#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/49/1504930.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_1504930
loop_
_publ_author_name
'Lévesque, François'
'Bélanger, Guillaume'
_publ_section_title
;
 A versatile cascade of intramolecular Vilsmeier-Haack and azomethine
 ylide 1,3-dipolar cycloaddition toward tricyclic cores of alkaloids.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4939
_journal_page_last               4942
_journal_paper_doi               10.1021/ol802010n
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_sum            'C16 H23 N O5'
_chemical_formula_weight         309.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-02-05T12:46:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.221(5)
_cell_length_b                   10.099(3)
_cell_length_c                   20.920(13)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     1525.6(15)
_computing_cell_refinement       Difrac
_computing_data_collection       Difrac
_computing_data_reduction        NRCVAX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      198(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       Omega/2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1659
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.57
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_correction_T_min  0.9518
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   Empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1234
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0413P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                976
_reflns_number_total             1659
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol802010n_si_002.cif
_cod_data_source_block           fl892
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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 'Psi-Scan'
changed to 'psi-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        1525.6(14)
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1504930
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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 0.3424(7) 0.3880(4) 0.1129(2) 0.0290(11) Uani 1 1 d .
C2 C 0.3802(6) 0.5297(4) 0.0935(2) 0.0270(11) Uani 1 1 d .
H2 H 0.314 0.5436 0.052 0.032 Uiso 1 1 calc R
C3 C 0.3113(6) 0.6444(4) 0.14014(18) 0.0252(10) Uani 1 1 d .
H3 H 0.1953 0.684 0.1224 0.03 Uiso 1 1 calc R
C4 C 0.4671(7) 0.7474(4) 0.13649(19) 0.0293(11) Uani 1 1 d .
H4 H 0.5407 0.7431 0.1769 0.035 Uiso 1 1 calc R
C5 C 0.4049(7) 0.8916(4) 0.1257(2) 0.0376(12) Uani 1 1 d .
H5A H 0.2766 0.893 0.109 0.045 Uiso 1 1 calc R
H5B H 0.4068 0.9401 0.1668 0.045 Uiso 1 1 calc R
C6 C 0.5331(8) 0.9581(4) 0.0787(2) 0.0434(13) Uani 1 1 d .
H6A H 0.4984 1.0525 0.0739 0.052 Uiso 1 1 calc R
H6B H 0.6621 0.954 0.0946 0.052 Uiso 1 1 calc R
C7 C 0.5363(7) 0.7577(5) 0.0176(2) 0.0322(12) Uani 1 1 d .
C8 C 0.5905(7) 0.6980(4) 0.08046(19) 0.0298(11) Uani 1 1 d .
H8 H 0.7217 0.7235 0.0897 0.036 Uiso 1 1 calc R
C9 C 0.7045(7) 0.4955(5) 0.1278(2) 0.0430(14) Uani 1 1 d .
H9A H 0.6848 0.538 0.1699 0.052 Uiso 1 1 calc R
H9B H 0.8343 0.5115 0.1147 0.052 Uiso 1 1 calc R
C10 C 0.6709(7) 0.3491(5) 0.1333(3) 0.0457(14) Uani 1 1 d .
H10A H 0.761 0.3101 0.1636 0.055 Uiso 1 1 calc R
H10B H 0.6895 0.3068 0.0911 0.055 Uiso 1 1 calc R
C11 C 0.4746(7) 0.3220(4) 0.1566(2) 0.0424(14) Uani 1 1 d .
H11A H 0.451 0.2254 0.1573 0.051 Uiso 1 1 calc R
H11B H 0.4589 0.3565 0.2006 0.051 Uiso 1 1 calc R
C12 C 0.1941(7) 0.3291(4) 0.0869(2) 0.0305(11) Uani 1 1 d .
H12 H 0.123 0.3754 0.0559 0.037 Uiso 1 1 calc R
C13 C 0.0515(8) 0.1334(4) 0.0541(2) 0.0473(15) Uani 1 1 d .
H13A H -0.0416 0.1911 0.0344 0.071 Uiso 1 1 calc R
H13B H -0.0091 0.0545 0.0715 0.071 Uiso 1 1 calc R
H13C H 0.1424 0.1068 0.0217 0.071 Uiso 1 1 calc R
C14 C 0.2747(7) 0.5982(4) 0.2072(2) 0.0318(12) Uani 1 1 d .
C15 C 0.0371(8) 0.5203(4) 0.2773(2) 0.0507(15) Uani 1 1 d .
H15A H -0.0956 0.5409 0.2838 0.061 Uiso 1 1 calc R
H15B H 0.1088 0.5668 0.3108 0.061 Uiso 1 1 calc R
C16 C 0.0659(8) 0.3757(4) 0.2836(2) 0.0519(15) Uani 1 1 d .
H16A H 0.0016 0.3298 0.2488 0.078 Uiso 1 1 calc R
H16B H 0.0166 0.3455 0.3248 0.078 Uiso 1 1 calc R
H16C H 0.1987 0.356 0.2815 0.078 Uiso 1 1 calc R
N1 N 0.5782(5) 0.5541(3) 0.08047(17) 0.0275(9) Uani 1 1 d .
O1 O 0.1430(5) 0.2029(3) 0.10426(13) 0.0438(9) Uani 1 1 d .
O2 O 0.3867(5) 0.5888(3) 0.24945(14) 0.0473(10) Uani 1 1 d .
O3 O 0.0952(5) 0.5678(3) 0.21420(14) 0.0394(9) Uani 1 1 d .
O4 O 0.5203(5) 0.8920(3) 0.01744(13) 0.0394(9) Uani 1 1 d .
O5 O 0.5095(5) 0.6997(3) -0.03170(13) 0.0381(9) Uani 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 0 '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 0.006 '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
C12 C1 C11 124.5(4)
C12 C1 C2 117.1(4)
C11 C1 C2 118.4(4)
N1 C2 C1 112.5(4)
N1 C2 C3 107.1(4)
C1 C2 C3 117.8(3)
C14 C3 C4 112.7(4)
C14 C3 C2 113.6(3)
C4 C3 C2 103.5(3)
C3 C4 C5 115.8(4)
C3 C4 C8 103.9(3)
C5 C4 C8 111.1(3)
C6 C5 C4 109.7(4)
O4 C6 C5 109.4(4)
O5 C7 O4 118.0(4)
O5 C7 C8 126.8(4)
O4 C7 C8 115.2(4)
N1 C8 C7 112.7(4)
N1 C8 C4 106.5(3)
C7 C8 C4 112.5(4)
N1 C9 C10 110.3(4)
C9 C10 C11 110.6(4)
C1 C11 C10 108.7(4)
C1 C12 O1 121.2(4)
O2 C14 O3 123.5(5)
O2 C14 C3 126.4(5)
O3 C14 C3 110.1(4)
O3 C15 C16 111.3(4)
C8 N1 C9 111.4(4)
C8 N1 C2 103.1(3)
C9 N1 C2 114.2(4)
C12 O1 C13 112.7(3)
C14 O3 C15 116.8(4)
C7 O4 C6 116.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C12 1.340(6)
C1 C11 1.480(6)
C1 C2 1.513(6)
C2 N1 1.476(5)
C2 C3 1.595(5)
C3 C14 1.501(6)
C3 C4 1.534(5)
C4 C5 1.541(5)
C4 C8 1.555(5)
C5 C6 1.509(6)
C6 O4 1.448(5)
C7 O5 1.202(5)
C7 O4 1.362(5)
C7 C8 1.498(6)
C8 N1 1.456(5)
C9 N1 1.471(5)
C9 C10 1.502(6)
C10 C11 1.524(7)
C12 O1 1.375(5)
C13 O1 1.426(5)
C14 O2 1.202(5)
C14 O3 1.341(6)
C15 O3 1.466(5)
C15 C16 1.481(6)
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
C12 C1 C2 N1 -136.7(4)
C11 C1 C2 N1 40.5(5)
C12 C1 C2 C3 98.0(5)
C11 C1 C2 C3 -84.7(5)
N1 C2 C3 C14 -108.4(4)
C1 C2 C3 C14 19.5(6)
N1 C2 C3 C4 14.2(4)
C1 C2 C3 C4 142.1(4)
C14 C3 C4 C5 -104.7(4)
C2 C3 C4 C5 132.1(4)
C14 C3 C4 C8 133.2(4)
C2 C3 C4 C8 10.0(4)
C3 C4 C5 C6 -138.8(4)
C8 C4 C5 C6 -20.6(5)
C4 C5 C6 O4 63.2(5)
O5 C7 C8 N1 -10.2(7)
O4 C7 C8 N1 171.2(4)
O5 C7 C8 C4 -130.6(5)
O4 C7 C8 C4 50.8(6)
C3 C4 C8 N1 -31.9(4)
C5 C4 C8 N1 -157.0(4)
C3 C4 C8 C7 92.1(4)
C5 C4 C8 C7 -33.1(5)
N1 C9 C10 C11 -62.1(5)
C12 C1 C11 C10 130.9(5)
C2 C1 C11 C10 -46.2(5)
C9 C10 C11 C1 55.8(5)
C11 C1 C12 O1 6.4(7)
C2 C1 C12 O1 -176.5(4)
C4 C3 C14 O2 -31.6(6)
C2 C3 C14 O2 85.8(5)
C4 C3 C14 O3 148.4(4)
C2 C3 C14 O3 -94.3(5)
C7 C8 N1 C9 154.3(4)
C4 C8 N1 C9 -81.9(4)
C7 C8 N1 C2 -82.9(5)
C4 C8 N1 C2 41.0(4)
C10 C9 N1 C8 172.3(4)
C10 C9 N1 C2 56.1(5)
C1 C2 N1 C8 -164.9(3)
C3 C2 N1 C8 -34.0(4)
C1 C2 N1 C9 -43.9(5)
C3 C2 N1 C9 87.0(4)
C1 C12 O1 C13 -150.7(4)
O2 C14 O3 C15 -0.3(6)
C3 C14 O3 C15 179.8(3)
C16 C15 O3 C14 -85.6(5)
O5 C7 O4 C6 173.4(4)
C8 C7 O4 C6 -7.9(6)
C5 C6 O4 C7 -49.7(6)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651515 ChemSpider
