#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225247.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_2225247
loop_
_publ_author_name
'von Langermann, Jan'
'Lorenz, Heike'
'Boehm, Oliver'
'Flemming, Anke'
'Bernsdorf, Arne'
'Köckerling, Martin'
'Schinzer, Dieter'
'Seidel-Morgenstern, Andreas'
_publ_section_title
;(3R*,5'S*)-6,7-Dimethoxy-3-(4'-methoxy-6'-methyl-5',6',7',8'-tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5'-yl)isobenzofuran-1(3H)-one
 (racemic α-noscapine)
;
_journal_coeditor_code           HB5290
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o570
_journal_paper_doi               10.1107/S1600536810003958
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H23 N O7'
_chemical_formula_moiety         'C22 H23 N O7'
_chemical_formula_sum            'C22 H23 N O7'
_chemical_formula_weight         413.41
_chemical_melting_point          501.9
_chemical_name_common            α-noscapine
_chemical_name_systematic
;
(3R*,5'S*)-6,7-Dimethoxy-3-(4'-methoxy-6'-methyl-5',6',7',8'-
tetrahydro-1,3-dioxolo[4,5-g]isoquinolin-5'-yl)isobenzofuran-
1(3H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 95.781(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5242(8)
_cell_length_b                   9.3581(5)
_cell_length_c                   13.2801(7)
_cell_measurement_reflns_used    6930
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.93
_cell_measurement_theta_min      2.52
_cell_volume                     1919.48(17)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14003
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.708
_refine_ls_extinction_coef       0.0057(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         3864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0570
_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)+(0.0785P)²+1.3900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2989
_reflns_number_total             3864
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5290.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225247
_cod_database_fobs_code          2225247
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
N N1 0.73446(12) 0.3640(2) 0.27455(14) 0.0344(5) Uani d . 1 . .
O O1 1.04337(10) 0.66824(18) 0.09956(12) 0.0386(4) Uani d . 1 . .
O O2 0.95148(11) 0.68699(18) -0.04776(12) 0.0404(4) Uani d . 1 . .
O O3 0.98826(10) 0.53115(19) 0.28872(11) 0.0374(4) Uani d . 1 . .
O O4 0.79757(10) 0.49937(17) 0.46248(11) 0.0342(4) Uani d . 1 . .
O O5 0.69655(18) 0.5011(2) 0.56862(18) 0.0843(9) Uani d . 1 . .
C C1 1.03115(17) 0.7361(3) 0.00278(19) 0.0428(6) Uani d . 1 . .
H H1A 1.0296 0.8412 0.0111 0.051 Uiso calc R 1 . .
H H1B 1.0796 0.7120 -0.0373 0.051 Uiso calc R 1 . .
C C2 0.90820(15) 0.6242(2) 0.02642(16) 0.0324(5) Uani d . 1 . .
C C3 0.96312(14) 0.6128(2) 0.11444(17) 0.0305(5) Uani d . 1 . .
C C4 0.93703(14) 0.5473(2) 0.19924(16) 0.0287(5) Uani d . 1 . .
C C5 0.85049(13) 0.4988(2) 0.19361(15) 0.0284(5) Uani d . 1 . .
C C6 0.81858(13) 0.4371(2) 0.28879(16) 0.0293(5) Uani d . 1 . .
H H6A 0.8627 0.3669 0.3183 0.035 Uiso calc R 1 . .
C C7 0.70645(16) 0.3236(3) 0.16978(19) 0.0412(6) Uani d . 1 . .
H H7A 0.6475 0.2824 0.1660 0.049 Uiso calc R 1 . .
H H7B 0.7459 0.2496 0.1473 0.049 Uiso calc R 1 . .
C C8 0.70633(15) 0.4513(3) 0.10059(18) 0.0412(6) Uani d . 1 . .
H H8A 0.6858 0.4225 0.0305 0.049 Uiso calc R 1 . .
H H8B 0.6664 0.5251 0.1224 0.049 Uiso calc R 1 . .
C C9 0.79610(14) 0.5116(2) 0.10352(16) 0.0323(5) Uani d . 1 . .
C C10 0.82522(14) 0.5736(2) 0.01770(16) 0.0343(5) Uani d . 1 . .
H H10A 0.7889 0.5805 -0.0441 0.041 Uiso calc R 1 . .
C C11A 1.07435(17) 0.4888(4) 0.2848(2) 0.0634(9) Uani d . 1 . .
H H11A 1.1034 0.4824 0.3537 0.095 Uiso calc R 1 . .
H H11B 1.1042 0.5592 0.2461 0.095 Uiso calc R 1 . .
H H11C 1.0757 0.3953 0.2518 0.095 Uiso calc R 1 . .
C C13 0.81365(13) 0.5602(2) 0.36560(15) 0.0279(5) Uani d . 1 A .
H H13A 0.8699 0.6132 0.3730 0.033 Uiso calc R 1 . .
C C14 0.72208(18) 0.5464(3) 0.4926(2) 0.0451(6) Uani d . 1 . .
C C15 0.68646(15) 0.6537(2) 0.41869(19) 0.0379(6) Uani d . 1 A .
C C16 0.61460(19) 0.7398(3) 0.4222(3) 0.0668(10) Uani d . 1 . .
C C17 0.59567(16) 0.8363(3) 0.3418(2) 0.0511(7) Uani d . 1 A .
C C18 0.64984(15) 0.8462(2) 0.26480(17) 0.0358(5) Uani d . 1 . .
H H18A 0.6367 0.9123 0.2111 0.043 Uiso calc R 1 A .
C C19 0.72308(15) 0.7602(2) 0.26562(16) 0.0348(5) Uani d . 1 A .
H H19A 0.7604 0.7682 0.2134 0.042 Uiso calc R 1 . .
C C20 0.74082(13) 0.6636(2) 0.34276(15) 0.0266(5) Uani d . 1 . .
C C12 0.73227(19) 0.2382(3) 0.3401(2) 0.0483(7) Uani d . 1 . .
H H12A 0.6754 0.1924 0.3286 0.073 Uiso calc R 1 . .
H H12B 0.7428 0.2677 0.4110 0.073 Uiso calc R 1 . .
H H12C 0.7772 0.1705 0.3244 0.073 Uiso calc R 1 . .
O O6A 0.57726(16) 0.7471(3) 0.51826(17) 0.0462(9) Uani d P 0.688(5) A 1
C C22A 0.4909(3) 0.7090(9) 0.5089(4) 0.0661(17) Uani d P 0.688(5) A 1
H H22A 0.4731 0.6860 0.5758 0.099 Uiso calc PR 0.688(5) A 1
H H22B 0.4822 0.6252 0.4647 0.099 Uiso calc PR 0.688(5) A 1
H H22C 0.4559 0.7886 0.4795 0.099 Uiso calc PR 0.688(5) A 1
O O6B 0.5332(3) 0.6839(5) 0.4441(4) 0.0319(17) Uani d P 0.312(5) A 2
C C22B 0.5107(6) 0.7879(10) 0.5178(7) 0.033(2) Uani d P 0.312(5) A 2
H H22D 0.4482 0.8054 0.5088 0.050 Uiso calc PR 0.312(5) A 2
H H22E 0.5417 0.8774 0.5083 0.050 Uiso calc PR 0.312(5) A 2
H H22F 0.5271 0.7513 0.5862 0.050 Uiso calc PR 0.312(5) A 2
C C21A 0.4969(5) 1.0087(11) 0.2733(6) 0.0490(17) Uani d P 0.672(15) A 3
H H21A 0.4501 1.0716 0.2903 0.074 Uiso calc PR 0.672(15) A 3
H H21B 0.4749 0.9430 0.2193 0.074 Uiso calc PR 0.672(15) A 3
H H21C 0.5439 1.0664 0.2504 0.074 Uiso calc PR 0.672(15) A 3
O O7A 0.5288(3) 0.9287(5) 0.3606(5) 0.0431(15) Uani d P 0.672(15) A 3
C C21B 0.4989(11) 1.0049(18) 0.2305(13) 0.050(4) Uani d P 0.328(15) A 4
H H21D 0.4368 1.0183 0.2108 0.075 Uiso calc PR 0.328(15) A 4
H H21E 0.5278 0.9793 0.1708 0.075 Uiso calc PR 0.328(15) A 4
H H21F 0.5237 1.0937 0.2597 0.075 Uiso calc PR 0.328(15) A 4
O O7B 0.5109(4) 0.8924(8) 0.3042(11) 0.039(3) Uani d P 0.328(15) A 4
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 N1 C12 . . 109.51(19)
C7 N1 C6 . . 114.66(17)
C12 N1 C6 . . 111.77(19)
C3 O1 C1 . . 104.81(18)
C2 O2 C1 . . 105.30(18)
C4 O3 C11A . . 118.17(18)
C14 O4 C13 . . 111.50(17)
O2 C1 O1 . . 108.11(18)
O2 C1 H1A . . 110.1
O1 C1 H1A . . 110.1
O2 C1 H1B . . 110.1
O1 C1 H1B . . 110.1
H1A C1 H1B . . 108.4
C10 C2 O2 . . 127.6(2)
C10 C2 C3 . . 122.8(2)
O2 C2 C3 . . 109.5(2)
C4 C3 C2 . . 121.3(2)
C4 C3 O1 . . 128.8(2)
C2 C3 O1 . . 109.82(19)
O3 C4 C3 . . 124.4(2)
O3 C4 C5 . . 118.44(19)
C3 C4 C5 . . 117.1(2)
C9 C5 C4 . . 120.45(19)
C9 C5 C6 . . 121.71(19)
C4 C5 C6 . . 117.82(19)
N1 C6 C5 . . 115.49(18)
N1 C6 C13 . . 109.24(16)
C5 C6 C13 . . 107.95(17)
N1 C6 H6A . . 108.0
C5 C6 H6A . . 108.0
C13 C6 H6A . . 108.0
N1 C7 C8 . . 110.9(2)
N1 C7 H7A . . 109.5
C8 C7 H7A . . 109.5
N1 C7 H7B . . 109.5
C8 C7 H7B . . 109.5
H7A C7 H7B . . 108.1
C9 C8 C7 . . 109.8(2)
C9 C8 H8A . . 109.7
C7 C8 H8A . . 109.7
C9 C8 H8B . . 109.7
C7 C8 H8B . . 109.7
H8A C8 H8B . . 108.2
C10 C9 C5 . . 121.2(2)
C10 C9 C8 . . 120.8(2)
C5 C9 C8 . . 118.0(2)
C2 C10 C9 . . 117.1(2)
C2 C10 H10A . . 121.5
C9 C10 H10A . . 121.5
O3 C11A H11A . . 109.5
O3 C11A H11B . . 109.5
H11A C11A H11B . . 109.5
O3 C11A H11C . . 109.5
H11A C11A H11C . . 109.5
H11B C11A H11C . . 109.5
O4 C13 C20 . . 103.85(15)
O4 C13 C6 . . 108.49(17)
C20 C13 C6 . . 115.78(17)
O4 C13 H13A . . 109.5
C20 C13 H13A . . 109.5
C6 C13 H13A . . 109.5
O5 C14 O4 . . 120.3(2)
O5 C14 C15 . . 132.0(2)
O4 C14 C15 . . 107.71(19)
C16 C15 C20 . . 122.7(2)
C16 C15 C14 . . 128.8(2)
C20 C15 C14 . . 108.4(2)
C15 C16 C17 . . 117.2(2)
C15 C16 O6B . . 121.9(3)
C17 C16 O6B . . 105.6(3)
C15 C16 O6A . . 116.8(3)
C17 C16 O6A . . 124.3(2)
C18 C17 O7A . . 127.4(3)
C18 C17 C16 . . 120.3(2)
O7A C17 C16 . . 111.4(3)
C18 C17 O7B . . 108.4(5)
C16 C17 O7B . . 127.2(4)
C17 C18 C19 . . 120.6(2)
C17 C18 H18A . . 119.7
C19 C18 H18A . . 119.7
C20 C19 C18 . . 119.3(2)
C20 C19 H19A . . 120.4
C18 C19 H19A . . 120.4
C19 C20 C15 . . 119.8(2)
C19 C20 C13 . . 131.89(18)
C15 C20 C13 . . 108.27(19)
N1 C12 H12A . . 109.5
N1 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
N1 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C22A O6A C16 . . 112.2(3)
O6A C22A H22A . . 109.5
O6A C22A H22B . . 109.5
H22A C22A H22B . . 109.5
O6A C22A H22C . . 109.5
H22A C22A H22C . . 109.5
H22B C22A H22C . . 109.5
C16 O6B C22B . . 99.8(5)
O6B C22B H22D . . 109.5
O6B C22B H22E . . 109.5
H22D C22B H22E . . 109.5
O6B C22B H22F . . 109.5
H22D C22B H22F . . 109.5
H22E C22B H22F . . 109.5
O7A C21A H21A . . 109.5
O7A C21A H21B . . 109.5
H21A C21A H21B . . 109.5
O7A C21A H21C . . 109.5
H21A C21A H21C . . 109.5
H21B C21A H21C . . 109.5
C17 O7A C21A . . 112.6(4)
O7B C21B H21D . . 109.5
O7B C21B H21E . . 109.5
H21D C21B H21E . . 109.5
O7B C21B H21F . . 109.5
H21D C21B H21F . . 109.5
H21E C21B H21F . . 109.5
C21B O7B C17 . . 123.3(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C7 . 1.465(3)
N1 C12 . 1.466(3)
N1 C6 . 1.469(3)
O1 C3 . 1.382(3)
O1 C1 . 1.429(3)
O2 C2 . 1.379(3)
O2 C1 . 1.423(3)
O3 C4 . 1.370(3)
O3 C11A . 1.400(3)
O4 C14 . 1.350(3)
O4 C13 . 1.451(2)
O5 C14 . 1.199(3)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 C10 . 1.366(3)
C2 C3 . 1.380(3)
C3 C4 . 1.378(3)
C4 C5 . 1.413(3)
C5 C9 . 1.398(3)
C5 C6 . 1.517(3)
C6 C13 . 1.546(3)
C6 H6A . 1.0000
C7 C8 . 1.508(4)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 C9 . 1.500(3)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 C10 . 1.394(3)
C10 H10A . 0.9500
C11A H11A . 0.9800
C11A H11B . 0.9800
C11A H11C . 0.9800
C13 C20 . 1.496(3)
C13 H13A . 1.0000
C14 C15 . 1.472(4)
C15 C16 . 1.381(3)
C15 C20 . 1.382(3)
C16 C17 . 1.406(4)
C16 O6B . 1.425(5)
C16 O6A . 1.455(4)
C17 C18 . 1.391(4)
C17 O7A . 1.392(4)
C17 O7B . 1.457(7)
C18 C19 . 1.392(3)
C18 H18A . 0.9500
C19 C20 . 1.373(3)
C19 H19A . 0.9500
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
O6A C22A . 1.382(6)
C22A H22A . 0.9800
C22A H22B . 0.9800
C22A H22C . 0.9800
O6B C22B . 1.447(10)
C22B H22D . 0.9800
C22B H22E . 0.9800
C22B H22F . 0.9800
C21A O7A . 1.426(7)
C21A H21A . 0.9800
C21A H21B . 0.9800
C21A H21C . 0.9800
C21B O7B . 1.436(14)
C21B H21D . 0.9800
C21B H21E . 0.9800
C21B H21F . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6A O1 2_745 1.00 2.54 3.533(3) 172
C13 H13A O2 4_576 1.00 2.44 3.317(3) 146
C18 H18A O5 4_575 0.95 2.34 3.120(3) 140
