#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/38/4123864.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_4123864
loop_
_publ_author_name
'Mfuh, Adelphe M.'
'Zhang, Yu'
'Stephens, David E.'
'Vo, Anh X. T.'
'Arman, Hadi D.'
'Larionov, Oleg V.'
_publ_section_title
;
 Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an
 Efficient Construction of the 1,2-Oxazadecaline Core.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8050
_journal_page_last               8053
_journal_paper_doi               10.1021/jacs.5b05205
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C11 H11 N O4'
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.316(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7284(13)
_cell_length_b                   7.9180(12)
_cell_length_c                   14.286(2)
_cell_measurement_reflns_used    4030
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.6
_cell_volume                     985.7(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6673
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.48
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1105
_reflns_number_gt                2062
_reflns_number_total             2243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b05205_si_011.cif
_cod_data_source_block           cd1279a
_cod_depositor_comments
'Adding full bibliography for 4123862--4123864.cif.'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4123864
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.97483(9) 0.45787(10) 0.15361(6) 0.0146(2) Uani 1 1 d
C2 C 1.00382(13) 0.15405(15) 0.13489(8) 0.0144(2) Uani 1 1 d
C3 C 0.89705(14) 0.15555(14) 0.06181(8) 0.0145(2) Uani 1 1 d
C9 C 0.86820(13) 0.45940(14) 0.07839(8) 0.0132(2) Uani 1 1 d
C8 C 0.80409(13) 0.61524(14) 0.05467(8) 0.0143(2) Uani 1 1 d
C7 C 0.69869(13) 0.62600(15) -0.02273(8) 0.0161(3) Uani 1 1 d
O4 O 0.84695(10) 0.75672(10) 0.10585(6) 0.0173(2) Uani 1 1 d
O2 O 1.14660(10) 0.32405(11) 0.24542(6) 0.0189(2) Uani 1 1 d
C4 C 0.82821(13) 0.31138(14) 0.02987(8) 0.0135(2) Uani 1 1 d
C6 C 0.65799(14) 0.48003(16) -0.07338(8) 0.0169(3) Uani 1 1 d
C5 C 0.72138(14) 0.32565(15) -0.04687(8) 0.0159(3) Uani 1 1 d
N1 N 1.07139(13) 0.01263(13) 0.17479(8) 0.0190(2) Uani 1 1 d
O3 O 0.64447(11) 0.78455(11) -0.04235(7) 0.0217(2) Uani 1 1 d
C1 C 1.04928(13) 0.31307(14) 0.18160(8) 0.0140(2) Uani 1 1 d
C10 C 0.54184(16) 0.80294(18) -0.12397(10) 0.0245(3) Uani 1 1 d
C11 C 0.74061(16) 0.79579(17) 0.17556(10) 0.0238(3) Uani 1 1 d
H6A H 0.589(2) 0.490(2) -0.1277(12) 0.029 Uiso 1 1 d
H3A H 0.867(2) 0.051(2) 0.0309(12) 0.029 Uiso 1 1 d
H1A H 1.055(2) -0.079(2) 0.1445(12) 0.029 Uiso 1 1 d
H5A H 0.690(2) 0.224(2) -0.0805(13) 0.029 Uiso 1 1 d
H10A H 0.448(2) 0.739(2) -0.1145(13) 0.036 Uiso 1 1 d
H1B H 1.156(2) 0.026(2) 0.2076(12) 0.029 Uiso 1 1 d
H10B H 0.522(2) 0.927(2) -0.1254(12) 0.036 Uiso 1 1 d
H10C H 0.593(2) 0.766(2) -0.1800(14) 0.036 Uiso 1 1 d
H11A H 0.773(2) 0.896(2) 0.2053(13) 0.036 Uiso 1 1 d
H11B H 0.738(2) 0.704(2) 0.2206(13) 0.036 Uiso 1 1 d
H11C H 0.638(2) 0.814(2) 0.1455(13) 0.036 Uiso 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
C1 O1 C9 121.53(9)
C3 C2 N1 125.79(11)
C3 C2 C1 119.79(10)
N1 C2 C1 114.33(10)
C2 C3 C4 120.51(10)
C2 C3 H3A 119.9(10)
C4 C3 H3A 119.6(10)
O1 C9 C8 116.22(10)
O1 C9 C4 121.15(10)
C8 C9 C4 122.64(11)
O4 C8 C9 119.99(10)
O4 C8 C7 121.05(10)
C9 C8 C7 118.95(10)
O3 C7 C6 125.39(11)
O3 C7 C8 114.99(10)
C6 C7 C8 119.61(10)
C8 O4 C11 112.16(9)
C9 C4 C5 117.16(10)
C9 C4 C3 118.42(10)
C5 C4 C3 124.41(10)
C5 C6 C7 120.15(11)
C5 C6 H6A 121.3(11)
C7 C6 H6A 118.5(11)
C6 C5 C4 121.45(11)
C6 C5 H5A 120.2(11)
C4 C5 H5A 118.3(11)
C2 N1 H1A 115.5(12)
C2 N1 H1B 117.7(12)
H1A N1 H1B 119.4(16)
C7 O3 C10 116.91(10)
O2 C1 O1 117.41(10)
O2 C1 C2 124.20(11)
O1 C1 C2 118.36(10)
O3 C10 H10A 108.8(11)
O3 C10 H10B 102.4(11)
H10A C10 H10B 111.8(15)
O3 C10 H10C 109.9(11)
H10A C10 H10C 112.5(15)
H10B C10 H10C 111.0(15)
O4 C11 H11A 107.7(12)
O4 C11 H11B 110.0(11)
H11A C11 H11B 110.5(16)
O4 C11 H11C 109.8(11)
H11A C11 H11C 108.9(15)
H11B C11 H11C 109.8(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3663(14)
O1 C9 1.3804(13)
C2 C3 1.3587(16)
C2 N1 1.3739(15)
C2 C1 1.4688(15)
C3 C4 1.4353(16)
C3 H3A 0.964(18)
C9 C8 1.3887(15)
C9 C4 1.3957(15)
C8 O4 1.3775(13)
C8 C7 1.3995(16)
C7 O3 1.3649(14)
C7 C6 1.3986(17)
O4 C11 1.4339(15)
O2 C1 1.2128(14)
C4 C5 1.4021(16)
C6 C5 1.3855(16)
C6 H6A 0.960(18)
C5 H5A 0.970(18)
N1 H1A 0.853(19)
N1 H1B 0.856(19)
O3 C10 1.4361(15)
C10 H10A 0.980(19)
C10 H10B 0.996(19)
C10 H10C 0.98(2)
C11 H11A 0.938(19)
C11 H11B 0.970(19)
C11 H11C 0.98(2)
