H 0.4348(17) 0.579(3) 0.172(2) 0.096(9) Uiso 1 1 d . . . . .
O2 O 0.26853(9) 0.26139(18) -0.20817(15) 0.0763(5) Uani 1 1 d . . . . .
O3 O 0.01629(10) 0.3559(2) -0.11756(18) 0.1035(7) Uani 1 1 d . . . . .
C1 C 0.32395(11) 0.6071(2) -0.01673(15) 0.0465(4) Uani 1 1 d . . . . .
C2 C 0.40579(12) 0.7095(3) 0.02912(18) 0.0625(6) Uani 1 1 d . . . . .
H2 H 0.4562 0.6742 -0.0114 0.075 Uiso 1 1 calc R . . . .
C3 C 0.38780(16) 0.8934(3) 0.0049(2) 0.0817(7) Uani 1 1 d . . . . .
H3A H 0.4365 0.9585 0.0460 0.098 Uiso 1 1 calc R . . . .
H3B H 0.3866 0.9139 -0.0788 0.098 Uiso 1 1 calc R . . . .
C4 C 0.30045(16) 0.9516(3) 0.0429(2) 0.0725(6) Uani 1 1 d . . . . .
H4A H 0.2910 1.0681 0.0211 0.087 Uiso 1 1 calc R . . . .
H4B H 0.3044 0.9440 0.1280 0.087 Uiso 1 1 calc R . . . .
C5 C 0.22015(13) 0.8492(2) -0.01229(17) 0.0569(5) Uani 1 1 d . . . . .
H5 H 0.2177 0.8597 -0.0980 0.068 Uiso 1 1 calc R . . . .
C6 C 0.23468(11) 0.6585(2) 0.01873(14) 0.0418(4) Uani 1 1 d . . . . .
C7 C 0.15998(10) 0.5566(2) -0.04331(15) 0.0430(4) Uani 1 1 d . . . . .
H7 H 0.1023 0.5853 -0.0294 0.052 Uiso 1 1 calc R . . . .
C8 C 0.16689(10) 0.4289(2) -0.11649(15) 0.0415(4) Uani 1 1 d . . . . .
C9 C 0.25634(11) 0.3811(2) -0.14454(16) 0.0478(4) Uani 1 1 d . . . . .
C10 C 0.33107(11) 0.4822(2) -0.09166(17) 0.0529(5) Uani 1 1 d . . . . .
H10 H 0.3877 0.4579 -0.1115 0.063 Uiso 1 1 calc R . . . .
C11 C 0.13341(17) 0.9206(3) 0.0209(2) 0.0806(7) Uani 1 1 d . . . . .
H11A H 0.0837 0.8568 -0.0167 0.121 Uiso 1 1 calc GR . . . .
H11B H 0.1274 1.0350 -0.0045 0.121 Uiso 1 1 calc GR . . . .
H11C H 0.1342 0.9153 0.1048 0.121 Uiso 1 1 calc GR . . . .
C12 C 0.23127(14) 0.6281(3) 0.15188(16) 0.0500(5) Uani 1 1 d . . . . .
H12A H 0.1719(13) 0.649(2) 0.1728(16) 0.055(5) Uiso 1 1 d . . . . .
H12B H 0.2473(12) 0.503(3) 0.1710(17) 0.061(5) Uiso 1 1 d . . . . .
H12C H 0.2745(15) 0.695(3) 0.203(2) 0.077(7) Uiso 1 1 d . . . . .
C13 C 0.08214(12) 0.3384(2) -0.16478(17) 0.0512(5) Uani 1 1 d . . . . .
C14 C 0.07832(16) 0.2281(3) -0.2690(2) 0.0889(8) Uani 1 1 d . . . . .
H14A H 0.1093 0.2802 -0.3277 0.133 Uiso 1 1 calc GR . . . .
H14B H 0.0169 0.2095 -0.3007 0.133 Uiso 1 1 calc GR . . . .
H14C H 0.1063 0.1231 -0.2464 0.133 Uiso 1 1 calc GR . . . .
H4C H 0.386(2) 0.322(4) 0.233(3) 0.111(11) Uiso 1 1 d . . . . .
O4 O 0.43203(13) 0.3582(2) 0.21058(17) 0.0826(6) Uani 1 1 d . . . . .
H4D H 0.477(2) 0.308(3) 0.252(3) 0.108(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.90(3) . ?
O1 C2 1.434(2) . ?
O2 C9 1.230(2) . ?
O3 C13 1.195(2) . ?
C1 C2 1.515(2) . ?
C1 C6 1.508(2) . ?
C1 C10 1.330(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.514(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.509(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.527(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.574(3) . ?
C5 C11 1.515(3) . ?
C6 C7 1.492(2) . ?
C6 C12 1.550(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.333(2) . ?
C8 C9 1.472(2) . ?
C8 C13 1.507(2) . ?
C9 C10 1.452(3) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.967(18) . ?
C12 H12B 1.04(2) . ?
C12 H12C 0.98(2) . ?
C13 C14 1.478(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 H4C 0.82(3) . ?
O4 H4D 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 110.9(17) . . ?
C6 C1 C2 118.08(16) . . ?
C10 C1 C2 120.05(16) . . ?
C10 C1 C6 121.75(15) . . ?
O1 C2 C1 111.69(15) . . ?
O1 C2 H2 108.9 . . ?
O1 C2 C3 108.34(18) . . ?
C1 C2 H2 108.9 . . ?
C3 C2 C1 110.08(17) . . ?
C3 C2 H2 108.9 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.84(16) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C3 C4 C5 112.74(19) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C4 C5 H5 107.1 . . ?
C4 C5 C6 110.25(16) . . ?
C6 C5 H5 107.1 . . ?
C11 C5 C4 110.78(18) . . ?
C11 C5 H5 107.1 . . ?
C11 C5 C6 114.03(16) . . ?
C1 C6 C5 107.81(14) . . ?
C1 C6 C12 111.35(14) . . ?
C7 C6 C1 111.39(14) . . ?
C7 C6 C5 110.33(14) . . ?
C7 C6 C12 105.34(14) . . ?
C12 C6 C5 110.64(15) . . ?
C6 C7 H7 116.5 . . ?
C8 C7 C6 127.09(15) . . ?
C8 C7 H7 116.5 . . ?
C7 C8 C9 118.83(15) . . ?
C7 C8 C13 117.90(15) . . ?
C9 C8 C13 123.26(15) . . ?
O2 C9 C8 122.68(16) . . ?
O2 C9 C10 120.92(16) . . ?
C10 C9 C8 116.39(16) . . ?
C1 C10 C9 124.42(16) . . ?
C1 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 111.4(11) . . ?
C6 C12 H12B 108.7(10) . . ?
C6 C12 H12C 113.4(13) . . ?
H12A C12 H12B 107.9(14) . . ?
H12A C12 H12C 108.8(17) . . ?
H12B C12 H12C 106.4(16) . . ?
O3 C13 C8 119.23(18) . . ?
O3 C13 C14 119.05(18) . . ?
C14 C13 C8 121.72(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H4C O4 H4D 107(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
O1 C2 C3 C4 -73.1(2) . . . . ?
O2 C9 C10 C1 -175.93(19) . . . . ?
C1 C2 C3 C4 49.3(2) . . . . ?
C1 C6 C7 C8 3.6(2) . . . . ?
C2 C1 C6 C5 52.9(2) . . . . ?
C2 C1 C6 C7 174.11(15) . . . . ?
C2 C1 C6 C12 -68.6(2) . . . . ?
C2 C1 C10 C9 -177.31(17) . . . . ?
C2 C3 C4 C5 -55.5(3) . . . . ?
C3 C4 C5 C6 57.2(2) . . . . ?
C3 C4 C5 C11 -175.60(18) . . . . ?
C4 C5 C6 C1 -53.4(2) . . . . ?
C4 C5 C6 C7 -175.27(16) . . . . ?
C4 C5 C6 C12 68.6(2) . . . . ?
C5 C6 C7 C8 123.29(19) . . . . ?
C6 C1 C2 O1 69.4(2) . . . . ?
C6 C1 C2 C3 -51.0(2) . . . . ?
C6 C1 C10 C9 -1.4(3) . . . . ?
C6 C7 C8 C9 -1.8(3) . . . . ?
C6 C7 C8 C13 177.10(16) . . . . ?
C7 C8 C9 O2 177.57(18) . . . . ?
C7 C8 C9 C10 -1.7(2) . . . . ?
C7 C8 C13 O3 -17.0(3) . . . . ?
C7 C8 C13 C14 163.1(2) . . . . ?
C8 C9 C10 C1 3.3(3) . . . . ?
C9 C8 C13 O3 161.90(19) . . . . ?
C9 C8 C13 C14 -18.0(3) . . . . ?
C10 C1 C2 O1 -114.6(2) . . . . ?
C10 C1 C2 C3 125.0(2) . . . . ?
C10 C1 C6 C5 -123.04(18) . . . . ?
C10 C1 C6 C7 -1.9(2) . . . . ?
C10 C1 C6 C12 115.41(19) . . . . ?
C11 C5 C6 C1 -178.76(16) . . . . ?
C11 C5 C6 C7 59.4(2) . . . . ?
C11 C5 C6 C12 -56.8(2) . . . . ?
C12 C6 C7 C8 -117.27(19) . . . . ?
C13 C8 C9 O2 -1.3(3) . . . . ?
C13 C8 C9 C10 179.44(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
