#------------------------------------------------------------------------------
#$Date: 2019-11-08 02:55:08 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224906 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/85/7058572.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_7058572
loop_
_publ_author_name
'Thaltiri, Vikranth'
'Chavva, Kurumurthy'
'Kumar, B. Sathish'
'Panda, Pradeepta K.'
_publ_section_title
;
 Efficient synthesis of N-methyltetranitropyrrole: A stable, insensitive
 and high energy melt-castable material
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12318
_journal_paper_doi               10.1039/C9NJ01227C
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C5 H4 N4 O6'
_chemical_formula_sum            'C5 H4 N4 O6'
_chemical_formula_weight         216.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-18 deposited with the CCDC.    2019-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   15.7046(10)
_cell_length_b                   19.0277(10)
_cell_length_c                   8.4560(5)
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.64
_cell_volume                     2526.8(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            30783
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         2.594
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.3170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2801
_reflns_number_total             2938
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj01227c2.cif
_cod_data_source_block           nmtrnpy
_cod_depositor_comments
'Adding full bibliography for 7058569--7058572.cif.'
_cod_database_code               7058572
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.6119
_shelx_estimated_absorpt_t_max   0.7456
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O10 O 0.31774(9) 0.2500 0.22183(14) 0.0248(3) Uani 1 2 d S T P
O3 O 0.32041(6) 0.40416(5) 0.38588(11) 0.0238(2) Uani 1 1 d . . .
O2 O 0.47150(6) 0.40231(5) 0.62285(12) 0.0275(3) Uani 1 1 d . . .
O5 O 0.27119(7) 0.56106(5) 0.24358(10) 0.0272(3) Uani 1 1 d . . .
O11 O 0.22041(9) 0.2500 0.40376(17) 0.0282(3) Uani 1 2 d S T P
O4 O 0.42273(6) 0.46334(5) 0.27477(11) 0.0283(3) Uani 1 1 d . . .
O1 O 0.44127(7) 0.43601(5) 0.86323(12) 0.0313(3) Uani 1 1 d . . .
N1 N 0.36927(7) 0.55903(5) 0.73966(11) 0.0158(2) Uani 1 1 d . . .
O6 O 0.23113(8) 0.65053(6) 0.38509(13) 0.0367(3) Uani 1 1 d . . .
O9 O 0.50792(7) 0.19297(6) 0.24533(12) 0.0340(3) Uani 1 1 d . . .
N5 N 0.42146(10) 0.2500 0.71417(15) 0.0180(3) Uani 1 2 d S T P
N8 N 0.29534(10) 0.2500 0.36108(16) 0.0179(3) Uani 1 2 d S T P
N3 N 0.36988(7) 0.45344(5) 0.37842(11) 0.0171(2) Uani 1 1 d . . .
N4 N 0.27083(7) 0.59590(6) 0.36617(12) 0.0206(3) Uani 1 1 d . . .
O8 O 0.62068(10) 0.2500 0.51664(18) 0.0387(4) Uani 1 2 d S T P
N2 N 0.43885(7) 0.44268(5) 0.71894(13) 0.0202(3) Uani 1 1 d . . .
N7 N 0.49175(10) 0.2500 0.30282(17) 0.0221(3) Uani 1 2 d S T P
C3 C 0.31854(7) 0.56972(6) 0.49694(12) 0.0153(3) Uani 1 1 d . . .
C2 C 0.36322(7) 0.50622(5) 0.50331(13) 0.0139(2) Uani 1 1 d . . .
C9 C 0.34545(12) 0.2500 0.64096(18) 0.0177(3) Uani 1 2 d S T P
H9 H 0.2914 0.2500 0.6913 0.021 Uiso 1 2 calc R U P
N6 N 0.57348(12) 0.2500 0.6332(2) 0.0312(4) Uani 1 2 d S T P
C7 C 0.44784(11) 0.2500 0.45430(18) 0.0159(3) Uani 1 2 d S T P
C1 C 0.39381(7) 0.50083(6) 0.65483(13) 0.0149(3) Uani 1 1 d . . .
C8 C 0.35986(11) 0.2500 0.47901(18) 0.0153(3) Uani 1 2 d S T P
C6 C 0.48469(11) 0.2500 0.60135(19) 0.0185(3) Uani 1 2 d S T P
O7 O 0.59780(13) 0.2500 0.7701(2) 0.0652(7) Uani 1 2 d S T P
C4 C 0.32427(7) 0.60140(6) 0.64390(13) 0.0168(3) Uani 1 1 d . . .
H4 H 0.3005 0.6455 0.6722 0.020 Uiso 1 1 calc R U .
C5 C 0.38904(8) 0.57613(7) 0.90573(13) 0.0219(3) Uani 1 1 d . . .
H5A H 0.3683 0.6235 0.9301 0.033 Uiso 1 1 calc R U .
H5B H 0.4508 0.5742 0.9219 0.033 Uiso 1 1 calc R U .
H5C H 0.3611 0.5421 0.9755 0.033 Uiso 1 1 calc R U .
C10 C 0.43162(15) 0.2500 0.88780(19) 0.0248(4) Uani 1 2 d S T P
H1D H 0.3780(16) 0.2500 0.931(3) 0.018(5) Uiso 1 2 d S . P
H2D H 0.4603(12) 0.2895(9) 0.922(2) 0.033(4) 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
C4 N1 C1 108.45(9) .
C4 N1 C5 123.52(10) .
C1 N1 C5 128.01(10) .
C9 N5 C6 108.73(13) .
C9 N5 C10 123.62(16) .
C6 N5 C10 127.65(16) .
O10 N8 O11 123.69(15) .
O10 N8 C8 117.90(15) .
O11 N8 C8 118.41(14) .
O3 N3 O4 126.06(10) .
O3 N3 C2 116.46(9) .
O4 N3 C2 117.46(9) .
O6 N4 O5 124.80(11) .
O6 N4 C3 117.62(11) .
O5 N4 C3 117.56(10) .
O1 N2 O2 125.39(11) .
O1 N2 C1 118.38(11) .
O2 N2 C1 116.22(10) .
O9 N7 O9 126.37(16) 7_565
O9 N7 C7 116.82(8) 7_565
O9 N7 C7 116.81(8) .
C4 C3 C2 108.00(10) .
C4 C3 N4 125.35(11) .
C2 C3 N4 126.55(10) .
C1 C2 C3 106.04(9) .
C1 C2 N3 126.76(10) .
C3 C2 N3 127.01(10) .
N5 C9 C8 108.03(15) .
N5 C9 H9 126.0 .
C8 C9 H9 126.0 .
O7 N6 O8 124.79(19) .
O7 N6 C6 119.19(19) .
O8 N6 C6 116.03(16) .
C6 C7 C8 106.36(14) .
C6 C7 N7 126.75(16) .
C8 C7 N7 126.89(15) .
C2 C1 N1 109.21(9) .
C2 C1 N2 126.07(10) .
N1 C1 N2 124.60(10) .
C9 C8 C7 107.98(15) .
C9 C8 N8 125.16(16) .
C7 C8 N8 126.86(14) .
C7 C6 N5 108.90(15) .
C7 C6 N6 125.88(16) .
N5 C6 N6 125.22(15) .
N1 C4 C3 108.30(10) .
N1 C4 H4 125.8 .
C3 C4 H4 125.8 .
N1 C5 H5A 109.5 .
N1 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
N1 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
N5 C10 H1D 107.4(14) .
N5 C10 H2D 111.4(11) .
H1D C10 H2D 108.7(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O10 N8 1.2290(19) .
O3 N3 1.2193(13) .
O2 N2 1.2302(15) .
O5 N4 1.2305(15) .
O11 N8 1.231(2) .
O4 N3 1.2217(14) .
O1 N2 1.2272(15) .
N1 C4 1.3435(15) .
N1 C1 1.3745(14) .
N1 C5 1.4745(14) .
O6 N4 1.2226(15) .
O9 N7 1.2158(12) .
N5 C9 1.345(2) .
N5 C6 1.377(2) .
N5 C10 1.4769(19) .
N8 C8 1.422(2) .
N3 C2 1.4612(14) .
N4 C3 1.4256(14) .
O8 N6 1.233(2) .
N2 C1 1.4207(14) .
N7 O9 1.2157(12) 7_565
N7 C7 1.455(2) .
C3 C4 1.3841(15) .
C3 C2 1.3984(15) .
C2 C1 1.3721(15) .
C9 C8 1.388(2) .
C9 H9 0.9500 .
N6 O7 1.219(2) .
N6 C6 1.420(2) .
C7 C6 1.371(2) .
C7 C8 1.397(2) .
C4 H4 0.9500 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C10 H1D 0.92(2) .
C10 H2D 0.923(18) .
