# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_P212121_a
_database_code_depnum_ccdc_archive 'CCDC 1835801'

_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_publcif_datablock.id            {5f8c759e-5ca4-48a4-aaf5-671621297cc5}

#============================================================================== 
# FM0678P
#==============================================================================
_audit_creation_date             2016-12-16
_audit_creation_method           SHELXL-2014

#==============================================================================

#  CHEMICAL DATA

#==============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 N O5'
_chemical_formula_sum            'C21 H23 N O5'
_chemical_formula_weight         369.40
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration unk

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'
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'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1336(5)
_cell_length_b                   12.7135(8)
_cell_length_c                   20.4017(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1850.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block

_exptl_crystal_colour            colurless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            9161
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3284
_reflns_number_gt                3080
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;

_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)+(0.0471P)²+0.3742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1200 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_number_reflns         3284
_refine_ls_number_parameters     247
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.165
_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 0.8614(3) 0.94407(18) 0.15686(11) 0.0180(4) Uani 1 1 d . U . . .
C2 C 0.8293(4) 1.02039(18) 0.21190(11) 0.0184(4) Uani 1 1 d . U . . .
H2A H 0.9461 1.0275 0.2378 0.022 Uiso 1 1 calc R U . . .
H2B H 0.7987 1.0903 0.1934 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6737(3) 0.98600(18) 0.25616(11) 0.0177(4) Uani 1 1 d . U . . .
H3 H 0.6413 1.0317 0.2912 0.021 Uiso 1 1 calc R U . . .
C4 C 0.5771(3) 0.89716(17) 0.25074(11) 0.0175(4) Uani 1 1 d . U . . .
C5 C 0.4054(4) 0.88360(18) 0.29307(11) 0.0194(4) Uani 1 1 d . U . . .
H5 H 0.3825 0.9503 0.3178 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2336(3) 0.85839(18) 0.25228(12) 0.0207(4) Uani 1 1 d . U . . .
H6A H 0.1947 0.9222 0.2280 0.025 Uiso 1 1 calc R U . . .
H6B H 0.1294 0.8381 0.2818 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2692(4) 0.76982(18) 0.20382(12) 0.0199(4) Uani 1 1 d . U . . .
H7A H 0.1550 0.7581 0.1773 0.024 Uiso 1 1 calc R U . . .
H7B H 0.2960 0.7042 0.2282 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4340(3) 0.79432(18) 0.15816(11) 0.0188(4) Uani 1 1 d . U . . .
H8 H 0.4033 0.8621 0.1357 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6186(3) 0.81414(17) 0.19851(11) 0.0177(4) Uani 1 1 d . U . . .
C10 C 0.7681(3) 0.85377(17) 0.15205(11) 0.0174(4) Uani 1 1 d . U . . .
H10 H 0.7983 0.8099 0.1159 0.021 Uiso 1 1 calc R U . . .
C11 C 1.0058(4) 0.97553(18) 0.10780(11) 0.0194(4) Uani 1 1 d . U . . .
C12 C 1.0296(4) 0.9124(2) 0.04591(12) 0.0241(5) Uani 1 1 d . U . . .
H12A H 1.1238 0.9460 0.0179 0.036 Uiso 1 1 calc R U . . .
H12B H 0.9098 0.9091 0.0225 0.036 Uiso 1 1 calc R U . . .
H12C H 1.0706 0.8410 0.0570 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4244(4) 0.82221(19) 0.40404(11) 0.0201(4) Uani 1 1 d . U . . .
C14 C 0.4388(3) 0.72781(18) 0.44765(11) 0.0195(4) Uani 1 1 d . U . . .
C15 C 0.4178(4) 0.7429(2) 0.51506(11) 0.0213(4) Uani 1 1 d . U . . .
H15 H 0.3921 0.8112 0.5317 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4342(3) 0.65894(19) 0.55774(12) 0.0216(4) Uani 1 1 d . U . . .
H16 H 0.4200 0.6686 0.6037 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4717(4) 0.56055(19) 0.53191(11) 0.0207(4) Uani 1 1 d . U . . .
C18 C 0.4906(4) 0.54324(19) 0.46527(11) 0.0202(4) Uani 1 1 d . U . . .
H18 H 0.5141 0.4745 0.4489 0.024 Uiso 1 1 calc R U . . .
C19 C 0.4747(3) 0.62737(18) 0.42305(12) 0.0194(4) Uani 1 1 d . U . . .
H19 H 0.4883 0.6170 0.3772 0.023 Uiso 1 1 calc R U . . .
C20 C 0.4532(4) 0.71125(18) 0.10435(12) 0.0230(5) Uani 1 1 d . U . . .
H20A H 0.4875 0.6436 0.1241 0.035 Uiso 1 1 calc R U . . .
H20B H 0.5509 0.7328 0.0734 0.035 Uiso 1 1 calc R U . . .
H20C H 0.3336 0.7040 0.0811 0.035 Uiso 1 1 calc R U . . .
C21 C 0.6938(3) 0.71218(18) 0.23030(12) 0.0187(5) Uani 1 1 d . U . . .
H21A H 0.7398 0.6647 0.1960 0.028 Uiso 1 1 calc R U . . .
H21B H 0.5927 0.6777 0.2547 0.028 Uiso 1 1 calc R U . . .
H21C H 0.7966 0.7295 0.2603 0.028 Uiso 1 1 calc R U . . .
N1 N 0.4979(3) 0.47079(16) 0.57692(10) 0.0237(4) Uani 1 1 d . U . . .
O1 O 1.1023(3) 1.05345(13) 0.11806(8) 0.0267(4) Uani 1 1 d . U . . .
O2 O 0.4310(2) 0.79660(12) 0.34047(8) 0.0205(3) Uani 1 1 d . U . . .
O3 O 0.4069(3) 0.91033(13) 0.42453(9) 0.0365(5) Uani 1 1 d . U . . .
O4 O 0.4979(3) 0.48801(15) 0.63596(8) 0.0331(5) Uani 1 1 d . U . . .
O5 O 0.5202(3) 0.38284(13) 0.55295(9) 0.0328(5) Uani 1 1 d . 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
C1 C10 1.331(3) . ?
C1 C11 1.491(3) . ?
C1 C2 1.502(3) . ?
C2 C3 1.496(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.328(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.509(3) . ?
C4 C9 1.529(3) . ?
C5 O2 1.481(3) . ?
C5 C6 1.516(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.520(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.532(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C20 1.530(3) . ?
C8 C9 1.573(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.513(3) . ?
C9 C21 1.546(3) . ?
C10 H10 0.9500 . ?
C11 O1 1.224(3) . ?
C11 C12 1.505(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O3 1.202(3) . ?
C13 O2 1.338(3) . ?
C13 C14 1.498(3) . ?
C14 C19 1.396(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(3) . ?
C17 N1 1.477(3) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 O4 1.224(3) . ?
N1 O5 1.231(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
C10 C1 C11 121.8(2) . . ?
C10 C1 C2 122.4(2) . . ?
C11 C1 C2 115.7(2) . . ?
C3 C2 C1 112.1(2) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 125.7(2) . . ?
C4 C3 H3 117.2 . . ?
C2 C3 H3 117.2 . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C9 123.0(2) . . ?
C5 C4 C9 118.5(2) . . ?
O2 C5 C4 111.03(19) . . ?
O2 C5 C6 107.49(18) . . ?
C4 C5 C6 111.49(19) . . ?
O2 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C5 C6 C7 112.2(2) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 111.9(2) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C20 C8 C7 111.4(2) . . ?
C20 C8 C9 114.29(19) . . ?
C7 C8 C9 110.89(18) . . ?
C20 C8 H8 106.6 . . ?
C7 C8 H8 106.6 . . ?
C9 C8 H8 106.6 . . ?
C10 C9 C4 110.07(19) . . ?
C10 C9 C21 107.29(19) . . ?
C4 C9 C21 110.72(18) . . ?
C10 C9 C8 108.39(18) . . ?
C4 C9 C8 108.26(19) . . ?
C21 C9 C8 112.08(19) . . ?
C1 C10 C9 126.4(2) . . ?
C1 C10 H10 116.8 . . ?
C9 C10 H10 116.8 . . ?
O1 C11 C1 119.4(2) . . ?
O1 C11 C12 120.8(2) . . ?
C1 C11 C12 119.9(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O2 124.6(2) . . ?
O3 C13 C14 123.2(2) . . ?
O2 C13 C14 112.24(19) . . ?
C19 C14 C15 120.0(2) . . ?
C19 C14 C13 122.1(2) . . ?
C15 C14 C13 117.9(2) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 118.3(2) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C16 122.5(2) . . ?
C18 C17 N1 118.4(2) . . ?
C16 C17 N1 119.1(2) . . ?
C19 C18 C17 118.9(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21A 109.5 . . ?
C9 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C9 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 N1 O5 123.6(2) . . ?
O4 N1 C17 118.3(2) . . ?
O5 N1 C17 118.13(19) . . ?
C13 O2 C5 116.54(17) . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

####################################################################### 
# 
# 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_P21m_a
_database_code_depnum_ccdc_archive 'CCDC 1835813'
_audit_update_record             
;
2018-04-09 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
#============================================================================== 
# FM0903p
#==============================================================================
_audit_creation_date             2017-09-04
_audit_creation_method           SHELXL-2014

#==============================================================================

#  CHEMICAL DATA

#==============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O5'
_chemical_formula_sum            'C16 H20 O5'
_chemical_formula_weight         292.32
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration unk

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'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.5141(19)
_cell_length_b                   7.7265(17)
_cell_length_c                   22.836(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.095(3)
_cell_angle_gamma                90
_cell_volume                     1498.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3150
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block

_exptl_crystal_colour            colurless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================

#   EXPERIMENTAL DATA

#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            6880
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.788
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4520
_reflns_number_gt                4113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.583
_reflns_Friedel_fraction_max     0.684
_reflns_Friedel_fraction_full    0.686

_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 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;

_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)+(0.0480P)²+0.3624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(6)
_refine_ls_number_reflns         4520
_refine_ls_number_parameters     425
_refine_ls_number_restraints     367
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.056
_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 0.0948(3) 0.6114(4) 0.48195(12) 0.0184(6) Uani 1 1 d . U . . .
C2 C -0.0071(3) 0.5949(5) 0.53029(12) 0.0210(6) Uani 1 1 d . U . . .
H2 H -0.1165 0.5792 0.5204 0.025 Uiso 1 1 calc R U . . .
C3 C 0.0400(3) 0.5999(4) 0.58724(12) 0.0184(6) Uani 1 1 d . U . . .
C4 C -0.0812(3) 0.5650(5) 0.63144(13) 0.0231(7) Uani 1 1 d . U . . .
H4 H -0.1828 0.5280 0.6105 0.028 Uiso 1 1 calc R U . . .
C5 C -0.0246(4) 0.4278(5) 0.67486(13) 0.0277(7) Uani 1 1 d . U . . .
H5A H -0.0222 0.3147 0.6546 0.033 Uiso 1 1 calc R U . . .
H5B H -0.0996 0.4185 0.7059 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1382(4) 0.4678(5) 0.70293(13) 0.0282(7) Uani 1 1 d . U . . .
H6A H 0.1715 0.3737 0.7305 0.034 Uiso 1 1 calc R U . . .
H6B H 0.1342 0.5766 0.7257 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2581(3) 0.4864(5) 0.65701(13) 0.0242(7) Uani 1 1 d . U . . .
H7 H 0.2590 0.3740 0.6353 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2103(3) 0.6295(5) 0.61073(12) 0.0192(6) Uani 1 1 d . U . . .
C9 C 0.3211(3) 0.6138(4) 0.56240(12) 0.0186(6) Uani 1 1 d . U . . .
H9 H 0.4285 0.6629 0.5721 0.022 Uiso 1 1 calc R U . . .
C10 C 0.2696(3) 0.6130(4) 0.49883(12) 0.0174(6) Uani 1 1 d . U . . .
C11 C -0.2260(3) 0.8259(5) 0.64575(13) 0.0245(7) Uani 1 1 d . U . . .
C12 C -0.2391(4) 0.9805(5) 0.68406(14) 0.0333(8) Uani 1 1 d . U . . .
H12A H -0.1763 1.0753 0.6694 0.050 Uiso 1 1 calc R U . . .
H12B H -0.2001 0.9517 0.7243 0.050 Uiso 1 1 calc R U . . .
H12C H -0.3496 1.0163 0.6837 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4240(4) 0.5123(6) 0.68612(14) 0.0342(8) Uani 1 1 d . U . . .
H13A H 0.4276 0.6201 0.7087 0.051 Uiso 1 1 calc R U . . .
H13B H 0.4998 0.5184 0.6558 0.051 Uiso 1 1 calc R U . . .
H13C H 0.4509 0.4148 0.7124 0.051 Uiso 1 1 calc R U . . .
C14 C 0.2286(3) 0.8144(4) 0.63619(13) 0.0208(7) Uani 1 1 d . U . . .
H14A H 0.3406 0.8403 0.6447 0.031 Uiso 1 1 calc R U . . .
H14B H 0.1740 0.8223 0.6724 0.031 Uiso 1 1 calc R U . . .
H14C H 0.1828 0.8980 0.6075 0.031 Uiso 1 1 calc R U . . .
C15 C 0.3810(3) 0.6826(5) 0.45606(12) 0.0192(6) Uani 1 1 d . U . . .
C16 C 0.5391(3) 0.5975(5) 0.45646(14) 0.0248(7) Uani 1 1 d . U . . .
H16A H 0.6023 0.6549 0.4280 0.037 Uiso 1 1 calc R U . . .
H16B H 0.5257 0.4751 0.4459 0.037 Uiso 1 1 calc R U . . .
H16C H 0.5927 0.6067 0.4958 0.037 Uiso 1 1 calc R U . . .
C1B C 0.4127(3) 0.2007(5) 1.02176(12) 0.0207(6) Uani 1 1 d . U . . .
C2B C 0.5201(3) 0.1980(5) 0.97494(12) 0.0221(7) Uani 1 1 d . U . . .
H2B H 0.6298 0.1988 0.9859 0.026 Uiso 1 1 calc R U . . .
C3B C 0.4758(3) 0.1945(5) 0.91778(13) 0.0230(7) Uani 1 1 d . U . . .
C4B C 0.6036(4) 0.1818(6) 0.87508(13) 0.0321(8) Uani 1 1 d . U . . .
H4B H 0.7067 0.1605 0.8977 0.039 Uiso 1 1 calc R U . A 1
C5B C 0.5720(4) 0.0361(6) 0.83218(15) 0.0408(9) Uani 1 1 d . U . . .
H5B1 H 0.5874 -0.0756 0.8530 0.049 Uiso 1 1 calc R U . . .
H5B2 H 0.6486 0.0420 0.8016 0.049 Uiso 1 1 calc R U . . .
C6B C 0.4057(4) 0.0428(5) 0.80290(14) 0.0366(8) Uani 1 1 d . U . . .
H6B1 H 0.3888 -0.0580 0.7764 0.044 Uiso 1 1 calc R U . . .
H6B2 H 0.3932 0.1492 0.7788 0.044 Uiso 1 1 calc R U . . .
C7B C 0.2815(4) 0.0413(5) 0.84855(13) 0.0292(7) Uani 1 1 d . U . . .
H7B H 0.2987 -0.0671 0.8720 0.035 Uiso 1 1 calc R U . . .
C8B C 0.3059(3) 0.1959(5) 0.89250(12) 0.0212(6) Uani 1 1 d . U . . .
C9B C 0.1916(3) 0.1735(4) 0.93974(12) 0.0193(6) Uani 1 1 d . U . . .
H9B H 0.0816 0.2121 0.9283 0.023 Uiso 1 1 calc R U . . .
C10B C 0.2392(3) 0.1875(5) 1.00341(12) 0.0184(6) Uani 1 1 d . U . . .
C13B C 0.1157(4) 0.0306(6) 0.81891(14) 0.0381(9) Uani 1 1 d . U . . .
H13D H 0.0945 0.1339 0.7947 0.057 Uiso 1 1 calc R U . . .
H13E H 0.0392 0.0237 0.8489 0.057 Uiso 1 1 calc R U . . .
H13F H 0.1067 -0.0728 0.7940 0.057 Uiso 1 1 calc R U . . .
C14B C 0.2686(3) 0.3722(5) 0.86374(13) 0.0215(7) Uani 1 1 d . U . . .
H14D H 0.1559 0.3786 0.8517 0.032 Uiso 1 1 calc R U . . .
H14E H 0.3296 0.3858 0.8292 0.032 Uiso 1 1 calc R U . . .
H14F H 0.2964 0.4648 0.8919 0.032 Uiso 1 1 calc R U . . .
C15B C 0.1223(3) 0.2606(5) 1.04315(12) 0.0222(7) Uani 1 1 d . U . . .
C16B C -0.0281(4) 0.1643(5) 1.04707(15) 0.0329(8) Uani 1 1 d . U . . .
H16D H -0.0998 0.2326 1.0696 0.049 Uiso 1 1 calc R U . . .
H16E H -0.0068 0.0531 1.0667 0.049 Uiso 1 1 calc R U . . .
H16F H -0.0768 0.1440 1.0075 0.049 Uiso 1 1 calc R U . . .
O1 O 0.0439(2) 0.6137(4) 0.43090(8) 0.0238(5) Uani 1 1 d . U . . .
O2 O -0.1059(2) 0.7230(4) 0.66545(8) 0.0236(5) Uani 1 1 d . U . . .
O3 O -0.3100(3) 0.7953(4) 0.60239(10) 0.0378(6) Uani 1 1 d . U . . .
O4 O 0.3185(2) 0.4567(3) 0.52932(8) 0.0202(5) Uani 1 1 d . U . . .
O5 O 0.3411(2) 0.8035(4) 0.42488(9) 0.0273(5) Uani 1 1 d . U . . .
O1B O 0.4581(2) 0.2052(4) 1.07337(8) 0.0298(6) Uani 1 1 d . U . . .
O4B O 0.2032(2) 0.0222(4) 0.97604(8) 0.0233(5) Uani 1 1 d . U . . .
O5B O 0.1538(2) 0.3936(4) 1.06920(9) 0.0300(5) Uani 1 1 d . U . . .
O2B O 0.6083(6) 0.3604(10) 0.8460(4) 0.0249(14) Uani 0.583(12) 1 d D U P B 1
C11B C 0.7489(7) 0.4297(12) 0.8364(4) 0.0299(15) Uani 0.583(12) 1 d D U P B 1
O3B O 0.8709(5) 0.3540(8) 0.8508(4) 0.049(2) Uani 0.583(12) 1 d D U P B 1
C12B C 0.7337(14) 0.5995(16) 0.8066(7) 0.033(2) Uani 0.583(12) 1 d D U P B 1
H12D H 0.8195 0.6756 0.8216 0.050 Uiso 0.583(12) 1 calc R U P B 1
H12E H 0.6324 0.6518 0.8143 0.050 Uiso 0.583(12) 1 calc R U P B 1
H12F H 0.7392 0.5835 0.7643 0.050 Uiso 0.583(12) 1 calc R U P B 1
O2C O 0.6094(9) 0.3185(15) 0.8377(6) 0.0302(17) Uani 0.417(12) 1 d D U P B 2
C11C C 0.7389(10) 0.4159(16) 0.8488(6) 0.0303(18) Uani 0.417(12) 1 d D U P B 2
O3C O 0.8379(10) 0.3776(12) 0.8876(5) 0.057(3) Uani 0.417(12) 1 d D U P B 2
C12C C 0.7381(18) 0.572(2) 0.8115(10) 0.029(3) Uani 0.417(12) 1 d D U P B 2
H12X H 0.6985 0.6710 0.8330 0.043 Uiso 0.417(12) 1 calc R U P B 2
H12Y H 0.6698 0.5529 0.7757 0.043 Uiso 0.417(12) 1 calc R U P B 2
H12Z H 0.8454 0.5969 0.8009 0.043 Uiso 0.417(12) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.215(3) . ?
C1 C2 1.457(4) . ?
C1 C10 1.511(4) . ?
C2 C3 1.334(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.518(4) . ?
C3 C8 1.527(4) . ?
C4 O2 1.470(4) . ?
C4 C5 1.507(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.516(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.522(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C13 1.531(4) . ?
C7 C8 1.563(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.507(4) . ?
C8 C14 1.547(4) . ?
C9 O4 1.428(4) . ?
C9 C10 1.486(4) . ?
C9 H9 1.0000 . ?
C10 O4 1.441(3) . ?
C10 C15 1.508(4) . ?
C11 O3 1.203(4) . ?
C11 O2 1.347(4) . ?
C11 C12 1.490(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O5 1.209(4) . ?
C15 C16 1.497(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C1B O1B 1.214(3) . ?
C1B C2B 1.456(4) . ?
C1B C10B 1.510(4) . ?
C2B C3B 1.333(4) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.515(4) . ?
C3B C8B 1.518(4) . ?
C4B O2C 1.361(15) . ?
C4B C5B 1.504(5) . ?
C4B O2B 1.532(9) . ?
C4B H4B 1.0000 . ?
C5B C6B 1.523(5) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B C7B 1.537(4) . ?
C6B H6B1 0.9900 . ?
C6B H6B2 0.9900 . ?
C7B C13B 1.524(5) . ?
C7B C8B 1.564(4) . ?
C7B H7B 1.0000 . ?
C8B C9B 1.513(4) . ?
C8B C14B 1.536(4) . ?
C9B O4B 1.432(4) . ?
C9B C10B 1.485(4) . ?
C9B H9B 1.0000 . ?
C10B O4B 1.445(4) . ?
C10B C15B 1.504(4) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B O5B 1.208(4) . ?
C15B C16B 1.489(4) . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
O2B C11B 1.344(6) . ?
C11B O3B 1.216(6) . ?
C11B C12B 1.479(7) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
O2C C11C 1.344(6) . ?
C11C O3C 1.216(6) . ?
C11C C12C 1.479(7) . ?
C12C H12X 0.9800 . ?
C12C H12Y 0.9800 . ?
C12C H12Z 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
O1 C1 C2 122.5(3) . . ?
O1 C1 C10 121.5(2) . . ?
C2 C1 C10 115.9(2) . . ?
C3 C2 C1 125.6(3) . . ?
C3 C2 H2 117.2 . . ?
C1 C2 H2 117.2 . . ?
C2 C3 C4 118.2(2) . . ?
C2 C3 C8 124.0(3) . . ?
C4 C3 C8 117.8(2) . . ?
O2 C4 C5 106.7(2) . . ?
O2 C4 C3 109.5(2) . . ?
C5 C4 C3 111.2(3) . . ?
O2 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C4 C5 C6 112.0(3) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 111.4(2) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C13 110.9(3) . . ?
C6 C7 C8 112.2(2) . . ?
C13 C7 C8 112.9(3) . . ?
C6 C7 H7 106.8 . . ?
C13 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
C9 C8 C3 111.1(2) . . ?
C9 C8 C14 107.3(2) . . ?
C3 C8 C14 109.8(2) . . ?
C9 C8 C7 107.0(2) . . ?
C3 C8 C7 109.1(2) . . ?
C14 C8 C7 112.6(2) . . ?
O4 C9 C10 59.20(17) . . ?
O4 C9 C8 117.9(2) . . ?
C10 C9 C8 124.0(2) . . ?
O4 C9 H9 114.7 . . ?
C10 C9 H9 114.7 . . ?
C8 C9 H9 114.7 . . ?
O4 C10 C9 58.40(17) . . ?
O4 C10 C15 116.0(2) . . ?
C9 C10 C15 118.4(2) . . ?
O4 C10 C1 111.2(2) . . ?
C9 C10 C1 117.8(2) . . ?
C15 C10 C1 119.4(2) . . ?
O3 C11 O2 123.5(3) . . ?
O3 C11 C12 125.2(3) . . ?
O2 C11 C12 111.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 C16 123.9(3) . . ?
O5 C15 C10 119.5(3) . . ?
C16 C15 C10 116.5(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1B C1B C2B 122.7(3) . . ?
O1B C1B C10B 120.6(3) . . ?
C2B C1B C10B 116.6(2) . . ?
C3B C2B C1B 124.8(3) . . ?
C3B C2B H2B 117.6 . . ?
C1B C2B H2B 117.6 . . ?
C2B C3B C4B 117.7(3) . . ?
C2B C3B C8B 124.6(3) . . ?
C4B C3B C8B 117.7(2) . . ?
O2C C4B C5B 100.6(6) . . ?
O2C C4B C3B 114.4(6) . . ?
C5B C4B C3B 111.4(3) . . ?
C5B C4B O2B 113.6(4) . . ?
C3B C4B O2B 105.2(4) . . ?
C5B C4B H4B 108.8 . . ?
C3B C4B H4B 108.8 . . ?
O2B C4B H4B 108.8 . . ?
C4B C5B C6B 112.2(3) . . ?
C4B C5B H5B1 109.2 . . ?
C6B C5B H5B1 109.2 . . ?
C4B C5B H5B2 109.2 . . ?
C6B C5B H5B2 109.2 . . ?
H5B1 C5B H5B2 107.9 . . ?
C5B C6B C7B 111.4(3) . . ?
C5B C6B H6B1 109.3 . . ?
C7B C6B H6B1 109.3 . . ?
C5B C6B H6B2 109.3 . . ?
C7B C6B H6B2 109.3 . . ?
H6B1 C6B H6B2 108.0 . . ?
C13B C7B C6B 111.1(3) . . ?
C13B C7B C8B 113.8(3) . . ?
C6B C7B C8B 111.3(3) . . ?
C13B C7B H7B 106.8 . . ?
C6B C7B H7B 106.8 . . ?
C8B C7B H7B 106.8 . . ?
C9B C8B C3B 111.8(2) . . ?
C9B C8B C14B 106.4(2) . . ?
C3B C8B C14B 109.3(3) . . ?
C9B C8B C7B 107.9(3) . . ?
C3B C8B C7B 108.6(3) . . ?
C14B C8B C7B 112.9(2) . . ?
O4B C9B C10B 59.34(18) . . ?
O4B C9B C8B 119.0(2) . . ?
C10B C9B C8B 123.0(2) . . ?
O4B C9B H9B 114.7 . . ?
C10B C9B H9B 114.7 . . ?
C8B C9B H9B 114.7 . . ?
O4B C10B C9B 58.51(18) . . ?
O4B C10B C15B 117.6(2) . . ?
C9B C10B C15B 118.2(2) . . ?
O4B C10B C1B 110.7(2) . . ?
C9B C10B C1B 118.0(2) . . ?
C15B C10B C1B 118.9(2) . . ?
C7B C13B H13D 109.5 . . ?
C7B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C7B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C8B C14B H14D 109.5 . . ?
C8B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C8B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
O5B C15B C16B 123.8(3) . . ?
O5B C15B C10B 118.9(3) . . ?
C16B C15B C10B 117.2(3) . . ?
C15B C16B H16D 109.5 . . ?
C15B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C11 O2 C4 116.6(2) . . ?
C9 O4 C10 62.40(18) . . ?
C9B O4B C10B 62.15(19) . . ?
C11B O2B C4B 118.7(4) . . ?
O3B C11B O2B 121.2(5) . . ?
O3B C11B C12B 126.5(5) . . ?
O2B C11B C12B 112.3(5) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11C O2C C4B 112.5(7) . . ?
O3C C11C O2C 121.2(5) . . ?
O3C C11C C12C 126.4(5) . . ?
O2C C11C C12C 112.3(5) . . ?
C11C C12C H12X 109.5 . . ?
C11C C12C H12Y 109.5 . . ?
H12X C12C H12Y 109.5 . . ?
C11C C12C H12Z 109.5 . . ?
H12X C12C H12Z 109.5 . . ?
H12Y C12C H12Z 109.5 . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_P212121
_database_code_depnum_ccdc_archive 'CCDC 1843993'

_audit_update_record             
;
2018-05-18 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_publcif_datablock.id            {d24d5b96-a77d-4a78-ae34-6dfa93d7c9b9}
#============================================================================== 
# FM093p
#==============================================================================
_audit_creation_date             2017-09-26
_audit_creation_method           SHELXL-2014

#==============================================================================

#  CHEMICAL DATA

#==============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 O4'
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration unk

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'

#==============================================================================

#   CRYSTAL DATA

#==============================================================================


_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.102(3)
_cell_length_b                   8.451(3)
_cell_length_c                   24.298(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1458.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3927
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.277
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            7111
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2568
_reflns_number_gt                2460
_reflns_threshold_expression     'I > 2σ'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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 AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0432P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 978 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)

_refine_ls_number_reflns         2568
_refine_ls_number_parameters     185
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.212
_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 0.8117(3) 0.7410(2) 0.41553(8) 0.0161(4) Uani 1 1 d . U . . .
C2 C 0.6543(3) 0.6453(2) 0.43610(8) 0.0160(4) Uani 1 1 d . U . . .
H2 H 0.616875 0.658017 0.473383 0.019 Uiso 1 1 calc R U . . .
C3 C 0.5604(3) 0.5407(2) 0.40484(8) 0.0151(3) Uani 1 1 d . U . . .
C4 C 0.3927(3) 0.4544(2) 0.42874(9) 0.0176(4) Uani 1 1 d . U . . .
H4 H 0.368755 0.491125 0.467239 0.021 Uiso 1 1 calc R U . . .
C5 C 0.2191(3) 0.4836(3) 0.39306(9) 0.0196(4) Uani 1 1 d . U . . .
H5A H 0.113238 0.418441 0.406807 0.024 Uiso 1 1 calc R U . . .
H5B H 0.181977 0.596184 0.395790 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2578(3) 0.4422(3) 0.33298(9) 0.0187(4) Uani 1 1 d . U . . .
H6A H 0.143773 0.464902 0.310925 0.022 Uiso 1 1 calc R U . . .
H6B H 0.284147 0.327473 0.330088 0.022 Uiso 1 1 calc R U . . .
C7 C 0.4250(3) 0.5350(3) 0.30884(8) 0.0167(4) Uani 1 1 d . U . . .
H7 H 0.390890 0.649706 0.310187 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6091(3) 0.5133(2) 0.34462(8) 0.0149(3) Uani 1 1 d . U . . .
C9 C 0.7547(3) 0.6281(2) 0.32472(8) 0.0150(4) Uani 1 1 d . U . . .
H9 H 0.784803 0.624888 0.286634 0.018 Uiso 1 1 calc R U . . .
C10 C 0.8468(3) 0.7350(2) 0.35541(8) 0.0158(3) Uani 1 1 d . U . . .
C11 C 0.4441(3) 0.2071(3) 0.47654(9) 0.0213(4) Uani 1 1 d . U . . .
C12 C 0.4848(3) 0.0356(3) 0.46657(10) 0.0261(5) Uani 1 1 d . U . . .
H12A H 0.480691 -0.021846 0.501580 0.039 Uiso 1 1 calc R U . . .
H12B H 0.610187 0.024588 0.450156 0.039 Uiso 1 1 calc R U . . .
H12C H 0.390250 -0.008115 0.441444 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4514(3) 0.4914(3) 0.24821(9) 0.0207(5) Uani 1 1 d . U . . .
H13A H 0.558552 0.550200 0.233124 0.031 Uiso 1 1 calc R U . . .
H13B H 0.337172 0.518601 0.227640 0.031 Uiso 1 1 calc R U . . .
H13C H 0.475309 0.377593 0.245026 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6966(3) 0.3451(2) 0.33711(8) 0.0175(4) Uani 1 1 d . U . . .
H14A H 0.751620 0.336473 0.300244 0.026 Uiso 1 1 calc R U . . .
H14B H 0.598205 0.264846 0.341554 0.026 Uiso 1 1 calc R U . . .
H14C H 0.794913 0.328537 0.364821 0.026 Uiso 1 1 calc R U . . .
C15 C 0.9851(3) 0.8442(3) 0.32750(9) 0.0187(4) Uani 1 1 d . U . . .
C16 C 1.0220(4) 1.0058(3) 0.35132(10) 0.0286(5) Uani 1 1 d . U . . .
H16A H 1.057178 1.078823 0.321731 0.043 Uiso 1 1 calc R U . . .
H16B H 1.124747 0.999214 0.378133 0.043 Uiso 1 1 calc R U . . .
H16C H 0.907915 1.044534 0.369608 0.043 Uiso 1 1 calc R U . . .
O1 O 0.9117(2) 0.81909(19) 0.44703(6) 0.0230(4) Uani 1 1 d . U . . .
O2 O 0.4284(2) 0.28397(17) 0.42817(6) 0.0193(3) Uani 1 1 d . U . . .
O3 O 0.4278(3) 0.2689(2) 0.52086(7) 0.0401(5) Uani 1 1 d . U . . .
O4 O 1.0599(2) 0.8041(2) 0.28456(6) 0.0279(4) Uani 1 1 d . 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
C1 O1 1.235(3) . ?
C1 C2 1.468(3) . ?
C1 C10 1.483(3) . ?
C2 C3 1.343(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.512(3) . ?
C3 C8 1.521(3) . ?
C4 O2 1.463(3) . ?
C4 C5 1.527(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.526(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.539(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C13 1.530(3) . ?
C7 C8 1.581(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.498(3) . ?
C8 C14 1.562(3) . ?
C9 C10 1.342(3) . ?
C9 H9 0.9500 . ?
C10 C15 1.508(3) . ?
C11 O3 1.203(3) . ?
C11 O2 1.347(3) . ?
C11 C12 1.498(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O4 1.219(3) . ?
C15 C16 1.506(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
O1 C1 C2 121.43(18) . . ?
O1 C1 C10 122.14(19) . . ?
C2 C1 C10 116.41(18) . . ?
C3 C2 C1 123.25(18) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C2 C3 C4 119.40(19) . . ?
C2 C3 C8 122.10(19) . . ?
C4 C3 C8 118.37(18) . . ?
O2 C4 C3 109.54(17) . . ?
O2 C4 C5 107.06(17) . . ?
C3 C4 C5 109.87(17) . . ?
O2 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
C6 C5 C4 111.16(18) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 112.76(18) . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C13 C7 C6 109.82(17) . . ?
C13 C7 C8 113.61(18) . . ?
C6 C7 C8 111.68(17) . . ?
C13 C7 H7 107.1 . . ?
C6 C7 H7 107.1 . . ?
C8 C7 H7 107.1 . . ?
C9 C8 C3 111.66(17) . . ?
C9 C8 C14 106.07(17) . . ?
C3 C8 C14 109.96(16) . . ?
C9 C8 C7 108.57(16) . . ?
C3 C8 C7 108.87(16) . . ?
C14 C8 C7 111.72(17) . . ?
C10 C9 C8 126.38(19) . . ?
C10 C9 H9 116.8 . . ?
C8 C9 H9 116.8 . . ?
C9 C10 C1 119.24(19) . . ?
C9 C10 C15 118.65(19) . . ?
C1 C10 C15 122.10(18) . . ?
O3 C11 O2 124.3(2) . . ?
O3 C11 C12 125.7(2) . . ?
O2 C11 C12 109.96(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C16 120.4(2) . . ?
O4 C15 C10 119.9(2) . . ?
C16 C15 C10 119.68(19) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 O2 C4 118.74(17) . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

