#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/32/2233240.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_2233240
loop_
_publ_author_name
'Muthukumaran, J.'
'Parthiban, A.'
'Surya Prakash Rao, H.'
'Krishna, R.'
_publ_section_title
;
 6-Ethyl-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine
;
_journal_coeditor_code           LH5388
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o180
_journal_page_last               o181
_journal_paper_doi               10.1107/S1600536811053554
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H15 N3 O5'
_chemical_formula_moiety         'C13 H15 N3 O5'
_chemical_formula_sum            'C13 H15 N3 O5'
_chemical_formula_weight         293.28
_chemical_name_systematic
;
6-Ethyl-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.484(9)
_cell_angle_beta                 71.728(11)
_cell_angle_gamma                83.234(9)
_cell_formula_units_Z            2
_cell_length_a                   8.2538(10)
_cell_length_b                   9.0431(9)
_cell_length_c                   10.3323(12)
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0721
_cell_measurement_theta_min      2.7332
_cell_volume                     701.75(15)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       '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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4281
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.335
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     122
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0734
_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)+(0.1377P)²+0.1022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2324
_reflns_number_gt                1520
_reflns_number_total             2463
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5388.cif
_cod_data_source_block           I
_cod_original_cell_volume        701.75(14)
_cod_database_code               2233240
_cod_database_fobs_code          2233240
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4139(2) 0.2857(3) 1.1942(2) 0.0468(6) Uani d . 1 1 . .
C C1 0.5007(4) 0.2700(4) 1.0581(3) 0.0401(8) Uani d . 1 1 . .
C C8 0.6569(4) 0.4021(4) 1.1982(3) 0.0383(8) Uani d . 1 1 . .
O O2 0.6415(3) 0.5176(3) 1.3724(2) 0.0569(7) Uani d . 1 1 . .
O O3 0.8792(3) 0.5209(3) 1.2039(2) 0.0636(8) Uani d . 1 1 . .
N N2 0.7266(3) 0.4819(3) 1.2608(3) 0.0435(7) Uani d . 1 1 . .
C C9 0.4856(4) 0.3561(4) 1.2598(3) 0.0394(8) Uani d . 1 1 . .
N N1 0.3831(3) 0.3738(3) 1.3790(3) 0.0490(8) Uani d . 1 1 . .
H H1 0.4224 0.4167 1.4267 0.059 Uiso calc R 1 1 . .
C C6 0.6684(4) 0.3088(4) 0.9922(3) 0.0380(8) Uani d . 1 1 . .
C C2 0.4066(4) 0.2138(4) 0.9941(4) 0.0490(9) Uani d . 1 1 . .
H H2 0.2935 0.1877 1.0408 0.059 Uiso calc R 1 1 . .
C C5 0.7416(4) 0.2899(4) 0.8563(3) 0.0489(9) Uani d . 1 1 . .
H H5 0.8551 0.3151 0.8099 0.059 Uiso calc R 1 1 . .
C C7 0.7700(4) 0.3607(4) 1.0681(3) 0.0413(8) Uani d . 1 1 B .
H H7 0.8238 0.4563 1.0044 0.050 Uiso calc R 1 1 . .
C C4 0.6519(5) 0.2354(4) 0.7888(4) 0.0528(9) Uani d . 1 1 C .
C C3 0.4833(5) 0.1970(4) 0.8600(4) 0.0548(10) Uani d . 1 1 . .
H H3 0.4209 0.1592 0.8160 0.066 Uiso calc R 1 1 . .
C C11 0.9145(4) 0.2466(4) 1.0924(4) 0.0588(10) Uani d DU 1 1 . .
H H11A 0.9964 0.2440 1.0021 0.071 Uiso calc R 1 1 A 1
H H11B 0.9726 0.2804 1.1468 0.071 Uiso calc R 1 1 A 1
N N3A 0.8506(10) 0.0891(5) 1.1687(9) 0.085(2) Uani d PDU 0.629(7) 1 B 1
O O4A 0.7196(14) 0.0755(17) 1.2654(17) 0.113(3) Uani d PDU 0.629(7) 1 B 1
O O5A 0.9064(12) -0.0297(9) 1.1366(11) 0.169(3) Uani d PDU 0.629(7) 1 B 1
N N3B 0.8580(16) 0.0962(10) 1.1944(16) 0.085(2) Uani d PDU 0.371(7) 1 B 2
O O4B 0.717(2) 0.043(3) 1.240(3) 0.113(3) Uani d PDU 0.371(7) 1 B 2
O O5B 0.9759(19) 0.0179(16) 1.2268(18) 0.169(3) Uani d PDU 0.371(7) 1 B 2
C C12 0.7376(6) 0.2240(6) 0.6386(4) 0.0778(13) Uani d DU 1 1 . .
H H12A 0.7279 0.3246 0.5751 0.093 Uiso calc PR 0.533(8) 1 C 1
H H12B 0.8581 0.2008 0.6277 0.093 Uiso calc PR 0.533(8) 1 C 1
H H12C 0.6550 0.2506 0.5857 0.093 Uiso calc PR 0.467(8) 1 C 2
H H12D 0.8286 0.2970 0.5932 0.093 Uiso calc PR 0.467(8) 1 C 2
C C13A 0.6702(15) 0.1062(12) 0.5913(10) 0.114(3) Uani d PDU 0.533(8) 1 C 1
H H13A 0.7334 0.1097 0.4951 0.171 Uiso calc PR 0.533(8) 1 C 1
H H13B 0.5517 0.1291 0.5983 0.171 Uiso calc PR 0.533(8) 1 C 1
H H13C 0.6828 0.0050 0.6506 0.171 Uiso calc PR 0.533(8) 1 C 1
C C13B 0.8100(18) 0.0627(8) 0.6369(12) 0.114(3) Uani d PDU 0.467(8) 1 C 2
H H13D 0.8636 0.0583 0.5411 0.171 Uiso calc PR 0.467(8) 1 C 2
H H13E 0.7197 -0.0094 0.6804 0.171 Uiso calc PR 0.467(8) 1 C 2
H H13F 0.8929 0.0369 0.6881 0.171 Uiso calc PR 0.467(8) 1 C 2
C C10 0.2057(4) 0.3261(6) 1.4383(4) 0.0722(13) Uani d . 1 1 . .
H H10A 0.1380 0.3912 1.3825 0.108 Uiso calc R 1 1 . .
H H10B 0.1624 0.3350 1.5336 0.108 Uiso calc R 1 1 . .
H H10C 0.2001 0.2209 1.4376 0.108 Uiso calc R 1 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'
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
C9 O1 C1 120.9(2)
C6 C1 C2 122.1(3)
C6 C1 O1 122.2(3)
C2 C1 O1 115.7(3)
N2 C8 C9 120.1(3)
N2 C8 C7 117.6(2)
C9 C8 C7 122.2(3)
O3 N2 O2 119.8(3)
O3 N2 C8 118.7(2)
O2 N2 C8 121.5(3)
N1 C9 O1 113.2(3)
N1 C9 C8 126.7(3)
O1 C9 C8 120.1(3)
C9 N1 C10 125.0(3)
C9 N1 H1 117.5
C10 N1 H1 117.5
C1 C6 C5 117.5(3)
C1 C6 C7 120.6(3)
C5 C6 C7 121.8(3)
C3 C2 C1 118.7(3)
C3 C2 H2 120.6
C1 C2 H2 120.6
C4 C5 C6 122.2(3)
C4 C5 H5 118.9
C6 C5 H5 118.9
C8 C7 C6 111.4(2)
C8 C7 C11 114.3(3)
C6 C7 C11 111.6(3)
C8 C7 H7 106.3
C6 C7 H7 106.3
C11 C7 H7 106.3
C5 C4 C3 118.2(3)
C5 C4 C12 119.3(3)
C3 C4 C12 122.5(3)
C2 C3 C4 121.4(3)
C2 C3 H3 119.3
C4 C3 H3 119.3
N3B C11 C7 114.4(6)
N3A C11 C7 111.4(4)
N3B C11 H11A 117.3
N3A C11 H11A 109.3
C7 C11 H11A 109.3
N3B C11 H11B 97.5
N3A C11 H11B 109.3
C7 C11 H11B 109.3
H11A C11 H11B 108.0
O4A N3A O5A 114.3(8)
O4A N3A C11 118.5(9)
O5A N3A C11 126.8(8)
O4B N3B O5B 118.9(19)
O4B N3B C11 128.9(19)
O5B N3B C11 112.1(11)
C13B C12 C13A 53.2(7)
C13B C12 C4 110.9(5)
C13A C12 C4 116.9(5)
C13B C12 H12A 141.0
C13A C12 H12A 108.1
C4 C12 H12A 108.1
C13B C12 H12B 59.8
C13A C12 H12B 108.1
C4 C12 H12B 108.1
H12A C12 H12B 107.3
C13B C12 H12C 109.5
C13A C12 H12C 57.4
C4 C12 H12C 109.5
H12A C12 H12C 56.1
H12B C12 H12C 142.2
C13B C12 H12D 109.5
C13A C12 H12D 133.6
C4 C12 H12D 109.5
H12A C12 H12D 55.3
H12B C12 H12D 53.9
H12C C12 H12D 108.0
C12 C13A H13A 109.5
C12 C13A H13B 109.5
H13A C13A H13B 109.5
C12 C13A H13C 109.5
H13A C13A H13C 109.5
H13B C13A H13C 109.5
C12 C13B H13D 109.5
C12 C13B H13E 109.5
H13D C13B H13E 109.5
C12 C13B H13F 109.5
H13D C13B H13F 109.5
H13E C13B H13F 109.5
N1 C10 H10A 109.5
N1 C10 H10B 109.5
H10A C10 H10B 109.5
N1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.342(4)
O1 C1 1.403(3)
C1 C6 1.375(4)
C1 C2 1.380(4)
C8 N2 1.366(4)
C8 C9 1.414(4)
C8 C7 1.496(4)
O2 N2 1.256(3)
O3 N2 1.256(3)
C9 N1 1.298(4)
N1 C10 1.463(4)
N1 H1 0.8600
C6 C5 1.395(4)
C6 C7 1.501(4)
C2 C3 1.376(5)
C2 H2 0.9300
C5 C4 1.372(5)
C5 H5 0.9300
C7 C11 1.517(5)
C7 H7 0.9800
C4 C3 1.387(5)
C4 C12 1.518(5)
C3 H3 0.9300
C11 N3B 1.4847(11)
C11 N3A 1.4847(11)
C11 H11A 0.9700
C11 H11B 0.9700
N3A O4A 1.2113(11)
N3A O5A 1.2115(11)
N3B O4B 1.2114(11)
N3B O5B 1.2117(11)
C12 C13B 1.5122(11)
C12 C13A 1.5125(11)
C12 H12A 0.9700
C12 H12B 0.9700
C12 H12C 0.9700
C12 H12D 0.9700
C13A H13A 0.9600
C13A H13B 0.9600
C13A H13C 0.9600
C13B H13D 0.9600
C13B H13E 0.9600
C13B H13F 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O2 1 0.86 1.97 2.600(3) 129
N1 H1 O2 2_668 0.86 2.21 2.943(4) 143
C11 H11A O3 2_767 0.97 2.58 3.258(4) 128
C12 H12A O2 1_554 0.97 2.55 3.457(5) 156
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
C9 O1 C1 C6 7.7(5)
C9 O1 C1 C2 -172.0(3)
C9 C8 N2 O3 179.8(3)
C7 C8 N2 O3 2.4(4)
C9 C8 N2 O2 -0.7(5)
C7 C8 N2 O2 -178.2(3)
C1 O1 C9 N1 174.0(3)
C1 O1 C9 C8 -6.3(4)
N2 C8 C9 N1 -4.2(5)
C7 C8 C9 N1 173.1(3)
N2 C8 C9 O1 176.1(3)
C7 C8 C9 O1 -6.6(5)
O1 C9 N1 C10 -1.1(5)
C8 C9 N1 C10 179.2(4)
C2 C1 C6 C5 0.3(5)
O1 C1 C6 C5 -179.4(3)
C2 C1 C6 C7 -176.3(3)
O1 C1 C6 C7 4.0(5)
C6 C1 C2 C3 -0.4(5)
O1 C1 C2 C3 179.3(3)
C1 C6 C5 C4 0.2(5)
C7 C6 C5 C4 176.8(3)
N2 C8 C7 C6 -166.3(3)
C9 C8 C7 C6 16.4(4)
N2 C8 C7 C11 66.0(4)
C9 C8 C7 C11 -111.3(3)
C1 C6 C7 C8 -14.8(4)
C5 C6 C7 C8 168.7(3)
C1 C6 C7 C11 114.3(3)
C5 C6 C7 C11 -62.2(4)
C6 C5 C4 C3 -0.6(5)
C6 C5 C4 C12 177.5(3)
C1 C2 C3 C4 0.0(5)
C5 C4 C3 C2 0.4(6)
C12 C4 C3 C2 -177.5(4)
C8 C7 C11 N3B 59.4(9)
C6 C7 C11 N3B -68.2(9)
C8 C7 C11 N3A 72.3(5)
C6 C7 C11 N3A -55.3(5)
N3B C11 N3A O4A 65(4)
C7 C11 N3A O4A -41.2(12)
N3B C11 N3A O5A -123(4)
C7 C11 N3A O5A 131.0(10)
N3A C11 N3B O4B -64(4)
C7 C11 N3B O4B 15(2)
N3A C11 N3B O5B 112(4)
C7 C11 N3B O5B -169.6(13)
C5 C4 C12 C13B 96.2(7)
C3 C4 C12 C13B -85.9(8)
C5 C4 C12 C13A 154.5(7)
C3 C4 C12 C13A -27.5(8)
