#------------------------------------------------------------------------------
#$Date: 2026-03-04 00:30:15 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304698 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/55/7135515.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_7135515
loop_
_publ_author_name
'Shanmugapriya, V.'
'Panda, Pradeepta K.'
_publ_section_title
;
 A bipyrrole scaffold as an emerging Frontier in robust design of high
 energy materials.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1936
_journal_page_last               1940
_journal_paper_doi               10.1039/d5cc06662j
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C10 H8 N6 O8'
_chemical_formula_sum            'C10 H8 N6 O8'
_chemical_formula_weight         340.22
_chemical_name_systematic        EXT103A
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-11-17 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.392(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5497(18)
_cell_length_b                   13.502(3)
_cell_length_c                   12.107(3)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.40
_cell_volume                     1386.0(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295.00
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.918
_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  0.0931
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18699
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.184
_diffrn_reflns_theta_min         2.402
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.2118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1823 before and 0.1263 after correction.
The Ratio of minimum to maximum transmission is 0.2841.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0980
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2600
_refine_ls_wR_factor_ref         0.2791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2100
_reflns_number_total             2826
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc06662j2.cif
_cod_data_source_block           VSP-C6
_cod_database_code               7135515
_shelx_shelxl_version_number     2018/3
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I)
2.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00O(H00D,H00E,H00F)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.1652(3) 0.58551(17) 0.66588(19) 0.0399(6) Uani 1 1 d . . . . .
O002 O -0.0685(3) 0.73092(17) 0.5663(2) 0.0581(7) Uani 1 1 d . . . . .
N003 N -0.0062(3) 0.80819(18) 0.5413(2) 0.0468(7) Uani 1 1 d . . . . .
N004 N 0.4111(3) 0.78513(17) 0.62499(19) 0.0398(6) Uani 1 1 d . . . . .
N005 N 0.5203(4) 0.9550(2) 0.6340(2) 0.0508(7) Uani 1 1 d . . . . .
N006 N 0.3562(3) 0.59159(18) 0.4195(2) 0.0450(7) Uani 1 1 d . . . . .
O007 O 0.3912(3) 0.52283(19) 0.3617(2) 0.0687(8) Uani 1 1 d . . . . .
O008 O 0.4859(4) 1.04268(19) 0.6246(2) 0.0714(8) Uani 1 1 d . . . . .
O009 O -0.0791(3) 0.8754(2) 0.4912(3) 0.0752(9) Uani 1 1 d . . . . .
O00A O 0.3860(4) 0.67758(18) 0.4003(2) 0.0713(8) Uani 1 1 d . . . . .
O00B O 0.6537(3) 0.9246(2) 0.6595(3) 0.0749(8) Uani 1 1 d . . . . .
N00C N 0.0715(4) 0.4139(2) 0.6851(2) 0.0605(8) Uani 1 1 d . . . . .
C00D C 0.2664(3) 0.7436(2) 0.5996(2) 0.0367(7) Uani 1 1 d . . . . .
O00E O 0.1007(5) 0.3281(2) 0.6650(3) 0.0939(11) Uani 1 1 d . . . . .
C00F C 0.2402(3) 0.63655(19) 0.5923(2) 0.0355(7) Uani 1 1 d . . . . .
O00G O -0.0228(4) 0.4392(3) 0.7445(3) 0.0956(11) Uani 1 1 d . . . . .
C00H C 0.2238(4) 0.4757(2) 0.5385(2) 0.0423(7) Uani 1 1 d . . . . .
H00H H 0.233337 0.416969 0.499755 0.051 Uiso 1 1 calc R U . . .
C00I C 0.2405(4) 0.9098(2) 0.5783(2) 0.0432(8) Uani 1 1 d . . . . .
H00I H 0.198585 0.972632 0.563082 0.052 Uiso 1 1 calc R U . . .
C00J C 0.1594(3) 0.81974(19) 0.5711(2) 0.0384(7) Uani 1 1 d . . . . .
C00K C 0.2776(3) 0.56916(19) 0.5128(2) 0.0371(7) Uani 1 1 d . . . . .
C00L C 0.1549(3) 0.4886(2) 0.6315(2) 0.0406(7) Uani 1 1 d . . . . .
C00M C 0.3922(3) 0.88625(19) 0.6120(2) 0.0402(7) Uani 1 1 d . . . . .
C00N C 0.1181(5) 0.6278(3) 0.7686(3) 0.0584(9) Uani 1 1 d . . . . .
H00A H 0.163603 0.589575 0.831411 0.088 Uiso 1 1 calc R U . . .
H00B H 0.005196 0.626595 0.764528 0.088 Uiso 1 1 calc R U . . .
H00C H 0.154574 0.695007 0.776734 0.088 Uiso 1 1 calc R U . . .
C00O C 0.5556(4) 0.7290(3) 0.6635(3) 0.0599(9) Uani 1 1 d . . . . .
H00D H 0.599984 0.752772 0.735493 0.090 Uiso 1 1 calc R U . . .
H00E H 0.630520 0.737709 0.611672 0.090 Uiso 1 1 calc R U . . .
H00F H 0.530372 0.660011 0.668443 0.090 Uiso 1 1 calc R U . . .
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
C00F N001 C00L 107.7(2) . . ?
C00F N001 C00N 124.3(3) . . ?
C00L N001 C00N 127.8(3) . . ?
O002 N003 C00J 118.7(2) . . ?
O009 N003 O002 123.1(3) . . ?
O009 N003 C00J 118.2(3) . . ?
C00D N004 C00M 107.0(2) . . ?
C00D N004 C00O 124.2(2) . . ?
C00M N004 C00O 128.7(3) . . ?
O008 N005 C00M 116.2(3) . . ?
O00B N005 O008 123.9(3) . . ?
O00B N005 C00M 119.9(3) . . ?
O007 N006 C00K 118.0(2) . . ?
O00A N006 O007 122.8(3) . . ?
O00A N006 C00K 119.2(2) . . ?
O00E N00C C00L 116.8(3) . . ?
O00G N00C O00E 124.3(3) . . ?
O00G N00C C00L 118.9(3) . . ?
N004 C00D C00F 123.3(2) . . ?
N004 C00D C00J 107.6(2) . . ?
C00J C00D C00F 128.7(3) . . ?
N001 C00F C00D 123.1(2) . . ?
N001 C00F C00K 107.0(2) . . ?
C00K C00F C00D 129.9(2) . . ?
C00K C00H H00H 127.4 . . ?
C00L C00H H00H 127.4 . . ?
C00L C00H C00K 105.2(2) . . ?
C00J C00I H00I 127.3 . . ?
C00M C00I H00I 127.3 . . ?
C00M C00I C00J 105.3(2) . . ?
C00D C00J N003 125.7(3) . . ?
C00D C00J C00I 108.8(3) . . ?
C00I C00J N003 125.5(2) . . ?
C00F C00K N006 125.8(2) . . ?
C00F C00K C00H 109.1(2) . . ?
C00H C00K N006 125.1(2) . . ?
N001 C00L N00C 123.2(3) . . ?
C00H C00L N001 111.0(2) . . ?
C00H C00L N00C 125.6(3) . . ?
N004 C00M N005 122.9(3) . . ?
C00I C00M N004 111.2(2) . . ?
C00I C00M N005 125.9(3) . . ?
N001 C00N H00A 109.5 . . ?
N001 C00N H00B 109.5 . . ?
N001 C00N H00C 109.5 . . ?
H00A C00N H00B 109.5 . . ?
H00A C00N H00C 109.5 . . ?
H00B C00N H00C 109.5 . . ?
N004 C00O H00D 109.5 . . ?
N004 C00O H00E 109.5 . . ?
N004 C00O H00F 109.5 . . ?
H00D C00O H00E 109.5 . . ?
H00D C00O H00F 109.5 . . ?
H00E C00O H00F 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
N001 C00F 1.351(3) . ?
N001 C00L 1.373(4) . ?
N001 C00N 1.471(4) . ?
O002 N003 1.227(3) . ?
N003 O009 1.218(3) . ?
N003 C00J 1.424(4) . ?
N004 C00D 1.357(4) . ?
N004 C00M 1.381(3) . ?
N004 C00O 1.473(4) . ?
N005 O008 1.222(4) . ?
N005 O00B 1.215(4) . ?
N005 C00M 1.434(4) . ?
N006 O007 1.223(3) . ?
N006 O00A 1.218(3) . ?
N006 C00K 1.419(4) . ?
N00C O00E 1.216(4) . ?
N00C O00G 1.197(4) . ?
N00C C00L 1.437(4) . ?
C00D C00F 1.464(4) . ?
C00D C00J 1.389(4) . ?
C00F C00K 1.391(4) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.392(4) . ?
C00H C00L 1.348(4) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.397(4) . ?
C00I C00M 1.347(4) . ?
C00N H00A 0.9600 . ?
C00N H00B 0.9600 . ?
C00N H00C 0.9600 . ?
C00O H00D 0.9600 . ?
C00O H00E 0.9600 . ?
C00O H00F 0.9600 . ?
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
N001 C00F C00K N006 179.5(2) . . . . ?
N001 C00F C00K C00H 0.2(3) . . . . ?
O002 N003 C00J C00D 18.1(4) . . . . ?
O002 N003 C00J C00I -160.6(3) . . . . ?
N004 C00D C00F N001 111.6(3) . . . . ?
N004 C00D C00F C00K -70.9(4) . . . . ?
N004 C00D C00J N003 -178.5(2) . . . . ?
N004 C00D C00J C00I 0.4(3) . . . . ?
O007 N006 C00K C00F 174.6(3) . . . . ?
O007 N006 C00K C00H -6.3(4) . . . . ?
O008 N005 C00M N004 -176.4(3) . . . . ?
O008 N005 C00M C00I 2.6(4) . . . . ?
O009 N003 C00J C00D -161.2(3) . . . . ?
O009 N003 C00J C00I 20.1(4) . . . . ?
O00A N006 C00K C00F -5.3(4) . . . . ?
O00A N006 C00K C00H 173.8(3) . . . . ?
O00B N005 C00M N004 4.1(4) . . . . ?
O00B N005 C00M C00I -176.9(3) . . . . ?
C00D N004 C00M N005 178.6(2) . . . . ?
C00D N004 C00M C00I -0.5(3) . . . . ?
C00D C00F C00K N006 1.7(5) . . . . ?
C00D C00F C00K C00H -177.6(3) . . . . ?
O00E N00C C00L N001 -163.2(3) . . . . ?
O00E N00C C00L C00H 21.3(5) . . . . ?
C00F N001 C00L N00C -175.1(3) . . . . ?
C00F N001 C00L C00H 1.0(3) . . . . ?
C00F C00D C00J N003 8.7(4) . . . . ?
C00F C00D C00J C00I -172.4(2) . . . . ?
O00G N00C C00L N001 17.8(5) . . . . ?
O00G N00C C00L C00H -157.6(4) . . . . ?
C00J C00D C00F N001 -76.5(4) . . . . ?
C00J C00D C00F C00K 100.9(4) . . . . ?
C00J C00I C00M N004 0.8(3) . . . . ?
C00J C00I C00M N005 -178.3(3) . . . . ?
C00K C00H C00L N001 -0.8(3) . . . . ?
C00K C00H C00L N00C 175.1(3) . . . . ?
C00L N001 C00F C00D 177.2(2) . . . . ?
C00L N001 C00F C00K -0.7(3) . . . . ?
C00L C00H C00K N006 -178.9(3) . . . . ?
C00L C00H C00K C00F 0.4(3) . . . . ?
C00M N004 C00D C00F 173.4(2) . . . . ?
C00M N004 C00D C00J 0.1(3) . . . . ?
C00M C00I C00J N003 178.1(3) . . . . ?
C00M C00I C00J C00D -0.7(3) . . . . ?
C00N N001 C00F C00D -7.6(4) . . . . ?
C00N N001 C00F C00K 174.4(3) . . . . ?
C00N N001 C00L N00C 10.0(5) . . . . ?
C00N N001 C00L C00H -173.9(3) . . . . ?
C00O N004 C00D C00F -9.0(4) . . . . ?
C00O N004 C00D C00J 177.6(3) . . . . ?
C00O N004 C00M N005 1.2(4) . . . . ?
C00O N004 C00M C00I -178.0(3) . . . . ?
