#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/73/4027347.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_4027347
loop_
_publ_author_name
'Christian Brückner'
'Junichi Ogikubo'
'Jason R. McCarthy'
'Joshua Akhigbe'
'Michael A. Hyland'
'Pedro Daddario'
'Jill L. Worlinsky'
'Matthias Zeller'
'James T. Engle'
'Christopher J. Ziegler'
'Matthew J. Ranaghan'
'Megan N. Sandberg'
'Robert R. Birge'
_publ_section_title
;
 meso-Arylporpholactones and their Reduction Products
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6480
_journal_page_last               6494
_journal_paper_doi               10.1021/jo300963m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C44 H32 N4 O2, 0.5(H2 O)'
_chemical_formula_sum            'C44 H33 N4 O2.5'
_chemical_formula_weight         657.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           87
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4'
_symmetry_space_group_name_H-M   'I 4/m'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.460(3)
_cell_length_b                   13.460(3)
_cell_length_c                   9.7678(18)
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.58
_cell_volume                     1769.6(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'
_computing_structure_refinement
;  
SHELXLE Rev548, Shelxle (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7481
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; [Sheldrick, G. M. (2004)]'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             702
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1046
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0531
_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)+(0.0901P)²+0.8333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1651
_reflns_number_gt                832
_reflns_number_total             1046
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo300963m_si_005.cif
_cod_data_source_block           omeoxazole
_cod_original_formula_sum        'C44 H33 N4 O2.50'
_cod_database_code               4027347
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'-y+1/2, x+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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.62754(16) 0.31151(16) 0.0000 0.0452(5) Uani 1 2 d S . .
C2 C 0.6211(11) 0.2009(7) 0.0000 0.0522(17) Uani 0.75 2 d SP A 1
H2 H 0.6740 0.1542 0.0000 0.063 Uiso 0.75 2 calc SPR A 1
C3 C 0.52192(17) 0.18241(16) 0.0000 0.0516(6) Uani 0.75 2 d SP A 1
H3 H 0.4927 0.1182 0.0000 0.062 Uiso 0.75 2 calc SPR A 1
O3 O 0.5000 0.0000 0.2500 0.075(3) Uani 0.25 4 d SPD B 1
H3C H 0.505(19) -0.059(6) 0.22(2) 0.090 Uiso 0.125 1 d PD C 1
O1 O 0.624(2) 0.2197(17) -0.008(7) 0.0522(17) Uani 0.125 1 d P A -2
C3B C 0.52192(17) 0.18241(16) 0.0000 0.0516(6) Uani 0.25 2 d SP A -2
H3B H 0.5031 0.1359 -0.0755 0.062 Uiso 0.125 1 calc PR A -2
O2 O 0.5143(8) 0.1426(8) 0.1285(14) 0.074(3) Uani 0.125 1 d P A -2
C10 C 0.5678(16) 0.0462(11) 0.154(2) 0.082(5) Uani 0.125 1 d P A -2
H10A H 0.5549 0.0003 0.0784 0.123 Uiso 0.125 1 calc PR A -2
H10B H 0.5438 0.0168 0.2399 0.123 Uiso 0.125 1 calc PR A -2
H10C H 0.6393 0.0587 0.1611 0.123 Uiso 0.125 1 calc PR A -2
C4 C 0.46757(16) 0.27491(15) 0.0000 0.0451(5) Uani 1 2 d S . .
C5 C 0.36455(16) 0.28257(15) 0.0000 0.0450(5) Uani 1 2 d S A .
C6 C 0.30523(15) 0.18801(16) 0.0000 0.0477(6) Uani 1 2 d S . .
C7 C 0.27867(17) 0.14271(15) 0.1201(2) 0.0734(7) Uani 1 1 d . A .
H7 H 0.2976 0.1717 0.2048 0.088 Uiso 1 1 calc R . .
C8 C 0.22428(17) 0.05458(16) 0.1196(3) 0.0805(7) Uani 1 1 d . . .
H8 H 0.2055 0.0248 0.2039 0.097 Uiso 1 1 calc R A .
C9 C 0.19806(18) 0.01101(18) 0.0000 0.0649(8) Uani 1 2 d S . .
H9 H 0.1617 -0.0495 0.0000 0.078 Uiso 1 2 calc SR . .
N1 N 0.53454(12) 0.35147(13) 0.0000 0.0438(5) Uani 1 2 d S A .
H1 H 0.5201 0.4152 0.0000 0.053 Uiso 0.50 2 calc SPR . .
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
O1 C1 N1 110.7(15) 11 .
O1 C1 N1 110.7(15) . .
O1 C1 C5 123.0(15) 11 2_655
O1 C1 C5 123.0(15) . 2_655
N1 C1 C5 126.21(19) . 2_655
N1 C1 C2 109.9(6) . .
C5 C1 C2 123.9(6) 2_655 .
C3 C2 C1 103.9(8) . .
C3 C2 H2 128.0 . .
C1 C2 H2 128.0 . .
C2 C3 C4 109.9(4) . .
C2 C3 H3 125.1 . .
C4 C3 H3 125.1 . .
O2 C10 H10A 109.5 . .
O2 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
O2 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C4 C5 126.93(19) . .
N1 C4 C3 108.38(18) . .
C5 C4 C3 124.69(19) . .
C4 C5 C1 124.79(19) . 10_565
C4 C5 C6 117.85(19) . .
C1 C5 C6 117.36(19) 10_565 .
C7 C6 C7 117.9(2) . 11
C7 C6 C5 121.06(11) . .
C7 C6 C5 121.06(11) 11 .
C6 C7 C8 120.9(2) . .
C6 C7 H7 119.6 . .
C8 C7 H7 119.6 . .
C9 C8 C7 120.6(2) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C8 C9 C8 119.3(2) 11 .
C8 C9 H9 120.4 11 .
C8 C9 H9 120.4 . .
C1 N1 C4 107.93(17) . .
C1 N1 H1 126.0 . .
C4 N1 H1 126.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.24(2) 11
C1 O1 1.24(2) .
C1 N1 1.362(3) .
C1 C5 1.405(3) 2_655
C1 C2 1.491(9) .
C2 C3 1.358(15) .
C2 H2 0.9500 .
C3 C4 1.444(3) .
C3 H3 0.9500 .
O3 H3C 0.84(2) .
O2 C10 1.505(18) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C4 N1 1.369(3) .
C4 C5 1.390(3) .
C5 C1 1.405(3) 10_565
C5 C6 1.503(3) .
C6 C7 1.369(2) .
C6 C7 1.369(2) 11
C7 C8 1.394(3) .
C7 H7 0.9500 .
C8 C9 1.354(3) .
C8 H8 0.9500 .
C9 C8 1.354(3) 11
C9 H9 0.9500 .
N1 H1 0.8800 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 0.0 . .
C5 C1 C2 C3 180.0 2_655 .
C1 C2 C3 C4 0.0 . .
C2 C3 C4 N1 0.0 . .
C2 C3 C4 C5 180.0 . .
N1 C4 C5 C1 0.0 . 10_565
C3 C4 C5 C1 180.0 . 10_565
N1 C4 C5 C6 180.0 . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 C7 89.0(2) . .
C1 C5 C6 C7 -91.0(2) 10_565 .
C4 C5 C6 C7 -89.0(2) . 11
C1 C5 C6 C7 91.0(2) 10_565 11
C7 C6 C7 C8 -1.5(4) 11 .
C5 C6 C7 C8 -179.5(2) . .
C6 C7 C8 C9 1.2(4) . .
C7 C8 C9 C8 -0.7(4) . 11
O1 C1 N1 C4 -4(3) 11 .
O1 C1 N1 C4 4(3) . .
C5 C1 N1 C4 180.0 2_655 .
C2 C1 N1 C4 0.0 . .
C5 C4 N1 C1 180.0 . .
C3 C4 N1 C1 0.0 . .
