#------------------------------------------------------------------------------
#$Date: 2021-12-04 04:46:23 +0200 (Sat, 04 Dec 2021) $
#$Revision: 271105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/55/1565525.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_1565525
loop_
_publ_author_name
'Chen, Ye-Tao'
'Chen, Wenbin'
'He, Jiaxing'
'Zhang, Guohui'
'Wen, Xinyi'
'Ran, Shuping'
'Deng, Ziqi'
'Zhu, Sheng'
'Li, Hailin'
'Ni, Shaofei'
'Chen, Shunli'
'Dang, Li'
'Li, Ming-De'
_publ_section_title
;
 Tailormade Nonradiative Rotation Tuning of the Near-Infrared Photothermal
 Conversion in Donor--Acceptor Cocrystals
;
_journal_issue                   46
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_page_first              25462
_journal_page_last               25469
_journal_paper_doi               10.1021/acs.jpcc.1c09151
_journal_volume                  125
_journal_year                    2021
_chemical_formula_moiety         'C16 H10, C6 N4'
_chemical_formula_sum            'C22 H10 N4'
_chemical_formula_weight         330.34
_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             2021-03-22
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.458(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.97980(10)
_cell_length_b                   7.25230(10)
_cell_length_c                   14.3587(2)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    299.98(10)
_cell_measurement_theta_max      73.7040
_cell_measurement_theta_min      3.0890
_cell_volume                     830.201(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -22.00   5.00   0.50    0.50    --    0.00 -19.00  60.00   54
  2  ω    -48.00 -14.00   0.50    0.50    --    0.00 -57.00 -60.00   68
  3  ω    -74.00  21.00   0.50    0.50    --    0.00 -57.00   0.00  190
  4  ω    -76.00 -39.00   0.50    0.50    --    0.00 -19.00  60.00   74
  5  ω    123.00 185.00   0.50    0.50    --   95.80  45.00 120.00  124
  6  ω      8.00  75.00   0.50    0.50    --   95.80 -15.00 -30.00  134
  7  ω     69.00 113.00   0.50    0.50    --   95.80 -77.00  60.00   88
  8  ω    126.00 184.00   0.50    0.50    --   95.80  77.00-120.00  116
  9  ω     59.00 125.00   0.50    0.50    --   95.80 -82.00 -90.00  132
 10  ω     76.00 102.00   0.50    0.50    --   95.80  45.00 120.00   52
 11  ω     70.00 111.00   0.50    0.50    --   95.80  77.00-120.00   82
 12  ω     13.00 107.00   0.50    0.50    --   95.80 -15.00 150.00  188
 13  ω     56.00 120.00   0.50    0.50    --   95.80 -77.00 120.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356886000
_diffrn_orient_matrix_UB_12      -0.2001079000
_diffrn_orient_matrix_UB_13      -0.0307036000
_diffrn_orient_matrix_UB_21      0.0099114000
_diffrn_orient_matrix_UB_22      0.0583403000
_diffrn_orient_matrix_UB_23      -0.1027403000
_diffrn_orient_matrix_UB_31      0.1898219000
_diffrn_orient_matrix_UB_32      -0.0407676000
_diffrn_orient_matrix_UB_33      0.0042743000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4199
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.065
_diffrn_reflns_theta_min         5.549
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       Block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0578
_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)+(0.0815P)²+0.2262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1491
_reflns_number_total             1629
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c09151_si_003.cif
_cod_data_source_block           20210126a
_cod_database_code               1565525
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'N H C'
_chemical_oxdiff_usercomment     'N H C'
_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 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C8(H8), C7(H7)
;
_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 2.090
_oxdiff_exptl_absorpt_empirical_full_min 0.490
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
C15 C 0.05375(16) 0.4443(2) 0.52887(9) 0.0422(4) Uani 1 1 d . . . . .
C9 C 0.10777(17) 0.5082(2) 0.61910(10) 0.0483(4) Uani 1 1 d . . . . .
C12 C 0.10656(18) 0.2693(2) 0.49727(11) 0.0480(4) Uani 1 1 d . . . . .
N3 N 0.4917(2) 0.8030(3) 0.64042(13) 0.0780(5) Uani 1 1 d . . . . .
N4 N 0.7165(2) 0.2551(3) 0.62122(13) 0.0767(5) Uani 1 1 d . . . . .
C10 C 0.0515(2) 0.6853(3) 0.64883(12) 0.0587(5) Uani 1 1 d . . . . .
H10 H 0.086147 0.728563 0.707515 0.070 Uiso 1 1 calc R U . . .
C11 C -0.0502(2) 0.7905(3) 0.59396(13) 0.0574(5) Uani 1 1 d . . . . .
H11 H -0.084741 0.904581 0.615635 0.069 Uiso 1 1 calc R U . . .
C13 C 0.2112(2) 0.1617(2) 0.55629(13) 0.0591(5) Uani 1 1 d . . . . .
H13 H 0.245993 0.046284 0.536520 0.071 Uiso 1 1 calc R U . . .
C8 C 0.2140(2) 0.3962(3) 0.67435(11) 0.0595(5) Uani 1 1 d . . . . .
H8 H 0.252111 0.437435 0.732812 0.071 Uiso 1 1 calc R U . . .
C6 C 0.6356(2) 0.3644(3) 0.58513(12) 0.0577(5) Uani 1 1 d . . . . .
C4 C 0.5335(2) 0.5093(3) 0.54268(12) 0.0591(5) Uani 1 1 d . . . . .
C5 C 0.5070(2) 0.6768(3) 0.59551(13) 0.0589(5) Uani 1 1 d . . . . .
C7 C 0.2632(2) 0.2251(3) 0.64343(13) 0.0633(5) Uani 1 1 d . . . . .
H7 H 0.332232 0.151685 0.681808 0.076 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'
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
C15 C15 C9 119.84(17) 3_566 . ?
C12 C15 C15 120.19(16) . 3_566 ?
C12 C15 C9 119.97(14) . . ?
C15 C9 C10 118.45(14) . . ?
C8 C9 C15 118.67(15) . . ?
C8 C9 C10 122.89(15) . . ?
C15 C12 C11 118.50(14) . 3_566 ?
C13 C12 C15 118.86(15) . . ?
C13 C12 C11 122.65(16) . 3_566 ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.57(15) . . ?
C11 C10 H10 119.2 . . ?
C12 C11 H11 119.3 3_566 . ?
C10 C11 C12 121.45(16) . 3_566 ?
C10 C11 H11 119.3 . . ?
C12 C13 H13 119.6 . . ?
C7 C13 C12 120.71(17) . . ?
C7 C13 H13 119.6 . . ?
C9 C8 H8 119.5 . . ?
C7 C8 C9 120.95(16) . . ?
C7 C8 H8 119.5 . . ?
N4 C6 C4 177.4(2) . . ?
C6 C4 C5 118.62(15) . . ?
C4 C4 C6 120.9(2) 3_666 . ?
C4 C4 C5 120.4(2) 3_666 . ?
N3 C5 C4 176.2(2) . . ?
C13 C7 C8 120.84(16) . . ?
C13 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
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
C15 C15 1.419(3) 3_566 ?
C15 C9 1.425(2) . ?
C15 C12 1.418(2) . ?
C9 C10 1.431(2) . ?
C9 C8 1.397(2) . ?
C12 C11 1.434(2) 3_566 ?
C12 C13 1.401(2) . ?
N3 C5 1.129(3) . ?
N4 C6 1.133(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.344(3) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C13 C7 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.380(3) . ?
C6 C4 1.448(2) . ?
C4 C4 1.323(3) 3_666 ?
C4 C5 1.453(3) . ?
C7 H7 0.9300 . ?
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
C15 C15 C9 C10 -0.2(2) 3_566 . . . ?
C15 C15 C9 C8 -179.78(15) 3_566 . . . ?
C15 C15 C12 C11 0.6(2) 3_566 . . 3_566 ?
C15 C15 C12 C13 -179.30(15) 3_566 . . . ?
C15 C9 C10 C11 0.1(2) . . . . ?
C15 C9 C8 C7 -1.4(2) . . . . ?
C15 C12 C13 C7 -0.5(2) . . . . ?
C9 C15 C12 C11 -179.85(13) . . . 3_566 ?
C9 C15 C12 C13 0.3(2) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . 3_566 ?
C9 C8 C7 C13 1.2(3) . . . . ?
C12 C15 C9 C10 -179.78(13) . . . . ?
C12 C15 C9 C8 0.6(2) . . . . ?
C12 C13 C7 C8 -0.3(3) . . . . ?
C10 C9 C8 C7 179.04(16) . . . . ?
C11 C12 C13 C7 179.66(16) 3_566 . . . ?
C8 C9 C10 C11 179.71(17) . . . . ?
