#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200041.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_2200041
loop_
_publ_author_name
'Cox, Philip J.'
'Fergusson, Margot'
'Nahar, Lutfun'
'Sarker, Satyajit D.'
_publ_section_title
;
 Moschamindole
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o81
_journal_page_last               o82
_journal_paper_doi               10.1107/S1600536800020730
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_chemical_name_common            Moschamindole
_chemical_name_systematic
;
{2-(3-methoxy-4-hydroxyphenyl)}-dihydrofuro[kl]-1H-
pyrrolo[fg]-2-oxo-1,2,3,4,5,6-hexahydro-3-benzazocine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.840(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8724(3)
_cell_length_b                   15.2803(9)
_cell_length_c                   10.6940(7)
_cell_measurement_reflns_used    3310
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     779.25(8)
_computing_cell_refinement       'DENZO and COLLECT'
_computing_data_collection
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full .994
_diffrn_measured_fraction_theta_max .994
_diffrn_measurement_device_type  'Enraf Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .080
_diffrn_reflns_av_sigmaI/netI    .100
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5565
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.3
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .11
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .05
_refine_diff_density_max         .22
_refine_diff_density_min         -.28
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .99
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         1839
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      .99
_refine_ls_R_factor_all          .088
_refine_ls_R_factor_gt           .046
_refine_ls_shift/su_max          .007
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0348P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .097
_reflns_number_gt                1272
_reflns_number_total             1839
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf6033.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (25
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'N' changed to 'n'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (25
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (36
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (67 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2200041
_cod_database_fobs_code          2200041
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
O1 1.0233(5) .56379(17) .8951(2) .0272(6) Uani d . 1 . . O
O2 .8375(5) .37968(15) .6439(2) .0277(6) Uani d . 1 . . O
O3 .2063(5) .29402(17) 1.0335(2) .0302(6) Uani d . 1 . . O
O4 .3312(5) .37320(18) 1.2564(2) .0287(6) Uani d . 1 . . O
H4 .188(8) .326(3) 1.229(3) .034 Uiso d . 1 . . H
N1 .4571(6) .4431(2) .5244(3) .0253(7) Uani d . 1 . . N
H1 .452(8) .409(3) .469(4) .030 Uiso d . 1 . . H
N2 .8203(7) .7503(2) .4526(3) .0301(8) Uani d . 1 . . N
H2 .922(8) .784(3) .435(3) .036 Uiso d . 1 . . H
C1 .8558(7) .4855(2) .8585(3) .0210(8) Uani d . 1 . . C
H1A .9837 .4376 .8422 .025 Uiso calc R 1 . . H
C2 .6525(7) .5072(2) .7311(3) .0202(8) Uani d . 1 . . C
H2A .4580 .5169 .7451 .024 Uiso calc R 1 . . H
C3 .6552(7) .4363(2) .6300(3) .0198(7) Uani d . 1 . . C
C4 .2289(7) .5057(3) .4966(3) .0249(8) Uani d . 1 . . C
H4A .2013 .5319 .5778 .030 Uiso calc R 1 . . H
H4B .0544 .4744 .4578 .030 Uiso calc R 1 . . H
C5 .2770(7) .5787(2) .4074(3) .0262(9) Uani d . 1 . . C
H5A .3016 .5521 .3259 .031 Uiso calc R 1 . . H
H5B .1063 .6155 .3883 .031 Uiso calc R 1 . . H
C6 .5239(7) .6368(2) .4562(3) .0242(8) Uani d . 1 . . C
C7 .7173(7) .6401(2) .5761(3) .0229(8) Uani d . 1 . . C
C8 .7749(7) .5910(2) .6915(3) .0183(7) Uani d . 1 . . C
C9 .9907(7) .6167(2) .7875(3) .0244(8) Uani d . 1 . . C
C10 1.1662(7) .6868(3) .7815(3) .0284(9) Uani d . 1 . . C
H10 1.3128 .7014 .8517 .034 Uiso calc . 1 . . H
C11 1.1207(7) .7352(2) .6697(4) .0288(9) Uani d . 1 . . C
H11 1.2379 .7835 .6605 .035 Uiso calc . 1 . . H
C12 .9010(7) .7118(2) .5717(3) .0249(8) Uani d . 1 . . C
C13 .5985(8) .7047(3) .3855(3) .0297(9) Uani d . 1 . . C
H13 .5065 .7181 .3005 .036 Uiso calc . 1 . . H
C14 .7172(7) .4572(2) .9658(3) .0211(8) Uani d . 1 . . C
C15 .7808(7) .4961(2) 1.0836(3) .0254(8) Uani d . 1 . . C
H15 .9135 .5424 1.0987 .031 Uiso calc . 1 . . H
C16 .6509(7) .4678(3) 1.1822(3) .0265(8) Uani d . 1 . . C
H16 .6957 .4948 1.2639 .032 Uiso calc . 1 . . H
C17 .4596(7) .4013(2) 1.1600(3) .0235(8) Uani d . 1 . . C
C18 .3967(7) .3605(2) 1.0414(3) .0224(8) Uani d . 1 . . C
C19 .5267(7) .3883(2) .9439(3) .0243(8) Uani d . 1 . . C
H19 .4855 .3603 .8628 .029 Uiso calc . 1 . . H
C20 .1393(9) .2442(3) .9195(3) .0347(9) Uani d . 1 . . C
H20A .0760 .2834 .8468 .042 Uiso calc R 1 . . H
H20B -.0104 .2026 .9258 .042 Uiso calc R 1 . . H
H20C .3059 .2121 .9072 .042 Uiso calc R 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
_geom_angle_publ_flag
C9 O1 C1 107.0(2) n
C18 O3 C20 119.1(3) n
C3 N1 C4 128.1(3) n
C13 N2 C12 108.2(3) n
O1 C1 C14 110.2(3) n
O1 C1 C2 106.5(3) n
C14 C1 C2 115.2(3) n
C8 C2 C3 109.9(2) n
C8 C2 C1 102.1(3) n
C3 C2 C1 111.9(3) n
O2 C3 N1 122.6(3) n
O2 C3 C2 121.6(3) n
N1 C3 C2 115.8(3) n
N1 C4 C5 113.8(3) n
C6 C5 C4 115.6(3) n
C13 C6 C7 105.5(3) y
C13 C6 C5 122.6(3) y
C7 C6 C5 131.9(3) y
C12 C7 C8 114.9(3) y
C12 C7 C6 107.5(3) y
C8 C7 C6 137.5(3) y
C9 C8 C7 119.0(3) y
C9 C8 C2 108.7(3) y
C7 C8 C2 132.2(3) y
C8 C9 C10 125.2(3) n
C8 C9 O1 113.2(3) n
C10 C9 O1 121.6(3) n
C9 C10 C11 117.6(3) n
C12 C11 C10 118.6(3) n
C11 C12 N2 128.1(3) n
C11 C12 C7 124.6(3) n
N2 C12 C7 107.2(3) n
N2 C13 C6 111.5(3) n
C15 C14 C19 120.0(3) n
C15 C14 C1 121.5(3) n
C19 C14 C1 118.5(3) n
C14 C15 C16 120.4(3) n
C17 C16 C15 119.6(3) n
C16 C17 O4 119.9(3) n
C16 C17 C18 120.5(3) n
O4 C17 C18 119.6(3) n
O3 C18 C17 114.2(3) n
O3 C18 C19 125.9(3) n
C17 C18 C19 119.8(3) n
C14 C19 C18 119.7(3) n
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
O1 C9 . 1.389(4) n
O1 C1 . 1.456(4) n
O2 C3 . 1.227(4) y
O3 C18 . 1.366(4) n
O3 C20 . 1.417(4) n
O4 C17 . 1.380(4) n
N1 C3 . 1.331(4) n
N1 C4 . 1.451(5) n
N2 C13 . 1.360(5) n
N2 C12 . 1.384(4) n
C1 C14 . 1.509(5) y
C1 C2 . 1.546(4) n
C2 C8 . 1.510(5) n
C2 C3 . 1.532(5) n
C4 C5 . 1.516(5) n
C5 C6 . 1.500(5) n
C6 C13 . 1.376(5) y
C6 C7 . 1.428(5) n
C7 C12 . 1.422(5) y
C7 C8 . 1.422(5) n
C8 C9 . 1.367(4) y
C9 C10 . 1.380(5) n
C10 C11 . 1.384(5) n
C11 C12 . 1.383(5) n
C14 C15 . 1.370(5) n
C14 C19 . 1.391(5) n
C15 C16 . 1.404(5) n
C16 C17 . 1.367(5) n
C17 C18 . 1.389(5) n
C18 C19 . 1.393(4) n
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
N1 H1 O4 1_554 .79(4) 2.29(4) 3.002(4) 150(4)
N2 H2 O2 2_756 .76(4) 2.15(4) 2.909(4) 171(3)
O4 H4 O3 . 1.00(4) 2.17(3) 2.631(5) 106(2)
C1 H1A O2 . 1.00 2.27 2.794(4) 111
C11 H11 O4 2_757 .95 2.51 3.367(4) 150
C15 H15 O1 . .94 2.37 2.740(4) 103
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
_geom_torsion_publ_flag
C9 O1 C1 C14 -141.6(3) n
C9 O1 C1 C2 -16.1(3) n
O1 C1 C2 C8 13.1(3) n
C14 C1 C2 C8 135.5(3) n
O1 C1 C2 C3 130.6(3) n
C14 C1 C2 C3 -107.0(3) n
C4 N1 C3 O2 179.1(3) n
C4 N1 C3 C2 -4.2(4) n
C8 C2 C3 O2 99.8(4) n
C1 C2 C3 O2 -12.9(4) n
C8 C2 C3 N1 -76.9(3) n
C1 C2 C3 N1 170.4(3) n
C3 N1 C4 C5 103.1(4) n
N1 C4 C5 C6 -62.5(4) n
C4 C5 C6 C13 178.7(3) n
C4 C5 C6 C7 -4.4(5) n
C13 C6 C7 C12 .4(4) n
C5 C6 C7 C12 -176.9(3) n
C13 C6 C7 C8 -177.4(4) n
C5 C6 C7 C8 5.2(7) n
C12 C7 C8 C9 1.5(4) n
C6 C7 C8 C9 179.2(4) n
C12 C7 C8 C2 -173.6(3) n
C6 C7 C8 C2 4.1(6) n
C3 C2 C8 C9 -124.7(3) n
C1 C2 C8 C9 -5.7(3) n
C3 C2 C8 C7 50.8(5) n
C1 C2 C8 C7 169.8(3) n
C7 C8 C9 C10 -1.4(5) n
C2 C8 C9 C10 174.8(3) n
C7 C8 C9 O1 179.5(3) n
C2 C8 C9 O1 -4.3(4) n
C1 O1 C9 C8 13.1(4) n
C1 O1 C9 C10 -166.0(3) n
C8 C9 C10 C11 .0(5) n
O1 C9 C10 C11 179.1(3) n
C9 C10 C11 C12 1.1(5) n
C10 C11 C12 N2 -179.4(3) n
C10 C11 C12 C7 -.9(5) n
C13 N2 C12 C11 178.4(3) n
C13 N2 C12 C7 -.3(4) n
C8 C7 C12 C11 -.4(5) n
C6 C7 C12 C11 -178.8(3) n
C8 C7 C12 N2 178.3(3) n
C6 C7 C12 N2 -.1(4) n
C12 N2 C13 C6 .6(4) n
C7 C6 C13 N2 -.7(4) n
C5 C6 C13 N2 177.0(3) n
O1 C1 C14 C15 -7.8(5) n
C2 C1 C14 C15 -128.3(4) n
O1 C1 C14 C19 173.9(3) n
C2 C1 C14 C19 53.5(4) n
C19 C14 C15 C16 -1.1(5) n
C1 C14 C15 C16 -179.4(3) n
C14 C15 C16 C17 -.1(5) n
C15 C16 C17 O4 180.0(3) n
C15 C16 C17 C18 1.1(5) n
C20 O3 C18 C17 -176.1(3) n
C20 O3 C18 C19 3.4(5) n
C16 C17 C18 O3 178.8(3) n
O4 C17 C18 O3 -.1(5) n
C16 C17 C18 C19 -.8(5) n
O4 C17 C18 C19 -179.7(3) n
C15 C14 C19 C18 1.4(5) n
C1 C14 C19 C18 179.7(3) n
O3 C18 C19 C14 180.0(3) n
C17 C18 C19 C14 -.5(5) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24730972
