#------------------------------------------------------------------------------
#$Date: 2025-08-23 01:35:05 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240367.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_7240367
loop_
_publ_author_name
'He, Xinrui'
'Zhao, Jian'
'Tan, Zeqing'
'Zhao, Jiaxin'
'Cheng, Xiao'
'Zhou, Chuanjian'
_publ_section_title
;
 Chalcone single crystals with red emission and
 photodimerization-triggered hopping behavior: the substituent effect and
 molecular packing effect
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00404A
_journal_year                    2020
_chemical_formula_moiety         'C18 H16 I N O'
_chemical_formula_sum            'C18 H16 I N O'
_chemical_formula_weight         389.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-13 deposited with the CCDC.	2020-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                96.102(5)
_cell_angle_beta                 104.127(4)
_cell_angle_gamma                93.993(5)
_cell_formula_units_Z            2
_cell_length_a                   6.8569(3)
_cell_length_b                   9.5546(6)
_cell_length_c                   12.4049(6)
_cell_measurement_reflns_used    4731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6860
_cell_measurement_theta_min      5.5400
_cell_volume                     779.80(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.972
_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   -117.00 -91.00   1.00    0.10    --  -48.45 -35.00 112.00   26
  2  ω    -79.00 -36.00   1.00    0.10    --  -48.45 -35.00 112.00   43
  3  ω    -25.00   5.00   1.00    0.10    --   48.45 -35.00 112.00   30
  4  ω     44.00 122.00   1.00    0.10    --   48.45  35.00 -91.00   78
  5  ω    -99.00 -73.00   1.00    0.90    --  -86.25 -35.00 112.00   26
  6  ω   -160.00-105.00   1.00    0.90    --  -86.25 -35.00 112.00   55
  7  ω     94.00 151.00   1.00    0.90    --  106.49  35.00 -91.00   57
  8  ω     69.00 118.00   1.00    0.90    --  106.49 -35.00 112.00   49
  9  ω    -41.00  12.00   1.00    0.10    --  -48.45  35.00 -91.00   53
 10  ω     35.00  95.00   1.00    0.10    --   48.45-125.00 -30.00   60
 11  ω    -97.00 -13.00   1.00    0.90    --  -86.25  77.00  60.00   84
 12  ω    -98.00 -21.00   1.00    0.90    --  -86.25  35.00 -91.00   77
 13  ω     35.00 122.00   1.00    0.90    --  106.49 -77.00-180.00   87
 14  ω     76.00 115.00   1.00    0.90    --  106.49 -19.00 -90.00   39
 15  ω     32.00  71.00   1.00    0.90    --  106.49 -19.00 -90.00   39
 16  ω     36.00 117.00   1.00    0.90    --  106.49-125.00 150.00   81
 17  ω     37.00 109.00   1.00    0.90    --  106.49 -99.00 150.00   72
 18  ω    136.00 177.00   1.00    0.90    --  106.49  19.00 -30.00   41
 19  ω    101.00 133.00   1.00    0.90    --  106.49  19.00 -30.00   32
 20  ω     36.00  81.00   1.00    0.90    --  106.49 -38.00 -60.00   45
 21  ω     86.00 112.00   1.00    0.90    --  106.49 -38.00 -60.00   26
 22  ω     41.00 102.00   1.00    0.90    --  106.49 -99.00 -60.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1745645000
_diffrn_orient_matrix_UB_12      0.0182316000
_diffrn_orient_matrix_UB_13      0.0567644000
_diffrn_orient_matrix_UB_21      -0.0165510000
_diffrn_orient_matrix_UB_22      -0.1594789000
_diffrn_orient_matrix_UB_23      0.0100312000
_diffrn_orient_matrix_UB_31      0.1531711000
_diffrn_orient_matrix_UB_32      0.0281004000
_diffrn_orient_matrix_UB_33      0.1155333000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.972
_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       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6316
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         5.588
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    16.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0306
_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)+(0.0370P)²+0.4458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2470
_reflns_number_total             2749
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00404a5.cif
_cod_data_source_block           190717zcj4
_cod_database_code               7240367
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         ICNO
_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 98.54
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.562
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
I1 I 0.03233(4) 0.84006(3) -0.16485(2) 0.07484(13) Uani 1 1 d . . . . .
O1 O 0.9248(4) 0.6308(4) 0.1931(3) 0.0784(8) Uani 1 1 d . . . . .
N1 N 0.4628(5) 0.1387(4) 0.6281(3) 0.0686(8) Uani 1 1 d . . . . .
C1 C 0.6225(4) 0.5295(3) 0.2358(3) 0.0474(7) Uani 1 1 d . . . . .
C2 C 0.2344(5) 0.6791(4) 0.0231(3) 0.0496(7) Uani 1 1 d . . . . .
H2 H 0.1025 0.6498 0.0237 0.060 Uiso 1 1 calc R . . . .
C3 C 0.3987(4) 0.6341(3) 0.0960(2) 0.0434(6) Uani 1 1 d . . . . .
C4 C 0.5938(5) 0.6789(3) 0.0927(3) 0.0470(7) Uani 1 1 d . . . . .
C5 C 0.3994(4) 0.5385(3) 0.1852(3) 0.0468(7) Uani 1 1 d . . . . .
H5A H 0.3305 0.4459 0.1528 0.056 Uiso 1 1 calc R . . . .
H5B H 0.3349 0.5789 0.2411 0.056 Uiso 1 1 calc R . . . .
C6 C 0.6434(4) 0.3794(3) 0.3958(3) 0.0480(7) Uani 1 1 d . . . . .
C7 C 0.7395(5) 0.6152(4) 0.1765(3) 0.0530(7) Uani 1 1 d . . . . .
C8 C 0.7171(5) 0.4634(4) 0.3209(3) 0.0520(7) Uani 1 1 d . . . . .
H8 H 0.8571 0.4736 0.3344 0.062 Uiso 1 1 calc R . . . .
C9 C 0.5214(5) 0.2161(3) 0.5520(3) 0.0523(7) Uani 1 1 d . . . . .
C10 C 0.3805(5) 0.2674(4) 0.4671(3) 0.0518(7) Uani 1 1 d . . . . .
H10 H 0.2434 0.2472 0.4613 0.062 Uiso 1 1 calc R . . . .
C11 C 0.6306(5) 0.7713(4) 0.0196(3) 0.0579(8) Uani 1 1 d . . . . .
H11 H 0.7624 0.8021 0.0199 0.070 Uiso 1 1 calc R . . . .
C12 C 0.4390(5) 0.3468(4) 0.3923(3) 0.0517(7) Uani 1 1 d . . . . .
H12 H 0.3405 0.3799 0.3379 0.062 Uiso 1 1 calc R . . . .
C13 C 0.2746(5) 0.7696(4) -0.0509(3) 0.0520(7) Uani 1 1 d . . . . .
C14 C 0.4698(6) 0.8170(4) -0.0535(3) 0.0606(8) Uani 1 1 d . . . . .
H14 H 0.4911 0.8784 -0.1038 0.073 Uiso 1 1 calc R . . . .
C15 C 0.7257(5) 0.2507(4) 0.5576(3) 0.0609(9) Uani 1 1 d . . . . .
H15 H 0.8246 0.2206 0.6136 0.073 Uiso 1 1 calc R . . . .
C16 C 0.7818(5) 0.3284(4) 0.4814(3) 0.0599(8) Uani 1 1 d . . . . .
H16 H 0.9189 0.3481 0.4871 0.072 Uiso 1 1 calc R . . . .
C17 C 0.2543(7) 0.0946(5) 0.6175(4) 0.0780(11) Uani 1 1 d . . . . .
H17A H 0.1785 0.1755 0.6128 0.117 Uiso 1 1 calc GR . . . .
H17B H 0.2415 0.0503 0.6817 0.117 Uiso 1 1 calc GR . . . .
H17C H 0.2031 0.0286 0.5509 0.117 Uiso 1 1 calc GR . . . .
C18 C 0.6088(8) 0.0733(5) 0.7074(4) 0.0814(12) Uani 1 1 d . . . . .
H18A H 0.6465 -0.0096 0.6697 0.122 Uiso 1 1 calc GR . . . .
H18B H 0.5501 0.0470 0.7661 0.122 Uiso 1 1 calc GR . . . .
H18C H 0.7264 0.1390 0.7391 0.122 Uiso 1 1 calc GR . . . .
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'
I I -0.3257 6.8362 '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
C9 N1 C17 121.3(3) . . ?
C9 N1 C18 121.1(4) . . ?
C17 N1 C18 116.3(4) . . ?
C7 C1 C5 108.3(3) . . ?
C8 C1 C5 131.1(3) . . ?
C8 C1 C7 120.5(3) . . ?
C13 C2 C3 117.4(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 C5 128.6(3) . . ?
C4 C3 C5 111.3(3) . . ?
C3 C4 C7 109.5(3) . . ?
C11 C4 C3 121.6(3) . . ?
C11 C4 C7 128.9(3) . . ?
C3 C5 C1 103.5(2) . . ?
C12 C6 C8 125.1(3) . . ?
C16 C6 C8 119.3(3) . . ?
C16 C6 C12 115.5(3) . . ?
O1 C7 C1 126.8(3) . . ?
O1 C7 C4 125.9(3) . . ?
C4 C7 C1 107.3(3) . . ?
C1 C8 C6 132.4(3) . . ?
N1 C9 C10 121.9(3) . . ?
N1 C9 C15 121.4(3) . . ?
C15 C9 C10 116.7(3) . . ?
C12 C10 C9 121.9(3) . . ?
C14 C11 C4 119.2(3) . . ?
C10 C12 C6 121.8(3) . . ?
C2 C13 I1 119.3(2) . . ?
C2 C13 C14 123.0(3) . . ?
C14 C13 I1 117.8(3) . . ?
C11 C14 C13 118.8(3) . . ?
C16 C15 C9 120.8(3) . . ?
C15 C16 C6 123.3(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
I1 C13 2.103(3) . ?
O1 C7 1.232(4) . ?
N1 C9 1.375(5) . ?
N1 C17 1.432(6) . ?
N1 C18 1.449(5) . ?
C1 C5 1.517(4) . ?
C1 C7 1.476(5) . ?
C1 C8 1.341(5) . ?
C2 C3 1.387(5) . ?
C2 C13 1.387(5) . ?
C3 C4 1.388(4) . ?
C3 C5 1.507(4) . ?
C4 C7 1.471(5) . ?
C4 C11 1.384(5) . ?
C6 C8 1.447(5) . ?
C6 C12 1.403(4) . ?
C6 C16 1.396(5) . ?
C9 C10 1.400(5) . ?
C9 C15 1.400(5) . ?
C10 C12 1.374(5) . ?
C11 C14 1.375(6) . ?
C13 C14 1.392(5) . ?
C15 C16 1.370(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 56966335
