#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:37:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178434 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/55/4025526.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025526
loop_
_publ_author_name
'Jean-Charles Marié'
'Yuan Xiong'
'Geanna K. Min'
'Adam R. Yeager'
'Tohru Taniguchi'
'Nina Berova'
'Scott E. Schaus'
'John A. Porco'
_publ_section_title
;
 Enantioselective Synthesis of 3,4-Chromanediones via Asymmetric
 Rearrangement of 3-Allyloxyflavones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4584
_journal_page_last               4590
_journal_paper_doi               10.1021/jo100889c
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C33 H26 N4 O3'
_chemical_formula_sum            'C33 H26 N4 O3'
_chemical_formula_weight         526.58
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.009(4)
_cell_length_b                   15.153(6)
_cell_length_c                   17.540(6)
_cell_measurement_reflns_used    8874
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.01
_cell_measurement_theta_min      2.32
_cell_volume                     2660.2(18)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33418
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.2(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     481
_refine_ls_number_reflns         4912
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.407
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0791P)²+0.2054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                4190
_reflns_number_total             4912
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100889c_si_002.cif
_cod_data_source_block           porco79
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2660.2(17)
_cod_database_code               4025526
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'
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
O1 O 0.82603(10) 0.09751(6) 0.71125(6) 0.0264(2) Uani 1 1 d . . .
O2 O 0.21032(12) 0.09035(11) 0.88960(8) 0.0490(4) Uani 1 1 d . . .
O3 O 0.31844(12) 0.08293(10) 1.00121(7) 0.0422(3) Uani 1 1 d . . .
N1 N 0.60476(12) 0.11750(8) 0.55412(7) 0.0258(3) Uani 1 1 d . . .
N2 N 0.85539(12) 0.13005(8) 0.48041(7) 0.0271(3) Uani 1 1 d . . .
N3 N 0.45774(12) 0.10206(8) 0.82009(7) 0.0266(3) Uani 1 1 d . . .
N4 N 0.43956(13) 0.10055(9) 0.89732(7) 0.0297(3) Uani 1 1 d . . .
C1 C 0.70980(13) 0.13839(9) 0.67778(8) 0.0230(3) Uani 1 1 d . . .
C2 C 0.71583(13) 0.12842(8) 0.59178(7) 0.0210(3) Uani 1 1 d . . .
C3 C 0.61519(14) 0.11102(10) 0.47666(8) 0.0260(3) Uani 1 1 d . . .
C4 C 0.49923(17) 0.09530(13) 0.43279(10) 0.0375(4) Uani 1 1 d . . .
H4 H 0.410(2) 0.0895(13) 0.4583(12) 0.040(5) Uiso 1 1 d . . .
C5 C 0.50879(18) 0.08714(14) 0.35571(10) 0.0423(4) Uani 1 1 d . . .
H5 H 0.437(2) 0.0794(15) 0.3288(13) 0.051(6) Uiso 1 1 d . . .
C6 C 0.63276(19) 0.09574(13) 0.31887(9) 0.0394(4) Uani 1 1 d . . .
H6 H 0.643(2) 0.0951(14) 0.2640(13) 0.047(6) Uiso 1 1 d . . .
C7 C 0.74648(17) 0.11156(11) 0.35956(9) 0.0331(3) Uani 1 1 d . . .
H7 H 0.829(2) 0.1180(15) 0.3339(13) 0.045(6) Uiso 1 1 d . . .
C8 C 0.74037(14) 0.11864(9) 0.43992(8) 0.0251(3) Uani 1 1 d . . .
C9 C 0.84297(14) 0.13425(9) 0.55540(8) 0.0235(3) Uani 1 1 d . . .
C10 C 0.96173(14) 0.14114(9) 0.60373(9) 0.0259(3) Uani 1 1 d . . .
C11 C 1.08871(15) 0.16055(12) 0.57508(10) 0.0332(3) Uani 1 1 d . . .
H11 H 1.102(2) 0.1788(14) 0.5215(12) 0.045(6) Uiso 1 1 d . . .
C12 C 1.19836(16) 0.15922(12) 0.62288(11) 0.0397(4) Uani 1 1 d . . .
H12 H 1.282(2) 0.1746(14) 0.6023(12) 0.041(5) Uiso 1 1 d . . .
C13 C 1.18257(16) 0.13785(12) 0.69924(11) 0.0386(4) Uani 1 1 d . . .
H13 H 1.258(2) 0.1392(13) 0.7327(12) 0.041(5) Uiso 1 1 d . . .
C14 C 1.05799(16) 0.11906(11) 0.72893(10) 0.0332(3) Uani 1 1 d . . .
H14 H 1.0464(18) 0.1039(12) 0.7801(11) 0.030(5) Uiso 1 1 d . . .
C15 C 0.94737(14) 0.12104(9) 0.68079(8) 0.0254(3) Uani 1 1 d . . .
C16 C 0.59076(14) 0.08671(10) 0.70936(8) 0.0270(3) Uani 1 1 d . . .
H16B H 0.6075(17) 0.0282(13) 0.6964(10) 0.028(4) Uiso 1 1 d . . .
H16A H 0.5067(17) 0.1072(11) 0.6853(9) 0.020(4) Uiso 1 1 d . . .
C17 C 0.57500(14) 0.09214(9) 0.79379(8) 0.0259(3) Uani 1 1 d . . .
H17 H 0.6482(18) 0.0870(11) 0.8265(10) 0.022(4) Uiso 1 1 d . . .
C18 C 0.31229(16) 0.09167(12) 0.92447(9) 0.0333(3) Uani 1 1 d . . .
C19 C 0.45443(19) 0.07822(16) 1.02606(10) 0.0448(5) Uani 1 1 d . . .
H19 H 0.466(3) 0.138(2) 1.069(2) 0.101(11) Uiso 1 1 d . . .
C20 C 0.54202(15) 0.09566(10) 0.95611(8) 0.0264(3) Uani 1 1 d . . .
H20 H 0.6028(16) 0.0463(12) 0.9498(10) 0.024(4) Uiso 1 1 d . . .
C21 C 0.70433(13) 0.23571(9) 0.69996(7) 0.0220(3) Uani 1 1 d . . .
C22 C 0.62705(14) 0.29435(10) 0.65780(8) 0.0262(3) Uani 1 1 d . . .
H22 H 0.5826(17) 0.2720(11) 0.6134(9) 0.022(4) Uiso 1 1 d . . .
C23 C 0.62134(15) 0.38273(10) 0.67767(9) 0.0305(3) Uani 1 1 d . . .
H23 H 0.5688(19) 0.4208(13) 0.6482(11) 0.030(5) Uiso 1 1 d . . .
C24 C 0.68995(16) 0.41353(10) 0.74016(10) 0.0328(3) Uani 1 1 d . . .
H24 H 0.685(2) 0.4713(15) 0.7528(12) 0.046(5) Uiso 1 1 d . . .
C25 C 0.76442(16) 0.35521(11) 0.78343(10) 0.0339(3) Uani 1 1 d . . .
H25 H 0.813(2) 0.3712(16) 0.8268(14) 0.053(6) Uiso 1 1 d . . .
C26 C 0.77255(15) 0.26712(10) 0.76341(8) 0.0288(3) Uani 1 1 d . . .
H26 H 0.8251(19) 0.2265(13) 0.7885(11) 0.035(5) Uiso 1 1 d . . .
C27 C 0.62301(18) 0.18095(10) 0.96352(9) 0.0326(3) Uani 1 1 d . . .
H27B H 0.657(2) 0.2014(16) 0.9169(13) 0.048(6) Uiso 1 1 d . . .
H27A H 0.559(3) 0.2312(16) 0.9774(13) 0.059(7) Uiso 1 1 d . . .
C28 C 0.73470(18) 0.16857(10) 1.01900(9) 0.0349(4) Uani 1 1 d . A .
C29 C 0.7210(3) 0.20119(16) 1.09334(11) 0.0574(6) Uani 1 1 d . . .
C30 C 0.8455(6) 0.1766(4) 1.1407(3) 0.0626(15) Uani 0.454(5) 1 d P A 1
H30A H 0.8478 0.1941 1.1927 0.075 Uiso 0.454(5) 1 calc PR A 1
C31 C 0.9552(6) 0.1302(4) 1.1118(4) 0.0826(16) Uani 0.454(5) 1 d P A 1
H31A H 1.0277 0.1154 1.1444 0.099 Uiso 0.454(5) 1 calc PR A 1
C32 C 0.9580(5) 0.1053(4) 1.0344(4) 0.0642(18) Uani 0.454(5) 1 d P A 1
H32A H 1.0326 0.0779 1.0107 0.077 Uiso 0.454(5) 1 calc PR A 1
C30' C 0.8009(5) 0.1973(3) 1.1494(3) 0.0499(11) Uani 0.546(5) 1 d P A 2
H30B H 0.7817 0.2233 1.1974 0.060 Uiso 0.546(5) 1 calc PR A 2
C31' C 0.9195(5) 0.1517(3) 1.1346(3) 0.0502(12) Uani 0.546(5) 1 d P A 2
H31B H 0.9849 0.1473 1.1737 0.060 Uiso 0.546(5) 1 calc PR A 2
C32' C 0.9438(5) 0.1137(4) 1.0663(3) 0.0524(13) Uani 0.546(5) 1 d P A 2
H32B H 1.0227 0.0797 1.0598 0.063 Uiso 0.546(5) 1 calc PR A 2
C33 C 0.8484(2) 0.12371(13) 0.99956(16) 0.0547(6) Uani 1 1 d . . .
H33 H 0.861(2) 0.1089(15) 0.9544(13) 0.041(6) Uiso 1 1 d . . .
H19B H 0.464(3) 0.0321(18) 1.0478(15) 0.069(8) Uiso 1 1 d . . .
H29 H 0.642(4) 0.232(3) 1.104(2) 0.127(15) Uiso 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C1 116.31(10) . . ?
C18 O3 C19 110.54(13) . . ?
C2 N1 C3 116.60(12) . . ?
C9 N2 C8 116.40(12) . . ?
C17 N3 N4 118.75(12) . . ?
C18 N4 N3 118.10(12) . . ?
C18 N4 C20 113.88(12) . . ?
N3 N4 C20 127.51(12) . . ?
O1 C1 C2 109.25(11) . . ?
O1 C1 C21 109.88(11) . . ?
C2 C1 C21 110.55(11) . . ?
O1 C1 C16 105.13(11) . . ?
C2 C1 C16 109.88(11) . . ?
C21 C1 C16 111.99(12) . . ?
N1 C2 C9 122.83(12) . . ?
N1 C2 C1 118.84(12) . . ?
C9 C2 C1 118.30(12) . . ?
N1 C3 C4 119.41(14) . . ?
N1 C3 C8 121.01(12) . . ?
C4 C3 C8 119.58(13) . . ?
C5 C4 C3 119.91(16) . . ?
C4 C5 C6 120.70(16) . . ?
C7 C6 C5 120.82(15) . . ?
C6 C7 C8 119.88(15) . . ?
N2 C8 C3 121.42(12) . . ?
N2 C8 C7 119.46(14) . . ?
C3 C8 C7 119.09(13) . . ?
N2 C9 C2 121.72(12) . . ?
N2 C9 C10 120.20(13) . . ?
C2 C9 C10 118.03(12) . . ?
C15 C10 C11 119.25(13) . . ?
C15 C10 C9 117.55(13) . . ?
C11 C10 C9 123.04(14) . . ?
C12 C11 C10 120.07(16) . . ?
C11 C12 C13 119.94(16) . . ?
C14 C13 C12 121.01(15) . . ?
C13 C14 C15 118.99(15) . . ?
O1 C15 C14 117.48(13) . . ?
O1 C15 C10 121.69(12) . . ?
C14 C15 C10 120.73(14) . . ?
C17 C16 C1 114.44(12) . . ?
N3 C17 C16 117.70(13) . . ?
O2 C18 O3 123.24(15) . . ?
O2 C18 N4 128.47(15) . . ?
O3 C18 N4 108.28(13) . . ?
O3 C19 C20 106.98(13) . . ?
N4 C20 C19 99.96(12) . . ?
N4 C20 C27 112.95(12) . . ?
C19 C20 C27 112.38(14) . . ?
C26 C21 C22 118.71(13) . . ?
C26 C21 C1 121.16(12) . . ?
C22 C21 C1 120.11(12) . . ?
C23 C22 C21 120.45(14) . . ?
C24 C23 C22 120.54(15) . . ?
C23 C24 C25 119.32(15) . . ?
C26 C25 C24 120.62(15) . . ?
C25 C26 C21 120.33(14) . . ?
C28 C27 C20 110.21(12) . . ?
C33 C28 C29 119.2(2) . . ?
C33 C28 C27 121.49(17) . . ?
C29 C28 C27 119.26(18) . . ?
C30' C29 C28 130.0(3) . . ?
C30' C29 C30 20.4(3) . . ?
C28 C29 C30 109.7(3) . . ?
C31 C30 C29 124.1(4) . . ?
C30 C31 C32 119.9(5) . . ?
C33 C32 C31 112.5(6) . . ?
C29 C30' C31' 114.5(4) . . ?
C32' C31' C30' 121.8(5) . . ?
C31' C32' C33 121.8(5) . . ?
C32 C33 C28 134.3(4) . . ?
C32 C33 C32' 22.4(4) . . ?
C28 C33 C32' 112.4(3) . . ?
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
O1 C15 1.3738(18) . ?
O1 C1 1.4428(16) . ?
O2 C18 1.190(2) . ?
O3 C18 1.354(2) . ?
O3 C19 1.431(2) . ?
N1 C2 1.3036(18) . ?
N1 C3 1.3663(19) . ?
N2 C9 1.3227(19) . ?
N2 C8 1.3636(19) . ?
N3 C17 1.2700(19) . ?
N3 N4 1.3670(18) . ?
N4 C18 1.367(2) . ?
N4 C20 1.4562(19) . ?
C1 C2 1.5173(19) . ?
C1 C21 1.526(2) . ?
C1 C16 1.530(2) . ?
C2 C9 1.4263(19) . ?
C3 C4 1.413(2) . ?
C3 C8 1.414(2) . ?
C4 C5 1.361(2) . ?
C5 C6 1.405(3) . ?
C6 C7 1.365(2) . ?
C7 C8 1.415(2) . ?
C9 C10 1.4637(19) . ?
C10 C15 1.393(2) . ?
C10 C11 1.398(2) . ?
C11 C12 1.381(2) . ?
C12 C13 1.387(3) . ?
C13 C14 1.381(2) . ?
C14 C15 1.393(2) . ?
C16 C17 1.492(2) . ?
C19 C20 1.531(2) . ?
C20 C27 1.531(2) . ?
C21 C26 1.390(2) . ?
C21 C22 1.391(2) . ?
C22 C23 1.385(2) . ?
C23 C24 1.375(2) . ?
C24 C25 1.383(2) . ?
C25 C26 1.383(2) . ?
C27 C28 1.494(2) . ?
C28 C33 1.369(3) . ?
C28 C29 1.401(3) . ?
C29 C30' 1.268(5) . ?
C29 C30 1.543(6) . ?
C30 C31 1.399(10) . ?
C31 C32 1.409(10) . ?
C32 C33 1.287(6) . ?
C30' C31' 1.398(7) . ?
C31' C32' 1.353(8) . ?
C32' C33 1.518(6) . ?
