#------------------------------------------------------------------------------
#$Date: 2026-03-04 00:23:26 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304690 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/54/7135498.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_7135498
loop_
_publ_author_name
'Zhang, Ziyi'
'Li, Xi'
'Feng, Yilin'
'Gao, Xin'
'Qi, Yong'
'Yan, Jiaying'
'Zhang, Nuonuo'
_publ_section_title
;
 A facile strategy for π-extended BOPYINs: transformation into
 six-membered BODIPY analogues and their optical properties.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2659
_journal_page_last               2663
_journal_paper_doi               10.1039/d5cc06628j
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-06-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2025-10-29 deposited with the CCDC.	2025-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.1777(2)
_cell_length_b                   19.0358(12)
_cell_length_c                   24.8301(14)
_cell_measurement_reflns_used    4346
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      71.5400
_cell_measurement_theta_min      4.5700
_cell_volume                     2447.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     51.00  77.00   0.50    0.50    --   61.94-125.00   0.00   52
  2  ω     26.00  77.00   0.50    0.50    --   61.94-125.00  30.00  102
  3  ω     28.00  77.00   0.50    0.50    --   61.94-125.00  60.00   98
  4  ω     31.00  76.00   0.50    0.50    --   61.94-125.00  90.00   90
  5  ω     26.00  52.00   0.50    0.50    --   61.94-125.00 150.00   52
  6  ω     47.00  81.00   0.50    0.50    --   71.27-125.00  90.00   68
  7  ω     51.00  84.00   0.50    0.50    --   71.27-125.00  30.00   66
  8  ω     65.00  90.00   0.50    0.50    --   74.13-125.00  30.00   50
  9  ω     63.00  90.00   0.50    0.50    --   74.13-125.00  60.00   54
 10  ω     42.00  73.00   0.50    0.50    --   74.13-125.00   0.00   62
 11  ω     50.00  85.00   0.50    0.50    --   74.13-125.00 -30.00   70
 12  ω     51.00  89.00   0.50    0.50    --   74.13-125.00-180.00   76
 13  ω     27.00  52.00   0.50    0.50    --   14.00  16.00 -57.29   50
 14  ω     57.00  84.00   0.50    0.50    --   61.94  15.00 -60.00   54
 15  ω     55.00  95.00   0.50    0.50    --   61.94  15.00   0.00   80
 16  ω     58.00  84.00   0.50    0.50    --   61.94  15.00  60.00   52
 17  ω     64.00  94.00   0.50    0.50    --   61.94  15.00 120.00   60
 18  ω     62.00  88.00   0.50    0.50    --   61.94  15.00 150.00   52
 19  ω     61.00  86.00   0.50    0.50    --   61.94  15.00  30.00   50
 20  ω     71.00  97.00   0.50    0.50    --   71.27  15.00 120.00   52
 21  ω     62.00  94.00   0.50    0.50    --   61.94  15.00 -90.00   64
 22  ω     57.00  98.00   0.50    0.50    --   61.94  15.00-120.00   82
 23  ω     60.00  88.00   0.50    0.50    --   61.94  15.00-150.00   56
 24  ω     80.00 106.00   0.50    0.50    --   71.27  15.00-150.00   52
 25  ω     67.00 106.00   0.50    0.50    --   74.13  15.00-180.00   78
 26  ω     73.00  99.00   0.50    0.50    --   74.13  15.00-150.00   52
 27  ω     78.00 112.00   0.50    0.50    --   74.13  15.00-120.00   68
 28  ω     69.00 108.00   0.50    0.50    --   74.13  15.00 -60.00   78
 29  ω     77.00 115.00   0.50    0.50    --   74.13  15.00 -30.00   76
 30  ω     68.00 107.00   0.50    0.50    --   74.13  15.00  60.00   78
 31  ω     75.00 103.00   0.50    0.50    --   74.13  15.00  90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0868139000
_diffrn_orient_matrix_UB_12      -0.0683858000
_diffrn_orient_matrix_UB_13      0.0277049000
_diffrn_orient_matrix_UB_21      0.0021595000
_diffrn_orient_matrix_UB_22      -0.0375655000
_diffrn_orient_matrix_UB_23      -0.0550018000
_diffrn_orient_matrix_UB_31      0.2846574000
_diffrn_orient_matrix_UB_32      0.0212130000
_diffrn_orient_matrix_UB_33      -0.0079771000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16744
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.869
_diffrn_reflns_theta_min         4.646
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.413
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.319
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.1024
_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)+(0.0736P)²+4.6778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2277
_refine_ls_wR_factor_ref         0.2328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2153
_reflns_number_total             2344
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc06628j2.cif
_cod_data_source_block           np_bop-oh_auto
_cod_database_code               7135498
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S Cl'
_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   0.938
_shelx_estimated_absorpt_t_min   0.913
_reflns_odcompleteness_completeness 98.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 N2(H2), N1(H1), C2(H2a), C1(H1a), C6(H6), C3(H3), C9(H9), C15(H15), C13(H13),
 C11(H11), C14(H14), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.912
_oxdiff_exptl_absorpt_empirical_full_min 0.375
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
O1 O 0.2622(5) 0.72228(13) 0.71308(10) 0.0281(7) Uani 1 1 d . . . . .
N2 N 0.6647(7) 0.64849(16) 0.67123(13) 0.0286(8) Uani 1 1 d . . . . .
H2 H 0.599763 0.655662 0.703521 0.034 Uiso 1 1 calc R U . . .
N1 N -0.1509(7) 0.81408(16) 0.69986(12) 0.0276(8) Uani 1 1 d . . . . .
H1 H -0.160431 0.790989 0.730495 0.033 Uiso 1 1 calc R U . . .
C2 C -0.2317(8) 0.89142(19) 0.63490(15) 0.0290(9) Uani 1 1 d . . . . .
H2A H -0.306171 0.929124 0.615221 0.035 Uiso 1 1 calc R U . . .
C1 C -0.3082(8) 0.86750(19) 0.68500(16) 0.0292(9) Uani 1 1 d . . . . .
H1A H -0.447880 0.885550 0.705588 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3807(8) 0.72874(19) 0.62118(15) 0.0280(9) Uani 1 1 d . . . . .
H6 H 0.341825 0.748763 0.587079 0.034 Uiso 1 1 calc R U . . .
C3 C -0.0240(8) 0.84958(19) 0.61873(15) 0.0271(9) Uani 1 1 d . . . . .
H3 H 0.067076 0.853234 0.585640 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8661(8) 0.60213(19) 0.66016(15) 0.0266(9) Uani 1 1 d . . . . .
C4 C 0.0256(8) 0.80149(19) 0.65983(15) 0.0268(9) Uani 1 1 d . . . . .
C7 C 0.5794(8) 0.68200(19) 0.62472(15) 0.0268(9) Uani 1 1 d . . . . .
C5 C 0.2272(7) 0.74901(19) 0.66694(14) 0.0259(8) Uani 1 1 d . . . . .
C9 C 0.7691(9) 0.6705(2) 0.52641(16) 0.0322(9) Uani 1 1 d . . . . .
H9 H 0.659434 0.703535 0.509126 0.039 Uiso 1 1 calc R U . . .
C15 C 1.0139(8) 0.55774(19) 0.69033(16) 0.0312(9) Uani 1 1 d . . . . .
H15 H 0.987116 0.553208 0.728018 0.037 Uiso 1 1 calc R U . . .
C8 C 0.7459(8) 0.6554(2) 0.58082(16) 0.0283(9) Uani 1 1 d . . . . .
C12 C 1.1050(8) 0.5695(2) 0.57695(16) 0.0288(9) Uani 1 1 d . . . . .
C13 C 1.2563(8) 0.5235(2) 0.60897(16) 0.0330(10) Uani 1 1 d . . . . .
H13 H 1.389534 0.496282 0.592945 0.040 Uiso 1 1 calc R U . . .
C11 C 1.1256(8) 0.5850(2) 0.52117(16) 0.0332(10) Uani 1 1 d . . . . .
H11 H 1.250950 0.561469 0.499851 0.040 Uiso 1 1 calc R U . . .
C14 C 1.2088(8) 0.5185(2) 0.66366(17) 0.0332(10) Uani 1 1 d . . . . .
H14 H 1.311754 0.487309 0.684404 0.040 Uiso 1 1 calc R U . . .
C17 C 0.9114(8) 0.60717(19) 0.60402(15) 0.0272(9) Uani 1 1 d . . . . .
C10 C 0.9656(9) 0.6340(2) 0.49781(17) 0.0343(10) Uani 1 1 d . . . . .
H10 H 0.987367 0.643912 0.460588 0.041 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C16 N2 H2 124.3 . . ?
C7 N2 H2 124.3 . . ?
C7 N2 C16 111.3(3) . . ?
C1 N1 H1 125.2 . . ?
C1 N1 C4 109.6(3) . . ?
C4 N1 H1 125.2 . . ?
C1 C2 H2A 126.5 . . ?
C1 C2 C3 106.9(3) . . ?
C3 C2 H2A 126.5 . . ?
N1 C1 C2 108.7(4) . . ?
N1 C1 H1A 125.7 . . ?
C2 C1 H1A 125.7 . . ?
C7 C6 H6 118.6 . . ?
C7 C6 C5 122.7(4) . . ?
C5 C6 H6 118.6 . . ?
C2 C3 H3 126.1 . . ?
C4 C3 C2 107.8(3) . . ?
C4 C3 H3 126.1 . . ?
N2 C16 C17 106.0(3) . . ?
C15 C16 N2 134.7(4) . . ?
C15 C16 C17 119.3(4) . . ?
N1 C4 C3 107.0(3) . . ?
N1 C4 C5 120.6(3) . . ?
C3 C4 C5 132.2(4) . . ?
N2 C7 C8 105.6(3) . . ?
C6 C7 N2 126.3(4) . . ?
C6 C7 C8 128.0(4) . . ?
O1 C5 C6 121.8(3) . . ?
O1 C5 C4 119.2(3) . . ?
C6 C5 C4 118.9(3) . . ?
C8 C9 H9 121.7 . . ?
C8 C9 C10 116.6(4) . . ?
C10 C9 H9 121.7 . . ?
C16 C15 H15 121.0 . . ?
C16 C15 C14 117.9(4) . . ?
C14 C15 H15 121.0 . . ?
C9 C8 C7 134.2(4) . . ?
C17 C8 C7 106.4(3) . . ?
C17 C8 C9 119.4(4) . . ?
C13 C12 C11 129.3(4) . . ?
C17 C12 C13 116.2(4) . . ?
C17 C12 C11 114.4(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C15 C14 H14 118.4 . . ?
C13 C14 C15 123.3(4) . . ?
C13 C14 H14 118.4 . . ?
C8 C17 C16 110.6(4) . . ?
C8 C17 C12 125.6(4) . . ?
C12 C17 C16 123.7(4) . . ?
C9 C10 H10 118.3 . . ?
C11 C10 C9 123.5(4) . . ?
C11 C10 H10 118.3 . . ?
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
O1 C5 1.267(4) . ?
N2 H2 0.8800 . ?
N2 C16 1.393(5) . ?
N2 C7 1.391(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.354(5) . ?
N1 C4 1.371(5) . ?
C2 H2A 0.9500 . ?
C2 C1 1.383(5) . ?
C2 C3 1.397(6) . ?
C1 H1A 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.363(6) . ?
C6 C5 1.439(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(5) . ?
C16 C15 1.364(5) . ?
C16 C17 1.417(5) . ?
C4 C5 1.455(5) . ?
C7 C8 1.479(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.387(5) . ?
C9 C10 1.422(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.419(6) . ?
C8 C17 1.381(5) . ?
C12 C13 1.418(6) . ?
C12 C11 1.420(6) . ?
C12 C17 1.404(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.375(6) . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
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
N2 C16 C15 C14 -179.1(4) . . . . ?
N2 C16 C17 C8 0.5(4) . . . . ?
N2 C16 C17 C12 178.5(3) . . . . ?
N2 C7 C8 C9 -176.0(4) . . . . ?
N2 C7 C8 C17 1.5(4) . . . . ?
N1 C4 C5 O1 -10.3(6) . . . . ?
N1 C4 C5 C6 169.5(3) . . . . ?
C2 C3 C4 N1 0.4(4) . . . . ?
C2 C3 C4 C5 -175.1(4) . . . . ?
C1 N1 C4 C3 0.4(4) . . . . ?
C1 N1 C4 C5 176.6(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C6 C7 C8 C9 4.9(7) . . . . ?
C6 C7 C8 C17 -177.6(4) . . . . ?
C3 C2 C1 N1 1.3(4) . . . . ?
C3 C4 C5 O1 164.8(4) . . . . ?
C3 C4 C5 C6 -15.5(6) . . . . ?
C16 N2 C7 C6 177.8(4) . . . . ?
C16 N2 C7 C8 -1.3(4) . . . . ?
C16 C15 C14 C13 0.4(6) . . . . ?
C4 N1 C1 C2 -1.1(4) . . . . ?
C7 N2 C16 C15 180.0(4) . . . . ?
C7 N2 C16 C17 0.6(4) . . . . ?
C7 C6 C5 O1 -2.8(6) . . . . ?
C7 C6 C5 C4 177.5(4) . . . . ?
C7 C8 C17 C16 -1.2(4) . . . . ?
C7 C8 C17 C12 -179.3(4) . . . . ?
C5 C6 C7 N2 -0.9(6) . . . . ?
C5 C6 C7 C8 178.1(4) . . . . ?
C9 C8 C17 C16 176.7(4) . . . . ?
C9 C8 C17 C12 -1.3(6) . . . . ?
C15 C16 C17 C8 -179.1(4) . . . . ?
C15 C16 C17 C12 -1.0(6) . . . . ?
C8 C9 C10 C11 1.0(6) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C12 C11 C10 C9 -1.5(6) . . . . ?
C13 C12 C11 C10 -177.2(4) . . . . ?
C13 C12 C17 C16 1.1(6) . . . . ?
C13 C12 C17 C8 178.9(4) . . . . ?
C11 C12 C13 C14 177.2(4) . . . . ?
C11 C12 C17 C16 -176.9(4) . . . . ?
C11 C12 C17 C8 0.8(6) . . . . ?
C17 C16 C15 C14 0.2(6) . . . . ?
C17 C12 C13 C14 -0.5(6) . . . . ?
C17 C12 C11 C10 0.5(6) . . . . ?
C10 C9 C8 C7 177.6(4) . . . . ?
C10 C9 C8 C17 0.4(6) . . . . ?
