#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/37/4023707.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_4023707
loop_
_publ_author_name
'An-Wei Hong'
'Tsung-Hui Cheng'
'Vellingiri Raghukumar'
'Chin-Kang Sha'
_publ_contact_author_address
;
Department of Chemistry, 
National Tsing Hua University,
Hsinchu 300, Taiwan, ROC
;
_publ_contact_author_email       cksha@mx.nthu.edu.tw
_publ_contact_author_fax         '+886 3 5725870'
_publ_contact_author_name        'Dr. Chin-Kang Sha'
_publ_contact_author_phone       '+886 3 5722427'
_publ_section_title
;
 An Expedient Route to Montanine-Type Amaryllidaceae Alkaloids:
 Total Syntheses of (-)-Brunsvigine and (-)-Manthine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7580
_journal_page_last               7585
_journal_paper_doi               10.1021/jo801089y
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C20 H21 N O6'
_chemical_formula_weight         371.38
_chemical_name_common            '(-)-brunsvigine diacetate'
_chemical_name_systematic
; 
 (1S,13S,15R,16S)-15-(Methylcarbonyloxy)5,7-dioxa-12-azapentacyclo
 [10.6.1.02,10.04,8.013,18]nonadeca-2(10),3,8,17-tetraen-16-ylacetate
;
_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'
_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                 97.7580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8014(3)
_cell_length_b                   5.51980(10)
_cell_length_c                   14.1673(4)
_cell_measurement_reflns_used    3610
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     914.43(4)
_computing_cell_refinement       'Siemens Smart'
_computing_data_collection       'Siemens Smart CCD'
_computing_data_reduction        'Siemens Saint'
_computing_molecular_graphics    'Siemens Shelxtl'
_computing_publication_material  'Siemens Shelxtl'
_computing_structure_refinement  'Siemens SHELXTL PLUS (VNS)'
_computing_structure_solution    'Siemens SHELXTL PLUS (VNS)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_method       'phi and omega scans'
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5138
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.93737
_exptl_absorpt_correction_T_min  0.60116
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             392
_exptl_crystal_size_max          90.81
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(14)
_refine_ls_extinction_coef       0.028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0723P)²+0.2134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                3185
_reflns_number_total             3439
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo801089y_si_003.cif
_cod_data_source_block           ot12m
_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.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023707
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19234(19) 0.8503 0.13436(15) 0.0741(6) Uani 1 1 d . . .
O2 O 0.38514(19) 0.8471(7) 0.19625(16) 0.0742(6) Uani 1 1 d . . .
O3 O 0.14367(15) 0.3679(6) 0.78670(12) 0.0582(5) Uani 1 1 d . . .
O4 O 0.35768(14) 0.1967(6) 0.75866(11) 0.0515(4) Uani 1 1 d . . .
O5 O 0.1521(3) 0.7593(7) 0.8293(2) 0.0911(8) Uani 1 1 d . . .
O6 O 0.3766(2) 0.3813(7) 0.90221(14) 0.0718(6) Uani 1 1 d . . .
N1 N 0.13767(19) 0.1089(6) 0.45484(16) 0.0535(5) Uani 1 1 d . . .
C1 C 0.3000(3) 0.9608(11) 0.1286(3) 0.0967(13) Uani 1 1 d . . .
C2 C 0.2117(2) 0.6810(8) 0.20662(17) 0.0570(6) Uani 1 1 d . . .
C3 C 0.1334(2) 0.5342(7) 0.24238(18) 0.0566(6) Uani 1 1 d . . .
C4 C 0.1735(2) 0.3855(7) 0.32012(18) 0.0529(6) Uani 1 1 d . . .
C5 C 0.0907(2) 0.2193(7) 0.36280(19) 0.0587(6) Uani 1 1 d . . .
C6 C 0.1648(2) 0.3003(7) 0.52865(18) 0.0480(5) Uani 1 1 d . . .
C7 C 0.1321(2) 0.2346(7) 0.62557(18) 0.0513(6) Uani 1 1 d . . .
C8 C 0.1840(2) 0.4208(7) 0.69704(18) 0.0497(5) Uani 1 1 d . . .
C9 C 0.3154(2) 0.4180(7) 0.70970(18) 0.0505(6) Uani 1 1 d . . .
C10 C 0.3595(2) 0.4009(7) 0.61536(19) 0.0532(6) Uani 1 1 d . . .
C11 C 0.2944(2) 0.3386(7) 0.53568(17) 0.0489(6) Uani 1 1 d . . .
C12 C 0.3277(2) 0.2307(7) 0.44483(19) 0.0545(6) Uani 1 1 d . . .
C13 C 0.2900(2) 0.3834(7) 0.35778(17) 0.0524(6) Uani 1 1 d . . .
C14 C 0.3686(2) 0.5291(8) 0.31828(19) 0.0571(6) Uani 1 1 d . . .
C15 C 0.3266(2) 0.6786(7) 0.24303(19) 0.0569(6) Uani 1 1 d . . .
C16 C 0.2499(3) 0.0027(7) 0.4433(2) 0.0621(7) Uani 1 1 d . . .
C17 C 0.1353(3) 0.5510(9) 0.8485(2) 0.0670(8) Uani 1 1 d . . .
C18 C 0.1023(4) 0.4607(11) 0.9399(3) 0.0965(13) Uani 1 1 d . . .
C19 C 0.3884(2) 0.2051(8) 0.85421(17) 0.0543(6) Uani 1 1 d . . .
C20 C 0.4372(3) -0.0324(8) 0.8901(2) 0.0680(8) Uani 1 1 d . . .
H1A H 0.3234 1.0230 0.0775 0.080 Uiso 1 1 d . . .
H1B H 0.3056 1.1234 0.1526 0.080 Uiso 1 1 d . . .
H3A H 0.0503 0.5254 0.2124 0.080 Uiso 1 1 d . . .
H5A H 0.0185 0.3093 0.3784 0.080 Uiso 1 1 d . . .
H5B H 0.0699 0.0949 0.3223 0.080 Uiso 1 1 d . . .
H6A H 0.1267 0.4461 0.5086 0.080 Uiso 1 1 d . . .
H7A H 0.0491 0.2395 0.6265 0.080 Uiso 1 1 d . . .
H7B H 0.1590 0.0787 0.6411 0.080 Uiso 1 1 d . . .
H8A H 0.1594 0.5742 0.6771 0.080 Uiso 1 1 d . . .
H9A H 0.3516 0.5619 0.7517 0.080 Uiso 1 1 d . . .
H10A H 0.4374 0.4156 0.6215 0.080 Uiso 1 1 d . . .
H12A H 0.4104 0.1931 0.4483 0.080 Uiso 1 1 d . . .
H14A H 0.4479 0.5193 0.3455 0.080 Uiso 1 1 d . . .
H16A H 0.2468 -0.0849 0.3809 0.080 Uiso 1 1 d . . .
H16B H 0.2775 -0.1112 0.4979 0.080 Uiso 1 1 d . . .
H18A H 0.1055 0.6029 0.9803 0.080 Uiso 1 1 d . . .
H18B H 0.1043 0.2950 0.9378 0.080 Uiso 1 1 d . . .
H18C H 0.0119 0.4306 0.9332 0.080 Uiso 1 1 d . . .
H20A H 0.4748 0.0051 0.9450 0.080 Uiso 1 1 d . . .
H20B H 0.4793 -0.0842 0.8451 0.080 Uiso 1 1 d . . .
H20C H 0.3607 -0.1327 0.9020 0.080 Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 105.8(2) . . ?
C15 O2 C1 105.3(2) . . ?
C17 O3 C8 118.7(2) . . ?
C19 O4 C9 118.4(2) . . ?
C16 N1 C5 107.5(2) . . ?
C16 N1 C6 104.4(2) . . ?
C5 N1 C6 110.3(2) . . ?
O1 C1 O2 108.9(3) . . ?
C3 C2 O1 128.2(3) . . ?
C3 C2 C15 122.0(3) . . ?
O1 C2 C15 109.7(3) . . ?
C2 C3 C4 117.4(2) . . ?
C3 C4 C13 120.8(2) . . ?
C3 C4 C5 119.8(2) . . ?
C13 C4 C5 119.4(2) . . ?
N1 C5 C4 114.4(2) . . ?
N1 C6 C7 114.1(2) . . ?
N1 C6 C11 105.1(2) . . ?
C7 C6 C11 110.28(19) . . ?
C8 C7 C6 108.3(2) . . ?
O3 C8 C7 107.4(2) . . ?
O3 C8 C9 110.0(2) . . ?
C7 C8 C9 112.5(2) . . ?
O4 C9 C10 103.5(2) . . ?
O4 C9 C8 109.8(2) . . ?
C10 C9 C8 111.3(2) . . ?
C11 C10 C9 123.0(2) . . ?
C10 C11 C12 129.7(2) . . ?
C10 C11 C6 123.4(2) . . ?
C12 C11 C6 105.1(2) . . ?
C13 C12 C11 113.1(2) . . ?
C13 C12 C16 109.4(2) . . ?
C11 C12 C16 96.3(2) . . ?
C14 C13 C4 120.7(2) . . ?
C14 C13 C12 120.6(2) . . ?
C4 C13 C12 118.6(2) . . ?
C15 C14 C13 117.5(2) . . ?
O2 C15 C2 110.1(3) . . ?
O2 C15 C14 128.4(2) . . ?
C2 C15 C14 121.5(3) . . ?
N1 C16 C12 102.3(2) . . ?
O5 C17 O3 122.7(3) . . ?
O5 C17 C18 125.9(3) . . ?
O3 C17 C18 111.3(3) . . ?
O6 C19 O4 123.8(3) . . ?
O6 C19 C20 125.8(2) . . ?
O4 C19 C20 110.4(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.382(4) . ?
O1 C1 1.422(5) . ?
O2 C15 1.380(4) . ?
O2 C1 1.436(5) . ?
O3 C17 1.350(4) . ?
O3 C8 1.445(3) . ?
O4 C19 1.354(3) . ?
O4 C9 1.459(3) . ?
O5 C17 1.204(5) . ?
O6 C19 1.206(4) . ?
N1 C16 1.477(4) . ?
N1 C5 1.478(4) . ?
N1 C6 1.490(3) . ?
C2 C3 1.376(4) . ?
C2 C15 1.385(4) . ?
C3 C4 1.404(4) . ?
C4 C13 1.406(3) . ?
C4 C5 1.524(4) . ?
C6 C7 1.519(3) . ?
C6 C11 1.534(3) . ?
C7 C8 1.513(4) . ?
C8 C9 1.537(3) . ?
C9 C10 1.501(4) . ?
C10 C11 1.322(4) . ?
C11 C12 1.518(3) . ?
C12 C13 1.510(4) . ?
C12 C16 1.556(4) . ?
C13 C14 1.400(4) . ?
C14 C15 1.386(4) . ?
C17 C18 1.488(5) . ?
C19 C20 1.493(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10390650
