#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2011736.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011736
loop_
_publ_author_name
'Ne\<cas, Marek'
'Dost\'al, Ji\<r\'i'
'Slav\'ik, Ji\<r\'i'
_publ_section_title
;
 (--)-Argemonine hemihydrate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              66
_journal_page_last               67
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C21 H25 N O4, 0.5H2 O'
_chemical_formula_moiety         'C21 H25 N O4, 0.5H2 O'
_chemical_formula_sum            'C21 H26 N O4.5'
_chemical_formula_weight         364.43
_chemical_name_common            '(-)-Argemonine hemihydrate'
_chemical_name_systematic
;
(6S,12S)-2,3,8,9-tetramethoxy-13-methyl-13-
azadibenzo[b,f]bicyclo[3.3.1]nona-2,6-diene hemihydrate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 126.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.169(4)
_cell_length_b                   9.801(2)
_cell_length_c                   12.726(3)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      20.84
_cell_measurement_theta_min      11.01
_cell_volume                     1810.8(10)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma, 1992)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'ORTEPIII (Johnson & Burnett, 1996)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full .995
_diffrn_measured_fraction_theta_max .929
_diffrn_measurement_device_type  'Kuma KM-4 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .021
_diffrn_reflns_av_sigmaI/netI    .0149
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6415
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         3.95
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'trigonal bipyramid'
_exptl_crystal_F_000             780
_exptl_crystal_size_max          .70
_exptl_crystal_size_mid          .50
_exptl_crystal_size_min          .50
_refine_diff_density_max         .229
_refine_diff_density_min         -.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          .028
_refine_ls_R_factor_gt           .028
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.4286P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .077
_reflns_number_gt                2201
_reflns_number_total             2254
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    sx1108.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2'
_[local]_cod_chemical_formula_sum_orig 'C21 H26 N1 O4.5'
_cod_original_cell_volume        1810.8(7)
_cod_database_code               2011736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O18 .20462(7) -.02808(11) .71574(10) .0185(2) Uani d . 1 O
O19 .11674(7) .16177(13) .54123(11) .0231(2) Uani d . 1 O
O20 .59998(8) .67489(12) .89583(11) .0222(2) Uani d . 1 O
O21 .64642(8) .55233(12) 1.11413(11) .0241(2) Uani d . 1 O
N1 .50822(8) .09674(14) .66303(12) .0167(2) Uani d . 1 N
C1 .34395(9) .00897(14) .73301(13) .0147(3) Uani d . 1 C
H1 .3760 -.0616 .7963 .018 Uiso calc R 1 H
C2 .25372(9) .03771(15) .68216(13) .0153(3) Uani d . 1 C
C3 .20607(9) .14204(15) .58740(13) .0170(3) Uani d . 1 C
C4 .25100(9) .21543(16) .54884(13) .0172(3) Uani d . 1 C
H4 .2192 .2864 .4859 .021 Uiso calc R 1 H
C4A .34288(10) .18693(14) .60110(13) .0159(3) Uani d . 1 C
C5 .38981(10) .26917(16) .55722(13) .0179(3) Uani d . 1 C
H5A .3774 .3674 .5580 .021 Uiso calc R 1 H
H5B .3645 .2437 .4660 .021 Uiso calc R 1 H
C6 .49433(10) .24432(14) .64784(13) .0157(3) Uani d . 1 C
H6 .5207 .2798 .6032 .019 Uiso calc R 1 H
C6A .53892(9) .32075(15) .77685(13) .0151(3) Uani d . 1 C
C7 .55162(10) .46154(15) .77932(14) .0168(3) Uani d . 1 C
H7 .5348 .5069 .7018 .020 Uiso calc R 1 H
C8 .58810(10) .53527(15) .89255(15) .0177(3) Uani d . 1 C
C9 .61269(9) .46963(16) 1.00783(14) .0176(3) Uani d . 1 C
C10 .60070(9) .33018(15) 1.00613(14) .0165(3) Uani d . 1 C
H10 .6173 .2850 1.0836 .020 Uiso calc R 1 H
C10A .56435(9) .25494(14) .89111(13) .0142(3) Uani d . 1 C
C11 .55449(9) .10271(15) .89139(13) .0152(3) Uani d . 1 C
H11A .5317 .0791 .9428 .018 Uiso calc R 1 H
H11B .6156 .0594 .9345 .018 Uiso calc R 1 H
C12 .48756(9) .04657(15) .75113(13) .0148(3) Uani d . 1 C
H12 .4931 -.0551 .7553 .018 Uiso calc R 1 H
C12A .38865(9) .08291(14) .69218(12) .0144(3) Uani d . 1 C
C13 .25171(10) -.13501(17) .80910(15) .0209(3) Uani d . 1 C
H13A .2687 -.2061 .7731 .031 Uiso calc R 1 H
H13B .2114 -.1741 .8285 .031 Uiso calc R 1 H
H13C .3075 -.0987 .8901 .031 Uiso calc R 1 H
C14 .06546(10) .25843(18) .43721(15) .0254(3) Uani d . 1 C
H14A .0920 .3495 .4696 .038 Uiso calc R 1 H
H14B .0012 .2586 .4058 .038 Uiso calc R 1 H
H14C .0680 .2335 .3648 .038 Uiso calc R 1 H
C15 .67676(11) .71114(17) .89810(16) .0238(3) Uani d . 1 C
H15A .7327 .6694 .9748 .036 Uiso calc R 1 H
H15B .6837 .8106 .9034 .036 Uiso calc R 1 H
H15C .6668 .6784 .8176 .036 Uiso calc R 1 H
C16 .66980(13) .4889(2) 1.23151(16) .0303(4) Uani d . 1 C
H16A .6149 .4459 1.2145 .045 Uiso calc R 1 H
H16B .6934 .5579 1.3006 .045 Uiso calc R 1 H
H16C .7172 .4195 1.2601 .045 Uiso calc R 1 H
C17 .59854(10) .05447(16) .70245(16) .0212(3) Uani d . 1 C
H17A .6058 .0826 .6352 .032 Uiso calc R 1 H
H17B .6040 -.0450 .7121 .032 Uiso calc R 1 H
H17C .6466 .0974 .7865 .032 Uiso calc R 1 H
O30 .5000 .8061(2) 1.0000 .0331(4) Uani d S 1 O
H30A .533(2) .757(4) .983(3) .084(11) Uiso d . 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O18 .0174(4) .0170(5) .0222(5) .0010(4) .0125(4) .0032(4)
O19 .0159(5) .0238(6) .0248(5) .0053(4) .0097(4) .0063(5)
O20 .0298(5) .0109(5) .0297(5) -.0011(4) .0199(5) -.0013(4)
O21 .0338(6) .0171(5) .0199(5) -.0059(5) .0154(5) -.0045(4)
N1 .0209(5) .0130(5) .0202(5) .0004(5) .0144(5) .0003(4)
C1 .0157(6) .0127(6) .0135(5) .0007(5) .0075(5) .0005(5)
C2 .0171(6) .0134(6) .0153(6) -.0020(5) .0096(5) -.0021(5)
C3 .0154(6) .0156(6) .0158(6) .0016(5) .0073(5) -.0009(5)
C4 .0183(6) .0143(6) .0144(6) .0022(5) .0074(5) .0014(5)
C4A .0186(6) .0140(6) .0136(5) -.0004(5) .0089(5) -.0001(5)
C5 .0225(6) .0155(6) .0159(6) .0012(5) .0117(5) .0026(5)
C6 .0219(6) .0124(6) .0169(6) -.0010(5) .0138(5) .0004(5)
C6A .0167(6) .0131(6) .0179(6) .0000(5) .0116(5) .0001(5)
C7 .0207(6) .0137(6) .0192(6) .0005(5) .0136(6) .0019(5)
C8 .0204(6) .0121(6) .0227(7) -.0007(5) .0141(6) -.0002(5)
C9 .0177(6) .0163(7) .0182(6) -.0021(5) .0105(5) -.0023(5)
C10 .0167(6) .0164(7) .0158(6) -.0007(5) .0094(5) .0011(5)
C10A .0143(5) .0111(6) .0174(6) -.0006(5) .0096(5) .0000(5)
C11 .0159(6) .0127(6) .0159(6) .0003(5) .0090(5) .0028(5)
C12 .0174(6) .0111(6) .0175(6) .0005(5) .0114(5) .0013(5)
C12A .0167(6) .0123(6) .0132(6) -.0012(5) .0084(5) -.0010(5)
C13 .0184(6) .0191(7) .0228(7) -.0020(6) .0111(6) .0052(6)
C14 .0199(6) .0223(7) .0243(7) .0065(6) .0080(6) .0046(6)
C15 .0276(7) .0150(6) .0293(7) -.0045(6) .0173(6) -.0005(6)
C16 .0430(9) .0274(8) .0202(7) -.0090(8) .0188(7) -.0056(7)
C17 .0237(7) .0185(7) .0289(7) .0007(6) .0198(6) .0012(6)
O30 .0294(9) .0193(8) .0492(11) .000 .0228(9) .000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_site_symmetry_3
_geom_angle
C2 O18 C13 . 115.67(11)
C3 O19 C14 . 115.91(12)
C8 O20 C15 . 112.41(12)
C9 O21 C16 . 116.90(13)
C17 N1 C6 . 113.32(12)
C17 N1 C12 . 113.24(12)
C6 N1 C12 . 109.29(11)
C2 C1 C12A . 120.66(12)
C2 C1 H1 . 119.7
C12A C1 H1 . 119.7
O18 C2 C1 . 124.98(12)
O18 C2 C3 . 115.47(12)
C1 C2 C3 . 119.54(12)
O19 C3 C4 . 125.18(13)
O19 C3 C2 . 115.42(13)
C4 C3 C2 . 119.40(13)
C3 C4 C4A . 121.10(13)
C3 C4 H4 . 119.5
C4A C4 H4 . 119.5
C12A C4A C4 . 119.20(13)
C12A C4A C5 . 121.10(12)
C4 C4A C5 . 119.70(13)
C4A C5 C6 . 110.93(11)
C4A C5 H5A . 109.5
C6 C5 H5A . 109.5
C4A C5 H5B . 109.5
C6 C5 H5B . 109.5
H5A C5 H5B . 108.0
N1 C6 C6A . 114.03(12)
N1 C6 C5 . 107.05(11)
C6A C6 C5 . 110.35(12)
N1 C6 H6 . 108.4
C6A C6 H6 . 108.4
C5 C6 H6 . 108.4
C10A C6A C7 . 119.21(13)
C10A C6A C6 . 121.77(13)
C7 C6A C6 . 118.98(12)
C8 C7 C6A . 120.81(13)
C8 C7 H7 . 119.6
C6A C7 H7 . 119.6
C7 C8 O20 . 121.35(13)
C7 C8 C9 . 120.24(14)
O20 C8 C9 . 118.40(13)
O21 C9 C10 . 125.10(13)
O21 C9 C8 . 115.70(13)
C10 C9 C8 . 119.20(14)
C9 C10 C10A . 120.54(13)
C9 C10 H10 . 119.7
C10A C10 H10 . 119.7
C6A C10A C10 . 119.99(13)
C6A C10A C11 . 119.83(13)
C10 C10A C11 . 120.17(12)
C10A C11 C12 . 111.42(11)
C10A C11 H11A . 109.3
C12 C11 H11A . 109.3
C10A C11 H11B . 109.3
C12 C11 H11B . 109.3
H11A C11 H11B . 108.0
N1 C12 C12A . 108.39(11)
N1 C12 C11 . 112.41(11)
C12A C12 C11 . 111.45(11)
N1 C12 H12 . 108.2
C12A C12 H12 . 108.2
C11 C12 H12 . 108.2
C4A C12A C1 . 120.09(12)
C4A C12A C12 . 121.61(12)
C1 C12A C12 . 118.30(12)
O18 C13 H13A . 109.5
O18 C13 H13B . 109.5
H13A C13 H13B . 109.5
O18 C13 H13C . 109.5
H13A C13 H13C . 109.5
H13B C13 H13C . 109.5
O19 C14 H14A . 109.5
O19 C14 H14B . 109.5
H14A C14 H14B . 109.5
O19 C14 H14C . 109.5
H14A C14 H14C . 109.5
H14B C14 H14C . 109.5
O20 C15 H15A . 109.5
O20 C15 H15B . 109.5
H15A C15 H15B . 109.5
O20 C15 H15C . 109.5
H15A C15 H15C . 109.5
H15B C15 H15C . 109.5
O21 C16 H16A . 109.5
O21 C16 H16B . 109.5
H16A C16 H16B . 109.5
O21 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
N1 C17 H17A . 109.5
N1 C17 H17B . 109.5
H17A C17 H17B . 109.5
N1 C17 H17C . 109.5
H17A C17 H17C . 109.5
H17B C17 H17C . 109.5
H30A O30 H30A 2_657 115(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O18 C2 1.3611(16)
O18 C13 1.4211(18)
O19 C3 1.3675(17)
O19 C14 1.4264(19)
O20 C8 1.3820(18)
O20 C15 1.4230(19)
O21 C9 1.3659(18)
O21 C16 1.426(2)
N1 C6 1.4610(18)
N1 C12 1.4648(17)
N1 C17 1.4582(18)
C1 C2 1.3821(19)
C1 C12A 1.4008(19)
C1 H1 .9500
C2 C3 1.4120(19)
C3 C4 1.381(2)
C4 C4A 1.404(2)
C4 H4 .9500
C4A C12A 1.3839(19)
C4A C5 1.5037(19)
C5 C6 1.537(2)
C5 H5A .9900
C5 H5B .9900
C6 C6A 1.5209(19)
C6 H6 1.0000
C6A C10A 1.3914(19)
C6A C7 1.3963(19)
C7 C8 1.375(2)
C7 H7 .9500
C8 C9 1.406(2)
C9 C10 1.382(2)
C10 C10A 1.4000(19)
C10 H10 .9500
C10A C11 1.5029(19)
C11 C12 1.535(2)
C11 H11A .9900
C11 H11B .9900
C12 C12A 1.5159(18)
C12 H12 1.0000
C13 H13A .9800
C13 H13B .9800
C13 H13C .9800
C14 H14A .9800
C14 H14B .9800
C14 H14C .9800
C15 H15A .9800
C15 H15B .9800
C15 H15C .9800
C16 H16A .9800
C16 H16B .9800
C16 H16C .9800
C17 H17A .9800
C17 H17B .9800
C17 H17C .9800
O30 H30A .90(4)
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_publ_flag
O30 H30A O20 .90(4) 2.23(3) 3.0997(15) 164(3) yes
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
C13 O18 C2 C1 -.9(2)
C13 O18 C2 C3 178.77(12)
C12A C1 C2 O18 -179.88(13)
C12A C1 C2 C3 .5(2)
C14 O19 C3 C4 5.6(2)
C14 O19 C3 C2 -174.66(13)
O18 C2 C3 O19 -.67(18)
C1 C2 C3 O19 179.02(12)
O18 C2 C3 C4 179.12(12)
C1 C2 C3 C4 -1.2(2)
O19 C3 C4 C4A -179.45(13)
C2 C3 C4 C4A .8(2)
C3 C4 C4A C12A .4(2)
C3 C4 C4A C5 -179.81(13)
C12A C4A C5 C6 -13.16(18)
C4 C4A C5 C6 167.03(12)
C17 N1 C6 C6A -79.59(15)
C12 N1 C6 C6A 47.71(15)
C17 N1 C6 C5 158.06(11)
C12 N1 C6 C5 -74.64(14)
C4A C5 C6 N1 48.37(15)
C4A C5 C6 C6A -76.25(15)
N1 C6 C6A C10A -19.05(19)
C5 C6 C6A C10A 101.48(15)
N1 C6 C6A C7 163.25(12)
C5 C6 C6A C7 -76.23(16)
C10A C6A C7 C8 -.5(2)
C6 C6A C7 C8 177.27(12)
C6A C7 C8 O20 -179.21(13)
C6A C7 C8 C9 -.4(2)
C15 O20 C8 C7 -75.56(18)
C15 O20 C8 C9 105.63(15)
C16 O21 C9 C10 -.8(2)
C16 O21 C9 C8 178.50(14)
C7 C8 C9 O21 -178.61(12)
O20 C8 C9 O21 .2(2)
C7 C8 C9 C10 .7(2)
O20 C8 C9 C10 179.56(13)
O21 C9 C10 C10A 179.15(13)
C8 C9 C10 C10A -.1(2)
C7 C6A C10A C10 1.1(2)
C6 C6A C10A C10 -176.60(12)
C7 C6A C10A C11 -177.65(13)
C6 C6A C10A C11 4.7(2)
C9 C10 C10A C6A -.8(2)
C9 C10 C10A C11 177.96(13)
C6A C10A C11 C12 -18.97(17)
C10 C10A C11 C12 162.29(12)
C17 N1 C12 C12A -173.65(12)
C6 N1 C12 C12A 59.01(14)
C17 N1 C12 C11 62.72(16)
C6 N1 C12 C11 -64.63(15)
C10A C11 C12 N1 49.41(15)
C10A C11 C12 C12A -72.50(14)
C4 C4A C12A C1 -1.11(19)
C5 C4A C12A C1 179.07(12)
C4 C4A C12A C12 179.45(12)
C5 C4A C12A C12 -.4(2)
C2 C1 C12A C4A .7(2)
C2 C1 C12A C12 -179.85(12)
N1 C12 C12A C4A -21.45(18)
C11 C12 C12A C4A 102.76(14)
N1 C12 C12A C1 159.10(12)
C11 C12 C12A C1 -76.69(16)