#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/53/2225363.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225363
loop_
_publ_author_name
'Ma, Xiao-Yan'
'Wu, Di-Feng'
'Wang, Yang'
'Gao, Guo-Wei'
'Men, Jian'
_publ_section_title
;
 1,3,3-Trimethyl-5-nitro-1-phenylindane
;
_journal_coeditor_code           RZ2417
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o645
_journal_paper_doi               10.1107/S1600536810005647
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H19 N O2'
_chemical_formula_moiety         'C18 H19 N1 O2 '
_chemical_formula_sum            'C18 H19 N O2'
_chemical_formula_weight         281.34
_chemical_name_systematic
;
1,3,3-trimethyl-5-nitro-1-phenylindane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 120.50(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.306(3)
_cell_length_b                   17.600(3)
_cell_length_c                   12.090(4)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      6.21
_cell_measurement_theta_min      5.43
_cell_volume                     1522.8(9)
_computing_cell_refinement       'DIFRAC (Gabe & White, 1993)'
_computing_data_collection       'DIFRAC (Gabe & White, 1993)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD4'
_diffrn_measurement_method       Omega/2-Theta
_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  0.0087
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3123
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        2.136
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.398
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0573
_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)+(0.1033P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1682
_refine_ls_wR_factor_ref         0.1954
_reflns_number_gt                1600
_reflns_number_total             2750
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2417.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C18 H19 N1 O2 '
_cod_database_code               2225363
_cod_database_fobs_code          2225363
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.3148(4) 0.65100(12) -0.0098(2) 0.0834(8) Uani d . 1 . .
O O2 0.0977(4) 0.56794(15) -0.0607(2) 0.0874(8) Uani d . 1 . .
N N1 0.2608(4) 0.58823(15) 0.0018(2) 0.0591(7) Uani d . 1 . .
C C1 0.3981(4) 0.53506(15) 0.0954(2) 0.0462(7) Uani d . 1 . .
C C2 0.5784(4) 0.55976(15) 0.1727(3) 0.0547(8) Uani d . 1 . .
H H2 0.6123 0.6089 0.1647 0.066 Uiso calc R 1 . .
C C3 0.7087(4) 0.51059(14) 0.2623(3) 0.0510(7) Uani d . 1 . .
H H3 0.8313 0.5264 0.3162 0.061 Uiso calc R 1 . .
C C4 0.6543(3) 0.43718(14) 0.2711(2) 0.0414(7) Uani d . 1 . .
C C5 0.4721(4) 0.41334(14) 0.1900(2) 0.0412(6) Uani d . 1 . .
C C6 0.3404(4) 0.46264(15) 0.1011(2) 0.0470(7) Uani d . 1 . .
H H6 0.2174 0.4474 0.0472 0.056 Uiso calc R 1 . .
C C7 0.7734(4) 0.37453(13) 0.3611(2) 0.0433(7) Uani d . 1 . .
C C8 0.6503(4) 0.30424(14) 0.2923(3) 0.0498(7) Uani d . 1 . .
H H8A 0.6888 0.2815 0.2363 0.060 Uiso calc R 1 . .
H H8B 0.6636 0.2666 0.3550 0.060 Uiso calc R 1 . .
C C9 0.4461(4) 0.33044(14) 0.2134(3) 0.0475(7) Uani d . 1 . .
C C10 0.9639(4) 0.36996(17) 0.3688(3) 0.0556(8) Uani d . 1 . .
H H10A 0.9449 0.3681 0.2836 0.083 Uiso calc R 1 . .
H H10B 1.0286 0.3250 0.4149 0.083 Uiso calc R 1 . .
H H10C 1.0369 0.4139 0.4126 0.083 Uiso calc R 1 . .
C C11 0.3445(4) 0.32497(16) 0.2899(3) 0.0629(8) Uani d . 1 . .
H H11A 0.2224 0.3471 0.2409 0.094 Uiso calc R 1 . .
H H11B 0.4147 0.3518 0.3696 0.094 Uiso calc R 1 . .
H H11C 0.3330 0.2726 0.3070 0.094 Uiso calc R 1 . .
C C12 0.3375(5) 0.28566(17) 0.0888(3) 0.0691(9) Uani d . 1 . .
H H12A 0.3957 0.2920 0.0382 0.104 Uiso calc R 1 . .
H H12B 0.2113 0.3040 0.0416 0.104 Uiso calc R 1 . .
H H12C 0.3370 0.2328 0.1082 0.104 Uiso calc R 1 . .
C C13 0.8050(3) 0.38424(14) 0.4966(2) 0.0424(7) Uani d . 1 . .
C C14 0.7377(4) 0.44583(15) 0.5326(3) 0.0525(7) Uani d . 1 . .
H H14 0.6684 0.4832 0.4727 0.063 Uiso calc R 1 . .
C C15 0.7731(5) 0.45205(18) 0.6572(3) 0.0657(9) Uani d . 1 . .
H H15 0.7272 0.4936 0.6801 0.079 Uiso calc R 1 . .
C C16 0.8742(5) 0.39802(18) 0.7466(3) 0.0649(9) Uani d . 1 . .
H H16 0.8993 0.4030 0.8305 0.078 Uiso calc R 1 . .
C C17 0.9385(4) 0.33629(17) 0.7115(3) 0.0619(8) Uani d . 1 . .
H H17 1.0052 0.2986 0.7714 0.074 Uiso calc R 1 . .
C C18 0.9053(4) 0.32970(15) 0.5890(3) 0.0536(8) Uani d . 1 . .
H H18 0.9512 0.2876 0.5672 0.064 Uiso calc R 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 N1 O1 . . 123.2(3) ?
O2 N1 C1 . . 118.3(3) ?
O1 N1 C1 . . 118.5(3) ?
C2 C1 C6 . . 123.1(2) ?
C2 C1 N1 . . 118.4(2) ?
C6 C1 N1 . . 118.5(3) ?
C1 C2 C3 . . 119.1(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 119.1(3) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C5 C4 C3 . . 120.5(2) ?
C5 C4 C7 . . 111.6(2) ?
C3 C4 C7 . . 127.9(2) ?
C6 C5 C4 . . 120.6(2) ?
C6 C5 C9 . . 128.0(2) ?
C4 C5 C9 . . 111.5(2) ?
C1 C6 C5 . . 117.6(3) ?
C1 C6 H6 . . 121.2 ?
C5 C6 H6 . . 121.2 ?
C4 C7 C13 . . 112.52(19) ?
C4 C7 C10 . . 111.0(2) ?
C13 C7 C10 . . 109.2(2) ?
C4 C7 C8 . . 100.6(2) ?
C13 C7 C8 . . 111.82(19) ?
C10 C7 C8 . . 111.6(2) ?
C9 C8 C7 . . 108.3(2) ?
C9 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
C9 C8 H8B . . 110.0 ?
C7 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.4 ?
C5 C9 C12 . . 112.4(2) ?
C5 C9 C8 . . 100.8(2) ?
C12 C9 C8 . . 111.8(2) ?
C5 C9 C11 . . 110.2(2) ?
C12 C9 C11 . . 109.4(2) ?
C8 C9 C11 . . 112.2(2) ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C18 C13 C14 . . 117.5(2) ?
C18 C13 C7 . . 119.5(2) ?
C14 C13 C7 . . 123.0(2) ?
C15 C14 C13 . . 120.4(3) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C16 C15 C14 . . 120.9(3) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 119.2(3) ?
C15 C16 H16 . . 120.4 ?
C17 C16 H16 . . 120.4 ?
C18 C17 C16 . . 120.5(3) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C17 C18 C13 . . 121.5(2) ?
C17 C18 H18 . . 119.2 ?
C13 C18 H18 . . 119.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . 1.227(3) ?
O2 N1 . 1.223(3) ?
N1 C1 . 1.465(3) ?
C1 C2 . 1.373(4) ?
C1 C6 . 1.376(4) ?
C2 C3 . 1.380(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.390(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.386(4) ?
C4 C7 . 1.512(3) ?
C5 C6 . 1.382(4) ?
C5 C9 . 1.522(3) ?
C6 H6 . 0.9300 ?
C7 C13 . 1.531(3) ?
C7 C10 . 1.540(4) ?
C7 C8 . 1.551(4) ?
C8 C9 . 1.535(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C12 . 1.524(4) ?
C9 C11 . 1.539(4) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C18 . 1.385(4) ?
C13 C14 . 1.387(3) ?
C14 C15 . 1.385(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.363(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.370(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.366(4) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 N1 C1 C2 . . . . -175.0(2) ?
O1 N1 C1 C2 . . . . 4.8(3) ?
O2 N1 C1 C6 . . . . 5.4(3) ?
O1 N1 C1 C6 . . . . -174.9(2) ?
C6 C1 C2 C3 . . . . -1.1(4) ?
N1 C1 C2 C3 . . . . 179.2(2) ?
C1 C2 C3 C4 . . . . 0.6(4) ?
C2 C3 C4 C5 . . . . 0.7(4) ?
C2 C3 C4 C7 . . . . 179.7(2) ?
C3 C4 C5 C6 . . . . -1.5(3) ?
C7 C4 C5 C6 . . . . 179.3(2) ?
C3 C4 C5 C9 . . . . 178.0(2) ?
C7 C4 C5 C9 . . . . -1.2(3) ?
C2 C1 C6 C5 . . . . 0.3(4) ?
N1 C1 C6 C5 . . . . 180.0(2) ?
C4 C5 C6 C1 . . . . 1.0(3) ?
C9 C5 C6 C1 . . . . -178.4(2) ?
C5 C4 C7 C13 . . . . -102.2(2) ?
C3 C4 C7 C13 . . . . 78.7(3) ?
C5 C4 C7 C10 . . . . 135.1(2) ?
C3 C4 C7 C10 . . . . -44.0(3) ?
C5 C4 C7 C8 . . . . 16.9(2) ?
C3 C4 C7 C8 . . . . -162.2(2) ?
C4 C7 C8 C9 . . . . -26.4(2) ?
C13 C7 C8 C9 . . . . 93.2(2) ?
C10 C7 C8 C9 . . . . -144.1(2) ?
C6 C5 C9 C12 . . . . 45.0(3) ?
C4 C5 C9 C12 . . . . -134.4(2) ?
C6 C5 C9 C8 . . . . 164.2(2) ?
C4 C5 C9 C8 . . . . -15.2(2) ?
C6 C5 C9 C11 . . . . -77.2(3) ?
C4 C5 C9 C11 . . . . 103.4(3) ?
C7 C8 C9 C5 . . . . 25.7(2) ?
C7 C8 C9 C12 . . . . 145.3(2) ?
C7 C8 C9 C11 . . . . -91.4(3) ?
C4 C7 C13 C18 . . . . 177.5(2) ?
C10 C7 C13 C18 . . . . -58.8(3) ?
C8 C7 C13 C18 . . . . 65.2(3) ?
C4 C7 C13 C14 . . . . -2.6(3) ?
C10 C7 C13 C14 . . . . 121.0(3) ?
C8 C7 C13 C14 . . . . -115.0(3) ?
C18 C13 C14 C15 . . . . 0.8(4) ?
C7 C13 C14 C15 . . . . -179.1(3) ?
C13 C14 C15 C16 . . . . 0.0(5) ?
C14 C15 C16 C17 . . . . -1.1(5) ?
C15 C16 C17 C18 . . . . 1.5(5) ?
C16 C17 C18 C13 . . . . -0.6(4) ?
C14 C13 C18 C17 . . . . -0.5(4) ?
C7 C13 C18 C17 . . . . 179.4(3) ?
