#------------------------------------------------------------------------------
#$Date: 2022-01-04 04:28:20 +0200 (Tue, 04 Jan 2022) $
#$Revision: 271788 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/05/8000563.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_8000563
loop_
_publ_author_name
'Wang, Long'
'Cai, Wanlin'
'Sun, Jing'
'Wu, Yuling'
'Zhang, Bin'
'Tian, Xiangbin'
'Guo, Shaoting'
'Liang, WanZhen'
'Fu, Hongbing'
'Yao, Jiannian'
_publ_section_title
;
 H-Type-like Aggregation-Accelerated Singlet Fission Process in
 Dipyrrolonaphthyridinedione Thin Film: The Role of Charge
 Transfer/Excimer Mixed Intermediate State.
;
_journal_issue                   51
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              12276
_journal_page_last               12282
_journal_paper_doi               10.1021/acs.jpclett.1c03265
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C14 H8 N2 O2'
_chemical_formula_sum            'C14 H8 N2 O2'
_chemical_formula_weight         236.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.592(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6191(2)
_cell_length_b                   3.79700(10)
_cell_length_c                   19.9030(5)
_cell_measurement_reflns_used    3574
_cell_measurement_temperature    170.00(11)
_cell_measurement_theta_max      71.7040
_cell_measurement_theta_min      4.4500
_cell_volume                     498.61(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -119.00 -59.00   1.00    0.20    --  -46.95-143.00-124.00   60
  2  ω   -119.00 -70.00   1.00    0.20    --  -46.95-127.00  45.00   49
  3  ω     26.00 105.00   1.00    0.20    --   46.95-143.00-124.00   79
  4  ω     18.00  96.00   1.00    0.20    --   46.95-127.00  45.00   78
  5  ω   -130.00 -26.00   1.00    0.50    --  -99.00 143.00 -68.00  104
  6  ω     65.00 169.00   1.00    0.50    --  103.25 143.00 -68.00  104
  7  ω   -118.00 -32.00   1.00    0.20    --  -46.95 -57.00  30.00   86
  8  ω   -119.00 -71.00   1.00    0.20    --  -46.95-125.00 150.00   48
  9  ω    -59.00  26.00   1.00    0.20    --  -46.95  38.00 120.00   85
 10  ω   -119.00 -71.00   1.00    0.20    --  -46.95-125.00-150.00   48
 11  ω   -118.00 -26.00   1.00    0.50    --  -99.00 127.00 121.00   92
 12  ω   -113.00 -24.00   1.00    0.50    --  -99.00  15.00 -90.00   89
 13  ω   -112.00 -27.00   1.00    0.50    --  -99.00  45.00 -60.00   85
 14  ω   -168.00 -27.00   1.00    0.50    --  -99.00   0.00 120.00  141
 15  ω   -168.00 -86.00   1.00    0.50    --  -99.00 -30.00 -60.00   82
 16  ω   -122.00 -26.00   1.00    0.50    --  -99.00  77.00 -30.00   96
 17  ω   -112.00 -27.00   1.00    0.50    --  -99.00  45.00 150.00   85
 18  ω   -115.00 -26.00   1.00    0.50    --  -99.00  61.00 150.00   89
 19  ω   -168.00 -81.00   1.00    0.50    --  -99.00 -94.00 150.00   87
 20  ω     31.00 120.00   1.00    0.50    --  103.25 -61.00 -60.00   89
 21  ω     28.00 116.00   1.00    0.50    --  103.25 -30.00   0.00   88
 22  ω   -118.00 -32.00   1.00    0.20    --  -46.95 -57.00-150.00   86
 23  ω   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00  30.00   95
 24  ω   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00 120.00   95
 25  ω   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00-180.00   95
 26  ω   -119.00 -24.00   1.00    0.20    --  -46.95 -77.00 -60.00   95
 27  ω     32.00 118.00   1.00    0.20    --   46.95  57.00  30.00   86
 28  ω     24.00 119.00   1.00    0.20    --   46.95  77.00 120.00   95
 29  ω   -168.00 -86.00   1.00    0.50    --  -99.00 -45.00 150.00   82
 30  ω   -168.00 -86.00   1.00    0.50    --  -99.00 -30.00-120.00   82
 31  ω   -168.00 -82.00   1.00    0.50    --  -99.00 -61.00  60.00   86
 32  ω     87.00 169.00   1.00    0.50    --  103.25  61.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080983000
_diffrn_orient_matrix_UB_12      -0.0473168000
_diffrn_orient_matrix_UB_13      -0.0766150000
_diffrn_orient_matrix_UB_21      -0.0134632000
_diffrn_orient_matrix_UB_22      -0.4023563000
_diffrn_orient_matrix_UB_23      0.0085203000
_diffrn_orient_matrix_UB_31      -0.2329689000
_diffrn_orient_matrix_UB_32      0.0214320000
_diffrn_orient_matrix_UB_33      -0.0094116000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8690
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.928
_diffrn_reflns_theta_min         4.457
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0370
_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)+(0.0410P)²+0.2063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                926
_reflns_number_total             995
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz1c03265_si_002.cif
_cod_data_source_block           tx941
_cod_database_code               8000563
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6)
;
_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 1.499
_oxdiff_exptl_absorpt_empirical_full_min 0.621
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.86299(15) 0.4675(3) 0.60161(5) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.55912(17) 0.7191(3) 0.61854(5) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.3958(2) 0.5480(4) 0.48952(6) 0.0227(3) Uani 1 1 d . . . . .
C2 C 0.2788(2) 0.7187(4) 0.53210(7) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.145928 0.777599 0.517815 0.029 Uiso 1 1 calc R . . . .
C3 C 0.3579(2) 0.8075(4) 0.59812(7) 0.0243(3) Uani 1 1 d . . . . .
C4 C 0.2788(2) 0.9734(4) 0.65163(7) 0.0276(3) Uani 1 1 d . . . . .
H4 H 0.148174 1.062760 0.652330 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4321(2) 0.9833(4) 0.70534(7) 0.0294(3) Uani 1 1 d . . . . .
H5 H 0.419346 1.079336 0.747785 0.035 Uiso 1 1 calc R . . . .
C6 C 0.6018(2) 0.8280(4) 0.68427(7) 0.0279(3) Uani 1 1 d . . . . .
H6 H 0.724754 0.800389 0.709763 0.033 Uiso 1 1 calc R . . . .
C7 C 0.6913(2) 0.5394(4) 0.57909(7) 0.0246(3) Uani 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 0.0181 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
C6 N1 C3 108.71(11) . . ?
C6 N1 C7 126.06(12) . . ?
C7 N1 C3 125.20(11) . . ?
C1 C1 C7 119.99(15) 3_666 3_666 ?
C2 C1 C1 121.04(15) . 3_666 ?
C2 C1 C7 118.97(12) . 3_666 ?
C1 C2 C3 120.41(12) . . ?
N1 C3 C2 118.96(12) . . ?
C4 C3 N1 107.26(12) . . ?
C4 C3 C2 133.78(13) . . ?
C3 C4 C5 107.62(13) . . ?
C6 C5 C4 108.33(13) . . ?
C5 C6 N1 108.06(12) . . ?
O1 C7 N1 120.64(12) . . ?
O1 C7 C1 124.98(13) . 3_666 ?
N1 C7 C1 114.38(12) . 3_666 ?
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 C7 1.2185(17) . ?
N1 C3 1.4016(18) . ?
N1 C6 1.3795(17) . ?
N1 C7 1.3993(18) . ?
C1 C1 1.455(3) 3_666 ?
C1 C2 1.3574(19) . ?
C1 C7 1.4770(19) 3_666 ?
C2 C3 1.4157(18) . ?
C3 C4 1.3764(19) . ?
C4 C5 1.414(2) . ?
C5 C6 1.364(2) . ?
