#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:05:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178420 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/41/4024118.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_4024118
loop_
_publ_author_name
'Anjan Patel'
'Falk Liebner'
'Thomas Netscher'
'Kurt Mereiter'
'Thomas Rosenau'
_publ_contact_author_address
;
 Prof. Dr. Thomas Rosenau
 Department of Chemistry,  
 University of Natural Resources (BOKU), 
 Muthgasse 18, 
 A-1190 Vienna, Austria 
;
_publ_contact_author_email       thomas.rosenau@boku.ac.at
_publ_contact_author_fax         '+43-1-36006 6059'
_publ_contact_author_name        'Prof. Dr. Thomas Rosenau'
_publ_contact_author_phone       '+43-1-36006 6061'
_publ_section_title
;
 Vitamin E Chemistry. Nitration of Non-α-tocopherols:
 Products and Mechanistic Considerations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6504
_journal_page_last               6512
_journal_paper_doi               10.1021/jo0706832
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C13 H17 N O4'
_chemical_formula_sum            'C13 H17 N O4'
_chemical_formula_weight         251.28
_chemical_name_common            'compound (14)'
_chemical_name_systematic
; 
6-Hydroxy-7-nitro-2,2,5,8-tetramethylchroman
;
_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                 94.448(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8349(13)
_cell_length_b                   7.2041(11)
_cell_length_c                   19.113(3)
_cell_measurement_reflns_used    1604
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.47
_cell_volume                     1212.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT, SADABS, XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  '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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5521
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'program SADABS, V2.10'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2601
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0430
_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)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                1768
_reflns_number_total             2601
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0706832si20070403_060801_4.cif
_cod_data_source_block           14=1176
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4024118
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.58773(11) 0.37774(16) 0.17977(5) 0.0313(3) Uani 1 1 d U . .
O2 O 0.39082(13) 0.17288(16) -0.08926(5) 0.0377(3) Uani 1 1 d U . .
H2O H 0.4618 0.1785 -0.1160 0.055(6) Uiso 1 1 calc R . .
O3 O 0.66280(14) 0.21353(18) -0.11793(6) 0.0435(3) Uani 1 1 d U . .
O4 O 0.81970(13) 0.36992(19) -0.05019(6) 0.0442(3) Uani 1 1 d U . .
N N 0.69895(15) 0.28692(19) -0.05998(7) 0.0309(3) Uani 1 1 d U . .
C1 C 0.49918(17) 0.3251(2) 0.23805(8) 0.0312(4) Uani 1 1 d U . .
C2 C 0.33345(17) 0.3686(2) 0.21735(8) 0.0302(4) Uani 1 1 d U . .
H2A H 0.2717 0.3348 0.2565 0.036 Uiso 1 1 calc R . .
H2B H 0.3220 0.5036 0.2090 0.036 Uiso 1 1 calc R . .
C3 C 0.27473(16) 0.2644(2) 0.15184(8) 0.0293(4) Uani 1 1 d U . .
H3A H 0.2534 0.1341 0.1644 0.035 Uiso 1 1 calc R . .
H3B H 0.1782 0.3213 0.1328 0.035 Uiso 1 1 calc R . .
C4 C 0.38676(16) 0.2668(2) 0.09609(7) 0.0242(3) Uani 1 1 d U . .
C5 C 0.34154(16) 0.2127(2) 0.02796(8) 0.0263(3) Uani 1 1 d U . .
C6 C 0.44388(17) 0.2195(2) -0.02352(7) 0.0266(3) Uani 1 1 d U . .
C7 C 0.59570(16) 0.2761(2) -0.00509(8) 0.0256(3) Uani 1 1 d U . .
C8 C 0.64570(16) 0.3227(2) 0.06435(8) 0.0250(3) Uani 1 1 d U . .
C9 C 0.53781(16) 0.3207(2) 0.11344(7) 0.0251(3) Uani 1 1 d U . .
C10 C 0.5601(2) 0.4483(3) 0.29779(8) 0.0471(5) Uani 1 1 d U . .
H10A H 0.5462 0.5788 0.2843 0.071 Uiso 1 1 calc R . .
H10B H 0.6685 0.4232 0.3084 0.071 Uiso 1 1 calc R . .
H10C H 0.5053 0.4229 0.3394 0.071 Uiso 1 1 calc R . .
C11 C 0.52690(19) 0.1217(3) 0.25436(9) 0.0415(4) Uani 1 1 d U . .
H11A H 0.6359 0.1005 0.2649 0.062 Uiso 1 1 calc R . .
H11B H 0.4905 0.0466 0.2137 0.062 Uiso 1 1 calc R . .
H11C H 0.4723 0.0863 0.2950 0.062 Uiso 1 1 calc R . .
C12 C 0.18102(16) 0.1490(2) 0.00823(8) 0.0333(4) Uani 1 1 d U . .
H12A H 0.1471 0.0685 0.0453 0.050 Uiso 1 1 calc R . .
H12B H 0.1778 0.0800 -0.0360 0.050 Uiso 1 1 calc R . .
H12C H 0.1140 0.2573 0.0027 0.050 Uiso 1 1 calc R . .
C13 C 0.80779(17) 0.3668(2) 0.08963(8) 0.0343(4) Uani 1 1 d U . .
H13A H 0.8765 0.2837 0.0667 0.051 Uiso 1 1 calc R . .
H13B H 0.8216 0.3496 0.1406 0.051 Uiso 1 1 calc R . .
H13C H 0.8305 0.4958 0.0780 0.051 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
_geom_angle_publ_flag
C9 O1 C1 118.30(11) . . ?
C6 O2 H2O 109.5 . . ?
O4 N O3 120.20(12) . . ?
O4 N C7 120.45(13) . . ?
O3 N C7 119.33(13) . . ?
O1 C1 C10 104.06(12) . . ?
O1 C1 C11 108.71(12) . . ?
C10 C1 C11 111.73(14) . . ?
O1 C1 C2 108.09(12) . . ?
C10 C1 C2 110.81(14) . . ?
C11 C1 C2 112.97(13) . . ?
C3 C2 C1 111.96(12) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 112.10(12) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C9 119.88(13) . . ?
C5 C4 C3 120.15(13) . . ?
C9 C4 C3 119.96(13) . . ?
C6 C5 C4 119.96(13) . . ?
C6 C5 C12 118.98(13) . . ?
C4 C5 C12 121.05(13) . . ?
O2 C6 C5 116.95(13) . . ?
O2 C6 C7 123.78(13) . . ?
C5 C6 C7 119.27(13) . . ?
C8 C7 C6 121.61(13) . . ?
C8 C7 N 120.18(13) . . ?
C6 C7 N 118.20(13) . . ?
C9 C8 C7 116.96(13) . . ?
C9 C8 C13 118.03(13) . . ?
C7 C8 C13 124.96(13) . . ?
O1 C9 C8 115.65(12) . . ?
O1 C9 C4 122.15(13) . . ?
C8 C9 C4 122.19(13) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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
O1 C9 1.3726(17) . ?
O1 C1 1.4601(17) . ?
O2 C6 1.3489(17) . ?
O2 H2O 0.8400 . ?
O3 N 1.2464(17) . ?
O4 N 1.2246(17) . ?
N C7 1.4448(18) . ?
C1 C10 1.512(2) . ?
C1 C11 1.514(2) . ?
C1 C2 1.519(2) . ?
C2 C3 1.516(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5095(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.388(2) . ?
C4 C9 1.405(2) . ?
C5 C6 1.388(2) . ?
C5 C12 1.510(2) . ?
C6 C7 1.420(2) . ?
C7 C8 1.406(2) . ?
C8 C9 1.388(2) . ?
C8 C13 1.509(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O3 0.84 1.80 2.5228(16) 143.5 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C10 -165.84(13) . . . . ?
C9 O1 C1 C11 74.97(16) . . . . ?
C9 O1 C1 C2 -47.99(18) . . . . ?
O1 C1 C2 C3 59.44(17) . . . . ?
C10 C1 C2 C3 172.86(13) . . . . ?
C11 C1 C2 C3 -60.89(17) . . . . ?
C1 C2 C3 C4 -43.24(18) . . . . ?
C2 C3 C4 C5 -166.74(14) . . . . ?
C2 C3 C4 C9 14.38(19) . . . . ?
C9 C4 C5 C6 -2.7(2) . . . . ?
C3 C4 C5 C6 178.40(13) . . . . ?
C9 C4 C5 C12 178.32(14) . . . . ?
C3 C4 C5 C12 -0.6(2) . . . . ?
C4 C5 C6 O2 -177.14(13) . . . . ?
C12 C5 C6 O2 1.8(2) . . . . ?
C4 C5 C6 C7 2.1(2) . . . . ?
C12 C5 C6 C7 -178.92(14) . . . . ?
O2 C6 C7 C8 -179.75(13) . . . . ?
C5 C6 C7 C8 1.1(2) . . . . ?
O2 C6 C7 N 0.8(2) . . . . ?
C5 C6 C7 N -178.34(13) . . . . ?
O4 N C7 C8 -14.5(2) . . . . ?
O3 N C7 C8 166.73(14) . . . . ?
O4 N C7 C6 164.94(14) . . . . ?
O3 N C7 C6 -13.8(2) . . . . ?
C6 C7 C8 C9 -3.5(2) . . . . ?
N C7 C8 C9 175.92(13) . . . . ?
C6 C7 C8 C13 174.00(14) . . . . ?
N C7 C8 C13 -6.6(2) . . . . ?
C1 O1 C9 C8 -160.79(13) . . . . ?
C1 O1 C9 C4 20.2(2) . . . . ?
C7 C8 C9 O1 -176.13(13) . . . . ?
C13 C8 C9 O1 6.2(2) . . . . ?
C7 C8 C9 C4 2.9(2) . . . . ?
C13 C8 C9 C4 -174.79(14) . . . . ?
C5 C4 C9 O1 179.10(13) . . . . ?
C3 C4 C9 O1 -2.0(2) . . . . ?
C5 C4 C9 C8 0.2(2) . . . . ?
C3 C4 C9 C8 179.04(14) . . . . ?
