#------------------------------------------------------------------------------
#$Date: 2026-03-04 00:30:15 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304698 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/55/7135513.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_7135513
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         'C8 H6 N4 O4'
_chemical_formula_sum            'C8 H6 N4 O4'
_chemical_formula_weight         222.17
_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     iterative
_audit_creation_date             2025-11-06
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2025-11-17 deposited with the CCDC.	2025-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.051(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5856(7)
_cell_length_b                   20.0958(19)
_cell_length_c                   6.9138(7)
_cell_measurement_reflns_used    6717
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.11
_cell_volume                     909.89(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      295.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_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  0.0544
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16399
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         3.132
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1657 before and 0.0747 after correction.
The Ratio of minimum to maximum transmission is 0.8620.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0992
_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)+(0.1494P)²+2.0788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3013
_refine_ls_wR_factor_ref         0.3079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1622
_reflns_number_total             2069
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc06662j2.cif
_cod_data_source_block           VSP-C3
_cod_database_code               7135513
_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   0.987
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N004(H004), C005(H005), C00C(H00C), C00D(H00D), N2(H2), C00G(H00G)
;
_olex2_submission_original_sample_id compound-3
_olex2_submission_special_instructions 'No special instructions were received'
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
O001 O 0.3936(4) 0.19937(15) 0.4974(5) 0.0461(8) Uani 1 1 d . . . . .
O002 O 0.4107(4) 0.30432(15) 0.5599(5) 0.0451(8) Uani 1 1 d . . . . .
N003 N 0.4867(4) 0.24836(16) 0.5701(5) 0.0318(7) Uani 1 1 d . . . . .
N004 N 1.0003(4) 0.25010(16) 0.7908(5) 0.0316(8) Uani 1 1 d . . . . .
H004 H 1.114531 0.267400 0.837325 0.038 Uiso 1 1 calc R . . . .
C005 C 0.6770(5) 0.39797(17) 0.7195(6) 0.0283(8) Uani 1 1 d . . . . .
H005 H 0.541706 0.384015 0.701670 0.034 Uiso 1 1 calc R . . . .
C006 C 0.8328(5) 0.28577(18) 0.7255(5) 0.0273(8) Uani 1 1 d . . . . .
O1 O 0.4155(5) 0.4994(2) 0.7235(9) 0.0896(17) Uani 1 1 d . . . . .
C008 C 0.6860(5) 0.23786(18) 0.6615(5) 0.0290(8) Uani 1 1 d . . . . .
C009 C 0.8430(5) 0.35781(19) 0.7308(5) 0.0306(8) Uani 1 1 d . . . . .
N1 N 0.5981(6) 0.5140(2) 0.7371(8) 0.0633(14) Uani 1 1 d . . . . .
O00B O 0.6592(6) 0.57129(18) 0.7471(9) 0.095(2) Uani 1 1 d . . . . .
C00C C 0.7709(6) 0.17370(19) 0.6945(6) 0.0351(9) Uani 1 1 d . . . . .
H00C H 0.705999 0.133159 0.667230 0.042 Uiso 1 1 calc R . . . .
C00D C 0.9657(6) 0.18320(19) 0.7737(6) 0.0352(9) Uani 1 1 d . . . . .
H00D H 1.059907 0.149862 0.810325 0.042 Uiso 1 1 calc R . . . .
C00E C 0.7414(6) 0.4619(2) 0.7385(8) 0.0439(11) Uani 1 1 d . . . . .
N2 N 1.0144(6) 0.3983(2) 0.7574(8) 0.0600(12) Uani 1 1 d . . . . .
H2 H 1.139205 0.384971 0.769187 0.072 Uiso 1 1 calc R . . . .
C00G C 0.9497(6) 0.4641(2) 0.7619(8) 0.0490(12) Uani 1 1 d . . . . .
H00G H 1.031551 0.501786 0.777574 0.059 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
O001 N003 C008 117.4(3) . . ?
O002 N003 O001 121.5(3) . . ?
O002 N003 C008 121.0(3) . . ?
C006 N004 C00D 111.7(3) . . ?
C009 C005 C00E 108.5(3) . . ?
N004 C006 C008 104.6(3) . . ?
N004 C006 C009 119.1(3) . . ?
C008 C006 C009 136.2(3) . . ?
N003 C008 C00C 122.8(3) . . ?
C006 C008 N003 128.1(3) . . ?
C006 C008 C00C 109.1(3) . . ?
C005 C009 C006 124.0(3) . . ?
C005 C009 N2 107.4(4) . . ?
N2 C009 C006 128.6(3) . . ?
O1 N1 C00E 118.0(4) . . ?
O00B N1 O1 123.0(4) . . ?
O00B N1 C00E 119.0(4) . . ?
C00D C00C C008 106.2(3) . . ?
C00C C00D N004 108.4(3) . . ?
C005 C00E N1 120.1(4) . . ?
C005 C00E C00G 110.0(4) . . ?
C00G C00E N1 129.8(4) . . ?
C009 N2 C00G 108.3(4) . . ?
C00E C00G N2 105.9(4) . . ?
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
O001 N003 1.238(4) . ?
O002 N003 1.230(4) . ?
N003 C008 1.411(4) . ?
N004 C006 1.352(4) . ?
N004 C00D 1.367(5) . ?
C005 C009 1.354(5) . ?
C005 C00E 1.355(5) . ?
C006 C008 1.403(5) . ?
C006 C009 1.450(5) . ?
O1 N1 1.232(5) . ?
C008 C00C 1.414(5) . ?
C009 N2 1.388(5) . ?
N1 O00B 1.218(5) . ?
N1 C00E 1.410(6) . ?
C00C C00D 1.354(6) . ?
C00E C00G 1.365(6) . ?
N2 C00G 1.390(6) . ?
