#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011736.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
'Nečas, Marek'
'Dostál, Jiří'
'Slavík, Jiří'
_publ_section_title
;
 (--)-Argemonine hemihydrate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              66
_journal_page_last               67
_journal_paper_doi               10.1107/S010827010001252X
_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       ω
_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/[σ²(Fo²)+(0.0540P)²+0.4286P] where P = (Fo²+2Fc²)/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)
_cod_data_source_file            sx1108.cif
_cod_data_source_block           I
_cod_original_cell_volume        1810.8(7)
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C21 H26 N1 O4.5'
_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_disorder_assembly
_atom_site_disorder_group
_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_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
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)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182217
