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#$Date: 2016-03-21 19:09:12 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178837 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/91/4109105.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_4109105
loop_
_publ_author_name
'Iwao Okamoto'
'Mayumi Nabeta'
'Yasuko Hayakawa'
'Nobuyoshi Morita'
'Tetsuya Takeya'
'Hyuma Masu'
'Isao Azumaya'
'Osamu Tamura'
_publ_contact_author_address
;Showa Pharmaceutical University, 
3-3165 Higashi-Tamagawagakuen, Machida, Tokyo
194-8543, Japan
;
_publ_contact_author_email       iokamoto@ac.shoyaku.ac.jp
_publ_contact_author_fax         +81-42-721-1579
_publ_contact_author_name        'Iwao Okamoto'
_publ_contact_author_phone       +81-42-721-1579
_publ_section_title
;
 Acid-Induced Molecular Folding and Unfolding of N-Methyl Aromatic Amide
 Bearing 2,6-Disubstituted Pyridines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1892
_journal_page_last               1893
_journal_paper_doi               10.1021/ja0682879
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C33 H29 N9 O4'
_chemical_formula_weight         615.65
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_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            4
_cell_length_a                   37.074(2)
_cell_length_b                   9.0221(5)
_cell_length_c                   9.3593(5)
_cell_measurement_reflns_used    1083
_cell_measurement_temperature    120
_cell_measurement_theta_max      20.87
_cell_measurement_theta_min      4.40
_cell_volume                     3130.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker ApexII CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0922
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7600
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.90
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.9911
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3379
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1133
_reflns_number_gt                2126
_reflns_number_total             3379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0682879si20061120_025750.cif
_cod_data_source_block           compound2(a0509121mas)
_cod_database_code               4109105
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -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
O1 O 0.06630(4) 0.2417(2) -0.2503(2) 0.0315(5) Uani 1 1 d .
N2 N 0.09173(6) 0.2782(3) -0.0336(2) 0.0252(6) Uani 1 1 d .
O2 O 0.19753(5) 0.0632(3) 0.3857(2) 0.0436(6) Uani 1 1 d .
N4 N 0.14369(6) 0.1806(3) 0.4074(3) 0.0276(6) Uani 1 1 d .
N1 N 0.0000 0.2297(4) -0.1002(3) 0.0223(8) Uani 1 2 d S
N5 N 0.18039(6) 0.4091(3) 0.2456(3) 0.0329(6) Uani 1 1 d .
N3 N 0.11509(6) 0.2302(3) 0.1925(2) 0.0242(6) Uani 1 1 d .
C6 C 0.08837(7) 0.2933(3) 0.1190(3) 0.0226(7) Uani 1 1 d .
C7 C 0.05987(8) 0.3691(4) 0.1792(3) 0.0299(7) Uani 1 1 d .
H7 H 0.0418 0.4147 0.1221 0.036 Uiso 1 1 calc R
C10 C 0.11432(7) 0.2453(4) 0.3343(3) 0.0262(7) Uani 1 1 d .
C9 C 0.08649(8) 0.3149(3) 0.4070(3) 0.0301(7) Uani 1 1 d .
H9 H 0.0865 0.3206 0.5084 0.036 Uiso 1 1 calc R
C3 C 0.03093(7) 0.1719(3) -0.0514(3) 0.0230(7) Uani 1 1 d .
C8 C 0.05884(8) 0.3754(4) 0.3279(3) 0.0326(8) Uani 1 1 d .
H8 H 0.0391 0.4215 0.3747 0.039 Uiso 1 1 calc R
C5 C 0.12629(7) 0.3210(4) -0.0987(3) 0.0329(8) Uani 1 1 d .
H5A H 0.1392 0.2318 -0.1294 0.049 Uiso 1 1 calc R
H5B H 0.1409 0.3749 -0.0285 0.049 Uiso 1 1 calc R
H5C H 0.1218 0.3848 -0.1816 0.049 Uiso 1 1 calc R
C4 C 0.06426(7) 0.2367(3) -0.1195(3) 0.0236(7) Uani 1 1 d .
C13 C 0.18919(7) 0.2654(4) 0.2302(3) 0.0294(7) Uani 1 1 d .
C12 C 0.17688(8) 0.1602(4) 0.3438(3) 0.0283(7) Uani 1 1 d .
C1 C 0.0000 -0.0066(6) 0.0901(5) 0.0321(10) Uani 1 2 d S
H1 H 0.0000 -0.0882 0.1543 0.039 Uiso 1 2 calc SR
C2 C 0.03210(7) 0.0532(3) 0.0431(3) 0.0297(7) Uani 1 1 d .
H2 H 0.0545 0.0141 0.0747 0.036 Uiso 1 1 calc R
C14 C 0.21138(8) 0.2128(4) 0.1225(4) 0.0393(9) Uani 1 1 d .
H14 H 0.2170 0.1103 0.1165 0.047 Uiso 1 1 calc R
C11 C 0.13703(8) 0.0967(4) 0.5387(3) 0.0374(8) Uani 1 1 d .
H11A H 0.1305 -0.0055 0.5145 0.056 Uiso 1 1 calc R
H11B H 0.1172 0.1429 0.5919 0.056 Uiso 1 1 calc R
H11C H 0.1589 0.0967 0.5976 0.056 Uiso 1 1 calc R
C15 C 0.22537(8) 0.3119(5) 0.0236(4) 0.0445(9) Uani 1 1 d .
H15 H 0.2403 0.2786 -0.0524 0.053 Uiso 1 1 calc R
C17 C 0.19469(8) 0.5037(5) 0.1495(4) 0.0385(8) Uani 1 1 d .
H17 H 0.1891 0.6060 0.1584 0.046 Uiso 1 1 calc R
C16 C 0.21700(8) 0.4604(4) 0.0388(4) 0.0393(9) Uani 1 1 d .
H16 H 0.2264 0.5316 -0.0259 0.047 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 0.0033 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
C4 N2 C6 123.5(2) . .
C4 N2 C5 118.9(2) . .
C6 N2 C5 117.5(2) . .
C12 N4 C10 122.3(2) . .
C12 N4 C11 116.3(2) . .
C10 N4 C11 119.4(2) . .
C3 N1 C3 117.7(3) . 4
C13 N5 C17 116.3(3) . .
C6 N3 C10 117.0(3) . .
N3 C6 C7 124.8(2) . .
N3 C6 N2 114.0(2) . .
C7 C6 N2 121.2(3) . .
C6 C7 C8 116.7(3) . .
C6 C7 H7 121.7 . .
C8 C7 H7 121.7 . .
N3 C10 C9 123.4(3) . .
N3 C10 N4 115.0(3) . .
C9 C10 N4 121.5(2) . .
C8 C9 C10 118.0(3) . .
C8 C9 H9 121.0 . .
C10 C9 H9 121.0 . .
N1 C3 C2 122.9(3) . .
N1 C3 C4 114.0(3) . .
C2 C3 C4 122.8(2) . .
C9 C8 C7 120.0(3) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
N2 C5 H5A 109.5 . .
N2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
N2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
O1 C4 N2 122.5(2) . .
O1 C4 C3 119.1(2) . .
N2 C4 C3 118.3(2) . .
N5 C13 C14 123.5(3) . .
N5 C13 C12 117.5(3) . .
C14 C13 C12 118.8(3) . .
O2 C12 N4 120.9(3) . .
O2 C12 C13 119.3(3) . .
N4 C12 C13 119.6(3) . .
C2 C1 C2 119.3(4) . 4
C2 C1 H1 120.3 . .
C2 C1 H1 120.3 4 .
C1 C2 C3 118.5(3) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
C13 C14 C15 119.2(3) . .
C13 C14 H14 120.4 . .
C15 C14 H14 120.4 . .
N4 C11 H11A 109.5 . .
N4 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N4 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C16 C15 C14 118.2(3) . .
C16 C15 H15 120.9 . .
C14 C15 H15 120.9 . .
N5 C17 C16 123.8(4) . .
N5 C17 H17 118.1 . .
C16 C17 H17 118.1 . .
C17 C16 C15 119.0(3) . .
C17 C16 H16 120.5 . .
C15 C16 H16 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.227(3) .
N2 C4 1.351(3) .
N2 C6 1.440(3) .
N2 C5 1.471(3) .
O2 C12 1.227(3) .
N4 C12 1.379(3) .
N4 C10 1.412(4) .
N4 C11 1.464(4) .
N1 C3 1.340(3) .
N1 C3 1.340(3) 4
N5 C13 1.345(4) .
N5 C17 1.349(4) .
N3 C6 1.334(3) .
N3 C10 1.334(3) .
C6 C7 1.379(4) .
C7 C8 1.393(4) .
C7 H7 0.9500 .
C10 C9 1.386(4) .
C9 C8 1.378(4) .
C9 H9 0.9500 .
C3 C2 1.390(4) .
C3 C4 1.508(4) .
C8 H8 0.9500 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C13 C14 1.384(4) .
C13 C12 1.497(4) .
C1 C2 1.379(4) .
C1 C2 1.379(4) 4
C1 H1 0.9500 .
C2 H2 0.9500 .
C14 C15 1.387(5) .
C14 H14 0.9500 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C15 C16 1.382(5) .
C15 H15 0.9500 .
C17 C16 1.382(5) .
C17 H17 0.9500 .
C16 H16 0.9500 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.500 0.139 0.108 11.0 6.7
2 0.000 0.360 0.608 11.0 6.7
3 0.000 0.639 0.108 11.0 6.7
4 0.500 0.860 0.608 11.0 6.7
