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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_2015543_0m
_database_code_depnum_ccdc_archive 'CCDC 1454990'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Sanguinarine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O5'
_chemical_formula_weight         363.36

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   12.3648(3)
_cell_length_b                   7.7330(2)
_cell_length_c                   19.4502(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.4400(10)
_cell_angle_gamma                90.00
_cell_volume                     1693.12(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    8658
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      66.99

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.849
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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 APXII-CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49382
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         67.83
_reflns_number_total             3071
_reflns_number_gt                2656
_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)+(0.0467P)²+0.6064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3071
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.46107(11) 0.76000(17) 0.39540(6) 0.0483(3) Uani 1 1 d . . .
O2 O 0.38595(11) 0.67331(17) 0.48098(6) 0.0468(3) Uani 1 1 d . . .
O3 O 0.95797(10) 0.70640(15) 0.98404(5) 0.0372(3) Uani 1 1 d . . .
O4 O 1.14137(10) 0.84383(16) 1.03592(6) 0.0454(3) Uani 1 1 d . . .
O5 O 0.80877(9) 0.54343(13) 0.80514(6) 0.0336(3) Uani 1 1 d . . .
N1 N 0.69893(11) 0.79660(16) 0.75237(6) 0.0288(3) Uani 1 1 d . . .
C1 C 0.65017(15) 0.8694(2) 0.48986(8) 0.0367(4) Uani 1 1 d . . .
H14 H 0.6785 0.9057 0.4548 0.044 Uiso 1 1 calc R . .
C2 C 0.54191(15) 0.7963(2) 0.46755(8) 0.0361(4) Uani 1 1 d . . .
C3 C 0.49652(14) 0.7433(2) 0.51916(8) 0.0347(4) Uani 1 1 d . . .
C4 C 0.55790(13) 0.75983(19) 0.59506(8) 0.0318(3) Uani 1 1 d . . .
H16 H 0.5257 0.7243 0.6283 0.038 Uiso 1 1 calc R . .
C5 C 0.67375(13) 0.83387(18) 0.62179(8) 0.0288(3) Uani 1 1 d . . .
C6 C 0.74753(13) 0.85031(18) 0.70042(8) 0.0281(3) Uani 1 1 d . . .
C7 C 0.78443(13) 0.71580(19) 0.82031(8) 0.0292(3) Uani 1 1 d . . .
H17 H 0.7509 0.7122 0.8580 0.035 Uiso 1 1 calc R . .
C8 C 0.90157(13) 0.80804(18) 0.85382(8) 0.0283(3) Uani 1 1 d . . .
C9 C 0.97670(13) 0.79686(18) 0.92929(8) 0.0294(3) Uani 1 1 d . . .
C10 C 1.08548(14) 0.87935(19) 0.95967(8) 0.0331(3) Uani 1 1 d . . .
C11 C 1.12418(14) 0.9808(2) 0.91683(9) 0.0372(4) Uani 1 1 d . . .
H13 H 1.1964 1.0390 0.9379 0.045 Uiso 1 1 calc R . .
C12 C 1.04985(14) 0.99301(19) 0.83965(9) 0.0349(4) Uani 1 1 d . . .
H12 H 1.0740 1.0598 0.8088 0.042 Uiso 1 1 calc R . .
C13 C 0.94065(13) 0.90776(18) 0.80786(8) 0.0293(3) Uani 1 1 d . . .
C14 C 0.86342(13) 0.91016(18) 0.72580(8) 0.0283(3) Uani 1 1 d . . .
C15 C 0.90650(14) 0.96426(19) 0.67245(9) 0.0331(3) Uani 1 1 d . . .
H11 H 0.9838 1.0057 0.6890 0.040 Uiso 1 1 calc R . .
C16 C 0.83599(14) 0.9564(2) 0.59674(8) 0.0342(3) Uani 1 1 d . . .
H10 H 0.8654 0.9964 0.5627 0.041 Uiso 1 1 calc R . .
C17 C 0.72006(14) 0.88930(19) 0.56912(8) 0.0312(3) Uani 1 1 d . . .
C18 C 0.35919(16) 0.6900(2) 0.40218(8) 0.0422(4) Uani 1 1 d . . .
H1 H 0.3398 0.5778 0.3778 0.051 Uiso 1 1 calc R . .
H15 H 0.2915 0.7660 0.3780 0.051 Uiso 1 1 calc R . .
C19 C 1.06568(14) 0.7264(2) 1.05124(8) 0.0374(4) Uani 1 1 d . . .
H2 H 1.0476 0.7704 1.0920 0.045 Uiso 1 1 calc R . .
H3 H 1.1049 0.6153 1.0665 0.045 Uiso 1 1 calc R . .
C20 C 0.62617(15) 0.9282(2) 0.76701(9) 0.0422(4) Uani 1 1 d . . .
H7 H 0.6766 1.0170 0.7986 0.063 Uiso 1 1 calc R . .
H8 H 0.5817 0.8760 0.7920 0.063 Uiso 1 1 calc R . .
H9 H 0.5724 0.9779 0.7201 0.063 Uiso 1 1 calc R . .
C21 C 0.70942(16) 0.4313(2) 0.78597(9) 0.0458(4) Uani 1 1 d . . .
H4 H 0.6891 0.4203 0.8284 0.069 Uiso 1 1 calc R . .
H5 H 0.7290 0.3195 0.7729 0.069 Uiso 1 1 calc R . .
H6 H 0.6431 0.4782 0.7437 0.069 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
O1 C2 1.3736(18) . ?
O1 C18 1.426(2) . ?
O2 C3 1.369(2) . ?
O2 C18 1.4338(18) . ?
O3 C9 1.3714(18) . ?
O3 C19 1.4372(18) . ?
O4 C10 1.3800(18) . ?
O4 C19 1.422(2) . ?
O5 C21 1.4218(19) . ?
O5 C7 1.4241(18) . ?
N1 C6 1.4343(17) . ?
N1 C7 1.4486(18) . ?
N1 C20 1.462(2) . ?
C1 C2 1.349(2) . ?
C1 C17 1.430(2) . ?
C1 H14 0.9300 . ?
C2 C3 1.399(2) . ?
C3 C4 1.358(2) . ?
C4 C5 1.426(2) . ?
C4 H16 0.9300 . ?
C5 C6 1.426(2) . ?
C5 C17 1.431(2) . ?
C6 C14 1.388(2) . ?
C7 C8 1.500(2) . ?
C7 H17 0.9800 . ?
C8 C9 1.377(2) . ?
C8 C13 1.409(2) . ?
C9 C10 1.381(2) . ?
C10 C11 1.367(2) . ?
C11 C12 1.402(2) . ?
C11 H13 0.9300 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.483(2) . ?
C14 C15 1.412(2) . ?
C15 C16 1.367(2) . ?
C15 H11 0.9300 . ?
C16 C17 1.405(2) . ?
C16 H10 0.9300 . ?
C18 H1 0.9700 . ?
C18 H15 0.9700 . ?
C19 H2 0.9700 . ?
C19 H3 0.9700 . ?
C20 H7 0.9600 . ?
C20 H8 0.9600 . ?
C20 H9 0.9600 . ?
C21 H4 0.9600 . ?
C21 H5 0.9600 . ?
C21 H6 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C18 106.28(12) . . ?
C3 O2 C18 106.34(13) . . ?
C9 O3 C19 105.12(12) . . ?
C10 O4 C19 105.79(12) . . ?
C21 O5 C7 113.06(12) . . ?
C6 N1 C7 114.03(11) . . ?
C6 N1 C20 113.99(12) . . ?
C7 N1 C20 113.46(11) . . ?
C2 C1 C17 117.95(14) . . ?
C2 C1 H14 121.0 . . ?
C17 C1 H14 121.0 . . ?
C1 C2 O1 128.34(14) . . ?
C1 C2 C3 122.10(14) . . ?
O1 C2 C3 109.55(14) . . ?
C4 C3 O2 127.63(14) . . ?
C4 C3 C2 122.86(15) . . ?
O2 C3 C2 109.50(13) . . ?
C3 C4 C5 117.35(14) . . ?
C3 C4 H16 121.3 . . ?
C5 C4 H16 121.3 . . ?
C4 C5 C6 121.82(13) . . ?
C4 C5 C17 119.90(13) . . ?
C6 C5 C17 118.25(14) . . ?
C14 C6 C5 121.30(13) . . ?
C14 C6 N1 121.19(13) . . ?
C5 C6 N1 117.46(13) . . ?
O5 C7 N1 110.59(11) . . ?
O5 C7 C8 106.64(11) . . ?
N1 C7 C8 113.60(12) . . ?
O5 C7 H17 108.6 . . ?
N1 C7 H17 108.6 . . ?
C8 C7 H17 108.6 . . ?
C9 C8 C13 116.97(13) . . ?
C9 C8 C7 122.51(13) . . ?
C13 C8 C7 120.50(13) . . ?
O3 C9 C10 110.54(12) . . ?
O3 C9 C8 127.12(14) . . ?
C10 C9 C8 122.34(14) . . ?
C11 C10 C9 121.93(14) . . ?
C11 C10 O4 128.56(14) . . ?
C9 C10 O4 109.50(13) . . ?
C10 C11 C12 116.83(14) . . ?
C10 C11 H13 121.6 . . ?
C12 C11 H13 121.6 . . ?
C13 C12 C11 121.87(14) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C8 120.01(13) . . ?
C12 C13 C14 123.02(13) . . ?
C8 C13 C14 116.92(13) . . ?
C6 C14 C15 119.04(14) . . ?
C6 C14 C13 119.28(13) . . ?
C15 C14 C13 121.61(14) . . ?
C16 C15 C14 120.80(15) . . ?
C16 C15 H11 119.6 . . ?
C14 C15 H11 119.6 . . ?
C15 C16 C17 121.55(13) . . ?
C15 C16 H10 119.2 . . ?
C17 C16 H10 119.2 . . ?
C16 C17 C5 118.94(13) . . ?
C16 C17 C1 121.19(14) . . ?
C5 C17 C1 119.82(14) . . ?
O1 C18 O2 108.12(13) . . ?
O1 C18 H1 110.1 . . ?
O2 C18 H1 110.1 . . ?
O1 C18 H15 110.1 . . ?
O2 C18 H15 110.1 . . ?
H1 C18 H15 108.4 . . ?
O4 C19 O3 108.70(12) . . ?
O4 C19 H2 109.9 . . ?
O3 C19 H2 109.9 . . ?
O4 C19 H3 109.9 . . ?
O3 C19 H3 109.9 . . ?
H2 C19 H3 108.3 . . ?
N1 C20 H7 109.5 . . ?
N1 C20 H8 109.5 . . ?
H7 C20 H8 109.5 . . ?
N1 C20 H9 109.5 . . ?
H7 C20 H9 109.5 . . ?
H8 C20 H9 109.5 . . ?
O5 C21 H4 109.5 . . ?
O5 C21 H5 109.5 . . ?
H4 C21 H5 109.5 . . ?
O5 C21 H6 109.5 . . ?
H4 C21 H6 109.5 . . ?
H5 C21 H6 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 O1 -178.10(14) . . . . ?
C17 C1 C2 C3 1.1(2) . . . . ?
C18 O1 C2 C1 -177.69(16) . . . . ?
C18 O1 C2 C3 3.05(17) . . . . ?
C18 O2 C3 C4 178.47(16) . . . . ?
C18 O2 C3 C2 -2.47(18) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
O1 C2 C3 C4 178.75(14) . . . . ?
C1 C2 C3 O2 -179.68(14) . . . . ?
O1 C2 C3 O2 -0.37(18) . . . . ?
O2 C3 C4 C5 178.53(14) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 -177.31(13) . . . . ?
C3 C4 C5 C17 0.8(2) . . . . ?
C4 C5 C6 C14 174.96(13) . . . . ?
C17 C5 C6 C14 -3.2(2) . . . . ?
C4 C5 C6 N1 -2.8(2) . . . . ?
C17 C5 C6 N1 179.05(12) . . . . ?
C7 N1 C6 C14 -33.96(19) . . . . ?
C20 N1 C6 C14 98.54(16) . . . . ?
C7 N1 C6 C5 143.79(13) . . . . ?
C20 N1 C6 C5 -83.72(17) . . . . ?
C21 O5 C7 N1 -66.80(14) . . . . ?
C21 O5 C7 C8 169.24(11) . . . . ?
C6 N1 C7 O5 -76.19(15) . . . . ?
C20 N1 C7 O5 151.07(13) . . . . ?
C6 N1 C7 C8 43.68(17) . . . . ?
C20 N1 C7 C8 -89.07(15) . . . . ?
O5 C7 C8 C9 -82.96(16) . . . . ?
N1 C7 C8 C9 154.95(13) . . . . ?
O5 C7 C8 C13 95.43(15) . . . . ?
N1 C7 C8 C13 -26.65(19) . . . . ?
C19 O3 C9 C10 -3.73(16) . . . . ?
C19 O3 C9 C8 175.90(14) . . . . ?
C13 C8 C9 O3 -179.29(14) . . . . ?
C7 C8 C9 O3 -0.8(2) . . . . ?
C13 C8 C9 C10 0.3(2) . . . . ?
C7 C8 C9 C10 178.75(13) . . . . ?
O3 C9 C10 C11 -178.80(14) . . . . ?
C8 C9 C10 C11 1.6(2) . . . . ?
O3 C9 C10 O4 0.21(17) . . . . ?
C8 C9 C10 O4 -179.43(13) . . . . ?
C19 O4 C10 C11 -177.62(16) . . . . ?
C19 O4 C10 C9 3.45(17) . . . . ?
C9 C10 C11 C12 -2.1(2) . . . . ?
O4 C10 C11 C12 179.13(15) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C8 1.0(2) . . . . ?
C11 C12 C13 C14 -176.40(14) . . . . ?
C9 C8 C13 C12 -1.5(2) . . . . ?
C7 C8 C13 C12 -179.98(13) . . . . ?
C9 C8 C13 C14 176.02(12) . . . . ?
C7 C8 C13 C14 -2.5(2) . . . . ?
C5 C6 C14 C15 3.4(2) . . . . ?
N1 C6 C14 C15 -178.95(13) . . . . ?
C5 C6 C14 C13 -173.66(12) . . . . ?
N1 C6 C14 C13 4.0(2) . . . . ?
C12 C13 C14 C6 -168.07(14) . . . . ?
C8 C13 C14 C6 14.5(2) . . . . ?
C12 C13 C14 C15 15.0(2) . . . . ?
C8 C13 C14 C15 -162.48(14) . . . . ?
C6 C14 C15 C16 -0.7(2) . . . . ?
C13 C14 C15 C16 176.28(13) . . . . ?
C14 C15 C16 C17 -2.2(2) . . . . ?
C15 C16 C17 C5 2.3(2) . . . . ?
C15 C16 C17 C1 -175.20(14) . . . . ?
C4 C5 C17 C16 -177.83(13) . . . . ?
C6 C5 C17 C16 0.4(2) . . . . ?
C4 C5 C17 C1 -0.3(2) . . . . ?
C6 C5 C17 C1 177.89(13) . . . . ?
C2 C1 C17 C16 176.83(14) . . . . ?
C2 C1 C17 C5 -0.6(2) . . . . ?
C2 O1 C18 O2 -4.54(17) . . . . ?
C3 O2 C18 O1 4.33(18) . . . . ?
C10 O4 C19 O3 -5.75(16) . . . . ?
C9 O3 C19 O4 5.84(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.83
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_2015459_0m
_database_code_depnum_ccdc_archive 'CCDC 1454991'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Sanguinarine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O5'
_chemical_formula_weight         363.36
_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'

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                   7.7154(2)
_cell_length_b                   9.5901(3)
_cell_length_c                   22.5595(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1669.21(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4034
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      59.65

_exptl_crystal_description       polyhedral
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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 APXII-CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18142
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         63.43
_reflns_number_total             2707
_reflns_number_gt                2457
_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)+(0.0454P)²+0.1136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0058(5)
_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(2)
_refine_ls_number_reflns         2707
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O2 O 0.1124(2) 0.47576(15) 0.08793(6) 0.0409(4) Uani 1 1 d . . .
O3 O 0.1056(2) 0.28810(14) 0.50313(6) 0.0429(4) Uani 1 1 d . . .
O4 O 0.2191(2) 0.09752(16) 0.55281(7) 0.0519(5) Uani 1 1 d . . .
O5 O 0.23497(19) 0.45042(13) 0.37991(6) 0.0324(4) Uani 1 1 d . . .
O1 O 0.2840(2) 0.32174(16) 0.03591(6) 0.0427(4) Uani 1 1 d . . .
N1 N 0.0835(2) 0.31290(16) 0.30874(7) 0.0299(4) Uani 1 1 d . . .
C18 C 0.1501(3) 0.4226(3) 0.02998(10) 0.0459(6) Uani 1 1 d . . .
H1 H 0.0474 0.3801 0.0130 0.055 Uiso 1 1 calc R . .
H13 H 0.1875 0.4976 0.0041 0.055 Uiso 1 1 calc R . .
C3 C 0.1721(3) 0.3742(2) 0.12628(9) 0.0337(5) Uani 1 1 d . . .
C4 C 0.1446(3) 0.3633(2) 0.18526(9) 0.0323(5) Uani 1 1 d . . .
H14 H 0.0729 0.4256 0.2052 0.039 Uiso 1 1 calc R . .
C5 C 0.2306(3) 0.2518(2) 0.21594(9) 0.0314(5) Uani 1 1 d . . .
C6 C 0.2067(3) 0.2283(2) 0.27774(10) 0.0303(5) Uani 1 1 d . . .
C14 C 0.3005(3) 0.1265(2) 0.30719(10) 0.0348(5) Uani 1 1 d . . .
C13 C 0.2768(3) 0.1063(2) 0.37150(10) 0.0355(5) Uani 1 1 d . . .
C8 C 0.1908(3) 0.2130(2) 0.40277(9) 0.0316(5) Uani 1 1 d . . .
C9 C 0.1779(3) 0.1961(2) 0.46317(9) 0.0346(5) Uani 1 1 d . . .
C19 C 0.1310(4) 0.2261(2) 0.55965(10) 0.0466(6) Uani 1 1 d . . .
H2 H 0.1986 0.2880 0.5846 0.056 Uiso 1 1 calc R . .
H17 H 0.0199 0.2106 0.5786 0.056 Uiso 1 1 calc R . .
C10 C 0.2437(3) 0.0829(2) 0.49226(10) 0.0389(5) Uani 1 1 d . . .
C20 C -0.0981(3) 0.2794(2) 0.29609(9) 0.0389(5) Uani 1 1 d . . .
H4 H -0.1142 0.2718 0.2540 0.058 Uiso 1 1 calc R . .
H3 H -0.1712 0.3520 0.3113 0.058 Uiso 1 1 calc R . .
H5 H -0.1277 0.1925 0.3146 0.058 Uiso 1 1 calc R . .
C7 C 0.1168(3) 0.3374(2) 0.37114(9) 0.0297(5) Uani 1 1 d . . .
H9 H 0.0067 0.3618 0.3902 0.036 Uiso 1 1 calc R . .
C21 C 0.1552(3) 0.5811(2) 0.36646(11) 0.0451(6) Uani 1 1 d . . .
H6 H 0.1203 0.5820 0.3256 0.068 Uiso 1 1 calc R . .
H7 H 0.2363 0.6552 0.3734 0.068 Uiso 1 1 calc R . .
H8 H 0.0553 0.5938 0.3913 0.068 Uiso 1 1 calc R . .
C2 C 0.2790(3) 0.2824(2) 0.09492(9) 0.0352(5) Uani 1 1 d . . .
C1 C 0.3673(3) 0.1790(2) 0.12172(10) 0.0386(5) Uani 1 1 d . . .
H12 H 0.4401 0.1204 0.1003 0.046 Uiso 1 1 calc R . .
C17 C 0.3452(3) 0.1626(2) 0.18393(10) 0.0343(5) Uani 1 1 d . . .
C16 C 0.4387(3) 0.0598(2) 0.21509(10) 0.0413(6) Uani 1 1 d . . .
H11 H 0.5144 0.0018 0.1946 0.050 Uiso 1 1 calc R . .
C15 C 0.4201(3) 0.0440(2) 0.27475(10) 0.0411(5) Uani 1 1 d . . .
H10 H 0.4869 -0.0219 0.2945 0.049 Uiso 1 1 calc R . .
C12 C 0.3388(3) -0.0105(2) 0.40152(11) 0.0422(6) Uani 1 1 d . . .
H16 H 0.3917 -0.0815 0.3801 0.051 Uiso 1 1 calc R . .
C11 C 0.3237(3) -0.0237(2) 0.46285(11) 0.0457(6) Uani 1 1 d . . .
H15 H 0.3661 -0.1014 0.4828 0.055 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
O2 C3 1.382(3) . ?
O2 C18 1.433(2) . ?
O3 C9 1.379(3) . ?
O3 C19 1.421(3) . ?
O4 C10 1.386(3) . ?
O4 C19 1.416(3) . ?
O5 C21 1.429(2) . ?
O5 C7 1.430(2) . ?
O1 C2 1.384(3) . ?
O1 C18 1.422(3) . ?
N1 C6 1.432(2) . ?
N1 C7 1.450(3) . ?
N1 C20 1.465(3) . ?
C18 H1 0.9700 . ?
C18 H13 0.9700 . ?
C3 C4 1.351(3) . ?
C3 C2 1.398(3) . ?
C4 C5 1.436(3) . ?
C4 H14 0.9300 . ?
C5 C6 1.424(3) . ?
C5 C17 1.426(3) . ?
C6 C14 1.385(3) . ?
C14 C15 1.419(3) . ?
C14 C13 1.475(3) . ?
C13 C12 1.393(3) . ?
C13 C8 1.410(3) . ?
C8 C9 1.376(3) . ?
C8 C7 1.503(3) . ?
C9 C10 1.367(3) . ?
C19 H2 0.9700 . ?
C19 H17 0.9700 . ?
C10 C11 1.366(3) . ?
C20 H4 0.9600 . ?
C20 H3 0.9600 . ?
C20 H5 0.9600 . ?
C7 H9 0.9800 . ?
C21 H6 0.9600 . ?
C21 H7 0.9600 . ?
C21 H8 0.9600 . ?
C2 C1 1.347(3) . ?
C1 C17 1.423(3) . ?
C1 H12 0.9300 . ?
C17 C16 1.410(3) . ?
C16 C15 1.362(3) . ?
C16 H11 0.9300 . ?
C15 H10 0.9300 . ?
C12 C11 1.394(3) . ?
C12 H16 0.9300 . ?
C11 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C18 104.65(16) . . ?
C9 O3 C19 105.26(16) . . ?
C10 O4 C19 105.15(16) . . ?
C21 O5 C7 111.13(16) . . ?
C2 O1 C18 104.81(17) . . ?
C6 N1 C7 116.63(16) . . ?
C6 N1 C20 114.53(16) . . ?
C7 N1 C20 113.20(16) . . ?
O1 C18 O2 107.67(18) . . ?
O1 C18 H1 110.2 . . ?
O2 C18 H1 110.2 . . ?
O1 C18 H13 110.2 . . ?
O2 C18 H13 110.2 . . ?
H1 C18 H13 108.5 . . ?
C4 C3 O2 128.2(2) . . ?
C4 C3 C2 122.8(2) . . ?
O2 C3 C2 108.88(18) . . ?
C3 C4 C5 117.37(19) . . ?
C3 C4 H14 121.3 . . ?
C5 C4 H14 121.3 . . ?
C6 C5 C17 118.73(19) . . ?
C6 C5 C4 122.01(18) . . ?
C17 C5 C4 119.25(19) . . ?
C14 C6 C5 120.90(18) . . ?
C14 C6 N1 120.81(19) . . ?
C5 C6 N1 118.29(17) . . ?
C6 C14 C15 119.0(2) . . ?
C6 C14 C13 119.98(19) . . ?
C15 C14 C13 121.0(2) . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 C14 122.8(2) . . ?
C8 C13 C14 117.06(18) . . ?
C9 C8 C13 116.36(18) . . ?
C9 C8 C7 122.45(19) . . ?
C13 C8 C7 121.19(18) . . ?
C10 C9 C8 122.8(2) . . ?
C10 C9 O3 110.18(18) . . ?
C8 C9 O3 126.95(18) . . ?
O4 C19 O3 109.43(18) . . ?
O4 C19 H2 109.8 . . ?
O3 C19 H2 109.8 . . ?
O4 C19 H17 109.8 . . ?
O3 C19 H17 109.8 . . ?
H2 C19 H17 108.2 . . ?
C11 C10 C9 122.0(2) . . ?
C11 C10 O4 128.06(19) . . ?
C9 C10 O4 109.97(19) . . ?
N1 C20 H4 109.5 . . ?
N1 C20 H3 109.5 . . ?
H4 C20 H3 109.5 . . ?
N1 C20 H5 109.5 . . ?
H4 C20 H5 109.5 . . ?
H3 C20 H5 109.5 . . ?
O5 C7 N1 111.72(15) . . ?
O5 C7 C8 107.08(16) . . ?
N1 C7 C8 113.55(16) . . ?
O5 C7 H9 108.1 . . ?
N1 C7 H9 108.1 . . ?
C8 C7 H9 108.1 . . ?
O5 C21 H6 109.5 . . ?
O5 C21 H7 109.5 . . ?
H6 C21 H7 109.5 . . ?
O5 C21 H8 109.5 . . ?
H6 C21 H8 109.5 . . ?
H7 C21 H8 109.5 . . ?
C1 C2 O1 128.19(19) . . ?
C1 C2 C3 122.3(2) . . ?
O1 C2 C3 109.36(19) . . ?
C2 C1 C17 117.61(19) . . ?
C2 C1 H12 121.2 . . ?
C17 C1 H12 121.2 . . ?
C16 C17 C1 120.51(19) . . ?
C16 C17 C5 118.97(19) . . ?
C1 C17 C5 120.5(2) . . ?
C15 C16 C17 121.1(2) . . ?
C15 C16 H11 119.5 . . ?
C17 C16 H11 119.5 . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H10 119.4 . . ?
C14 C15 H10 119.4 . . ?
C13 C12 C11 121.8(2) . . ?
C13 C12 H16 119.1 . . ?
C11 C12 H16 119.1 . . ?
C10 C11 C12 116.87(19) . . ?
C10 C11 H15 121.6 . . ?
C12 C11 H15 121.6 . . ?

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
C2 O1 C18 O2 20.3(2) . . . . ?
C3 O2 C18 O1 -21.5(2) . . . . ?
C18 O2 C3 C4 -169.0(2) . . . . ?
C18 O2 C3 C2 14.4(2) . . . . ?
O2 C3 C4 C5 -176.19(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -178.1(2) . . . . ?
C3 C4 C5 C17 2.7(3) . . . . ?
C17 C5 C6 C14 4.0(3) . . . . ?
C4 C5 C6 C14 -175.26(19) . . . . ?
C17 C5 C6 N1 -176.27(17) . . . . ?
C4 C5 C6 N1 4.5(3) . . . . ?
C7 N1 C6 C14 28.7(3) . . . . ?
C20 N1 C6 C14 -106.8(2) . . . . ?
C7 N1 C6 C5 -151.11(18) . . . . ?
C20 N1 C6 C5 73.4(2) . . . . ?
C5 C6 C14 C15 -0.8(3) . . . . ?
N1 C6 C14 C15 179.40(19) . . . . ?
C5 C6 C14 C13 178.51(18) . . . . ?
N1 C6 C14 C13 -1.3(3) . . . . ?
C6 C14 C13 C12 166.6(2) . . . . ?
C15 C14 C13 C12 -14.1(3) . . . . ?
C6 C14 C13 C8 -14.9(3) . . . . ?
C15 C14 C13 C8 164.4(2) . . . . ?
C12 C13 C8 C9 1.9(3) . . . . ?
C14 C13 C8 C9 -176.62(19) . . . . ?
C12 C13 C8 C7 -177.7(2) . . . . ?
C14 C13 C8 C7 3.8(3) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C10 179.6(2) . . . . ?
C13 C8 C9 O3 177.5(2) . . . . ?
C7 C8 C9 O3 -2.9(3) . . . . ?
C19 O3 C9 C10 0.4(2) . . . . ?
C19 O3 C9 C8 -177.4(2) . . . . ?
C10 O4 C19 O3 -0.7(2) . . . . ?
C9 O3 C19 O4 0.2(2) . . . . ?
C8 C9 C10 C11 -1.7(4) . . . . ?
O3 C9 C10 C11 -179.6(2) . . . . ?
C8 C9 C10 O4 177.07(19) . . . . ?
O3 C9 C10 O4 -0.8(3) . . . . ?
C19 O4 C10 C11 179.6(2) . . . . ?
C19 O4 C10 C9 0.9(2) . . . . ?
C21 O5 C7 N1 71.6(2) . . . . ?
C21 O5 C7 C8 -163.50(17) . . . . ?
C6 N1 C7 O5 83.64(19) . . . . ?
C20 N1 C7 O5 -140.29(16) . . . . ?
C6 N1 C7 C8 -37.6(2) . . . . ?
C20 N1 C7 C8 98.5(2) . . . . ?
C9 C8 C7 O5 78.6(2) . . . . ?
C13 C8 C7 O5 -101.8(2) . . . . ?
C9 C8 C7 N1 -157.6(2) . . . . ?
C13 C8 C7 N1 22.0(3) . . . . ?
C18 O1 C2 C1 172.3(2) . . . . ?
C18 O1 C2 C3 -11.4(2) . . . . ?
C4 C3 C2 C1 -2.3(3) . . . . ?
O2 C3 C2 C1 174.55(18) . . . . ?
C4 C3 C2 O1 -178.84(19) . . . . ?
O2 C3 C2 O1 -2.0(2) . . . . ?
O1 C2 C1 C17 177.48(19) . . . . ?
C3 C2 C1 C17 1.6(3) . . . . ?
C2 C1 C17 C16 -177.60(19) . . . . ?
C2 C1 C17 C5 1.1(3) . . . . ?
C6 C5 C17 C16 -3.8(3) . . . . ?
C4 C5 C17 C16 175.44(18) . . . . ?
C6 C5 C17 C1 177.45(19) . . . . ?
C4 C5 C17 C1 -3.3(3) . . . . ?
C1 C17 C16 C15 179.3(2) . . . . ?
C5 C17 C16 C15 0.5(3) . . . . ?
C17 C16 C15 C14 2.7(3) . . . . ?
C6 C14 C15 C16 -2.6(3) . . . . ?
C13 C14 C15 C16 178.1(2) . . . . ?
C8 C13 C12 C11 -2.2(3) . . . . ?
C14 C13 C12 C11 176.2(2) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
O4 C10 C11 C12 -177.1(2) . . . . ?
C13 C12 C11 C10 0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        63.43
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_2015598_0m
_database_code_depnum_ccdc_archive 'CCDC 1454992'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Sanguinarine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O5'
_chemical_formula_weight         363.36
_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'

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

_cell_length_a                   7.7230(2)
_cell_length_b                   9.6004(3)
_cell_length_c                   22.5562(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1672.40(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    8951
_cell_measurement_theta_min      5.01
_cell_measurement_theta_max      67.45

_exptl_crystal_description       polyhedral
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(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 APXII-CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13140
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         5.01
_diffrn_reflns_theta_max         68.02
_reflns_number_total             3019
_reflns_number_gt                2957
_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+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.02(15)
_refine_ls_number_reflns         3019
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
O2 O 0.88767(16) 0.52441(12) 0.91197(4) 0.0430(3) Uani 1 1 d . . .
O1 O 0.71604(15) 0.67845(12) 0.96397(5) 0.0454(3) Uani 1 1 d . . .
O5 O 0.76519(13) 0.54928(9) 0.62006(4) 0.0349(2) Uani 1 1 d . . .
C2 C 0.72072(18) 0.71781(15) 0.90535(6) 0.0379(3) Uani 1 1 d . . .
C1 C 0.63219(19) 0.82125(15) 0.87836(7) 0.0409(3) Uani 1 1 d . . .
H5 H 0.5574 0.8809 0.9001 0.049 Uiso 1 1 calc R . .
C9 C 0.82212(19) 0.80319(15) 0.53681(7) 0.0377(3) Uani 1 1 d . . .
N1 N 0.91622(15) 0.68706(11) 0.69121(5) 0.0326(3) Uani 1 1 d . . .
C17 C 0.65493(18) 0.83777(14) 0.81597(7) 0.0367(3) Uani 1 1 d . . .
O4 O 0.78081(16) 0.90227(13) 0.44735(5) 0.0539(3) Uani 1 1 d . . .
C15 C 0.5794(2) 0.95644(15) 0.72535(7) 0.0433(3) Uani 1 1 d . . .
H10 H 0.5111 1.0236 0.7051 0.052 Uiso 1 1 calc R . .
C11 C 0.6755(2) 1.02398(17) 0.53717(8) 0.0493(4) Uani 1 1 d . . .
H11 H 0.6320 1.1034 0.5169 0.059 Uiso 1 1 calc R . .
O3 O 0.89463(16) 0.71171(11) 0.49687(5) 0.0459(3) Uani 1 1 d . . .
C6 C 0.79399(17) 0.77133(13) 0.72225(6) 0.0333(3) Uani 1 1 d . . .
C3 C 0.82753(18) 0.62528(15) 0.87371(6) 0.0362(3) Uani 1 1 d . . .
C16 C 0.5609(2) 0.94070(15) 0.78491(7) 0.0434(3) Uani 1 1 d . . .
H15 H 0.4837 0.9998 0.8059 0.052 Uiso 1 1 calc R . .
C7 C 0.88342(17) 0.66238(13) 0.62889(6) 0.0318(3) Uani 1 1 d . . .
H16 H 0.9957 0.6376 0.6095 0.038 Uiso 1 1 calc R . .
C5 C 0.76960(17) 0.74767(14) 0.78404(6) 0.0330(3) Uani 1 1 d . . .
C8 C 0.80892(17) 0.78702(14) 0.59721(6) 0.0347(3) Uani 1 1 d . . .
C14 C 0.69943(18) 0.87399(14) 0.69281(7) 0.0372(3) Uani 1 1 d . . .
C12 C 0.6605(2) 1.01017(16) 0.59823(8) 0.0459(4) Uani 1 1 d . . .
H20 H 0.6058 1.0823 0.6201 0.055 Uiso 1 1 calc R . .
C13 C 0.72354(17) 0.89351(14) 0.62856(7) 0.0377(3) Uani 1 1 d . . .
C10 C 0.7561(2) 0.91710(16) 0.50734(7) 0.0420(3) Uani 1 1 d . . .
C4 C 0.85534(18) 0.63636(14) 0.81463(6) 0.0348(3) Uani 1 1 d . . .
H23 H 0.9287 0.5730 0.7943 0.042 Uiso 1 1 calc R . .
C20 C 1.09849(19) 0.72069(16) 0.70381(6) 0.0405(3) Uani 1 1 d . . .
H24A H 1.1293 0.8084 0.6842 0.061 Uiso 1 1 calc R . .
H24B H 1.1729 0.6458 0.6889 0.061 Uiso 1 1 calc R . .
H24C H 1.1147 0.7303 0.7467 0.061 Uiso 1 1 calc R . .
C21 C 0.8446(2) 0.41905(15) 0.63358(7) 0.0454(4) Uani 1 1 d . . .
H25A H 0.9495 0.4079 0.6096 0.068 Uiso 1 1 calc R . .
H25B H 0.7637 0.3432 0.6247 0.068 Uiso 1 1 calc R . .
H25C H 0.8750 0.4164 0.6757 0.068 Uiso 1 1 calc R . .
C19 C 0.8688(2) 0.77380(18) 0.44028(7) 0.0502(4) Uani 1 1 d . . .
H26A H 0.9820 0.7897 0.4208 0.060 Uiso 1 1 calc R . .
H26B H 0.7997 0.7107 0.4149 0.060 Uiso 1 1 calc R . .
C18 C 0.8507(2) 0.57703(19) 0.96998(7) 0.0480(4) Uani 1 1 d . . .
H27A H 0.8125 0.5005 0.9963 0.058 Uiso 1 1 calc R . .
H27B H 0.9554 0.6203 0.9873 0.058 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
O2 C3 1.3779(18) . ?
O2 C18 1.4313(17) . ?
O1 C2 1.3758(18) . ?
O1 C18 1.431(2) . ?
O5 C21 1.4254(16) . ?
O5 C7 1.4326(16) . ?
C2 C1 1.351(2) . ?
C2 C3 1.407(2) . ?
C1 C17 1.427(2) . ?
C1 H5 0.9500 . ?
C9 C8 1.3750(19) . ?
C9 O3 1.3771(19) . ?
C9 C10 1.378(2) . ?
N1 C6 1.4268(17) . ?
N1 C7 1.4480(16) . ?
N1 C20 1.4719(18) . ?
C17 C16 1.412(2) . ?
C17 C5 1.4323(18) . ?
O4 C10 1.3740(19) . ?
O4 C19 1.417(2) . ?
C15 C16 1.359(2) . ?
C15 C14 1.423(2) . ?
C15 H10 0.9500 . ?
C11 C10 1.376(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
O3 C19 1.4228(17) . ?
C6 C14 1.395(2) . ?
C6 C5 1.425(2) . ?
C3 C4 1.3539(19) . ?
C16 H15 0.9500 . ?
C7 C8 1.5077(17) . ?
C7 H16 1.0000 . ?
C5 C4 1.434(2) . ?
C8 C13 1.407(2) . ?
C14 C13 1.473(2) . ?
C12 C13 1.400(2) . ?
C12 H20 0.9500 . ?
C4 H23 0.9500 . ?
C20 H24A 0.9800 . ?
C20 H24B 0.9800 . ?
C20 H24C 0.9800 . ?
C21 H25A 0.9800 . ?
C21 H25B 0.9800 . ?
C21 H25C 0.9800 . ?
C19 H26A 0.9900 . ?
C19 H26B 0.9900 . ?
C18 H27A 0.9900 . ?
C18 H27B 0.9900 . ?

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
C3 O2 C18 104.90(12) . . ?
C2 O1 C18 105.00(11) . . ?
C21 O5 C7 111.16(10) . . ?
C1 C2 O1 128.45(13) . . ?
C1 C2 C3 122.18(14) . . ?
O1 C2 C3 109.25(13) . . ?
C2 C1 C17 117.63(12) . . ?
C2 C1 H5 121.2 . . ?
C17 C1 H5 121.2 . . ?
C8 C9 O3 127.33(13) . . ?
C8 C9 C10 122.71(14) . . ?
O3 C9 C10 109.94(13) . . ?
C6 N1 C7 116.96(11) . . ?
C6 N1 C20 114.43(11) . . ?
C7 N1 C20 113.00(11) . . ?
C16 C17 C1 120.25(13) . . ?
C16 C17 C5 119.40(14) . . ?
C1 C17 C5 120.33(13) . . ?
C10 O4 C19 105.51(12) . . ?
C16 C15 C14 121.09(14) . . ?
C16 C15 H10 119.5 . . ?
C14 C15 H10 119.5 . . ?
C10 C11 C12 116.83(14) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
C9 O3 C19 105.23(11) . . ?
C14 C6 C5 120.61(12) . . ?
C14 C6 N1 120.89(13) . . ?
C5 C6 N1 118.49(12) . . ?
C4 C3 O2 128.19(13) . . ?
C4 C3 C2 122.87(14) . . ?
O2 C3 C2 108.88(12) . . ?
C15 C16 C17 120.94(13) . . ?
C15 C16 H15 119.5 . . ?
C17 C16 H15 119.5 . . ?
O5 C7 N1 111.74(10) . . ?
O5 C7 C8 107.01(10) . . ?
N1 C7 C8 113.39(11) . . ?
O5 C7 H16 108.2 . . ?
N1 C7 H16 108.2 . . ?
C8 C7 H16 108.2 . . ?
C6 C5 C17 118.52(13) . . ?
C6 C5 C4 121.91(12) . . ?
C17 C5 C4 119.57(13) . . ?
C9 C8 C13 116.78(13) . . ?
C9 C8 C7 122.06(13) . . ?
C13 C8 C7 121.16(12) . . ?
C6 C14 C15 119.24(14) . . ?
C6 C14 C13 119.48(13) . . ?
C15 C14 C13 121.27(14) . . ?
C11 C12 C13 122.17(15) . . ?
C11 C12 H20 118.9 . . ?
C13 C12 H20 118.9 . . ?
C12 C13 C8 119.91(14) . . ?
C12 C13 C14 122.60(14) . . ?
C8 C13 C14 117.46(12) . . ?
O4 C10 C11 128.43(14) . . ?
O4 C10 C9 109.98(14) . . ?
C11 C10 C9 121.57(14) . . ?
C3 C4 C5 117.32(13) . . ?
C3 C4 H23 121.3 . . ?
C5 C4 H23 121.3 . . ?
N1 C20 H24A 109.5 . . ?
N1 C20 H24B 109.5 . . ?
H24A C20 H24B 109.5 . . ?
N1 C20 H24C 109.5 . . ?
H24A C20 H24C 109.5 . . ?
H24B C20 H24C 109.5 . . ?
O5 C21 H25A 109.5 . . ?
O5 C21 H25B 109.5 . . ?
H25A C21 H25B 109.5 . . ?
O5 C21 H25C 109.5 . . ?
H25A C21 H25C 109.5 . . ?
H25B C21 H25C 109.5 . . ?
O4 C19 O3 109.32(13) . . ?
O4 C19 H26A 109.8 . . ?
O3 C19 H26A 109.8 . . ?
O4 C19 H26B 109.8 . . ?
O3 C19 H26B 109.8 . . ?
H26A C19 H26B 108.3 . . ?
O1 C18 O2 107.39(12) . . ?
O1 C18 H27A 110.2 . . ?
O2 C18 H27A 110.2 . . ?
O1 C18 H27B 110.2 . . ?
O2 C18 H27B 110.2 . . ?
H27A C18 H27B 108.5 . . ?

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
C18 O1 C2 C1 -172.45(14) . . . . ?
C18 O1 C2 C3 11.68(15) . . . . ?
O1 C2 C1 C17 -177.60(13) . . . . ?
C3 C2 C1 C17 -2.2(2) . . . . ?
C2 C1 C17 C16 177.63(12) . . . . ?
C2 C1 C17 C5 -0.6(2) . . . . ?
C8 C9 O3 C19 177.46(15) . . . . ?
C10 C9 O3 C19 -0.65(16) . . . . ?
C7 N1 C6 C14 -28.68(17) . . . . ?
C20 N1 C6 C14 106.76(15) . . . . ?
C7 N1 C6 C5 150.88(12) . . . . ?
C20 N1 C6 C5 -73.68(15) . . . . ?
C18 O2 C3 C4 168.61(15) . . . . ?
C18 O2 C3 C2 -14.05(16) . . . . ?
C1 C2 C3 C4 2.9(2) . . . . ?
O1 C2 C3 C4 179.05(12) . . . . ?
C1 C2 C3 O2 -174.65(12) . . . . ?
O1 C2 C3 O2 1.53(16) . . . . ?
C14 C15 C16 C17 -2.8(2) . . . . ?
C1 C17 C16 C15 -179.10(14) . . . . ?
C5 C17 C16 C15 -0.8(2) . . . . ?
C21 O5 C7 N1 -71.62(14) . . . . ?
C21 O5 C7 C8 163.71(11) . . . . ?
C6 N1 C7 O5 -83.64(14) . . . . ?
C20 N1 C7 O5 140.30(11) . . . . ?
C6 N1 C7 C8 37.39(16) . . . . ?
C20 N1 C7 C8 -98.66(13) . . . . ?
C14 C6 C5 C17 -4.24(19) . . . . ?
N1 C6 C5 C17 176.20(11) . . . . ?
C14 C6 C5 C4 175.34(12) . . . . ?
N1 C6 C5 C4 -4.22(18) . . . . ?
C16 C17 C5 C6 4.25(19) . . . . ?
C1 C17 C5 C6 -177.46(12) . . . . ?
C16 C17 C5 C4 -175.34(12) . . . . ?
C1 C17 C5 C4 2.95(19) . . . . ?
O3 C9 C8 C13 -177.87(14) . . . . ?
C10 C9 C8 C13 0.0(2) . . . . ?
O3 C9 C8 C7 2.7(2) . . . . ?
C10 C9 C8 C7 -179.37(14) . . . . ?
O5 C7 C8 C9 -78.61(15) . . . . ?
N1 C7 C8 C9 157.73(13) . . . . ?
O5 C7 C8 C13 102.03(14) . . . . ?
N1 C7 C8 C13 -21.63(17) . . . . ?
C5 C6 C14 C15 0.8(2) . . . . ?
N1 C6 C14 C15 -179.65(13) . . . . ?
C5 C6 C14 C13 -178.24(12) . . . . ?
N1 C6 C14 C13 1.31(19) . . . . ?
C16 C15 C14 C6 2.8(2) . . . . ?
C16 C15 C14 C13 -178.20(13) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C8 1.6(2) . . . . ?
C11 C12 C13 C14 -176.34(15) . . . . ?
C9 C8 C13 C12 -1.45(19) . . . . ?
C7 C8 C13 C12 177.95(14) . . . . ?
C9 C8 C13 C14 176.56(13) . . . . ?
C7 C8 C13 C14 -4.04(18) . . . . ?
C6 C14 C13 C12 -167.12(14) . . . . ?
C15 C14 C13 C12 13.9(2) . . . . ?
C6 C14 C13 C8 14.93(19) . . . . ?
C15 C14 C13 C8 -164.09(14) . . . . ?
C19 O4 C10 C11 -179.42(17) . . . . ?
C19 O4 C10 C9 -0.99(17) . . . . ?
C12 C11 C10 O4 176.98(15) . . . . ?
C12 C11 C10 C9 -1.3(2) . . . . ?
C8 C9 C10 O4 -177.15(13) . . . . ?
O3 C9 C10 O4 1.06(17) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
O3 C9 C10 C11 179.62(15) . . . . ?
O2 C3 C4 C5 176.57(13) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C6 C5 C4 C3 178.07(12) . . . . ?
C17 C5 C4 C3 -2.36(19) . . . . ?
C10 O4 C19 O3 0.58(17) . . . . ?
C9 O3 C19 O4 0.03(17) . . . . ?
C2 O1 C18 O2 -20.36(16) . . . . ?
C3 O2 C18 O1 21.28(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        68.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.234
