#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:02:56 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178970 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/99/4119958.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_4119958
loop_
_publ_author_name
'Robert-André F. Rarig'
'Mai N. Tran'
'David M. Chenoweth'
_publ_section_title
;
 Synthesis and Conformational Dynamics of the Reported Structure of
 Xylopyridine A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9213
_journal_page_last               9219
_journal_paper_doi               10.1021/ja404737q
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C24 H14 N2 O2'
_chemical_formula_weight         362.37
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      88
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.5111(12)
_cell_length_b                   18.5111(12)
_cell_length_c                   9.7964(7)
_cell_measurement_temperature    143(1)
_cell_volume                     3356.8(4)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0097
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35582
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0308
_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)+(0.0357P)²+2.3086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                1525
_reflns_number_total             1722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja404737q_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'I 41/a '
_cod_database_code               4119958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
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 0.25521(6) 0.21707(6) 0.27858(11) 0.0252(2) Uani 1 1 d . . .
C2 C 0.20292(6) 0.18030(6) 0.36948(11) 0.0258(2) Uani 1 1 d . . .
C3 C 0.16435(6) 0.21124(6) 0.47741(12) 0.0284(3) Uani 1 1 d . A .
C4 C 0.11544(6) 0.16983(6) 0.54929(13) 0.0328(3) Uani 1 1 d . . .
N5 N 0.10169(6) 0.09987(6) 0.52099(12) 0.0363(3) Uani 0.840(15) 1 d P A 1
C5' C 0.10169(6) 0.09987(6) 0.52099(12) 0.0363(3) Uani 0.160(15) 1 d P A 2
C6 C 0.14097(7) 0.06887(6) 0.42202(13) 0.0342(3) Uani 1 1 d . . .
C7 C 0.19301(6) 0.10653(6) 0.34909(11) 0.0272(2) Uani 1 1 d . A .
O8 O 0.23429(5) 0.06838(4) 0.25692(8) 0.0309(2) Uani 1 1 d . . .
C9 C 0.30286(6) 0.09583(6) 0.23454(11) 0.0282(3) Uani 1 1 d . A .
C10 C 0.35578(8) 0.04732(7) 0.19449(12) 0.0361(3) Uani 1 1 d . . .
C11 C 0.42538(8) 0.07090(7) 0.17625(13) 0.0421(4) Uani 0.840(15) 1 d P A 1
N11' N 0.42538(8) 0.07090(7) 0.17625(13) 0.0421(4) Uani 0.160(15) 1 d P A 2
C12 C 0.44286(7) 0.14248(7) 0.20296(13) 0.0380(3) Uani 1 1 d . . .
C13 C 0.38978(6) 0.19098(7) 0.24091(12) 0.0314(3) Uani 1 1 d . A .
C14 C 0.31754(6) 0.16918(6) 0.25082(11) 0.0263(2) Uani 1 1 d . . .
H3 H 0.1714(7) 0.2616(7) 0.5009(14) 0.032(3) Uiso 1 1 d . . .
H4 H 0.0889(7) 0.1910(7) 0.6256(15) 0.039(4) Uiso 1 1 d . . .
H5' H 0.066(5) 0.074(5) 0.562(10) 0.040 Uiso 0.160(15) 1 d P A 2
H6 H 0.1328(7) 0.0185(8) 0.4027(15) 0.039(4) Uiso 1 1 d . . .
H10 H 0.3428(8) -0.0030(8) 0.1807(15) 0.042(4) Uiso 1 1 d . . .
H11 H 0.4620(10) 0.0373(9) 0.1465(18) 0.041(5) Uiso 0.840(15) 1 d P A 1
H12 H 0.4931(8) 0.1591(8) 0.1942(15) 0.042(4) Uiso 1 1 d . . .
H13 H 0.4027(7) 0.2417(7) 0.2589(14) 0.034(3) 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
_geom_angle_site_symmetry_1
C1 C1 C14 125.02(13) 13
C1 C1 C2 124.67(13) 13
C14 C1 C2 110.15(9) .
C7 C2 C3 116.28(10) .
C7 C2 C1 116.79(10) .
C3 C2 C1 126.88(10) .
C4 C3 C2 119.57(10) .
C4 C3 H3 120.2(8) .
C2 C3 H3 120.3(8) .
N5 C4 C3 123.54(11) .
N5 C4 H4 116.6(8) .
C3 C4 H4 119.8(8) .
C6 N5 C4 117.22(11) .
C6 N5 H5' 120(6) .
C4 N5 H5' 123(6) .
N5 C6 C7 122.27(11) .
N5 C6 H6 118.1(9) .
C7 C6 H6 119.6(9) .
O8 C7 C6 117.73(10) .
O8 C7 C2 121.57(10) .
C6 C7 C2 120.70(11) .
C7 O8 C9 115.10(8) .
O8 C9 C10 117.07(10) .
O8 C9 C14 121.20(10) .
C10 C9 C14 121.73(11) .
C11 C10 C9 119.65(12) .
C11 C10 H10 121.3(8) .
C9 C10 H10 119.0(9) .
C10 C11 C12 119.85(12) .
C10 C11 H11 119.6(10) .
C12 C11 H11 120.5(10) .
C13 C12 C11 120.33(12) .
C13 C12 H12 119.5(8) .
C11 C12 H12 120.1(8) .
C12 C13 C14 120.68(11) .
C12 C13 H13 119.7(8) .
C14 C13 H13 119.6(8) .
C9 C14 C13 117.32(10) .
C9 C14 C1 116.91(10) .
C13 C14 C1 125.76(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.355(2) 13
C1 C14 1.4802(15) .
C1 C2 1.4810(15) .
C2 C7 1.3923(15) .
C2 C3 1.3985(16) .
C3 C4 1.3795(16) .
C3 H3 0.969(13) .
C4 N5 1.3485(16) .
C4 H4 0.977(14) .
N5 C6 1.3408(17) .
N5 H5' 0.91(11) .
C6 C7 1.3872(16) .
C6 H6 0.964(14) .
C7 O8 1.3777(14) .
O8 C9 1.3847(14) .
C9 C10 1.3856(16) .
C9 C14 1.3938(15) .
C10 C11 1.372(2) .
C10 H10 0.972(15) .
C11 C12 1.3888(19) .
C11 H11 0.966(19) .
C12 C13 1.3818(17) .
C12 H12 0.983(14) .
C13 C14 1.4003(16) .
C13 H13 0.984(14) .
