# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_I
_chemical_name_systematic        (R)-N-(1-Phenylethyl)-2-chromonecarboxamide
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         293.31
_chemical_absolute_configuration syn

_chemical_melting_point          396-397

_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   13.4156(6)
_cell_length_b                   13.4156(6)
_cell_length_c                   28.8130(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4491.0(5)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    9669
_cell_measurement_theta_min      3.8046
_cell_measurement_theta_max      66.7371
_cell_measurement_temperature    173
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848

_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.87

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5285
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         66.73
_diffrn_reflns_theta_full        66.73
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       34

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             5285
_reflns_number_gt                5272
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1164
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.001
_refine_ls_number_reflns         5285
_refine_ls_number_parameters     798
_refine_ls_number_restraints     229
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1113P)²+0.1316P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'SHELXT(George Sheldrick, 2012)'
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'No quotients, so Flack parameter determined by classical intensity fit'
_refine_ls_abs_structure_Flack   0.22(18)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.5095(3) 0.7791(3) 0.18239(12) 0.0327(7) Uani d U . . 1 . .
C C2 0.4108(3) 0.6810(3) 0.18990(13) 0.0361(7) Uani d U . . 1 . .
H H2 0.3542 0.6502 0.1662 0.043 Uiso calc U . R 1 . .
C C3 0.3893(3) 0.6210(3) 0.23390(13) 0.0346(7) Uani d U . . 1 . .
C C4 0.4814(3) 0.6803(3) 0.26854(12) 0.0329(7) Uani d U . . 1 . .
C C5 0.4706(4) 0.6370(3) 0.31363(13) 0.0391(8) Uani d U . . 1 . .
H H5 0.4031 0.5679 0.3223 0.047 Uiso calc U . R 1 . .
C C6 0.5580(4) 0.6947(4) 0.34540(14) 0.0451(9) Uani d U . . 1 . .
H H6 0.5505 0.6661 0.3761 0.054 Uiso calc U . R 1 . .
C C7 0.6580(4) 0.7959(4) 0.33210(15) 0.0440(9) Uani d U . . 1 . .
H H7 0.719 0.8341 0.3538 0.053 Uiso calc U . R 1 . .
C C8 0.6694(3) 0.8409(3) 0.28821(14) 0.0384(7) Uani d U . . 1 . .
H H8 0.7365 0.9107 0.2798 0.046 Uiso calc U . R 1 . .
C C9 0.5809(3) 0.7822(3) 0.25641(13) 0.0317(7) Uani d U . . 1 . .
C C10 0.5306(3) 0.8482(4) 0.13783(13) 0.0405(8) Uani d U . . 1 . .
C C11 0.6321(4) 1.0389(4) 0.10322(16) 0.0521(11) Uani d U . . 1 . .
H H11 0.608 0.9943 0.0736 0.062 Uiso calc U . R 1 . .
C C12 0.5545(5) 1.0893(6) 0.1106(3) 0.0792(19) Uani d U . . 1 . .
H H12A 0.4742 1.027 0.1117 0.119 Uiso calc U . R 1 . .
H H12B 0.5645 1.1414 0.0849 0.119 Uiso calc U . R 1 . .
H H12C 0.5746 1.1321 0.1399 0.119 Uiso calc U . R 1 . .
C C13 0.7593(4) 1.1261(4) 0.09914(12) 0.0453(10) Uani d U . . 1 . .
C C14 0.8352(5) 1.0874(4) 0.08876(15) 0.0541(11) Uani d U . . 1 . .
H H14 0.8058 1.0074 0.0839 0.065 Uiso calc U . R 1 . .
C C15 0.9526(6) 1.1619(6) 0.08533(19) 0.0693(14) Uani d U . . 1 . .
H H15 1.003 1.1331 0.079 0.083 Uiso calc U . R 1 . .
C C16 0.9959(5) 1.2791(6) 0.0913(2) 0.0734(16) Uani d U . . 1 . .
H H16 1.0761 1.3316 0.0884 0.088 Uiso calc U . R 1 . .
C C17 0.9222(6) 1.3178(5) 0.10130(19) 0.0683(15) Uani d U . . 1 . .
H H17 0.9521 1.3981 0.1055 0.082 Uiso calc U . R 1 . .
C C18 0.8046(5) 1.2439(4) 0.10562(17) 0.0585(12) Uani d U . . 1 . .
H H18 0.7552 1.2734 0.113 0.07 Uiso calc U . R 1 . .
C C19 0.6494(3) 0.5067(3) 0.02563(11) 0.0335(7) Uani d U . . 1 . .
C C20 0.7637(4) 0.5519(4) 0.02807(13) 0.0389(8) Uani d U . . 1 . .
H H20 0.7938 0.503 0.0354 0.047 Uiso calc U . R 1 . .
C C21 0.8421(3) 0.6719(4) 0.01993(12) 0.0369(8) Uani d U . . 1 . .
C C22 0.7867(3) 0.7393(3) 0.00820(11) 0.0319(7) Uani d U . . 1 . .
C C23 0.8507(3) 0.8567(4) -0.00163(12) 0.0391(8) Uani d U . . 1 . .
H H23 0.9324 0.895 -0.0011 0.047 Uiso calc U . R 1 . .
C C24 0.7953(4) 0.9170(4) -0.01215(14) 0.0436(8) Uani d U . . 1 . .
H H24 0.8391 0.9969 -0.0189 0.052 Uiso calc U . R 1 . .
C C25 0.6750(4) 0.8610(4) -0.01288(16) 0.0485(10) Uani d U . . 1 . .
H H25 0.6376 0.9034 -0.0199 0.058 Uiso calc U . R 1 . .
C C26 0.6104(3) 0.7451(4) -0.00351(16) 0.0435(9) Uani d U . . 1 . .
H H26 0.5287 0.707 -0.0044 0.052 Uiso calc U . R 1 . .
C C27 0.6665(3) 0.6851(3) 0.00729(11) 0.0309(7) Uani d U . . 1 . .
C C28 0.5666(4) 0.3805(3) 0.03238(13) 0.0377(8) Uani d U . . 1 . .
C C29 0.3742(4) 0.2183(3) 0.02532(13) 0.0389(8) Uani d U . . 1 . .
H H29 0.4181 0.1804 0.0146 0.047 Uiso calc U . R 1 . .
C C30 0.3310(5) 0.1737(4) 0.07376(15) 0.0603(13) Uani d U . . 1 . .
H H30A 0.3967 0.1966 0.0946 0.091 Uiso calc U . R 1 . .
H H30B 0.2841 0.0896 0.073 0.091 Uiso calc U . R 1 . .
H H30C 0.2842 0.2061 0.085 0.091 Uiso calc U . R 1 . .
C C31 0.2780(4) 0.1864(3) -0.00926(13) 0.0423(8) Uani d U . . 1 . .
C C32 0.1941(5) 0.2155(5) -0.0017(2) 0.0609(12) Uani d U . . 1 . .
H H32 0.1988 0.2596 0.0248 0.073 Uiso calc U . R 1 . .
C C33 0.1042(6) 0.1818(6) -0.0321(3) 0.095(2) Uani d U . . 1 . .
H H33 0.0462 0.2011 -0.0263 0.114 Uiso calc U . R 1 . .
C C34 0.0983(7) 0.1180(6) -0.0722(3) 0.103(3) Uani d U . . 1 . .
H H34 0.0367 0.0946 -0.0936 0.124 Uiso calc U . R 1 . .
C C35 0.1829(8) 0.0904(5) -0.0798(2) 0.092(2) Uani d U . . 1 . .
H H35 0.1802 0.0486 -0.1068 0.111 Uiso calc U . R 1 . .
C C36 0.2719(5) 0.1230(4) -0.04836(16) 0.0606(13) Uani d U . . 1 . .
H H36 0.3289 0.102 -0.0535 0.073 Uiso calc U . R 1 . .
C C37 0.1615(3) 0.5999(3) 0.06779(13) 0.0330(7) Uani d U . . 1 . .
C C38 0.2453(3) 0.5733(3) 0.06746(13) 0.0388(7) Uani d U . . 1 . .
H H38 0.2924 0.5887 0.0942 0.047 Uiso calc U . R 1 . .
C C39 0.2655(3) 0.5210(3) 0.02687(15) 0.0403(8) Uani d U . . 1 . .
C C40 0.1925(3) 0.5086(3) -0.01321(14) 0.0354(7) Uani d U . . 1 . .
C C41 0.2062(4) 0.4695(4) -0.05607(15) 0.0467(9) Uani d U . . 1 . .
H H41 0.264 0.4489 -0.0599 0.056 Uiso calc U . R 1 . .
C C42 0.1372(5) 0.4602(4) -0.09297(15) 0.0532(11) Uani d U . . 1 . .
H H42 0.1478 0.434 -0.1222 0.064 Uiso calc U . R 1 . .
C C43 0.0519(5) 0.4890(4) -0.08747(14) 0.0491(10) Uani d U . . 1 . .
H H43 0.0035 0.4811 -0.1129 0.059 Uiso calc U . R 1 . .
C C44 0.0365(4) 0.5287(3) -0.04576(13) 0.0391(8) Uani d U . . 1 . .
H H44 -0.0215 0.5489 -0.0422 0.047 Uiso calc U . R 1 . .
C C45 0.1073(3) 0.5386(3) -0.00896(12) 0.0329(7) Uani d U . . 1 . .
C C46 0.1400(3) 0.6569(3) 0.10858(12) 0.0353(7) Uani d U . . 1 . .
C C47 0.0465(3) 0.7611(4) 0.13642(13) 0.0394(8) Uani d U . . 1 . .
H H47 0.0631 0.7385 0.1673 0.047 Uiso calc U . R 1 . .
C C48 0.1308(4) 0.8887(4) 0.13027(17) 0.0522(10) Uani d U . . 1 . .
H H48A 0.2097 0.9029 0.1329 0.078 Uiso calc U . R 1 . .
H H48B 0.1172 0.9322 0.1543 0.078 Uiso calc U . R 1 . .
H H48C 0.1199 0.9133 0.0996 0.078 Uiso calc U . R 1 . .
C C49 -0.0800(3) 0.7276(4) 0.13661(12) 0.0392(8) Uani d U . . 1 . .
C C50 -0.1619(4) 0.6142(4) 0.14511(14) 0.0440(8) Uani d U . . 1 . .
H H50 -0.1382 0.5589 0.1495 0.053 Uiso calc U . R 1 . .
C C51 -0.2774(5) 0.5799(5) 0.1473(2) 0.0594(11) Uani d U . . 1 . .
H H51 -0.3323 0.5022 0.1544 0.071 Uiso calc U . R 1 . .
C C52 -0.3134(5) 0.6590(6) 0.1392(2) 0.0623(13) Uani d U . . 1 . .
H H52 -0.3929 0.6356 0.1399 0.075 Uiso calc U . R 1 . .
C C53 -0.2327(5) 0.7712(6) 0.1302(2) 0.0631(13) Uani d U . . 1 . .
H H53 -0.2572 0.8254 0.1246 0.076 Uiso calc U . R 1 . .
C C54 -0.1162(4) 0.8075(5) 0.12918(16) 0.0502(10) Uani d U . . 1 . .
H H54 -0.0614 0.886 0.1234 0.06 Uiso calc U . R 1 . .
C C55 0.0151(3) 0.2315(3) 0.20657(12) 0.0344(7) Uani d U . . 1 . .
C C56 -0.0957(4) 0.1464(3) 0.20988(12) 0.0366(8) Uani d U . . 1 . .
H H56 -0.1149 0.0687 0.205 0.044 Uiso calc U . R 1 . .
C C57 -0.1846(3) 0.1724(3) 0.22077(12) 0.0357(7) Uani d U . . 1 . .
C C58 -0.1452(3) 0.2947(3) 0.22923(11) 0.0343(7) Uani d U . . 1 . .
C C59 -0.2206(3) 0.3349(4) 0.23999(12) 0.0403(8) Uani d U . . 1 . .
H H59 -0.3007 0.2818 0.2429 0.048 Uiso calc U . R 1 . .
C C60 -0.1801(4) 0.4503(4) 0.24644(14) 0.0449(9) Uani d U . . 1 . .
H H60 -0.2318 0.4767 0.2543 0.054 Uiso calc U . R 1 . .
C C61 -0.0628(4) 0.5287(4) 0.24150(14) 0.0453(9) Uani d U . . 1 . .
H H61 -0.0356 0.6085 0.2455 0.054 Uiso calc U . R 1 . .
C C62 0.0138(4) 0.4929(4) 0.23096(15) 0.0420(8) Uani d U . . 1 . .
H H62 0.0937 0.5466 0.2281 0.05 Uiso calc U . R 1 . .
C C63 -0.0287(3) 0.3751(3) 0.22449(12) 0.0336(7) Uani d U . . 1 . .
C C64 0.1120(3) 0.2106(3) 0.19425(12) 0.0375(8) Uani d U . . 1 . .
C C65 0.3209(3) 0.2987(4) 0.18442(14) 0.0416(8) Uani d U . . 1 . .
H H65 0.2962 0.226 0.1667 0.05 Uiso calc U . R 1 . .
C C66 0.3945(4) 0.3980(4) 0.15217(17) 0.0539(11) Uani d U . . 1 . .
H H66A 0.3476 0.3978 0.126 0.081 Uiso calc U . R 1 . .
H H66B 0.4585 0.3896 0.1405 0.081 Uiso calc U . R 1 . .
H H66C 0.4249 0.4708 0.1691 0.081 Uiso calc U . R 1 . .
C C67 0.3803(3) 0.2921(4) 0.22810(15) 0.0423(8) Uani d U . . 1 . .
C C68 0.4638(4) 0.3902(5) 0.2508(2) 0.0586(12) Uani d U . . 1 . .
H H68 0.487 0.4639 0.2381 0.07 Uiso calc U . R 1 . .
C C69 0.5134(5) 0.3820(6) 0.2916(2) 0.0696(14) Uani d U . . 1 . .
H H69 0.5704 0.4497 0.3066 0.084 Uiso calc U . R 1 . .
C C70 0.4795(6) 0.2734(7) 0.3108(2) 0.0713(15) Uani d U . . 1 . .
H H70 0.5134 0.2671 0.3388 0.086 Uiso calc U . R 1 . .
C C71 0.3974(6) 0.1770(6) 0.2888(2) 0.0668(13) Uani d U . . 1 . .
H H71 0.3737 0.1032 0.3016 0.08 Uiso calc U . R 1 . .
C C72 0.3477(5) 0.1862(5) 0.24737(18) 0.0561(11) Uani d U . . 1 . .
H H72 0.2909 0.1184 0.2324 0.067 Uiso calc U . R 1 . .
N N1 0.6140(3) 0.9571(3) 0.14077(11) 0.0386(7) Uani d U . . 1 . .
H H1 0.6589 0.9806 0.1654 0.046 Uiso calc U . R 1 . .
N N2 0.4552(3) 0.3428(3) 0.02523(11) 0.0366(6) Uani d U . . 1 . .
H H2A 0.4306 0.3917 0.0205 0.044 Uiso calc U . R 1 . .
N N3 0.0663(3) 0.6943(3) 0.10137(11) 0.0358(6) Uani d U . . 1 . .
H H3 0.0287 0.6785 0.0749 0.043 Uiso calc U . R 1 . .
N N4 0.2164(3) 0.3026(3) 0.19625(11) 0.0378(6) Uani d U . . 1 . .
H H4 0.2234 0.3686 0.205 0.045 Uiso calc U . R 1 . .
O O1 0.5961(2) 0.8302(2) 0.21336(8) 0.0334(5) Uani d U . . 1 . .
O O2 0.3017(3) 0.5290(3) 0.24186(11) 0.0470(7) Uani d U . . 1 . .
O O3 0.4709(4) 0.8017(3) 0.10406(11) 0.0661(11) Uani d U . . 1 . .
O O4 0.5983(2) 0.5694(2) 0.01589(9) 0.0368(5) Uani d U . . 1 . .
O O5 0.9472(2) 0.7164(3) 0.02230(11) 0.0474(7) Uani d U . . 1 . .
O O6 0.6061(3) 0.3183(3) 0.04269(12) 0.0527(7) Uani d U . . 1 . .
O O7 0.0897(2) 0.5812(2) 0.03160(9) 0.0336(5) Uani d U . . 1 . .
O O8 0.3381(3) 0.4908(3) 0.02621(13) 0.0553(8) Uani d U . . 1 . .
O O9 0.1913(3) 0.6679(4) 0.14513(11) 0.0542(8) Uani d U . . 1 . .
O O10 0.0506(2) 0.3436(2) 0.21364(9) 0.0377(6) Uani d U . . 1 . .
O O11 -0.2880(2) 0.0983(3) 0.22256(11) 0.0474(7) Uani d U . . 1 . .
O O12 0.0906(3) 0.1137(3) 0.18275(12) 0.0488(7) Uani d U . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.338(5) ?
C1 O1 . 1.349(4) ?
C1 C10 . 1.525(5) ?
C2 C3 . 1.451(5) ?
C2 H2 . 0.95 ?
C3 O2 . 1.227(5) ?
C3 C4 . 1.474(5) ?
C4 C9 . 1.396(5) ?
C4 C5 . 1.401(5) ?
C5 C6 . 1.380(6) ?
C5 H5 . 0.95 ?
C6 C7 . 1.403(7) ?
C6 H6 . 0.95 ?
C7 C8 . 1.376(6) ?
C7 H7 . 0.95 ?
C8 C9 . 1.391(5) ?
C8 H8 . 0.95 ?
C9 O1 . 1.365(5) ?
C10 O3 . 1.216(5) ?
C10 N1 . 1.326(5) ?
C11 N1 . 1.472(5) ?
C11 C12 . 1.513(9) ?
C11 C13 . 1.516(6) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.388(8) ?
C13 C18 . 1.393(7) ?
C14 C15 . 1.383(8) ?
C14 H14 . 0.95 ?
C15 C16 . 1.387(10) ?
C15 H15 . 0.95 ?
C16 C17 . 1.359(11) ?
C16 H16 . 0.95 ?
C17 C18 . 1.386(9) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 C20 . 1.340(6) ?
C19 O4 . 1.355(4) ?
C19 C28 . 1.502(6) ?
C20 C21 . 1.436(6) ?
C20 H20 . 0.95 ?
C21 O5 . 1.227(5) ?
C21 C22 . 1.468(5) ?
C22 C23 . 1.395(6) ?
C22 C27 . 1.399(5) ?
C23 C24 . 1.378(6) ?
C23 H23 . 0.95 ?
C24 C25 . 1.399(6) ?
C24 H24 . 0.95 ?
C25 C26 . 1.376(6) ?
C25 H25 . 0.95 ?
C26 C27 . 1.384(5) ?
C26 H26 . 0.95 ?
C27 O4 . 1.374(4) ?
C28 O6 . 1.227(5) ?
C28 N2 . 1.333(5) ?
C29 N2 . 1.468(5) ?
C29 C31 . 1.513(6) ?
C29 C30 . 1.515(6) ?
C29 H29 . 1.0 ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
C31 C32 . 1.380(8) ?
C31 C36 . 1.389(7) ?
C32 C33 . 1.372(9) ?
C32 H32 . 0.95 ?
C33 C34 . 1.414(15) ?
C33 H33 . 0.95 ?
C34 C35 . 1.377(15) ?
C34 H34 . 0.95 ?
C35 C36 . 1.383(10) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C37 C38 . 1.339(5) ?
C37 O7 . 1.356(4) ?
C37 C46 . 1.507(5) ?
C38 C39 . 1.457(6) ?
C38 H38 . 0.95 ?
C39 O8 . 1.228(5) ?
C39 C40 . 1.469(6) ?
C40 C41 . 1.390(6) ?
C40 C45 . 1.393(5) ?
C41 C42 . 1.374(7) ?
C41 H41 . 0.95 ?
C42 C43 . 1.388(8) ?
C42 H42 . 0.95 ?
C43 C44 . 1.371(6) ?
C43 H43 . 0.95 ?
C44 C45 . 1.385(5) ?
C44 H44 . 0.95 ?
C45 O7 . 1.372(4) ?
C46 O9 . 1.226(5) ?
C46 N3 . 1.329(5) ?
C47 N3 . 1.460(5) ?
C47 C48 . 1.518(6) ?
C47 C49 . 1.523(6) ?
C47 H47 . 1.0 ?
C48 H48A . 0.98 ?
C48 H48B . 0.98 ?
C48 H48C . 0.98 ?
C49 C50 . 1.382(6) ?
C49 C54 . 1.396(6) ?
C50 C51 . 1.380(7) ?
C50 H50 . 0.95 ?
C51 C52 . 1.388(8) ?
C51 H51 . 0.95 ?
C52 C53 . 1.369(9) ?
C52 H52 . 0.95 ?
C53 C54 . 1.386(8) ?
C53 H53 . 0.95 ?
C54 H54 . 0.95 ?
C55 O10 . 1.347(5) ?
C55 C56 . 1.351(6) ?
C55 C64 . 1.504(6) ?
C56 C57 . 1.435(6) ?
C56 H56 . 0.95 ?
C57 O11 . 1.240(5) ?
C57 C58 . 1.471(6) ?
C58 C63 . 1.392(5) ?
C58 C59 . 1.398(6) ?
C59 C60 . 1.373(7) ?
C59 H59 . 0.95 ?
C60 C61 . 1.395(7) ?
C60 H60 . 0.95 ?
C61 C62 . 1.368(6) ?
C61 H61 . 0.95 ?
C62 C63 . 1.399(5) ?
C62 H62 . 0.95 ?
C63 O10 . 1.362(5) ?
C64 O12 . 1.228(5) ?
C64 N4 . 1.327(5) ?
C65 N4 . 1.469(5) ?
C65 C67 . 1.515(6) ?
C65 C66 . 1.515(6) ?
C65 H65 . 1.0 ?
C66 H66A . 0.98 ?
C66 H66B . 0.98 ?
C66 H66C . 0.98 ?
C67 C72 . 1.378(7) ?
C67 C68 . 1.393(7) ?
C68 C69 . 1.381(9) ?
C68 H68 . 0.95 ?
C69 C70 . 1.405(11) ?
C69 H69 . 0.95 ?
C70 C71 . 1.365(10) ?
C70 H70 . 0.95 ?
C71 C72 . 1.402(8) ?
C71 H71 . 0.95 ?
C72 H72 . 0.95 ?
N1 H1 . 0.88 ?
N2 H2A . 0.88 ?
N3 H3 . 0.88 ?
N4 H4 . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 O1 . . 124.8(3) ?
C2 C1 C10 . . 121.7(3) ?
O1 C1 C10 . . 113.4(3) ?
C1 C2 C3 . . 120.8(3) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
O2 C3 C2 . . 123.1(4) ?
O2 C3 C4 . . 122.6(4) ?
C2 C3 C4 . . 114.3(3) ?
C9 C4 C5 . . 119.2(3) ?
C9 C4 C3 . . 119.5(3) ?
C5 C4 C3 . . 121.3(3) ?
C6 C5 C4 . . 120.0(4) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C7 . . 119.7(4) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C8 C7 C6 . . 121.2(4) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 C9 . . 118.7(4) ?
C7 C8 H8 . . 120.6 ?
C9 C8 H8 . . 120.6 ?
O1 C9 C8 . . 116.6(3) ?
O1 C9 C4 . . 122.3(3) ?
C8 C9 C4 . . 121.1(3) ?
O3 C10 N1 . . 126.4(4) ?
O3 C10 C1 . . 119.2(4) ?
N1 C10 C1 . . 114.4(3) ?
N1 C11 C12 . . 109.6(4) ?
N1 C11 C13 . . 109.6(4) ?
C12 C11 C13 . . 115.3(4) ?
N1 C11 H11 . . 107.3 ?
C12 C11 H11 . . 107.3 ?
C13 C11 H11 . . 107.3 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C18 . . 117.9(5) ?
C14 C13 C11 . . 118.8(4) ?
C18 C13 C11 . . 123.3(5) ?
C15 C14 C13 . . 121.8(5) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C14 C15 C16 . . 119.4(6) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C17 C16 C15 . . 119.1(5) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C16 C17 C18 . . 122.1(6) ?
C16 C17 H17 . . 119.0 ?
C18 C17 H17 . . 119.0 ?
C17 C18 C13 . . 119.6(6) ?
C17 C18 H18 . . 120.2 ?
C13 C18 H18 . . 120.2 ?
C20 C19 O4 . . 123.4(4) ?
C20 C19 C28 . . 122.5(3) ?
O4 C19 C28 . . 114.1(3) ?
C19 C20 C21 . . 122.0(4) ?
C19 C20 H20 . . 119.0 ?
C21 C20 H20 . . 119.0 ?
O5 C21 C20 . . 123.7(4) ?
O5 C21 C22 . . 121.7(4) ?
C20 C21 C22 . . 114.6(3) ?
C23 C22 C27 . . 118.8(3) ?
C23 C22 C21 . . 121.7(3) ?
C27 C22 C21 . . 119.5(3) ?
C24 C23 C22 . . 120.0(3) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C23 C24 C25 . . 120.3(4) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C26 C25 C24 . . 120.7(4) ?
C26 C25 H25 . . 119.7 ?
C24 C25 H25 . . 119.7 ?
C25 C26 C27 . . 118.8(4) ?
C25 C26 H26 . . 120.6 ?
C27 C26 H26 . . 120.6 ?
O4 C27 C26 . . 116.7(3) ?
O4 C27 C22 . . 121.8(3) ?
C26 C27 C22 . . 121.5(3) ?
O6 C28 N2 . . 124.2(4) ?
O6 C28 C19 . . 118.1(4) ?
N2 C28 C19 . . 117.7(3) ?
N2 C29 C31 . . 111.2(3) ?
N2 C29 C30 . . 111.7(3) ?
C31 C29 C30 . . 113.0(4) ?
N2 C29 H29 . . 106.8 ?
C31 C29 H29 . . 106.8 ?
C30 C29 H29 . . 106.8 ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C32 C31 C36 . . 119.6(5) ?
C32 C31 C29 . . 121.2(4) ?
C36 C31 C29 . . 119.2(5) ?
C33 C32 C31 . . 120.8(7) ?
C33 C32 H32 . . 119.6 ?
C31 C32 H32 . . 119.6 ?
C32 C33 C34 . . 119.7(8) ?
C32 C33 H33 . . 120.2 ?
C34 C33 H33 . . 120.2 ?
C35 C34 C33 . . 119.2(6) ?
C35 C34 H34 . . 120.4 ?
C33 C34 H34 . . 120.4 ?
C34 C35 C36 . . 120.5(7) ?
C34 C35 H35 . . 119.8 ?
C36 C35 H35 . . 119.8 ?
C35 C36 C31 . . 120.1(7) ?
C35 C36 H36 . . 119.9 ?
C31 C36 H36 . . 119.9 ?
C38 C37 O7 . . 124.0(3) ?
C38 C37 C46 . . 122.7(3) ?
O7 C37 C46 . . 113.3(3) ?
C37 C38 C39 . . 121.1(3) ?
C37 C38 H38 . . 119.4 ?
C39 C38 H38 . . 119.4 ?
O8 C39 C38 . . 122.7(4) ?
O8 C39 C40 . . 123.0(4) ?
C38 C39 C40 . . 114.3(3) ?
C41 C40 C45 . . 118.1(4) ?
C41 C40 C39 . . 122.3(4) ?
C45 C40 C39 . . 119.7(3) ?
C42 C41 C40 . . 120.7(4) ?
C42 C41 H41 . . 119.6 ?
C40 C41 H41 . . 119.6 ?
C41 C42 C43 . . 119.9(4) ?
C41 C42 H42 . . 120.0 ?
C43 C42 H42 . . 120.0 ?
C44 C43 C42 . . 120.9(4) ?
C44 C43 H43 . . 119.6 ?
C42 C43 H43 . . 119.6 ?
C43 C44 C45 . . 118.7(4) ?
C43 C44 H44 . . 120.7 ?
C45 C44 H44 . . 120.7 ?
O7 C45 C44 . . 116.1(3) ?
O7 C45 C40 . . 122.2(3) ?
C44 C45 C40 . . 121.8(4) ?
O9 C46 N3 . . 124.6(4) ?
O9 C46 C37 . . 119.5(3) ?
N3 C46 C37 . . 115.9(3) ?
N3 C47 C48 . . 110.5(3) ?
N3 C47 C49 . . 109.8(3) ?
C48 C47 C49 . . 115.2(4) ?
N3 C47 H47 . . 107.0 ?
C48 C47 H47 . . 107.0 ?
C49 C47 H47 . . 107.0 ?
C47 C48 H48A . . 109.5 ?
C47 C48 H48B . . 109.5 ?
H48A C48 H48B . . 109.5 ?
C47 C48 H48C . . 109.5 ?
H48A C48 H48C . . 109.5 ?
H48B C48 H48C . . 109.5 ?
C50 C49 C54 . . 118.8(4) ?
C50 C49 C47 . . 118.7(4) ?
C54 C49 C47 . . 122.4(4) ?
C51 C50 C49 . . 121.2(4) ?
C51 C50 H50 . . 119.4 ?
C49 C50 H50 . . 119.4 ?
C50 C51 C52 . . 119.9(5) ?
C50 C51 H51 . . 120.0 ?
C52 C51 H51 . . 120.0 ?
C53 C52 C51 . . 119.1(5) ?
C53 C52 H52 . . 120.5 ?
C51 C52 H52 . . 120.5 ?
C52 C53 C54 . . 121.6(5) ?
C52 C53 H53 . . 119.2 ?
C54 C53 H53 . . 119.2 ?
C53 C54 C49 . . 119.4(5) ?
C53 C54 H54 . . 120.3 ?
C49 C54 H54 . . 120.3 ?
O10 C55 C56 . . 123.9(4) ?
O10 C55 C64 . . 112.9(3) ?
C56 C55 C64 . . 123.2(4) ?
C55 C56 C57 . . 120.4(4) ?
C55 C56 H56 . . 119.8 ?
C57 C56 H56 . . 119.8 ?
O11 C57 C56 . . 123.1(4) ?
O11 C57 C58 . . 121.5(4) ?
C56 C57 C58 . . 115.4(3) ?
C63 C58 C59 . . 118.2(4) ?
C63 C58 C57 . . 119.1(4) ?
C59 C58 C57 . . 122.7(4) ?
C60 C59 C58 . . 120.6(4) ?
C60 C59 H59 . . 119.7 ?
C58 C59 H59 . . 119.7 ?
C59 C60 C61 . . 119.9(4) ?
C59 C60 H60 . . 120.1 ?
C61 C60 H60 . . 120.1 ?
C62 C61 C60 . . 121.3(4) ?
C62 C61 H61 . . 119.3 ?
C60 C61 H61 . . 119.3 ?
C61 C62 C63 . . 118.2(4) ?
C61 C62 H62 . . 120.9 ?
C63 C62 H62 . . 120.9 ?
O10 C63 C58 . . 122.1(3) ?
O10 C63 C62 . . 116.1(3) ?
C58 C63 C62 . . 121.8(4) ?
O12 C64 N4 . . 125.2(4) ?
O12 C64 C55 . . 119.7(3) ?
N4 C64 C55 . . 115.2(3) ?
N4 C65 C67 . . 110.4(3) ?
N4 C65 C66 . . 109.0(4) ?
C67 C65 C66 . . 115.5(4) ?
N4 C65 H65 . . 107.2 ?
C67 C65 H65 . . 107.2 ?
C66 C65 H65 . . 107.2 ?
C65 C66 H66A . . 109.5 ?
C65 C66 H66B . . 109.5 ?
H66A C66 H66B . . 109.5 ?
C65 C66 H66C . . 109.5 ?
H66A C66 H66C . . 109.5 ?
H66B C66 H66C . . 109.5 ?
C72 C67 C68 . . 118.4(5) ?
C72 C67 C65 . . 119.4(4) ?
C68 C67 C65 . . 122.2(4) ?
C69 C68 C67 . . 121.1(6) ?
C69 C68 H68 . . 119.5 ?
C67 C68 H68 . . 119.5 ?
C68 C69 C70 . . 119.9(5) ?
C68 C69 H69 . . 120.0 ?
C70 C69 H69 . . 120.0 ?
C71 C70 C69 . . 119.2(5) ?
C71 C70 H70 . . 120.4 ?
C69 C70 H70 . . 120.4 ?
C70 C71 C72 . . 120.4(6) ?
C70 C71 H71 . . 119.8 ?
C72 C71 H71 . . 119.8 ?
C67 C72 C71 . . 121.0(5) ?
C67 C72 H72 . . 119.5 ?
C71 C72 H72 . . 119.5 ?
C10 N1 C11 . . 120.5(3) ?
C10 N1 H1 . . 119.7 ?
C11 N1 H1 . . 119.7 ?
C28 N2 C29 . . 118.9(3) ?
C28 N2 H2A . . 120.6 ?
C29 N2 H2A . . 120.6 ?
C46 N3 C47 . . 121.4(3) ?
C46 N3 H3 . . 119.3 ?
C47 N3 H3 . . 119.3 ?
C64 N4 C65 . . 122.6(3) ?
C64 N4 H4 . . 118.7 ?
C65 N4 H4 . . 118.7 ?
C1 O1 C9 . . 118.3(3) ?
C19 O4 C27 . . 118.8(3) ?
C37 O7 C45 . . 118.5(3) ?
C55 O10 C63 . . 119.1(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 0.4(6) ?
C10 C1 C2 C3 . . . . -175.5(3) ?
C1 C2 C3 O2 . . . . -177.6(4) ?
C1 C2 C3 C4 . . . . 2.7(5) ?
O2 C3 C4 C9 . . . . 177.2(4) ?
C2 C3 C4 C9 . . . . -3.1(5) ?
O2 C3 C4 C5 . . . . -3.4(6) ?
C2 C3 C4 C5 . . . . 176.2(3) ?
C9 C4 C5 C6 . . . . -0.3(6) ?
C3 C4 C5 C6 . . . . -179.6(4) ?
C4 C5 C6 C7 . . . . -0.8(6) ?
C5 C6 C7 C8 . . . . 1.9(7) ?
C6 C7 C8 C9 . . . . -1.8(6) ?
C7 C8 C9 O1 . . . . 179.9(4) ?
C7 C8 C9 C4 . . . . 0.7(6) ?
C5 C4 C9 O1 . . . . -178.8(3) ?
C3 C4 C9 O1 . . . . 0.5(5) ?
C5 C4 C9 C8 . . . . 0.3(5) ?
C3 C4 C9 C8 . . . . 179.7(3) ?
C2 C1 C10 O3 . . . . -18.1(6) ?
O1 C1 C10 O3 . . . . 165.5(4) ?
C2 C1 C10 N1 . . . . 160.7(4) ?
O1 C1 C10 N1 . . . . -15.7(5) ?
N1 C11 C13 C14 . . . . 60.7(5) ?
C12 C11 C13 C14 . . . . -175.0(4) ?
N1 C11 C13 C18 . . . . -118.8(5) ?
C12 C11 C13 C18 . . . . 5.4(6) ?
C18 C13 C14 C15 . . . . 0.7(7) ?
C11 C13 C14 C15 . . . . -178.8(4) ?
C13 C14 C15 C16 . . . . -1.6(8) ?
C14 C15 C16 C17 . . . . 1.3(8) ?
C15 C16 C17 C18 . . . . -0.3(9) ?
C16 C17 C18 C13 . . . . -0.6(8) ?
C14 C13 C18 C17 . . . . 0.4(7) ?
C11 C13 C18 C17 . . . . 179.9(4) ?
O4 C19 C20 C21 . . . . -0.7(6) ?
C28 C19 C20 C21 . . . . 177.7(3) ?
C19 C20 C21 O5 . . . . 179.3(4) ?
C19 C20 C21 C22 . . . . -0.9(5) ?
O5 C21 C22 C23 . . . . 1.1(5) ?
C20 C21 C22 C23 . . . . -178.7(3) ?
O5 C21 C22 C27 . . . . -178.1(3) ?
C20 C21 C22 C27 . . . . 2.0(5) ?
C27 C22 C23 C24 . . . . -0.2(5) ?
C21 C22 C23 C24 . . . . -179.5(3) ?
C22 C23 C24 C25 . . . . 0.2(6) ?
C23 C24 C25 C26 . . . . -0.5(7) ?
C24 C25 C26 C27 . . . . 0.8(7) ?
C25 C26 C27 O4 . . . . -179.3(4) ?
C25 C26 C27 C22 . . . . -0.9(6) ?
C23 C22 C27 O4 . . . . 178.9(3) ?
C21 C22 C27 O4 . . . . -1.8(5) ?
C23 C22 C27 C26 . . . . 0.6(5) ?
C21 C22 C27 C26 . . . . 179.9(3) ?
C20 C19 C28 O6 . . . . 3.6(5) ?
O4 C19 C28 O6 . . . . -177.9(4) ?
C20 C19 C28 N2 . . . . -174.2(4) ?
O4 C19 C28 N2 . . . . 4.3(5) ?
N2 C29 C31 C32 . . . . -70.6(5) ?
C30 C29 C31 C32 . . . . 56.0(5) ?
N2 C29 C31 C36 . . . . 111.8(4) ?
C30 C29 C31 C36 . . . . -121.6(4) ?
C36 C31 C32 C33 . . . . 0.6(7) ?
C29 C31 C32 C33 . . . . -177.0(5) ?
C31 C32 C33 C34 . . . . -1.2(9) ?
C32 C33 C34 C35 . . . . 0.4(9) ?
C33 C34 C35 C36 . . . . 0.9(9) ?
C34 C35 C36 C31 . . . . -1.4(8) ?
C32 C31 C36 C35 . . . . 0.7(6) ?
C29 C31 C36 C35 . . . . 178.3(4) ?
O7 C37 C38 C39 . . . . 0.1(6) ?
C46 C37 C38 C39 . . . . -178.3(3) ?
C37 C38 C39 O8 . . . . -176.6(4) ?
C37 C38 C39 C40 . . . . 3.9(5) ?
O8 C39 C40 C41 . . . . -4.9(6) ?
C38 C39 C40 C41 . . . . 174.6(4) ?
O8 C39 C40 C45 . . . . 176.2(4) ?
C38 C39 C40 C45 . . . . -4.3(5) ?
C45 C40 C41 C42 . . . . -0.4(6) ?
C39 C40 C41 C42 . . . . -179.3(4) ?
C40 C41 C42 C43 . . . . -0.6(7) ?
C41 C42 C43 C44 . . . . 1.1(8) ?
C42 C43 C44 C45 . . . . -0.5(7) ?
C43 C44 C45 O7 . . . . 178.6(4) ?
C43 C44 C45 C40 . . . . -0.5(6) ?
C41 C40 C45 O7 . . . . -178.1(3) ?
C39 C40 C45 O7 . . . . 0.8(5) ?
C41 C40 C45 C44 . . . . 1.0(5) ?
C39 C40 C45 C44 . . . . 179.9(3) ?
C38 C37 C46 O9 . . . . -8.8(6) ?
O7 C37 C46 O9 . . . . 172.7(4) ?
C38 C37 C46 N3 . . . . 169.9(4) ?
O7 C37 C46 N3 . . . . -8.7(5) ?
N3 C47 C49 C50 . . . . 58.8(5) ?
C48 C47 C49 C50 . . . . -175.8(4) ?
N3 C47 C49 C54 . . . . -122.2(4) ?
C48 C47 C49 C54 . . . . 3.3(5) ?
C54 C49 C50 C51 . . . . -1.4(6) ?
C47 C49 C50 C51 . . . . 177.7(4) ?
C49 C50 C51 C52 . . . . 2.4(8) ?
C50 C51 C52 C53 . . . . -1.6(9) ?
C51 C52 C53 C54 . . . . -0.2(9) ?
C52 C53 C54 C49 . . . . 1.2(8) ?
C50 C49 C54 C53 . . . . -0.4(6) ?
C47 C49 C54 C53 . . . . -179.4(4) ?
O10 C55 C56 C57 . . . . 1.0(6) ?
C64 C55 C56 C57 . . . . -178.6(3) ?
C55 C56 C57 O11 . . . . 177.3(4) ?
C55 C56 C57 C58 . . . . -2.0(5) ?
O11 C57 C58 C63 . . . . -176.8(3) ?
C56 C57 C58 C63 . . . . 2.4(5) ?
O11 C57 C58 C59 . . . . 0.4(6) ?
C56 C57 C58 C59 . . . . 179.6(3) ?
C63 C58 C59 C60 . . . . -1.1(5) ?
C57 C58 C59 C60 . . . . -178.3(3) ?
C58 C59 C60 C61 . . . . 1.1(6) ?
C59 C60 C61 C62 . . . . -1.0(6) ?
C60 C61 C62 C63 . . . . 1.0(6) ?
C59 C58 C63 O10 . . . . -179.4(3) ?
C57 C58 C63 O10 . . . . -2.1(5) ?
C59 C58 C63 C62 . . . . 1.1(5) ?
C57 C58 C63 C62 . . . . 178.4(3) ?
C61 C62 C63 O10 . . . . 179.4(4) ?
C61 C62 C63 C58 . . . . -1.1(6) ?
O10 C55 C64 O12 . . . . -173.4(3) ?
C56 C55 C64 O12 . . . . 6.3(6) ?
O10 C55 C64 N4 . . . . 5.6(4) ?
C56 C55 C64 N4 . . . . -174.7(3) ?
N4 C65 C67 C72 . . . . 87.0(5) ?
C66 C65 C67 C72 . . . . -148.9(4) ?
N4 C65 C67 C68 . . . . -90.2(5) ?
C66 C65 C67 C68 . . . . 33.9(6) ?
C72 C67 C68 C69 . . . . 0.2(7) ?
C65 C67 C68 C69 . . . . 177.5(5) ?
C67 C68 C69 C70 . . . . -0.2(8) ?
C68 C69 C70 C71 . . . . -0.1(8) ?
C69 C70 C71 C72 . . . . 0.3(9) ?
C68 C67 C72 C71 . . . . 0.0(7) ?
C65 C67 C72 C71 . . . . -177.4(4) ?
C70 C71 C72 C67 . . . . -0.2(8) ?
O3 C10 N1 C11 . . . . 8.4(8) ?
C1 C10 N1 C11 . . . . -170.3(4) ?
C12 C11 N1 C10 . . . . 85.8(6) ?
C13 C11 N1 C10 . . . . -146.8(4) ?
O6 C28 N2 C29 . . . . -5.9(6) ?
C19 C28 N2 C29 . . . . 171.8(3) ?
C31 C29 N2 C28 . . . . -145.2(4) ?
C30 C29 N2 C28 . . . . 87.5(5) ?
O9 C46 N3 C47 . . . . 4.7(6) ?
C37 C46 N3 C47 . . . . -173.8(3) ?
C48 C47 N3 C46 . . . . 89.0(5) ?
C49 C47 N3 C46 . . . . -142.9(4) ?
O12 C64 N4 C65 . . . . 0.3(6) ?
C55 C64 N4 C65 . . . . -178.7(3) ?
C67 C65 N4 C64 . . . . -99.9(4) ?
C66 C65 N4 C64 . . . . 132.3(4) ?
C2 C1 O1 C9 . . . . -3.3(5) ?
C10 C1 O1 C9 . . . . 173.0(3) ?
C8 C9 O1 C1 . . . . -176.5(3) ?
C4 C9 O1 C1 . . . . 2.7(5) ?
C20 C19 O4 C27 . . . . 1.1(5) ?
C28 C19 O4 C27 . . . . -177.5(3) ?
C26 C27 O4 C19 . . . . 178.6(3) ?
C22 C27 O4 C19 . . . . 0.2(5) ?
C38 C37 O7 C45 . . . . -4.0(5) ?
C46 C37 O7 C45 . . . . 174.6(3) ?
C44 C45 O7 C37 . . . . -175.7(3) ?
C40 C45 O7 C37 . . . . 3.4(5) ?
C56 C55 O10 C63 . . . . -0.5(5) ?
C64 C55 O10 C63 . . . . 179.2(3) ?
C58 C63 O10 C55 . . . . 1.0(5) ?
C62 C63 O10 C55 . . . . -179.5(3) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3, Hexane'
_database_code_depnum_ccdc_archive 'CCDC 1010749'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        (R)-N-(1-t-Butylethyl)-2-chromonecarboxamide
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         273.32
_chemical_absolute_configuration syn

_chemical_melting_point          359-360

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.9167(9)
_cell_length_b                   10.9747(17)
_cell_length_c                   12.2265(18)
_cell_angle_alpha                64.4240(19)
_cell_angle_beta                 82.5940(19)
_cell_angle_gamma                89.9950(19)
_cell_volume                     708.78(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1299
_cell_measurement_theta_min      3.3295
_cell_measurement_theta_max      27.0350
_cell_measurement_temperature    173

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'graphite '

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            3806
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3228
_reflns_number_gt                2931
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1043
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.024
_refine_ls_number_reflns         3228
_refine_ls_number_parameters     369
_refine_ls_number_restraints     107
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+0.0180P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'SHELXT(George Sheldrick, 2012)'
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 366 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.7(10)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2673(5) 0.8206(3) 0.1716(3) 0.0244(6) Uani d U . . 1 . .
C C2 0.0856(5) 0.7659(3) 0.1495(3) 0.0288(7) Uani d U . . 1 . .
H H2 0.0486 0.6714 0.1943 0.035 Uiso calc U . R 1 . .
C C3 -0.0550(5) 0.8465(3) 0.0595(3) 0.0251(6) Uani d U . . 1 . .
C C4 0.0040(5) 0.9924(3) 0.0053(3) 0.0237(6) Uani d U . . 1 . .
C C5 -0.1283(5) 1.0874(3) -0.0735(3) 0.0270(7) Uani d U . . 1 . .
H H5 -0.2632 1.0578 -0.0919 0.032 Uiso calc U . R 1 . .
C C6 -0.0652(5) 1.2232(3) -0.1245(3) 0.0291(7) Uani d U . . 1 . .
H H6 -0.1565 1.2873 -0.1775 0.035 Uiso calc U . R 1 . .
C C7 0.1345(5) 1.2668(3) -0.0980(3) 0.0279(7) Uani d U . . 1 . .
H H7 0.1791 1.3606 -0.1346 0.033 Uiso calc U . R 1 . .
C C8 0.2662(5) 1.1766(3) -0.0202(3) 0.0240(6) Uani d U . . 1 . .
H H8 0.4017 1.2069 -0.0028 0.029 Uiso calc U . R 1 . .
C C9 0.1979(5) 1.0394(3) 0.0332(3) 0.0216(6) Uani d U . . 1 . .
C C10 0.4172(5) 0.7459(3) 0.2679(3) 0.0262(6) Uani d U . . 1 . .
C C11 0.5499(5) 0.5220(3) 0.3948(3) 0.0240(6) Uani d U . . 1 . .
H H11 0.6648 0.5793 0.4081 0.029 Uiso calc U . R 1 . .
C C12 0.6801(5) 0.4322(3) 0.3460(3) 0.0321(7) Uani d U . . 1 . .
H H12A 0.5718 0.3779 0.3283 0.048 Uiso calc U . R 1 . .
H H12B 0.7703 0.3721 0.4075 0.048 Uiso calc U . R 1 . .
H H12C 0.7822 0.4888 0.2707 0.048 Uiso calc U . R 1 . .
C C13 0.3941(5) 0.4424(3) 0.5185(3) 0.0286(6) Uani d U . . 1 . .
C C14 0.2603(7) 0.5409(4) 0.5556(3) 0.0475(9) Uani d U . . 1 . .
H H14A 0.1578 0.5876 0.4956 0.071 Uiso calc U . R 1 . .
H H14B 0.3669 0.6074 0.5585 0.071 Uiso calc U . R 1 . .
H H14C 0.1704 0.4908 0.6366 0.071 Uiso calc U . R 1 . .
C C15 0.5461(6) 0.3672(4) 0.6168(3) 0.0408(8) Uani d U . . 1 . .
H H15A 0.4505 0.3191 0.6964 0.061 Uiso calc U . R 1 . .
H H15B 0.6532 0.4325 0.6212 0.061 Uiso calc U . R 1 . .
H H15C 0.6316 0.3021 0.5955 0.061 Uiso calc U . R 1 . .
C C16 0.2288(6) 0.3417(4) 0.5103(4) 0.0476(9) Uani d U . . 1 . .
H H16A 0.125 0.2978 0.5876 0.071 Uiso calc U . R 1 . .
H H16B 0.3145 0.2731 0.4946 0.071 Uiso calc U . R 1 . .
H H16C 0.1401 0.3893 0.4432 0.071 Uiso calc U . R 1 . .
C C17 0.7997(5) 0.4547(3) 1.0202(3) 0.0233(6) Uani d U . . 1 . .
C C18 0.9895(5) 0.5067(3) 1.0374(3) 0.0262(6) Uani d U . . 1 . .
H H18 1.0377 0.5988 0.9865 0.031 Uiso calc U . R 1 . .
C C19 1.1228(5) 0.4256(3) 1.1319(3) 0.0248(6) Uani d U . . 1 . .
C C20 1.0467(5) 0.2822(3) 1.1955(3) 0.0229(6) Uani d U . . 1 . .
C C21 1.1704(5) 0.1859(3) 1.2786(3) 0.0275(7) Uani d U . . 1 . .
H H21 1.305 0.2142 1.2982 0.033 Uiso calc U . R 1 . .
C C22 1.1008(5) 0.0509(3) 1.3325(3) 0.0314(7) Uani d U . . 1 . .
H H22 1.1892 -0.0138 1.3871 0.038 Uiso calc U . R 1 . .
C C23 0.8984(5) 0.0090(3) 1.3065(3) 0.0281(7) Uani d U . . 1 . .
H H23 0.8488 -0.0842 1.3449 0.034 Uiso calc U . R 1 . .
C C24 0.7711(5) 0.1015(3) 1.2261(3) 0.0253(6) Uani d U . . 1 . .
H H24 0.6334 0.0732 1.2091 0.03 Uiso calc U . R 1 . .
C C25 0.8481(5) 0.2369(3) 1.1703(3) 0.0220(6) Uani d U . . 1 . .
C C26 0.6634(5) 0.5255(3) 0.9161(3) 0.0259(6) Uani d U . . 1 . .
C C27 0.5988(5) 0.7353(3) 0.7441(3) 0.0272(6) Uani d U . . 1 . .
H H27 0.4494 0.6895 0.7488 0.033 Uiso calc U . R 1 . .
C C28 0.7658(7) 0.7194(4) 0.6454(3) 0.0412(8) Uani d U . . 1 . .
H H28A 0.9155 0.7618 0.6393 0.062 Uiso calc U . R 1 . .
H H28B 0.7087 0.7632 0.5664 0.062 Uiso calc U . R 1 . .
H H28C 0.7801 0.623 0.6672 0.062 Uiso calc U . R 1 . .
C C29 0.5541(5) 0.8822(3) 0.7176(3) 0.0273(6) Uani d U . . 1 . .
C C30 0.4421(6) 0.9454(4) 0.6001(3) 0.0414(8) Uani d U . . 1 . .
H H30A 0.3112 0.8864 0.6073 0.062 Uiso calc U . R 1 . .
H H30B 0.5535 0.9556 0.5296 0.062 Uiso calc U . R 1 . .
H H30C 0.3902 1.0343 0.5887 0.062 Uiso calc U . R 1 . .
C C31 0.7735(6) 0.9670(3) 0.6990(3) 0.0362(7) Uani d U . . 1 . .
H H31A 0.7366 1.0602 0.6813 0.054 Uiso calc U . R 1 . .
H H31B 0.8787 0.9668 0.6302 0.054 Uiso calc U . R 1 . .
H H31C 0.8457 0.9284 0.7736 0.054 Uiso calc U . R 1 . .
C C32 0.3868(6) 0.8851(4) 0.8233(3) 0.0384(8) Uani d U . . 1 . .
H H32A 0.2478 0.8293 0.8362 0.058 Uiso calc U . R 1 . .
H H32B 0.3478 0.9785 0.8029 0.058 Uiso calc U . R 1 . .
H H32C 0.4581 0.8495 0.8982 0.058 Uiso calc U . R 1 . .
N N1 0.4228(4) 0.6125(2) 0.2991(2) 0.0251(5) Uani d U . . 1 . .
H H1 0.3469 0.5782 0.2605 0.03 Uiso calc U . R 1 . .
N N2 0.6813(4) 0.6608(2) 0.8632(2) 0.0265(6) Uani d U . . 1 . .
H H2A 0.7415 0.705 0.8989 0.032 Uiso calc U . R 1 . .
O O1 0.3328(3) 0.95340(19) 0.11362(17) 0.0245(5) Uani d U . . 1 . .
O O2 -0.2100(4) 0.7968(2) 0.0300(2) 0.0346(5) Uani d U . . 1 . .
O O3 0.5130(4) 0.8051(2) 0.3153(2) 0.0397(6) Uani d U . . 1 . .
O O4 0.7197(3) 0.32446(19) 1.08632(18) 0.0252(5) Uani d U . . 1 . .
O O5 1.2887(3) 0.4733(2) 1.1563(2) 0.0327(5) Uani d U . . 1 . .
O O6 0.5589(4) 0.4576(2) 0.8792(2) 0.0371(5) Uani d U . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.344(4) ?
C1 O1 . 1.347(3) ?
C1 C10 . 1.510(4) ?
C2 C3 . 1.442(4) ?
C2 H2 . 0.95 ?
C3 O2 . 1.234(3) ?
C3 C4 . 1.466(4) ?
C4 C9 . 1.397(4) ?
C4 C5 . 1.398(4) ?
C5 C6 . 1.374(5) ?
C5 H5 . 0.95 ?
C6 C7 . 1.401(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.368(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.392(4) ?
C8 H8 . 0.95 ?
C9 O1 . 1.377(3) ?
C10 O3 . 1.220(4) ?
C10 N1 . 1.346(4) ?
C11 N1 . 1.464(3) ?
C11 C12 . 1.519(4) ?
C11 C13 . 1.549(4) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C16 . 1.519(5) ?
C13 C14 . 1.527(5) ?
C13 C15 . 1.535(4) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 C18 . 1.340(4) ?
C17 O4 . 1.350(4) ?
C17 C26 . 1.512(4) ?
C18 C19 . 1.447(4) ?
C18 H18 . 0.95 ?
C19 O5 . 1.239(4) ?
C19 C20 . 1.462(4) ?
C20 C21 . 1.396(4) ?
C20 C25 . 1.396(4) ?
C21 C22 . 1.373(5) ?
C21 H21 . 0.95 ?
C22 C23 . 1.404(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.376(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.388(4) ?
C24 H24 . 0.95 ?
C25 O4 . 1.380(3) ?
C26 O6 . 1.226(4) ?
C26 N2 . 1.338(4) ?
C27 N2 . 1.477(3) ?
C27 C28 . 1.529(4) ?
C27 C29 . 1.531(4) ?
C27 H27 . 1.0 ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?
C29 C31 . 1.531(4) ?
C29 C32 . 1.536(4) ?
C29 C30 . 1.539(4) ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?
C31 H31A . 0.98 ?
C31 H31B . 0.98 ?
C31 H31C . 0.98 ?
C32 H32A . 0.98 ?
C32 H32B . 0.98 ?
C32 H32C . 0.98 ?
N1 H1 . 0.88 ?
N2 H2A . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 O1 . . 123.6(3) ?
C2 C1 C10 . . 125.7(3) ?
O1 C1 C10 . . 110.6(2) ?
C1 C2 C3 . . 121.9(3) ?
C1 C2 H2 . . 119.1 ?
C3 C2 H2 . . 119.1 ?
O2 C3 C2 . . 122.9(3) ?
O2 C3 C4 . . 123.0(3) ?
C2 C3 C4 . . 114.1(2) ?
C9 C4 C5 . . 118.3(3) ?
C9 C4 C3 . . 119.4(2) ?
C5 C4 C3 . . 122.3(3) ?
C6 C5 C4 . . 120.6(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 119.6(3) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C8 C7 C6 . . 121.2(3) ?
C8 C7 H7 . . 119.4 ?
C6 C7 H7 . . 119.4 ?
C7 C8 C9 . . 118.7(3) ?
C7 C8 H8 . . 120.7 ?
C9 C8 H8 . . 120.7 ?
O1 C9 C8 . . 116.3(2) ?
O1 C9 C4 . . 122.2(2) ?
C8 C9 C4 . . 121.5(3) ?
O3 C10 N1 . . 124.9(3) ?
O3 C10 C1 . . 120.3(3) ?
N1 C10 C1 . . 114.7(2) ?
N1 C11 C12 . . 107.7(2) ?
N1 C11 C13 . . 112.3(2) ?
C12 C11 C13 . . 113.8(2) ?
N1 C11 H11 . . 107.6 ?
C12 C11 H11 . . 107.6 ?
C13 C11 H11 . . 107.6 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C16 C13 C14 . . 109.5(3) ?
C16 C13 C15 . . 109.8(3) ?
C14 C13 C15 . . 108.1(3) ?
C16 C13 C11 . . 111.3(2) ?
C14 C13 C11 . . 109.7(3) ?
C15 C13 C11 . . 108.4(2) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 O4 . . 123.7(3) ?
C18 C17 C26 . . 125.6(3) ?
O4 C17 C26 . . 110.3(2) ?
C17 C18 C19 . . 121.5(3) ?
C17 C18 H18 . . 119.3 ?
C19 C18 H18 . . 119.3 ?
O5 C19 C18 . . 123.0(3) ?
O5 C19 C20 . . 122.7(3) ?
C18 C19 C20 . . 114.4(3) ?
C21 C20 C25 . . 117.8(3) ?
C21 C20 C19 . . 122.4(3) ?
C25 C20 C19 . . 119.8(3) ?
C22 C21 C20 . . 121.2(3) ?
C22 C21 H21 . . 119.4 ?
C20 C21 H21 . . 119.4 ?
C21 C22 C23 . . 119.6(3) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C24 C23 C22 . . 120.7(3) ?
C24 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C23 C24 C25 . . 118.6(3) ?
C23 C24 H24 . . 120.7 ?
C25 C24 H24 . . 120.7 ?
O4 C25 C24 . . 116.3(2) ?
O4 C25 C20 . . 121.6(3) ?
C24 C25 C20 . . 122.1(3) ?
O6 C26 N2 . . 124.0(3) ?
O6 C26 C17 . . 119.1(3) ?
N2 C26 C17 . . 116.7(2) ?
N2 C27 C28 . . 108.2(2) ?
N2 C27 C29 . . 112.4(2) ?
C28 C27 C29 . . 114.4(3) ?
N2 C27 H27 . . 107.2 ?
C28 C27 H27 . . 107.2 ?
C29 C27 H27 . . 107.2 ?
C27 C28 H28A . . 109.5 ?
C27 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C27 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C27 C29 C31 . . 112.5(2) ?
C27 C29 C32 . . 109.5(2) ?
C31 C29 C32 . . 109.6(3) ?
C27 C29 C30 . . 108.3(2) ?
C31 C29 C30 . . 108.7(3) ?
C32 C29 C30 . . 108.2(3) ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C29 C31 H31A . . 109.5 ?
C29 C31 H31B . . 109.5 ?
H31A C31 H31B . . 109.5 ?
C29 C31 H31C . . 109.5 ?
H31A C31 H31C . . 109.5 ?
H31B C31 H31C . . 109.5 ?
C29 C32 H32A . . 109.5 ?
C29 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C29 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
C10 N1 C11 . . 122.7(2) ?
C10 N1 H1 . . 118.6 ?
C11 N1 H1 . . 118.6 ?
C26 N2 C27 . . 119.2(2) ?
C26 N2 H2A . . 120.4 ?
C27 N2 H2A . . 120.4 ?
C1 O1 C9 . . 118.3(2) ?
C17 O4 C25 . . 118.6(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 0.5(5) ?
C10 C1 C2 C3 . . . . 176.8(3) ?
C1 C2 C3 O2 . . . . 173.4(3) ?
C1 C2 C3 C4 . . . . -6.0(4) ?
O2 C3 C4 C9 . . . . -172.7(3) ?
C2 C3 C4 C9 . . . . 6.7(4) ?
O2 C3 C4 C5 . . . . 7.7(4) ?
C2 C3 C4 C5 . . . . -173.0(3) ?
C9 C4 C5 C6 . . . . 1.7(4) ?
C3 C4 C5 C6 . . . . -178.7(3) ?
C4 C5 C6 C7 . . . . 0.4(5) ?
C5 C6 C7 C8 . . . . -1.2(4) ?
C6 C7 C8 C9 . . . . -0.2(4) ?
C7 C8 C9 O1 . . . . -178.1(2) ?
C7 C8 C9 C4 . . . . 2.4(4) ?
C5 C4 C9 O1 . . . . 177.4(3) ?
C3 C4 C9 O1 . . . . -2.3(4) ?
C5 C4 C9 C8 . . . . -3.2(4) ?
C3 C4 C9 C8 . . . . 177.2(3) ?
C2 C1 C10 O3 . . . . -150.5(3) ?
O1 C1 C10 O3 . . . . 26.3(4) ?
C2 C1 C10 N1 . . . . 26.1(4) ?
O1 C1 C10 N1 . . . . -157.2(3) ?
N1 C11 C13 C16 . . . . 67.5(3) ?
C12 C11 C13 C16 . . . . -55.2(3) ?
N1 C11 C13 C14 . . . . -53.9(3) ?
C12 C11 C13 C14 . . . . -176.5(3) ?
N1 C11 C13 C15 . . . . -171.7(2) ?
C12 C11 C13 C15 . . . . 65.6(3) ?
O4 C17 C18 C19 . . . . -1.2(4) ?
C26 C17 C18 C19 . . . . -172.8(3) ?
C17 C18 C19 O5 . . . . -174.2(3) ?
C17 C18 C19 C20 . . . . 6.3(4) ?
O5 C19 C20 C21 . . . . -7.4(5) ?
C18 C19 C20 C21 . . . . 172.0(3) ?
O5 C19 C20 C25 . . . . 175.0(3) ?
C18 C19 C20 C25 . . . . -5.6(4) ?
C25 C20 C21 C22 . . . . 0.9(4) ?
C19 C20 C21 C22 . . . . -176.8(3) ?
C20 C21 C22 C23 . . . . -1.8(4) ?
C21 C22 C23 C24 . . . . 1.1(4) ?
C22 C23 C24 C25 . . . . 0.6(4) ?
C23 C24 C25 O4 . . . . 177.2(2) ?
C23 C24 C25 C20 . . . . -1.6(4) ?
C21 C20 C25 O4 . . . . -177.8(2) ?
C19 C20 C25 O4 . . . . -0.1(4) ?
C21 C20 C25 C24 . . . . 0.9(4) ?
C19 C20 C25 C24 . . . . 178.6(3) ?
C18 C17 C26 O6 . . . . 150.0(3) ?
O4 C17 C26 O6 . . . . -22.6(4) ?
C18 C17 C26 N2 . . . . -24.5(4) ?
O4 C17 C26 N2 . . . . 162.9(3) ?
N2 C27 C29 C31 . . . . 66.6(3) ?
C28 C27 C29 C31 . . . . -57.3(3) ?
N2 C27 C29 C32 . . . . -55.5(3) ?
C28 C27 C29 C32 . . . . -179.4(3) ?
N2 C27 C29 C30 . . . . -173.2(2) ?
C28 C27 C29 C30 . . . . 62.8(3) ?
O3 C10 N1 C11 . . . . -0.8(5) ?
C1 C10 N1 C11 . . . . -177.1(2) ?
C12 C11 N1 C10 . . . . -134.7(3) ?
C13 C11 N1 C10 . . . . 99.2(3) ?
O6 C26 N2 C27 . . . . -8.6(5) ?
C17 C26 N2 C27 . . . . 165.6(2) ?
C28 C27 N2 C26 . . . . -72.5(4) ?
C29 C27 N2 C26 . . . . 160.2(3) ?
C2 C1 O1 C9 . . . . 4.5(4) ?
C10 C1 O1 C9 . . . . -172.3(2) ?
C8 C9 O1 C1 . . . . 177.0(2) ?
C4 C9 O1 C1 . . . . -3.5(4) ?
C18 C17 O4 C25 . . . . -5.0(4) ?
C26 C17 O4 C25 . . . . 167.8(2) ?
C24 C25 O4 C17 . . . . -173.2(2) ?
C20 C25 O4 C17 . . . . 5.6(4) ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
_database_code_depnum_ccdc_archive 'CCDC 1010750'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_saka362_p212121

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'anti-HH Photodimer of (R)-N-(1-phenylethyl)-2-chromonecarboxamide'
_chemical_name_common            ?
_chemical_melting_point          518-519
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H30 N2 O6'
_chemical_formula_weight         586.62
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   12.2096(9)
_cell_length_b                   13.7443(10)
_cell_length_c                   18.0044(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3021.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    2760
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      20.87

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   'SADABS Sheldrick 1997'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14504
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.06
_reflns_number_total             5358
_reflns_number_gt                4369
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0712P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(11)
_refine_ls_number_reflns         5358
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.15793(19) 0.68068(18) -0.03507(14) 0.0317(6) Uani 1 1 d . . .
C7 C 0.26121(18) 0.68457(17) -0.00089(13) 0.0281(5) Uani 1 1 d . . .
C9 C 0.3016(2) 1.09616(18) 0.01580(14) 0.0345(6) Uani 1 1 d . . .
C10 C 0.1895(2) 1.11593(19) 0.00924(16) 0.0390(6) Uani 1 1 d . . .
C11 C 0.13356(19) 0.86038(17) -0.01169(14) 0.0306(5) Uani 1 1 d . . .
H11 H 0.0791 0.8744 0.0284 0.037 Uiso 1 1 calc R . .
C13 C 0.3397(2) 0.88683(18) -0.10432(14) 0.0334(6) Uani 1 1 d . . .
C14 C 0.25629(19) 0.89719(17) 0.10008(14) 0.0310(6) Uani 1 1 d . . .
C15 C 0.16104(19) 0.95344(19) -0.05557(15) 0.0350(6) Uani 1 1 d . . .
H15 H 0.1447 0.9456 -0.1097 0.042 Uiso 1 1 calc R . .
C16 C 0.1122(2) 0.58957(19) -0.04925(14) 0.0373(6) Uani 1 1 d . . .
H16 H 0.0417 0.5856 -0.0714 0.045 Uiso 1 1 calc R . .
C17 C 0.28461(19) 0.93563(17) -0.03854(14) 0.0300(5) Uani 1 1 d . . .
C18 C 0.25123(18) 0.85698(17) 0.02036(14) 0.0285(5) Uani 1 1 d . . .
C19 C 0.31851(19) 0.59983(18) 0.01518(14) 0.0358(6) Uani 1 1 d . . .
H19 H 0.3892 0.6030 0.0372 0.043 Uiso 1 1 calc R . .
C20 C 0.1670(2) 0.50580(19) -0.03183(15) 0.0415(7) Uani 1 1 d . . .
H20 H 0.1340 0.4443 -0.0406 0.050 Uiso 1 1 calc R . .
C21 C 0.1144(2) 1.0460(2) -0.02559(18) 0.0448(7) Uani 1 1 d . . .
C22 C 0.3707(2) 1.16103(19) 0.05052(16) 0.0438(7) Uani 1 1 d . . .
H22 H 0.4466 1.1467 0.0547 0.053 Uiso 1 1 calc R . .
C24 C 0.1503(2) 1.20309(19) 0.03902(17) 0.0493(8) Uani 1 1 d . . .
H24 H 0.0744 1.2177 0.0354 0.059 Uiso 1 1 calc R . .
C25 C 0.5014(2) 0.8724(2) -0.18464(15) 0.0389(6) Uani 1 1 d . . .
H25 H 0.4459 0.8516 -0.2223 0.047 Uiso 1 1 calc R . .
C26 C 0.5715(2) 0.9493(2) -0.21975(15) 0.0397(6) Uani 1 1 d . . .
C27 C 0.2717(2) 0.51132(19) -0.00110(15) 0.0403(6) Uani 1 1 d . . .
H27 H 0.3113 0.4532 0.0087 0.048 Uiso 1 1 calc R . .
C28 C 0.5645(3) 0.7822(2) -0.16064(18) 0.0549(8) Uani 1 1 d . . .
H28A H 0.6210 0.8007 -0.1246 0.082 Uiso 1 1 calc R . .
H28B H 0.5992 0.7523 -0.2041 0.082 Uiso 1 1 calc R . .
H28C H 0.5140 0.7356 -0.1378 0.082 Uiso 1 1 calc R . .
C29 C 0.10038(19) 0.7714(2) -0.05541(14) 0.0348(6) Uani 1 1 d . . .
C30 C 0.3546(2) 0.9052(2) 0.21884(15) 0.0431(7) Uani 1 1 d . . .
H30 H 0.3216 0.9717 0.2222 0.052 Uiso 1 1 calc R . .
C31 C 0.4743(3) 0.9138(3) 0.2378(2) 0.0772(12) Uani 1 1 d . . .
H31A H 0.5102 0.8508 0.2302 0.116 Uiso 1 1 calc R . .
H31B H 0.4822 0.9334 0.2898 0.116 Uiso 1 1 calc R . .
H31C H 0.5085 0.9627 0.2057 0.116 Uiso 1 1 calc R . .
C32 C 0.2929(2) 0.83984(19) 0.27076(15) 0.0428(7) Uani 1 1 d . . .
C33 C 0.6683(2) 0.9779(2) -0.18637(18) 0.0544(8) Uani 1 1 d . . .
H33 H 0.6911 0.9488 -0.1411 0.065 Uiso 1 1 calc R . .
C34 C 0.2189(3) 1.2680(2) 0.07336(19) 0.0592(9) Uani 1 1 d . . .
H34 H 0.1909 1.3272 0.0930 0.071 Uiso 1 1 calc R . .
C35 C 0.3227(3) 0.7437(2) 0.28395(19) 0.0664(10) Uani 1 1 d . . .
H35 H 0.3863 0.7178 0.2610 0.080 Uiso 1 1 calc R . .
C36 C 0.1984(2) 0.8732(2) 0.30616(15) 0.0459(7) Uani 1 1 d . . .
H36 H 0.1753 0.9384 0.2984 0.055 Uiso 1 1 calc R . .
C37 C 0.1376(3) 0.8134(3) 0.35229(17) 0.0697(10) Uani 1 1 d . . .
H37 H 0.0737 0.8382 0.3757 0.084 Uiso 1 1 calc R . .
C38 C 0.3299(3) 1.2466(2) 0.07916(19) 0.0571(8) Uani 1 1 d . . .
H38 H 0.3778 1.2912 0.1030 0.068 Uiso 1 1 calc R . .
C39 C 0.1678(4) 0.7210(3) 0.36438(19) 0.0842(13) Uani 1 1 d . . .
H39 H 0.1255 0.6807 0.3962 0.101 Uiso 1 1 calc R . .
C40 C 0.5406(3) 0.9921(3) -0.2864(2) 0.0876(14) Uani 1 1 d . . .
H40 H 0.4750 0.9726 -0.3105 0.105 Uiso 1 1 calc R . .
C41 C 0.7324(4) 1.0498(3) -0.2196(3) 0.109(2) Uani 1 1 d . . .
H41 H 0.7979 1.0708 -0.1960 0.131 Uiso 1 1 calc R . .
C42 C 0.2596(4) 0.6848(3) 0.3308(2) 0.0835(13) Uani 1 1 d . . .
H42 H 0.2807 0.6192 0.3393 0.100 Uiso 1 1 calc R . .
C45 C 0.7014(7) 1.0907(3) -0.2862(5) 0.157(4) Uani 1 1 d . . .
H45 H 0.7467 1.1375 -0.3100 0.189 Uiso 1 1 calc R . .
C46 C 0.6060(6) 1.0632(5) -0.3171(4) 0.154(4) Uani 1 1 d . . .
H46 H 0.5829 1.0939 -0.3617 0.185 Uiso 1 1 calc R . .
N1 N 0.44176(16) 0.91354(15) -0.12097(12) 0.0358(5) Uani 1 1 d . . .
H1 H 0.4745 0.9572 -0.0930 0.043 Uiso 1 1 calc R . .
N2 N 0.34217(17) 0.87074(17) 0.14131(11) 0.0373(5) Uani 1 1 d . . .
H2 H 0.3922 0.8321 0.1221 0.045 Uiso 1 1 calc R . .
O1 O 0.35090(13) 1.01345(12) -0.01199(10) 0.0342(4) Uani 1 1 d . . .
O2 O 0.01600(15) 1.06195(15) -0.03133(16) 0.0708(7) Uani 1 1 d . . .
O3 O 0.28760(14) 0.82527(15) -0.13925(10) 0.0443(5) Uani 1 1 d . . .
O4 O 0.31372(12) 0.77016(12) 0.01618(9) 0.0317(4) Uani 1 1 d . . .
O5 O 0.02590(14) 0.77440(14) -0.10030(11) 0.0415(5) Uani 1 1 d . . .
O6 O 0.18499(14) 0.95408(13) 0.12066(10) 0.0407(5) 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
C6 C16 1.395(3) . ?
C6 C7 1.404(3) . ?
C6 C29 1.478(4) . ?
C7 O4 1.375(3) . ?
C7 C19 1.389(3) . ?
C9 C22 1.378(4) . ?
C9 O1 1.380(3) . ?
C9 C10 1.400(4) . ?
C10 C24 1.397(4) . ?
C10 C21 1.469(4) . ?
C11 C29 1.509(4) . ?
C11 C15 1.540(4) . ?
C11 C18 1.549(3) . ?
C11 H11 1.0000 . ?
C13 O3 1.231(3) . ?
C13 N1 1.333(3) . ?
C13 C17 1.518(4) . ?
C14 O6 1.227(3) . ?
C14 N2 1.335(3) . ?
C14 C18 1.539(3) . ?
C15 C21 1.495(4) . ?
C15 C17 1.559(3) . ?
C15 H15 1.0000 . ?
C16 C20 1.368(4) . ?
C16 H16 0.9500 . ?
C17 O1 1.424(3) . ?
C17 C18 1.568(3) . ?
C18 O4 1.418(3) . ?
C19 C27 1.375(4) . ?
C19 H19 0.9500 . ?
C20 C27 1.395(4) . ?
C20 H20 0.9500 . ?
C21 O2 1.226(3) . ?
C22 C38 1.378(4) . ?
C22 H22 0.9500 . ?
C24 C34 1.372(4) . ?
C24 H24 0.9500 . ?
C25 N1 1.471(3) . ?
C25 C26 1.500(4) . ?
C25 C28 1.522(4) . ?
C25 H25 1.0000 . ?
C26 C33 1.383(4) . ?
C26 C40 1.389(4) . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 O5 1.217(3) . ?
C30 N2 1.482(3) . ?
C30 C32 1.500(4) . ?
C30 C31 1.505(4) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C35 1.391(4) . ?
C32 C36 1.395(4) . ?
C33 C41 1.395(5) . ?
C33 H33 0.9500 . ?
C34 C38 1.390(5) . ?
C34 H34 0.9500 . ?
C35 C42 1.400(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.384(4) . ?
C36 H36 0.9500 . ?
C37 C39 1.341(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C42 1.367(6) . ?
C39 H39 0.9500 . ?
C40 C46 1.378(7) . ?
C40 H40 0.9500 . ?
C41 C45 1.378(9) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C45 C46 1.345(11) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

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
C16 C6 C7 118.3(2) . . ?
C16 C6 C29 121.5(2) . . ?
C7 C6 C29 120.2(2) . . ?
O4 C7 C19 115.9(2) . . ?
O4 C7 C6 123.3(2) . . ?
C19 C7 C6 120.8(2) . . ?
C22 C9 O1 115.5(2) . . ?
C22 C9 C10 120.8(2) . . ?
O1 C9 C10 123.8(2) . . ?
C24 C10 C9 118.0(3) . . ?
C24 C10 C21 120.7(2) . . ?
C9 C10 C21 121.3(2) . . ?
C29 C11 C15 117.6(2) . . ?
C29 C11 C18 114.8(2) . . ?
C15 C11 C18 90.81(17) . . ?
C29 C11 H11 110.7 . . ?
C15 C11 H11 110.7 . . ?
C18 C11 H11 110.7 . . ?
O3 C13 N1 123.9(2) . . ?
O3 C13 C17 118.2(2) . . ?
N1 C13 C17 117.9(2) . . ?
O6 C14 N2 124.2(2) . . ?
O6 C14 C18 118.8(2) . . ?
N2 C14 C18 116.9(2) . . ?
C21 C15 C11 116.0(2) . . ?
C21 C15 C17 115.6(2) . . ?
C11 C15 C17 88.82(18) . . ?
C21 C15 H15 111.6 . . ?
C11 C15 H15 111.6 . . ?
C17 C15 H15 111.6 . . ?
C20 C16 C6 121.2(2) . . ?
C20 C16 H16 119.4 . . ?
C6 C16 H16 119.4 . . ?
O1 C17 C13 109.99(19) . . ?
O1 C17 C15 119.9(2) . . ?
C13 C17 C15 110.2(2) . . ?
O1 C17 C18 116.0(2) . . ?
C13 C17 C18 109.8(2) . . ?
C15 C17 C18 89.41(17) . . ?
O4 C18 C14 109.26(19) . . ?
O4 C18 C11 120.30(19) . . ?
C14 C18 C11 111.95(19) . . ?
O4 C18 C17 113.85(19) . . ?
C14 C18 C17 111.88(18) . . ?
C11 C18 C17 88.19(17) . . ?
C27 C19 C7 119.2(2) . . ?
C27 C19 H19 120.4 . . ?
C7 C19 H19 120.4 . . ?
C16 C20 C27 119.6(2) . . ?
C16 C20 H20 120.2 . . ?
C27 C20 H20 120.2 . . ?
O2 C21 C10 122.1(3) . . ?
O2 C21 C15 119.7(3) . . ?
C10 C21 C15 118.2(2) . . ?
C38 C22 C9 120.0(3) . . ?
C38 C22 H22 120.0 . . ?
C9 C22 H22 120.0 . . ?
C34 C24 C10 121.4(3) . . ?
C34 C24 H24 119.3 . . ?
C10 C24 H24 119.3 . . ?
N1 C25 C26 109.9(2) . . ?
N1 C25 C28 110.0(2) . . ?
C26 C25 C28 113.9(2) . . ?
N1 C25 H25 107.6 . . ?
C26 C25 H25 107.6 . . ?
C28 C25 H25 107.6 . . ?
C33 C26 C40 119.2(3) . . ?
C33 C26 C25 120.3(3) . . ?
C40 C26 C25 120.5(3) . . ?
C19 C27 C20 120.9(2) . . ?
C19 C27 H27 119.6 . . ?
C20 C27 H27 119.6 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5 C29 C6 123.2(2) . . ?
O5 C29 C11 121.3(2) . . ?
C6 C29 C11 115.3(2) . . ?
N2 C30 C32 110.1(2) . . ?
N2 C30 C31 109.8(2) . . ?
C32 C30 C31 113.2(3) . . ?
N2 C30 H30 107.9 . . ?
C32 C30 H30 107.9 . . ?
C31 C30 H30 107.9 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C35 C32 C36 116.8(3) . . ?
C35 C32 C30 123.0(3) . . ?
C36 C32 C30 120.2(3) . . ?
C26 C33 C41 119.6(4) . . ?
C26 C33 H33 120.2 . . ?
C41 C33 H33 120.2 . . ?
C24 C34 C38 119.4(3) . . ?
C24 C34 H34 120.3 . . ?
C38 C34 H34 120.3 . . ?
C32 C35 C42 120.5(4) . . ?
C32 C35 H35 119.7 . . ?
C42 C35 H35 119.7 . . ?
C37 C36 C32 121.5(3) . . ?
C37 C36 H36 119.3 . . ?
C32 C36 H36 119.3 . . ?
C39 C37 C36 120.9(4) . . ?
C39 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C22 C38 C34 120.4(3) . . ?
C22 C38 H38 119.8 . . ?
C34 C38 H38 119.8 . . ?
C37 C39 C42 119.9(4) . . ?
C37 C39 H39 120.1 . . ?
C42 C39 H39 120.1 . . ?
C46 C40 C26 119.3(5) . . ?
C46 C40 H40 120.3 . . ?
C26 C40 H40 120.3 . . ?
C45 C41 C33 120.5(5) . . ?
C45 C41 H41 119.7 . . ?
C33 C41 H41 119.7 . . ?
C39 C42 C35 120.5(4) . . ?
C39 C42 H42 119.8 . . ?
C35 C42 H42 119.8 . . ?
C46 C45 C41 118.9(5) . . ?
C46 C45 H45 120.5 . . ?
C41 C45 H45 120.5 . . ?
C45 C46 C40 122.4(5) . . ?
C45 C46 H46 118.8 . . ?
C40 C46 H46 118.8 . . ?
C13 N1 C25 122.2(2) . . ?
C13 N1 H1 118.9 . . ?
C25 N1 H1 118.9 . . ?
C14 N2 C30 121.1(2) . . ?
C14 N2 H2 119.4 . . ?
C30 N2 H2 119.4 . . ?
C9 O1 C17 119.49(18) . . ?
C7 O4 C18 118.75(17) . . ?

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
C16 C6 C7 O4 -179.5(2) . . . . ?
C29 C6 C7 O4 0.7(3) . . . . ?
C16 C6 C7 C19 3.0(3) . . . . ?
C29 C6 C7 C19 -176.8(2) . . . . ?
C22 C9 C10 C24 -0.1(4) . . . . ?
O1 C9 C10 C24 -179.1(2) . . . . ?
C22 C9 C10 C21 -178.1(3) . . . . ?
O1 C9 C10 C21 2.9(4) . . . . ?
C29 C11 C15 C21 135.9(2) . . . . ?
C18 C11 C15 C21 -105.4(2) . . . . ?
C29 C11 C15 C17 -106.0(2) . . . . ?
C18 C11 C15 C17 12.65(19) . . . . ?
C7 C6 C16 C20 -1.3(4) . . . . ?
C29 C6 C16 C20 178.5(2) . . . . ?
O3 C13 C17 O1 -171.8(2) . . . . ?
N1 C13 C17 O1 7.9(3) . . . . ?
O3 C13 C17 C15 -37.6(3) . . . . ?
N1 C13 C17 C15 142.2(2) . . . . ?
O3 C13 C17 C18 59.4(3) . . . . ?
N1 C13 C17 C18 -120.9(2) . . . . ?
C21 C15 C17 O1 -14.0(3) . . . . ?
C11 C15 C17 O1 -132.5(2) . . . . ?
C21 C15 C17 C13 -143.2(2) . . . . ?
C11 C15 C17 C13 98.4(2) . . . . ?
C21 C15 C17 C18 105.9(2) . . . . ?
C11 C15 C17 C18 -12.50(19) . . . . ?
O6 C14 C18 O4 -159.4(2) . . . . ?
N2 C14 C18 O4 23.7(3) . . . . ?
O6 C14 C18 C11 -23.6(3) . . . . ?
N2 C14 C18 C11 159.5(2) . . . . ?
O6 C14 C18 C17 73.6(3) . . . . ?
N2 C14 C18 C17 -103.3(2) . . . . ?
C29 C11 C18 O4 -8.2(3) . . . . ?
C15 C11 C18 O4 -129.3(2) . . . . ?
C29 C11 C18 C14 -138.6(2) . . . . ?
C15 C11 C18 C14 100.3(2) . . . . ?
C29 C11 C18 C17 108.5(2) . . . . ?
C15 C11 C18 C17 -12.58(19) . . . . ?
O1 C17 C18 O4 -101.7(2) . . . . ?
C13 C17 C18 O4 23.7(3) . . . . ?
C15 C17 C18 O4 135.0(2) . . . . ?
O1 C17 C18 C14 22.8(3) . . . . ?
C13 C17 C18 C14 148.20(19) . . . . ?
C15 C17 C18 C14 -100.5(2) . . . . ?
O1 C17 C18 C11 135.8(2) . . . . ?
C13 C17 C18 C11 -98.8(2) . . . . ?
C15 C17 C18 C11 12.43(19) . . . . ?
O4 C7 C19 C27 -179.3(2) . . . . ?
C6 C7 C19 C27 -1.6(4) . . . . ?
C6 C16 C20 C27 -1.7(4) . . . . ?
C24 C10 C21 O2 1.6(5) . . . . ?
C9 C10 C21 O2 179.5(3) . . . . ?
C24 C10 C21 C15 -179.2(3) . . . . ?
C9 C10 C21 C15 -1.3(4) . . . . ?
C11 C15 C21 O2 -72.2(4) . . . . ?
C17 C15 C21 O2 -174.2(3) . . . . ?
C11 C15 C21 C10 108.6(3) . . . . ?
C17 C15 C21 C10 6.6(4) . . . . ?
O1 C9 C22 C38 179.0(3) . . . . ?
C10 C9 C22 C38 -0.1(4) . . . . ?
C9 C10 C24 C34 0.4(4) . . . . ?
C21 C10 C24 C34 178.4(3) . . . . ?
N1 C25 C26 C33 76.0(3) . . . . ?
C28 C25 C26 C33 -47.9(3) . . . . ?
N1 C25 C26 C40 -104.5(3) . . . . ?
C28 C25 C26 C40 131.6(3) . . . . ?
C7 C19 C27 C20 -1.5(4) . . . . ?
C16 C20 C27 C19 3.1(4) . . . . ?
C16 C6 C29 O5 -18.4(4) . . . . ?
C7 C6 C29 O5 161.3(2) . . . . ?
C16 C6 C29 C11 156.5(2) . . . . ?
C7 C6 C29 C11 -23.7(3) . . . . ?
C15 C11 C29 O5 -53.9(3) . . . . ?
C18 C11 C29 O5 -158.9(2) . . . . ?
C15 C11 C29 C6 131.1(2) . . . . ?
C18 C11 C29 C6 26.1(3) . . . . ?
N2 C30 C32 C35 67.4(3) . . . . ?
C31 C30 C32 C35 -55.9(4) . . . . ?
N2 C30 C32 C36 -110.0(3) . . . . ?
C31 C30 C32 C36 126.8(3) . . . . ?
C40 C26 C33 C41 0.7(4) . . . . ?
C25 C26 C33 C41 -179.7(3) . . . . ?
C10 C24 C34 C38 -0.4(5) . . . . ?
C36 C32 C35 C42 -0.1(4) . . . . ?
C30 C32 C35 C42 -177.5(3) . . . . ?
C35 C32 C36 C37 0.2(4) . . . . ?
C30 C32 C36 C37 177.7(3) . . . . ?
C32 C36 C37 C39 -0.1(5) . . . . ?
C9 C22 C38 C34 0.1(5) . . . . ?
C24 C34 C38 C22 0.2(5) . . . . ?
C36 C37 C39 C42 -0.1(6) . . . . ?
C33 C26 C40 C46 -1.0(5) . . . . ?
C25 C26 C40 C46 179.4(3) . . . . ?
C26 C33 C41 C45 -1.7(5) . . . . ?
C37 C39 C42 C35 0.2(6) . . . . ?
C32 C35 C42 C39 -0.1(5) . . . . ?
C33 C41 C45 C46 2.9(7) . . . . ?
C41 C45 C46 C40 -3.3(9) . . . . ?
C26 C40 C46 C45 2.4(8) . . . . ?
O3 C13 N1 C25 1.3(4) . . . . ?
C17 C13 N1 C25 -178.5(2) . . . . ?
C26 C25 N1 C13 143.6(2) . . . . ?
C28 C25 N1 C13 -90.2(3) . . . . ?
O6 C14 N2 C30 3.4(4) . . . . ?
C18 C14 N2 C30 -179.8(2) . . . . ?
C32 C30 N2 C14 85.5(3) . . . . ?
C31 C30 N2 C14 -149.3(3) . . . . ?
C22 C9 O1 C17 170.5(2) . . . . ?
C10 C9 O1 C17 -10.5(3) . . . . ?
C13 C17 O1 C9 145.2(2) . . . . ?
C15 C17 O1 C9 16.0(3) . . . . ?
C18 C17 O1 C9 -89.5(3) . . . . ?
C19 C7 O4 C18 -163.3(2) . . . . ?
C6 C7 O4 C18 19.1(3) . . . . ?
C14 C18 O4 C7 117.0(2) . . . . ?
C11 C18 O4 C7 -14.5(3) . . . . ?
C17 C18 O4 C7 -117.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
_database_code_depnum_ccdc_archive 'CCDC 1010751'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_saka423_p212121

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Anti-HH photodimer of (R)-N-(1-phenylethyl)-2-chromonecarboxamide'
_chemical_name_common            ?
_chemical_melting_point          521-522
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H30 N2 O6'
_chemical_formula_weight         586.62
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   9.7337(10)
_cell_length_b                   13.9495(14)
_cell_length_c                   22.104(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3001.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    2088
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      19.63

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_T_max  0.9781
_exptl_absorpt_process_details   'SADABS Sheldrick 1997'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14333
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5287
_reflns_number_gt                4221
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0561P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(11)
_refine_ls_number_reflns         5287
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7659(2) 0.63514(17) 0.80456(10) 0.0246(6) Uani 1 1 d . . .
C2 C 0.7679(2) 0.74454(17) 0.81524(10) 0.0252(5) Uani 1 1 d . . .
H2 H 0.7148 0.7793 0.7833 0.030 Uiso 1 1 calc R . .
C3 C 0.7270(2) 0.77671(18) 0.87767(10) 0.0252(6) Uani 1 1 d . . .
C4 C 0.6433(3) 0.70973(18) 0.91285(11) 0.0284(6) Uani 1 1 d . . .
C5 C 0.5732(3) 0.7397(2) 0.96445(12) 0.0404(7) Uani 1 1 d . . .
H5 H 0.5791 0.8048 0.9768 0.048 Uiso 1 1 calc R . .
C6 C 0.4954(3) 0.6764(2) 0.99791(14) 0.0526(8) Uani 1 1 d . . .
H6 H 0.4482 0.6980 1.0330 0.063 Uiso 1 1 calc R . .
C7 C 0.4863(3) 0.5813(2) 0.98028(13) 0.0483(8) Uani 1 1 d . . .
H7 H 0.4322 0.5378 1.0032 0.058 Uiso 1 1 calc R . .
C8 C 0.5557(3) 0.5495(2) 0.92955(11) 0.0362(7) Uani 1 1 d . . .
H8 H 0.5501 0.4842 0.9178 0.043 Uiso 1 1 calc R . .
C9 C 0.6331(3) 0.61320(19) 0.89617(10) 0.0281(6) Uani 1 1 d . . .
C10 C 0.9268(2) 0.63491(17) 0.80623(10) 0.0241(6) Uani 1 1 d . . .
C11 C 0.9244(2) 0.74510(17) 0.80137(10) 0.0253(6) Uani 1 1 d . . .
H11 H 0.9778 0.7756 0.8349 0.030 Uiso 1 1 calc R . .
C12 C 0.9639(3) 0.78584(18) 0.74104(11) 0.0292(6) Uani 1 1 d . . .
C13 C 1.0406(3) 0.72333(18) 0.70052(11) 0.0287(6) Uani 1 1 d . . .
C14 C 1.1055(3) 0.7604(2) 0.64884(11) 0.0386(7) Uani 1 1 d . . .
H14 H 1.1026 0.8273 0.6412 0.046 Uiso 1 1 calc R . .
C15 C 1.1730(3) 0.7012(2) 0.60930(13) 0.0472(8) Uani 1 1 d . . .
H15 H 1.2161 0.7271 0.5744 0.057 Uiso 1 1 calc R . .
C16 C 1.1782(3) 0.6032(2) 0.62048(12) 0.0437(8) Uani 1 1 d . . .
H16 H 1.2245 0.5624 0.5928 0.052 Uiso 1 1 calc R . .
C17 C 1.1170(3) 0.5644(2) 0.67123(11) 0.0328(6) Uani 1 1 d . . .
H17 H 1.1206 0.4974 0.6786 0.039 Uiso 1 1 calc R . .
C18 C 1.0502(2) 0.62517(18) 0.71120(10) 0.0245(6) Uani 1 1 d . . .
C19 C 0.9785(2) 0.60085(17) 0.86822(10) 0.0245(5) Uani 1 1 d . . .
C20 C 1.1031(3) 0.47701(19) 0.92518(11) 0.0325(6) Uani 1 1 d . . .
H20 H 1.1384 0.5339 0.9479 0.039 Uiso 1 1 calc R . .
C21 C 1.2276(3) 0.4190(2) 0.90491(13) 0.0463(8) Uani 1 1 d . . .
H21A H 1.2842 0.4579 0.8777 0.069 Uiso 1 1 calc R . .
H21B H 1.1967 0.3612 0.8837 0.069 Uiso 1 1 calc R . .
H21C H 1.2820 0.4006 0.9404 0.069 Uiso 1 1 calc R . .
C22 C 1.0063(3) 0.42306(19) 0.96740(11) 0.0333(6) Uani 1 1 d . . .
C23 C 1.0465(3) 0.3398(2) 0.99673(12) 0.0443(7) Uani 1 1 d . . .
H23 H 1.1338 0.3126 0.9880 0.053 Uiso 1 1 calc R . .
C24 C 0.9614(4) 0.2956(2) 1.03860(13) 0.0546(9) Uani 1 1 d . . .
H24 H 0.9909 0.2385 1.0581 0.065 Uiso 1 1 calc R . .
C25 C 0.8352(4) 0.3334(2) 1.05199(12) 0.0500(8) Uani 1 1 d . . .
H25 H 0.7779 0.3039 1.0814 0.060 Uiso 1 1 calc R . .
C26 C 0.7929(4) 0.4145(2) 1.02239(13) 0.0542(8) Uani 1 1 d . . .
H26 H 0.7042 0.4401 1.0302 0.065 Uiso 1 1 calc R . .
C27 C 0.8786(3) 0.4594(2) 0.98107(13) 0.0485(8) Uani 1 1 d . . .
H27 H 0.8484 0.5165 0.9618 0.058 Uiso 1 1 calc R . .
C28 C 0.7171(3) 0.60673(18) 0.74109(11) 0.0272(6) Uani 1 1 d . . .
C29 C 0.6370(3) 0.47264(19) 0.67798(11) 0.0347(7) Uani 1 1 d . . .
H29 H 0.7060 0.4944 0.6474 0.042 Uiso 1 1 calc R . .
C30 C 0.4962(3) 0.5019(2) 0.65635(13) 0.0474(8) Uani 1 1 d . . .
H30A H 0.4930 0.5717 0.6514 0.071 Uiso 1 1 calc R . .
H30B H 0.4272 0.4821 0.6861 0.071 Uiso 1 1 calc R . .
H30C H 0.4769 0.4710 0.6175 0.071 Uiso 1 1 calc R . .
C31 C 0.6481(3) 0.3645(2) 0.68408(12) 0.0360(7) Uani 1 1 d . . .
C32 C 0.5949(3) 0.3159(2) 0.73317(14) 0.0457(8) Uani 1 1 d . . .
H32 H 0.5521 0.3509 0.7649 0.055 Uiso 1 1 calc R . .
C33 C 0.6031(4) 0.2169(2) 0.73694(17) 0.0606(10) Uani 1 1 d . . .
H33 H 0.5667 0.1847 0.7712 0.073 Uiso 1 1 calc R . .
C34 C 0.6635(4) 0.1652(3) 0.6913(2) 0.0700(12) Uani 1 1 d . . .
H34 H 0.6701 0.0975 0.6943 0.084 Uiso 1 1 calc R . .
C35 C 0.7140(4) 0.2116(3) 0.6418(2) 0.0672(11) Uani 1 1 d . . .
H35 H 0.7532 0.1757 0.6097 0.081 Uiso 1 1 calc R . .
C36 C 0.7085(3) 0.3113(2) 0.63800(15) 0.0517(8) Uani 1 1 d . . .
H36 H 0.7463 0.3430 0.6038 0.062 Uiso 1 1 calc R . .
N1 N 0.6707(2) 0.51736(15) 0.73624(9) 0.0323(5) Uani 1 1 d . . .
H1 H 0.6597 0.4835 0.7695 0.039 Uiso 1 1 calc R . .
N2 N 1.0344(2) 0.51321(14) 0.87065(9) 0.0264(5) Uani 1 1 d . . .
H2A H 1.0298 0.4761 0.8385 0.032 Uiso 1 1 calc R . .
O1 O 0.99078(18) 0.57997(11) 0.76009(7) 0.0278(4) Uani 1 1 d . . .
O2 O 0.70289(18) 0.57376(12) 0.84794(7) 0.0287(4) Uani 1 1 d . . .
O3 O 0.9330(2) 0.86862(13) 0.72849(8) 0.0418(5) Uani 1 1 d . . .
O4 O 0.75839(18) 0.85632(12) 0.89561(7) 0.0347(4) Uani 1 1 d . . .
O5 O 0.73069(19) 0.66337(13) 0.69913(7) 0.0366(5) Uani 1 1 d . . .
O6 O 0.96346(18) 0.65342(12) 0.91181(7) 0.0314(4) 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 O2 1.424(3) . ?
C1 C28 1.533(3) . ?
C1 C2 1.544(3) . ?
C1 C10 1.567(3) . ?
C2 C3 1.505(3) . ?
C2 C11 1.554(3) . ?
C2 H2 1.0000 . ?
C3 O4 1.218(3) . ?
C3 C4 1.463(4) . ?
C4 C5 1.393(3) . ?
C4 C9 1.400(3) . ?
C5 C6 1.378(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.379(3) . ?
C10 O1 1.420(3) . ?
C10 C19 1.535(3) . ?
C10 C11 1.541(3) . ?
C11 C12 1.500(3) . ?
C11 H11 1.0000 . ?
C12 O3 1.225(3) . ?
C12 C13 1.456(3) . ?
C13 C18 1.393(3) . ?
C13 C14 1.404(3) . ?
C14 C15 1.370(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 O1 1.379(3) . ?
C19 O6 1.220(3) . ?
C19 N2 1.340(3) . ?
C20 N2 1.468(3) . ?
C20 C22 1.525(4) . ?
C20 C21 1.525(4) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.377(4) . ?
C22 C23 1.386(4) . ?
C23 C24 1.387(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.370(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 O5 1.226(3) . ?
C28 N1 1.330(3) . ?
C29 N1 1.468(3) . ?
C29 C30 1.508(4) . ?
C29 C31 1.518(4) . ?
C29 H29 1.0000 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.380(4) . ?
C31 C36 1.391(4) . ?
C32 C33 1.386(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.372(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.363(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.395(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?

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
O2 C1 C28 109.10(19) . . ?
O2 C1 C2 119.77(19) . . ?
C28 C1 C2 113.5(2) . . ?
O2 C1 C10 114.41(19) . . ?
C28 C1 C10 109.31(19) . . ?
C2 C1 C10 89.19(18) . . ?
C3 C2 C1 115.6(2) . . ?
C3 C2 C11 116.0(2) . . ?
C1 C2 C11 89.27(18) . . ?
C3 C2 H2 111.4 . . ?
C1 C2 H2 111.4 . . ?
C11 C2 H2 111.4 . . ?
O4 C3 C4 123.3(2) . . ?
O4 C3 C2 120.3(2) . . ?
C4 C3 C2 116.4(2) . . ?
C5 C4 C9 118.0(2) . . ?
C5 C4 C3 121.1(2) . . ?
C9 C4 C3 120.9(2) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.3(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 O2 115.2(2) . . ?
C8 C9 C4 121.2(2) . . ?
O2 C9 C4 123.5(2) . . ?
O1 C10 C19 109.29(19) . . ?
O1 C10 C11 119.67(19) . . ?
C19 C10 C11 112.1(2) . . ?
O1 C10 C1 115.01(19) . . ?
C19 C10 C1 110.45(19) . . ?
C11 C10 C1 88.93(18) . . ?
C12 C11 C10 115.9(2) . . ?
C12 C11 C2 115.4(2) . . ?
C10 C11 C2 89.77(19) . . ?
C12 C11 H11 111.4 . . ?
C10 C11 H11 111.4 . . ?
C2 C11 H11 111.4 . . ?
O3 C12 C13 123.4(2) . . ?
O3 C12 C11 119.7(2) . . ?
C13 C12 C11 116.8(2) . . ?
C18 C13 C14 118.0(2) . . ?
C18 C13 C12 121.3(2) . . ?
C14 C13 C12 120.7(2) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 121.0(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 118.7(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
O1 C18 C17 114.6(2) . . ?
O1 C18 C13 123.7(2) . . ?
C17 C18 C13 121.6(2) . . ?
O6 C19 N2 124.5(2) . . ?
O6 C19 C10 118.7(2) . . ?
N2 C19 C10 116.8(2) . . ?
N2 C20 C22 113.0(2) . . ?
N2 C20 C21 107.7(2) . . ?
C22 C20 C21 114.2(2) . . ?
N2 C20 H20 107.2 . . ?
C22 C20 H20 107.2 . . ?
C21 C20 H20 107.2 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 117.4(3) . . ?
C27 C22 C20 120.7(2) . . ?
C23 C22 C20 121.7(3) . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 119.0(3) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 121.5(3) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
O5 C28 N1 125.4(2) . . ?
O5 C28 C1 119.5(2) . . ?
N1 C28 C1 114.9(2) . . ?
N1 C29 C30 111.5(2) . . ?
N1 C29 C31 109.2(2) . . ?
C30 C29 C31 111.2(2) . . ?
N1 C29 H29 108.3 . . ?
C30 C29 H29 108.3 . . ?
C31 C29 H29 108.3 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C36 118.2(3) . . ?
C32 C31 C29 122.1(2) . . ?
C36 C31 C29 119.7(3) . . ?
C31 C32 C33 121.0(3) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C34 C33 C32 120.3(4) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 119.7(3) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 120.5(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 120.3(4) . . ?
C31 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
C28 N1 C29 123.0(2) . . ?
C28 N1 H1 118.5 . . ?
C29 N1 H1 118.5 . . ?
C19 N2 C20 122.1(2) . . ?
C19 N2 H2A 118.9 . . ?
C20 N2 H2A 118.9 . . ?
C18 O1 C10 120.03(18) . . ?
C9 O2 C1 119.53(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
O2 C1 C2 C3 11.8(3) . . . . ?
C28 C1 C2 C3 143.2(2) . . . . ?
C10 C1 C2 C3 -106.1(2) . . . . ?
O2 C1 C2 C11 130.5(2) . . . . ?
C28 C1 C2 C11 -98.1(2) . . . . ?
C10 C1 C2 C11 12.64(18) . . . . ?
C1 C2 C3 O4 160.9(2) . . . . ?
C11 C2 C3 O4 58.3(3) . . . . ?
C1 C2 C3 C4 -22.2(3) . . . . ?
C11 C2 C3 C4 -124.7(2) . . . . ?
O4 C3 C4 C5 12.0(4) . . . . ?
C2 C3 C4 C5 -164.8(2) . . . . ?
O4 C3 C4 C9 -167.0(2) . . . . ?
C2 C3 C4 C9 16.2(3) . . . . ?
C9 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C6 -179.4(3) . . . . ?
C4 C5 C6 C7 0.0(5) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C7 C8 C9 O2 177.4(2) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C5 C4 C9 C8 0.2(4) . . . . ?
C3 C4 C9 C8 179.2(2) . . . . ?
C5 C4 C9 O2 -176.7(2) . . . . ?
C3 C4 C9 O2 2.4(4) . . . . ?
O2 C1 C10 O1 102.1(2) . . . . ?
C28 C1 C10 O1 -20.6(3) . . . . ?
C2 C1 C10 O1 -135.27(19) . . . . ?
O2 C1 C10 C19 -22.2(3) . . . . ?
C28 C1 C10 C19 -144.82(19) . . . . ?
C2 C1 C10 C19 100.5(2) . . . . ?
O2 C1 C10 C11 -135.36(19) . . . . ?
C28 C1 C10 C11 102.0(2) . . . . ?
C2 C1 C10 C11 -12.75(18) . . . . ?
O1 C10 C11 C12 12.8(3) . . . . ?
C19 C10 C11 C12 142.7(2) . . . . ?
C1 C10 C11 C12 -105.6(2) . . . . ?
O1 C10 C11 C2 131.1(2) . . . . ?
C19 C10 C11 C2 -99.0(2) . . . . ?
C1 C10 C11 C2 12.67(18) . . . . ?
C3 C2 C11 C12 -135.8(2) . . . . ?
C1 C2 C11 C12 105.9(2) . . . . ?
C3 C2 C11 C10 105.4(2) . . . . ?
C1 C2 C11 C10 -12.85(18) . . . . ?
C10 C11 C12 O3 162.1(2) . . . . ?
C2 C11 C12 O3 59.1(3) . . . . ?
C10 C11 C12 C13 -19.1(3) . . . . ?
C2 C11 C12 C13 -122.1(2) . . . . ?
O3 C12 C13 C18 -167.3(3) . . . . ?
C11 C12 C13 C18 13.9(4) . . . . ?
O3 C12 C13 C14 11.7(4) . . . . ?
C11 C12 C13 C14 -167.1(2) . . . . ?
C18 C13 C14 C15 1.7(4) . . . . ?
C12 C13 C14 C15 -177.3(3) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 O1 179.2(2) . . . . ?
C16 C17 C18 C13 1.7(4) . . . . ?
C14 C13 C18 O1 -179.7(2) . . . . ?
C12 C13 C18 O1 -0.7(4) . . . . ?
C14 C13 C18 C17 -2.4(4) . . . . ?
C12 C13 C18 C17 176.6(2) . . . . ?
O1 C10 C19 O6 161.7(2) . . . . ?
C11 C10 C19 O6 26.6(3) . . . . ?
C1 C10 C19 O6 -70.8(3) . . . . ?
O1 C10 C19 N2 -20.0(3) . . . . ?
C11 C10 C19 N2 -155.0(2) . . . . ?
C1 C10 C19 N2 107.5(2) . . . . ?
N2 C20 C22 C27 -45.2(3) . . . . ?
C21 C20 C22 C27 -168.7(3) . . . . ?
N2 C20 C22 C23 139.5(2) . . . . ?
C21 C20 C22 C23 16.0(4) . . . . ?
C27 C22 C23 C24 -0.6(4) . . . . ?
C20 C22 C23 C24 174.9(3) . . . . ?
C22 C23 C24 C25 -0.1(5) . . . . ?
C23 C24 C25 C26 1.5(5) . . . . ?
C24 C25 C26 C27 -2.3(5) . . . . ?
C23 C22 C27 C26 -0.2(4) . . . . ?
C20 C22 C27 C26 -175.7(3) . . . . ?
C25 C26 C27 C22 1.7(5) . . . . ?
O2 C1 C28 O5 162.0(2) . . . . ?
C2 C1 C28 O5 25.7(3) . . . . ?
C10 C1 C28 O5 -72.2(3) . . . . ?
O2 C1 C28 N1 -22.3(3) . . . . ?
C2 C1 C28 N1 -158.7(2) . . . . ?
C10 C1 C28 N1 103.5(2) . . . . ?
N1 C29 C31 C32 44.4(3) . . . . ?
C30 C29 C31 C32 -79.0(3) . . . . ?
N1 C29 C31 C36 -138.2(3) . . . . ?
C30 C29 C31 C36 98.4(3) . . . . ?
C36 C31 C32 C33 0.8(4) . . . . ?
C29 C31 C32 C33 178.3(3) . . . . ?
C31 C32 C33 C34 -0.6(5) . . . . ?
C32 C33 C34 C35 -0.9(5) . . . . ?
C33 C34 C35 C36 2.0(5) . . . . ?
C32 C31 C36 C35 0.3(4) . . . . ?
C29 C31 C36 C35 -177.2(3) . . . . ?
C34 C35 C36 C31 -1.7(5) . . . . ?
O5 C28 N1 C29 3.9(4) . . . . ?
C1 C28 N1 C29 -171.5(2) . . . . ?
C30 C29 N1 C28 -81.2(3) . . . . ?
C31 C29 N1 C28 155.5(2) . . . . ?
O6 C19 N2 C20 -9.6(4) . . . . ?
C10 C19 N2 C20 172.2(2) . . . . ?
C22 C20 N2 C19 91.2(3) . . . . ?
C21 C20 N2 C19 -141.8(2) . . . . ?
C17 C18 O1 C10 176.1(2) . . . . ?
C13 C18 O1 C10 -6.5(3) . . . . ?
C19 C10 O1 C18 -131.2(2) . . . . ?
C11 C10 O1 C18 -0.1(3) . . . . ?
C1 C10 O1 C18 103.9(2) . . . . ?
C8 C9 O2 C1 169.1(2) . . . . ?
C4 C9 O2 C1 -13.9(3) . . . . ?
C28 C1 O2 C9 -127.2(2) . . . . ?
C2 C1 O2 C9 6.1(3) . . . . ?
C10 C1 O2 C9 110.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.057
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
_database_code_depnum_ccdc_archive 'CCDC 1010752'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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data_saka493_P212121_a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Anti-HH photodimer of (R)-N-(1-t-butylethyl)-2-chromonecarboxamide'
_chemical_name_common            ?
_chemical_melting_point          531-532
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H38 N2 O6'
_chemical_formula_weight         546.64

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.704(18)
_cell_length_b                   14.23(3)
_cell_length_c                   26.50(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2906(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(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    1.249
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(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            13455
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.537
_diffrn_reflns_theta_max         25.614
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5433
_reflns_number_gt                3321
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.986

_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-2013 (Sheldrick, 2013)'
_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)+(0.1030P)²] 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       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1016 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.6(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5433
_refine_ls_number_parameters     370
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1907
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      0.997
_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 0.7861(7) 1.0241(3) 0.85605(18) 0.0300(11) Uani 1 1 d . U . . .
C2 C 0.9612(7) 1.0653(3) 0.87070(19) 0.0330(11) Uani 1 1 d . U . . .
H2 H 1.0011 1.1130 0.8455 0.040 Uiso 1 1 calc R U . . .
C3 C 1.0964(7) 0.9956(4) 0.8808(2) 0.0363(12) Uani 1 1 d . U . . .
C4 C 1.0797(8) 0.9103(4) 0.8508(2) 0.0411(13) Uani 1 1 d . U . . .
C5 C 1.2242(9) 0.8595(4) 0.8371(3) 0.0577(17) Uani 1 1 d . U . . .
H5 H 1.3352 0.8776 0.8493 0.069 Uiso 1 1 calc R U . . .
C6 C 1.2091(12) 0.7833(5) 0.8060(3) 0.075(2) Uani 1 1 d . U . . .
H6 H 1.3085 0.7473 0.7972 0.089 Uiso 1 1 calc R U . . .
C7 C 1.0520(13) 0.7600(5) 0.7881(3) 0.075(2) Uani 1 1 d . U . . .
H7 H 1.0423 0.7090 0.7651 0.090 Uiso 1 1 calc R U . . .
C8 C 0.9075(10) 0.8070(4) 0.8018(2) 0.0559(17) Uani 1 1 d . U . . .
H8 H 0.7965 0.7874 0.7902 0.067 Uiso 1 1 calc R U . . .
C9 C 0.9242(8) 0.8829(4) 0.8325(2) 0.0391(13) Uani 1 1 d . U . . .
C10 C 0.7161(6) 1.0534(3) 0.90816(18) 0.0258(10) Uani 1 1 d . U . . .
C11 C 0.8776(7) 1.1121(3) 0.9162(2) 0.0311(12) Uani 1 1 d . U . . .
H11 H 0.9382 1.0938 0.9481 0.037 Uiso 1 1 calc R U . . .
C12 C 0.8528(7) 1.2150(4) 0.9136(2) 0.0372(13) Uani 1 1 d . U . . .
C13 C 0.6817(7) 1.2478(4) 0.9256(2) 0.0349(12) Uani 1 1 d . U . . .
C14 C 0.6532(8) 1.3391(4) 0.9400(2) 0.0419(14) Uani 1 1 d . U . . .
H14 H 0.7486 1.3812 0.9420 0.050 Uiso 1 1 calc R U . . .
C15 C 0.4920(8) 1.3703(4) 0.9514(2) 0.0409(14) Uani 1 1 d . U . . .
H15 H 0.4744 1.4333 0.9622 0.049 Uiso 1 1 calc R U . . .
C16 C 0.3568(8) 1.3106(4) 0.9471(2) 0.0446(15) Uani 1 1 d . U . . .
H16 H 0.2431 1.3324 0.9546 0.054 Uiso 1 1 calc R U . . .
C17 C 0.3800(7) 1.2192(4) 0.9323(2) 0.0387(14) Uani 1 1 d . U . . .
H17 H 0.2833 1.1782 0.9291 0.046 Uiso 1 1 calc R U . . .
C18 C 0.5416(7) 1.1882(3) 0.92226(18) 0.0272(11) Uani 1 1 d . U . . .
C19 C 0.6989(8) 1.0779(4) 0.81428(19) 0.0388(13) Uani 1 1 d . U . . .
C20 C 0.4952(10) 1.0662(6) 0.7449(3) 0.078(2) Uani 1 1 d . U . . .
H20 H 0.5413 1.1307 0.7383 0.093 Uiso 1 1 calc R U . . .
C21 C 0.3136(12) 1.0764(9) 0.7601(5) 0.160(6) Uani 1 1 d . U . . .
H21A H 0.2671 1.0149 0.7698 0.239 Uiso 1 1 calc R U . . .
H21B H 0.2460 1.1015 0.7318 0.239 Uiso 1 1 calc R U . . .
H21C H 0.3059 1.1195 0.7889 0.239 Uiso 1 1 calc R U . . .
C22 C 0.5358(18) 1.0043(7) 0.6965(3) 0.115(3) Uani 1 1 d . U . . .
C23 C 0.7247(19) 1.0025(7) 0.6889(4) 0.134(4) Uani 1 1 d . U . . .
H23A H 0.7809 0.9751 0.7186 0.201 Uiso 1 1 calc R U . . .
H23B H 0.7673 1.0667 0.6838 0.201 Uiso 1 1 calc R U . . .
H23C H 0.7520 0.9645 0.6590 0.201 Uiso 1 1 calc R U . . .
C24 C 0.468(2) 0.9047(8) 0.7026(4) 0.188(7) Uani 1 1 d . U . . .
H24A H 0.4762 0.8715 0.6703 0.282 Uiso 1 1 calc R U . . .
H24B H 0.3464 0.9066 0.7135 0.282 Uiso 1 1 calc R U . . .
H24C H 0.5374 0.8716 0.7280 0.282 Uiso 1 1 calc R U . . .
C25 C 0.439(2) 1.0540(10) 0.6540(4) 0.205(7) Uani 1 1 d . U . . .
H25A H 0.4905 1.1161 0.6483 0.307 Uiso 1 1 calc R U . . .
H25B H 0.3166 1.0614 0.6634 0.307 Uiso 1 1 calc R U . . .
H25C H 0.4472 1.0166 0.6231 0.307 Uiso 1 1 calc R U . . .
C26 C 0.7110(7) 0.9698(3) 0.94311(18) 0.0279(11) Uani 1 1 d . U . . .
C27 C 0.5284(7) 0.8565(3) 0.9854(2) 0.0341(12) Uani 1 1 d . U . . .
H27 H 0.6453 0.8313 0.9946 0.041 Uiso 1 1 calc R U . . .
C28 C 0.4374(8) 0.7818(4) 0.9551(2) 0.0427(14) Uani 1 1 d . U . . .
H28A H 0.3215 0.8040 0.9457 0.064 Uiso 1 1 calc R U . . .
H28B H 0.4268 0.7246 0.9755 0.064 Uiso 1 1 calc R U . . .
H28C H 0.5046 0.7682 0.9246 0.064 Uiso 1 1 calc R U . . .
C29 C 0.4385(8) 0.8842(4) 1.0341(2) 0.0385(13) Uani 1 1 d . U . . .
C30 C 0.5384(10) 0.9633(4) 1.0591(2) 0.0592(18) Uani 1 1 d . U . . .
H30A H 0.4806 0.9810 1.0906 0.089 Uiso 1 1 calc R U . . .
H30B H 0.5424 1.0176 1.0364 0.089 Uiso 1 1 calc R U . . .
H30C H 0.6569 0.9422 1.0664 0.089 Uiso 1 1 calc R U . . .
C31 C 0.2545(8) 0.9158(4) 1.0245(2) 0.0504(15) Uani 1 1 d . U . . .
H31A H 0.2014 0.9359 1.0563 0.076 Uiso 1 1 calc R U . . .
H31B H 0.1876 0.8636 1.0102 0.076 Uiso 1 1 calc R U . . .
H31C H 0.2550 0.9685 1.0007 0.076 Uiso 1 1 calc R U . . .
C32 C 0.4395(9) 0.8012(4) 1.0692(2) 0.0540(17) Uani 1 1 d . U . . .
H32A H 0.5594 0.7864 1.0788 0.081 Uiso 1 1 calc R U . . .
H32B H 0.3876 0.7469 1.0523 0.081 Uiso 1 1 calc R U . . .
H32C H 0.3723 0.8162 1.0996 0.081 Uiso 1 1 calc R U . . .
N1 N 0.5919(7) 1.0284(4) 0.78639(17) 0.0469(13) Uani 1 1 d . U . . .
H1 H 0.5787 0.9684 0.7936 0.056 Uiso 1 1 calc R U . . .
N2 N 0.5558(5) 0.9371(3) 0.95352(15) 0.0313(10) Uani 1 1 d . U . . .
H2A H 0.4649 0.9656 0.9405 0.038 Uiso 1 1 calc R U . . .
O1 O 0.7742(5) 0.9267(2) 0.84647(13) 0.0381(9) Uani 1 1 d . U . . .
O2 O 1.2134(5) 1.0098(3) 0.90899(17) 0.0481(10) Uani 1 1 d . U . . .
O3 O 0.5552(4) 1.0978(2) 0.90630(13) 0.0286(8) Uani 1 1 d . U . . .
O4 O 0.9719(5) 1.2670(3) 0.9047(2) 0.0670(15) Uani 1 1 d . U . . .
O5 O 0.7266(6) 1.1610(3) 0.80923(15) 0.0511(11) Uani 1 1 d . U . . .
O6 O 0.8453(4) 0.9370(3) 0.95744(14) 0.0371(9) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.413(6) . ?
C1 C19 1.504(8) . ?
C1 C2 1.521(8) . ?
C1 C10 1.540(7) . ?
C2 C3 1.464(8) . ?
C2 C11 1.520(8) . ?
C2 H2 1.0000 . ?
C3 O2 1.188(7) . ?
C3 C4 1.457(8) . ?
C4 C9 1.350(9) . ?
C4 C5 1.376(8) . ?
C5 C6 1.368(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.342(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.349(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.359(8) . ?
C8 H8 0.9500 . ?
C9 O1 1.364(7) . ?
C10 O3 1.393(6) . ?
C10 C26 1.508(7) . ?
C10 C11 1.514(7) . ?
C11 C12 1.478(8) . ?
C11 H11 1.0000 . ?
C12 O4 1.203(7) . ?
C12 C13 1.434(8) . ?
C13 C14 1.372(8) . ?
C13 C18 1.376(7) . ?
C14 C15 1.353(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.349(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.348(8) . ?
C17 H17 0.9500 . ?
C18 O3 1.357(6) . ?
C19 O5 1.210(7) . ?
C19 N1 1.312(8) . ?
C20 N1 1.433(8) . ?
C20 C21 1.464(13) . ?
C20 C22 1.588(14) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.470(16) . ?
C22 C24 1.521(13) . ?
C22 C25 1.525(15) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O6 1.197(6) . ?
C26 N2 1.312(7) . ?
C27 N2 1.440(7) . ?
C27 C28 1.504(8) . ?
C27 C29 1.518(8) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C32 1.504(8) . ?
C29 C31 1.509(9) . ?
C29 C30 1.515(9) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C19 109.8(4) . . ?
O1 C1 C2 118.8(4) . . ?
C19 C1 C2 112.8(4) . . ?
O1 C1 C10 113.8(4) . . ?
C19 C1 C10 111.5(4) . . ?
C2 C1 C10 88.7(4) . . ?
C3 C2 C11 117.0(5) . . ?
C3 C2 C1 114.6(4) . . ?
C11 C2 C1 89.7(4) . . ?
C3 C2 H2 111.3 . . ?
C11 C2 H2 111.3 . . ?
C1 C2 H2 111.3 . . ?
O2 C3 C4 123.6(5) . . ?
O2 C3 C2 122.6(5) . . ?
C4 C3 C2 113.7(5) . . ?
C9 C4 C5 118.2(6) . . ?
C9 C4 C3 121.0(5) . . ?
C5 C4 C3 120.6(6) . . ?
C6 C5 C4 120.4(7) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.1(7) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 121.7(7) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 118.6(7) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C4 C9 C8 121.9(6) . . ?
C4 C9 O1 121.5(5) . . ?
C8 C9 O1 116.5(6) . . ?
O3 C10 C26 110.9(4) . . ?
O3 C10 C11 119.1(4) . . ?
C26 C10 C11 111.8(4) . . ?
O3 C10 C1 113.8(4) . . ?
C26 C10 C1 110.3(4) . . ?
C11 C10 C1 89.3(4) . . ?
C12 C11 C10 115.7(4) . . ?
C12 C11 C2 116.9(5) . . ?
C10 C11 C2 89.7(4) . . ?
C12 C11 H11 111.0 . . ?
C10 C11 H11 111.0 . . ?
C2 C11 H11 111.0 . . ?
O4 C12 C13 123.0(5) . . ?
O4 C12 C11 121.4(5) . . ?
C13 C12 C11 115.6(5) . . ?
C14 C13 C18 118.5(5) . . ?
C14 C13 C12 121.2(5) . . ?
C18 C13 C12 120.4(5) . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 118.9(5) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 121.4(6) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 119.2(5) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 O3 116.3(5) . . ?
C17 C18 C13 120.7(5) . . ?
O3 C18 C13 122.9(5) . . ?
O5 C19 N1 125.0(5) . . ?
O5 C19 C1 120.0(5) . . ?
N1 C19 C1 115.0(5) . . ?
N1 C20 C21 108.8(7) . . ?
N1 C20 C22 108.0(8) . . ?
C21 C20 C22 117.7(9) . . ?
N1 C20 H20 107.3 . . ?
C21 C20 H20 107.3 . . ?
C22 C20 H20 107.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C24 109.8(12) . . ?
C23 C22 C25 113.0(11) . . ?
C24 C22 C25 110.1(9) . . ?
C23 C22 C20 108.4(7) . . ?
C24 C22 C20 111.3(9) . . ?
C25 C22 C20 104.1(11) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O6 C26 N2 125.7(5) . . ?
O6 C26 C10 118.7(5) . . ?
N2 C26 C10 115.6(4) . . ?
N2 C27 C28 108.6(5) . . ?
N2 C27 C29 111.0(4) . . ?
C28 C27 C29 115.1(5) . . ?
N2 C27 H27 107.2 . . ?
C28 C27 H27 107.2 . . ?
C29 C27 H27 107.2 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 C29 C31 110.1(5) . . ?
C32 C29 C30 108.0(5) . . ?
C31 C29 C30 109.3(5) . . ?
C32 C29 C27 108.7(5) . . ?
C31 C29 C27 111.2(5) . . ?
C30 C29 C27 109.5(5) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C19 N1 C20 123.8(6) . . ?
C19 N1 H1 118.1 . . ?
C20 N1 H1 118.1 . . ?
C26 N2 C27 122.6(4) . . ?
C26 N2 H2A 118.7 . . ?
C27 N2 H2A 118.7 . . ?
C9 O1 C1 116.2(4) . . ?
C18 O3 C10 119.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -8.8(7) . . . . ?
C19 C1 C2 C3 -139.4(5) . . . . ?
C10 C1 C2 C3 107.8(5) . . . . ?
O1 C1 C2 C11 -128.6(4) . . . . ?
C19 C1 C2 C11 100.8(5) . . . . ?
C10 C1 C2 C11 -12.0(4) . . . . ?
C11 C2 C3 O2 -48.6(7) . . . . ?
C1 C2 C3 O2 -151.7(5) . . . . ?
C11 C2 C3 C4 135.1(5) . . . . ?
C1 C2 C3 C4 32.0(6) . . . . ?
O2 C3 C4 C9 158.3(5) . . . . ?
C2 C3 C4 C9 -25.5(7) . . . . ?
O2 C3 C4 C5 -26.7(8) . . . . ?
C2 C3 C4 C5 149.6(5) . . . . ?
C9 C4 C5 C6 -0.3(9) . . . . ?
C3 C4 C5 C6 -175.5(6) . . . . ?
C4 C5 C6 C7 1.5(11) . . . . ?
C5 C6 C7 C8 -3.2(12) . . . . ?
C6 C7 C8 C9 3.5(11) . . . . ?
C5 C4 C9 C8 0.6(8) . . . . ?
C3 C4 C9 C8 175.8(5) . . . . ?
C5 C4 C9 O1 176.5(5) . . . . ?
C3 C4 C9 O1 -8.4(8) . . . . ?
C7 C8 C9 C4 -2.2(9) . . . . ?
C7 C8 C9 O1 -178.2(6) . . . . ?
O1 C1 C10 O3 -105.2(5) . . . . ?
C19 C1 C10 O3 19.6(6) . . . . ?
C2 C1 C10 O3 133.7(4) . . . . ?
O1 C1 C10 C26 20.2(6) . . . . ?
C19 C1 C10 C26 145.0(5) . . . . ?
C2 C1 C10 C26 -101.0(4) . . . . ?
O1 C1 C10 C11 133.1(4) . . . . ?
C19 C1 C10 C11 -102.1(5) . . . . ?
C2 C1 C10 C11 12.0(4) . . . . ?
O3 C10 C11 C12 -9.1(7) . . . . ?
C26 C10 C11 C12 -140.5(5) . . . . ?
C1 C10 C11 C12 107.9(5) . . . . ?
O3 C10 C11 C2 -129.0(4) . . . . ?
C26 C10 C11 C2 99.6(5) . . . . ?
C1 C10 C11 C2 -12.0(4) . . . . ?
C3 C2 C11 C12 135.6(5) . . . . ?
C1 C2 C11 C12 -106.8(5) . . . . ?
C3 C2 C11 C10 -105.5(5) . . . . ?
C1 C2 C11 C10 12.2(4) . . . . ?
C10 C11 C12 O4 -158.1(6) . . . . ?
C2 C11 C12 O4 -54.3(8) . . . . ?
C10 C11 C12 C13 25.8(8) . . . . ?
C2 C11 C12 C13 129.6(5) . . . . ?
O4 C12 C13 C14 -16.7(10) . . . . ?
C11 C12 C13 C14 159.4(5) . . . . ?
O4 C12 C13 C18 162.6(6) . . . . ?
C11 C12 C13 C18 -21.4(8) . . . . ?
C18 C13 C14 C15 0.8(9) . . . . ?
C12 C13 C14 C15 -179.9(6) . . . . ?
C13 C14 C15 C16 -1.7(9) . . . . ?
C14 C15 C16 C17 1.0(9) . . . . ?
C15 C16 C17 C18 0.7(9) . . . . ?
C16 C17 C18 O3 -178.1(5) . . . . ?
C16 C17 C18 C13 -1.6(8) . . . . ?
C14 C13 C18 C17 0.9(8) . . . . ?
C12 C13 C18 C17 -178.4(6) . . . . ?
C14 C13 C18 O3 177.1(5) . . . . ?
C12 C13 C18 O3 -2.1(8) . . . . ?
O1 C1 C19 O5 -163.8(5) . . . . ?
C2 C1 C19 O5 -28.8(7) . . . . ?
C10 C1 C19 O5 69.2(7) . . . . ?
O1 C1 C19 N1 17.9(7) . . . . ?
C2 C1 C19 N1 152.9(5) . . . . ?
C10 C1 C19 N1 -109.1(5) . . . . ?
N1 C20 C22 C23 -55.3(9) . . . . ?
C21 C20 C22 C23 -179.0(8) . . . . ?
N1 C20 C22 C24 65.5(11) . . . . ?
C21 C20 C22 C24 -58.2(13) . . . . ?
N1 C20 C22 C25 -175.9(8) . . . . ?
C21 C20 C22 C25 60.4(11) . . . . ?
O3 C10 C26 O6 -163.7(4) . . . . ?
C11 C10 C26 O6 -28.2(6) . . . . ?
C1 C10 C26 O6 69.4(6) . . . . ?
O3 C10 C26 N2 18.9(6) . . . . ?
C11 C10 C26 N2 154.3(4) . . . . ?
C1 C10 C26 N2 -108.0(5) . . . . ?
N2 C27 C29 C32 -170.8(5) . . . . ?
C28 C27 C29 C32 65.3(7) . . . . ?
N2 C27 C29 C31 67.8(6) . . . . ?
C28 C27 C29 C31 -56.1(6) . . . . ?
N2 C27 C29 C30 -53.0(6) . . . . ?
C28 C27 C29 C30 -176.9(5) . . . . ?
O5 C19 N1 C20 1.5(10) . . . . ?
C1 C19 N1 C20 179.7(6) . . . . ?
C21 C20 N1 C19 -105.7(9) . . . . ?
C22 C20 N1 C19 125.4(7) . . . . ?
O6 C26 N2 C27 1.4(8) . . . . ?
C10 C26 N2 C27 178.6(4) . . . . ?
C28 C27 N2 C26 -119.3(5) . . . . ?
C29 C27 N2 C26 113.2(6) . . . . ?
C4 C9 O1 C1 33.7(7) . . . . ?
C8 C9 O1 C1 -150.3(5) . . . . ?
C19 C1 O1 C9 108.0(5) . . . . ?
C2 C1 O1 C9 -23.9(6) . . . . ?
C10 C1 O1 C9 -126.3(5) . . . . ?
C17 C18 O3 C10 -162.9(5) . . . . ?
C13 C18 O3 C10 20.6(7) . . . . ?
C26 C10 O3 C18 117.8(4) . . . . ?
C11 C10 O3 C18 -14.0(6) . . . . ?
C1 C10 O3 C18 -117.3(4) . . . . ?

_refine_diff_density_max         0.742
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.127

_shelxl_version_number           2013-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
_database_code_depnum_ccdc_archive 'CCDC 1010753'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_saka426_p212121

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Anti-HH photodimer of (S)-N-(1-methoxycarbonylethyl)-2-chromonecarboxamide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 N2 O10'
_chemical_formula_weight         550.51
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   8.021(3)
_cell_length_b                   15.273(5)
_cell_length_c                   21.484(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2631.9(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    2736
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      21.67

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            14840
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.61
_reflns_number_total             5909
_reflns_number_gt                4432
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.4661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_number_reflns         5909
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1372
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_restrained_S_all      0.896
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5352(3) 0.12341(17) 0.87067(12) 0.0288(5) Uani 1 1 d . . .
C2 C 0.6970(3) 0.12735(17) 0.96529(12) 0.0298(5) Uani 1 1 d . . .
C3 C 0.8564(3) 0.12893(19) 0.99090(13) 0.0340(6) Uani 1 1 d . . .
H3 H 0.9518 0.1256 0.9648 0.041 Uiso 1 1 calc R . .
C4 C 0.8740(4) 0.1354(2) 1.05411(14) 0.0386(7) Uani 1 1 d . . .
H4 H 0.9827 0.1351 1.0717 0.046 Uiso 1 1 calc R . .
C5 C 0.7364(4) 0.1424(2) 1.09302(14) 0.0408(7) Uani 1 1 d . . .
H5 H 0.7509 0.1475 1.1368 0.049 Uiso 1 1 calc R . .
C6 C 0.5797(4) 0.14173(19) 1.06772(13) 0.0358(6) Uani 1 1 d . . .
H6 H 0.4852 0.1468 1.0942 0.043 Uiso 1 1 calc R . .
C7 C 0.5568(3) 0.13374(17) 1.00321(13) 0.0312(6) Uani 1 1 d . . .
C8 C 0.3879(3) 0.12769(19) 0.97703(13) 0.0337(6) Uani 1 1 d . . .
C9 C 0.3734(3) 0.13844(18) 0.90798(12) 0.0289(5) Uani 1 1 d . . .
H9 H 0.3221 0.1962 0.8972 0.035 Uiso 1 1 calc R . .
C10 C 0.2884(3) 0.06350(18) 0.87210(13) 0.0313(6) Uani 1 1 d . . .
H10 H 0.2376 0.0195 0.9009 0.038 Uiso 1 1 calc R . .
C11 C 0.1676(3) 0.09137(18) 0.82193(15) 0.0352(6) Uani 1 1 d . . .
C12 C 0.2004(4) 0.05673(18) 0.75936(14) 0.0377(7) Uani 1 1 d . . .
C13 C 0.0761(4) 0.0615(2) 0.71311(16) 0.0484(8) Uani 1 1 d . . .
H13 H -0.0301 0.0853 0.7229 0.058 Uiso 1 1 calc R . .
C14 C 0.1081(5) 0.0318(2) 0.65421(17) 0.0554(10) Uani 1 1 d . . .
H14 H 0.0233 0.0346 0.6234 0.067 Uiso 1 1 calc R . .
C15 C 0.2633(6) -0.0022(2) 0.63918(16) 0.0536(9) Uani 1 1 d . . .
H15 H 0.2848 -0.0222 0.5981 0.064 Uiso 1 1 calc R . .
C16 C 0.3868(5) -0.0071(2) 0.68393(14) 0.0450(7) Uani 1 1 d . . .
H16 H 0.4936 -0.0298 0.6737 0.054 Uiso 1 1 calc R . .
C17 C 0.3535(4) 0.02121(18) 0.74364(13) 0.0361(6) Uani 1 1 d . . .
C18 C 0.4609(3) 0.03339(17) 0.84826(12) 0.0304(6) Uani 1 1 d . . .
C19 C 0.5322(3) -0.03962(17) 0.88848(14) 0.0320(6) Uani 1 1 d . . .
C20 C 0.7308(4) -0.15922(18) 0.89631(14) 0.0375(7) Uani 1 1 d . . .
H20 H 0.6677 -0.1732 0.9352 0.045 Uiso 1 1 calc R . .
C21 C 0.7574(4) -0.2430(2) 0.85972(18) 0.0500(8) Uani 1 1 d . . .
H21A H 0.8114 -0.2293 0.8200 0.075 Uiso 1 1 calc R . .
H21B H 0.6494 -0.2710 0.8518 0.075 Uiso 1 1 calc R . .
H21C H 0.8284 -0.2829 0.8837 0.075 Uiso 1 1 calc R . .
C22 C 0.8972(4) -0.11824(18) 0.91398(14) 0.0379(7) Uani 1 1 d . . .
C23 C 1.1182(5) -0.1234(3) 0.98567(18) 0.0740(13) Uani 1 1 d . . .
H23A H 1.1101 -0.0608 0.9953 0.111 Uiso 1 1 calc R . .
H23B H 1.1998 -0.1323 0.9523 0.111 Uiso 1 1 calc R . .
H23C H 1.1537 -0.1554 1.0229 0.111 Uiso 1 1 calc R . .
C24 C 0.5521(3) 0.18836(17) 0.81669(12) 0.0296(6) Uani 1 1 d . . .
C25 C 0.7353(4) 0.27489(19) 0.75219(13) 0.0349(6) Uani 1 1 d . . .
H25 H 0.6509 0.3224 0.7581 0.042 Uiso 1 1 calc R . .
C26 C 0.9058(4) 0.3167(2) 0.75956(16) 0.0448(7) Uani 1 1 d . . .
H26A H 0.9913 0.2709 0.7607 0.067 Uiso 1 1 calc R . .
H26B H 0.9091 0.3502 0.7984 0.067 Uiso 1 1 calc R . .
H26C H 0.9271 0.3559 0.7243 0.067 Uiso 1 1 calc R . .
C27 C 0.7154(4) 0.2416(3) 0.68733(17) 0.0576(10) Uani 1 1 d . . .
C28 C 0.7072(7) 0.1365(5) 0.6117(2) 0.109(2) Uani 1 1 d . . .
H28A H 0.7728 0.1798 0.5887 0.163 Uiso 1 1 calc R . .
H28B H 0.5911 0.1384 0.5976 0.163 Uiso 1 1 calc R . .
H28C H 0.7530 0.0779 0.6043 0.163 Uiso 1 1 calc R . .
N1 N 0.6363(3) -0.09555(15) 0.86035(12) 0.0384(6) Uani 1 1 d . . .
H1 H 0.6478 -0.0938 0.8196 0.046 Uiso 1 1 calc R . .
N2 N 0.7075(3) 0.21115(15) 0.80090(11) 0.0338(5) Uani 1 1 d . . .
H2 H 0.7930 0.1873 0.8202 0.041 Uiso 1 1 calc R . .
O1 O 0.6903(2) 0.11681(13) 0.90212(8) 0.0317(4) Uani 1 1 d . . .
O2 O 0.2638(2) 0.11762(17) 1.00900(10) 0.0469(6) Uani 1 1 d . . .
O3 O 0.4858(2) 0.01379(14) 0.78455(9) 0.0379(5) Uani 1 1 d . . .
O4 O 0.0497(2) 0.13834(14) 0.83468(11) 0.0453(5) Uani 1 1 d . . .
O5 O 0.4968(3) -0.04304(13) 0.94385(9) 0.0382(5) Uani 1 1 d . . .
O6 O 0.9678(3) -0.06324(15) 0.88463(12) 0.0544(6) Uani 1 1 d . . .
O7 O 0.9584(3) -0.15516(17) 0.96585(11) 0.0577(7) Uani 1 1 d . . .
O8 O 0.4270(2) 0.21624(13) 0.79118(9) 0.0380(5) Uani 1 1 d . . .
O9 O 0.7144(3) 0.1568(2) 0.68021(12) 0.0628(7) Uani 1 1 d . . .
O10 O 0.7038(5) 0.2924(3) 0.64376(13) 0.0950(11) 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 O1 1.419(3) . ?
C1 C24 1.532(4) . ?
C1 C9 1.543(3) . ?
C1 C18 1.574(4) . ?
C2 O1 1.368(3) . ?
C2 C7 1.392(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.470(4) . ?
C8 O2 1.219(3) . ?
C8 C9 1.497(4) . ?
C9 C10 1.539(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.511(4) . ?
C10 C18 1.546(4) . ?
C10 H10 1.0000 . ?
C11 O4 1.218(3) . ?
C11 C12 1.469(4) . ?
C12 C17 1.384(4) . ?
C12 C13 1.410(4) . ?
C13 C14 1.368(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 O3 1.383(3) . ?
C18 O3 1.415(3) . ?
C18 C19 1.522(4) . ?
C19 O5 1.224(3) . ?
C19 N1 1.339(3) . ?
C20 N1 1.455(4) . ?
C20 C21 1.517(4) . ?
C20 C22 1.522(4) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O6 1.193(3) . ?
C22 O7 1.342(4) . ?
C23 O7 1.435(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O8 1.220(3) . ?
C24 N2 1.338(3) . ?
C25 N2 1.447(4) . ?
C25 C27 1.492(5) . ?
C25 C26 1.518(4) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O10 1.219(5) . ?
C27 O9 1.305(5) . ?
C28 O9 1.505(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C24 109.2(2) . . ?
O1 C1 C9 120.0(2) . . ?
C24 C1 C9 111.8(2) . . ?
O1 C1 C18 114.6(2) . . ?
C24 C1 C18 111.5(2) . . ?
C9 C1 C18 88.3(2) . . ?
O1 C2 C7 123.9(2) . . ?
O1 C2 C3 115.5(2) . . ?
C7 C2 C3 120.6(2) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 118.6(3) . . ?
C2 C7 C8 121.1(2) . . ?
C6 C7 C8 120.3(2) . . ?
O2 C8 C7 123.0(2) . . ?
O2 C8 C9 120.6(2) . . ?
C7 C8 C9 116.4(2) . . ?
C8 C9 C10 116.7(2) . . ?
C8 C9 C1 115.7(2) . . ?
C10 C9 C1 90.1(2) . . ?
C8 C9 H9 110.9 . . ?
C10 C9 H9 110.9 . . ?
C1 C9 H9 110.9 . . ?
C11 C10 C9 115.6(2) . . ?
C11 C10 C18 114.9(2) . . ?
C9 C10 C18 89.5(2) . . ?
C11 C10 H10 111.7 . . ?
C9 C10 H10 111.7 . . ?
C18 C10 H10 111.7 . . ?
O4 C11 C12 123.9(3) . . ?
O4 C11 C10 120.2(3) . . ?
C12 C11 C10 115.9(2) . . ?
C17 C12 C13 118.4(3) . . ?
C17 C12 C11 121.6(3) . . ?
C13 C12 C11 120.0(3) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 O3 114.6(3) . . ?
C16 C17 C12 121.4(3) . . ?
O3 C17 C12 123.9(3) . . ?
O3 C18 C19 109.9(2) . . ?
O3 C18 C10 120.6(2) . . ?
C19 C18 C10 111.5(2) . . ?
O3 C18 C1 115.3(2) . . ?
C19 C18 C1 108.9(2) . . ?
C10 C18 C1 88.73(19) . . ?
O5 C19 N1 123.8(3) . . ?
O5 C19 C18 119.7(2) . . ?
N1 C19 C18 116.4(2) . . ?
N1 C20 C21 111.2(3) . . ?
N1 C20 C22 108.3(2) . . ?
C21 C20 C22 110.7(2) . . ?
N1 C20 H20 108.9 . . ?
C21 C20 H20 108.9 . . ?
C22 C20 H20 108.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C22 O7 124.1(3) . . ?
O6 C22 C20 125.0(3) . . ?
O7 C22 C20 110.8(3) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O7 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 C24 N2 124.2(2) . . ?
O8 C24 C1 119.6(2) . . ?
N2 C24 C1 116.3(2) . . ?
N2 C25 C27 115.5(3) . . ?
N2 C25 C26 110.3(2) . . ?
C27 C25 C26 109.7(3) . . ?
N2 C25 H25 107.0 . . ?
C27 C25 H25 107.0 . . ?
C26 C25 H25 107.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O10 C27 O9 122.7(4) . . ?
O10 C27 C25 120.6(4) . . ?
O9 C27 C25 116.6(3) . . ?
O9 C28 H28A 109.5 . . ?
O9 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O9 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C19 N1 C20 120.8(2) . . ?
C19 N1 H1 119.6 . . ?
C20 N1 H1 119.6 . . ?
C24 N2 C25 120.1(2) . . ?
C24 N2 H2 119.9 . . ?
C25 N2 H2 119.9 . . ?
C2 O1 C1 119.9(2) . . ?
C17 O3 C18 119.3(2) . . ?
C22 O7 C23 115.5(3) . . ?
C27 O9 C28 108.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -177.1(2) . . . . ?
C7 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
O1 C2 C7 C6 178.0(2) . . . . ?
C3 C2 C7 C6 0.0(4) . . . . ?
O1 C2 C7 C8 1.2(4) . . . . ?
C3 C2 C7 C8 -176.9(3) . . . . ?
C5 C6 C7 C2 -0.7(4) . . . . ?
C5 C6 C7 C8 176.2(3) . . . . ?
C2 C7 C8 O2 166.8(3) . . . . ?
C6 C7 C8 O2 -10.0(4) . . . . ?
C2 C7 C8 C9 -15.7(4) . . . . ?
C6 C7 C8 C9 167.5(2) . . . . ?
O2 C8 C9 C10 -58.5(4) . . . . ?
C7 C8 C9 C10 124.0(3) . . . . ?
O2 C8 C9 C1 -162.6(3) . . . . ?
C7 C8 C9 C1 19.8(4) . . . . ?
O1 C1 C9 C8 -11.5(4) . . . . ?
C24 C1 C9 C8 -141.3(2) . . . . ?
C18 C1 C9 C8 106.1(2) . . . . ?
O1 C1 C9 C10 -131.4(2) . . . . ?
C24 C1 C9 C10 98.7(2) . . . . ?
C18 C1 C9 C10 -13.86(19) . . . . ?
C8 C9 C10 C11 137.5(3) . . . . ?
C1 C9 C10 C11 -103.5(2) . . . . ?
C8 C9 C10 C18 -104.9(2) . . . . ?
C1 C9 C10 C18 14.11(19) . . . . ?
C9 C10 C11 O4 -57.0(4) . . . . ?
C18 C10 C11 O4 -159.2(3) . . . . ?
C9 C10 C11 C12 124.4(3) . . . . ?
C18 C10 C11 C12 22.2(4) . . . . ?
O4 C11 C12 C17 164.7(3) . . . . ?
C10 C11 C12 C17 -16.7(4) . . . . ?
O4 C11 C12 C13 -13.5(4) . . . . ?
C10 C11 C12 C13 165.1(3) . . . . ?
C17 C12 C13 C14 -0.3(4) . . . . ?
C11 C12 C13 C14 177.9(3) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 0.6(5) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 O3 -179.7(3) . . . . ?
C15 C16 C17 C12 -1.8(4) . . . . ?
C13 C12 C17 C16 1.6(4) . . . . ?
C11 C12 C17 C16 -176.6(3) . . . . ?
C13 C12 C17 O3 179.3(3) . . . . ?
C11 C12 C17 O3 1.1(4) . . . . ?
C11 C10 C18 O3 -14.6(4) . . . . ?
C9 C10 C18 O3 -132.8(2) . . . . ?
C11 C10 C18 C19 -145.8(2) . . . . ?
C9 C10 C18 C19 96.0(2) . . . . ?
C11 C10 C18 C1 104.3(2) . . . . ?
C9 C10 C18 C1 -13.83(19) . . . . ?
O1 C1 C18 O3 -100.1(3) . . . . ?
C24 C1 C18 O3 24.6(3) . . . . ?
C9 C1 C18 O3 137.4(2) . . . . ?
O1 C1 C18 C19 24.0(3) . . . . ?
C24 C1 C18 C19 148.7(2) . . . . ?
C9 C1 C18 C19 -98.5(2) . . . . ?
O1 C1 C18 C10 136.3(2) . . . . ?
C24 C1 C18 C10 -99.0(2) . . . . ?
C9 C1 C18 C10 13.80(19) . . . . ?
O3 C18 C19 O5 -166.7(2) . . . . ?
C10 C18 C19 O5 -30.2(3) . . . . ?
C1 C18 C19 O5 66.1(3) . . . . ?
O3 C18 C19 N1 15.4(3) . . . . ?
C10 C18 C19 N1 151.9(2) . . . . ?
C1 C18 C19 N1 -111.8(3) . . . . ?
N1 C20 C22 O6 -28.3(4) . . . . ?
C21 C20 C22 O6 93.8(4) . . . . ?
N1 C20 C22 O7 154.5(3) . . . . ?
C21 C20 C22 O7 -83.4(3) . . . . ?
O1 C1 C24 O8 -166.1(2) . . . . ?
C9 C1 C24 O8 -30.8(3) . . . . ?
C18 C1 C24 O8 66.3(3) . . . . ?
O1 C1 C24 N2 13.6(3) . . . . ?
C9 C1 C24 N2 148.9(2) . . . . ?
C18 C1 C24 N2 -114.0(3) . . . . ?
N2 C25 C27 O10 165.6(3) . . . . ?
C26 C25 C27 O10 -69.1(4) . . . . ?
N2 C25 C27 O9 -15.5(4) . . . . ?
C26 C25 C27 O9 109.8(3) . . . . ?
O5 C19 N1 C20 -7.3(4) . . . . ?
C18 C19 N1 C20 170.5(2) . . . . ?
C21 C20 N1 C19 147.4(3) . . . . ?
C22 C20 N1 C19 -90.8(3) . . . . ?
O8 C24 N2 C25 2.2(4) . . . . ?
C1 C24 N2 C25 -177.4(2) . . . . ?
C27 C25 N2 C24 -77.6(3) . . . . ?
C26 C25 N2 C24 157.3(3) . . . . ?
C7 C2 O1 C1 8.4(4) . . . . ?
C3 C2 O1 C1 -173.5(2) . . . . ?
C24 C1 O1 C2 128.3(2) . . . . ?
C9 C1 O1 C2 -2.7(4) . . . . ?
C18 C1 O1 C2 -105.8(3) . . . . ?
C16 C17 O3 C18 -174.3(2) . . . . ?
C12 C17 O3 C18 7.9(4) . . . . ?
C19 C18 O3 C17 131.4(2) . . . . ?
C10 C18 O3 C17 -0.5(4) . . . . ?
C1 C18 O3 C17 -105.0(3) . . . . ?
O6 C22 O7 C23 0.8(5) . . . . ?
C20 C22 O7 C23 178.0(3) . . . . ?
O10 C27 O9 C28 3.3(5) . . . . ?
C25 C27 O9 C28 -175.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.064
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
_database_code_depnum_ccdc_archive 'CCDC 1010754'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_saka451_p65_nontwin

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Anti-HH photodimer of (S)-N-(1-methoxycarbonylethyl)-2-chromonecarboxamide'
_chemical_name_common            ?
_chemical_melting_point          490-491
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H41 N3 O12'
_chemical_formula_weight         743.75
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   P6(5)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   12.380(5)
_cell_length_b                   12.380(5)
_cell_length_c                   42.393(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5627(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    173
_cell_measurement_reflns_used    3319
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      19.29

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2352
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9524
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            26515
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_sigmaI/netI    0.1035
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.43
_reflns_number_total             6805
_reflns_number_gt                5028
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0796P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0151(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(11)
_refine_ls_number_reflns         6805
_refine_ls_number_parameters     495
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.951
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0428(3) 0.8203(3) 0.11864(7) 0.0243(7) Uani 1 1 d . . .
C2 C 0.0414(3) 0.6958(3) 0.11407(8) 0.0264(7) Uani 1 1 d . . .
H2 H 0.1092 0.6941 0.1265 0.032 Uiso 1 1 calc R . .
C3 C -0.0812(4) 0.5799(4) 0.11917(8) 0.0333(8) Uani 1 1 d . . .
C4 C -0.1734(4) 0.5938(3) 0.13712(8) 0.0333(9) Uani 1 1 d . . .
C5 C -0.2815(4) 0.4878(4) 0.14789(9) 0.0421(10) Uani 1 1 d . . .
H5 H -0.2919 0.4075 0.1442 0.051 Uiso 1 1 calc R . .
C6 C -0.3716(4) 0.4981(4) 0.16356(10) 0.0472(11) Uani 1 1 d . . .
H6 H -0.4426 0.4258 0.1716 0.057 Uiso 1 1 calc R . .
C7 C -0.3594(4) 0.6156(5) 0.16777(9) 0.0450(11) Uani 1 1 d . . .
H7 H -0.4247 0.6223 0.1777 0.054 Uiso 1 1 calc R . .
C8 C -0.2539(4) 0.7224(4) 0.15772(8) 0.0385(9) Uani 1 1 d . . .
H8 H -0.2451 0.8023 0.1610 0.046 Uiso 1 1 calc R . .
C9 C -0.1604(3) 0.7099(4) 0.14256(7) 0.0297(8) Uani 1 1 d . . .
C10 C 0.1634(3) 0.9217(3) 0.13321(8) 0.0278(8) Uani 1 1 d . . .
C11 C 0.2670(4) 1.1228(4) 0.15884(8) 0.0350(9) Uani 1 1 d . . .
H11 H 0.3397 1.1089 0.1571 0.042 Uiso 1 1 calc R . .
C12 C 0.2876(5) 1.2266(4) 0.13600(10) 0.0640(15) Uani 1 1 d . . .
H12A H 0.2962 1.2028 0.1145 0.096 Uiso 1 1 calc R . .
H12B H 0.3637 1.3037 0.1419 0.096 Uiso 1 1 calc R . .
H12C H 0.2162 1.2402 0.1369 0.096 Uiso 1 1 calc R . .
C13 C 0.2580(3) 1.1562(3) 0.19227(8) 0.0315(8) Uani 1 1 d . . .
C14 C 0.3711(5) 1.3010(5) 0.23261(11) 0.0610(14) Uani 1 1 d . . .
H14A H 0.3069 1.3239 0.2363 0.091 Uiso 1 1 calc R . .
H14B H 0.4537 1.3737 0.2363 0.091 Uiso 1 1 calc R . .
H14C H 0.3580 1.2337 0.2470 0.091 Uiso 1 1 calc R . .
C15 C 0.0511(3) 0.8380(3) 0.08154(8) 0.0255(7) Uani 1 1 d . . .
C16 C 0.0796(3) 0.7304(3) 0.07912(8) 0.0272(8) Uani 1 1 d . . .
H16 H 0.0189 0.6634 0.0647 0.033 Uiso 1 1 calc R . .
C17 C 0.2106(4) 0.7668(3) 0.07061(8) 0.0309(8) Uani 1 1 d . . .
C18 C 0.2857(3) 0.8882(3) 0.05585(8) 0.0294(8) Uani 1 1 d . . .
C19 C 0.3990(4) 0.9205(4) 0.04150(9) 0.0382(9) Uani 1 1 d . . .
H19 H 0.4269 0.8616 0.0410 0.046 Uiso 1 1 calc R . .
C20 C 0.4713(4) 1.0354(4) 0.02805(9) 0.0416(10) Uani 1 1 d . . .
H20 H 0.5475 1.0552 0.0179 0.050 Uiso 1 1 calc R . .
C21 C 0.4324(4) 1.1228(4) 0.02929(9) 0.0410(10) Uani 1 1 d . . .
H21 H 0.4830 1.2028 0.0202 0.049 Uiso 1 1 calc R . .
C22 C 0.3209(4) 1.0948(3) 0.04362(8) 0.0338(9) Uani 1 1 d . . .
H22 H 0.2949 1.1550 0.0445 0.041 Uiso 1 1 calc R . .
C23 C 0.2482(3) 0.9777(3) 0.05655(8) 0.0273(8) Uani 1 1 d . . .
C24 C -0.0763(3) 0.8050(3) 0.06897(7) 0.0250(7) Uani 1 1 d . . .
C25 C -0.2076(3) 0.8791(4) 0.04685(8) 0.0330(8) Uani 1 1 d . . .
H25 H -0.2684 0.7874 0.0471 0.040 Uiso 1 1 calc R . .
C26 C -0.2537(5) 0.9407(5) 0.07012(10) 0.0537(12) Uani 1 1 d . . .
H26A H -0.2524 0.9113 0.0915 0.081 Uiso 1 1 calc R . .
H26B H -0.3391 0.9191 0.0647 0.081 Uiso 1 1 calc R . .
H26C H -0.1993 1.0314 0.0692 0.081 Uiso 1 1 calc R . .
C27 C -0.2012(3) 0.9243(3) 0.01381(8) 0.0306(8) Uani 1 1 d . . .
C28 C -0.3198(5) 0.9427(5) -0.02691(11) 0.0645(14) Uani 1 1 d . . .
H28A H -0.2656 1.0327 -0.0299 0.097 Uiso 1 1 calc R . .
H28B H -0.4062 0.9195 -0.0318 0.097 Uiso 1 1 calc R . .
H28C H -0.2931 0.8977 -0.0410 0.097 Uiso 1 1 calc R . .
C29 C 0.4302(6) 0.5953(5) 0.04129(15) 0.0730(15) Uani 1 1 d . . .
H29A H 0.3559 0.5638 0.0279 0.109 Uiso 1 1 calc R . .
H29B H 0.5051 0.6432 0.0284 0.109 Uiso 1 1 calc R . .
H29C H 0.4269 0.6492 0.0577 0.109 Uiso 1 1 calc R . .
C30 C 0.4340(4) 0.4905(5) 0.05593(12) 0.0536(12) Uani 1 1 d . . .
C31 C 0.5118(6) 0.5126(7) 0.08434(14) 0.097(2) Uani 1 1 d . . .
H31A H 0.5168 0.4378 0.0890 0.146 Uiso 1 1 calc R . .
H31B H 0.4743 0.5318 0.1023 0.146 Uiso 1 1 calc R . .
H31C H 0.5958 0.5830 0.0805 0.146 Uiso 1 1 calc R . .
C32 C 0.4617(4) 0.7837(5) 0.16119(12) 0.0577(13) Uani 1 1 d . . .
C33 C 0.3796(5) 0.6947(6) 0.14029(12) 0.0631(14) Uani 1 1 d . . .
H33 H 0.3770 0.7160 0.1189 0.076 Uiso 1 1 calc R . .
C34 C 0.3010(5) 0.5737(6) 0.15086(14) 0.0696(15) Uani 1 1 d . . .
H34 H 0.2446 0.5128 0.1364 0.083 Uiso 1 1 calc R . .
C35 C 0.3029(6) 0.5403(7) 0.18164(15) 0.0772(17) Uani 1 1 d . . .
H35 H 0.2501 0.4568 0.1884 0.093 Uiso 1 1 calc R . .
C36 C 0.3830(5) 0.6305(7) 0.20264(14) 0.0719(16) Uani 1 1 d . . .
H36 H 0.3824 0.6101 0.2243 0.086 Uiso 1 1 calc R . .
C37 C 0.4652(5) 0.7519(6) 0.19207(12) 0.0635(14) Uani 1 1 d . . .
H37 H 0.5235 0.8123 0.2063 0.076 Uiso 1 1 calc R . .
C38 C 0.5525(5) 0.9147(5) 0.15024(12) 0.0606(14) Uani 1 1 d . . .
C39 C 0.5841(5) 1.0906(6) 0.11792(14) 0.0720(15) Uani 1 1 d . . .
H39A H 0.6280 1.1473 0.1355 0.108 Uiso 1 1 calc R . .
H39B H 0.5293 1.1158 0.1076 0.108 Uiso 1 1 calc R . .
H39C H 0.6451 1.0939 0.1026 0.108 Uiso 1 1 calc R . .
N1 N 0.1554(3) 1.0085(3) 0.15000(7) 0.0304(7) Uani 1 1 d . . .
H1 H 0.0818 0.9963 0.1557 0.037 Uiso 1 1 calc R . .
N2 N -0.0875(3) 0.8970(3) 0.05608(7) 0.0313(7) Uani 1 1 d . . .
H2A H -0.0204 0.9702 0.0531 0.038 Uiso 1 1 calc R . .
O1 O -0.0596(2) 0.8207(2) 0.13311(5) 0.0279(5) Uani 1 1 d . . .
O2 O -0.0969(3) 0.4808(2) 0.10917(7) 0.0459(7) Uani 1 1 d . . .
O3 O 0.2600(2) 0.9219(3) 0.12722(6) 0.0353(6) Uani 1 1 d . . .
O4 O 0.1708(2) 1.1018(3) 0.20975(6) 0.0428(7) Uani 1 1 d . . .
O5 O 0.3632(2) 1.2594(3) 0.20051(6) 0.0448(7) Uani 1 1 d . . .
O6 O 0.1407(2) 0.9589(2) 0.07110(5) 0.0273(5) Uani 1 1 d . . .
O7 O 0.2483(3) 0.6938(3) 0.07533(6) 0.0421(7) Uani 1 1 d . . .
O8 O -0.1629(2) 0.6969(2) 0.07214(6) 0.0336(6) Uani 1 1 d . . .
O9 O -0.1138(3) 0.9644(3) -0.00343(6) 0.0430(7) Uani 1 1 d . . .
O10 O -0.3120(3) 0.9106(3) 0.00540(7) 0.0468(7) Uani 1 1 d . . .
O11 O 0.3741(5) 0.3884(4) 0.04457(13) 0.1060(17) Uani 1 1 d . . .
O12 O 0.6630(3) 0.9708(4) 0.15907(10) 0.0810(12) Uani 1 1 d . . .
N3 N 0.5103(4) 0.9647(5) 0.12979(11) 0.0699(12) Uani 1 1 d . . .
H3 H 0.4332 0.9192 0.1230 0.084 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.411(4) . ?
C1 C10 1.521(5) . ?
C1 C2 1.545(5) . ?
C1 C15 1.584(4) . ?
C2 C3 1.493(5) . ?
C2 C16 1.549(5) . ?
C2 H2 1.0000 . ?
C3 O2 1.218(4) . ?
C3 C4 1.452(6) . ?
C4 C9 1.383(5) . ?
C4 C5 1.402(5) . ?
C5 C6 1.358(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.397(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(5) . ?
C8 H8 0.9500 . ?
C9 O1 1.374(4) . ?
C10 O3 1.221(4) . ?
C10 N1 1.333(5) . ?
C11 N1 1.448(5) . ?
C11 C13 1.496(5) . ?
C11 C12 1.525(6) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O4 1.200(4) . ?
C13 O5 1.337(4) . ?
C14 O5 1.441(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O6 1.416(4) . ?
C15 C24 1.515(5) . ?
C15 C16 1.543(5) . ?
C16 C17 1.494(5) . ?
C16 H16 1.0000 . ?
C17 O7 1.223(4) . ?
C17 C18 1.455(5) . ?
C18 C19 1.392(5) . ?
C18 C23 1.400(5) . ?
C19 C20 1.370(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(5) . ?
C22 H22 0.9500 . ?
C23 O6 1.377(4) . ?
C24 O8 1.234(4) . ?
C24 N2 1.332(5) . ?
C25 N2 1.443(5) . ?
C25 C27 1.496(5) . ?
C25 C26 1.522(6) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O9 1.189(4) . ?
C27 O10 1.344(4) . ?
C28 O10 1.443(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.460(8) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 O11 1.201(6) . ?
C30 C31 1.480(8) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C37 1.374(7) . ?
C32 C33 1.382(7) . ?
C32 C38 1.512(8) . ?
C33 C34 1.391(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.373(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.384(9) . ?
C35 H35 0.9500 . ?
C36 C37 1.402(8) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 O12 1.242(6) . ?
C38 N3 1.316(7) . ?
C39 N3 1.447(7) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?
N3 H3 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C10 109.5(3) . . ?
O1 C1 C2 119.7(3) . . ?
C10 C1 C2 113.1(3) . . ?
O1 C1 C15 115.3(3) . . ?
C10 C1 C15 108.7(3) . . ?
C2 C1 C15 88.9(2) . . ?
C3 C2 C1 116.1(3) . . ?
C3 C2 C16 115.3(3) . . ?
C1 C2 C16 89.7(2) . . ?
C3 C2 H2 111.4 . . ?
C1 C2 H2 111.4 . . ?
C16 C2 H2 111.4 . . ?
O2 C3 C4 124.2(4) . . ?
O2 C3 C2 119.4(3) . . ?
C4 C3 C2 116.3(3) . . ?
C9 C4 C5 118.6(4) . . ?
C9 C4 C3 121.3(3) . . ?
C5 C4 C3 119.9(4) . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 118.4(4) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
O1 C9 C4 124.4(3) . . ?
O1 C9 C8 114.3(3) . . ?
C4 C9 C8 121.2(3) . . ?
O3 C10 N1 125.2(3) . . ?
O3 C10 C1 118.2(3) . . ?
N1 C10 C1 116.4(3) . . ?
N1 C11 C13 110.4(3) . . ?
N1 C11 C12 109.6(3) . . ?
C13 C11 C12 111.9(3) . . ?
N1 C11 H11 108.3 . . ?
C13 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O5 123.2(3) . . ?
O4 C13 C11 126.9(3) . . ?
O5 C13 C11 109.9(3) . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 C24 109.6(3) . . ?
O6 C15 C16 119.7(3) . . ?
C24 C15 C16 113.6(3) . . ?
O6 C15 C1 114.8(3) . . ?
C24 C15 C1 109.0(3) . . ?
C16 C15 C1 88.5(2) . . ?
C17 C16 C15 116.0(3) . . ?
C17 C16 C2 116.7(3) . . ?
C15 C16 C2 90.3(3) . . ?
C17 C16 H16 110.8 . . ?
C15 C16 H16 110.8 . . ?
C2 C16 H16 110.8 . . ?
O7 C17 C18 123.4(3) . . ?
O7 C17 C16 119.7(3) . . ?
C18 C17 C16 116.9(3) . . ?
C19 C18 C23 117.9(3) . . ?
C19 C18 C17 121.1(3) . . ?
C23 C18 C17 121.0(3) . . ?
C20 C19 C18 121.4(4) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.5(4) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.8(4) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.9(4) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
O6 C23 C22 115.1(3) . . ?
O6 C23 C18 123.4(3) . . ?
C22 C23 C18 121.5(3) . . ?
O8 C24 N2 124.5(3) . . ?
O8 C24 C15 118.5(3) . . ?
N2 C24 C15 117.0(3) . . ?
N2 C25 C27 109.8(3) . . ?
N2 C25 C26 111.3(3) . . ?
C27 C25 C26 112.5(3) . . ?
N2 C25 H25 107.7 . . ?
C27 C25 H25 107.7 . . ?
C26 C25 H25 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O9 C27 O10 123.2(3) . . ?
O9 C27 C25 126.8(3) . . ?
O10 C27 C25 110.0(3) . . ?
O10 C28 H28A 109.5 . . ?
O10 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O10 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O11 C30 C29 119.2(5) . . ?
O11 C30 C31 121.6(5) . . ?
C29 C30 C31 119.3(5) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C37 C32 C33 119.9(6) . . ?
C37 C32 C38 119.1(5) . . ?
C33 C32 C38 120.9(5) . . ?
C32 C33 C34 119.4(5) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C35 C34 C33 121.5(6) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C34 C35 C36 118.8(6) . . ?
C34 C35 H35 120.6 . . ?
C36 C35 H35 120.6 . . ?
C35 C36 C37 120.2(6) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C32 C37 C36 120.1(5) . . ?
C32 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
O12 C38 N3 121.3(5) . . ?
O12 C38 C32 121.9(5) . . ?
N3 C38 C32 116.7(4) . . ?
N3 C39 H39A 109.5 . . ?
N3 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
N3 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C10 N1 C11 120.5(3) . . ?
C10 N1 H1 119.8 . . ?
C11 N1 H1 119.8 . . ?
C24 N2 C25 121.3(3) . . ?
C24 N2 H2A 119.4 . . ?
C25 N2 H2A 119.4 . . ?
C9 O1 C1 119.5(3) . . ?
C13 O5 C14 116.6(3) . . ?
C23 O6 C15 119.9(3) . . ?
C27 O10 C28 115.0(3) . . ?
C38 N3 C39 123.4(4) . . ?
C38 N3 H3 118.3 . . ?
C39 N3 H3 118.3 . . ?

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
O1 C1 C2 C3 12.7(4) . . . . ?
C10 C1 C2 C3 144.0(3) . . . . ?
C15 C1 C2 C3 -106.1(3) . . . . ?
O1 C1 C2 C16 130.9(3) . . . . ?
C10 C1 C2 C16 -97.8(3) . . . . ?
C15 C1 C2 C16 12.1(2) . . . . ?
C1 C2 C3 O2 163.2(3) . . . . ?
C16 C2 C3 O2 60.2(4) . . . . ?
C1 C2 C3 C4 -18.9(4) . . . . ?
C16 C2 C3 C4 -121.9(3) . . . . ?
O2 C3 C4 C9 -167.3(3) . . . . ?
C2 C3 C4 C9 15.0(5) . . . . ?
O2 C3 C4 C5 9.3(6) . . . . ?
C2 C3 C4 C5 -168.4(3) . . . . ?
C9 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C5 C6 -177.2(4) . . . . ?
C4 C5 C6 C7 3.0(6) . . . . ?
C5 C6 C7 C8 -3.5(6) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C5 C4 C9 O1 -179.7(3) . . . . ?
C3 C4 C9 O1 -3.0(5) . . . . ?
C5 C4 C9 C8 -1.7(5) . . . . ?
C3 C4 C9 C8 175.0(3) . . . . ?
C7 C8 C9 O1 179.4(3) . . . . ?
C7 C8 C9 C4 1.2(5) . . . . ?
O1 C1 C10 O3 168.3(3) . . . . ?
C2 C1 C10 O3 32.1(4) . . . . ?
C15 C1 C10 O3 -64.9(4) . . . . ?
O1 C1 C10 N1 -15.9(4) . . . . ?
C2 C1 C10 N1 -152.1(3) . . . . ?
C15 C1 C10 N1 110.8(3) . . . . ?
N1 C11 C13 O4 -2.7(6) . . . . ?
C12 C11 C13 O4 119.6(4) . . . . ?
N1 C11 C13 O5 177.8(3) . . . . ?
C12 C11 C13 O5 -59.9(4) . . . . ?
O1 C1 C15 O6 102.9(3) . . . . ?
C10 C1 C15 O6 -20.4(4) . . . . ?
C2 C1 C15 O6 -134.4(3) . . . . ?
O1 C1 C15 C24 -20.4(4) . . . . ?
C10 C1 C15 C24 -143.7(3) . . . . ?
C2 C1 C15 C24 102.3(3) . . . . ?
O1 C1 C15 C16 -134.8(3) . . . . ?
C10 C1 C15 C16 101.9(3) . . . . ?
C2 C1 C15 C16 -12.2(2) . . . . ?
O6 C15 C16 C17 9.8(4) . . . . ?
C24 C15 C16 C17 141.9(3) . . . . ?
C1 C15 C16 C17 -108.0(3) . . . . ?
O6 C15 C16 C2 130.0(3) . . . . ?
C24 C15 C16 C2 -98.0(3) . . . . ?
C1 C15 C16 C2 12.1(2) . . . . ?
C3 C2 C16 C17 -134.0(3) . . . . ?
C1 C2 C16 C17 107.1(3) . . . . ?
C3 C2 C16 C15 106.5(3) . . . . ?
C1 C2 C16 C15 -12.4(3) . . . . ?
C15 C16 C17 O7 163.0(3) . . . . ?
C2 C16 C17 O7 58.4(4) . . . . ?
C15 C16 C17 C18 -19.2(4) . . . . ?
C2 C16 C17 C18 -123.7(3) . . . . ?
O7 C17 C18 C19 10.5(5) . . . . ?
C16 C17 C18 C19 -167.2(3) . . . . ?
O7 C17 C18 C23 -167.3(3) . . . . ?
C16 C17 C18 C23 15.0(5) . . . . ?
C23 C18 C19 C20 -0.9(5) . . . . ?
C17 C18 C19 C20 -178.8(4) . . . . ?
C18 C19 C20 C21 1.4(6) . . . . ?
C19 C20 C21 C22 -0.7(6) . . . . ?
C20 C21 C22 C23 -0.4(6) . . . . ?
C21 C22 C23 O6 178.2(3) . . . . ?
C21 C22 C23 C18 0.9(5) . . . . ?
C19 C18 C23 O6 -177.4(3) . . . . ?
C17 C18 C23 O6 0.5(5) . . . . ?
C19 C18 C23 C22 -0.3(5) . . . . ?
C17 C18 C23 C22 177.6(3) . . . . ?
O6 C15 C24 O8 170.5(3) . . . . ?
C16 C15 C24 O8 33.7(4) . . . . ?
C1 C15 C24 O8 -63.2(4) . . . . ?
O6 C15 C24 N2 -11.7(4) . . . . ?
C16 C15 C24 N2 -148.5(3) . . . . ?
C1 C15 C24 N2 114.6(3) . . . . ?
N2 C25 C27 O9 3.0(5) . . . . ?
C26 C25 C27 O9 127.5(4) . . . . ?
N2 C25 C27 O10 -178.5(3) . . . . ?
C26 C25 C27 O10 -54.0(4) . . . . ?
C37 C32 C33 C34 0.3(7) . . . . ?
C38 C32 C33 C34 177.3(5) . . . . ?
C32 C33 C34 C35 -0.1(8) . . . . ?
C33 C34 C35 C36 1.6(8) . . . . ?
C34 C35 C36 C37 -3.4(8) . . . . ?
C33 C32 C37 C36 -2.1(7) . . . . ?
C38 C32 C37 C36 -179.1(5) . . . . ?
C35 C36 C37 C32 3.6(8) . . . . ?
C37 C32 C38 O12 40.1(7) . . . . ?
C33 C32 C38 O12 -136.9(5) . . . . ?
C37 C32 C38 N3 -142.7(5) . . . . ?
C33 C32 C38 N3 40.3(7) . . . . ?
O3 C10 N1 C11 9.3(5) . . . . ?
C1 C10 N1 C11 -166.2(3) . . . . ?
C13 C11 N1 C10 -137.7(3) . . . . ?
C12 C11 N1 C10 98.6(4) . . . . ?
O8 C24 N2 C25 5.2(5) . . . . ?
C15 C24 N2 C25 -172.5(3) . . . . ?
C27 C25 N2 C24 -130.2(3) . . . . ?
C26 C25 N2 C24 104.6(4) . . . . ?
C4 C9 O1 C1 -4.3(5) . . . . ?
C8 C9 O1 C1 177.6(3) . . . . ?
C10 C1 O1 C9 -133.9(3) . . . . ?
C2 C1 O1 C9 -1.0(4) . . . . ?
C15 C1 O1 C9 103.3(3) . . . . ?
O4 C13 O5 C14 3.0(6) . . . . ?
C11 C13 O5 C14 -177.5(4) . . . . ?
C22 C23 O6 C15 171.8(3) . . . . ?
C18 C23 O6 C15 -11.0(4) . . . . ?
C24 C15 O6 C23 -128.5(3) . . . . ?
C16 C15 O6 C23 5.2(4) . . . . ?
C1 C15 O6 C23 108.5(3) . . . . ?
O9 C27 O10 C28 2.9(6) . . . . ?
C25 C27 O10 C28 -175.7(4) . . . . ?
O12 C38 N3 C39 -5.1(8) . . . . ?
C32 C38 N3 C39 177.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.083
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone/hexane'
_database_code_depnum_ccdc_archive 'CCDC 1010755'
