#------------------------------------------------------------------------------
#$Date: 2016-08-05 06:41:41 +0300 (Fri, 05 Aug 2016) $
#$Revision: 184983 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/35/1543570.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_1543570
loop_
_publ_author_name
'Kaga, Atsushi'
'Tnay, Ya Lin'
'Chiba, Shunsuke'
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_section_title
;
 Synthesis of Fasicularin.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3506
_journal_page_last               3508
_journal_paper_doi               10.1021/acs.orglett.6b01669
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C19 H31 N O'
_chemical_formula_weight         289.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.685(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3417(9)
_cell_length_b                   19.5128(15)
_cell_length_c                   9.2588(11)
_cell_measurement_reflns_used    3335
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      28.9185
_cell_measurement_theta_min      2.4636
_cell_volume                     1663.7(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24015
_diffrn_reflns_theta_full        29.26
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.419
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0698P)²+0.1396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                3216
_reflns_number_total             4527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol6b01669_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 1543570--1543571.cif.'
_cod_database_code               1543570
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.46694(14) 0.72290(6) 0.31550(14) 0.0146(3) Uani d . . 1
H H1 0.3805 0.7441 0.2532 0.018 Uiso calc U R 1
C C2 0.41162(17) 0.69136(7) 0.44944(16) 0.0207(3) Uani d . . 1
H H2A 0.4845 0.6973 0.5394 0.025 Uiso calc U R 1
H H2B 0.3197 0.7134 0.4643 0.025 Uiso calc U R 1
C C3 0.38749(15) 0.61477(7) 0.41268(15) 0.0169(3) Uani d . . 1
H H3A 0.291 0.5995 0.4308 0.02 Uiso calc U R 1
H H3B 0.4633 0.5863 0.4718 0.02 Uiso calc U R 1
C C4 0.39744(14) 0.61028(6) 0.24833(14) 0.0132(3) Uani d . . 1
C C5 0.25170(14) 0.63200(6) 0.15474(16) 0.0168(3) Uani d . . 1
H H5A 0.2222 0.6768 0.1903 0.02 Uiso calc U R 1
H H5B 0.2658 0.638 0.0519 0.02 Uiso calc U R 1
C C6 0.12935(15) 0.58009(7) 0.15915(17) 0.0207(3) Uani d . . 1
H H6A 0.1043 0.5793 0.2589 0.025 Uiso calc U R 1
H H6B 0.042 0.5948 0.0902 0.025 Uiso calc U R 1
C C7 0.17197(15) 0.50809(7) 0.11853(17) 0.0206(3) Uani d . . 1
H H7A 0.1795 0.5068 0.0132 0.025 Uiso calc U R 1
H H7B 0.0956 0.4753 0.1352 0.025 Uiso calc U R 1
C C8 0.31674(15) 0.48665(7) 0.20939(17) 0.0196(3) Uani d . . 1
H H8A 0.345 0.4411 0.1765 0.023 Uiso calc U R 1
H H8B 0.3063 0.4829 0.3137 0.023 Uiso calc U R 1
C C9 0.43546(14) 0.53903(6) 0.19353(15) 0.0154(3) Uani d . . 1
H H9 0.4359 0.5439 0.0861 0.018 Uiso calc U R 1
C C10 0.58657(15) 0.51558(7) 0.26162(17) 0.0191(3) Uani d . . 1
H H10A 0.6084 0.4708 0.2199 0.023 Uiso calc U R 1
H H10B 0.5928 0.5101 0.3688 0.023 Uiso calc U R 1
C C11 0.69471(15) 0.56909(7) 0.22934(16) 0.0184(3) Uani d . . 1
H H11A 0.6914 0.5721 0.1221 0.022 Uiso calc U R 1
H H11B 0.7939 0.5547 0.2743 0.022 Uiso calc U R 1
C C12 0.66257(14) 0.63984(6) 0.28862(15) 0.0150(3) Uani d . . 1
H H12 0.6758 0.6379 0.398 0.018 Uiso calc U R 1
C C13 0.76856(14) 0.68811(7) 0.24454(15) 0.0168(3) Uani d . . 1
C C14 0.85462(15) 0.72385(7) 0.19973(15) 0.0178(3) Uani d . . 1
C C15 0.95323(15) 0.77321(7) 0.14841(16) 0.0191(3) Uani d . . 1
H H15A 0.8995 0.7993 0.0647 0.023 Uiso calc U R 1
H H15B 1.0326 0.748 0.1131 0.023 Uiso calc U R 1
C C16 1.01865(18) 0.82336(8) 0.26813(17) 0.0269(3) Uani d . . 1
H H16A 0.939 0.8479 0.3046 0.032 Uiso calc U R 1
H H16B 1.0736 0.7972 0.3511 0.032 Uiso calc U R 1
C C17 1.11953(18) 0.87576(8) 0.21561(18) 0.0286(4) Uani d . . 1
H H17A 1.1616 0.905 0.2994 0.034 Uiso calc U R 1
H H17B 1.2005 0.8512 0.1817 0.034 Uiso calc U R 1
C C18 1.04513(17) 0.92113(8) 0.09268(18) 0.0260(3) Uani d . . 1
H H18A 1.0151 0.8934 0.0046 0.039 Uiso calc U R 1
H H18B 1.1126 0.9568 0.0719 0.039 Uiso calc U R 1
H H18C 0.9596 0.9425 0.122 0.039 Uiso calc U R 1
C C19 0.57540(15) 0.78096(6) 0.35938(15) 0.0168(3) Uani d . . 1
H H19A 0.6571 0.7645 0.4334 0.02 Uiso calc U R 1
H H19B 0.6149 0.7972 0.2727 0.02 Uiso calc U R 1
N N1 0.51117(11) 0.66347(5) 0.22944(12) 0.0128(2) Uani d . . 1
O O1 0.50134(11) 0.83536(5) 0.41843(11) 0.0208(2) Uani d . . 1
H H1A 0.5067 0.8296 0.5091 0.031 Uiso calc U R 1
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
N1 C1 C19 118.91(11)
N1 C1 C2 106.04(10)
C19 C1 C2 112.16(11)
C3 C2 C1 105.35(11)
C2 C3 C4 104.01(10)
N1 C4 C9 112.00(10)
N1 C4 C3 103.57(10)
C9 C4 C3 115.55(10)
N1 C4 C5 108.42(10)
C9 C4 C5 107.03(10)
C3 C4 C5 110.12(11)
C6 C5 C4 113.23(11)
C7 C6 C5 112.06(11)
C6 C7 C8 111.14(12)
C7 C8 C9 110.65(11)
C10 C9 C8 113.37(11)
C10 C9 C4 112.65(11)
C8 C9 C4 111.05(11)
C9 C10 C11 108.34(11)
C10 C11 C12 111.83(11)
C13 C12 N1 109.78(10)
C13 C12 C11 107.17(11)
N1 C12 C11 112.03(11)
C14 C13 C12 174.85(14)
C13 C14 C15 174.80(14)
C14 C15 C16 112.48(12)
C17 C16 C15 113.06(13)
C18 C17 C16 113.66(13)
O1 C19 C1 108.12(11)
C12 N1 C1 111.69(10)
C12 N1 C4 112.53(9)
C1 N1 C4 101.92(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.5037(16)
C1 C19 1.5285(18)
C1 C2 1.5489(19)
C2 C3 1.5409(19)
C3 C4 1.5426(18)
C4 N1 1.5163(16)
C4 C9 1.5417(17)
C4 C5 1.5451(18)
C5 C6 1.5329(19)
C6 C7 1.5245(19)
C7 C8 1.5261(19)
C8 C9 1.5333(18)
C9 C10 1.5165(18)
C10 C11 1.5171(19)
C11 C12 1.5339(18)
C12 C13 1.4732(18)
C12 N1 1.5008(16)
C13 C14 1.1904(19)
C14 C15 1.4659(19)
C15 C16 1.527(2)
C16 C17 1.525(2)
C17 C18 1.515(2)
C19 O1 1.4254(15)
