# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 2079932'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2021-06-11 deposited with the CCDC.	2021-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'benzyl (E)-2-((4-(benzyloxy)-4-oxobut-2-en-2-yl)oxy)-7-ethoxy-5H-chromeno[3,4-b]pyridine-3-carboxylate'
_chemical_name_common            ?
_chemical_formula_moiety         'C33 H29 N O7'
_chemical_formula_sum            'C33 H29 N O7'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         551.57

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'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   10.646(2)
_cell_length_b                   11.634(3)
_cell_length_c                   12.087(3)
_cell_angle_alpha                101.823(13)
_cell_angle_beta                 109.747(10)
_cell_angle_gamma                91.715(13)
_cell_volume                     1371.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    31917
_cell_measurement_theta_min      2.561
_cell_measurement_theta_max      25.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6106
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33320
_diffrn_reflns_av_unetI/netI     0.3266
_diffrn_reflns_av_R_equivalents  0.1499
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5500
_reflns_number_gt                4099
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0457P)²+0.3809P] 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_number_reflns         5500
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O17 O 0.42133(10) 0.21594(9) 0.44239(11) 0.0208(3) Uani 1 1 d . . . . .
O11 O 0.75781(10) -0.02974(9) 0.42883(10) 0.0188(2) Uani 1 1 d . . . . .
O35 O 1.18033(11) 0.47849(10) 1.05970(10) 0.0229(3) Uani 1 1 d . . . . .
O6 O 1.13448(11) 0.39201(9) 0.82864(10) 0.0205(2) Uani 1 1 d . . . . .
O26 O 0.96711(13) 0.17194(12) 0.28250(11) 0.0319(3) Uani 1 1 d . . . . .
O27 O 0.77761(11) 0.05985(10) 0.25169(11) 0.0249(3) Uani 1 1 d . . . . .
O16 O 0.34352(11) 0.05007(10) 0.29514(11) 0.0245(3) Uani 1 1 d . . . . .
N4 N 1.02194(12) 0.21826(11) 0.52582(12) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.92190(14) 0.13384(12) 0.45337(14) 0.0166(3) Uani 1 1 d . . . . .
C22 C 0.2885(2) 0.60661(15) 0.60014(19) 0.0334(4) Uani 1 1 d . . . . .
H22 H 0.287558 0.683164 0.641518 0.040 Uiso 1 1 calc R U . . .
C21 C 0.4058(2) 0.55200(16) 0.62781(19) 0.0338(4) Uani 1 1 d . . . . .
H21 H 0.483626 0.592153 0.688007 0.041 Uiso 1 1 calc R U . . .
C20 C 0.40741(17) 0.43755(15) 0.56599(17) 0.0273(4) Uani 1 1 d . . . . .
H20 H 0.486516 0.401752 0.584947 0.033 Uiso 1 1 calc R U . . .
C19 C 0.29138(16) 0.37613(13) 0.47585(15) 0.0192(3) Uani 1 1 d . . . . .
C18 C 0.28665(15) 0.25087(14) 0.40817(16) 0.0214(3) Uani 1 1 d . . . . .
H18A H 0.228660 0.198588 0.427658 0.026 Uiso 1 1 calc R U . . .
H18B H 0.250831 0.245684 0.321884 0.026 Uiso 1 1 calc R U . . .
C15 C 0.43662(15) 0.11153(12) 0.37682(14) 0.0170(3) Uani 1 1 d . . . . .
C14 C 0.57800(15) 0.08942(13) 0.42128(14) 0.0177(3) Uani 1 1 d . . . . .
H14 H 0.639433 0.149512 0.478663 0.021 Uiso 1 1 calc R U . . .
C12 C 0.62419(15) -0.01181(13) 0.38448(14) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.85280(14) 0.06508(12) 0.50164(14) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.88590(15) 0.08413(12) 0.62570(15) 0.0170(3) Uani 1 1 d . . . . .
H1 H 0.840108 0.039308 0.658379 0.020 Uiso 1 1 calc R U . . .
C10B C 0.98904(15) 0.17166(12) 0.70064(14) 0.0166(3) Uani 1 1 d . . . . .
C10A C 1.02946(14) 0.20570(13) 0.83284(15) 0.0177(3) Uani 1 1 d . . . . .
C6A C 1.09665(15) 0.31874(13) 0.89067(15) 0.0176(3) Uani 1 1 d . . . . .
C7 C 1.11914(15) 0.36536(13) 1.01394(15) 0.0193(3) Uani 1 1 d . . . . .
C36 C 1.20132(16) 0.52888(14) 1.18501(15) 0.0223(3) Uani 1 1 d . . . . .
H36A H 1.255680 0.481172 1.235983 0.027 Uiso 1 1 calc R U . . .
H36B H 1.116005 0.532309 1.197415 0.027 Uiso 1 1 calc R U . . .
C37 C 1.27217(19) 0.65142(15) 1.21547(17) 0.0302(4) Uani 1 1 d . . . . .
H37A H 1.358752 0.646495 1.207664 0.045 Uiso 1 1 calc R U . . .
H37C H 1.282987 0.689642 1.296948 0.045 Uiso 1 1 calc R U . . .
H37B H 1.219913 0.696193 1.161227 0.045 Uiso 1 1 calc R U . . .
C8 C 1.07996(16) 0.29456(14) 1.07891(15) 0.0217(3) Uani 1 1 d . . . . .
H8 H 1.092969 0.324348 1.159939 0.026 Uiso 1 1 calc R U . . .
C9 C 1.02107(16) 0.17875(14) 1.02284(16) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.999969 0.130789 1.068278 0.028 Uiso 1 1 calc R U . . .
C10 C 0.99381(16) 0.13458(14) 0.90132(16) 0.0213(3) Uani 1 1 d . . . . .
H10 H 0.952085 0.058219 0.864659 0.026 Uiso 1 1 calc R U . . .
C5 C 1.16578(16) 0.32994(14) 0.72637(15) 0.0223(3) Uani 1 1 d . . . . .
H15 H 1.247814 0.293387 0.754777 0.027 Uiso 1 1 calc R U . . .
H16 H 1.180602 0.385746 0.681243 0.027 Uiso 1 1 calc R U . . .
C4A C 1.05348(15) 0.23636(13) 0.64464(14) 0.0166(3) Uani 1 1 d . . . . .
C25 C 0.89399(15) 0.12465(13) 0.32068(15) 0.0184(3) Uani 1 1 d . . . . .
C28 C 0.73060(17) 0.05753(15) 0.12271(16) 0.0258(4) Uani 1 1 d . . . . .
H28B H 0.680254 -0.018252 0.077182 0.031 Uiso 1 1 calc R U . . .
H28A H 0.806968 0.067460 0.097676 0.031 Uiso 1 1 calc R U . . .
C29 C 0.64278(16) 0.15484(15) 0.09676(15) 0.0237(4) Uani 1 1 d . . . . .
C34 C 0.51589(17) 0.14780(15) 0.10664(16) 0.0261(4) Uani 1 1 d . . . . .
H34 H 0.487198 0.083490 0.130075 0.031 Uiso 1 1 calc R U . . .
C33 C 0.43239(18) 0.23529(17) 0.08202(18) 0.0325(4) Uani 1 1 d . . . . .
H33 H 0.347903 0.229457 0.088410 0.039 Uiso 1 1 calc R U . . .
C32 C 0.4751(2) 0.33175(17) 0.04777(19) 0.0382(5) Uani 1 1 d . . . . .
H32 H 0.418895 0.390241 0.030063 0.046 Uiso 1 1 calc R U . . .
C31 C 0.6021(2) 0.34076(18) 0.0400(2) 0.0409(5) Uani 1 1 d . . . . .
H31 H 0.631532 0.406236 0.018685 0.049 Uiso 1 1 calc R U . . .
C30 C 0.68544(19) 0.25243(17) 0.06387(18) 0.0321(4) Uani 1 1 d . . . . .
H30 H 0.770063 0.258651 0.057835 0.038 Uiso 1 1 calc R U . . .
C13 C 0.54690(16) -0.12069(13) 0.29450(17) 0.0250(4) Uani 1 1 d . . . . .
H13A H 0.452497 -0.115019 0.275559 0.038 Uiso 1 1 calc R U . . .
H13C H 0.570493 -0.188524 0.327804 0.038 Uiso 1 1 calc R U . . .
H13B H 0.568071 -0.128485 0.222326 0.038 Uiso 1 1 calc R U . . .
C24 C 0.17381(17) 0.43169(14) 0.44838(16) 0.0225(3) Uani 1 1 d . . . . .
H24 H 0.095677 0.391889 0.388277 0.027 Uiso 1 1 calc R U . . .
C23 C 0.17296(18) 0.54618(15) 0.51042(18) 0.0294(4) Uani 1 1 d . . . . .
H23 H 0.094189 0.582466 0.491532 0.035 Uiso 1 1 calc R 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
O17 C15 1.3544(19) . ?
O17 C18 1.4474(19) . ?
O11 C12 1.3795(19) . ?
O11 C2 1.3958(18) . ?
O35 C7 1.3672(19) . ?
O35 C36 1.445(2) . ?
O6 C6A 1.3771(19) . ?
O6 C5 1.445(2) . ?
O26 C25 1.201(2) . ?
O27 C25 1.3368(19) . ?
O27 C28 1.462(2) . ?
O16 C15 1.2147(19) . ?
N4 C4A 1.329(2) . ?
N4 C3 1.3492(19) . ?
C3 C2 1.403(2) . ?
C3 C25 1.509(2) . ?
C22 C23 1.385(3) . ?
C22 C21 1.388(3) . ?
C22 H22 0.9300 . ?
C21 C20 1.391(3) . ?
C21 H21 0.9300 . ?
C20 C19 1.394(2) . ?
C20 H20 0.9300 . ?
C19 C24 1.397(2) . ?
C19 C18 1.508(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C15 C14 1.468(2) . ?
C14 C12 1.340(2) . ?
C14 H14 0.9300 . ?
C12 C13 1.494(2) . ?
C2 C1 1.387(2) . ?
C1 C10B 1.395(2) . ?
C1 H1 0.9300 . ?
C10B C4A 1.410(2) . ?
C10B C10A 1.470(2) . ?
C10A C6A 1.400(2) . ?
C10A C10 1.410(2) . ?
C6A C7 1.411(2) . ?
C7 C8 1.391(2) . ?
C36 C37 1.507(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37C 0.9600 . ?
C37 H37B 0.9600 . ?
C8 C9 1.398(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C5 C4A 1.508(2) . ?
C5 H15 0.9700 . ?
C5 H16 0.9700 . ?
C28 C29 1.505(3) . ?
C28 H28B 0.9700 . ?
C28 H28A 0.9700 . ?
C29 C30 1.389(3) . ?
C29 C34 1.397(2) . ?
C34 C33 1.384(3) . ?
C34 H34 0.9300 . ?
C33 C32 1.387(3) . ?
C33 H33 0.9300 . ?
C32 C31 1.389(3) . ?
C32 H32 0.9300 . ?
C31 C30 1.389(3) . ?
C31 H31 0.9300 . ?
C30 H30 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13C 0.9600 . ?
C13 H13B 0.9600 . ?
C24 C23 1.390(2) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?

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
C15 O17 C18 115.74(12) . . ?
C12 O11 C2 119.56(11) . . ?
C7 O35 C36 116.61(12) . . ?
C6A O6 C5 113.81(12) . . ?
C25 O27 C28 117.07(13) . . ?
C4A N4 C3 118.76(13) . . ?
N4 C3 C2 121.09(14) . . ?
N4 C3 C25 113.34(13) . . ?
C2 C3 C25 125.56(13) . . ?
C23 C22 C21 119.46(16) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C21 C20 120.36(17) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C20 C19 120.47(16) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C19 C24 118.86(15) . . ?
C20 C19 C18 122.68(15) . . ?
C24 C19 C18 118.45(14) . . ?
O17 C18 C19 108.76(12) . . ?
O17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
O17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O16 C15 O17 122.51(14) . . ?
O16 C15 C14 128.32(14) . . ?
O17 C15 C14 109.18(12) . . ?
C12 C14 C15 124.16(13) . . ?
C12 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C14 C12 O11 122.58(13) . . ?
C14 C12 C13 128.27(14) . . ?
O11 C12 C13 109.14(13) . . ?
C1 C2 O11 117.91(13) . . ?
C1 C2 C3 120.04(13) . . ?
O11 C2 C3 121.84(14) . . ?
C2 C1 C10B 118.89(14) . . ?
C2 C1 H1 120.6 . . ?
C10B C1 H1 120.6 . . ?
C1 C10B C4A 117.36(15) . . ?
C1 C10B C10A 124.64(14) . . ?
C4A C10B C10A 117.89(13) . . ?
C6A C10A C10 119.22(15) . . ?
C6A C10A C10B 117.35(13) . . ?
C10 C10A C10B 123.20(14) . . ?
O6 C6A C10A 121.85(14) . . ?
O6 C6A C7 117.25(13) . . ?
C10A C6A C7 120.73(14) . . ?
O35 C7 C8 125.43(15) . . ?
O35 C7 C6A 115.74(13) . . ?
C8 C7 C6A 118.83(14) . . ?
O35 C36 C37 107.07(13) . . ?
O35 C36 H36A 110.3 . . ?
C37 C36 H36A 110.3 . . ?
O35 C36 H36B 110.3 . . ?
C37 C36 H36B 110.3 . . ?
H36A C36 H36B 108.6 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37C C37 H37B 109.5 . . ?
C7 C8 C9 120.26(16) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 121.05(15) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C10A 119.69(15) . . ?
C9 C10 H10 120.2 . . ?
C10A C10 H10 120.2 . . ?
O6 C5 C4A 111.09(13) . . ?
O6 C5 H15 109.4 . . ?
C4A C5 H15 109.4 . . ?
O6 C5 H16 109.4 . . ?
C4A C5 H16 109.4 . . ?
H15 C5 H16 108.0 . . ?
N4 C4A C10B 123.85(14) . . ?
N4 C4A C5 119.14(13) . . ?
C10B C4A C5 117.00(14) . . ?
O26 C25 O27 124.42(15) . . ?
O26 C25 C3 123.61(14) . . ?
O27 C25 C3 111.95(13) . . ?
O27 C28 C29 110.13(14) . . ?
O27 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
O27 C28 H28A 109.6 . . ?
C29 C28 H28A 109.6 . . ?
H28B C28 H28A 108.1 . . ?
C30 C29 C34 119.01(17) . . ?
C30 C29 C28 121.42(16) . . ?
C34 C29 C28 119.58(16) . . ?
C33 C34 C29 120.85(17) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?
C34 C33 C32 119.76(17) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C32 C31 119.85(18) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C30 C31 C32 120.29(18) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C30 C29 120.22(18) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
C23 C24 C19 120.35(16) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C22 C23 C24 120.50(17) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?

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
C4A N4 C3 C2 -0.7(2) . . . . ?
C4A N4 C3 C25 178.49(13) . . . . ?
C23 C22 C21 C20 0.0(3) . . . . ?
C22 C21 C20 C19 -0.2(3) . . . . ?
C21 C20 C19 C24 0.3(3) . . . . ?
C21 C20 C19 C18 -178.42(17) . . . . ?
C15 O17 C18 C19 -171.12(13) . . . . ?
C20 C19 C18 O17 -7.0(2) . . . . ?
C24 C19 C18 O17 174.31(14) . . . . ?
C18 O17 C15 O16 -0.7(2) . . . . ?
C18 O17 C15 C14 179.34(13) . . . . ?
O16 C15 C14 C12 -7.4(3) . . . . ?
O17 C15 C14 C12 172.62(15) . . . . ?
C15 C14 C12 O11 -179.61(14) . . . . ?
C15 C14 C12 C13 -0.2(3) . . . . ?
C2 O11 C12 C14 -9.4(2) . . . . ?
C2 O11 C12 C13 171.10(13) . . . . ?
C12 O11 C2 C1 92.54(17) . . . . ?
C12 O11 C2 C3 -92.74(17) . . . . ?
N4 C3 C2 C1 0.7(2) . . . . ?
C25 C3 C2 C1 -178.37(14) . . . . ?
N4 C3 C2 O11 -173.92(13) . . . . ?
C25 C3 C2 O11 7.0(2) . . . . ?
O11 C2 C1 C10B 174.35(13) . . . . ?
C3 C2 C1 C10B -0.5(2) . . . . ?
C2 C1 C10B C4A 0.3(2) . . . . ?
C2 C1 C10B C10A 176.43(14) . . . . ?
C1 C10B C10A C6A -157.14(14) . . . . ?
C4A C10B C10A C6A 19.0(2) . . . . ?
C1 C10B C10A C10 17.3(2) . . . . ?
C4A C10B C10A C10 -166.60(14) . . . . ?
C5 O6 C6A C10A -30.99(19) . . . . ?
C5 O6 C6A C7 153.72(14) . . . . ?
C10 C10A C6A O6 179.74(14) . . . . ?
C10B C10A C6A O6 -5.6(2) . . . . ?
C10 C10A C6A C7 -5.1(2) . . . . ?
C10B C10A C6A C7 169.50(14) . . . . ?
C36 O35 C7 C8 -2.2(2) . . . . ?
C36 O35 C7 C6A 178.55(13) . . . . ?
O6 C6A C7 O35 -1.8(2) . . . . ?
C10A C6A C7 O35 -177.17(13) . . . . ?
O6 C6A C7 C8 178.85(14) . . . . ?
C10A C6A C7 C8 3.5(2) . . . . ?
C7 O35 C36 C37 178.74(13) . . . . ?
O35 C7 C8 C9 -178.37(15) . . . . ?
C6A C7 C8 C9 0.9(2) . . . . ?
C7 C8 C9 C10 -3.6(2) . . . . ?
C8 C9 C10 C10A 2.0(2) . . . . ?
C6A C10A C10 C9 2.4(2) . . . . ?
C10B C10A C10 C9 -171.93(14) . . . . ?
C6A O6 C5 C4A 52.05(17) . . . . ?
C3 N4 C4A C10B 0.5(2) . . . . ?
C3 N4 C4A C5 179.58(13) . . . . ?
C1 C10B C4A N4 -0.3(2) . . . . ?
C10A C10B C4A N4 -176.70(13) . . . . ?
C1 C10B C4A C5 -179.40(13) . . . . ?
C10A C10B C4A C5 4.2(2) . . . . ?
O6 C5 C4A N4 141.80(14) . . . . ?
O6 C5 C4A C10B -39.04(19) . . . . ?
C28 O27 C25 O26 -6.8(2) . . . . ?
C28 O27 C25 C3 171.98(13) . . . . ?
N4 C3 C25 O26 12.4(2) . . . . ?
C2 C3 C25 O26 -168.47(16) . . . . ?
N4 C3 C25 O27 -166.38(12) . . . . ?
C2 C3 C25 O27 12.7(2) . . . . ?
C25 O27 C28 C29 -90.77(17) . . . . ?
O27 C28 C29 C30 109.66(18) . . . . ?
O27 C28 C29 C34 -69.87(19) . . . . ?
C30 C29 C34 C33 1.2(3) . . . . ?
C28 C29 C34 C33 -179.27(16) . . . . ?
C29 C34 C33 C32 -0.4(3) . . . . ?
C34 C33 C32 C31 -0.9(3) . . . . ?
C33 C32 C31 C30 1.4(3) . . . . ?
C32 C31 C30 C29 -0.6(3) . . . . ?
C34 C29 C30 C31 -0.7(3) . . . . ?
C28 C29 C30 C31 179.76(18) . . . . ?
C20 C19 C24 C23 -0.2(2) . . . . ?
C18 C19 C24 C23 178.58(15) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C19 C24 C23 C22 0.0(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
_geom_hbond_publ_flag
C1 H1 O16 0.93 2.47 3.359(2) 161.1 2_656 yes
C13 H13A O16 0.96 2.29 2.983(2) 128.8 . yes

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.184




####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2079933'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2021-06-11 deposited with the CCDC.	2021-10-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'Benzyl 2-hydroxy-8,10-dimethoxy-5H-chromeno[3,4-b]pyridine-3-carboxylate'
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H19 N O6'
_chemical_formula_sum            'C22 H19 N O6'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         393.38

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'
_chemical_absolute_configuration ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_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.
;

_cell_length_a                   8.708(2)
_cell_length_b                   13.624(4)
_cell_length_c                   17.004(5)
_cell_angle_alpha                66.753(6)
_cell_angle_beta                 79.781(7)
_cell_angle_gamma                88.762(7)
_cell_volume                     1821.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.78
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5276
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64553
_diffrn_reflns_av_unetI/netI     0.1178
_diffrn_reflns_av_R_equivalents  0.2185
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.653
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6676
_reflns_number_gt                3564
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  WinGX
_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)+(0.0436P)²+3.8242P] 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_number_reflns         6676
_refine_ls_number_parameters     529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1917
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O3A O -0.0489(4) 0.7745(2) 0.4295(2) 0.0410(8) Uani 1 1 d . . . . .
O2A O -0.0144(4) 0.9070(3) 0.4722(2) 0.0508(9) Uani 1 1 d . . . . .
O4 O 0.4458(4) 0.8274(2) 0.4171(2) 0.0438(9) Uani 1 1 d . . . . .
O6 O 0.6182(4) 0.5035(2) 0.6073(2) 0.0437(9) Uani 1 1 d . . . . .
O3 O 0.9475(4) 0.2966(2) 0.9163(2) 0.0436(8) Uani 1 1 d . . . . .
O2 O 0.9721(4) 0.4211(3) 0.9681(2) 0.0566(10) Uani 1 1 d . . . . .
O4A O 0.4356(4) 0.2284(3) 0.9237(2) 0.0591(10) Uani 1 1 d . . . . .
O1A O 0.0988(5) 0.8624(3) 0.6164(2) 0.0637(11) Uani 1 1 d . . . . .
H1C H 0.060430 0.901630 0.574898 0.096 Uiso 1 1 calc R U . . .
O5A O 0.3369(4) 0.6023(3) 0.8189(2) 0.0563(10) Uani 1 1 d . . . . .
O6A O 0.2055(5) 0.3807(3) 0.6808(2) 0.0710(12) Uani 1 1 d . . . . .
N4A N 0.0886(4) 0.6376(3) 0.5522(2) 0.0357(9) Uani 1 1 d . . . . .
N4 N 0.8247(4) 0.4305(3) 0.7844(2) 0.0333(9) Uani 1 1 d . . . . .
O5 O 0.6801(4) 0.8269(2) 0.6461(2) 0.0500(10) Uani 1 1 d . . . . .
O1 O 0.8659(5) 0.6118(3) 0.8908(2) 0.0650(12) Uani 1 1 d . . . . .
H1B H 0.921560 0.571803 0.922532 0.098 Uiso 1 1 calc R U . . .
C16A C 0.2762(7) 0.9607(6) 0.1418(4) 0.0658(17) Uani 1 1 d . . . . .
H16A H 0.361249 0.984221 0.096130 0.079 Uiso 1 1 calc R U . . .
C15A C 0.2190(7) 1.0277(5) 0.1817(4) 0.0627(16) Uani 1 1 d . . . . .
H15A H 0.264039 1.096268 0.163019 0.075 Uiso 1 1 calc R U . . .
C14A C 0.0925(6) 0.9913(4) 0.2505(3) 0.0473(13) Uani 1 1 d . . . . .
H14A H 0.053232 1.035701 0.278232 0.057 Uiso 1 1 calc R U . . .
C13A C 0.0258(5) 0.8912(4) 0.2776(3) 0.0369(11) Uani 1 1 d . . . . .
C12A C -0.1071(6) 0.8492(4) 0.3535(3) 0.0460(13) Uani 1 1 d . . . . .
H12D H -0.153712 0.907953 0.365947 0.055 Uiso 1 1 calc R U . . .
H12C H -0.186606 0.813041 0.339668 0.055 Uiso 1 1 calc R U . . .
C11A C -0.0028(5) 0.8148(4) 0.4808(3) 0.0350(11) Uani 1 1 d . . . . .
C3A C 0.0677(5) 0.7358(3) 0.5519(3) 0.0327(11) Uani 1 1 d . . . . .
C2A C 0.1137(5) 0.7644(3) 0.6142(3) 0.0378(12) Uani 1 1 d . . . . .
C1A C 0.1798(6) 0.6886(4) 0.6799(3) 0.0408(12) Uani 1 1 d . . . . .
H1A H 0.209253 0.706054 0.722966 0.049 Uiso 1 1 calc R U . . .
C10E C 0.2014(5) 0.5873(3) 0.6811(3) 0.0295(10) Uani 1 1 d . . . . .
C10D C 0.2695(5) 0.4995(3) 0.7459(3) 0.0310(10) Uani 1 1 d . . . . .
C6AA C 0.2684(6) 0.3999(3) 0.7417(3) 0.0400(12) Uani 1 1 d . . . . .
C7A C 0.3251(6) 0.3110(4) 0.8009(3) 0.0496(14) Uani 1 1 d . . . . .
H7A H 0.322316 0.245420 0.796130 0.059 Uiso 1 1 calc R U . . .
C8A C 0.3855(6) 0.3211(4) 0.8667(3) 0.0429(12) Uani 1 1 d . . . . .
C19A C 0.5042(7) 0.2366(4) 0.9913(4) 0.0645(17) Uani 1 1 d . . . . .
H19E H 0.592485 0.287125 0.965979 0.097 Uiso 1 1 calc R U . . .
H19F H 0.537869 0.167860 1.025748 0.097 Uiso 1 1 calc R U . . .
H19D H 0.428536 0.260183 1.027538 0.097 Uiso 1 1 calc R U . . .
C17A C 0.2106(7) 0.8611(5) 0.1681(4) 0.0558(15) Uani 1 1 d . . . . .
H17A H 0.250459 0.816571 0.140594 0.067 Uiso 1 1 calc R U . . .
C18A C 0.0853(6) 0.8260(4) 0.2354(3) 0.0434(12) Uani 1 1 d . . . . .
H18A H 0.039635 0.757818 0.252954 0.052 Uiso 1 1 calc R U . . .
C10C C 0.3338(5) 0.5052(4) 0.8141(3) 0.0377(12) Uani 1 1 d . . . . .
C20A C 0.3916(7) 0.6101(4) 0.8903(4) 0.0654(17) Uani 1 1 d . . . . .
H20D H 0.325027 0.565749 0.943711 0.098 Uiso 1 1 calc R U . . .
H20E H 0.390321 0.683095 0.884589 0.098 Uiso 1 1 calc R U . . .
H20F H 0.496397 0.586832 0.890757 0.098 Uiso 1 1 calc R U . . .
C9A C 0.3906(5) 0.4165(4) 0.8745(3) 0.0422(12) Uani 1 1 d . . . . .
H9A H 0.431355 0.422288 0.919554 0.051 Uiso 1 1 calc R U . . .
C5A C 0.1830(7) 0.4641(4) 0.6067(4) 0.0598(16) Uani 1 1 d . . . . .
H5D H 0.094992 0.444470 0.587009 0.072 Uiso 1 1 calc R U . . .
H5C H 0.274595 0.474023 0.561909 0.072 Uiso 1 1 calc R U . . .
C4AA C 0.1539(5) 0.5678(3) 0.6144(3) 0.0325(11) Uani 1 1 d . . . . .
C19 C 0.3914(6) 0.7747(4) 0.3690(3) 0.0468(13) Uani 1 1 d . . . . .
H19C H 0.476627 0.741223 0.346830 0.070 Uiso 1 1 calc R U . . .
H19B H 0.349838 0.825905 0.321379 0.070 Uiso 1 1 calc R U . . .
H19A H 0.311155 0.721235 0.406397 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5131(5) 0.7684(3) 0.4869(3) 0.0307(11) Uani 1 1 d . . . . .
C7 C 0.5339(5) 0.6609(3) 0.5125(3) 0.0328(11) Uani 1 1 d . . . . .
H7 H 0.500701 0.622226 0.483489 0.039 Uiso 1 1 calc R U . . .
C6A C 0.6067(5) 0.6126(3) 0.5836(3) 0.0298(10) Uani 1 1 d . . . . .
C5 C 0.7384(7) 0.4562(4) 0.6528(4) 0.0559(16) Uani 1 1 d . . . . .
H5B H 0.835266 0.468295 0.611269 0.067 Uiso 1 1 calc R U . . .
H5A H 0.715206 0.379559 0.681426 0.067 Uiso 1 1 calc R U . . .
C4A C 0.7617(5) 0.4971(3) 0.7192(3) 0.0280(10) Uani 1 1 d . . . . .
C3 C 0.8603(5) 0.4666(3) 0.8421(3) 0.0301(10) Uani 1 1 d . . . . .
C11 C 0.9324(5) 0.3934(3) 0.9151(3) 0.0334(11) Uani 1 1 d . . . . .
C12 C 1.0208(6) 0.2195(4) 0.9862(3) 0.0484(13) Uani 1 1 d . . . . .
H12A H 1.085221 0.257895 1.006935 0.058 Uiso 1 1 calc R U . . .
H12B H 1.087532 0.175220 0.963449 0.058 Uiso 1 1 calc R U . . .
C13 C 0.8983(5) 0.1503(4) 1.0600(3) 0.0367(11) Uani 1 1 d . . . . .
C14 C 0.8546(6) 0.1732(4) 1.1322(4) 0.0512(14) Uani 1 1 d . . . . .
H14 H 0.901206 0.231784 1.135623 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7404(7) 0.1085(5) 1.2001(4) 0.0674(17) Uani 1 1 d . . . . .
H15 H 0.711082 0.123769 1.249216 0.081 Uiso 1 1 calc R U . . .
C16 C 0.6716(7) 0.0236(5) 1.1956(4) 0.0631(16) Uani 1 1 d . . . . .
H16 H 0.594298 -0.018783 1.241174 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5601(5) 0.8250(4) 0.5302(3) 0.0379(12) Uani 1 1 d . . . . .
H9 H 0.543540 0.897705 0.512069 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6322(5) 0.7743(3) 0.6009(3) 0.0314(11) Uani 1 1 d . . . . .
C20 C 0.6544(7) 0.9384(3) 0.6194(3) 0.0562(16) Uani 1 1 d . . . . .
H20B H 0.704992 0.975978 0.559952 0.084 Uiso 1 1 calc R U . . .
H20C H 0.696626 0.965358 0.655854 0.084 Uiso 1 1 calc R U . . .
H20A H 0.544220 0.948642 0.624488 0.084 Uiso 1 1 calc R U . . .
C10A C 0.6573(5) 0.6638(3) 0.6301(3) 0.0266(10) Uani 1 1 d . . . . .
C18 C 0.8312(6) 0.0630(4) 1.0561(4) 0.0509(14) Uani 1 1 d . . . . .
H18 H 0.863097 0.045978 1.008062 0.061 Uiso 1 1 calc R U . . .
C17 C 0.7154(7) -0.0004(4) 1.1240(5) 0.0648(17) Uani 1 1 d . . . . .
H17 H 0.667879 -0.058832 1.120758 0.078 Uiso 1 1 calc R U . . .
C2 C 0.8331(5) 0.5703(3) 0.8348(3) 0.0343(11) Uani 1 1 d . . . . .
C1 C 0.7665(5) 0.6382(3) 0.7658(3) 0.0367(12) Uani 1 1 d . . . . .
H1 H 0.746860 0.707792 0.760126 0.044 Uiso 1 1 calc R U . . .
C10B C 0.7294(5) 0.6027(3) 0.7058(3) 0.0272(10) 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
O3A C11A 1.319(5) . ?
O3A C12A 1.460(5) . ?
O2A C11A 1.210(5) . ?
O4 C8 1.369(5) . ?
O4 C19 1.423(5) . ?
O6 C6A 1.385(5) . ?
O6 C5 1.405(5) . ?
O3 C11 1.314(5) . ?
O3 C12 1.476(5) . ?
O2 C11 1.208(5) . ?
O4A C8A 1.372(5) . ?
O4A C19A 1.428(6) . ?
O1A C2A 1.354(5) . ?
O1A H1C 0.8200 . ?
O5A C10C 1.358(5) . ?
O5A C20A 1.421(6) . ?
O6A C6AA 1.365(5) . ?
O6A C5A 1.366(6) . ?
N4A C4AA 1.320(5) . ?
N4A C3A 1.344(5) . ?
N4 C4A 1.324(5) . ?
N4 C3 1.340(5) . ?
O5 C10 1.356(5) . ?
O5 C20 1.428(5) . ?
O1 C2 1.356(5) . ?
O1 H1B 0.8200 . ?
C16A C17A 1.354(8) . ?
C16A C15A 1.375(8) . ?
C16A H16A 0.9300 . ?
C15A C14A 1.391(7) . ?
C15A H15A 0.9300 . ?
C14A C13A 1.361(6) . ?
C14A H14A 0.9300 . ?
C13A C18A 1.387(6) . ?
C13A C12A 1.499(7) . ?
C12A H12D 0.9700 . ?
C12A H12C 0.9700 . ?
C11A C3A 1.485(6) . ?
C3A C2A 1.384(6) . ?
C2A C1A 1.392(6) . ?
C1A C10E 1.382(6) . ?
C1A H1A 0.9300 . ?
C10E C4AA 1.391(6) . ?
C10E C10D 1.469(6) . ?
C10D C6AA 1.386(6) . ?
C10D C10C 1.403(6) . ?
C6AA C7A 1.383(6) . ?
C7A C8A 1.371(7) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.360(6) . ?
C19A H19E 0.9600 . ?
C19A H19F 0.9600 . ?
C19A H19D 0.9600 . ?
C17A C18A 1.369(7) . ?
C17A H17A 0.9300 . ?
C18A H18A 0.9300 . ?
C10C C9A 1.391(6) . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C9A H9A 0.9300 . ?
C5A C4AA 1.483(6) . ?
C5A H5D 0.9700 . ?
C5A H5C 0.9700 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C8 C9 1.369(6) . ?
C8 C7 1.371(6) . ?
C7 C6A 1.387(6) . ?
C7 H7 0.9300 . ?
C6A C10A 1.371(5) . ?
C5 C4A 1.486(6) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C4A C10B 1.396(5) . ?
C3 C2 1.388(6) . ?
C3 C11 1.484(6) . ?
C12 C13 1.496(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.366(7) . ?
C13 C14 1.371(7) . ?
C14 C15 1.388(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.349(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(8) . ?
C16 H16 0.9300 . ?
C9 C10 1.381(6) . ?
C9 H9 0.9300 . ?
C10 C10A 1.413(6) . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20A 0.9600 . ?
C10A C10B 1.471(6) . ?
C18 C17 1.390(8) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C2 C1 1.389(6) . ?
C1 C10B 1.375(6) . ?
C1 H1 0.9300 . ?

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
C11A O3A C12A 116.8(4) . . ?
C8 O4 C19 118.7(3) . . ?
C6A O6 C5 116.6(3) . . ?
C11 O3 C12 116.8(4) . . ?
C8A O4A C19A 116.7(4) . . ?
C2A O1A H1C 109.5 . . ?
C10C O5A C20A 118.4(4) . . ?
C6AA O6A C5A 119.8(4) . . ?
C4AA N4A C3A 118.1(4) . . ?
C4A N4 C3 118.0(4) . . ?
C10 O5 C20 118.5(3) . . ?
C2 O1 H1B 109.5 . . ?
C17A C16A C15A 121.0(6) . . ?
C17A C16A H16A 119.5 . . ?
C15A C16A H16A 119.5 . . ?
C16A C15A C14A 118.9(5) . . ?
C16A C15A H15A 120.5 . . ?
C14A C15A H15A 120.5 . . ?
C13A C14A C15A 120.6(5) . . ?
C13A C14A H14A 119.7 . . ?
C15A C14A H14A 119.7 . . ?
C14A C13A C18A 119.0(5) . . ?
C14A C13A C12A 121.4(5) . . ?
C18A C13A C12A 119.5(4) . . ?
O3A C12A C13A 109.3(4) . . ?
O3A C12A H12D 109.8 . . ?
C13A C12A H12D 109.8 . . ?
O3A C12A H12C 109.8 . . ?
C13A C12A H12C 109.8 . . ?
H12D C12A H12C 108.3 . . ?
O2A C11A O3A 124.6(4) . . ?
O2A C11A C3A 121.9(4) . . ?
O3A C11A C3A 113.5(4) . . ?
N4A C3A C2A 121.7(4) . . ?
N4A C3A C11A 117.9(4) . . ?
C2A C3A C11A 120.4(4) . . ?
O1A C2A C3A 124.4(4) . . ?
O1A C2A C1A 116.5(4) . . ?
C3A C2A C1A 119.0(4) . . ?
C10E C1A C2A 119.8(4) . . ?
C10E C1A H1A 120.1 . . ?
C2A C1A H1A 120.1 . . ?
C1A C10E C4AA 116.4(4) . . ?
C1A C10E C10D 125.9(4) . . ?
C4AA C10E C10D 117.7(4) . . ?
C6AA C10D C10C 115.7(4) . . ?
C6AA C10D C10E 118.0(4) . . ?
C10C C10D C10E 126.3(4) . . ?
O6A C6AA C7A 114.4(4) . . ?
O6A C6AA C10D 122.7(4) . . ?
C7A C6AA C10D 122.8(4) . . ?
C8A C7A C6AA 119.0(4) . . ?
C8A C7A H7A 120.5 . . ?
C6AA C7A H7A 120.5 . . ?
C9A C8A C7A 121.3(4) . . ?
C9A C8A O4A 123.6(5) . . ?
C7A C8A O4A 115.1(4) . . ?
O4A C19A H19E 109.5 . . ?
O4A C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
O4A C19A H19D 109.5 . . ?
H19E C19A H19D 109.5 . . ?
H19F C19A H19D 109.5 . . ?
C16A C17A C18A 119.8(5) . . ?
C16A C17A H17A 120.1 . . ?
C18A C17A H17A 120.1 . . ?
C17A C18A C13A 120.6(5) . . ?
C17A C18A H18A 119.7 . . ?
C13A C18A H18A 119.7 . . ?
O5A C10C C9A 121.2(4) . . ?
O5A C10C C10D 116.5(4) . . ?
C9A C10C C10D 122.2(4) . . ?
O5A C20A H20D 109.5 . . ?
O5A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
O5A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C8A C9A C10C 119.0(4) . . ?
C8A C9A H9A 120.5 . . ?
C10C C9A H9A 120.5 . . ?
O6A C5A C4AA 115.9(4) . . ?
O6A C5A H5D 108.3 . . ?
C4AA C5A H5D 108.3 . . ?
O6A C5A H5C 108.3 . . ?
C4AA C5A H5C 108.3 . . ?
H5D C5A H5C 107.4 . . ?
N4A C4AA C10E 125.0(4) . . ?
N4A C4AA C5A 114.8(4) . . ?
C10E C4AA C5A 120.2(4) . . ?
O4 C19 H19C 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
O4 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
O4 C8 C9 114.9(4) . . ?
O4 C8 C7 123.5(4) . . ?
C9 C8 C7 121.7(4) . . ?
C8 C7 C6A 116.7(4) . . ?
C8 C7 H7 121.6 . . ?
C6A C7 H7 121.6 . . ?
C10A C6A O6 121.6(4) . . ?
C10A C6A C7 125.0(4) . . ?
O6 C6A C7 113.3(3) . . ?
O6 C5 C4A 114.3(4) . . ?
O6 C5 H5B 108.7 . . ?
C4A C5 H5B 108.7 . . ?
O6 C5 H5A 108.7 . . ?
C4A C5 H5A 108.7 . . ?
H5B C5 H5A 107.6 . . ?
N4 C4A C10B 124.8(4) . . ?
N4 C4A C5 115.6(4) . . ?
C10B C4A C5 119.4(4) . . ?
N4 C3 C2 121.8(4) . . ?
N4 C3 C11 118.7(4) . . ?
C2 C3 C11 119.5(4) . . ?
O2 C11 O3 124.0(4) . . ?
O2 C11 C3 122.5(4) . . ?
O3 C11 C3 113.5(4) . . ?
O3 C12 C13 110.3(4) . . ?
O3 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
O3 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C18 C13 C14 119.8(5) . . ?
C18 C13 C12 119.9(5) . . ?
C14 C13 C12 120.3(5) . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.1(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
O5 C10 C9 122.2(4) . . ?
O5 C10 C10A 116.9(4) . . ?
C9 C10 C10A 120.9(4) . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
C6A C10A C10 115.6(4) . . ?
C6A C10A C10B 119.7(4) . . ?
C10 C10A C10B 124.7(3) . . ?
C13 C18 C17 120.0(5) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C16 C17 C18 119.8(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O1 C2 C3 124.8(4) . . ?
O1 C2 C1 116.3(4) . . ?
C3 C2 C1 118.9(4) . . ?
C10B C1 C2 120.2(4) . . ?
C10B C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C10B C4A 116.4(4) . . ?
C1 C10B C10A 126.8(4) . . ?
C4A C10B C10A 116.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17A C16A C15A C14A 0.5(9) . . . . ?
C16A C15A C14A C13A -0.4(8) . . . . ?
C15A C14A C13A C18A -0.3(7) . . . . ?
C15A C14A C13A C12A 177.9(4) . . . . ?
C11A O3A C12A C13A 91.0(5) . . . . ?
C14A C13A C12A O3A -103.4(5) . . . . ?
C18A C13A C12A O3A 74.8(5) . . . . ?
C12A O3A C11A O2A 4.7(7) . . . . ?
C12A O3A C11A C3A -174.8(4) . . . . ?
C4AA N4A C3A C2A 0.5(7) . . . . ?
C4AA N4A C3A C11A 178.8(4) . . . . ?
O2A C11A C3A N4A -174.2(4) . . . . ?
O3A C11A C3A N4A 5.3(6) . . . . ?
O2A C11A C3A C2A 4.1(7) . . . . ?
O3A C11A C3A C2A -176.3(4) . . . . ?
N4A C3A C2A O1A 178.6(5) . . . . ?
C11A C3A C2A O1A 0.3(7) . . . . ?
N4A C3A C2A C1A -1.6(7) . . . . ?
C11A C3A C2A C1A -179.9(4) . . . . ?
O1A C2A C1A C10E -178.8(4) . . . . ?
C3A C2A C1A C10E 1.3(7) . . . . ?
C2A C1A C10E C4AA -0.1(7) . . . . ?
C2A C1A C10E C10D 179.9(4) . . . . ?
C1A C10E C10D C6AA 173.9(5) . . . . ?
C4AA C10E C10D C6AA -6.1(6) . . . . ?
C1A C10E C10D C10C -4.6(7) . . . . ?
C4AA C10E C10D C10C 175.4(4) . . . . ?
C5A O6A C6AA C7A -163.0(5) . . . . ?
C5A O6A C6AA C10D 19.5(8) . . . . ?
C10C C10D C6AA O6A 177.9(4) . . . . ?
C10E C10D C6AA O6A -0.8(7) . . . . ?
C10C C10D C6AA C7A 0.6(7) . . . . ?
C10E C10D C6AA C7A -178.0(5) . . . . ?
O6A C6AA C7A C8A -177.6(5) . . . . ?
C10D C6AA C7A C8A -0.1(8) . . . . ?
C6AA C7A C8A C9A -0.1(8) . . . . ?
C6AA C7A C8A O4A 178.5(4) . . . . ?
C19A O4A C8A C9A -3.7(7) . . . . ?
C19A O4A C8A C7A 177.9(5) . . . . ?
C15A C16A C17A C18A 0.0(8) . . . . ?
C16A C17A C18A C13A -0.7(8) . . . . ?
C14A C13A C18A C17A 0.8(7) . . . . ?
C12A C13A C18A C17A -177.4(4) . . . . ?
C20A O5A C10C C9A -3.5(7) . . . . ?
C20A O5A C10C C10D 175.9(4) . . . . ?
C6AA C10D C10C O5A 179.6(4) . . . . ?
C10E C10D C10C O5A -1.9(7) . . . . ?
C6AA C10D C10C C9A -1.0(7) . . . . ?
C10E C10D C10C C9A 177.5(4) . . . . ?
C7A C8A C9A C10C -0.3(8) . . . . ?
O4A C8A C9A C10C -178.7(4) . . . . ?
O5A C10C C9A C8A -179.7(4) . . . . ?
C10D C10C C9A C8A 0.9(7) . . . . ?
C6AA O6A C5A C4AA -29.1(8) . . . . ?
C3A N4A C4AA C10E 0.9(7) . . . . ?
C3A N4A C4AA C5A -175.9(4) . . . . ?
C1A C10E C4AA N4A -1.1(7) . . . . ?
C10D C10E C4AA N4A 178.9(4) . . . . ?
C1A C10E C4AA C5A 175.5(5) . . . . ?
C10D C10E C4AA C5A -4.5(7) . . . . ?
O6A C5A C4AA N4A -161.1(5) . . . . ?
O6A C5A C4AA C10E 21.9(8) . . . . ?
C19 O4 C8 C9 -179.1(4) . . . . ?
C19 O4 C8 C7 1.3(6) . . . . ?
O4 C8 C7 C6A 178.8(4) . . . . ?
C9 C8 C7 C6A -0.9(7) . . . . ?
C5 O6 C6A C10A -27.2(6) . . . . ?
C5 O6 C6A C7 155.6(4) . . . . ?
C8 C7 C6A C10A 0.7(7) . . . . ?
C8 C7 C6A O6 177.7(4) . . . . ?
C6A O6 C5 C4A 40.5(6) . . . . ?
C3 N4 C4A C10B 0.1(6) . . . . ?
C3 N4 C4A C5 174.6(4) . . . . ?
O6 C5 C4A N4 154.5(4) . . . . ?
O6 C5 C4A C10B -30.7(7) . . . . ?
C4A N4 C3 C2 -0.1(6) . . . . ?
C4A N4 C3 C11 -179.4(4) . . . . ?
C12 O3 C11 O2 -1.4(7) . . . . ?
C12 O3 C11 C3 179.0(4) . . . . ?
N4 C3 C11 O2 177.7(4) . . . . ?
C2 C3 C11 O2 -1.6(7) . . . . ?
N4 C3 C11 O3 -2.7(6) . . . . ?
C2 C3 C11 O3 178.0(4) . . . . ?
C11 O3 C12 C13 97.4(5) . . . . ?
O3 C12 C13 C18 82.5(5) . . . . ?
O3 C12 C13 C14 -98.5(5) . . . . ?
C18 C13 C14 C15 -1.2(7) . . . . ?
C12 C13 C14 C15 179.8(4) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
C14 C15 C16 C17 0.8(9) . . . . ?
O4 C8 C9 C10 -178.8(4) . . . . ?
C7 C8 C9 C10 0.8(7) . . . . ?
C20 O5 C10 C9 0.2(7) . . . . ?
C20 O5 C10 C10A -179.0(4) . . . . ?
C8 C9 C10 O5 -179.7(4) . . . . ?
C8 C9 C10 C10A -0.6(7) . . . . ?
O6 C6A C10A C10 -177.3(4) . . . . ?
C7 C6A C10A C10 -0.5(7) . . . . ?
O6 C6A C10A C10B 1.6(6) . . . . ?
C7 C6A C10A C10B 178.4(4) . . . . ?
O5 C10 C10A C6A 179.5(4) . . . . ?
C9 C10 C10A C6A 0.4(6) . . . . ?
O5 C10 C10A C10B 0.7(6) . . . . ?
C9 C10 C10A C10B -178.4(4) . . . . ?
C14 C13 C18 C17 2.1(7) . . . . ?
C12 C13 C18 C17 -178.9(4) . . . . ?
C15 C16 C17 C18 0.1(8) . . . . ?
C13 C18 C17 C16 -1.6(7) . . . . ?
N4 C3 C2 O1 179.9(4) . . . . ?
C11 C3 C2 O1 -0.9(7) . . . . ?
N4 C3 C2 C1 0.3(7) . . . . ?
C11 C3 C2 C1 179.6(4) . . . . ?
O1 C2 C1 C10B 180.0(4) . . . . ?
C3 C2 C1 C10B -0.4(7) . . . . ?
C2 C1 C10B C4A 0.3(7) . . . . ?
C2 C1 C10B C10A 179.3(4) . . . . ?
N4 C4A C10B C1 -0.2(7) . . . . ?
C5 C4A C10B C1 -174.5(4) . . . . ?
N4 C4A C10B C10A -179.3(4) . . . . ?
C5 C4A C10B C10A 6.4(6) . . . . ?
C6A C10A C10B C1 -170.5(4) . . . . ?
C10 C10A C10B C1 8.3(7) . . . . ?
C6A C10A C10B C4A 8.5(6) . . . . ?
C10 C10A C10B C4A -172.7(4) . . . . ?

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
_geom_hbond_publ_flag
O1A H1C O2A 0.82 1.94 2.647(5) 143.2 . yes
O1A H1C O2A 0.82 2.45 3.038(4) 129.2 2_576 yes
O1 H1B O2 0.82 1.96 2.640(5) 140.0 . yes
O1 H1B O2 0.82 2.25 2.875(4) 132.9 2_767 yes
C1A H1A O5A 0.93 2.16 2.780(5) 123.4 . yes
C1 H1 O5 0.93 2.15 2.766(5) 123.0 . yes
O1A H1C O2A 0.82 1.94 2.647(5) 143.2 . yes
O1A H1C O2A 0.82 2.45 3.038(4) 129.2 2_576 yes
O1 H1B O2 0.82 1.96 2.640(5) 140.0 . yes
O1 H1B O2 0.82 2.25 2.875(4) 132.9 2_767 yes
C1A H1A O5A 0.93 2.16 2.780(5) 123.4 . yes
C1 H1 O5 0.93 2.15 2.766(5) 123.0 . yes

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.060





# start Validation Reply Form
_vrf_RINTA01_4                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal size, poorer quality and diffracting power
gave rise to low quality data. Nevertheless, the structure refined to
convergence and all results were consistent with the model in this report.
;
_vrf_PLAT020_4                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.219 Report
RESPONSE: The crystal size, poorer quality and diffracting power
gave rise to low quality data. Nevertheless, the structure refined to
convergence and all results were consistent with the model in this report.
;
# end Validation Reply Form
