#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504894.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_1504894
loop_
_publ_author_name
'Smith, 3rd, Amos B'
'Liu, Zhuqing'
_publ_section_title
;
 Total synthesis of (-)-aplaminal.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4363
_journal_page_last               4365
_journal_paper_doi               10.1021/ol801794f
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C23 H26 N2 O7'
_chemical_formula_weight         442.46
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.793(8)
_cell_angle_beta                 78.913(9)
_cell_angle_gamma                74.581(7)
_cell_formula_units_Z            2
_cell_length_a                   8.1331(8)
_cell_length_b                   10.3107(9)
_cell_length_c                   13.9669(13)
_cell_measurement_temperature    143(1)
_cell_volume                     1080.05(18)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9273
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8308
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0688P)²+0.3562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                3031
_reflns_number_total             3788
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801794f_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1080.05(17)
_cod_original_sg_symbol_H-M      'P -1       '
_cod_database_code               1504894
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.5762(2) 0.70010(18) 0.54019(12) 0.0218(4) Uani 1 1 d .
C2 C 0.6813(3) 0.7840(2) 0.37092(14) 0.0330(5) Uani 1 1 d .
H2 H 0.5762 0.8358 0.3416 0.044 Uiso 1 1 calc R
C3 C 0.7265(2) 0.86684(19) 0.43241(12) 0.0241(4) Uani 1 1 d .
H3A H 0.8496 0.8450 0.4342 0.032 Uiso 1 1 calc R
H3B H 0.6882 0.9651 0.4056 0.032 Uiso 1 1 calc R
C4 C 0.6641(2) 0.86568(18) 0.61394(13) 0.0225(4) Uani 1 1 d .
C5 C 0.5920(2) 0.81605(19) 0.71255(13) 0.0263(4) Uani 1 1 d .
H5 H 0.5198 0.7555 0.7245 0.035 Uiso 1 1 calc R
C6 C 0.6275(2) 0.8562(2) 0.79150(13) 0.0278(4) Uani 1 1 d .
H6 H 0.5806 0.8207 0.8562 0.037 Uiso 1 1 calc R
C7 C 0.7319(2) 0.94895(19) 0.77650(13) 0.0269(4) Uani 1 1 d .
C8 C 0.8005(2) 1.00038(19) 0.67895(13) 0.0266(4) Uani 1 1 d .
H8 H 0.8702 1.0627 0.6674 0.035 Uiso 1 1 calc R
C9 C 0.7672(2) 0.96079(19) 0.59903(13) 0.0245(4) Uani 1 1 d .
H9 H 0.8136 0.9975 0.5345 0.033 Uiso 1 1 calc R
C10 C 0.7742(3) 0.9934(2) 0.85976(14) 0.0302(4) Uani 1 1 d .
C11 C 0.7414(3) 0.9650(2) 1.03572(15) 0.0444(6) Uani 1 1 d .
H11A H 0.8638 0.9455 1.0348 0.067 Uiso 1 1 calc R
H11B H 0.6917 0.9111 1.0958 0.067 Uiso 1 1 calc R
H11C H 0.6939 1.0614 1.0337 0.067 Uiso 1 1 calc R
C12 C 0.6621(2) 0.57741(19) 0.61993(13) 0.0237(4) Uani 1 1 d .
C13 C 0.6218(3) 0.3786(2) 0.74340(15) 0.0374(5) Uani 1 1 d .
H13A H 0.7104 0.3175 0.7097 0.056 Uiso 1 1 calc R
H13B H 0.5319 0.3324 0.7776 0.056 Uiso 1 1 calc R
H13C H 0.6695 0.4055 0.7910 0.056 Uiso 1 1 calc R
C14 C 0.3784(2) 0.72442(18) 0.56424(12) 0.0220(4) Uani 1 1 d .
C15 C 0.1352(2) 0.6552(2) 0.54463(16) 0.0348(5) Uani 1 1 d .
H15A H 0.1165 0.5997 0.6109 0.052 Uiso 1 1 calc R
H15B H 0.0975 0.6188 0.4982 0.052 Uiso 1 1 calc R
H15C H 0.0713 0.7484 0.5429 0.052 Uiso 1 1 calc R
C16 C 0.8210(3) 0.7475(2) 0.29023(14) 0.0358(5) Uani 1 1 d .
H16A H 0.8450 0.8309 0.2442 0.048 Uiso 1 1 calc R
H16B H 0.9251 0.6957 0.3189 0.048 Uiso 1 1 calc R
C17 C 0.9126(3) 0.6015(2) 0.17671(15) 0.0349(5) Uani 1 1 d .
H17A H 1.0006 0.5444 0.2176 0.046 Uiso 1 1 calc R
H17B H 0.9619 0.6709 0.1268 0.046 Uiso 1 1 calc R
C18 C 0.8522(3) 0.5142(2) 0.12623(14) 0.0310(5) Uani 1 1 d .
C19 C 0.8761(3) 0.3727(2) 0.16280(15) 0.0406(5) Uani 1 1 d .
H19 H 0.9297 0.3310 0.2199 0.054 Uiso 1 1 calc R
C20 C 0.8207(3) 0.2928(2) 0.11508(17) 0.0470(6) Uani 1 1 d .
H20 H 0.8372 0.1980 0.1402 0.062 Uiso 1 1 calc R
C21 C 0.7413(3) 0.3541(2) 0.03028(17) 0.0443(6) Uani 1 1 d .
H21 H 0.7040 0.3008 -0.0018 0.059 Uiso 1 1 calc R
C22 C 0.7173(3) 0.4944(2) -0.00668(16) 0.0397(5) Uani 1 1 d .
H22 H 0.6638 0.5358 -0.0638 0.053 Uiso 1 1 calc R
C23 C 0.7723(3) 0.5739(2) 0.04087(14) 0.0342(5) Uani 1 1 d .
H23 H 0.7556 0.6686 0.0153 0.045 Uiso 1 1 calc R
N1 N 0.6470(2) 0.66360(17) 0.44462(11) 0.0296(4) Uani 1 1 d .
N2 N 0.63404(19) 0.82489(15) 0.53279(10) 0.0230(4) Uani 1 1 d .
O1 O 0.70349(19) 0.93079(15) 0.94964(9) 0.0356(4) Uani 1 1 d .
O2 O 0.8604(2) 1.07570(17) 0.85044(11) 0.0464(4) Uani 1 1 d .
O3 O 0.55140(16) 0.50115(13) 0.67025(9) 0.0267(3) Uani 1 1 d .
O4 O 0.81008(18) 0.55375(15) 0.63102(11) 0.0389(4) Uani 1 1 d .
O5 O 0.31756(16) 0.65306(13) 0.51720(9) 0.0274(3) Uani 1 1 d .
O6 O 0.29088(16) 0.79687(13) 0.61869(9) 0.0275(3) Uani 1 1 d .
O7 O 0.76933(17) 0.66688(15) 0.23810(9) 0.0318(3) Uani 1 1 d .
H1 H 0.5829 0.6101 0.4202 0.040 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
N1 C1 N2 103.64(13)
N1 C1 C14 114.78(15)
N2 C1 C14 111.35(14)
N1 C1 C12 105.28(14)
N2 C1 C12 111.67(14)
C14 C1 C12 109.88(13)
N1 C2 C16 112.08(18)
N1 C2 C3 102.91(14)
C16 C2 C3 113.17(16)
N2 C3 C2 104.00(14)
N2 C4 C9 120.16(15)
N2 C4 C5 122.12(16)
C9 C4 C5 117.71(16)
C6 C5 C4 120.63(17)
C5 C6 C7 121.42(17)
C8 C7 C6 118.09(17)
C8 C7 C10 119.05(17)
C6 C7 C10 122.86(17)
C9 C8 C7 121.33(17)
C8 C9 C4 120.78(16)
O2 C10 O1 122.76(17)
O2 C10 C7 125.32(18)
O1 C10 C7 111.92(16)
O4 C12 O3 125.28(17)
O4 C12 C1 123.58(16)
O3 C12 C1 111.09(15)
O6 C14 O5 124.57(16)
O6 C14 C1 124.57(16)
O5 C14 C1 110.85(15)
O7 C16 C2 109.30(16)
O7 C17 C18 108.97(16)
C23 C18 C19 118.5(2)
C23 C18 C17 120.33(19)
C19 C18 C17 121.16(19)
C18 C19 C20 120.7(2)
C21 C20 C19 119.9(2)
C22 C21 C20 119.8(2)
C21 C22 C23 120.2(2)
C22 C23 C18 120.8(2)
C2 N1 C1 109.82(15)
C4 N2 C1 124.41(14)
C4 N2 C3 120.51(14)
C1 N2 C3 110.18(13)
C10 O1 C11 115.91(16)
C12 O3 C13 115.50(14)
C14 O5 C15 115.13(14)
C16 O7 C17 111.17(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.452(2)
C1 N2 1.456(2)
C1 C14 1.545(3)
C1 C12 1.555(2)
C2 N1 1.443(2)
C2 C16 1.485(3)
C2 C3 1.508(3)
C3 N2 1.472(2)
C4 N2 1.390(2)
C4 C9 1.404(3)
C4 C5 1.408(2)
C5 C6 1.377(3)
C6 C7 1.392(3)
C7 C8 1.391(3)
C7 C10 1.482(3)
C8 C9 1.378(3)
C10 O2 1.205(2)
C10 O1 1.348(2)
C11 O1 1.445(2)
C12 O4 1.195(2)
C12 O3 1.329(2)
C13 O3 1.460(2)
C14 O6 1.204(2)
C14 O5 1.338(2)
C15 O5 1.454(2)
C16 O7 1.421(2)
C17 O7 1.431(2)
C17 C18 1.500(3)
C18 C23 1.387(3)
C18 C19 1.387(3)
C19 C20 1.388(3)
C20 C21 1.380(3)
C21 C22 1.376(3)
C22 C23 1.382(3)
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_site_symmetry_A
N1 H1 O3 1.01 2.46 3.456(2) 169.5 2_666
N1 H1 O5 1.01 2.58 3.110(2) 112.9 2_666
