#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/64/1516493.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1516493
loop_
_publ_author_name
'Yan, Meng-Hong'
'Cheng, Pi'
'Jiang, Zhi-Yong'
'Ma, Yun-Bao'
'Zhang, Xue-Mei'
'Zhang, Feng-Xue'
'Yang, Liu-Meng'
'Zheng, Yong-Tang'
'Chen, Ji-Jun'
_publ_section_title
;
 Periglaucines A-D, anti-HBV and -HIV-1 alkaloids from Pericampylus
 glaucus.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              760
_journal_page_last               763
_journal_paper_doi               10.1021/np070479+
_journal_volume                  71
_journal_year                    2008
_chemical_formula_sum            'C20 H23 N O6'
_chemical_formula_weight         373.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2062(13)
_cell_length_b                   12.5950(14)
_cell_length_c                   12.8803(15)
_cell_measurement_temperature    571(2)
_cell_volume                     1818.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11500
_diffrn_reflns_theta_full        27.14
_diffrn_reflns_theta_max         27.14
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.101
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.7(16)
_refine_ls_extinction_coef       0.0050(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.0080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1522
_reflns_number_gt                2527
_reflns_number_total             3994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np070479%2B%2B-file001.cif
_cod_data_source_block           061219b
_cod_database_code               1516493
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.36586(18) 0.9813(2) 0.1350(2) 0.0810(8) Uani 1 1 d .
O2 O 1.4011(2) 0.9161(2) 0.2987(3) 0.0916(9) Uani 1 1 d .
O3 O 0.90093(17) 0.83879(15) 0.35923(15) 0.0503(5) Uani 1 1 d .
O4 O 0.69600(17) 0.86781(16) 0.35563(15) 0.0533(5) Uani 1 1 d .
O5 O 0.69002(17) 0.80036(17) 0.15450(16) 0.0561(6) Uani 1 1 d .
O6 O 0.9659(3) 0.7563(2) 0.0968(2) 0.0904(9) Uani 1 1 d .
N1 N 0.7273(2) 1.05436(19) 0.2369(2) 0.0531(7) Uani 1 1 d .
C17 C 1.4480(3) 0.9186(4) 0.1911(4) 0.0958(14) Uani 1 1 d .
C3 C 1.2587(3) 0.9722(3) 0.1885(3) 0.0628(9) Uani 1 1 d .
C2 C 1.2801(3) 0.9358(3) 0.2859(3) 0.0655(9) Uani 1 1 d .
C1 C 1.1906(3) 0.9227(3) 0.3566(3) 0.0609(9) Uani 1 1 d .
H1B H 1.2095 0.9657 0.4169 0.073 Uiso 1 1 calc R
H1A H 1.1914 0.8491 0.3788 0.073 Uiso 1 1 calc R
C11 C 1.0744(2) 0.9477(2) 0.3255(2) 0.0509(8) Uani 1 1 d .
C12 C 1.0520(2) 0.9857(2) 0.2255(2) 0.0471(7) Uani 1 1 d .
C4 C 1.1473(3) 0.9997(3) 0.1568(3) 0.0590(9) Uani 1 1 d .
H4A H 1.1297 0.9596 0.0944 0.071 Uiso 1 1 calc R
H4B H 1.1492 1.0741 0.1373 0.071 Uiso 1 1 calc R
C13 C 0.9256(2) 1.0075(2) 0.1902(2) 0.0469(7) Uani 1 1 d .
C15 C 0.9047(3) 1.1238(3) 0.1600(3) 0.0642(9) Uani 1 1 d .
H15A H 0.9478 1.1711 0.2062 0.077 Uiso 1 1 calc R
H15B H 0.9304 1.1369 0.0893 0.077 Uiso 1 1 calc R
C16 C 0.7732(3) 1.1395(3) 0.1703(3) 0.0830(13) Uani 1 1 d .
H16A H 0.7565 1.2082 0.2012 0.100 Uiso 1 1 calc R
H16B H 0.7355 1.1367 0.1026 0.100 Uiso 1 1 calc R
C14 C 0.8281(2) 0.9910(2) 0.2757(2) 0.0435(7) Uani 1 1 d .
C5 C 0.8959(3) 0.9354(3) 0.0959(2) 0.0546(8) Uani 1 1 d .
H5A H 0.8178 0.9535 0.0686 0.066 Uiso 1 1 calc R
H5B H 0.9543 0.9461 0.0414 0.066 Uiso 1 1 calc R
C6 C 0.8972(3) 0.8228(3) 0.1299(2) 0.0512(8) Uani 1 1 d .
C7 C 0.8009(3) 0.7955(2) 0.2071(2) 0.0456(7) Uani 1 1 d .
H7A H 0.8137 0.7232 0.2329 0.055 Uiso 1 1 calc R
C10 C 0.9683(3) 0.9316(3) 0.3947(2) 0.0531(8) Uani 1 1 d .
H10A H 0.9928 0.9234 0.4673 0.064 Uiso 1 1 calc R
C9 C 0.8823(3) 1.0229(2) 0.3825(2) 0.0554(8) Uani 1 1 d .
H9A H 0.9230 1.0908 0.3795 0.066 Uiso 1 1 calc R
H9B H 0.8228 1.0241 0.4371 0.066 Uiso 1 1 calc R
C8 C 0.8028(2) 0.8720(2) 0.2974(2) 0.0426(7) Uani 1 1 d .
C18 C 0.6708(4) 0.7134(3) 0.0860(3) 0.0851(12) Uani 1 1 d .
H18A H 0.5943 0.7209 0.0532 0.128 Uiso 1 1 calc R
H18B H 0.6728 0.6482 0.1246 0.128 Uiso 1 1 calc R
H18C H 0.7321 0.7125 0.0340 0.128 Uiso 1 1 calc R
C19 C 0.6606(3) 0.7648(2) 0.3888(3) 0.0693(10) Uani 1 1 d .
H19A H 0.5873 0.7697 0.4270 0.104 Uiso 1 1 calc R
H19B H 0.7215 0.7351 0.4324 0.104 Uiso 1 1 calc R
H19C H 0.6492 0.7200 0.3293 0.104 Uiso 1 1 calc R
C20 C 0.6422(3) 1.0946(3) 0.3130(3) 0.0783(12) Uani 1 1 d .
H20A H 0.5800 1.1328 0.2780 0.118 Uiso 1 1 calc R
H20B H 0.6825 1.1413 0.3604 0.118 Uiso 1 1 calc R
H20C H 0.6082 1.0362 0.3507 0.118 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 C17 105.3(3)
C2 O2 C17 103.4(3)
C8 O3 C10 109.8(2)
C8 O4 C19 115.4(2)
C7 O5 C18 113.4(2)
C20 N1 C16 111.6(3)
C20 N1 C14 117.5(3)
C16 N1 C14 109.1(2)
O1 C17 O2 105.0(3)
C2 C3 C4 121.7(3)
C2 C3 O1 109.5(3)
C4 C3 O1 128.7(3)
C3 C2 C1 121.9(3)
C3 C2 O2 110.1(3)
C1 C2 O2 128.0(4)
C2 C1 C11 117.8(3)
C12 C11 C1 120.5(3)
C12 C11 C10 116.9(2)
C1 C11 C10 122.6(3)
C11 C12 C4 119.3(3)
C11 C12 C13 120.5(2)
C4 C12 C13 120.1(3)
C3 C4 C12 118.7(3)
C12 C13 C15 113.1(3)
C12 C13 C5 109.3(2)
C15 C13 C5 109.1(3)
C12 C13 C14 114.7(2)
C15 C13 C14 101.4(2)
C5 C13 C14 108.8(2)
C16 C15 C13 104.8(3)
N1 C16 C15 107.5(3)
N1 C14 C8 116.4(2)
N1 C14 C9 117.5(3)
C8 C14 C9 99.3(2)
N1 C14 C13 103.0(2)
C8 C14 C13 112.5(2)
C9 C14 C13 108.3(2)
C6 C5 C13 109.0(2)
O6 C6 C5 124.2(3)
O6 C6 C7 121.8(3)
C5 C6 C7 113.9(3)
O5 C7 C6 107.6(2)
O5 C7 C8 110.6(2)
C6 C7 C8 110.6(2)
O3 C10 C11 109.4(2)
O3 C10 C9 104.3(2)
C11 C10 C9 110.0(3)
C10 C9 C14 98.4(2)
O4 C8 O3 110.3(2)
O4 C8 C7 111.9(2)
O3 C8 C7 104.7(2)
O4 C8 C14 106.7(2)
O3 C8 C14 104.1(2)
C7 C8 C14 118.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.389(4)
O1 C17 1.412(5)
O2 C2 1.388(4)
O2 C17 1.482(6)
O3 C8 1.421(3)
O3 C10 1.464(4)
O4 C8 1.413(3)
O4 C19 1.422(3)
O5 C7 1.417(3)
O5 C18 1.422(4)
O6 C6 1.215(4)
N1 C20 1.458(4)
N1 C16 1.466(4)
N1 C14 1.470(3)
C3 C2 1.357(5)
C3 C4 1.359(4)
C2 C1 1.365(4)
C1 C11 1.399(4)
C11 C12 1.397(4)
C11 C10 1.500(4)
C12 C4 1.398(4)
C12 C13 1.513(4)
C13 C15 1.533(4)
C13 C5 1.553(4)
C13 C14 1.566(4)
C15 C16 1.493(4)
C14 C8 1.551(4)
C14 C9 1.555(4)
C5 C6 1.484(5)
C6 C7 1.507(4)
C7 C8 1.510(4)
C10 C9 1.508(4)
