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


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       crystengcomm@rsc.org
loop_
_publ_author_name
'Caiqin Yang'
'Jing Wang'
'Zhenwei Zhang'
'Yanli Zeng'
'Yongli Wang'
_publ_contact_author_name        'Wang, Jing'

data_p-1
_database_code_depnum_ccdc_archive 'CCDC 802078'
#TrackingRef '- final-B-revision.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N2 O6'
_chemical_formula_weight         388.41

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4965(2)
_cell_length_b                   11.4692(4)
_cell_length_c                   12.3648(5)
_cell_angle_alpha                68.093(2)
_cell_angle_beta                 88.655(2)
_cell_angle_gamma                81.853(2)
_cell_volume                     975.89(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER-APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7394
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0700
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.46
_reflns_number_total             4401
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II'
_computing_cell_refinement       'APEX II'
_computing_data_reduction        'SAINT PLUS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  XCIF

_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^)+(0.1355P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.080(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4401
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.2265
_refine_ls_wR_factor_gt          0.1872
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0457(3) 0.6734(3) 0.8995(2) 0.0501(7) Uani 1 1 d . . .
C2 C -0.0111(3) 0.6476(2) 0.7993(2) 0.0464(6) Uani 1 1 d . . .
H2B H -0.1048 0.6579 0.7472 0.056 Uiso 1 1 calc R . .
C3 C 0.1626(3) 0.6067(2) 0.7777(2) 0.0411(6) Uani 1 1 d . . .
C4 C 0.2986(3) 0.5934(3) 0.8587(2) 0.0538(7) Uani 1 1 d . . .
H4A H 0.4172 0.5667 0.8454 0.065 Uiso 1 1 calc R . .
C5 C 0.2603(4) 0.6192(3) 0.9580(3) 0.0622(8) Uani 1 1 d . . .
H5A H 0.3533 0.6098 1.0103 0.075 Uiso 1 1 calc R . .
C6 C 0.0869(4) 0.6583(3) 0.9805(2) 0.0556(7) Uani 1 1 d . . .
H6A H 0.0599 0.6740 1.0480 0.067 Uiso 1 1 calc R . .
C7 C 0.2071(3) 0.5765(2) 0.6689(2) 0.0404(5) Uani 1 1 d . . .
H7A H 0.0949 0.5943 0.6229 0.049 Uiso 1 1 calc R . .
C8 C 0.2802(3) 0.4380(2) 0.7008(2) 0.0403(6) Uani 1 1 d . . .
C9 C 0.4615(3) 0.3994(2) 0.7092(2) 0.0422(6) Uani 1 1 d . . .
C10 C 0.5167(3) 0.6173(2) 0.6009(2) 0.0434(6) Uani 1 1 d . . .
C11 C 0.3371(3) 0.6614(2) 0.5942(2) 0.0413(6) Uani 1 1 d . . .
C12 C 0.5611(3) 0.2668(3) 0.7567(3) 0.0548(7) Uani 1 1 d . . .
H12A H 0.4763 0.2074 0.7825 0.082 Uiso 1 1 calc R . .
H12B H 0.6385 0.2571 0.8212 0.082 Uiso 1 1 calc R . .
H12C H 0.6324 0.2511 0.6967 0.082 Uiso 1 1 calc R . .
C13 C 0.6667(3) 0.6881(3) 0.5416(2) 0.0502(7) Uani 1 1 d . . .
H13A H 0.6185 0.7744 0.4955 0.075 Uiso 1 1 calc R . .
H13B H 0.7267 0.6484 0.4921 0.075 Uiso 1 1 calc R . .
H13C H 0.7512 0.6870 0.5993 0.075 Uiso 1 1 calc R . .
C14 C 0.1422(3) 0.3531(2) 0.7265(2) 0.0409(6) Uani 1 1 d . . .
C15 C 0.0663(3) 0.1453(3) 0.7849(3) 0.0562(7) Uani 1 1 d . . .
H15A H -0.0125 0.1651 0.7174 0.067 Uiso 1 1 calc R . .
H15B H -0.0064 0.1567 0.8472 0.067 Uiso 1 1 calc R . .
C16 C 0.1570(4) 0.0101(3) 0.8231(3) 0.0590(7) Uani 1 1 d . . .
H16A H 0.0611 -0.0435 0.8457 0.071 Uiso 1 1 calc R . .
C17 C 0.2527(5) -0.0174(4) 0.7250(3) 0.0835(11) Uani 1 1 d . . .
H17A H 0.1709 0.0081 0.6591 0.125 Uiso 1 1 calc R . .
H17B H 0.2949 -0.1067 0.7499 0.125 Uiso 1 1 calc R . .
H17C H 0.3534 0.0290 0.7035 0.125 Uiso 1 1 calc R . .
C18 C 0.2795(6) -0.0275(4) 0.9301(3) 0.0868(12) Uani 1 1 d . . .
H18A H 0.2133 -0.0088 0.9906 0.130 Uiso 1 1 calc R . .
H18B H 0.3798 0.0194 0.9106 0.130 Uiso 1 1 calc R . .
H18C H 0.3229 -0.1167 0.9570 0.130 Uiso 1 1 calc R . .
C19 C 0.2503(3) 0.7885(3) 0.5226(2) 0.0461(6) Uani 1 1 d . . .
C20 C 0.2766(5) 0.9990(3) 0.3988(3) 0.0768(10) Uani 1 1 d . . .
H20A H 0.3676 1.0519 0.3651 0.115 Uiso 1 1 calc R . .
H20B H 0.2018 1.0343 0.4464 0.115 Uiso 1 1 calc R . .
H20C H 0.2039 0.9948 0.3379 0.115 Uiso 1 1 calc R . .
N1 N -0.2318(3) 0.7174(3) 0.9199(2) 0.0658(7) Uani 1 1 d . . .
N2 N 0.5745(3) 0.4921(2) 0.66909(19) 0.0461(5) Uani 1 1 d . . .
H2A H 0.6873 0.4699 0.6881 0.055 Uiso 1 1 calc R . .
O1 O -0.2637(4) 0.7406(4) 1.0068(3) 0.1094(11) Uani 1 1 d . . .
O2 O -0.3485(3) 0.7291(3) 0.8481(3) 0.0921(9) Uani 1 1 d . . .
O3 O -0.0190(2) 0.39371(18) 0.72012(18) 0.0550(5) Uani 1 1 d . . .
O4 O 0.2021(2) 0.22996(16) 0.75587(16) 0.0473(5) Uani 1 1 d . . .
O5 O 0.3612(3) 0.87340(19) 0.46949(19) 0.0627(6) Uani 1 1 d . . .
O6 O 0.0880(3) 0.8176(2) 0.5115(2) 0.0731(7) 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
C1 0.0473(14) 0.0476(16) 0.0554(16) -0.0212(12) 0.0109(11) -0.0032(11)
C2 0.0375(12) 0.0504(15) 0.0501(14) -0.0193(12) 0.0019(10) -0.0016(10)
C3 0.0356(11) 0.0407(13) 0.0453(13) -0.0145(10) 0.0029(9) -0.0040(9)
C4 0.0387(13) 0.0666(19) 0.0570(16) -0.0269(14) -0.0023(11) 0.0008(11)
C5 0.0546(16) 0.080(2) 0.0567(17) -0.0325(15) -0.0085(13) -0.0037(14)
C6 0.0631(17) 0.0576(17) 0.0498(15) -0.0249(13) 0.0061(12) -0.0078(13)
C7 0.0284(10) 0.0457(14) 0.0455(13) -0.0164(10) 0.0001(9) -0.0013(9)
C8 0.0309(11) 0.0452(14) 0.0448(13) -0.0182(10) 0.0022(9) -0.0017(9)
C9 0.0326(11) 0.0463(14) 0.0452(13) -0.0159(11) -0.0001(9) -0.0003(10)
C10 0.0356(12) 0.0515(15) 0.0428(13) -0.0172(11) 0.0008(9) -0.0057(10)
C11 0.0365(12) 0.0440(14) 0.0426(13) -0.0161(10) 0.0006(9) -0.0031(10)
C12 0.0309(12) 0.0520(16) 0.0732(18) -0.0168(13) -0.0037(11) 0.0023(10)
C13 0.0366(12) 0.0556(17) 0.0542(15) -0.0155(12) 0.0042(10) -0.0076(11)
C14 0.0342(11) 0.0459(15) 0.0433(13) -0.0188(10) -0.0008(9) -0.0013(10)
C15 0.0399(13) 0.0519(17) 0.0771(19) -0.0231(14) 0.0033(12) -0.0105(11)
C16 0.0539(15) 0.0495(17) 0.0694(18) -0.0170(13) -0.0012(13) -0.0084(12)
C17 0.090(2) 0.069(2) 0.088(2) -0.0310(19) 0.010(2) 0.0042(18)
C18 0.100(3) 0.065(2) 0.080(2) -0.0081(18) -0.022(2) -0.0146(19)
C19 0.0403(13) 0.0490(15) 0.0460(14) -0.0154(11) 0.0005(10) -0.0033(10)
C20 0.076(2) 0.0483(18) 0.091(2) -0.0108(17) 0.0145(18) -0.0025(15)
N1 0.0539(15) 0.0753(18) 0.0702(17) -0.0331(14) 0.0140(12) -0.0007(12)
N2 0.0273(9) 0.0507(13) 0.0555(12) -0.0157(10) -0.0014(8) -0.0020(8)
O1 0.0856(18) 0.163(3) 0.0963(19) -0.082(2) 0.0202(15) 0.0204(18)
O2 0.0473(12) 0.135(2) 0.108(2) -0.0674(18) 0.0123(13) 0.0019(13)
O3 0.0303(9) 0.0538(11) 0.0801(13) -0.0256(10) 0.0023(8) -0.0018(7)
O4 0.0346(8) 0.0445(10) 0.0614(11) -0.0186(8) 0.0039(7) -0.0047(7)
O5 0.0526(11) 0.0482(12) 0.0747(13) -0.0099(10) 0.0094(9) -0.0044(9)
O6 0.0439(11) 0.0567(13) 0.0941(16) -0.0025(11) -0.0073(10) 0.0014(9)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.374(4) . ?
C1 C2 1.387(4) . ?
C1 N1 1.465(4) . ?
C2 C3 1.375(3) . ?
C3 C4 1.398(3) . ?
C3 C7 1.529(3) . ?
C4 C5 1.381(4) . ?
C5 C6 1.371(4) . ?
C7 C8 1.509(3) . ?
C7 C11 1.519(3) . ?
C8 C9 1.363(3) . ?
C8 C14 1.469(3) . ?
C9 N2 1.391(3) . ?
C9 C12 1.499(4) . ?
C10 C11 1.363(3) . ?
C10 N2 1.378(3) . ?
C10 C13 1.496(3) . ?
C11 C19 1.458(3) . ?
C14 O3 1.225(3) . ?
C14 O4 1.331(3) . ?
C15 O4 1.453(3) . ?
C15 C16 1.503(4) . ?
C16 C17 1.505(5) . ?
C16 C18 1.517(4) . ?
C19 O6 1.212(3) . ?
C19 O5 1.341(3) . ?
C20 O5 1.439(4) . ?
N1 O1 1.210(4) . ?
N1 O2 1.219(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.8(2) . . ?
C6 C1 N1 118.8(3) . . ?
C2 C1 N1 118.4(2) . . ?
C3 C2 C1 119.6(2) . . ?
C2 C3 C4 117.9(2) . . ?
C2 C3 C7 121.4(2) . . ?
C4 C3 C7 120.6(2) . . ?
C5 C4 C3 121.3(2) . . ?
C6 C5 C4 120.9(3) . . ?
C5 C6 C1 117.5(3) . . ?
C8 C7 C11 111.34(19) . . ?
C8 C7 C3 111.18(19) . . ?
C11 C7 C3 110.7(2) . . ?
C9 C8 C14 125.0(2) . . ?
C9 C8 C7 120.2(2) . . ?
C14 C8 C7 114.71(19) . . ?
C8 C9 N2 118.0(2) . . ?
C8 C9 C12 128.6(2) . . ?
N2 C9 C12 113.40(19) . . ?
C11 C10 N2 118.6(2) . . ?
C11 C10 C13 128.1(2) . . ?
N2 C10 C13 113.2(2) . . ?
C10 C11 C19 126.4(2) . . ?
C10 C11 C7 120.0(2) . . ?
C19 C11 C7 113.54(19) . . ?
O3 C14 O4 122.0(2) . . ?
O3 C14 C8 121.7(2) . . ?
O4 C14 C8 116.28(19) . . ?
O4 C15 C16 109.5(2) . . ?
C15 C16 C17 112.1(3) . . ?
C15 C16 C18 112.3(3) . . ?
C17 C16 C18 112.1(3) . . ?
O6 C19 O5 121.1(2) . . ?
O6 C19 C11 122.9(2) . . ?
O5 C19 C11 116.0(2) . . ?
O1 N1 O2 122.7(3) . . ?
O1 N1 C1 119.1(3) . . ?
O2 N1 C1 118.2(3) . . ?
C10 N2 C9 124.04(19) . . ?
C14 O4 C15 116.40(18) . . ?
C19 O5 C20 116.3(2) . . ?

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 H2A O3 0.86 2.24 3.089(2) 171.0 1_655

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.085