#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:36:02 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178955 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/84/4118430.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_4118430
loop_
_publ_author_name
'Hui Ming Ge'
'Lan-De Zhang'
'Ren Xiang Tan'
'Zhu-Jun Yao'
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email       seikweng@um.edu.my
_publ_contact_author_fax         '03 7967 4193'
_publ_contact_author_phone       '03 7967 6778'
_publ_section_title
;
 Protecting Group-Free Total Synthesis of (-)-Lannotinidine B
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12323
_journal_page_last               12325
_journal_paper_doi               10.1021/ja305261h
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C17 H27 N O 3'
_chemical_formula_sum            'C17 H27 N O3'
_chemical_formula_weight         293.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-01-01

2012-05-30 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.126(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1958(7)
_cell_length_b                   13.9189(11)
_cell_length_c                   12.6004(10)
_cell_measurement_reflns_used    3040
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3302
_cell_measurement_theta_min      2.7126
_cell_volume                     1564.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 software (Bruker, 2011)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5154
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.71
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details '1075 Friedel pairs were merged'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0341
_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)+(0.0622P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                1684
_reflns_number_total             1790
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja305261h_si_002.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4118430
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
O1 O 0.50009(17) 0.08466(12) 0.50007(13) 0.0521(4) Uani 1 1 d .
O2 O 1.0870(2) 0.02610(18) 0.61424(17) 0.0718(6) Uani 1 1 d .
O3 O 0.99075(18) 0.00454(13) 0.43641(14) 0.0538(4) Uani 1 1 d .
N1 N 0.57041(17) 0.23026(13) 0.80463(12) 0.0390(4) Uani 1 1 d .
C1 C 0.5283(3) 0.14101(17) 0.85056(18) 0.0486(5) Uani 1 1 d .
H1A H 0.4366 0.1523 0.8737 0.058 Uiso 1 1 calc R
H1B H 0.6060 0.1250 0.9153 0.058 Uiso 1 1 calc R
C2 C 0.5043(3) 0.05498(16) 0.77412(18) 0.0476(5) Uani 1 1 d .
H2A H 0.4127 0.0639 0.7174 0.057 Uiso 1 1 calc R
H2B H 0.4928 -0.0025 0.8149 0.057 Uiso 1 1 calc R
C3 C 0.6357(2) 0.04177(14) 0.72141(17) 0.0406(4) Uani 1 1 d .
H3A H 0.6130 -0.0098 0.6682 0.049 Uiso 1 1 calc R
H3B H 0.7243 0.0237 0.7771 0.049 Uiso 1 1 calc R
C4 C 0.66829(19) 0.13504(12) 0.66406(14) 0.0304(3) Uani 1 1 d .
C5 C 0.5335(2) 0.14946(14) 0.56563(15) 0.0354(4) Uani 1 1 d .
C6 C 0.4369(3) 0.23866(17) 0.54866(17) 0.0463(5) Uani 1 1 d .
H6A H 0.3653 0.2341 0.4782 0.056 Uiso 1 1 calc R
H6B H 0.5001 0.2940 0.5464 0.056 Uiso 1 1 calc R
C7 C 0.3509(2) 0.25534(18) 0.63716(18) 0.0469(5) Uani 1 1 d .
H7A H 0.2724 0.3021 0.6101 0.056 Uiso 1 1 calc R
H7B H 0.3028 0.1956 0.6490 0.056 Uiso 1 1 calc R
C8 C 0.4460(2) 0.29043(16) 0.74703(19) 0.0453(5) Uani 1 1 d .
H8A H 0.4867 0.3528 0.7353 0.054 Uiso 1 1 calc R
H8B H 0.3798 0.3002 0.7953 0.054 Uiso 1 1 calc R
C9 C 0.69531(19) 0.21507(13) 0.75315(14) 0.0325(4) Uani 1 1 d .
H9 H 0.7763 0.1898 0.8122 0.039 Uiso 1 1 calc R
C10 C 0.7565(2) 0.30961(13) 0.72128(18) 0.0395(4) Uani 1 1 d .
H10A H 0.7807 0.3514 0.7848 0.047 Uiso 1 1 calc R
H10B H 0.6792 0.3409 0.6658 0.047 Uiso 1 1 calc R
C11 C 0.8962(2) 0.29657(14) 0.67739(18) 0.0424(5) Uani 1 1 d .
H11 H 0.9146 0.3575 0.6440 0.051 Uiso 1 1 calc R
C12 C 0.8656(2) 0.22039(14) 0.58721(17) 0.0394(4) Uani 1 1 d .
H12A H 0.7875 0.2433 0.5261 0.047 Uiso 1 1 calc R
H12B H 0.9557 0.2107 0.5614 0.047 Uiso 1 1 calc R
C13 C 0.8173(2) 0.12477(12) 0.62652(15) 0.0334(4) Uani 1 1 d .
H13 H 0.8948 0.1077 0.6922 0.040 Uiso 1 1 calc R
C14 C 1.0353(2) 0.2736(2) 0.7680(2) 0.0539(6) Uani 1 1 d .
H14A H 1.0596 0.3277 0.8163 0.081 Uiso 1 1 calc R
H14B H 1.1179 0.2601 0.7362 0.081 Uiso 1 1 calc R
H14C H 1.0159 0.2186 0.8084 0.081 Uiso 1 1 calc R
C15 C 0.8209(2) 0.04614(15) 0.54225(18) 0.0442(5) Uani 1 1 d .
H15A H 0.7754 -0.0120 0.5619 0.053 Uiso 1 1 calc R
H15B H 0.7635 0.0666 0.4707 0.053 Uiso 1 1 calc R
C16 C 0.9806(2) 0.02566(13) 0.53794(18) 0.0426(5) Uani 1 1 d .
C17 C 1.1402(3) -0.0133(2) 0.4228(3) 0.0643(7) Uani 1 1 d .
H17A H 1.2022 0.0418 0.4468 0.096 Uiso 1 1 calc R
H17B H 1.1353 -0.0254 0.3470 0.096 Uiso 1 1 calc R
H17C H 1.1821 -0.0683 0.4655 0.096 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C16 O3 C17 116.17(19)
C8 N1 C1 115.66(17)
C8 N1 C9 117.79(15)
C1 N1 C9 111.39(16)
N1 C1 C2 115.50(16)
N1 C1 H1A 108.4
C2 C1 H1A 108.4
N1 C1 H1B 108.4
C2 C1 H1B 108.4
H1A C1 H1B 107.5
C1 C2 C3 111.29(18)
C1 C2 H2A 109.4
C3 C2 H2A 109.4
C1 C2 H2B 109.4
C3 C2 H2B 109.4
H2A C2 H2B 108.0
C2 C3 C4 111.47(16)
C2 C3 H3A 109.3
C4 C3 H3A 109.3
C2 C3 H3B 109.3
C4 C3 H3B 109.3
H3A C3 H3B 108.0
C5 C4 C3 106.01(14)
C5 C4 C9 116.31(14)
C3 C4 C9 106.13(14)
C5 C4 C13 111.22(14)
C3 C4 C13 110.39(14)
C9 C4 C13 106.64(13)
O1 C5 C6 118.21(18)
O1 C5 C4 118.25(17)
C6 C5 C4 123.49(16)
C5 C6 C7 114.27(16)
C5 C6 H6A 108.7
C7 C6 H6A 108.7
C5 C6 H6B 108.7
C7 C6 H6B 108.7
H6A C6 H6B 107.6
C8 C7 C6 115.15(18)
C8 C7 H7A 108.5
C6 C7 H7A 108.5
C8 C7 H7B 108.5
C6 C7 H7B 108.5
H7A C7 H7B 107.5
N1 C8 C7 118.26(17)
N1 C8 H8A 107.7
C7 C8 H8A 107.7
N1 C8 H8B 107.7
C7 C8 H8B 107.7
H8A C8 H8B 107.1
N1 C9 C10 111.83(15)
N1 C9 C4 114.69(14)
C10 C9 C4 115.60(14)
N1 C9 H9 104.4
C10 C9 H9 104.4
C4 C9 H9 104.4
C9 C10 C11 112.96(15)
C9 C10 H10A 109.0
C11 C10 H10A 109.0
C9 C10 H10B 109.0
C11 C10 H10B 109.0
H10A C10 H10B 107.8
C14 C11 C10 112.29(18)
C14 C11 C12 112.28(18)
C10 C11 C12 109.44(16)
C14 C11 H11 107.5
C10 C11 H11 107.5
C12 C11 H11 107.5
C13 C12 C11 112.30(16)
C13 C12 H12A 109.1
C11 C12 H12A 109.1
C13 C12 H12B 109.1
C11 C12 H12B 109.1
H12A C12 H12B 107.9
C12 C13 C15 109.98(16)
C12 C13 C4 111.43(14)
C15 C13 C4 116.40(15)
C12 C13 H13 106.1
C15 C13 H13 106.1
C4 C13 H13 106.1
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C15 C13 110.23(16)
C16 C15 H15A 109.6
C13 C15 H15A 109.6
C16 C15 H15B 109.6
C13 C15 H15B 109.6
H15A C15 H15B 108.1
O2 C16 O3 122.5(2)
O2 C16 C15 125.7(2)
O3 C16 C15 111.79(18)
O3 C17 H17A 109.5
O3 C17 H17B 109.5
H17A C17 H17B 109.5
O3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.211(2)
O2 C16 1.193(3)
O3 C16 1.338(3)
O3 C17 1.447(3)
N1 C8 1.460(3)
N1 C1 1.462(3)
N1 C9 1.466(2)
C1 C2 1.519(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.526(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.550(2)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.538(2)
C4 C9 1.558(2)
C4 C13 1.562(2)
C5 C6 1.511(3)
C6 C7 1.534(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.526(3)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.523(2)
C9 H9 0.9800
C10 C11 1.528(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C14 1.526(3)
C11 C12 1.529(3)
C11 H11 0.9800
C12 C13 1.524(2)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C15 1.531(2)
C13 H13 0.9800
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 C16 1.510(3)
C15 H15A 0.9700
C15 H15B 0.9700
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
C8 N1 C1 C2 88.3(2)
C9 N1 C1 C2 -49.7(2)
N1 C1 C2 C3 50.0(3)
C1 C2 C3 C4 -53.8(2)
C2 C3 C4 C5 -68.1(2)
C2 C3 C4 C9 56.2(2)
C2 C3 C4 C13 171.36(16)
C3 C4 C5 O1 -55.3(2)
C9 C4 C5 O1 -172.97(17)
C13 C4 C5 O1 64.7(2)
C3 C4 C5 C6 122.25(19)
C9 C4 C5 C6 4.6(2)
C13 C4 C5 C6 -117.74(18)
O1 C5 C6 C7 113.8(2)
C4 C5 C6 C7 -63.7(3)
C5 C6 C7 C8 74.0(3)
C1 N1 C8 C7 -70.4(2)
C9 N1 C8 C7 64.9(2)
C6 C7 C8 N1 -59.3(3)
C8 N1 C9 C10 52.0(2)
C1 N1 C9 C10 -170.90(16)
C8 N1 C9 C4 -82.1(2)
C1 N1 C9 C4 55.0(2)
C5 C4 C9 N1 59.6(2)
C3 C4 C9 N1 -57.95(19)
C13 C4 C9 N1 -175.66(14)
C5 C4 C9 C10 -72.73(19)
C3 C4 C9 C10 169.67(16)
C13 C4 C9 C10 51.97(19)
N1 C9 C10 C11 174.54(16)
C4 C9 C10 C11 -51.8(2)
C9 C10 C11 C14 -74.3(2)
C9 C10 C11 C12 51.1(2)
C14 C11 C12 C13 68.6(2)
C10 C11 C12 C13 -56.8(2)
C11 C12 C13 C15 -167.92(17)
C11 C12 C13 C4 61.5(2)
C5 C4 C13 C12 72.08(19)
C3 C4 C13 C12 -170.54(16)
C9 C4 C13 C12 -55.67(19)
C5 C4 C13 C15 -55.1(2)
C3 C4 C13 C15 62.3(2)
C9 C4 C13 C15 177.12(16)
C12 C13 C15 C16 68.2(2)
C4 C13 C15 C16 -163.92(16)
C17 O3 C16 O2 -3.0(3)
C17 O3 C16 C15 178.1(2)
C13 C15 C16 O2 36.5(3)
C13 C15 C16 O3 -144.61(17)
