#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150673.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_7150673
loop_
_publ_author_name
'Yang, Sung-Hyun'
'Clark, G. R.'
'Caprio, Vittorio'
_publ_section_title
;
 A concise approach to the core structures of pinnaic acid and
 halichlorine
;
_journal_issue                   14
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2981
_journal_page_last               2990
_journal_paper_doi               10.1039/b903904j
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C18 H27 N O3'
_chemical_formula_sum            'C18 H27 N O3'
_chemical_formula_weight         305.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.454(1)
_cell_angle_beta                 101.796(1)
_cell_angle_gamma                97.250(1)
_cell_formula_units_Z            2
_cell_length_a                   6.2552(1)
_cell_length_b                   10.5282(2)
_cell_length_c                   13.4329(2)
_cell_measurement_reflns_used    4948
_cell_measurement_temperature    84(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.03
_cell_volume                     823.76(2)
_computing_cell_refinement       'SAINT (Bruker, 1995)'
_computing_data_collection       'SMART (Bruker, 1995)'
_computing_data_reduction        'SAINT (Bruker, 1995)'
_computing_molecular_graphics    'Ortep-III (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      84(1)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'Area detector 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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7744
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.30
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0559
_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)+(0.0976P)²+0.1252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                2529
_reflns_number_total             3258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b903904j.txt
_cod_data_source_block           yshr99
_cod_original_sg_symbol_Hall     -p_1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150673
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2952(2) 0.84613(13) 0.87510(10) 0.0239(3) Uani 1 1 d . . .
HO1 H -0.2585 0.9240 0.9118 0.054(8) Uiso 1 1 calc R . .
O2 O -0.1495(2) 0.61750(12) 0.89416(10) 0.0221(3) Uani 1 1 d . . .
HO2 H -0.2218 0.6738 0.9153 0.063(9) Uiso 1 1 calc R . .
O3 O 0.1924(2) 0.88216(12) 1.03140(10) 0.0232(3) Uani 1 1 d . . .
HO3 H 0.1135 0.8480 0.9713 0.028(6) Uiso 1 1 calc R . .
N N 0.0189(2) 0.67575(14) 0.84817(11) 0.0167(3) Uani 1 1 d . . .
C1 C -0.2895(3) 0.69639(17) 0.70235(14) 0.0192(4) Uani 1 1 d . . .
H1A H -0.4200 0.6375 0.7063 0.023 Uiso 1 1 calc R . .
C2 C -0.3060(3) 0.69682(19) 0.58541(14) 0.0245(4) Uani 1 1 d . . .
H2A H -0.4040 0.6168 0.5371 0.029 Uiso 1 1 calc R . .
H2B H -0.3636 0.7740 0.5723 0.029 Uiso 1 1 calc R . .
C3 C -0.0663(3) 0.70193(19) 0.56958(14) 0.0249(4) Uani 1 1 d . . .
H3A H -0.0599 0.6246 0.5139 0.030 Uiso 1 1 calc R . .
H3B H -0.0186 0.7818 0.5503 0.030 Uiso 1 1 calc R . .
C4 C 0.0835(3) 0.70285(18) 0.67685(14) 0.0197(4) Uani 1 1 d . . .
H4A H 0.1507 0.7934 0.7194 0.024 Uiso 1 1 calc R . .
H4B H 0.2003 0.6524 0.6660 0.024 Uiso 1 1 calc R . .
C5 C -0.0767(3) 0.63624(16) 0.73089(13) 0.0172(4) Uani 1 1 d . . .
C7 C 0.2201(3) 0.61758(17) 0.87775(13) 0.0190(4) Uani 1 1 d . . .
H7A H 0.3328 0.6534 0.8458 0.023 Uiso 1 1 calc R . .
C8 C 0.1776(3) 0.46435(18) 0.83407(14) 0.0238(4) Uani 1 1 d . . .
H8A H 0.3168 0.4331 0.8491 0.029 Uiso 1 1 calc R . .
H8B H 0.0778 0.4250 0.8694 0.029 Uiso 1 1 calc R . .
C9 C 0.0752(3) 0.41899(17) 0.71367(14) 0.0222(4) Uani 1 1 d . . .
H9A H 0.0317 0.3225 0.6900 0.027 Uiso 1 1 calc R . .
H9B H 0.1854 0.4444 0.6774 0.027 Uiso 1 1 calc R . .
C10 C -0.1294(3) 0.48219(17) 0.68494(14) 0.0201(4) Uani 1 1 d . . .
H10A H -0.2479 0.4457 0.7122 0.024 Uiso 1 1 calc R . .
H10B H -0.1812 0.4592 0.6084 0.024 Uiso 1 1 calc R . .
C11 C 0.4884(3) 0.85268(16) 1.16516(14) 0.0187(4) Uani 1 1 d . . .
C12 C 0.3600(3) 0.83530(18) 1.23625(14) 0.0228(4) Uani 1 1 d . . .
H12A H 0.2079 0.8028 1.2111 0.027 Uiso 1 1 calc R . .
C13 C 0.4583(3) 0.86632(18) 1.34502(15) 0.0248(4) Uani 1 1 d . . .
H13A H 0.3716 0.8545 1.3917 0.030 Uiso 1 1 calc R . .
C14 C 0.6869(3) 0.91502(18) 1.38324(14) 0.0240(4) Uani 1 1 d . . .
H14A H 0.7523 0.9367 1.4555 0.029 Uiso 1 1 calc R . .
C15 C 0.8159(3) 0.93097(18) 1.31287(15) 0.0249(4) Uani 1 1 d . . .
H15A H 0.9682 0.9625 1.3381 0.030 Uiso 1 1 calc R . .
C16 C 0.7181(3) 0.89992(17) 1.20441(15) 0.0221(4) Uani 1 1 d . . .
H16A H 0.8059 0.9106 1.1579 0.027 Uiso 1 1 calc R . .
C1' C -0.2803(3) 0.83918(17) 0.76879(14) 0.0209(4) Uani 1 1 d . . .
H1'A H -0.1421 0.8945 0.7711 0.025 Uiso 1 1 calc R . .
H1'B H -0.4016 0.8748 0.7348 0.025 Uiso 1 1 calc R . .
C2' C 0.3156(3) 0.66442(17) 0.99861(13) 0.0208(4) Uani 1 1 d . . .
H2'A H 0.2057 0.6311 1.0320 0.025 Uiso 1 1 calc R . .
H2'B H 0.4452 0.6247 1.0156 0.025 Uiso 1 1 calc R . .
C3' C 0.3827(3) 0.81656(17) 1.04663(14) 0.0200(4) Uani 1 1 d . . .
H3'A H 0.4913 0.8507 1.0118 0.024 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1' O1 HO1 109.5 . . ?
N O2 HO2 109.5 . . ?
C3' O3 HO3 109.5 . . ?
O2 N C7 106.06(12) . . ?
O2 N C5 106.68(12) . . ?
C7 N C5 112.36(13) . . ?
C1' C1 C2 108.50(14) . . ?
C1' C1 C5 115.49(14) . . ?
C2 C1 C5 103.43(14) . . ?
C1' C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
C5 C1 H1A 109.7 . . ?
C3 C2 C1 106.30(14) . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 106.23(15) . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
C2 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
C3 C4 C5 104.29(14) . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
N C5 C4 110.02(13) . . ?
N C5 C10 110.74(13) . . ?
C4 C5 C10 111.88(14) . . ?
N C5 C1 111.25(13) . . ?
C4 C5 C1 102.18(13) . . ?
C10 C5 C1 110.50(13) . . ?
N C7 C2' 110.28(14) . . ?
N C7 C8 113.00(14) . . ?
C2' C7 C8 111.88(14) . . ?
N C7 H7A 107.1 . . ?
C2' C7 H7A 107.1 . . ?
C8 C7 H7A 107.1 . . ?
C9 C8 C7 111.21(14) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 111.08(14) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 C5 112.01(14) . . ?
C9 C10 H10A 109.2 . . ?
C5 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C5 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C16 118.85(16) . . ?
C12 C11 C3' 120.72(16) . . ?
C16 C11 C3' 120.39(16) . . ?
C11 C12 C13 120.60(17) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 119.96(18) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C15 C14 C13 119.73(17) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.37(18) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 120.48(18) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
O1 C1' C1 112.60(14) . . ?
O1 C1' H1'A 109.1 . . ?
C1 C1' H1'A 109.1 . . ?
O1 C1' H1'B 109.1 . . ?
C1 C1' H1'B 109.1 . . ?
H1'A C1' H1'B 107.8 . . ?
C3' C2' C7 114.88(14) . . ?
C3' C2' H2'A 108.5 . . ?
C7 C2' H2'A 108.5 . . ?
C3' C2' H2'B 108.5 . . ?
C7 C2' H2'B 108.5 . . ?
H2'A C2' H2'B 107.5 . . ?
O3 C3' C11 108.16(13) . . ?
O3 C3' C2' 111.62(14) . . ?
C11 C3' C2' 110.98(14) . . ?
O3 C3' H3'A 108.7 . . ?
C11 C3' H3'A 108.7 . . ?
C2' C3' H3'A 108.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1' 1.434(2) . ?
O1 HO1 0.8200 . ?
O2 N 1.4695(18) . ?
O2 HO2 0.8200 . ?
O3 C3' 1.454(2) . ?
O3 HO3 0.8200 . ?
N C7 1.493(2) . ?
N C5 1.496(2) . ?
C1 C1' 1.532(2) . ?
C1 C2 1.554(2) . ?
C1 C5 1.564(2) . ?
C1 H1A 0.9800 . ?
C2 C3 1.553(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.547(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.548(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.550(2) . ?
C7 C2' 1.538(2) . ?
C7 C8 1.540(2) . ?
C7 H7A 0.9800 . ?
C8 C9 1.539(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.540(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.398(3) . ?
C11 C16 1.403(3) . ?
C11 C3' 1.523(2) . ?
C12 C13 1.401(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.398(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.389(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.397(3) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C1' H1'A 0.9700 . ?
C1' H1'B 0.9700 . ?
C2' C3' 1.537(2) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C3' H3'A 0.9800 . ?
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
O1 HO1 O3 0.82 1.95 2.7543(18) 167.0 2_577
O2 HO2 O1 0.82 2.10 2.7307(18) 134.1 .
O3 HO3 N 0.82 2.05 2.7570(19) 144.0 .
