#------------------------------------------------------------------------------
#$Date: 2016-03-22 14:06:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178985 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/08/4120845.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_4120845
loop_
_publ_author_name
'Yuan Shi'
'Jeremy T. Wilmot'
'Lars Ulrik Nordstrøm'
'Derek S. Tan'
'David Y. Gin'
_publ_section_title
;
 Total Synthesis, Relay Synthesis, and Structural Confirmation of the
 C18-Norditerpenoid Alkaloid Neofinaconitine
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14313
_journal_page_last               14320
_journal_paper_doi               10.1021/ja4064958
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_sum            'C30 H42 N2 O6'
_chemical_formula_weight         526.66
_chemical_name_systematic
; 
 ? 
;
_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                 110.243(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8743(14)
_cell_length_b                   14.678(2)
_cell_length_c                   11.0685(18)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      31.55
_cell_measurement_theta_min      2.40
_cell_volume                     1352.7(4)
_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      170(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22432
_diffrn_reflns_theta_full        31.55
_diffrn_reflns_theta_max         31.55
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_correction_T_min  0.9483
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         8868
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0701P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1264
_reflns_number_gt                7337
_reflns_number_total             8868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4064958_si_005.cif
_cod_data_source_block           yus10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'UNK' changed to 'unk'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4120845
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
N1 N 0.62170(18) 0.99311(12) 0.32157(15) 0.0391(3) Uani 1 1 d .
H1A H 0.6829 1.0188 0.2834 0.047 Uiso 1 1 calc R
H1B H 0.5745 1.0268 0.3638 0.047 Uiso 1 1 calc R
N2 N 0.28925(14) 0.91862(10) 0.79181(11) 0.0275(2) Uani 1 1 d .
O1 O 0.30508(12) 0.85825(8) 0.47042(10) 0.0278(2) Uani 1 1 d .
O2 O 0.44274(15) 0.98809(9) 0.47382(12) 0.0381(3) Uani 1 1 d .
O3 O -0.10837(16) 0.56226(9) 0.83102(14) 0.0419(3) Uani 1 1 d .
O4 O -0.06320(14) 0.72585(10) 1.07399(11) 0.0398(3) Uani 1 1 d .
O5 O 0.19287(16) 0.59139(9) 0.81955(13) 0.0384(3) Uani 1 1 d .
H5 H 0.129(3) 0.555(2) 0.832(3) 0.058(7) Uiso 1 1 d .
O6 O -0.06765(13) 0.98048(9) 0.74557(11) 0.0342(2) Uani 1 1 d .
C1 C 0.4998(3) 1.0176(2) 0.9348(2) 0.0716(9) Uani 1 1 d .
H1C H 0.5725 1.0234 1.0243 0.107 Uiso 1 1 calc R
H1D H 0.4176 1.0653 0.9161 0.107 Uiso 1 1 calc R
H1E H 0.5612 1.0242 0.8768 0.107 Uiso 1 1 calc R
C2 C 0.0420(2) 0.77142(18) 1.18345(17) 0.0481(5) Uani 1 1 d .
H2A H 0.0168 0.7538 1.2597 0.072 Uiso 1 1 calc R
H2B H 0.0287 0.8374 1.1707 0.072 Uiso 1 1 calc R
H2C H 0.1532 0.7546 1.1956 0.072 Uiso 1 1 calc R
C3 C -0.1939(3) 1.04513(15) 0.7181(2) 0.0486(5) Uani 1 1 d .
H3A H -0.1984 1.0701 0.7988 0.073 Uiso 1 1 calc R
H3B H -0.2962 1.0154 0.6706 0.073 Uiso 1 1 calc R
H3C H -0.1743 1.0945 0.6658 0.073 Uiso 1 1 calc R
C4 C 0.5699(2) 0.71020(16) 0.3044(2) 0.0500(5) Uani 1 1 d .
H4A H 0.5629 0.6456 0.3027 0.060 Uiso 1 1 calc R
C5 C 0.6617(2) 0.75542(18) 0.2426(2) 0.0525(5) Uani 1 1 d .
H5B H 0.7149 0.7211 0.1966 0.063 Uiso 1 1 calc R
C6 C -0.2048(2) 0.52770(15) 0.9004(2) 0.0468(5) Uani 1 1 d .
H6A H -0.1689 0.4661 0.9313 0.070 Uiso 1 1 calc R
H6B H -0.3174 0.5258 0.8435 0.070 Uiso 1 1 calc R
H6C H -0.1942 0.5675 0.9740 0.070 Uiso 1 1 calc R
C7 C 0.6761(2) 0.84816(16) 0.24729(18) 0.0430(4) Uani 1 1 d .
H7A H 0.7385 0.8772 0.2039 0.052 Uiso 1 1 calc R
C8 C 0.0394(2) 1.01482(12) 0.57883(18) 0.0365(4) Uani 1 1 d .
H8A H -0.0378 1.0626 0.5326 0.044 Uiso 1 1 calc R
H8B H 0.1234 1.0442 0.6520 0.044 Uiso 1 1 calc R
C9 C -0.16538(19) 0.64518(12) 0.76506(15) 0.0317(3) Uani 1 1 d .
H9A H -0.2685 0.6339 0.6926 0.038 Uiso 1 1 calc R
C10 C 0.4902(2) 0.76098(13) 0.36758(17) 0.0368(4) Uani 1 1 d .
H10A H 0.4255 0.7308 0.4080 0.044 Uiso 1 1 calc R
C11 C 0.35110(17) 0.91874(12) 0.68547(13) 0.0289(3) Uani 1 1 d .
H11A H 0.4396 0.8739 0.7041 0.035 Uiso 1 1 calc R
H11B H 0.3961 0.9797 0.6799 0.035 Uiso 1 1 calc R
C12 C 0.41998(19) 0.92503(16) 0.91529(15) 0.0407(4) Uani 1 1 d .
H12A H 0.5009 0.8775 0.9197 0.049 Uiso 1 1 calc R
H12B H 0.3774 0.9134 0.9856 0.049 Uiso 1 1 calc R
C13 C -0.18436(17) 0.72756(12) 0.84343(15) 0.0296(3) Uani 1 1 d .
H13A H -0.2798 0.7201 0.8710 0.036 Uiso 1 1 calc R
C14 C -0.04822(17) 0.94453(11) 0.63111(14) 0.0278(3) Uani 1 1 d .
H14A H -0.1576 0.9357 0.5654 0.033 Uiso 1 1 calc R
C15 C 0.1168(2) 0.97475(13) 0.48850(16) 0.0352(4) Uani 1 1 d .
H15A H 0.1819 1.0218 0.4652 0.042 Uiso 1 1 calc R
H15B H 0.0328 0.9535 0.4085 0.042 Uiso 1 1 calc R
C16 C -0.03317(17) 0.74975(13) 0.95907(14) 0.0314(3) Uani 1 1 d .
H16A H -0.0132 0.8168 0.9601 0.038 Uiso 1 1 calc R
C17 C -0.21425(17) 0.80204(12) 0.74043(15) 0.0311(3) Uani 1 1 d .
H17A H -0.1885 0.8629 0.7810 0.037 Uiso 1 1 calc R
H17B H -0.3279 0.8017 0.6827 0.037 Uiso 1 1 calc R
C18 C 0.11786(18) 0.69949(13) 0.95489(14) 0.0326(3) Uani 1 1 d .
H18A H 0.1253 0.6403 0.9995 0.039 Uiso 1 1 calc R
H18B H 0.2134 0.7357 1.0044 0.039 Uiso 1 1 calc R
C19 C 0.50188(17) 0.85596(12) 0.37385(14) 0.0294(3) Uani 1 1 d .
C20 C 0.12557(17) 0.68107(11) 0.81917(14) 0.0275(3) Uani 1 1 d .
C21 C 0.22289(17) 0.89551(10) 0.55453(13) 0.0252(3) Uani 1 1 d .
C22 C 0.41671(17) 0.90881(12) 0.44376(14) 0.0285(3) Uani 1 1 d .
C23 C 0.60004(18) 0.90172(13) 0.31522(14) 0.0315(3) Uani 1 1 d .
C24 C -0.03990(16) 0.68210(11) 0.71170(14) 0.0268(3) Uani 1 1 d .
H24A H -0.0373 0.6435 0.6380 0.032 Uiso 1 1 calc R
C25 C 0.22617(17) 0.73728(11) 0.64376(14) 0.0267(3) Uani 1 1 d .
H25A H 0.3341 0.7412 0.6365 0.032 Uiso 1 1 calc R
H25B H 0.1773 0.6780 0.6084 0.032 Uiso 1 1 calc R
C26 C 0.23688(16) 0.74800(11) 0.78567(13) 0.0260(3) Uani 1 1 d .
H26A H 0.3501 0.7409 0.8457 0.031 Uiso 1 1 calc R
C27 C 0.11895(16) 0.81713(11) 0.57171(13) 0.0234(3) Uani 1 1 d .
H27A H 0.0403 0.7969 0.4871 0.028 Uiso 1 1 calc R
C28 C 0.17609(15) 0.84598(11) 0.79027(12) 0.0236(3) Uani 1 1 d .
H28A H 0.1391 0.8528 0.8655 0.028 Uiso 1 1 calc R
C29 C -0.10040(16) 0.77882(11) 0.66321(13) 0.0249(3) Uani 1 1 d .
H29A H -0.1712 0.7719 0.5711 0.030 Uiso 1 1 calc R
C30 C 0.03154(15) 0.84978(10) 0.66456(12) 0.0223(2) 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 0.0000 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
C12 N2 C11 110.88(11)
C12 N2 C28 112.26(13)
C11 N2 C28 116.10(12)
C22 O1 C21 119.71(12)
C9 O3 C6 114.12(14)
C2 O4 C16 112.00(14)
C3 O6 C14 112.54(14)
C10 C4 C5 118.8(2)
C7 C5 C4 121.07(18)
C5 C7 C23 121.34(17)
C15 C8 C14 113.32(15)
O3 C9 C24 108.96(13)
O3 C9 C13 118.38(13)
C24 C9 C13 100.17(12)
C4 C10 C19 121.58(16)
N2 C11 C21 113.39(11)
N2 C12 C1 111.93(18)
C9 C13 C17 99.57(12)
C9 C13 C16 113.84(13)
C17 C13 C16 110.17(14)
O6 C14 C8 108.61(14)
O6 C14 C30 107.69(12)
C8 C14 C30 116.70(12)
C8 C15 C21 109.13(12)
O4 C16 C13 108.14(12)
O4 C16 C18 109.87(13)
C13 C16 C18 113.01(13)
C13 C17 C29 105.74(12)
C16 C18 C20 116.22(12)
C10 C19 C23 119.68(14)
C10 C19 C22 120.51(14)
C23 C19 C22 119.79(15)
O5 C20 C26 106.58(11)
O5 C20 C24 107.13(13)
C26 C20 C24 109.32(11)
O5 C20 C18 108.22(12)
C26 C20 C18 111.84(13)
C24 C20 C18 113.41(11)
O1 C21 C15 109.95(11)
O1 C21 C27 104.57(11)
C15 C21 C27 109.69(12)
O1 C21 C11 108.13(11)
C15 C21 C11 114.68(14)
C27 C21 C11 109.33(11)
O2 C22 O1 123.60(14)
O2 C22 C19 124.48(14)
O1 C22 C19 111.93(14)
N1 C23 C7 119.64(15)
N1 C23 C19 122.88(15)
C7 C23 C19 117.48(16)
C9 C24 C20 109.03(12)
C9 C24 C29 104.34(11)
C20 C24 C29 113.68(12)
C27 C25 C26 104.90(11)
C20 C26 C28 109.19(10)
C20 C26 C25 111.29(12)
C28 C26 C25 103.22(11)
C21 C27 C25 110.18(11)
C21 C27 C30 108.04(11)
C25 C27 C30 104.50(10)
N2 C28 C30 109.88(11)
N2 C28 C26 115.71(11)
C30 C28 C26 101.32(11)
C24 C29 C30 116.06(11)
C24 C29 C17 102.82(11)
C30 C29 C17 118.10(12)
C28 C30 C14 114.84(12)
C28 C30 C27 97.81(10)
C14 C30 C27 114.13(11)
C28 C30 C29 111.92(11)
C14 C30 C29 108.52(11)
C27 C30 C29 109.28(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C23 1.353(2)
N2 C12 1.4579(18)
N2 C11 1.4607(17)
N2 C28 1.4608(19)
O1 C22 1.3497(17)
O1 C21 1.4723(17)
O2 C22 1.210(2)
O3 C9 1.419(2)
O3 C6 1.426(2)
O4 C2 1.416(2)
O4 C16 1.4306(17)
O5 C20 1.4449(19)
O6 C3 1.419(2)
O6 C14 1.4368(18)
C1 C12 1.513(3)
C4 C10 1.374(3)
C4 C5 1.400(3)
C5 C7 1.367(3)
C7 C23 1.411(2)
C8 C15 1.514(2)
C8 C14 1.521(2)
C9 C24 1.529(2)
C9 C13 1.531(2)
C10 C19 1.398(3)
C11 C21 1.540(2)
C13 C17 1.535(2)
C13 C16 1.535(2)
C14 C30 1.546(2)
C15 C21 1.516(2)
C16 C18 1.545(2)
C17 C29 1.5701(19)
C18 C20 1.551(2)
C19 C23 1.422(2)
C19 C22 1.475(2)
C20 C26 1.527(2)
C20 C24 1.537(2)
C21 C27 1.527(2)
C24 C29 1.547(2)
C25 C27 1.546(2)
C25 C26 1.5484(19)
C26 C28 1.543(2)
C27 C30 1.5618(18)
C28 C30 1.5328(18)
C29 C30 1.5632(19)
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
O5 H5 O3 0.82(3) 2.11(3) 2.7532(18) 136(3) .
N1 H1B O2 0.88 2.04 2.6869(18) 129.6 .
N1 H1A O5 0.88 2.13 3.0012(18) 173.1 2_656
