# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_FA1
_database_code_depnum_ccdc_archive 'CCDC 1449366'
_audit_update_record             
;
2016-01-23 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1,2-dihydro-1-(4-hydroxy-3-methoxyphenyl)benzo[f]chromen-3-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 O4'
_chemical_formula_sum            'C20 H16 O4'
_chemical_formula_weight         320.33

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      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                   6.4475(15)
_cell_length_b                   15.152(4)
_cell_length_c                   16.598(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1621.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8649
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.06

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_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            13086
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.820
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2852
_reflns_number_gt                2636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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-2014/7 (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)+(0.0254P)²+0.2124P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0159(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(4)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 1.2044(4) 0.52444(16) -0.03648(13) 0.0574(6) Uani 1 1 d . . . . .
H1 H 1.3166 0.5567 -0.0558 0.069 Uiso 1 1 calc R U . . .
C2 C 1.0879(4) 0.47538(16) -0.08745(12) 0.0575(6) Uani 1 1 d . . . . .
H2 H 1.1204 0.4743 -0.1420 0.069 Uiso 1 1 calc R U . . .
C3 C 0.9171(3) 0.42563(13) -0.05884(11) 0.0442(5) Uani 1 1 d . . . . .
C4 C 0.7931(4) 0.37389(15) -0.11114(13) 0.0576(6) Uani 1 1 d . . . . .
H4 H 0.8231 0.3727 -0.1659 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6311(4) 0.32612(16) -0.08244(14) 0.0640(6) Uani 1 1 d . . . . .
H5 H 0.5493 0.2934 -0.1176 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5870(4) 0.32616(15) 0.00050(15) 0.0599(6) Uani 1 1 d . . . . .
H6 H 0.4775 0.2923 0.0199 0.072 Uiso 1 1 calc R U . . .
C7 C 0.7027(3) 0.37517(13) 0.05299(12) 0.0463(5) Uani 1 1 d . . . . .
H7 H 0.6708 0.3742 0.1076 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8700(3) 0.42732(12) 0.02550(10) 0.0368(4) Uani 1 1 d . . . . .
C9 C 0.9918(3) 0.48041(12) 0.07867(10) 0.0344(4) Uani 1 1 d . . . . .
C10 C 0.9492(3) 0.48754(11) 0.16850(10) 0.0348(4) Uani 1 1 d . . . . .
H10 H 0.7987 0.4850 0.1765 0.042 Uiso 1 1 calc R U . . .
C11 C 1.0250(3) 0.57805(13) 0.19723(12) 0.0466(5) Uani 1 1 d . . . . .
H11A H 0.9308 0.6230 0.1775 0.056 Uiso 1 1 calc R U . . .
H11B H 1.0211 0.5796 0.2556 0.056 Uiso 1 1 calc R U . . .
C12 C 1.2376(4) 0.59933(13) 0.17002(13) 0.0512(5) Uani 1 1 d . . . . .
C13 C 1.1542(3) 0.52620(13) 0.04609(11) 0.0434(5) Uani 1 1 d . . . . .
C14 C 1.0468(3) 0.41387(11) 0.21792(10) 0.0311(4) Uani 1 1 d . . . . .
C15 C 1.2375(3) 0.37839(12) 0.19805(11) 0.0389(4) Uani 1 1 d . . . . .
H15 H 1.3053 0.3971 0.1516 0.047 Uiso 1 1 calc R U . . .
C16 C 1.3287(3) 0.31478(12) 0.24718(11) 0.0407(5) Uani 1 1 d . . . . .
H16 H 1.4575 0.2916 0.2335 0.049 Uiso 1 1 calc R U . . .
C17 C 1.2301(3) 0.28578(11) 0.31588(11) 0.0359(4) Uani 1 1 d . . . . .
C18 C 1.0363(3) 0.32081(12) 0.33680(10) 0.0346(4) Uani 1 1 d . . . . .
C19 C 0.9467(3) 0.38454(11) 0.28821(10) 0.0340(4) Uani 1 1 d . . . . .
H19 H 0.8186 0.4082 0.3023 0.041 Uiso 1 1 calc R U . . .
C20 C 0.7642(3) 0.32657(16) 0.43539(12) 0.0568(6) Uani 1 1 d . . . . .
H20A H 0.7895 0.3875 0.4478 0.085 Uiso 1 1 calc R U . . .
H20B H 0.7196 0.2963 0.4831 0.085 Uiso 1 1 calc R U . . .
H20C H 0.6582 0.3225 0.3949 0.085 Uiso 1 1 calc R U . . .
O1 O 1.2921(2) 0.57606(10) 0.09419(9) 0.0551(4) Uani 1 1 d . . . . .
O2 O 1.3654(3) 0.63885(12) 0.20963(10) 0.0764(5) Uani 1 1 d . . . . .
O3 O 1.3105(3) 0.22346(10) 0.36656(9) 0.0506(4) Uani 1 1 d . . . . .
O4 O 0.9507(2) 0.28704(10) 0.40601(8) 0.0520(4) Uani 1 1 d . . . . .
H1O H 1.417(5) 0.1992(17) 0.3431(15) 0.079(9) 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 C2 1.354(3) . ?
C1 C13 1.409(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.417(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.417(3) . ?
C3 C8 1.433(2) . ?
C4 C5 1.357(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.429(2) . ?
C9 C13 1.367(3) . ?
C9 C10 1.520(2) . ?
C10 C14 1.521(2) . ?
C10 C11 1.532(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.479(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O2 1.212(3) . ?
C12 O1 1.354(3) . ?
C13 O1 1.414(2) . ?
C14 C15 1.382(3) . ?
C14 C19 1.405(2) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 O3 1.367(2) . ?
C17 C18 1.401(3) . ?
C18 O4 1.374(2) . ?
C18 C19 1.385(2) . ?
C19 H19 0.9300 . ?
C20 O4 1.429(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O3 H1O 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C13 119.39(19) . . ?
C2 C1 H1 120.3 . . ?
C13 C1 H1 120.3 . . ?
C1 C2 C3 120.94(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.84(19) . . ?
C2 C3 C8 118.87(18) . . ?
C4 C3 C8 119.29(19) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 122.34(16) . . ?
C7 C8 C3 117.85(17) . . ?
C9 C8 C3 119.80(17) . . ?
C13 C9 C8 117.53(17) . . ?
C13 C9 C10 119.37(16) . . ?
C8 C9 C10 123.11(15) . . ?
C9 C10 C14 113.70(14) . . ?
C9 C10 C11 108.14(15) . . ?
C14 C10 C11 110.91(15) . . ?
C9 C10 H10 108.0 . . ?
C14 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C12 C11 C10 113.32(17) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
O2 C12 O1 117.2(2) . . ?
O2 C12 C11 124.9(2) . . ?
O1 C12 C11 117.90(18) . . ?
C9 C13 C1 123.46(19) . . ?
C9 C13 O1 121.97(17) . . ?
C1 C13 O1 114.50(17) . . ?
C15 C14 C19 118.93(16) . . ?
C15 C14 C10 121.65(15) . . ?
C19 C14 C10 119.31(16) . . ?
C14 C15 C16 120.34(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.71(18) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
O3 C17 C16 123.72(18) . . ?
O3 C17 C18 116.56(17) . . ?
C16 C17 C18 119.72(16) . . ?
O4 C18 C19 125.38(18) . . ?
O4 C18 C17 115.13(16) . . ?
C19 C18 C17 119.48(16) . . ?
C18 C19 C14 120.82(17) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 O1 C13 120.05(16) . . ?
C17 O3 H1O 108.4(17) . . ?
C18 O4 C20 117.88(15) . . ?

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
C13 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 180.0(2) . . . . ?
C1 C2 C3 C8 -0.5(3) . . . . ?
C2 C3 C4 C5 179.5(2) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 178.97(19) . . . . ?
C6 C7 C8 C3 -1.3(3) . . . . ?
C2 C3 C8 C7 -178.19(19) . . . . ?
C4 C3 C8 C7 1.3(3) . . . . ?
C2 C3 C8 C9 1.5(3) . . . . ?
C4 C3 C8 C9 -178.97(18) . . . . ?
C7 C8 C9 C13 178.03(18) . . . . ?
C3 C8 C9 C13 -1.7(3) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C3 C8 C9 C10 178.55(16) . . . . ?
C13 C9 C10 C14 -95.2(2) . . . . ?
C8 C9 C10 C14 84.6(2) . . . . ?
C13 C9 C10 C11 28.5(2) . . . . ?
C8 C9 C10 C11 -151.77(17) . . . . ?
C9 C10 C11 C12 -48.8(2) . . . . ?
C14 C10 C11 C12 76.5(2) . . . . ?
C10 C11 C12 O2 -143.0(2) . . . . ?
C10 C11 C12 O1 39.6(2) . . . . ?
C8 C9 C13 C1 0.9(3) . . . . ?
C10 C9 C13 C1 -179.3(2) . . . . ?
C8 C9 C13 O1 -175.87(17) . . . . ?
C10 C9 C13 O1 3.9(3) . . . . ?
C2 C1 C13 C9 0.1(4) . . . . ?
C2 C1 C13 O1 177.1(2) . . . . ?
C9 C10 C14 C15 35.6(2) . . . . ?
C11 C10 C14 C15 -86.5(2) . . . . ?
C9 C10 C14 C19 -148.14(16) . . . . ?
C11 C10 C14 C19 89.7(2) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C10 C14 C15 C16 176.08(16) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 O3 179.82(17) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
O3 C17 C18 O4 -0.5(2) . . . . ?
C16 C17 C18 O4 179.55(17) . . . . ?
O3 C17 C18 C19 179.69(16) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
O4 C18 C19 C14 -179.24(17) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C10 C14 C19 C18 -176.67(16) . . . . ?
O2 C12 O1 C13 177.00(19) . . . . ?
C11 C12 O1 C13 -5.4(3) . . . . ?
C9 C13 O1 C12 -17.7(3) . . . . ?
C1 C13 O1 C12 165.3(2) . . . . ?
C19 C18 O4 C20 -6.8(3) . . . . ?
C17 C18 O4 C20 173.41(16) . . . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.024



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1454627'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-07-11 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            'C20 H21 N O5'
_chemical_formula_weight         355.38

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'
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                   8.4538(6)
_cell_length_b                   10.1122(6)
_cell_length_c                   11.6442(7)
_cell_angle_alpha                66.970(3)
_cell_angle_beta                 85.590(3)
_cell_angle_gamma                84.250(3)
_cell_volume                     910.71(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21027
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.902
_diffrn_reflns_theta_max         29.626
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4592
_reflns_number_gt                2742
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0587P)²+0.2417P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4592
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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 0.0658(2) 0.66982(16) 0.90189(15) 0.0415(4) Uani 1 1 d . . . . .
C2 C -0.0082(3) 0.7181(2) 0.98931(19) 0.0587(5) Uani 1 1 d . . . . .
H2 H -0.1175 0.7411 0.9873 0.070 Uiso 1 1 calc R U . . .
C3 C 0.0754(4) 0.7331(2) 1.0791(2) 0.0756(7) Uani 1 1 d . . . . .
H3 H 0.0225 0.7646 1.1379 0.091 Uiso 1 1 calc R U . . .
C4 C 0.2352(4) 0.7020(3) 1.0826(2) 0.0792(8) Uani 1 1 d . . . . .
H4 H 0.2923 0.7137 1.1427 0.095 Uiso 1 1 calc R U . . .
C5 C 0.3120(3) 0.6534(3) 0.9969(2) 0.0791(7) Uani 1 1 d . . . . .
H5 H 0.4215 0.6316 0.9990 0.095 Uiso 1 1 calc R U . . .
C6 C 0.2265(2) 0.6367(2) 0.90733(18) 0.0584(5) Uani 1 1 d . . . . .
H6 H 0.2791 0.6024 0.8502 0.070 Uiso 1 1 calc R U . . .
C7 C -0.0330(2) 0.65817(19) 0.80548(16) 0.0445(4) Uani 1 1 d . . . . .
H7A H -0.1200 0.5993 0.8480 0.053 Uiso 1 1 calc R U . . .
H7B H -0.0792 0.7536 0.7559 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1313(2) 0.67785(16) 0.62074(15) 0.0377(4) Uani 1 1 d . . . . .
C9 C 0.2066(2) 0.60672(16) 0.53654(15) 0.0395(4) Uani 1 1 d . . . . .
H9A H 0.1668 0.6566 0.4533 0.047 Uiso 1 1 calc R U . . .
H9B H 0.3209 0.6127 0.5311 0.047 Uiso 1 1 calc R U . . .
C10 C 0.23644(19) 0.38293(16) 0.51443(15) 0.0347(4) Uani 1 1 d . . . . .
C11 C 0.19453(19) 0.24016(16) 0.55695(14) 0.0339(4) Uani 1 1 d . . . . .
C12 C 0.25574(19) 0.15387(16) 0.49522(15) 0.0363(4) Uani 1 1 d . . . . .
H12 H 0.2279 0.0593 0.5233 0.044 Uiso 1 1 calc R U . . .
C13 C 0.35931(19) 0.20633(16) 0.39081(15) 0.0369(4) Uani 1 1 d . . . . .
C14 C 0.3971(2) 0.34755(17) 0.35051(16) 0.0428(4) Uani 1 1 d . . . . .
H14 H 0.4649 0.3844 0.2805 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3368(2) 0.43539(17) 0.41169(16) 0.0415(4) Uani 1 1 d . . . . .
H15 H 0.3644 0.5301 0.3831 0.050 Uiso 1 1 calc R U . . .
C16 C 0.0446(3) 0.05586(19) 0.70272(19) 0.0578(5) Uani 1 1 d . . . . .
H16A H -0.0052 0.0426 0.6371 0.087 Uiso 1 1 calc R U . . .
H16B H -0.0294 0.0401 0.7727 0.087 Uiso 1 1 calc R U . . .
H16C H 0.1361 -0.0115 0.7279 0.087 Uiso 1 1 calc R U . . .
C17 C 0.4256(2) 0.11878(17) 0.32222(16) 0.0404(4) Uani 1 1 d . . . . .
H17 H 0.4981 0.1610 0.2568 0.048 Uiso 1 1 calc R U . . .
C18 C 0.3940(2) -0.01375(18) 0.34267(16) 0.0427(4) Uani 1 1 d . . . . .
H18 H 0.3215 -0.0579 0.4075 0.051 Uiso 1 1 calc R U . . .
C19 C 0.4652(2) -0.09602(18) 0.27032(16) 0.0433(4) Uani 1 1 d . . . . .
C20 C 0.6485(3) -0.1064(2) 0.1120(2) 0.0689(6) Uani 1 1 d . . . . .
H20A H 0.7217 -0.0473 0.0507 0.103 Uiso 1 1 calc R U . . .
H20B H 0.7055 -0.1915 0.1677 0.103 Uiso 1 1 calc R U . . .
H20C H 0.5706 -0.1333 0.0710 0.103 Uiso 1 1 calc R U . . .
N1 N 0.05017(18) 0.59788(15) 0.72201(13) 0.0419(4) Uani 1 1 d . . . . .
O1 O 0.14871(17) 0.80476(12) 0.59403(12) 0.0570(4) Uani 1 1 d . . . . .
O2 O 0.17207(15) 0.46005(11) 0.58272(11) 0.0440(3) Uani 1 1 d . . . . .
O3 O 0.09275(15) 0.19910(11) 0.65884(11) 0.0457(3) Uani 1 1 d . . . . .
O4 O 0.4338(2) -0.21527(15) 0.28813(14) 0.0707(4) Uani 1 1 d . . . . .
O5 O 0.57021(16) -0.02707(14) 0.18185(13) 0.0587(4) Uani 1 1 d . . . . .
H1A H 0.042(2) 0.512(2) 0.7313(18) 0.053(6) 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 C6 1.366(3) . ?
C1 C2 1.377(2) . ?
C1 C7 1.496(2) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.444(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.2182(17) . ?
C8 N1 1.325(2) . ?
C8 C9 1.499(2) . ?
C9 O2 1.4186(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.3675(18) . ?
C10 C15 1.368(2) . ?
C10 C11 1.404(2) . ?
C11 O3 1.3600(18) . ?
C11 C12 1.374(2) . ?
C12 C13 1.397(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(2) . ?
C13 C17 1.456(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O3 1.4254(19) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.318(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.461(2) . ?
C18 H18 0.9300 . ?
C19 O4 1.195(2) . ?
C19 O5 1.326(2) . ?
C20 O5 1.437(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 H1A 0.841(19) . ?

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 117.86(18) . . ?
C6 C1 C7 123.59(15) . . ?
C2 C1 C7 118.54(17) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.8(2) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
N1 C7 C1 115.57(15) . . ?
N1 C7 H7A 108.4 . . ?
C1 C7 H7A 108.4 . . ?
N1 C7 H7B 108.4 . . ?
C1 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 N1 123.29(15) . . ?
O1 C8 C9 118.95(14) . . ?
N1 C8 C9 117.76(13) . . ?
O2 C9 C8 110.54(13) . . ?
O2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O2 C10 C15 124.53(13) . . ?
O2 C10 C11 115.57(13) . . ?
C15 C10 C11 119.90(14) . . ?
O3 C11 C12 125.13(13) . . ?
O3 C11 C10 115.28(13) . . ?
C12 C11 C10 119.59(14) . . ?
C11 C12 C13 120.84(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 118.24(14) . . ?
C14 C13 C17 119.24(15) . . ?
C12 C13 C17 122.51(14) . . ?
C15 C14 C13 121.56(16) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C10 C15 C14 119.86(14) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C13 127.13(16) . . ?
C18 C17 H17 116.4 . . ?
C13 C17 H17 116.4 . . ?
C17 C18 C19 124.41(16) . . ?
C17 C18 H18 117.8 . . ?
C19 C18 H18 117.8 . . ?
O4 C19 O5 121.94(16) . . ?
O4 C19 C18 123.97(17) . . ?
O5 C19 C18 114.09(14) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 C7 121.84(14) . . ?
C8 N1 H1A 116.5(13) . . ?
C7 N1 H1A 121.4(13) . . ?
C10 O2 C9 115.99(12) . . ?
C11 O3 C16 116.77(12) . . ?
C19 O5 C20 115.99(15) . . ?

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 0.1(3) . . . . ?
C7 C1 C2 C3 -179.16(18) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C7 C1 C6 C5 178.26(19) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C6 C1 C7 N1 4.7(2) . . . . ?
C2 C1 C7 N1 -176.06(15) . . . . ?
O1 C8 C9 O2 -179.63(15) . . . . ?
N1 C8 C9 O2 1.2(2) . . . . ?
O2 C10 C11 O3 1.4(2) . . . . ?
C15 C10 C11 O3 -179.28(15) . . . . ?
O2 C10 C11 C12 -178.95(14) . . . . ?
C15 C10 C11 C12 0.4(2) . . . . ?
O3 C11 C12 C13 179.75(15) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
C11 C12 C13 C17 -179.44(15) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C17 C13 C14 C15 179.60(16) . . . . ?
O2 C10 C15 C14 179.01(16) . . . . ?
C11 C10 C15 C14 -0.3(3) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C14 C13 C17 C18 -175.24(18) . . . . ?
C12 C13 C17 C18 3.5(3) . . . . ?
C13 C17 C18 C19 -179.83(16) . . . . ?
C17 C18 C19 O4 -178.65(19) . . . . ?
C17 C18 C19 O5 1.7(3) . . . . ?
O1 C8 N1 C7 3.9(3) . . . . ?
C9 C8 N1 C7 -176.92(15) . . . . ?
C1 C7 N1 C8 -84.1(2) . . . . ?
C15 C10 O2 C9 4.0(2) . . . . ?
C11 C10 O2 C9 -176.63(14) . . . . ?
C8 C9 O2 C10 -179.14(14) . . . . ?
C12 C11 O3 C16 -1.2(2) . . . . ?
C10 C11 O3 C16 178.52(16) . . . . ?
O4 C19 O5 C20 -2.3(3) . . . . ?
C18 C19 O5 C20 177.32(17) . . . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.056



