#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/87/1508752.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_1508752
loop_
_publ_author_name
'Wang, Xiao-Jing'
'Liu, Yun-Bao'
'Li, Li'
'Yu, Shi-Shan'
'Lv, Hai-Ning'
'Ma, Shuang-Gang'
'Bao, Xiu-Qi'
'Zhang, Dan'
'Qu, Jing'
'Li, Yong'
_publ_section_title
;
 Lycojaponicumins D and E: two new alkaloids from Lycopodium japonicum.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5688
_journal_page_last               5691
_journal_paper_doi               10.1021/ol302701y
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H23 N O3'
_chemical_formula_sum            'C17 H23 N O3'
_chemical_formula_weight         289.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   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                   6.3189(9)
_cell_length_b                   13.2585(19)
_cell_length_c                   17.498(3)
_cell_measurement_reflns_used    467
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.22
_cell_measurement_theta_min      3.12
_cell_volume                     1466.0(4)
_computing_cell_refinement       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_collection       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_reduction        'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10108
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.18
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.8299
_exptl_absorpt_correction_T_min  0.6981
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS by T.Higashi Jun 3, 2003'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0149(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0253P)²+0.3823P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0795
_reflns_number_gt                2581
_reflns_number_total             2665
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302701y_si_002.cif
_cod_data_source_block           sx2864
_cod_original_cell_volume        1465.9(4)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1508752
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
N1 N 0.2155(2) 0.20766(10) 0.77117(8) 0.0234(3) Uani 1 1 d .
O1 O 0.1661(2) 0.52120(9) 0.70865(7) 0.0322(3) Uani 1 1 d .
O2 O 0.02209(19) 0.62958(8) 0.84399(7) 0.0278(3) Uani 1 1 d .
H2OA H -0.0283 0.6398 0.8002 0.033 Uiso 1 1 d R
O3 O 0.71824(19) 0.36249(10) 0.89805(7) 0.0335(3) Uani 1 1 d .
C1 C 0.4066(3) 0.19755(13) 0.72381(10) 0.0263(4) Uani 1 1 d .
H1A H 0.3660 0.2075 0.6697 0.032 Uiso 1 1 calc R
H1B H 0.4598 0.1276 0.7289 0.032 Uiso 1 1 calc R
C2 C 0.5866(3) 0.26939(13) 0.74226(10) 0.0259(4) Uani 1 1 d .
H2A H 0.6990 0.2628 0.7032 0.031 Uiso 1 1 calc R
H2B H 0.6483 0.2517 0.7925 0.031 Uiso 1 1 calc R
C3 C 0.5066(3) 0.37809(12) 0.74405(10) 0.0232(4) Uani 1 1 d .
H3A H 0.4711 0.3992 0.6913 0.028 Uiso 1 1 calc R
H3B H 0.6220 0.4224 0.7625 0.028 Uiso 1 1 calc R
C4 C 0.3111(3) 0.39368(12) 0.79518(9) 0.0202(4) Uani 1 1 d .
C5 C 0.1998(2) 0.49215(12) 0.77376(10) 0.0221(4) Uani 1 1 d .
C6 C 0.1374(3) 0.54428(12) 0.84351(10) 0.0220(4) Uani 1 1 d .
C7 C 0.2210(3) 0.49855(12) 0.90462(10) 0.0225(4) Uani 1 1 d .
C8 C 0.2254(3) 0.53788(14) 0.98435(10) 0.0301(4) Uani 1 1 d .
H8A H 0.1395 0.4935 1.0176 0.036 Uiso 1 1 calc R
H8B H 0.1622 0.6062 0.9856 0.036 Uiso 1 1 calc R
C9 C 0.2201(3) 0.15879(12) 0.84664(10) 0.0288(4) Uani 1 1 d .
H9A H 0.2758 0.0896 0.8397 0.035 Uiso 1 1 calc R
H9B H 0.0722 0.1523 0.8646 0.035 Uiso 1 1 calc R
C10 C 0.3477(3) 0.20880(13) 0.91032(10) 0.0274(4) Uani 1 1 d .
H10A H 0.4969 0.2143 0.8936 0.033 Uiso 1 1 calc R
H10B H 0.3442 0.1646 0.9559 0.033 Uiso 1 1 calc R
C11 C 0.2691(3) 0.31391(12) 0.93332(9) 0.0249(4) Uani 1 1 d .
H11A H 0.3128 0.3263 0.9868 0.030 Uiso 1 1 calc R
H11B H 0.1125 0.3131 0.9323 0.030 Uiso 1 1 calc R
C12 C 0.3456(3) 0.40433(12) 0.88410(9) 0.0206(4) Uani 1 1 d .
C13 C 0.5763(3) 0.42289(13) 0.90939(10) 0.0227(4) Uani 1 1 d .
C14 C 0.6173(3) 0.51837(13) 0.95308(11) 0.0278(4) Uani 1 1 d .
H14A H 0.6212 0.5753 0.9165 0.033 Uiso 1 1 calc R
H14B H 0.7589 0.5136 0.9770 0.033 Uiso 1 1 calc R
C15 C 0.4554(3) 0.54268(15) 1.01527(10) 0.0295(4) Uani 1 1 d .
H15A H 0.4697 0.4908 1.0564 0.035 Uiso 1 1 calc R
C16 C 0.5005(4) 0.64513(19) 1.05029(15) 0.0612(7) Uani 1 1 d .
H16C H 0.6393 0.6439 1.0752 0.092 Uiso 1 1 calc R
H16B H 0.3912 0.6610 1.0882 0.092 Uiso 1 1 calc R
H16A H 0.5001 0.6966 1.0101 0.092 Uiso 1 1 calc R
C17 C 0.1432(3) 0.31225(12) 0.77324(10) 0.0219(4) Uani 1 1 d .
H17A H 0.0248 0.3168 0.8101 0.026 Uiso 1 1 calc R
H17B H 0.0859 0.3295 0.7222 0.026 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 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 N1 C1 110.94(13)
C17 N1 C9 113.72(13)
C1 N1 C9 116.69(14)
C6 O2 H2OA 109.5
N1 C1 C2 115.99(14)
N1 C1 H1A 108.3
C2 C1 H1A 108.3
N1 C1 H1B 108.3
C2 C1 H1B 108.3
H1A C1 H1B 107.4
C1 C2 C3 110.36(14)
C1 C2 H2A 109.6
C3 C2 H2A 109.6
C1 C2 H2B 109.6
C3 C2 H2B 109.6
H2A C2 H2B 108.1
C2 C3 C4 113.86(14)
C2 C3 H3A 108.8
C4 C3 H3A 108.8
C2 C3 H3B 108.8
C4 C3 H3B 108.8
H3A C3 H3B 107.7
C5 C4 C3 109.94(13)
C5 C4 C17 102.58(13)
C3 C4 C17 108.03(13)
C5 C4 C12 103.23(13)
C3 C4 C12 118.32(13)
C17 C4 C12 113.47(13)
O1 C5 C6 125.77(15)
O1 C5 C4 125.31(15)
C6 C5 C4 108.91(14)
C7 C6 O2 126.14(16)
C7 C6 C5 110.33(14)
O2 C6 C5 123.42(15)
C6 C7 C8 126.67(15)
C6 C7 C12 112.84(15)
C8 C7 C12 119.97(15)
C7 C8 C15 111.00(15)
C7 C8 H8A 109.4
C15 C8 H8A 109.4
C7 C8 H8B 109.4
C15 C8 H8B 109.4
H8A C8 H8B 108.0
N1 C9 C10 118.32(14)
N1 C9 H9A 107.7
C10 C9 H9A 107.7
N1 C9 H9B 107.7
C10 C9 H9B 107.7
H9A C9 H9B 107.1
C9 C10 C11 114.55(15)
C9 C10 H10A 108.6
C11 C10 H10A 108.6
C9 C10 H10B 108.6
C11 C10 H10B 108.6
H10A C10 H10B 107.6
C10 C11 C12 117.09(14)
C10 C11 H11A 108.0
C12 C11 H11A 108.0
C10 C11 H11B 108.0
C12 C11 H11B 108.0
H11A C11 H11B 107.3
C7 C12 C13 106.88(13)
C7 C12 C11 110.03(13)
C13 C12 C11 104.94(14)
C7 C12 C4 103.61(13)
C13 C12 C4 115.31(13)
C11 C12 C4 115.78(13)
O3 C13 C14 120.68(15)
O3 C13 C12 122.93(15)
C14 C13 C12 116.31(14)
C13 C14 C15 115.16(14)
C13 C14 H14A 108.5
C15 C14 H14A 108.5
C13 C14 H14B 108.5
C15 C14 H14B 108.5
H14A C14 H14B 107.5
C16 C15 C14 110.53(17)
C16 C15 C8 110.70(18)
C14 C15 C8 111.71(14)
C16 C15 H15A 107.9
C14 C15 H15A 107.9
C8 C15 H15A 107.9
C15 C16 H16C 109.5
C15 C16 H16B 109.5
H16C C16 H16B 109.5
C15 C16 H16A 109.5
H16C C16 H16A 109.5
H16B C16 H16A 109.5
N1 C17 C4 116.75(14)
N1 C17 H17A 108.1
C4 C17 H17A 108.1
N1 C17 H17B 108.1
C4 C17 H17B 108.1
H17A C17 H17B 107.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C17 1.460(2)
N1 C1 1.471(2)
N1 C9 1.471(2)
O1 C5 1.221(2)
O2 C6 1.3454(19)
O2 H2OA 0.8401
O3 C13 1.219(2)
C1 C2 1.519(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.528(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.539(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.529(2)
C4 C17 1.562(2)
C4 C12 1.577(2)
C5 C6 1.457(2)
C6 C7 1.338(2)
C7 C8 1.490(2)
C7 C12 1.519(2)
C8 C15 1.552(3)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.527(2)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.533(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.553(2)
C11 H11A 0.9900
C11 H11B 0.9900
C12 C13 1.544(2)
C13 C14 1.501(2)
C14 C15 1.528(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.517(3)
C15 H15A 1.0000
C16 H16C 0.9800
C16 H16B 0.9800
C16 H16A 0.9800
C17 H17A 0.9900
C17 H17B 0.9900
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
C17 N1 C1 C2 51.46(19)
C9 N1 C1 C2 -80.95(19)
N1 C1 C2 C3 -51.7(2)
C1 C2 C3 C4 51.46(19)
C2 C3 C4 C5 -161.34(14)
C2 C3 C4 C17 -50.13(18)
C2 C3 C4 C12 80.50(18)
C3 C4 C5 O1 43.4(2)
C17 C4 C5 O1 -71.3(2)
C12 C4 C5 O1 170.58(16)
C3 C4 C5 C6 -137.67(14)
C17 C4 C5 C6 107.61(14)
C12 C4 C5 C6 -10.53(16)
O1 C5 C6 C7 -172.39(17)
C4 C5 C6 C7 8.72(19)
O1 C5 C6 O2 4.0(3)
C4 C5 C6 O2 -174.87(14)
O2 C6 C7 C8 -7.4(3)
C5 C6 C7 C8 168.87(16)
O2 C6 C7 C12 -179.07(15)
C5 C6 C7 C12 -2.78(19)
C6 C7 C8 C15 -123.7(2)
C12 C7 C8 C15 47.4(2)
C17 N1 C9 C10 -55.5(2)
C1 N1 C9 C10 75.6(2)
N1 C9 C10 C11 62.6(2)
C9 C10 C11 C12 -83.3(2)
C6 C7 C12 C13 118.25(16)
C8 C7 C12 C13 -54.02(19)
C6 C7 C12 C11 -128.34(15)
C8 C7 C12 C11 59.4(2)
C6 C7 C12 C4 -3.97(18)
C8 C7 C12 C4 -176.24(15)
C10 C11 C12 C7 169.00(14)
C10 C11 C12 C13 -76.35(17)
C10 C11 C12 C4 52.0(2)
C5 C4 C12 C7 8.52(15)
C3 C4 C12 C7 130.16(14)
C17 C4 C12 C7 -101.72(15)
C5 C4 C12 C13 -107.90(15)
C3 C4 C12 C13 13.7(2)
C17 C4 C12 C13 141.86(14)
C5 C4 C12 C11 129.06(14)
C3 C4 C12 C11 -109.29(16)
C17 C4 C12 C11 18.82(19)
C7 C12 C13 O3 -177.05(16)
C11 C12 C13 O3 66.1(2)
C4 C12 C13 O3 -62.5(2)
C7 C12 C13 C14 6.0(2)
C11 C12 C13 C14 -110.82(16)
C4 C12 C13 C14 120.56(16)
O3 C13 C14 C15 -132.95(17)
C12 C13 C14 C15 44.1(2)
C13 C14 C15 C16 -174.60(18)
C13 C14 C15 C8 -50.9(2)
C7 C8 C15 C16 130.62(18)
C7 C8 C15 C14 7.0(2)
C1 N1 C17 C4 -51.68(19)
C9 N1 C17 C4 82.22(18)
C5 C4 C17 N1 167.29(14)
C3 C4 C17 N1 51.18(18)
C12 C4 C17 N1 -82.07(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652058
