#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/33/1513364.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_1513364
loop_
_publ_author_name
'Low, Yun-Yee'
'Hong, Fong-Jiao'
'Lim, Kuan-Hon'
'Thomas, Noel F.'
'Kam, Toh-Seok'
_publ_section_title
;
 Transformations of the 2,7-Seco Aspidosperma Alkaloid Leuconolam,
 Structure Revision of epi-Leuconolam, and Partial Syntheses of
 Leuconoxine and Leuconodines A and F.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              327
_journal_page_last               338
_journal_paper_doi               10.1021/np400922x
_journal_volume                  77
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H22 N2 O3.C H6 O'
_chemical_formula_sum            'C20 H26 N2 O4'
_chemical_formula_weight         358.43
_chemical_melting_point          452.1(10)
_chemical_name_common            leuconolam
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.17710(10)
_cell_length_b                   10.8938(2)
_cell_length_c                   19.8901(3)
_cell_measurement_reflns_used    8670
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.41
_cell_measurement_theta_min      2.77
_cell_volume                     1771.80(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17247
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.625
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.625
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+1.1291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                3896
_reflns_number_total             4083
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            np400922x_si_002.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '178-180 oC' was changed to
'452.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1513364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
C2 C 0.62043(15) 0.37059(11) 0.24010(6) 0.0135(2) Uani 1 1 d .
C3 C 0.96975(17) 0.75521(12) 0.13785(7) 0.0179(3) Uani 1 1 d .
H3A H 1.0054 0.7790 0.0932 0.021 Uiso 1 1 calc R
H3B H 1.0510 0.7828 0.1700 0.021 Uiso 1 1 calc R
C5 C 1.02893(15) 0.54854(11) 0.18560(6) 0.0136(2) Uani 1 1 d .
C6 C 0.96628(15) 0.42325(11) 0.17310(6) 0.0140(2) Uani 1 1 d .
H6 H 1.0005 0.3530 0.1957 0.017 Uiso 1 1 calc R
C7 C 0.85332(15) 0.42591(11) 0.12463(6) 0.0110(2) Uani 1 1 d .
C8 C 0.76682(14) 0.31622(11) 0.09879(6) 0.0117(2) Uani 1 1 d .
C9 C 0.77380(16) 0.28386(12) 0.03071(6) 0.0149(2) Uani 1 1 d .
H9 H 0.8228 0.3367 0.0000 0.018 Uiso 1 1 calc R
C10 C 0.70806(17) 0.17353(13) 0.00888(7) 0.0177(3) Uani 1 1 d .
H10 H 0.7146 0.1524 -0.0363 0.021 Uiso 1 1 calc R
C11 C 0.63263(17) 0.09438(12) 0.05387(7) 0.0183(3) Uani 1 1 d .
H11 H 0.5905 0.0199 0.0389 0.022 Uiso 1 1 calc R
C12 C 0.62023(16) 0.12660(12) 0.12123(7) 0.0167(3) Uani 1 1 d .
H12 H 0.5675 0.0746 0.1513 0.020 Uiso 1 1 calc R
C13 C 0.68694(15) 0.23689(11) 0.14361(6) 0.0126(2) Uani 1 1 d .
C14 C 0.80489(18) 0.81357(12) 0.15349(7) 0.0203(3) Uani 1 1 d .
H14A H 0.8105 0.9015 0.1461 0.024 Uiso 1 1 calc R
H14B H 0.7769 0.7995 0.2002 0.024 Uiso 1 1 calc R
C15 C 0.67436(16) 0.75740(12) 0.10808(7) 0.0164(3) Uani 1 1 d .
H15A H 0.6999 0.7779 0.0618 0.020 Uiso 1 1 calc R
H15B H 0.5698 0.7946 0.1188 0.020 Uiso 1 1 calc R
C16 C 0.51897(15) 0.45518(11) 0.19665(6) 0.0137(2) Uani 1 1 d .
H16A H 0.4125 0.4657 0.2173 0.016 Uiso 1 1 calc R
H16B H 0.5024 0.4167 0.1532 0.016 Uiso 1 1 calc R
C17 C 0.59694(15) 0.58366(12) 0.18569(6) 0.0133(2) Uani 1 1 d .
H17A H 0.5173 0.6451 0.1989 0.016 Uiso 1 1 calc R
H17B H 0.6892 0.5912 0.2161 0.016 Uiso 1 1 calc R
C18 C 0.35813(17) 0.61796(14) 0.07150(7) 0.0206(3) Uani 1 1 d .
H18A H 0.3208 0.5889 0.1144 0.031 Uiso 1 1 calc R
H18B H 0.2885 0.5864 0.0367 0.031 Uiso 1 1 calc R
H18C H 0.3551 0.7060 0.0709 0.031 Uiso 1 1 calc R
C19 C 0.53360(16) 0.57428(12) 0.05961(6) 0.0147(2) Uani 1 1 d .
H19A H 0.5701 0.6048 0.0163 0.018 Uiso 1 1 calc R
H19B H 0.5339 0.4853 0.0575 0.018 Uiso 1 1 calc R
C20 C 0.65706(15) 0.61554(11) 0.11393(6) 0.0111(2) Uani 1 1 d .
C21 C 0.83025(14) 0.55881(11) 0.10033(6) 0.0115(2) Uani 1 1 d .
C22 C 0.1173(2) 0.08022(17) 0.11410(8) 0.0329(4) Uani 1 1 d .
H22A H 0.0628 0.0465 0.1527 0.049 Uiso 1 1 calc R
H22B H 0.0375 0.1042 0.0812 0.049 Uiso 1 1 calc R
H22C H 0.1800 0.1507 0.1274 0.049 Uiso 1 1 calc R
H1 H 0.731(2) 0.2152(17) 0.2389(9) 0.024(5) Uiso 1 1 d .
N1 N 0.67713(13) 0.26493(10) 0.21352(5) 0.0136(2) Uani 1 1 d .
N4 N 0.95203(13) 0.62249(10) 0.14162(5) 0.0137(2) Uani 1 1 d .
O2 O 0.64358(13) 0.39431(9) 0.30003(5) 0.0215(2) Uani 1 1 d .
O5 O 1.13132(12) 0.57896(9) 0.22790(5) 0.0196(2) Uani 1 1 d .
O21 O 0.88141(11) 0.57559(9) 0.03283(4) 0.01551(19) Uani 1 1 d .
H21 H 0.8100 0.5506 0.0073 0.023 Uiso 1 1 calc R
O22 O 0.22263(14) -0.00910(11) 0.08616(5) 0.0261(2) Uani 1 1 d .
H22 H 0.2717 -0.0445 0.1164 0.039 Uiso 1 1 calc R
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
O2 C2 N1 120.29(12)
O2 C2 C16 120.58(12)
N1 C2 C16 119.01(11)
N4 C3 C14 108.44(11)
O5 C5 N4 126.90(12)
O5 C5 C6 126.75(12)
N4 C5 C6 106.35(10)
C7 C6 C5 109.94(11)
C6 C7 C8 124.30(11)
C6 C7 C21 109.40(10)
C8 C7 C21 126.30(10)
C9 C8 C13 118.58(11)
C9 C8 C7 121.29(11)
C13 C8 C7 119.92(11)
C10 C9 C8 120.35(12)
C9 C10 C11 120.61(12)
C10 C11 C12 119.84(12)
C11 C12 C13 119.87(12)
C12 C13 C8 120.70(12)
C12 C13 N1 118.34(11)
C8 C13 N1 120.93(11)
C3 C14 C15 109.32(11)
C14 C15 C20 114.68(10)
C2 C16 C17 113.85(10)
C20 C17 C16 117.49(10)
C18 C19 C20 114.46(10)
C19 C20 C17 111.82(10)
C19 C20 C15 107.21(10)
C17 C20 C15 108.68(10)
C19 C20 C21 110.77(9)
C17 C20 C21 110.92(9)
C15 C20 C21 107.23(10)
O21 C21 N4 105.61(9)
O21 C21 C7 112.50(9)
N4 C21 C7 100.73(9)
O21 C21 C20 112.26(9)
N4 C21 C20 109.30(9)
C7 C21 C20 115.30(10)
C2 N1 C13 125.76(11)
C5 N4 C3 125.60(11)
C5 N4 C21 113.49(10)
C3 N4 C21 120.61(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O2 1.2343(16)
C2 N1 1.3489(17)
C2 C16 1.5113(17)
C3 N4 1.4550(16)
C3 C14 1.523(2)
C5 O5 1.2323(16)
C5 N4 1.3453(17)
C5 C6 1.4788(17)
C6 C7 1.3355(17)
C7 C8 1.4807(17)
C7 C21 1.5380(16)
C8 C9 1.4003(17)
C8 C13 1.4031(17)
C9 C10 1.3864(19)
C10 C11 1.387(2)
C11 C12 1.3887(19)
C12 C13 1.3926(18)
C13 N1 1.4258(16)
C14 C15 1.5262(19)
C15 C20 1.5562(16)
C16 C17 1.5534(17)
C17 C20 1.5490(16)
C18 C19 1.5300(18)
C19 C20 1.5455(17)
C20 C21 1.5686(16)
C21 O21 1.4181(14)
C21 N4 1.4653(15)
C22 O22 1.413(2)
