# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Liang-Liang Wang'
_publ_contact_author_email       llw20042004@yahoo.com.cn
loop_
_publ_author_name
'Liang-Liang Wang'
'Jian-Fei Bai'
'Lin Peng'
'Liang-Wen Qi'
'Li-Na Jia'
;
Xiaoying Xu
;
'Li-xin Wang'

data_mo_1847_9_sad
_database_code_depnum_ccdc_archive 'CCDC 849672'
#TrackingRef 'web_deposit_cif_file_0_Liang-LiangWang_1319125903.mo_1847_9_sad.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 Cl N2 O5'
_chemical_formula_sum            'C22 H21 Cl N2 O5'
_chemical_formula_weight         428.86
_chemical_absolute_configuration ad

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   12.6866(15)
_cell_length_b                   5.7581(7)
_cell_length_c                   14.9160(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.145(2)
_cell_angle_gamma                90.00
_cell_volume                     1001.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6765
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      29.99

_exptl_crystal_description       piece
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8382
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10651
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         30.08
_reflns_number_total             5461
_reflns_number_gt                5177
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0424P)^2^+0.3247P] where P=(Fo^2^+2Fc^2^)/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   0.00(5)
_refine_ls_number_reflns         5461
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Cl1 Cl 0.61270(3) 0.21546(9) 0.70268(3) 0.02733(11) Uani 1 1 d . . .
O1 O -0.08563(9) 0.2389(2) 0.69458(8) 0.0166(2) Uani 1 1 d . . .
O2 O -0.04227(9) 0.6131(2) 0.73704(8) 0.0143(2) Uani 1 1 d . . .
O3 O 0.34785(8) 0.7421(2) 0.82801(7) 0.0130(2) Uani 1 1 d . . .
O4 O 0.36296(9) 0.3702(2) 0.87906(8) 0.0138(2) Uani 1 1 d . . .
O5 O -0.00995(9) 0.5166(2) 0.55518(8) 0.0146(2) Uani 1 1 d . . .
N1 N 0.14192(11) 0.1107(2) 0.77564(9) 0.0117(2) Uani 1 1 d . . .
H1A H 0.1539 -0.0104 0.8144 0.014 Uiso 1 1 calc R . .
N2 N 0.14876(11) 0.5976(2) 0.52190(9) 0.0147(3) Uani 1 1 d . . .
H2 H 0.1168 0.6921 0.4722 0.018 Uiso 1 1 calc R . .
C1 C 0.45377(14) 0.4833(3) 0.56630(12) 0.0210(3) Uani 1 1 d . . .
H1 H 0.5121 0.5167 0.5433 0.025 Uiso 1 1 calc R . .
C2 C 0.47662(13) 0.3379(3) 0.64599(12) 0.0184(3) Uani 1 1 d . . .
C3 C 0.39471(13) 0.2865(3) 0.68410(11) 0.0146(3) Uani 1 1 d . . .
H3 H 0.4117 0.1852 0.7383 0.018 Uiso 1 1 calc R . .
C4 C 0.28783(12) 0.3890(3) 0.63984(10) 0.0120(3) Uani 1 1 d . . .
C5 C 0.18142(12) 0.3711(3) 0.66196(10) 0.0105(3) Uani 1 1 d . . .
C6 C 0.18481(11) 0.5069(3) 0.75470(10) 0.0098(2) Uani 1 1 d . . .
H6 H 0.1487 0.6637 0.7366 0.012 Uiso 1 1 calc R . .
C7 C 0.11296(12) 0.3475(3) 0.79378(10) 0.0101(3) Uani 1 1 d . . .
C8 C 0.13226(12) 0.3849(3) 0.90066(10) 0.0110(3) Uani 1 1 d . . .
C9 C 0.17319(13) 0.5954(3) 0.94786(11) 0.0135(3) Uani 1 1 d . . .
H9 H 0.1915 0.7183 0.9140 0.016 Uiso 1 1 calc R . .
C10 C 0.18729(13) 0.6258(3) 1.04468(11) 0.0156(3) Uani 1 1 d . . .
H10 H 0.2172 0.7677 1.0772 0.019 Uiso 1 1 calc R . .
C11 C 0.15759(13) 0.4487(3) 1.09374(11) 0.0169(3) Uani 1 1 d . . .
H11 H 0.1673 0.4697 1.1597 0.020 Uiso 1 1 calc R . .
C12 C 0.34505(14) 0.5800(3) 0.52016(12) 0.0198(3) Uani 1 1 d . . .
H12 H 0.3271 0.6770 0.4646 0.024 Uiso 1 1 calc R . .
C13 C 0.26386(13) 0.5299(3) 0.55813(11) 0.0143(3) Uani 1 1 d . . .
C14 C 0.14666(12) 0.1191(3) 0.67883(10) 0.0118(3) Uani 1 1 d . . .
H14A H 0.0709 0.0790 0.6279 0.014 Uiso 1 1 calc R . .
H14B H 0.2037 0.0060 0.6753 0.014 Uiso 1 1 calc R . .
C15 C 0.10182(12) 0.2084(3) 0.94982(10) 0.0139(3) Uani 1 1 d . . .
H15 H 0.0729 0.0654 0.9178 0.017 Uiso 1 1 calc R . .
C16 C 0.11374(12) 0.2412(3) 1.04630(11) 0.0159(3) Uani 1 1 d . . .
H16 H 0.0918 0.1216 1.0793 0.019 Uiso 1 1 calc R . .
C17 C -0.01690(12) 0.3888(3) 0.73466(10) 0.0116(3) Uani 1 1 d . . .
C18 C -0.15929(13) 0.6764(3) 0.67733(12) 0.0164(3) Uani 1 1 d . . .
H18A H -0.1789 0.6214 0.6105 0.025 Uiso 1 1 calc R . .
H18B H -0.1674 0.8457 0.6771 0.025 Uiso 1 1 calc R . .
H18C H -0.2110 0.6050 0.7039 0.025 Uiso 1 1 calc R . .
C19 C 0.30804(12) 0.5267(3) 0.82815(10) 0.0105(3) Uani 1 1 d . . .
C20 C 0.46381(13) 0.7904(3) 0.90008(12) 0.0176(3) Uani 1 1 d . . .
H20A H 0.4726 0.7208 0.9633 0.021 Uiso 1 1 calc R . .
H20B H 0.4738 0.9604 0.9094 0.021 Uiso 1 1 calc R . .
C21 C 0.55616(14) 0.6963(4) 0.87035(14) 0.0268(4) Uani 1 1 d . . .
H21A H 0.5541 0.5262 0.8705 0.040 Uiso 1 1 calc R . .
H21B H 0.6312 0.7500 0.9165 0.040 Uiso 1 1 calc R . .
H21C H 0.5433 0.7516 0.8047 0.040 Uiso 1 1 calc R . .
C22 C 0.09223(12) 0.4987(3) 0.57336(10) 0.0115(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.01700(17) 0.0452(3) 0.02145(19) 0.0078(2) 0.00930(14) 0.01256(19)
O1 0.0141(5) 0.0132(5) 0.0199(5) -0.0004(5) 0.0038(4) -0.0029(4)
O2 0.0117(5) 0.0120(5) 0.0163(5) -0.0015(4) 0.0026(4) 0.0006(4)
O3 0.0116(4) 0.0110(5) 0.0128(5) 0.0002(4) 0.0009(4) -0.0019(4)
O4 0.0132(5) 0.0132(5) 0.0127(5) 0.0029(4) 0.0028(4) 0.0015(4)
O5 0.0125(4) 0.0165(5) 0.0129(5) 0.0011(4) 0.0030(4) 0.0003(4)
N1 0.0167(6) 0.0074(5) 0.0109(5) 0.0015(5) 0.0055(5) 0.0000(5)
N2 0.0127(5) 0.0174(6) 0.0122(6) 0.0067(5) 0.0029(5) 0.0023(5)
C1 0.0176(7) 0.0302(10) 0.0185(8) 0.0032(7) 0.0106(6) 0.0007(7)
C2 0.0135(6) 0.0270(9) 0.0142(7) 0.0011(6) 0.0050(6) 0.0040(6)
C3 0.0171(6) 0.0163(7) 0.0104(6) 0.0019(5) 0.0055(5) 0.0043(5)
C4 0.0142(6) 0.0123(7) 0.0091(6) -0.0011(5) 0.0039(5) 0.0003(5)
C5 0.0121(6) 0.0101(6) 0.0084(6) 0.0004(5) 0.0030(5) -0.0001(5)
C6 0.0111(6) 0.0088(6) 0.0088(6) 0.0004(5) 0.0033(5) -0.0009(5)
C7 0.0109(6) 0.0080(6) 0.0101(6) -0.0004(5) 0.0027(5) -0.0011(5)
C8 0.0112(6) 0.0123(7) 0.0098(6) -0.0003(5) 0.0045(5) 0.0003(5)
C9 0.0158(6) 0.0115(7) 0.0142(7) 0.0010(6) 0.0072(5) 0.0006(6)
C10 0.0163(6) 0.0169(7) 0.0124(6) -0.0023(6) 0.0042(5) 0.0009(6)
C11 0.0161(7) 0.0230(8) 0.0124(7) 0.0011(6) 0.0063(6) 0.0041(6)
C12 0.0200(7) 0.0246(9) 0.0160(7) 0.0069(6) 0.0083(6) 0.0011(6)
C13 0.0143(6) 0.0157(7) 0.0117(6) 0.0023(6) 0.0039(5) 0.0005(6)
C14 0.0167(7) 0.0073(6) 0.0104(6) -0.0008(5) 0.0044(5) -0.0011(5)
C15 0.0135(6) 0.0129(7) 0.0159(7) 0.0007(6) 0.0066(5) -0.0004(6)
C16 0.0160(6) 0.0184(8) 0.0158(7) 0.0057(6) 0.0090(5) 0.0029(6)
C17 0.0124(6) 0.0129(7) 0.0096(6) 0.0009(5) 0.0044(5) -0.0005(5)
C18 0.0122(6) 0.0139(7) 0.0196(7) 0.0015(6) 0.0025(5) 0.0028(5)
C19 0.0125(6) 0.0108(6) 0.0089(6) -0.0015(5) 0.0048(5) -0.0008(5)
C20 0.0129(6) 0.0161(7) 0.0175(7) -0.0020(6) -0.0007(5) -0.0040(6)
C21 0.0147(7) 0.0285(10) 0.0352(10) -0.0014(8) 0.0078(7) -0.0041(7)
C22 0.0148(6) 0.0081(6) 0.0091(6) 0.0002(5) 0.0020(5) -0.0001(5)

_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
Cl1 C2 1.7450(16) . ?
O1 C17 1.2051(19) . ?
O2 C17 1.3353(19) . ?
O2 C18 1.4458(17) . ?
O3 C19 1.3391(18) . ?
O3 C20 1.4676(17) . ?
O4 C19 1.2078(19) . ?
O5 C22 1.2199(18) . ?
N1 C7 1.4646(19) . ?
N1 C14 1.4695(18) . ?
N1 H1A 0.8800 . ?
N2 C22 1.3639(19) . ?
N2 C13 1.3987(19) . ?
N2 H2 0.8800 . ?
C1 C2 1.388(2) . ?
C1 C12 1.393(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.398(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C13 1.395(2) . ?
C4 C5 1.514(2) . ?
C5 C22 1.546(2) . ?
C5 C14 1.565(2) . ?
C5 C6 1.575(2) . ?
C6 C19 1.5202(19) . ?
C6 C7 1.559(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.530(2) . ?
C7 C17 1.5512(19) . ?
C8 C15 1.394(2) . ?
C8 C9 1.395(2) . ?
C9 C10 1.395(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C16 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.400(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.507(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C17 O2 C18 115.30(12) . . ?
C19 O3 C20 116.38(11) . . ?
C7 N1 C14 105.14(11) . . ?
C7 N1 H1A 127.4 . . ?
C14 N1 H1A 127.4 . . ?
C22 N2 C13 111.48(12) . . ?
C22 N2 H2 124.3 . . ?
C13 N2 H2 124.3 . . ?
C2 C1 C12 119.81(15) . . ?
C2 C1 H1 120.1 . . ?
C12 C1 H1 120.1 . . ?
C1 C2 C3 122.51(14) . . ?
C1 C2 Cl1 119.50(12) . . ?
C3 C2 Cl1 117.98(12) . . ?
C4 C3 C2 117.43(14) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C13 120.04(14) . . ?
C3 C4 C5 131.06(14) . . ?
C13 C4 C5 108.86(12) . . ?
C4 C5 C22 101.37(11) . . ?
C4 C5 C14 115.46(12) . . ?
C22 C5 C14 114.84(12) . . ?
C4 C5 C6 116.03(12) . . ?
C22 C5 C6 105.83(11) . . ?
C14 C5 C6 103.37(11) . . ?
C19 C6 C7 111.19(11) . . ?
C19 C6 C5 109.60(11) . . ?
C7 C6 C5 102.58(11) . . ?
C19 C6 H6 111.1 . . ?
C7 C6 H6 111.1 . . ?
C5 C6 H6 111.1 . . ?
N1 C7 C8 111.99(12) . . ?
N1 C7 C17 108.97(12) . . ?
C8 C7 C17 105.66(11) . . ?
N1 C7 C6 104.66(11) . . ?
C8 C7 C6 115.41(12) . . ?
C17 C7 C6 110.10(11) . . ?
C15 C8 C9 119.55(13) . . ?
C15 C8 C7 118.79(13) . . ?
C9 C8 C7 121.56(13) . . ?
C10 C9 C8 120.16(14) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.11(15) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C16 C11 C10 119.99(14) . . ?
C16 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C1 117.72(15) . . ?
C13 C12 H12 121.1 . . ?
C1 C12 H12 121.1 . . ?
C12 C13 C4 122.42(14) . . ?
C12 C13 N2 127.91(14) . . ?
C4 C13 N2 109.62(13) . . ?
N1 C14 C5 108.14(11) . . ?
N1 C14 H14A 110.1 . . ?
C5 C14 H14A 110.1 . . ?
N1 C14 H14B 110.1 . . ?
C5 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
C8 C15 C16 120.13(15) . . ?
C8 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.01(15) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O1 C17 O2 124.81(14) . . ?
O1 C17 C7 124.90(14) . . ?
O2 C17 C7 110.26(12) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O3 124.56(13) . . ?
O4 C19 C6 124.95(14) . . ?
O3 C19 C6 110.49(12) . . ?
O3 C20 C21 112.82(13) . . ?
O3 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
O3 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
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 . . ?
O5 C22 N2 125.97(14) . . ?
O5 C22 C5 125.93(13) . . ?
N2 C22 C5 108.02(12) . . ?

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
C12 C1 C2 C3 -1.3(3) . . . . ?
C12 C1 C2 Cl1 179.44(14) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
Cl1 C2 C3 C4 178.56(12) . . . . ?
C2 C3 C4 C13 2.5(2) . . . . ?
C2 C3 C4 C5 179.89(16) . . . . ?
C3 C4 C5 C22 -171.24(16) . . . . ?
C13 C4 C5 C22 6.40(16) . . . . ?
C3 C4 C5 C14 -46.5(2) . . . . ?
C13 C4 C5 C14 131.16(14) . . . . ?
C3 C4 C5 C6 74.7(2) . . . . ?
C13 C4 C5 C6 -107.67(14) . . . . ?
C4 C5 C6 C19 -27.94(17) . . . . ?
C22 C5 C6 C19 -139.44(12) . . . . ?
C14 C5 C6 C19 99.49(13) . . . . ?
C4 C5 C6 C7 -146.15(12) . . . . ?
C22 C5 C6 C7 102.36(12) . . . . ?
C14 C5 C6 C7 -18.72(13) . . . . ?
C14 N1 C7 C8 -166.38(11) . . . . ?
C14 N1 C7 C17 77.09(13) . . . . ?
C14 N1 C7 C6 -40.66(13) . . . . ?
C19 C6 C7 N1 -80.42(14) . . . . ?
C5 C6 C7 N1 36.66(13) . . . . ?
C19 C6 C7 C8 43.13(16) . . . . ?
C5 C6 C7 C8 160.22(12) . . . . ?
C19 C6 C7 C17 162.61(12) . . . . ?
C5 C6 C7 C17 -80.31(13) . . . . ?
N1 C7 C8 C15 -40.21(17) . . . . ?
C17 C7 C8 C15 78.29(16) . . . . ?
C6 C7 C8 C15 -159.82(13) . . . . ?
N1 C7 C8 C9 143.50(13) . . . . ?
C17 C7 C8 C9 -97.99(15) . . . . ?
C6 C7 C8 C9 23.90(19) . . . . ?
C15 C8 C9 C10 2.2(2) . . . . ?
C7 C8 C9 C10 178.48(13) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
C9 C10 C11 C16 0.0(2) . . . . ?
C2 C1 C12 C13 1.5(3) . . . . ?
C1 C12 C13 C4 0.3(3) . . . . ?
C1 C12 C13 N2 -176.80(17) . . . . ?
C3 C4 C13 C12 -2.3(2) . . . . ?
C5 C4 C13 C12 179.73(15) . . . . ?
C3 C4 C13 N2 175.23(14) . . . . ?
C5 C4 C13 N2 -2.72(18) . . . . ?
C22 N2 C13 C12 174.49(17) . . . . ?
C22 N2 C13 C4 -2.89(19) . . . . ?
C7 N1 C14 C5 28.34(14) . . . . ?
C4 C5 C14 N1 122.97(13) . . . . ?
C22 C5 C14 N1 -119.59(13) . . . . ?
C6 C5 C14 N1 -4.82(14) . . . . ?
C9 C8 C15 C16 -0.9(2) . . . . ?
C7 C8 C15 C16 -177.21(13) . . . . ?
C10 C11 C16 C15 1.4(2) . . . . ?
C8 C15 C16 C11 -1.0(2) . . . . ?
C18 O2 C17 O1 -7.0(2) . . . . ?
C18 O2 C17 C7 174.85(12) . . . . ?
N1 C7 C17 O1 11.93(19) . . . . ?
C8 C7 C17 O1 -108.57(16) . . . . ?
C6 C7 C17 O1 126.18(15) . . . . ?
N1 C7 C17 O2 -169.96(11) . . . . ?
C8 C7 C17 O2 69.53(14) . . . . ?
C6 C7 C17 O2 -55.71(15) . . . . ?
C20 O3 C19 O4 -4.3(2) . . . . ?
C20 O3 C19 C6 176.26(12) . . . . ?
C7 C6 C19 O4 37.78(19) . . . . ?
C5 C6 C19 O4 -74.93(17) . . . . ?
C7 C6 C19 O3 -142.78(12) . . . . ?
C5 C6 C19 O3 104.51(13) . . . . ?
C19 O3 C20 C21 78.31(17) . . . . ?
C13 N2 C22 O5 -175.94(15) . . . . ?
C13 N2 C22 C5 7.10(17) . . . . ?
C4 C5 C22 O5 174.97(15) . . . . ?
C14 C5 C22 O5 49.8(2) . . . . ?
C6 C5 C22 O5 -63.55(18) . . . . ?
C4 C5 C22 N2 -8.06(15) . . . . ?
C14 C5 C22 N2 -133.24(13) . . . . ?
C6 C5 C22 N2 113.42(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O5 0.88 2.25 2.9415(18) 135.4 2_556
N2 H2 O1 0.88 2.38 3.1140(17) 141.7 2_556

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        30.08
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.054

# Attachment 'web_deposit_cif_file_1_Liang-LiangWang_1319125903.mo_1847_7_sad.cif'

data_mo_1847_7_sad
_database_code_depnum_ccdc_archive 'CCDC 849673'
#TrackingRef 'web_deposit_cif_file_1_Liang-LiangWang_1319125903.mo_1847_7_sad.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H27 Br N2 O7'
_chemical_formula_sum            'C27 H27 Br N2 O7'
_chemical_formula_weight         571.42
_chemical_absolute_configuration ad

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   11.9894(7)
_cell_length_b                   13.0968(8)
_cell_length_c                   17.2527(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2709.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    1.564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6105
_exptl_absorpt_correction_T_max  0.6958
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28898
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         30.03
_reflns_number_total             7693
_reflns_number_gt                6997
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0141P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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       0.0004(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(4)
_refine_ls_number_reflns         7693
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0529
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.398305(11) 0.803934(11) 0.809184(8) 0.01908(4) Uani 1 1 d . . .
O1 O 0.88426(9) 1.11713(7) 0.57548(6) 0.0170(2) Uani 1 1 d . . .
O2 O 0.69697(9) 1.14287(8) 0.57387(6) 0.0187(2) Uani 1 1 d . . .
O3 O 0.89128(10) 0.51000(8) 0.76876(6) 0.0192(2) Uani 1 1 d . . .
O4 O 0.75762(9) 0.62566(9) 0.79203(7) 0.0261(3) Uani 1 1 d . . .
O5 O 0.72180(11) 0.58603(9) 0.62474(8) 0.0315(3) Uani 1 1 d . . .
O6 O 0.69274(9) 0.73543(8) 0.56253(6) 0.0202(2) Uani 1 1 d . . .
O7 O 0.93797(8) 0.91989(8) 0.58965(6) 0.0181(2) Uani 1 1 d . . .
N1 N 0.77214(10) 0.99903(9) 0.62727(7) 0.0129(2) Uani 1 1 d . . .
N2 N 0.94391(10) 0.75622(9) 0.76737(7) 0.0149(2) Uani 1 1 d . . .
C1 C 1.20728(14) 0.55058(13) 0.60226(10) 0.0242(4) Uani 1 1 d . . .
H1 H 1.2719 0.5259 0.5765 0.029 Uiso 1 1 calc R . .
C2 C 1.21752(14) 0.61053(13) 0.66800(10) 0.0245(4) Uani 1 1 d . . .
H2 H 1.2894 0.6255 0.6881 0.029 Uiso 1 1 calc R . .
C3 C 1.12333(12) 0.64882(12) 0.70465(9) 0.0191(3) Uani 1 1 d . . .
H3 H 1.1313 0.6900 0.7497 0.023 Uiso 1 1 calc R . .
C4 C 1.01720(12) 0.62744(11) 0.67597(8) 0.0145(3) Uani 1 1 d . . .
C5 C 0.91297(11) 0.67517(10) 0.71121(8) 0.0133(3) Uani 1 1 d . . .
C6 C 0.84168(11) 0.73074(10) 0.64833(8) 0.0121(3) Uani 1 1 d . . .
H6 H 0.8942 0.7440 0.6044 0.015 Uiso 1 1 calc R . .
C7 C 0.81445(11) 0.83710(10) 0.68219(8) 0.0114(3) Uani 1 1 d . . .
C8 C 0.85334(12) 0.92213(11) 0.62678(8) 0.0128(3) Uani 1 1 d . . .
C9 C 0.77907(12) 1.09412(11) 0.58870(8) 0.0132(3) Uani 1 1 d . . .
C10 C 0.91365(12) 1.20918(11) 0.52869(8) 0.0171(3) Uani 1 1 d . . .
C11 C 0.86409(12) 1.19882(14) 0.44803(8) 0.0228(3) Uani 1 1 d . . .
H11A H 0.8908 1.1355 0.4241 0.034 Uiso 1 1 calc R . .
H11B H 0.8870 1.2572 0.4163 0.034 Uiso 1 1 calc R . .
H11C H 0.7825 1.1971 0.4517 0.034 Uiso 1 1 calc R . .
C12 C 1.04010(12) 1.20071(15) 0.52725(9) 0.0240(3) Uani 1 1 d . . .
H12A H 1.0689 1.2035 0.5804 0.036 Uiso 1 1 calc R . .
H12B H 1.0712 1.2574 0.4971 0.036 Uiso 1 1 calc R . .
H12C H 1.0617 1.1358 0.5033 0.036 Uiso 1 1 calc R . .
C13 C 0.67570(11) 0.96516(11) 0.66846(8) 0.0132(3) Uani 1 1 d . . .
C14 C 0.69616(11) 0.86999(10) 0.70080(8) 0.0117(3) Uani 1 1 d . . .
C15 C 0.61454(11) 0.82073(10) 0.74393(7) 0.0135(3) Uani 1 1 d . . .
H15 H 0.6276 0.7556 0.7664 0.016 Uiso 1 1 calc R . .
C16 C 0.51271(12) 0.87048(12) 0.75300(8) 0.0147(3) Uani 1 1 d . . .
C17 C 0.49282(12) 0.96609(12) 0.72220(9) 0.0173(3) Uani 1 1 d . . .
H17 H 0.4231 0.9986 0.7309 0.021 Uiso 1 1 calc R . .
C18 C 0.57481(11) 1.01522(11) 0.67821(9) 0.0173(3) Uani 1 1 d . . .
H18 H 0.5618 1.0804 0.6559 0.021 Uiso 1 1 calc R . .
C19 C 1.10205(15) 0.52690(11) 0.57422(9) 0.0240(3) Uani 1 1 d . . .
H19 H 1.0945 0.4844 0.5299 0.029 Uiso 1 1 calc R . .
C20 C 1.00779(13) 0.56519(12) 0.61068(9) 0.0198(3) Uani 1 1 d . . .
H20 H 0.9360 0.5488 0.5910 0.024 Uiso 1 1 calc R . .
C21 C 0.89065(13) 0.83731(10) 0.75271(8) 0.0140(3) Uani 1 1 d . . .
H21 H 0.8980 0.8961 0.7845 0.017 Uiso 1 1 calc R . .
C22 C 0.84302(12) 0.60059(11) 0.76101(9) 0.0164(3) Uani 1 1 d . . .
C23 C 0.83237(13) 0.43988(12) 0.81931(11) 0.0258(4) Uani 1 1 d . . .
H23A H 0.8200 0.4723 0.8698 0.039 Uiso 1 1 calc R . .
H23B H 0.8769 0.3778 0.8263 0.039 Uiso 1 1 calc R . .
H23C H 0.7604 0.4221 0.7960 0.039 Uiso 1 1 calc R . .
C24 C 0.74487(12) 0.67346(12) 0.61287(8) 0.0172(3) Uani 1 1 d . . .
C25 C 0.59468(12) 0.69453(14) 0.52334(9) 0.0252(3) Uani 1 1 d . . .
H25A H 0.6037 0.6201 0.5157 0.030 Uiso 1 1 calc R . .
H25B H 0.5869 0.7268 0.4717 0.030 Uiso 1 1 calc R . .
C26 C 0.49197(15) 0.7148(2) 0.57059(12) 0.0459(6) Uani 1 1 d . . .
H26A H 0.4964 0.6770 0.6195 0.069 Uiso 1 1 calc R . .
H26B H 0.4260 0.6926 0.5416 0.069 Uiso 1 1 calc R . .
H26C H 0.4864 0.7881 0.5815 0.069 Uiso 1 1 calc R . .
C27 C 0.87568(14) 1.30508(13) 0.56993(9) 0.0243(3) Uani 1 1 d . . .
H27A H 0.7940 1.3075 0.5706 0.036 Uiso 1 1 calc R . .
H27B H 0.9046 1.3651 0.5426 0.036 Uiso 1 1 calc R . .
H27C H 0.9038 1.3047 0.6233 0.036 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01373(6) 0.02260(7) 0.02091(7) 0.00611(6) 0.00415(6) -0.00265(6)
O1 0.0132(5) 0.0158(5) 0.0220(5) 0.0064(4) 0.0019(4) -0.0012(4)
O2 0.0150(5) 0.0181(5) 0.0229(5) 0.0066(4) 0.0022(4) 0.0033(4)
O3 0.0174(5) 0.0141(5) 0.0261(5) 0.0057(4) 0.0015(5) 0.0002(5)
O4 0.0226(6) 0.0217(6) 0.0338(7) 0.0110(5) 0.0101(5) 0.0064(5)
O5 0.0310(7) 0.0192(6) 0.0444(8) 0.0043(6) -0.0162(6) -0.0080(5)
O6 0.0197(5) 0.0224(6) 0.0184(5) -0.0006(4) -0.0088(4) -0.0004(5)
O7 0.0153(5) 0.0170(5) 0.0221(5) 0.0020(4) 0.0068(4) 0.0018(4)
N1 0.0104(5) 0.0114(6) 0.0171(6) 0.0018(5) 0.0026(5) 0.0003(4)
N2 0.0150(6) 0.0159(6) 0.0139(6) -0.0020(5) 0.0001(5) 0.0006(5)
C1 0.0217(8) 0.0197(8) 0.0313(9) 0.0017(7) 0.0077(7) 0.0064(7)
C2 0.0164(7) 0.0263(9) 0.0307(9) 0.0021(7) 0.0003(6) 0.0044(6)
C3 0.0176(7) 0.0189(7) 0.0207(7) -0.0003(6) -0.0016(6) 0.0031(6)
C4 0.0156(6) 0.0111(7) 0.0168(7) 0.0030(5) 0.0008(5) 0.0020(5)
C5 0.0135(6) 0.0124(7) 0.0140(6) -0.0001(5) -0.0013(5) 0.0010(5)
C6 0.0134(6) 0.0112(6) 0.0117(6) -0.0007(5) -0.0009(5) 0.0019(5)
C7 0.0116(6) 0.0105(6) 0.0122(6) 0.0006(5) -0.0012(5) -0.0004(5)
C8 0.0132(6) 0.0114(7) 0.0137(6) -0.0002(5) -0.0009(5) -0.0002(5)
C9 0.0158(7) 0.0113(7) 0.0124(6) 0.0009(5) 0.0025(5) -0.0015(5)
C10 0.0182(7) 0.0168(7) 0.0164(6) 0.0062(5) 0.0015(5) -0.0060(6)
C11 0.0218(7) 0.0293(8) 0.0172(7) 0.0036(7) 0.0007(5) -0.0056(7)
C12 0.0178(7) 0.0319(9) 0.0224(7) 0.0061(8) 0.0005(6) -0.0083(7)
C13 0.0111(6) 0.0139(7) 0.0144(7) 0.0006(5) 0.0023(5) -0.0023(5)
C14 0.0113(6) 0.0130(6) 0.0107(6) -0.0009(5) -0.0010(5) 0.0001(5)
C15 0.0148(6) 0.0128(7) 0.0128(6) 0.0007(5) 0.0003(5) 0.0003(5)
C16 0.0124(6) 0.0166(7) 0.0152(7) 0.0016(6) 0.0025(5) -0.0031(6)
C17 0.0108(6) 0.0191(8) 0.0220(7) 0.0016(6) 0.0016(6) 0.0020(6)
C18 0.0143(7) 0.0140(7) 0.0236(8) 0.0043(6) 0.0019(5) 0.0021(5)
C19 0.0278(8) 0.0178(7) 0.0265(8) -0.0039(6) 0.0054(7) 0.0040(7)
C20 0.0197(7) 0.0155(8) 0.0243(8) -0.0024(6) -0.0001(6) 0.0016(6)
C21 0.0134(6) 0.0153(6) 0.0132(6) -0.0012(5) 0.0010(5) -0.0007(6)
C22 0.0165(7) 0.0147(7) 0.0179(7) 0.0021(6) -0.0030(5) 0.0009(6)
C23 0.0210(7) 0.0197(8) 0.0365(10) 0.0142(7) -0.0017(7) -0.0018(6)
C24 0.0158(7) 0.0185(8) 0.0172(7) -0.0028(6) -0.0013(5) 0.0016(6)
C25 0.0195(7) 0.0347(8) 0.0215(7) -0.0082(7) -0.0095(6) -0.0007(9)
C26 0.0220(9) 0.0825(18) 0.0333(10) -0.0209(11) -0.0048(7) -0.0024(10)
C27 0.0321(9) 0.0169(7) 0.0238(7) 0.0029(7) 0.0006(6) -0.0043(8)

_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
Br1 C16 1.8923(14) . ?
O1 C9 1.3167(17) . ?
O1 C10 1.4930(17) . ?
O2 C9 1.2007(17) . ?
O3 C22 1.3268(18) . ?
O3 C23 1.4501(19) . ?
O4 C22 1.2011(18) . ?
O5 C24 1.1957(19) . ?
O6 C24 1.3429(18) . ?
O6 C25 1.4582(17) . ?
O7 C8 1.2003(17) . ?
N1 C8 1.4007(18) . ?
N1 C9 1.4144(18) . ?
N1 C13 1.4278(17) . ?
N2 C21 1.2647(18) . ?
N2 C5 1.4843(18) . ?
C1 C2 1.385(2) . ?
C1 C19 1.386(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C20 1.395(2) . ?
C4 C5 1.5238(19) . ?
C5 C22 1.5478(19) . ?
C5 C6 1.5612(19) . ?
C6 C24 1.511(2) . ?
C6 C7 1.5453(19) . ?
C6 H6 1.0000 . ?
C7 C14 1.5167(18) . ?
C7 C21 1.5214(19) . ?
C7 C8 1.5401(19) . ?
C10 C27 1.514(2) . ?
C10 C11 1.519(2) . ?
C10 C12 1.520(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.3861(19) . ?
C13 C14 1.3875(19) . ?
C14 C15 1.3883(19) . ?
C15 C16 1.393(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C17 C18 1.399(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 C26 1.501(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C9 O1 C10 120.30(11) . . ?
C22 O3 C23 114.49(12) . . ?
C24 O6 C25 116.95(12) . . ?
C8 N1 C9 126.11(12) . . ?
C8 N1 C13 110.03(11) . . ?
C9 N1 C13 123.73(12) . . ?
C21 N2 C5 110.10(11) . . ?
C2 C1 C19 119.55(15) . . ?
C2 C1 H1 120.2 . . ?
C19 C1 H1 120.2 . . ?
C1 C2 C3 120.38(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.57(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C20 118.55(14) . . ?
C3 C4 C5 121.64(13) . . ?
C20 C4 C5 119.71(13) . . ?
N2 C5 C4 110.42(11) . . ?
N2 C5 C22 102.96(11) . . ?
C4 C5 C22 114.01(11) . . ?
N2 C5 C6 104.90(11) . . ?
C4 C5 C6 111.28(11) . . ?
C22 C5 C6 112.54(11) . . ?
C24 C6 C7 115.99(11) . . ?
C24 C6 C5 118.05(12) . . ?
C7 C6 C5 105.85(10) . . ?
C24 C6 H6 105.2 . . ?
C7 C6 H6 105.2 . . ?
C5 C6 H6 105.2 . . ?
C14 C7 C21 113.06(12) . . ?
C14 C7 C8 102.07(11) . . ?
C21 C7 C8 108.26(11) . . ?
C14 C7 C6 122.25(11) . . ?
C21 C7 C6 100.20(10) . . ?
C8 C7 C6 110.68(11) . . ?
O7 C8 N1 127.47(13) . . ?
O7 C8 C7 124.71(13) . . ?
N1 C8 C7 107.80(11) . . ?
O2 C9 O1 128.80(13) . . ?
O2 C9 N1 121.35(13) . . ?
O1 C9 N1 109.83(12) . . ?
O1 C10 C27 110.18(11) . . ?
O1 C10 C11 109.33(12) . . ?
C27 C10 C11 112.77(13) . . ?
O1 C10 C12 100.68(12) . . ?
C27 C10 C12 111.61(13) . . ?
C11 C10 C12 111.62(12) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.03(13) . . ?
C18 C13 N1 128.33(13) . . ?
C14 C13 N1 109.64(12) . . ?
C13 C14 C15 120.56(12) . . ?
C13 C14 C7 109.59(12) . . ?
C15 C14 C7 129.84(12) . . ?
C14 C15 C16 117.43(13) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C17 C16 C15 122.17(13) . . ?
C17 C16 Br1 119.31(11) . . ?
C15 C16 Br1 118.52(11) . . ?
C16 C17 C18 120.30(14) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 117.49(13) . . ?
C13 C18 H18 121.3 . . ?
C17 C18 H18 121.3 . . ?
C1 C19 C20 120.16(15) . . ?
C1 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C4 120.76(15) . . ?
C19 C20 H20 119.6 . . ?
C4 C20 H20 119.6 . . ?
N2 C21 C7 117.49(12) . . ?
N2 C21 H21 121.3 . . ?
C7 C21 H21 121.3 . . ?
O4 C22 O3 124.84(14) . . ?
O4 C22 C5 122.46(13) . . ?
O3 C22 C5 112.58(12) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O5 C24 O6 125.58(14) . . ?
O5 C24 C6 125.71(14) . . ?
O6 C24 C6 108.61(12) . . ?
O6 C25 C26 110.17(12) . . ?
O6 C25 H25A 109.6 . . ?
C26 C25 H25A 109.6 . . ?
O6 C25 H25B 109.6 . . ?
C26 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
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 . . ?
C10 C27 H27A 109.5 . . ?
C10 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C10 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
C19 C1 C2 C3 -1.5(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C20 1.3(2) . . . . ?
C2 C3 C4 C5 -175.14(14) . . . . ?
C21 N2 C5 C4 129.41(12) . . . . ?
C21 N2 C5 C22 -108.49(13) . . . . ?
C21 N2 C5 C6 9.42(15) . . . . ?
C3 C4 C5 N2 9.60(18) . . . . ?
C20 C4 C5 N2 -166.75(13) . . . . ?
C3 C4 C5 C22 -105.74(15) . . . . ?
C20 C4 C5 C22 77.91(16) . . . . ?
C3 C4 C5 C6 125.67(14) . . . . ?
C20 C4 C5 C6 -50.68(17) . . . . ?
N2 C5 C6 C24 -144.03(12) . . . . ?
C4 C5 C6 C24 96.56(14) . . . . ?
C22 C5 C6 C24 -32.82(17) . . . . ?
N2 C5 C6 C7 -12.15(14) . . . . ?
C4 C5 C6 C7 -131.57(11) . . . . ?
C22 C5 C6 C7 99.05(13) . . . . ?
C24 C6 C7 C14 17.42(18) . . . . ?
C5 C6 C7 C14 -115.60(13) . . . . ?
C24 C6 C7 C21 143.17(12) . . . . ?
C5 C6 C7 C21 10.14(13) . . . . ?
C24 C6 C7 C8 -102.74(13) . . . . ?
C5 C6 C7 C8 124.23(11) . . . . ?
C9 N1 C8 O7 -6.0(2) . . . . ?
C13 N1 C8 O7 169.94(14) . . . . ?
C9 N1 C8 C7 175.08(12) . . . . ?
C13 N1 C8 C7 -9.00(15) . . . . ?
C14 C7 C8 O7 -169.90(14) . . . . ?
C21 C7 C8 O7 70.60(17) . . . . ?
C6 C7 C8 O7 -38.30(18) . . . . ?
C14 C7 C8 N1 9.08(14) . . . . ?
C21 C7 C8 N1 -110.42(13) . . . . ?
C6 C7 C8 N1 140.68(11) . . . . ?
C10 O1 C9 O2 -7.4(2) . . . . ?
C10 O1 C9 N1 174.16(11) . . . . ?
C8 N1 C9 O2 158.99(14) . . . . ?
C13 N1 C9 O2 -16.4(2) . . . . ?
C8 N1 C9 O1 -22.47(19) . . . . ?
C13 N1 C9 O1 162.14(13) . . . . ?
C9 O1 C10 C27 64.13(16) . . . . ?
C9 O1 C10 C11 -60.33(16) . . . . ?
C9 O1 C10 C12 -177.94(12) . . . . ?
C8 N1 C13 C18 -175.67(14) . . . . ?
C9 N1 C13 C18 0.4(2) . . . . ?
C8 N1 C13 C14 5.07(16) . . . . ?
C9 N1 C13 C14 -178.89(12) . . . . ?
C18 C13 C14 C15 0.7(2) . . . . ?
N1 C13 C14 C15 180.00(12) . . . . ?
C18 C13 C14 C7 -178.14(13) . . . . ?
N1 C13 C14 C7 1.17(15) . . . . ?
C21 C7 C14 C13 109.88(13) . . . . ?
C8 C7 C14 C13 -6.18(14) . . . . ?
C6 C7 C14 C13 -130.36(13) . . . . ?
C21 C7 C14 C15 -68.80(18) . . . . ?
C8 C7 C14 C15 175.14(13) . . . . ?
C6 C7 C14 C15 51.0(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C7 C14 C15 C16 178.63(13) . . . . ?
C14 C15 C16 C17 -1.4(2) . . . . ?
C14 C15 C16 Br1 178.39(10) . . . . ?
C15 C16 C17 C18 2.0(2) . . . . ?
Br1 C16 C17 C18 -177.81(11) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
N1 C13 C18 C17 -179.31(14) . . . . ?
C16 C17 C18 C13 -1.2(2) . . . . ?
C2 C1 C19 C20 1.6(2) . . . . ?
C1 C19 C20 C4 -0.3(2) . . . . ?
C3 C4 C20 C19 -1.2(2) . . . . ?
C5 C4 C20 C19 175.30(14) . . . . ?
C5 N2 C21 C7 -2.81(17) . . . . ?
C14 C7 C21 N2 126.67(14) . . . . ?
C8 C7 C21 N2 -121.01(14) . . . . ?
C6 C7 C21 N2 -5.08(16) . . . . ?
C23 O3 C22 O4 -0.1(2) . . . . ?
C23 O3 C22 C5 176.03(12) . . . . ?
N2 C5 C22 O4 61.39(17) . . . . ?
C4 C5 C22 O4 -178.97(14) . . . . ?
C6 C5 C22 O4 -51.02(19) . . . . ?
N2 C5 C22 O3 -114.88(13) . . . . ?
C4 C5 C22 O3 4.76(17) . . . . ?
C6 C5 C22 O3 132.72(12) . . . . ?
C25 O6 C24 O5 4.7(2) . . . . ?
C25 O6 C24 C6 -178.61(12) . . . . ?
C7 C6 C24 O5 -132.57(16) . . . . ?
C5 C6 C24 O5 -5.4(2) . . . . ?
C7 C6 C24 O6 50.80(16) . . . . ?
C5 C6 C24 O6 177.96(11) . . . . ?
C24 O6 C25 C26 88.73(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.052

# Attachment 'web_deposit_cif_file_2_Liang-LiangWang_1319125903.cu_1847_5_Cu_0m.cif'

data_cu_1847_5_cu_0m
_database_code_depnum_ccdc_archive 'CCDC 849674'
#TrackingRef 'web_deposit_cif_file_2_Liang-LiangWang_1319125903.cu_1847_5_Cu_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H28 N2 O7'
_chemical_formula_sum            'C27 H28 N2 O7'
_chemical_formula_weight         492.51
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   12.0989(2)
_cell_length_b                   12.7731(2)
_cell_length_c                   16.3369(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2524.71(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      5.42
_cell_measurement_theta_max      69.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11751
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.42
_diffrn_reflns_theta_max         69.52
_reflns_number_total             4463
_reflns_number_gt                4463
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0427P)^2^+0.4879P] where P=(Fo^2^+2Fc^2^)/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       0.0116(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_number_reflns         4463
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_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
O1 O 0.82751(9) -0.12697(8) 0.91659(6) 0.0186(2) Uani 1 1 d . . .
O2 O 0.64623(9) -0.14956(8) 0.88762(7) 0.0222(2) Uani 1 1 d . . .
O3 O 0.90168(9) 0.06794(8) 0.90484(6) 0.0215(2) Uani 1 1 d . . .
O4 O 0.67084(10) 0.26884(8) 0.93467(7) 0.0215(2) Uani 1 1 d . . .
O5 O 0.71310(10) 0.42521(8) 0.87896(7) 0.0238(2) Uani 1 1 d . . .
O6 O 0.89253(9) 0.50788(8) 0.73708(7) 0.0211(2) Uani 1 1 d . . .
O7 O 0.75899(10) 0.39634(9) 0.70052(7) 0.0252(3) Uani 1 1 d . . .
N1 N 0.73508(10) 0.00224(10) 0.85358(7) 0.0152(3) Uani 1 1 d . . .
N2 N 0.93575(11) 0.25414(10) 0.72871(7) 0.0172(3) Uani 1 1 d . . .
C1 C 1.19010(14) 0.44907(12) 0.91904(10) 0.0241(3) Uani 1 1 d . . .
H1 H 1.2534 0.4719 0.9485 0.029 Uiso 1 1 calc R . .
C2 C 1.08492(15) 0.46469(12) 0.95084(10) 0.0243(3) Uani 1 1 d . . .
H2A H 1.0760 0.5003 1.0014 0.029 Uiso 1 1 calc R . .
C3 C 0.99267(13) 0.42827(12) 0.90881(9) 0.0211(3) Uani 1 1 d . . .
H3 H 0.9211 0.4383 0.9313 0.025 Uiso 1 1 calc R . .
C4 C 1.00441(13) 0.37712(11) 0.83381(9) 0.0173(3) Uani 1 1 d . . .
C5 C 0.90262(12) 0.33320(11) 0.79033(8) 0.0156(3) Uani 1 1 d . . .
C6 C 0.82492(12) 0.27326(11) 0.85045(8) 0.0145(3) Uani 1 1 d . . .
H6 H 0.8727 0.2525 0.8977 0.017 Uiso 1 1 calc R . .
C7 C 0.79405(12) 0.16915(11) 0.80657(8) 0.0153(3) Uani 1 1 d . . .
C8 C 0.82152(12) 0.07479(11) 0.86220(8) 0.0152(3) Uani 1 1 d . . .
C9 C 0.73034(12) -0.09925(11) 0.88784(8) 0.0152(3) Uani 1 1 d . . .
C10 C 0.84170(13) -0.22883(12) 0.96050(9) 0.0205(3) Uani 1 1 d . . .
C11 C 0.96267(15) -0.22428(15) 0.98351(10) 0.0281(4) Uani 1 1 d . . .
H11A H 1.0077 -0.2207 0.9337 0.042 Uiso 1 1 calc R . .
H11B H 0.9824 -0.2872 1.0146 0.042 Uiso 1 1 calc R . .
H11C H 0.9763 -0.1620 1.0171 0.042 Uiso 1 1 calc R . .
C12 C 0.76821(15) -0.23025(15) 1.03567(10) 0.0289(4) Uani 1 1 d . . .
H12A H 0.7836 -0.1684 1.0693 0.043 Uiso 1 1 calc R . .
H12B H 0.7830 -0.2937 1.0676 0.043 Uiso 1 1 calc R . .
H12C H 0.6905 -0.2295 1.0187 0.043 Uiso 1 1 calc R . .
C13 C 0.87770(12) 0.17210(11) 0.73690(9) 0.0164(3) Uani 1 1 d . . .
H13 H 0.8861 0.1144 0.7008 0.020 Uiso 1 1 calc R . .
C14 C 0.72956(12) 0.33334(11) 0.88735(8) 0.0165(3) Uani 1 1 d . . .
C15 C 0.57276(14) 0.31156(13) 0.97450(10) 0.0256(4) Uani 1 1 d . . .
H15A H 0.5820 0.3878 0.9828 0.031 Uiso 1 1 calc R . .
H15B H 0.5629 0.2784 1.0288 0.031 Uiso 1 1 calc R . .
C16 C 0.47248(16) 0.29126(19) 0.92229(11) 0.0393(5) Uani 1 1 d . . .
H16A H 0.4789 0.3304 0.8709 0.059 Uiso 1 1 calc R . .
H16B H 0.4060 0.3139 0.9516 0.059 Uiso 1 1 calc R . .
H16C H 0.4673 0.2162 0.9103 0.059 Uiso 1 1 calc R . .
C17 C 1.20197(14) 0.39976(12) 0.84372(10) 0.0236(3) Uani 1 1 d . . .
H17 H 1.2736 0.3899 0.8211 0.028 Uiso 1 1 calc R . .
C18 C 1.10932(14) 0.36478(11) 0.80125(9) 0.0203(3) Uani 1 1 d . . .
H18 H 1.1181 0.3321 0.7494 0.024 Uiso 1 1 calc R . .
C19 C 0.84085(13) 0.41591(11) 0.73857(8) 0.0166(3) Uani 1 1 d . . .
C20 C 0.84273(15) 0.58415(12) 0.68299(11) 0.0265(4) Uani 1 1 d . . .
H20A H 0.8347 0.5539 0.6282 0.040 Uiso 1 1 calc R . .
H20B H 0.8899 0.6464 0.6801 0.040 Uiso 1 1 calc R . .
H20C H 0.7698 0.6039 0.7041 0.040 Uiso 1 1 calc R . .
C21 C 0.67780(12) 0.14561(11) 0.77881(8) 0.0157(3) Uani 1 1 d . . .
C22 C 0.64720(12) 0.04641(11) 0.80598(8) 0.0150(3) Uani 1 1 d . . .
C23 C 0.54551(13) 0.00316(12) 0.78615(9) 0.0201(3) Uani 1 1 d . . .
H23 H 0.5253 -0.0647 0.8047 0.024 Uiso 1 1 calc R . .
C24 C 0.47409(13) 0.06249(13) 0.73809(9) 0.0214(3) Uani 1 1 d . . .
H24 H 0.4042 0.0344 0.7232 0.026 Uiso 1 1 calc R . .
C25 C 0.50311(13) 0.16171(13) 0.71165(9) 0.0208(3) Uani 1 1 d . . .
H25 H 0.4527 0.2011 0.6794 0.025 Uiso 1 1 calc R . .
C26 C 0.60568(13) 0.20443(12) 0.73194(8) 0.0178(3) Uani 1 1 d . . .
H26 H 0.6256 0.2726 0.7139 0.021 Uiso 1 1 calc R . .
C27 C 0.81878(17) -0.31865(13) 0.90247(12) 0.0325(4) Uani 1 1 d . . .
H27A H 0.7405 -0.3182 0.8871 0.049 Uiso 1 1 calc R . .
H27B H 0.8366 -0.3850 0.9295 0.049 Uiso 1 1 calc R . .
H27C H 0.8644 -0.3109 0.8533 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0188(5) 0.0164(5) 0.0206(5) 0.0046(4) -0.0004(4) 0.0007(4)
O2 0.0210(5) 0.0185(5) 0.0270(5) 0.0056(4) -0.0045(4) -0.0036(4)
O3 0.0227(6) 0.0171(5) 0.0247(5) 0.0030(4) -0.0078(4) -0.0010(4)
O4 0.0245(6) 0.0200(5) 0.0200(5) 0.0012(4) 0.0080(4) 0.0006(4)
O5 0.0260(6) 0.0177(5) 0.0276(6) 0.0009(4) 0.0033(5) 0.0029(4)
O6 0.0233(6) 0.0153(5) 0.0246(5) 0.0055(4) -0.0048(4) -0.0030(4)
O7 0.0292(6) 0.0215(5) 0.0249(5) 0.0054(4) -0.0107(5) -0.0055(5)
N1 0.0158(6) 0.0148(6) 0.0149(5) 0.0000(4) -0.0014(5) 0.0001(5)
N2 0.0197(6) 0.0166(6) 0.0154(6) -0.0013(5) 0.0000(5) 0.0001(5)
C1 0.0248(8) 0.0191(7) 0.0282(8) 0.0029(6) -0.0107(6) -0.0047(6)
C2 0.0280(8) 0.0200(7) 0.0248(8) -0.0038(6) -0.0060(7) -0.0009(6)
C3 0.0221(8) 0.0195(7) 0.0218(7) -0.0034(6) -0.0031(6) -0.0003(6)
C4 0.0222(7) 0.0118(6) 0.0178(6) 0.0020(5) -0.0027(6) -0.0012(5)
C5 0.0186(7) 0.0145(6) 0.0138(6) -0.0007(5) 0.0006(5) -0.0004(6)
C6 0.0165(7) 0.0141(6) 0.0128(6) 0.0000(5) -0.0011(5) -0.0014(5)
C7 0.0180(7) 0.0136(6) 0.0143(6) -0.0012(5) -0.0014(6) 0.0004(5)
C8 0.0166(7) 0.0132(6) 0.0158(6) -0.0013(5) 0.0015(5) 0.0009(5)
C9 0.0174(7) 0.0150(6) 0.0131(6) -0.0019(5) 0.0005(5) 0.0004(5)
C10 0.0230(8) 0.0171(7) 0.0214(7) 0.0065(6) -0.0001(6) 0.0028(6)
C11 0.0234(8) 0.0332(9) 0.0277(8) 0.0112(7) -0.0005(6) 0.0044(7)
C12 0.0250(9) 0.0371(9) 0.0247(8) 0.0129(7) 0.0028(7) 0.0034(7)
C13 0.0178(7) 0.0166(7) 0.0148(6) -0.0020(5) -0.0023(5) 0.0003(5)
C14 0.0201(7) 0.0180(7) 0.0113(6) 0.0002(5) -0.0024(5) -0.0009(6)
C15 0.0274(9) 0.0281(8) 0.0214(7) -0.0025(6) 0.0089(7) 0.0036(6)
C16 0.0276(10) 0.0628(13) 0.0277(9) -0.0058(9) 0.0031(7) 0.0098(9)
C17 0.0197(8) 0.0226(7) 0.0286(8) 0.0055(6) -0.0008(6) -0.0021(6)
C18 0.0240(8) 0.0169(7) 0.0199(7) 0.0019(6) -0.0009(6) -0.0018(6)
C19 0.0211(7) 0.0158(7) 0.0130(6) -0.0007(5) 0.0014(5) -0.0020(6)
C20 0.0280(8) 0.0193(7) 0.0323(8) 0.0109(6) -0.0074(7) -0.0035(6)
C21 0.0184(7) 0.0168(6) 0.0120(6) -0.0027(5) 0.0012(5) -0.0005(5)
C22 0.0159(7) 0.0161(7) 0.0130(6) -0.0013(5) 0.0012(5) 0.0025(5)
C23 0.0208(8) 0.0181(7) 0.0213(7) 0.0001(6) -0.0013(6) -0.0023(6)
C24 0.0169(8) 0.0252(7) 0.0220(7) -0.0020(6) -0.0035(6) -0.0017(6)
C25 0.0196(7) 0.0243(8) 0.0184(7) 0.0016(6) -0.0044(6) 0.0025(6)
C26 0.0203(7) 0.0173(7) 0.0159(6) 0.0008(6) -0.0012(5) 0.0010(6)
C27 0.0426(10) 0.0175(7) 0.0375(9) 0.0007(7) -0.0055(8) 0.0055(7)

_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
O1 C9 1.3146(18) . ?
O1 C10 1.4956(17) . ?
O2 C9 1.2036(19) . ?
O3 C8 1.1973(19) . ?
O4 C14 1.3346(19) . ?
O4 C15 1.4592(18) . ?
O5 C14 1.1981(19) . ?
O6 C19 1.3310(18) . ?
O6 C20 1.4466(19) . ?
O7 C19 1.1957(19) . ?
N1 C8 1.4045(19) . ?
N1 C9 1.4132(18) . ?
N1 C22 1.4330(18) . ?
N2 C13 1.269(2) . ?
N2 C5 1.4812(18) . ?
C1 C2 1.389(3) . ?
C1 C17 1.390(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C18 1.385(2) . ?
C4 C5 1.528(2) . ?
C5 C19 1.546(2) . ?
C5 C6 1.5603(19) . ?
C6 C14 1.511(2) . ?
C6 C7 1.5562(18) . ?
C6 H6 1.0000 . ?
C7 C21 1.508(2) . ?
C7 C13 1.524(2) . ?
C7 C8 1.5456(19) . ?
C10 C11 1.512(2) . ?
C10 C27 1.514(2) . ?
C10 C12 1.516(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C15 C16 1.506(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.392(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.383(2) . ?
C21 C22 1.393(2) . ?
C22 C23 1.387(2) . ?
C23 C24 1.392(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.396(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C9 O1 C10 120.55(11) . . ?
C14 O4 C15 117.41(12) . . ?
C19 O6 C20 114.20(12) . . ?
C8 N1 C9 126.57(12) . . ?
C8 N1 C22 110.32(12) . . ?
C9 N1 C22 123.09(12) . . ?
C13 N2 C5 109.98(12) . . ?
C2 C1 C17 119.40(15) . . ?
C2 C1 H1 120.3 . . ?
C17 C1 H1 120.3 . . ?
C1 C2 C3 120.18(14) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 C4 120.55(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C18 C4 C3 118.92(14) . . ?
C18 C4 C5 121.21(13) . . ?
C3 C4 C5 119.85(13) . . ?
N2 C5 C4 110.37(12) . . ?
N2 C5 C19 103.00(10) . . ?
C4 C5 C19 113.13(11) . . ?
N2 C5 C6 104.86(11) . . ?
C4 C5 C6 111.91(11) . . ?
C19 C5 C6 112.85(12) . . ?
C14 C6 C7 115.75(12) . . ?
C14 C6 C5 117.52(12) . . ?
C7 C6 C5 105.90(11) . . ?
C14 C6 H6 105.5 . . ?
C7 C6 H6 105.5 . . ?
C5 C6 H6 105.5 . . ?
C21 C7 C13 113.57(11) . . ?
C21 C7 C8 102.82(11) . . ?
C13 C7 C8 108.40(11) . . ?
C21 C7 C6 122.19(12) . . ?
C13 C7 C6 99.41(11) . . ?
C8 C7 C6 110.11(11) . . ?
O3 C8 N1 127.83(13) . . ?
O3 C8 C7 124.99(13) . . ?
N1 C8 C7 107.18(12) . . ?
O2 C9 O1 127.84(13) . . ?
O2 C9 N1 121.53(13) . . ?
O1 C9 N1 110.63(12) . . ?
O1 C10 C11 101.36(12) . . ?
O1 C10 C27 109.75(12) . . ?
C11 C10 C27 111.23(15) . . ?
O1 C10 C12 109.36(12) . . ?
C11 C10 C12 111.51(13) . . ?
C27 C10 C12 113.00(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C7 117.84(12) . . ?
N2 C13 H13 121.1 . . ?
C7 C13 H13 121.1 . . ?
O5 C14 O4 125.62(14) . . ?
O5 C14 C6 125.36(14) . . ?
O4 C14 C6 108.91(12) . . ?
O4 C15 C16 109.78(14) . . ?
O4 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
O4 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 C17 C18 120.24(15) . . ?
C1 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C4 C18 C17 120.66(14) . . ?
C4 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
O7 C19 O6 124.34(13) . . ?
O7 C19 C5 122.81(13) . . ?
O6 C19 C5 112.72(12) . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 120.20(14) . . ?
C26 C21 C7 130.29(14) . . ?
C22 C21 C7 109.48(13) . . ?
C23 C22 C21 121.58(14) . . ?
C23 C22 N1 128.91(13) . . ?
C21 C22 N1 109.50(13) . . ?
C22 C23 C24 117.74(14) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C25 C24 C23 121.14(15) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 120.62(14) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 118.70(14) . . ?
C21 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C10 C27 H27A 109.5 . . ?
C10 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C10 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
C17 C1 C2 C3 2.0(2) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C3 C4 C18 -1.1(2) . . . . ?
C2 C3 C4 C5 177.22(14) . . . . ?
C13 N2 C5 C4 131.29(13) . . . . ?
C13 N2 C5 C19 -107.66(13) . . . . ?
C13 N2 C5 C6 10.61(15) . . . . ?
C18 C4 C5 N2 16.98(18) . . . . ?
C3 C4 C5 N2 -161.27(13) . . . . ?
C18 C4 C5 C19 -97.83(16) . . . . ?
C3 C4 C5 C19 83.92(16) . . . . ?
C18 C4 C5 C6 133.35(14) . . . . ?
C3 C4 C5 C6 -44.91(18) . . . . ?
N2 C5 C6 C14 -145.39(12) . . . . ?
C4 C5 C6 C14 94.95(14) . . . . ?
C19 C5 C6 C14 -34.03(16) . . . . ?
N2 C5 C6 C7 -14.26(14) . . . . ?
C4 C5 C6 C7 -133.92(12) . . . . ?
C19 C5 C6 C7 97.11(13) . . . . ?
C14 C6 C7 C21 18.63(18) . . . . ?
C5 C6 C7 C21 -113.50(14) . . . . ?
C14 C6 C7 C13 144.30(12) . . . . ?
C5 C6 C7 C13 12.18(14) . . . . ?
C14 C6 C7 C8 -102.02(13) . . . . ?
C5 C6 C7 C8 125.85(12) . . . . ?
C9 N1 C8 O3 -6.7(2) . . . . ?
C22 N1 C8 O3 171.51(14) . . . . ?
C9 N1 C8 C7 174.26(12) . . . . ?
C22 N1 C8 C7 -7.54(14) . . . . ?
C21 C7 C8 O3 -170.79(13) . . . . ?
C13 C7 C8 O3 68.69(17) . . . . ?
C6 C7 C8 O3 -39.09(19) . . . . ?
C21 C7 C8 N1 8.30(14) . . . . ?
C13 C7 C8 N1 -112.22(12) . . . . ?
C6 C7 C8 N1 139.99(12) . . . . ?
C10 O1 C9 O2 -4.7(2) . . . . ?
C10 O1 C9 N1 176.27(11) . . . . ?
C8 N1 C9 O2 168.45(13) . . . . ?
C22 N1 C9 O2 -9.5(2) . . . . ?
C8 N1 C9 O1 -12.45(18) . . . . ?
C22 N1 C9 O1 169.57(12) . . . . ?
C9 O1 C10 C11 -178.31(12) . . . . ?
C9 O1 C10 C27 64.00(17) . . . . ?
C9 O1 C10 C12 -60.48(17) . . . . ?
C5 N2 C13 C7 -2.54(18) . . . . ?
C21 C7 C13 N2 124.81(14) . . . . ?
C8 C7 C13 N2 -121.60(14) . . . . ?
C6 C7 C13 N2 -6.60(17) . . . . ?
C15 O4 C14 O5 5.3(2) . . . . ?
C15 O4 C14 C6 -178.44(12) . . . . ?
C7 C6 C14 O5 -132.15(15) . . . . ?
C5 C6 C14 O5 -5.7(2) . . . . ?
C7 C6 C14 O4 51.60(16) . . . . ?
C5 C6 C14 O4 178.06(11) . . . . ?
C14 O4 C15 C16 93.52(17) . . . . ?
C2 C1 C17 C18 -1.1(2) . . . . ?
C3 C4 C18 C17 2.0(2) . . . . ?
C5 C4 C18 C17 -176.24(13) . . . . ?
C1 C17 C18 C4 -1.0(2) . . . . ?
C20 O6 C19 O7 -1.5(2) . . . . ?
C20 O6 C19 C5 174.42(12) . . . . ?
N2 C5 C19 O7 61.27(17) . . . . ?
C4 C5 C19 O7 -179.58(13) . . . . ?
C6 C5 C19 O7 -51.24(18) . . . . ?
N2 C5 C19 O6 -114.68(13) . . . . ?
C4 C5 C19 O6 4.47(17) . . . . ?
C6 C5 C19 O6 132.81(12) . . . . ?
C13 C7 C21 C26 -67.60(19) . . . . ?
C8 C7 C21 C26 175.50(14) . . . . ?
C6 C7 C21 C26 51.4(2) . . . . ?
C13 C7 C21 C22 110.59(13) . . . . ?
C8 C7 C21 C22 -6.31(14) . . . . ?
C6 C7 C21 C22 -130.37(13) . . . . ?
C26 C21 C22 C23 1.0(2) . . . . ?
C7 C21 C22 C23 -177.36(13) . . . . ?
C26 C21 C22 N1 -179.47(12) . . . . ?
C7 C21 C22 N1 2.13(15) . . . . ?
C8 N1 C22 C23 -176.98(14) . . . . ?
C9 N1 C22 C23 1.3(2) . . . . ?
C8 N1 C22 C21 3.58(15) . . . . ?
C9 N1 C22 C21 -178.15(12) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
N1 C22 C23 C24 -179.61(14) . . . . ?
C22 C23 C24 C25 -0.6(2) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C22 C21 C26 C25 -1.0(2) . . . . ?
C7 C21 C26 C25 177.04(14) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        69.52
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.072