# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_AX1020
_database_code_depnum_ccdc_archive 'CCDC 1532107'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H38 Ca I2 N2 O8'
_chemical_formula_weight         704.38

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_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                   7.4395(2)
_cell_length_b                   10.2984(3)
_cell_length_c                   10.4052(3)
_cell_angle_alpha                118.1251(6)
_cell_angle_beta                 94.6199(7)
_cell_angle_gamma                92.7499(7)
_cell_volume                     697.42(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      28.66

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             350
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.212
_exptl_absorpt_coefficient_mu    2.478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19016
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3203
_reflns_number_gt                3025
_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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0136P)²+0.3789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3203
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0173
_refine_ls_R_factor_gt           0.0158
_refine_ls_wR_factor_ref         0.0369
_refine_ls_wR_factor_gt          0.0361
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1513(2) 0.17471(18) -0.05245(18) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.1925(3) -0.0841(2) -0.1479(2) 0.0386(4) Uani 1 1 d . . . . .
H2A H 0.2078 -0.0551 -0.0431 0.058 Uiso 1 1 calc R U . . .
H2B H 0.3017 -0.1262 -0.1914 0.058 Uiso 1 1 calc R U . . .
H2C H 0.0878 -0.1581 -0.1968 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1442(3) 0.0242(2) -0.31513(19) 0.0382(4) Uani 1 1 d . . . . .
H3A H 0.1262 0.1186 -0.3133 0.057 Uiso 1 1 calc R U . . .
H3B H 0.0397 -0.0476 -0.3722 0.057 Uiso 1 1 calc R U . . .
H3C H 0.2542 -0.0131 -0.3604 0.057 Uiso 1 1 calc R U . . .
C4 C 0.3181(2) 0.7388(2) 0.31467(18) 0.0322(4) Uani 1 1 d . . . . .
H4A H 0.2535 0.8290 0.3476 0.039 Uiso 1 1 calc R U . . .
H4B H 0.4458 0.7682 0.3594 0.039 Uiso 1 1 calc R U . . .
C5 C 0.2309(2) 0.6352(2) 0.35828(18) 0.0320(4) Uani 1 1 d . . . . .
H5A H 0.2985 0.5469 0.3290 0.038 Uiso 1 1 calc R U . . .
H5B H 0.2289 0.6841 0.4659 0.038 Uiso 1 1 calc R U . . .
C6 C -0.0588(3) 0.5283(2) 0.34958(18) 0.0324(4) Uani 1 1 d . . . . .
H6A H -0.0554 0.5961 0.4561 0.039 Uiso 1 1 calc R U . . .
H6B H -0.0129 0.4346 0.3361 0.039 Uiso 1 1 calc R U . . .
C7 C -0.2470(2) 0.4996(2) 0.27643(19) 0.0338(4) Uani 1 1 d . . . . .
H7A H -0.3263 0.4493 0.3149 0.041 Uiso 1 1 calc R U . . .
H7B H -0.2957 0.5938 0.2945 0.041 Uiso 1 1 calc R U . . .
C8 C -0.4175(2) 0.3440(2) 0.0497(2) 0.0312(4) Uani 1 1 d . . . . .
H8A H -0.4960 0.4227 0.0606 0.037 Uiso 1 1 calc R U . . .
H8B H -0.4727 0.2853 0.0917 0.037 Uiso 1 1 calc R U . . .
C9 C -0.3981(2) 0.2474(2) -0.1076(2) 0.0332(4) Uani 1 1 d . . . . .
H9A H -0.3255 0.1653 -0.1191 0.040 Uiso 1 1 calc R U . . .
H9B H -0.5186 0.2048 -0.1647 0.040 Uiso 1 1 calc R U . . .
I1 I 0.33649(2) 0.19694(2) 0.33071(2) 0.03166(4) Uani 1 1 d . . . . .
Ca1 Ca 0.0000 0.5000 0.0000 0.01996(9) Uani 1 2 d S . P . .
N1 N 0.16298(18) 0.04571(15) -0.16622(15) 0.0254(3) Uani 1 1 d . . . . .
O1 O 0.12681(16) 0.28989(13) -0.05967(14) 0.0315(3) Uani 1 1 d . . . . .
O2 O 0.30880(15) 0.66245(12) 0.15841(12) 0.0256(2) Uani 1 1 d . . . . .
O3 O 0.05027(15) 0.59366(13) 0.28467(12) 0.0268(2) Uani 1 1 d . . . . .
O4 O -0.24017(15) 0.40741(13) 0.12292(12) 0.0271(2) Uani 1 1 d . . . . .
H1 H 0.166(2) 0.177(2) 0.040(2) 0.023(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2444(19) . ?
C1 N1 1.311(2) . ?
C1 H1 0.949(18) . ?
C2 N1 1.461(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N1 1.452(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O2 1.4277(19) . ?
C4 C5 1.484(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O3 1.430(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.425(2) . ?
C6 C7 1.485(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O4 1.429(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O4 1.426(2) . ?
C8 C9 1.485(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O2 1.429(2) 2_565 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
Ca1 O1 2.2318(11) 2_565 ?
Ca1 O1 2.2318(11) . ?
Ca1 O3 2.6339(11) 2_565 ?
Ca1 O3 2.6339(11) . ?
Ca1 O4 2.6631(11) . ?
Ca1 O4 2.6631(11) 2_565 ?
Ca1 O2 2.6860(11) 2_565 ?
Ca1 O2 2.6860(11) . ?
O2 C9 1.429(2) 2_565 ?

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 N1 124.39(15) . . ?
O1 C1 H1 120.3(11) . . ?
N1 C1 H1 115.3(11) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C5 106.85(14) . . ?
O2 C4 H4A 110.4 . . ?
C5 C4 H4A 110.4 . . ?
O2 C4 H4B 110.4 . . ?
C5 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
O3 C5 C4 106.81(13) . . ?
O3 C5 H5A 110.4 . . ?
C4 C5 H5A 110.4 . . ?
O3 C5 H5B 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
O3 C6 C7 107.71(13) . . ?
O3 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
O3 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
O4 C7 C6 107.03(14) . . ?
O4 C7 H7A 110.3 . . ?
C6 C7 H7A 110.3 . . ?
O4 C7 H7B 110.3 . . ?
C6 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
O4 C8 C9 107.05(13) . . ?
O4 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O4 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
O2 C9 C8 107.12(14) 2_565 . ?
O2 C9 H9A 110.3 2_565 . ?
C8 C9 H9A 110.3 . . ?
O2 C9 H9B 110.3 2_565 . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
O1 Ca1 O1 180.0 2_565 . ?
O1 Ca1 O3 94.69(4) 2_565 2_565 ?
O1 Ca1 O3 85.31(4) . 2_565 ?
O1 Ca1 O3 85.31(4) 2_565 . ?
O1 Ca1 O3 94.69(4) . . ?
O3 Ca1 O3 180.0 2_565 . ?
O1 Ca1 O4 92.70(4) 2_565 . ?
O1 Ca1 O4 87.30(4) . . ?
O3 Ca1 O4 119.35(3) 2_565 . ?
O3 Ca1 O4 60.65(3) . . ?
O1 Ca1 O4 87.30(4) 2_565 2_565 ?
O1 Ca1 O4 92.70(4) . 2_565 ?
O3 Ca1 O4 60.65(3) 2_565 2_565 ?
O3 Ca1 O4 119.35(3) . 2_565 ?
O4 Ca1 O4 180.0 . 2_565 ?
O1 Ca1 O2 91.46(4) 2_565 2_565 ?
O1 Ca1 O2 88.54(4) . 2_565 ?
O3 Ca1 O2 60.02(3) 2_565 2_565 ?
O3 Ca1 O2 119.98(3) . 2_565 ?
O4 Ca1 O2 59.69(3) . 2_565 ?
O4 Ca1 O2 120.31(3) 2_565 2_565 ?
O1 Ca1 O2 88.54(4) 2_565 . ?
O1 Ca1 O2 91.46(4) . . ?
O3 Ca1 O2 119.98(3) 2_565 . ?
O3 Ca1 O2 60.02(3) . . ?
O4 Ca1 O2 120.32(3) . . ?
O4 Ca1 O2 59.68(3) 2_565 . ?
O2 Ca1 O2 180.0 2_565 . ?
C1 N1 C3 122.13(14) . . ?
C1 N1 C2 120.83(15) . . ?
C3 N1 C2 117.03(15) . . ?
C1 O1 Ca1 154.07(11) . . ?
C4 O2 C9 110.40(13) . 2_565 ?
C4 O2 Ca1 118.98(9) . . ?
C9 O2 Ca1 117.25(9) 2_565 . ?
C6 O3 C5 110.61(12) . . ?
C6 O3 Ca1 120.47(9) . . ?
C5 O3 Ca1 118.96(9) . . ?
C8 O4 C7 110.44(13) . . ?
C8 O4 Ca1 121.18(9) . . ?
C7 O4 Ca1 116.33(10) . . ?

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
O2 C4 C5 O3 -57.65(17) . . . . ?
O3 C6 C7 O4 57.03(18) . . . . ?
O4 C8 C9 O2 -56.77(17) . . . 2_565 ?
O1 C1 N1 C3 -1.3(3) . . . . ?
O1 C1 N1 C2 179.83(15) . . . . ?
N1 C1 O1 Ca1 137.0(2) . . . . ?
C5 C4 O2 C9 -177.21(14) . . . 2_565 ?
C5 C4 O2 Ca1 42.93(16) . . . . ?
C7 C6 O3 C5 175.35(14) . . . . ?
C7 C6 O3 Ca1 -39.41(17) . . . . ?
C4 C5 O3 C6 -163.93(14) . . . . ?
C4 C5 O3 Ca1 50.24(16) . . . . ?
C9 C8 O4 C7 -178.58(14) . . . . ?
C9 C8 O4 Ca1 40.27(17) . . . . ?
C6 C7 O4 C8 165.21(14) . . . . ?
C6 C7 O4 Ca1 -51.57(16) . . . . ?

_refine_diff_density_max         0.694
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_AX1271_0m
_database_code_depnum_ccdc_archive 'CCDC 1542896'
_audit_update_record             
;
2017-04-07 deposited with the CCDC.
2017-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 O4'
_chemical_formula_weight         194.18

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'

_cell_length_a                   8.6487(2)
_cell_length_b                   9.6280(2)
_cell_length_c                   10.6343(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     885.51(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6114
_cell_measurement_theta_min      4.16
_cell_measurement_theta_max      69.70

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.203
_exptl_absorpt_coefficient_mu    0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microfocus
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            6385
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.200
_diffrn_reflns_theta_max         69.694
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1657
_reflns_number_gt                1651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.1239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1657
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.83477(18) 0.58016(17) 0.68327(16) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.93611(18) 0.70389(16) 0.84499(14) 0.0198(3) Uani 1 1 d . . . . .
H2 H 1.0303 0.7639 0.8497 0.024 Uiso 1 1 calc R U . . .
C3 C 0.98035(18) 0.55059(17) 0.85826(15) 0.0235(3) Uani 1 1 d . . . . .
H3A H 1.0919 0.5363 0.8419 0.028 Uiso 1 1 calc R U . . .
H3B H 0.9550 0.5151 0.9432 0.028 Uiso 1 1 calc R U . . .
C4 C 0.81346(19) 0.75437(16) 0.93834(15) 0.0214(4) Uani 1 1 d . . . . .
H4B H 0.8574 0.7492 1.0252 0.026 Uiso 1 1 calc R U . . .
C5 C 0.76612(19) 0.90304(17) 0.91206(15) 0.0213(3) Uani 1 1 d . . . . .
C6 C 0.6450(2) 0.93392(18) 0.83074(16) 0.0254(4) Uani 1 1 d . . . . .
H6 H 0.5894 0.8609 0.7912 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6049(2) 1.0717(2) 0.80709(17) 0.0290(4) Uani 1 1 d . . . . .
H7 H 0.5218 1.0924 0.7517 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6863(2) 1.17869(19) 0.86441(19) 0.0317(4) Uani 1 1 d . . . . .
H8 H 0.6590 1.2726 0.8483 0.038 Uiso 1 1 calc R U . . .
C9 C 0.8073(2) 1.14835(19) 0.94512(18) 0.0309(4) Uani 1 1 d . . . . .
H9 H 0.8633 1.2214 0.9842 0.037 Uiso 1 1 calc R U . . .
C10 C 0.8465(2) 1.01095(18) 0.96891(16) 0.0253(4) Uani 1 1 d . . . . .
H10 H 0.9293 0.9906 1.0247 0.030 Uiso 1 1 calc R U . . .
O1 O 0.87009(13) 0.70837(11) 0.71918(10) 0.0221(3) Uani 1 1 d . . . . .
O2 O 0.88625(14) 0.48370(11) 0.76259(12) 0.0256(3) Uani 1 1 d . . . . .
O3 O 0.76432(16) 0.55392(14) 0.58815(12) 0.0334(3) Uani 1 1 d . . . . .
O4 O 0.68076(14) 0.66710(13) 0.93211(12) 0.0269(3) Uani 1 1 d . . . . .
H4A H 0.698(3) 0.594(3) 0.983(3) 0.047(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.208(2) . ?
C1 O1 1.328(2) . ?
C1 O2 1.331(2) . ?
C2 O1 1.4553(18) . ?
C2 C3 1.531(2) . ?
C2 C4 1.532(2) . ?
C2 H2 1.0000 . ?
C3 O2 1.453(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O4 1.424(2) . ?
C4 C5 1.515(2) . ?
C4 H4B 1.0000 . ?
C5 C10 1.389(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
O4 H4A 0.90(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
O3 C1 O1 123.47(16) . . ?
O3 C1 O2 123.61(16) . . ?
O1 C1 O2 112.92(14) . . ?
O1 C2 C3 102.20(12) . . ?
O1 C2 C4 108.34(12) . . ?
C3 C2 C4 114.78(13) . . ?
O1 C2 H2 110.4 . . ?
C3 C2 H2 110.4 . . ?
C4 C2 H2 110.4 . . ?
O2 C3 C2 102.87(12) . . ?
O2 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
O2 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
O4 C4 C5 109.34(13) . . ?
O4 C4 C2 109.92(13) . . ?
C5 C4 C2 111.55(13) . . ?
O4 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C2 C4 H4B 108.7 . . ?
C10 C5 C6 119.21(16) . . ?
C10 C5 C4 119.42(15) . . ?
C6 C5 C4 121.36(15) . . ?
C5 C6 C7 120.21(17) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.03(17) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.92(17) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.90(17) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.72(17) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C1 O1 C2 109.09(12) . . ?
C1 O2 C3 108.77(13) . . ?
C4 O4 H4A 107.2(18) . . ?

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 O2 -19.68(14) . . . . ?
C4 C2 C3 O2 97.35(15) . . . . ?
O1 C2 C4 O4 59.81(16) . . . . ?
C3 C2 C4 O4 -53.66(18) . . . . ?
O1 C2 C4 C5 -61.64(16) . . . . ?
C3 C2 C4 C5 -175.11(13) . . . . ?
O4 C4 C5 C10 148.76(15) . . . . ?
C2 C4 C5 C10 -89.45(18) . . . . ?
O4 C4 C5 C6 -32.1(2) . . . . ?
C2 C4 C5 C6 89.66(18) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C7 -179.29(16) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C6 C5 C10 C9 -0.1(3) . . . . ?
C4 C5 C10 C9 179.03(16) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
O3 C1 O1 C2 172.45(15) . . . . ?
O2 C1 O1 C2 -8.07(17) . . . . ?
C3 C2 O1 C1 17.42(15) . . . . ?
C4 C2 O1 C1 -104.14(14) . . . . ?
O3 C1 O2 C3 173.55(15) . . . . ?
O1 C1 O2 C3 -5.93(18) . . . . ?
C2 C3 O2 C1 16.28(16) . . . . ?

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
O4 H4A O3 0.90(3) 1.84(3) 2.7399(18) 180(3) 4_665

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.056

