#------------------------------------------------------------------------------
#$Date: 2017-09-12 13:05:52 +0100 (Tue, 12 Sep 2017) $
#$Revision: 200786 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/31/2003181.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_2003181
loop_
_publ_author_name
'Luger, Peter'
'Weber, Manuela'
'Dung, Nguyen Xuan'
'Ky, Pham Thanh'
'Long, Phan Ke'
_publ_section_title
;
 Securinine, an Alkaloid from Fluggea virosa
;
_journal_coden_ASTM              ACSCEE
_journal_issue                   1
_journal_name_full
;
 Acta Crystallographica, Section C: Crystal Structure Communications
;
_journal_page_first              127
_journal_page_last               129
_journal_paper_doi               10.1107/S0108270194007857
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C13 H15 N1 O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.27
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00(2)
_cell_angle_beta                 90.00(2)
_cell_angle_gamma                90.00(2)
_cell_formula_units_Z            4
_cell_length_a                   16.492(4)
_cell_length_b                   9.483(3)
_cell_length_c                   7.025(2)
_cell_measurement_reflns_used    86
_cell_measurement_temperature    293
_cell_measurement_theta_max      40
_cell_measurement_theta_min      20
_cell_volume                     1098.7(5)
_diffrn_measurement_device       'STOE four-circle MicroVAX-controlled'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1081
_diffrn_reflns_theta_max         63.99
_diffrn_standards_decay_%        statistical
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         .259
_refine_diff_density_min         -.264
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   0
_refine_ls_extinction_coef       925(42)
_refine_ls_extinction_method     Zachariasen
_refine_ls_goodness_of_fit_all   1.604
_refine_ls_goodness_of_fit_obs   1.717
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     206
_refine_ls_number_reflns         816
_refine_ls_R_factor_obs          .036
_refine_ls_shift/esd_max         0.722
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .029
_refine_ls_wR_factor_obs         .026
_reflns_number_observed          816
_reflns_number_total             1081
_reflns_observed_criterion       F~o~>2\s(F~o~)
_cod_original_formula_sum        'C13 H15 N1 O2'
_cod_database_code               2003181
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+y,1/2-z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_22
_atom_site_aniso_U_23
_atom_site_aniso_U_33
O1 .049(2) -.005(2) -.013(2) .047(2) .010(2) .041(1)
C2 .043(3) .004(3) -.002(2) .059(3) -.007(3) .044(2)
O2 .062(2) -.005(2) -.022(2) .090(3) .010(2) .050(2)
C3 .034(2) -.002(2) -.004(2) .045(3) -.004(3) .052(3)
C4 .037(2) .005(2) .003(2) .036(2) -.001(3) .043(2)
C5 .035(2) .003(2) .011(3) .055(3) .017(3) .056(3)
C6 .044(3) .013(3) .013(2) .070(4) .014(3) .040(3)
C7 .047(3) .003(3) -.003(2) .063(3) -.005(3) .034(2)
N7 .033(2) .002(2) -.005(2) .055(2) .003(2) .033(2)
C8 .040(3) .003(3) -.006(2) .061(3) .010(3) .052(3)
C9 .036(3) -.001(3) -.004(3) .076(4) .016(3) .069(3)
C10 .039(3) -.003(3) .017(3) .075(4) .008(3) .059(3)
C11 .049(3) -.011(3) .003(2) .054(3) .007(3) .043(3)
C12 .037(2) -.000(2) .000(2) .033(3) -.001(2) .034(2)
C13 .043(2) .003(2) -.005(2) .036(2) .002(2) .031(2)
C14 .044(3) .004(3) -.005(2) .048(3) -.009(3) .049(2)
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O1 1.00000 .3985(2) .2371(3) .2235(4) .046(2)
C2 1.00000 .3345(3) .1609(5) .1494(6) .049(3)
O2 1.00000 .3017(2) .2008(4) .0058(4) .067(2)
C3 1.00000 .3192(2) .0400(5) .2710(6) .044(3)
H3 1.00000 .271(2) -.036(4) .260(5) .06(1)
C4 1.00000 .3701(2) .0462(4) .4183(6) .039(2)
C5 1.00000 .3813(2) -.0346(5) .5921(7) .049(3)
H5 1.00000 .350(2) -.134(4) .609(7) .08(1)
C6 1.00000 .4274(3) .0222(6) .7284(6) .051(3)
H6 1.00000 .439(2) -.026(5) .847(6) .07(2)
C7 1.00000 .4682(3) .1633(5) .7039(6) .048(3)
H7 1.00000 .484(2) .202(4) .825(5) .04(1)
N7 1.00000 .5418(2) .1597(4) .5867(5) .041(2)
C8 1.00000 .6156(3) .0866(6) .6401(7) .051(3)
H81 1.00000 .631(2) .124(4) .781(6) .07(1)
H82 1.00000 .611(2) -.014(4) .624(5) .04(1)
C9 1.00000 .6822(3) .1389(7) .5077(8) .060(3)
H91 1.00000 .695(3) .243(4) .541(6) .09(2)
H92 1.00000 .733(3) .087(5) .539(7) .09(2)
C10 1.00000 .6582(3) .1219(7) .2989(7) .057(3)
H101 1.00000 .704(2) .159(4) .217(6) .07(1)
H102 1.00000 .656(3) .016(5) .264(6) .08(2)
C11 1.00000 .5745(3) .1846(6) .2549(7) .049(3)
H111 1.00000 .572(2) .281(4) .265(5) .03(1)
H112 1.00000 .552(3) .150(4) .120(6) .08(1)
C12 1.00000 .5148(2) .1231(4) .3948(6) .035(2)
H12 1.00000 .517(2) .021(3) .374(4) .018(9)
C13 1.00000 .4254(2) .1701(4) .3964(6) .037(2)
C14 1.00000 .4162(3) .2583(5) .5768(7) .047(3)
H141 1.00000 .352(2) .267(4) .617(6) .06(1)
H142 1.00000 .439(2) .356(4) .569(5) .05(1)