#------------------------------------------------------------------------------
#$Date: 2021-12-04 04:47:06 +0200 (Sat, 04 Dec 2021) $
#$Revision: 271107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/55/1565527.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_1565527
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         'C10 H2 N4, C16 H10'
_chemical_formula_sum            'C26 H12 N4'
_chemical_formula_weight         380.40
_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                 101.465(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0091(4)
_cell_length_b                   9.4292(5)
_cell_length_c                   13.9875(8)
_cell_measurement_reflns_used    4901
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8460
_cell_measurement_theta_min      5.6630
_cell_volume                     905.99(9)
_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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     49.00  87.00   0.50    0.58    --    0.00  57.00 120.00   76
  2  ω    -16.00  69.00   0.50    0.58    --    0.00  40.00-160.00  170
  3  ω    -13.00  45.00   0.50    0.58    --    0.00  38.00 -90.00  116
  4  ω    -83.00 -58.00   0.50    0.58    --    0.00 -38.00 150.00   50
  5  ω    -21.00  39.00   0.50    0.58    --    0.00  57.00 120.00  120
  6  ω     52.00  78.00   0.50    0.58    --    0.00  38.00 -90.00   52
  7  ω     72.00 185.00   0.50    2.32    --   95.80  15.00-180.00  226
  8  ω     29.00  92.00   0.50    2.32    --   95.80 -61.00-150.00  126
  9  ω      9.00 112.00   0.50    2.32    --   95.80 -30.00 150.00  206
 10  ω     75.00 101.00   0.50    2.32    --   95.80 -82.00   0.00   52
 11  ω     29.00 126.00   0.50    2.32    --   95.80 -82.00-150.00  194
 12  ω      6.00  96.00   0.50    2.32    --   95.80 -61.00  60.00  180
 13  ω     15.00 115.00   0.50    2.32    --   95.80 -45.00 -90.00  200
 14  ω     11.00  38.00   0.50    2.32    --   95.80 -30.00   0.00   54
 15  ω     76.00 102.00   0.50    2.32    --   95.80 -82.00 150.00   52
 16  ω     13.00 125.00   0.50    2.32    --   95.80 -82.00  60.00  224
 17  ω     80.00 123.00   0.50    2.32    --   95.80 -82.00 -90.00   86
 18  ω      7.00 115.00   0.50    2.32    --   95.80 -61.00 -90.00  216
 19  ω      7.00  35.00   0.50    2.32    --   95.80 -82.00 -90.00   56
 20  ω     75.00 100.00   0.50    2.32    --   95.80 -30.00   0.00   50
 21  ω     89.00 115.00   0.50    2.32    --   95.80 -82.00  90.00   52
 22  ω     32.00 109.00   0.50    2.32    --   95.80 -30.00  60.00  154
 23  ω     85.00 110.00   0.50    2.32    --   95.80 -82.00 -30.00   50
;
_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      0.0526526000
_diffrn_orient_matrix_UB_12      -0.1543750000
_diffrn_orient_matrix_UB_13      0.0304263000
_diffrn_orient_matrix_UB_21      0.1792752000
_diffrn_orient_matrix_UB_22      0.0088126000
_diffrn_orient_matrix_UB_23      -0.0480584000
_diffrn_orient_matrix_UB_31      0.1240527000
_diffrn_orient_matrix_UB_32      0.0528431000
_diffrn_orient_matrix_UB_33      0.0969307000
_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  0.0360
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7803
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.207
_diffrn_reflns_theta_min         5.695
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56343
_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            Orange
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       Stick
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0499
_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)+(0.0996P)²+0.2762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1696
_reflns_number_total             1811
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c09151_si_002.cif
_cod_data_source_block           20201110c
_cod_database_code               1565527
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     'C H N'
_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:
 C8(H8), C12(H12), C3(H3), C1(H1), C13(H13), C2(H2)
;
_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 3.061
_oxdiff_exptl_absorpt_empirical_full_min 0.655
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
N4 N 0.37430(19) 0.60234(14) 0.21842(9) 0.0339(3) Uani 1 1 d . . . . .
N3 N 0.68736(19) 0.11360(13) 0.58769(9) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.45099(18) 0.53178(15) 0.40102(10) 0.0255(3) Uani 1 1 d . . . . .
C16 C 0.96834(18) 0.57151(14) 0.49009(9) 0.0242(3) Uani 1 1 d . . . . .
C6 C 0.63148(19) 0.22371(15) 0.56045(10) 0.0267(3) Uani 1 1 d . . . . .
C14 C 0.89386(19) 0.61554(14) 0.39233(10) 0.0255(3) Uani 1 1 d . . . . .
C11 C 0.97805(19) 0.66999(15) 0.56820(10) 0.0256(3) Uani 1 1 d . . . . .
C10 C 0.4062(2) 0.56847(14) 0.29905(10) 0.0273(3) Uani 1 1 d . . . . .
C8 C 0.51386(19) 0.39532(14) 0.42987(10) 0.0258(3) Uani 1 1 d . . . . .
H8 H 0.521822 0.326087 0.383471 0.031 Uiso 1 1 calc R U . . .
C12 C 1.0550(2) 0.62193(15) 0.66588(10) 0.0274(3) Uani 1 1 d . . . . .
H12 H 1.063609 0.685476 0.717407 0.033 Uiso 1 1 calc R U . . .
C7 C 0.56461(19) 0.36378(15) 0.52891(10) 0.0252(3) Uani 1 1 d . . . . .
C3 C 0.91219(19) 0.80884(15) 0.54723(10) 0.0284(3) Uani 1 1 d . . . . .
H3 H 0.918906 0.874028 0.597686 0.034 Uiso 1 1 calc R U . . .
C1 C 0.82856(19) 0.75554(15) 0.37538(10) 0.0282(3) Uani 1 1 d . . . . .
H1 H 0.778943 0.785169 0.311889 0.034 Uiso 1 1 calc R U . . .
C13 C 1.1151(2) 0.48678(16) 0.68464(10) 0.0276(3) Uani 1 1 d . . . . .
H13 H 1.163317 0.459351 0.748752 0.033 Uiso 1 1 calc R U . . .
C2 C 0.8368(2) 0.85046(15) 0.45170(11) 0.0294(3) Uani 1 1 d . . . . .
H2 H 0.791533 0.942632 0.439023 0.035 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
C8 C9 C10 120.18(12) . . ?
C8 C9 C7 120.52(13) . 3_666 ?
C7 C9 C10 119.28(13) 3_666 . ?
C14 C16 C16 120.09(15) . 3_766 ?
C14 C16 C11 119.89(13) . . ?
C11 C16 C16 120.02(15) . 3_766 ?
N3 C6 C7 178.28(14) . . ?
C16 C14 C13 118.44(13) . 3_766 ?
C1 C14 C16 118.79(13) . . ?
C1 C14 C13 122.75(13) . 3_766 ?
C16 C11 C12 118.33(13) . . ?
C3 C11 C16 119.03(13) . . ?
C3 C11 C12 122.64(12) . . ?
N4 C10 C9 177.45(15) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 C9 119.27(13) . . ?
C7 C8 H8 120.4 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.67(13) . . ?
C13 C12 H12 119.2 . . ?
C9 C7 C6 119.56(12) 3_666 . ?
C8 C7 C9 120.20(13) . 3_666 ?
C8 C7 C6 120.24(12) . . ?
C11 C3 H3 119.6 . . ?
C2 C3 C11 120.75(13) . . ?
C2 C3 H3 119.6 . . ?
C14 C1 H1 119.5 . . ?
C2 C1 C14 121.05(13) . . ?
C2 C1 H1 119.5 . . ?
C14 C13 H13 119.3 3_766 . ?
C12 C13 C14 121.46(13) . 3_766 ?
C12 C13 H13 119.3 . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.47(13) . . ?
C1 C2 H2 119.8 . . ?
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
N4 C10 1.1505(18) . ?
N3 C6 1.1476(18) . ?
C9 C10 1.4404(19) . ?
C9 C8 1.3935(19) . ?
C9 C7 1.409(2) 3_666 ?
C16 C16 1.430(3) 3_766 ?
C16 C14 1.4251(19) . ?
C16 C11 1.4251(19) . ?
C6 C7 1.4410(19) . ?
C14 C1 1.4018(19) . ?
C14 C13 1.438(2) 3_766 ?
C11 C12 1.4388(19) . ?
C11 C3 1.400(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.3923(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.351(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.392(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(2) . ?
C13 H13 0.9300 . ?
C2 H2 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
C9 C8 C7 C9 1.1(2) . . . 3_666 ?
C9 C8 C7 C6 -179.51(11) . . . . ?
C16 C16 C14 C1 178.50(14) 3_766 . . . ?
C16 C16 C14 C13 -0.1(2) 3_766 . . 3_766 ?
C16 C16 C11 C12 0.9(2) 3_766 . . . ?
C16 C16 C11 C3 -178.93(14) 3_766 . . . ?
C16 C14 C1 C2 0.4(2) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
C16 C11 C3 C2 0.5(2) . . . . ?
C14 C16 C11 C12 -179.69(11) . . . . ?
C14 C16 C11 C3 0.5(2) . . . . ?
C14 C1 C2 C3 0.6(2) . . . . ?
C11 C16 C14 C1 -0.97(19) . . . . ?
C11 C16 C14 C13 -179.59(11) . . . 3_766 ?
C11 C12 C13 C14 0.4(2) . . . 3_766 ?
C11 C3 C2 C1 -1.1(2) . . . . ?
C10 C9 C8 C7 177.20(12) . . . . ?
C12 C11 C3 C2 -179.28(12) . . . . ?
C7 C9 C8 C7 -1.2(2) 3_666 . . . ?
C3 C11 C12 C13 178.99(13) . . . . ?
C13 C14 C1 C2 178.95(13) 3_766 . . . ?
