#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/31/7103191.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_7103191
loop_
_publ_author_name
'Fürstner, Alois'
'Ackerstaff, Jens'
_publ_section_title
;
 Formal total synthesis of (-)-haouamine A.
;
_journal_issue                   25
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2870
_journal_page_last               2872
_journal_paper_doi               10.1039/b805295f
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_compound_source        toluene/pentane
_chemical_formula_moiety         'C21 H21 N O4'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.11170(10)
_cell_length_b                   9.8304(2)
_cell_length_c                   34.9917(8)
_cell_measurement_reflns_used    34557
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.79
_cell_measurement_theta_min      4.67
_cell_volume                     1758.33(6)
_computing_cell_refinement       'PROTEUM2 (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            34417
_diffrn_reflns_theta_full        68.79
_diffrn_reflns_theta_max         68.79
_diffrn_reflns_theta_min         4.67
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack, Otwinowski (1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0337
_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)+(0.0187P)²+0.7075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                3189
_reflns_number_total             3215
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b805295f.txt
_cod_data_source_block           5370
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (29
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (21
time).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (41
time).

'_geom_angle_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (46 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7103191
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.7016(3) -0.36144(14) -0.10889(4) 0.0259(3) Uani 1 1 d . . .
C2 C -0.7197(3) -0.30847(18) -0.06999(4) 0.0274(4) Uani 1 1 d . . .
H2A H -0.6647 -0.2119 -0.0697 0.033 Uiso 1 1 calc R . .
H2B H -0.6001 -0.3601 -0.0531 0.033 Uiso 1 1 calc R . .
C3 C -0.9983(3) -0.32011(16) -0.05499(4) 0.0255(3) Uani 1 1 d . . .
H3 H -1.1182 -0.2597 -0.0699 0.031 Uiso 1 1 calc R . .
O3 O -0.9862(2) -0.27691(13) -0.01582(3) 0.0309(3) Uani 1 1 d . . .
H3A H -1.1370 -0.2562 -0.0082 0.046 Uiso 1 1 calc R . .
C4 C -1.0868(3) -0.46617(17) -0.05772(4) 0.0260(3) Uani 1 1 d . . .
H4 H -1.2038 -0.5024 -0.0392 0.031 Uiso 1 1 calc R . .
C4A C -1.0004(3) -0.54405(16) -0.08610(4) 0.0234(3) Uani 1 1 d . . .
C4B C -1.0200(3) -0.69112(16) -0.09295(4) 0.0243(3) Uani 1 1 d . . .
C5 C -1.1870(3) -0.78919(17) -0.07702(4) 0.0249(3) Uani 1 1 d . . .
O5 O -1.3649(2) -0.74318(11) -0.05083(3) 0.0285(3) Uani 1 1 d . . .
C5' C -1.5261(4) -0.84323(18) -0.03266(5) 0.0342(4) Uani 1 1 d . . .
H5'1 H -1.4151 -0.9113 -0.0202 0.051 Uiso 1 1 calc R . .
H5'2 H -1.6364 -0.8877 -0.0519 0.051 Uiso 1 1 calc R . .
H5'3 H -1.6372 -0.7991 -0.0135 0.051 Uiso 1 1 calc R . .
C6 C -1.1681(4) -0.92356(17) -0.08915(5) 0.0281(4) Uani 1 1 d . . .
H6 H -1.2854 -0.9903 -0.0795 0.034 Uiso 1 1 calc R . .
C7 C -0.9756(4) -0.95970(17) -0.11554(5) 0.0308(4) Uani 1 1 d . . .
H7 H -0.9629 -1.0518 -0.1236 0.037 Uiso 1 1 calc R . .
C8 C -0.8027(4) -0.86493(18) -0.13035(5) 0.0299(4) Uani 1 1 d . . .
H8 H -0.6699 -0.8916 -0.1478 0.036 Uiso 1 1 calc R . .
C8A C -0.8279(3) -0.73041(17) -0.11915(4) 0.0273(4) Uani 1 1 d . . .
C9 C -0.6645(3) -0.60970(16) -0.13084(5) 0.0274(4) Uani 1 1 d . . .
H9A H -0.6319 -0.6096 -0.1587 0.033 Uiso 1 1 calc R . .
H9B H -0.4948 -0.6087 -0.1172 0.033 Uiso 1 1 calc R . .
C9A C -0.8363(3) -0.48834(16) -0.11893(4) 0.0246(3) Uani 1 1 d . . .
H9A1 H -0.9575 -0.4680 -0.1406 0.030 Uiso 1 1 calc R . .
C10 C -0.5501(3) -0.29420(16) -0.13452(4) 0.0257(3) Uani 1 1 d . . .
O10 O -0.4236(2) -0.19191(12) -0.12784(3) 0.0345(3) Uani 1 1 d . . .
O11 O -0.5595(2) -0.35611(12) -0.16923(3) 0.0299(3) Uani 1 1 d . . .
C12 C -0.4178(4) -0.29022(19) -0.20024(5) 0.0337(4) Uani 1 1 d . . .
H12A H -0.3178 -0.3590 -0.2148 0.040 Uiso 1 1 calc R . .
H12B H -0.2923 -0.2235 -0.1896 0.040 Uiso 1 1 calc R . .
C13 C -0.6068(3) -0.21933(17) -0.22621(5) 0.0290(4) Uani 1 1 d . . .
C14 C -0.7690(4) -0.11835(19) -0.21191(5) 0.0370(4) Uani 1 1 d . . .
H14 H -0.7547 -0.0930 -0.1858 0.044 Uiso 1 1 calc R . .
C15 C -0.9510(4) -0.0539(2) -0.23481(7) 0.0499(5) Uani 1 1 d . . .
H15 H -1.0612 0.0144 -0.2243 0.060 Uiso 1 1 calc R . .
C16 C -0.9729(5) -0.0880(3) -0.27250(7) 0.0544(6) Uani 1 1 d . . .
H16 H -1.0985 -0.0438 -0.2882 0.065 Uiso 1 1 calc R . .
C17 C -0.8129(5) -0.1865(3) -0.28772(6) 0.0540(6) Uani 1 1 d . . .
H17 H -0.8280 -0.2098 -0.3140 0.065 Uiso 1 1 calc R . .
C18 C -0.6265(4) -0.2532(2) -0.26467(5) 0.0416(5) Uani 1 1 d . . .
H18 H -0.5154 -0.3207 -0.2753 0.050 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C10 N1 C2 118.59(13) . . y
C10 N1 C9A 121.58(13) . . y
C2 N1 C9A 119.77(13) . . y
N1 C2 C3 110.72(13) . . y
N1 C2 H2A 109.5 . . n
C3 C2 H2A 109.5 . . n
N1 C2 H2B 109.5 . . n
C3 C2 H2B 109.5 . . n
H2A C2 H2B 108.1 . . n
O3 C3 C4 110.78(13) . . y
O3 C3 C2 105.44(12) . . y
C4 C3 C2 109.29(13) . . y
O3 C3 H3 110.4 . . n
C4 C3 H3 110.4 . . n
C2 C3 H3 110.4 . . n
C3 O3 H3A 109.5 . . n
C4A C4 C3 119.72(15) . . y
C4A C4 H4 120.1 . . n
C3 C4 H4 120.1 . . n
C4 C4A C4B 131.76(15) . . y
C4 C4A C9A 122.62(14) . . y
C4B C4A C9A 105.55(13) . . y
C8A C4B C5 119.87(15) . . y
C8A C4B C4A 109.34(14) . . y
C5 C4B C4A 130.75(15) . . y
O5 C5 C6 124.39(15) . . y
O5 C5 C4B 116.31(14) . . y
C6 C5 C4B 119.27(15) . . y
C5 O5 C5' 116.92(13) . . y
O5 C5' H5'1 109.5 . . n
O5 C5' H5'2 109.5 . . n
H5'1 C5' H5'2 109.5 . . n
O5 C5' H5'3 109.5 . . n
H5'1 C5' H5'3 109.5 . . n
H5'2 C5' H5'3 109.5 . . n
C5 C6 C7 119.53(16) . . y
C5 C6 H6 120.2 . . n
C7 C6 H6 120.2 . . n
C8 C7 C6 121.77(16) . . y
C8 C7 H7 119.1 . . n
C6 C7 H7 119.1 . . n
C7 C8 C8A 118.48(16) . . y
C7 C8 H8 120.8 . . n
C8A C8 H8 120.8 . . n
C8 C8A C4B 120.98(16) . . y
C8 C8A C9 128.53(16) . . y
C4B C8A C9 110.47(14) . . y
C8A C9 C9A 102.74(13) . . y
C8A C9 H9A 111.2 . . n
C9A C9 H9A 111.2 . . n
C8A C9 H9B 111.2 . . n
C9A C9 H9B 111.2 . . n
H9A C9 H9B 109.1 . . n
N1 C9A C4A 112.53(12) . . y
N1 C9A C9 117.14(14) . . y
C4A C9A C9 103.87(12) . . y
N1 C9A H9A1 107.6 . . n
C4A C9A H9A1 107.6 . . n
C9 C9A H9A1 107.6 . . n
O10 C10 N1 125.34(15) . . y
O10 C10 O11 124.04(14) . . y
N1 C10 O11 110.62(13) . . y
C10 O11 C12 116.67(13) . . y
O11 C12 C13 109.75(14) . . y
O11 C12 H12A 109.7 . . n
C13 C12 H12A 109.7 . . n
O11 C12 H12B 109.7 . . n
C13 C12 H12B 109.7 . . n
H12A C12 H12B 108.2 . . n
C14 C13 C18 118.49(17) . . y
C14 C13 C12 119.98(15) . . y
C18 C13 C12 121.53(17) . . y
C15 C14 C13 121.44(19) . . y
C15 C14 H14 119.3 . . n
C13 C14 H14 119.3 . . n
C16 C15 C14 120.2(2) . . y
C16 C15 H15 119.9 . . n
C14 C15 H15 119.9 . . n
C15 C16 C17 119.9(2) . . y
C15 C16 H16 120.0 . . n
C17 C16 H16 120.0 . . n
C16 C17 C18 120.50(19) . . y
C16 C17 H17 119.7 . . n
C18 C17 H17 119.7 . . n
C13 C18 C17 119.5(2) . . y
C13 C18 H18 120.3 . . n
C17 C18 H18 120.3 . . n
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
N1 C10 1.357(2) . y
N1 C2 1.4605(19) . y
N1 C9A 1.468(2) . y
C2 C3 1.522(2) . y
C2 H2A 0.9900 . n
C2 H2B 0.9900 . n
C3 O3 1.4363(18) . y
C3 C4 1.508(2) . y
C3 H3 1.0000 . n
O3 H3A 0.8400 . n
C4 C4A 1.330(2) . y
C4 H4 0.9500 . n
C4A C4B 1.469(2) . y
C4A C9A 1.524(2) . y
C4B C8A 1.398(2) . y
C4B C5 1.403(2) . y
C5 O5 1.3677(19) . y
C5 C6 1.391(2) . y
O5 C5' 1.432(2) . y
C5' H5'1 0.9800 . n
C5' H5'2 0.9800 . n
C5' H5'3 0.9800 . n
C6 C7 1.395(2) . y
C6 H6 0.9500 . n
C7 C8 1.385(2) . y
C7 H7 0.9500 . n
C8 C8A 1.385(2) . y
C8 H8 0.9500 . n
C8A C9 1.508(2) . y
C9 C9A 1.539(2) . y
C9 H9A 0.9900 . n
C9 H9B 0.9900 . n
C9A H9A1 1.0000 . n
C10 O10 1.218(2) . y
C10 O11 1.3596(19) . y
O11 C12 1.4565(19) . y
C12 C13 1.498(2) . y
C12 H12A 0.9900 . n
C12 H12B 0.9900 . n
C13 C14 1.387(3) . y
C13 C18 1.390(2) . y
C14 C15 1.382(3) . y
C14 H14 0.9500 . n
C15 C16 1.365(3) . y
C15 H15 0.9500 . n
C16 C17 1.375(3) . y
C16 H16 0.9500 . n
C17 C18 1.410(3) . y
C17 H17 0.9500 . n
C18 H18 0.9500 . n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653041
