# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_mjx
_database_code_depnum_ccdc_archive 'CCDC 1528333'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.392(3)
_cell_length_b                   9.3651(19)
_cell_length_c                   14.198(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.308(5)
_cell_angle_gamma                90
_cell_volume                     1769.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2483
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      24.53

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9867
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.530
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3280
_reflns_number_gt                2195
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1026P)²+0.0679P] 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     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3280
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1779
_refine_ls_wR_factor_gt          0.1594
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.71132(16) -0.1183(2) 0.33914(15) 0.0526(6) Uani 1 1 d . . . . .
H1 H 0.6801 -0.2060 0.3263 0.063 Uiso 1 1 calc R U . . .
C2 C 0.80481(19) -0.1124(3) 0.39194(18) 0.0699(8) Uani 1 1 d . . . . .
H2 H 0.8360 -0.1966 0.4139 0.084 Uiso 1 1 calc R U . . .
C3 C 0.8515(2) 0.0146(4) 0.41210(18) 0.0735(8) Uani 1 1 d . . . . .
H3 H 0.9137 0.0171 0.4482 0.088 Uiso 1 1 calc R U . . .
C4 C 0.80638(17) 0.1391(3) 0.37896(18) 0.0677(7) Uani 1 1 d . . . . .
H4 H 0.8384 0.2261 0.3921 0.081 Uiso 1 1 calc R U . . .
C5 C 0.71323(16) 0.1352(3) 0.32598(16) 0.0550(6) Uani 1 1 d . . . . .
H5 H 0.6828 0.2198 0.3038 0.066 Uiso 1 1 calc R U . . .
C6 C 0.66487(15) 0.0059(2) 0.30574(14) 0.0404(5) Uani 1 1 d . . . . .
C7 C 0.56340(14) -0.0010(2) 0.24668(14) 0.0391(5) Uani 1 1 d . . . . .
H7 H 0.5522 -0.1007 0.2273 0.047 Uiso 1 1 calc R U . . .
C8 C 0.56621(14) 0.0864(2) 0.15691(13) 0.0409(5) Uani 1 1 d . . . . .
C9 C 0.6279(2) 0.0879(3) 0.00698(16) 0.0760(8) Uani 1 1 d . . . . .
H9A H 0.5647 0.1269 -0.0197 0.114 Uiso 1 1 calc R U . . .
H9B H 0.6518 0.0214 -0.0368 0.114 Uiso 1 1 calc R U . . .
H9C H 0.6758 0.1636 0.0193 0.114 Uiso 1 1 calc R U . . .
C10 C 0.47663(14) 0.0428(2) 0.29890(14) 0.0393(5) Uani 1 1 d . . . . .
C11 C 0.47727(15) 0.1038(2) 0.38260(15) 0.0503(6) Uani 1 1 d . . . . .
H11 H 0.5384 0.1288 0.4161 0.060 Uiso 1 1 calc R U . . .
C12 C 0.38251(16) 0.1335(3) 0.42472(15) 0.0585(6) Uani 1 1 d . . . . .
H12A H 0.3605 0.2304 0.4098 0.070 Uiso 1 1 calc R U . . .
H12B H 0.3938 0.1241 0.4931 0.070 Uiso 1 1 calc R U . . .
C13 C 0.30311(18) 0.0294(3) 0.38539(16) 0.0600(7) Uani 1 1 d . . . . .
H13A H 0.3183 -0.0643 0.4123 0.072 Uiso 1 1 calc R U . . .
H13B H 0.2385 0.0591 0.4035 0.072 Uiso 1 1 calc R U . . .
C14 C 0.29732(16) 0.0207(2) 0.28015(15) 0.0435(5) Uani 1 1 d . . . . .
C15 C 0.21647(15) 0.0128(2) 0.21773(15) 0.0470(5) Uani 1 1 d . . . . .
H15 H 0.2271 0.0019 0.1545 0.056 Uiso 1 1 calc R U . . .
C16 C 0.11239(16) 0.0195(2) 0.23853(16) 0.0504(6) Uani 1 1 d . . . . .
C18 C -0.05776(18) 0.0121(3) 0.1637(2) 0.0776(9) Uani 1 1 d . . . . .
H18 H -0.0725 -0.0075 0.2285 0.093 Uiso 1 1 calc R U . . .
C19 C -0.0898(2) 0.1577(4) 0.1363(3) 0.1314(16) Uani 1 1 d . . . . .
H19A H -0.0474 0.2254 0.1722 0.197 Uiso 1 1 calc R U . . .
H19B H -0.1582 0.1716 0.1489 0.197 Uiso 1 1 calc R U . . .
H19C H -0.0850 0.1713 0.0699 0.197 Uiso 1 1 calc R U . . .
C20 C -0.1055(2) -0.0987(4) 0.0980(3) 0.1099(12) Uani 1 1 d . . . . .
H20A H -0.0944 -0.0756 0.0341 0.165 Uiso 1 1 calc R U . . .
H20B H -0.1763 -0.1017 0.1030 0.165 Uiso 1 1 calc R U . . .
H20C H -0.0764 -0.1902 0.1147 0.165 Uiso 1 1 calc R U . . .
O1 O 0.61467(12) 0.01511(16) 0.09469(10) 0.0565(5) Uani 1 1 d . . . . .
O2 O 0.53282(12) 0.20335(18) 0.14295(11) 0.0688(5) Uani 1 1 d . . . . .
O3 O 0.38773(10) 0.01006(15) 0.24283(10) 0.0496(4) Uani 1 1 d . . . . .
O4 O 0.05012(12) 0.0029(2) 0.15846(12) 0.0694(6) Uani 1 1 d . . . . .
O5 O 0.08260(12) 0.0356(2) 0.31444(13) 0.0829(6) Uani 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 C6 1.379(3) . ?
C1 C2 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.518(3) . ?
C7 C10 1.503(3) . ?
C7 C8 1.519(3) . ?
C7 H7 0.9800 . ?
C8 O2 1.191(2) . ?
C8 O1 1.332(2) . ?
C9 O1 1.447(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.318(3) . ?
C10 O3 1.392(2) . ?
C11 C12 1.487(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.504(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.490(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.324(3) . ?
C14 O3 1.378(2) . ?
C15 C16 1.458(3) . ?
C15 H15 0.9300 . ?
C16 O5 1.199(3) . ?
C16 O4 1.343(3) . ?
C18 O4 1.457(3) . ?
C18 C19 1.469(4) . ?
C18 C20 1.491(4) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C6 C1 C2 119.9(2) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 C7 119.81(18) . . ?
C5 C6 C7 121.35(18) . . ?
C10 C7 C8 111.01(16) . . ?
C10 C7 C6 114.19(16) . . ?
C8 C7 C6 109.73(16) . . ?
C10 C7 H7 107.2 . . ?
C8 C7 H7 107.2 . . ?
C6 C7 H7 107.2 . . ?
O2 C8 O1 123.51(19) . . ?
O2 C8 C7 126.28(18) . . ?
O1 C8 C7 110.19(17) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 O3 122.13(18) . . ?
C11 C10 C7 129.40(18) . . ?
O3 C10 C7 108.47(16) . . ?
C10 C11 C12 121.49(19) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 109.22(18) . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C12 111.39(19) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 O3 115.29(18) . . ?
C15 C14 C13 128.6(2) . . ?
O3 C14 C13 116.01(18) . . ?
C14 C15 C16 126.3(2) . . ?
C14 C15 H15 116.9 . . ?
C16 C15 H15 116.9 . . ?
O5 C16 O4 122.6(2) . . ?
O5 C16 C15 127.4(2) . . ?
O4 C16 C15 110.01(18) . . ?
O4 C18 C19 107.7(2) . . ?
O4 C18 C20 106.6(2) . . ?
C19 C18 C20 112.8(3) . . ?
O4 C18 H18 109.8 . . ?
C19 C18 H18 109.8 . . ?
C20 C18 H18 109.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 O1 C9 116.68(19) . . ?
C14 O3 C10 119.79(15) . . ?
C16 O4 C18 118.50(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
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 179.02(19) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C1 C6 C7 C10 104.7(2) . . . . ?
C5 C6 C7 C10 -76.2(2) . . . . ?
C1 C6 C7 C8 -129.91(19) . . . . ?
C5 C6 C7 C8 49.1(3) . . . . ?
C10 C7 C8 O2 25.8(3) . . . . ?
C6 C7 C8 O2 -101.4(2) . . . . ?
C10 C7 C8 O1 -155.97(16) . . . . ?
C6 C7 C8 O1 76.9(2) . . . . ?
C8 C7 C10 C11 -114.3(2) . . . . ?
C6 C7 C10 C11 10.3(3) . . . . ?
C8 C7 C10 O3 64.9(2) . . . . ?
C6 C7 C10 O3 -170.46(15) . . . . ?
O3 C10 C11 C12 3.7(3) . . . . ?
C7 C10 C11 C12 -177.2(2) . . . . ?
C10 C11 C12 C13 26.3(3) . . . . ?
C11 C12 C13 C14 -48.6(3) . . . . ?
C12 C13 C14 C15 -139.1(2) . . . . ?
C12 C13 C14 O3 45.6(3) . . . . ?
O3 C14 C15 C16 179.33(18) . . . . ?
C13 C14 C15 C16 4.0(4) . . . . ?
C14 C15 C16 O5 1.4(4) . . . . ?
C14 C15 C16 O4 -177.8(2) . . . . ?
O2 C8 O1 C9 1.3(3) . . . . ?
C7 C8 O1 C9 -177.06(18) . . . . ?
C15 C14 O3 C10 168.28(18) . . . . ?
C13 C14 O3 C10 -15.7(3) . . . . ?
C11 C10 O3 C14 -10.1(3) . . . . ?
C7 C10 O3 C14 170.63(15) . . . . ?
O5 C16 O4 C18 3.2(4) . . . . ?
C15 C16 O4 C18 -177.5(2) . . . . ?
C19 C18 O4 C16 97.4(3) . . . . ?
C20 C18 O4 C16 -141.2(3) . . . . ?

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
C13 H13B O5 0.97 2.33 3.014(3) 127.0 .
C13 H13B O5 0.97 2.33 3.014(3) 127.0 .
C13 H13B O5 0.97 2.33 3.014(3) 127.0 .
C13 H13B O5 0.97 2.33 3.014(3) 127.0 .

_refine_diff_density_max         0.419
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.044

_shelxl_version_number           2014/6

