#------------------------------------------------------------------------------
#$Date: 2022-01-19 12:15:26 +0200 (Wed, 19 Jan 2022) $
#$Revision: 272130 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566044.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_1566044
loop_
_publ_author_name
'Tan, Zeqing'
'Zhao, Jian'
'Sun, Jingzhi'
'Zhao, Jiaxin'
'He, Xinrui'
'Liu, Zhe'
'Zhu, Lin'
'Cheng, Xiao'
'Zhou, Chuanjian'
_publ_section_title
;
 CHCl3-Dependent Emission Color and Jumping Behavior of Cyclic Chalcone
 Single Crystals: The Halogen Bond Network Effect
;
_journal_issue                   5
_journal_name_full               Crystals
_journal_page_first              530
_journal_paper_doi               10.3390/cryst11050530
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C28 H20 Cl N O, 2(C H Cl3)'
_chemical_formula_sum            'C30 H22 Cl7 N O'
_chemical_formula_weight         660.63
_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     direct
_cell_angle_alpha                84.387(12)
_cell_angle_beta                 87.485(12)
_cell_angle_gamma                84.125(12)
_cell_formula_units_Z            2
_cell_length_a                   10.1961(16)
_cell_length_b                   10.8540(16)
_cell_length_c                   14.091(2)
_cell_measurement_reflns_used    2299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3458
_cell_measurement_theta_min      3.4703
_cell_volume                     1542.9(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -41.00   36.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   82.0000  -53.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00   20.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000 -180.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000  120.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0225624000
_diffrn_orient_matrix_UB_12      0.0522534000
_diffrn_orient_matrix_UB_13      0.0184626000
_diffrn_orient_matrix_UB_21      -0.0241998000
_diffrn_orient_matrix_UB_22      0.0386693000
_diffrn_orient_matrix_UB_23      -0.0402402000
_diffrn_orient_matrix_UB_31      -0.0616579000
_diffrn_orient_matrix_UB_32      0.0113307000
_diffrn_orient_matrix_UB_33      0.0245150000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9839
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0841
_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)+(0.1087P)²+1.8663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.2609
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3405
_reflns_number_total             5636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Crystals-2021-11-5-530.cif
_cod_data_source_block           1+2CHCl3
_cod_original_cell_volume        1543.0(4)
_cod_database_code               1566044
_chemical_oxdiff_formula         'c h n o'
_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   0.781
_shelx_estimated_absorpt_t_min   0.749
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl1 Cl 0.31617(15) 0.79684(14) 1.16360(11) 0.0881(5) Uani 1 1 d . . . . .
O1 O 0.7846(3) 0.3001(3) 1.1489(2) 0.0679(10) Uani 1 1 d . . . . .
N1 N 1.1825(4) 0.4747(3) 0.6115(3) 0.0539(9) Uani 1 1 d . . . . .
C1 C 0.5162(5) 0.6787(4) 1.0674(3) 0.0571(11) Uani 1 1 d . . . . .
H1 H 0.502144 0.742860 1.018989 0.068 Uiso 1 1 calc R . . . .
C2 C 0.4404(5) 0.6771(5) 1.1511(3) 0.0596(12) Uani 1 1 d . . . . .
C3 C 0.4573(5) 0.5817(5) 1.2246(3) 0.0618(13) Uani 1 1 d . . . . .
H3 H 0.404290 0.582899 1.279953 0.074 Uiso 1 1 calc R . . . .
C4 C 0.5551(4) 0.4850(5) 1.2133(3) 0.0579(12) Uani 1 1 d . . . . .
H4 H 0.568600 0.420098 1.261121 0.070 Uiso 1 1 calc R . . . .
C5 C 0.6323(4) 0.4863(4) 1.1299(3) 0.0475(10) Uani 1 1 d . . . . .
C6 C 0.6136(4) 0.5819(4) 1.0579(3) 0.0483(10) Uani 1 1 d . . . . .
C7 C 0.7100(4) 0.5638(4) 0.9746(3) 0.0514(11) Uani 1 1 d . . . . .
H7A H 0.664196 0.556892 0.916720 0.062 Uiso 1 1 calc R . . . .
H7B H 0.764833 0.632071 0.963805 0.062 Uiso 1 1 calc R . . . .
C8 C 0.7912(4) 0.4436(4) 1.0055(3) 0.0460(10) Uani 1 1 d . . . . .
C9 C 0.7424(4) 0.3959(4) 1.1012(3) 0.0499(10) Uani 1 1 d . . . . .
C10 C 0.8934(4) 0.3815(4) 0.9618(3) 0.0481(10) Uani 1 1 d . . . . .
H10 H 0.926695 0.308354 0.996218 0.058 Uiso 1 1 calc R . . . .
C11 C 0.9618(4) 0.4080(4) 0.8699(3) 0.0446(9) Uani 1 1 d . . . . .
C12 C 1.0729(4) 0.3304(4) 0.8453(3) 0.0517(11) Uani 1 1 d . . . . .
H12 H 1.099622 0.261824 0.887351 0.062 Uiso 1 1 calc R . . . .
C13 C 1.1445(4) 0.3512(4) 0.7617(3) 0.0531(11) Uani 1 1 d . . . . .
H13 H 1.218207 0.296993 0.748326 0.064 Uiso 1 1 calc R . . . .
C14 C 1.1081(4) 0.4525(4) 0.6965(3) 0.0476(10) Uani 1 1 d . . . . .
C15 C 0.9946(4) 0.5300(4) 0.7188(3) 0.0506(11) Uani 1 1 d . . . . .
H15 H 0.966213 0.596657 0.675634 0.061 Uiso 1 1 calc R . . . .
C16 C 0.9250(4) 0.5092(4) 0.8031(3) 0.0507(11) Uani 1 1 d . . . . .
H16 H 0.851465 0.563488 0.816655 0.061 Uiso 1 1 calc R . . . .
C17 C 1.1809(4) 0.5936(4) 0.5603(3) 0.0503(11) Uani 1 1 d . . . . .
C18 C 1.1772(5) 0.6064(5) 0.4615(3) 0.0632(13) Uani 1 1 d . . . . .
H18 H 1.174832 0.536269 0.428904 0.076 Uiso 1 1 calc R . . . .
C19 C 1.1768(6) 0.7225(6) 0.4108(4) 0.0778(16) Uani 1 1 d . . . . .
H19 H 1.174049 0.729750 0.344593 0.093 Uiso 1 1 calc R . . . .
C20 C 1.1805(6) 0.8256(5) 0.4576(4) 0.0822(17) Uani 1 1 d . . . . .
H20 H 1.179950 0.903405 0.423325 0.099 Uiso 1 1 calc R . . . .
C21 C 1.1851(6) 0.8153(5) 0.5562(4) 0.0756(15) Uani 1 1 d . . . . .
H21 H 1.187266 0.886178 0.588032 0.091 Uiso 1 1 calc R . . . .
C22 C 1.1865(5) 0.6997(4) 0.6073(3) 0.0576(12) Uani 1 1 d . . . . .
H22 H 1.191219 0.692979 0.673401 0.069 Uiso 1 1 calc R . . . .
C23 C 1.2510(4) 0.3728(4) 0.5674(3) 0.0525(11) Uani 1 1 d . . . . .
C24 C 1.1864(6) 0.2751(5) 0.5455(4) 0.0702(14) Uani 1 1 d . . . . .
H24 H 1.097115 0.272878 0.561442 0.084 Uiso 1 1 calc R . . . .
C25 C 1.2547(9) 0.1797(6) 0.4996(4) 0.100(2) Uani 1 1 d . . . . .
H25 H 1.211617 0.112573 0.485546 0.120 Uiso 1 1 calc R . . . .
C26 C 1.3865(10) 0.1842(7) 0.4746(5) 0.111(3) Uani 1 1 d . . . . .
H26 H 1.431674 0.121095 0.442403 0.133 Uiso 1 1 calc R . . . .
C27 C 1.4500(7) 0.2804(8) 0.4970(5) 0.102(2) Uani 1 1 d . . . . .
H27 H 1.538982 0.282928 0.480199 0.122 Uiso 1 1 calc R . . . .
C28 C 1.3844(5) 0.3744(5) 0.5443(4) 0.0712(14) Uani 1 1 d . . . . .
H28 H 1.429391 0.439073 0.560822 0.085 Uiso 1 1 calc R . . . .
Cl2 Cl 1.0329(2) 1.0300(2) 0.7649(2) 0.1469(9) Uani 1 1 d . . . . .
Cl3 Cl 0.8825(4) 0.9118(3) 0.91927(17) 0.2014(18) Uani 1 1 d . . . . .
Cl4 Cl 0.8603(2) 0.8563(2) 0.7268(2) 0.1328(8) Uani 1 1 d . . . . .
C29 C 0.9677(7) 0.8964(6) 0.8111(5) 0.105(2) Uani 1 1 d . . . . .
H29 H 1.039589 0.829559 0.820254 0.126 Uiso 1 1 calc R . . . .
Cl5 Cl 1.3995(3) 0.0498(2) 0.70840(15) 0.1471(10) Uani 1 1 d . . . . .
Cl6 Cl 1.3575(3) 0.0066(3) 0.90937(16) 0.1468(10) Uani 1 1 d . . . . .
Cl7 Cl 1.5315(3) -0.1613(3) 0.8084(2) 0.1688(13) Uani 1 1 d . . . . .
C30 C 1.3997(10) -0.0628(9) 0.8066(6) 0.138(3) Uani 1 1 d . . . . .
H30 H 1.326703 -0.111958 0.796924 0.165 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C14 N1 C17 122.7(3) . .
C14 N1 C23 119.9(3) . .
C17 N1 C23 117.1(3) . .
C2 C1 H1 121.1 . .
C2 C1 C6 117.8(4) . .
C6 C1 H1 121.1 . .
C1 C2 Cl1 118.4(4) . .
C1 C2 C3 122.7(4) . .
C3 C2 Cl1 118.8(4) . .
C2 C3 H3 120.7 . .
C4 C3 C2 118.5(4) . .
C4 C3 H3 120.7 . .
C3 C4 H4 120.4 . .
C5 C4 C3 119.2(4) . .
C5 C4 H4 120.4 . .
C4 C5 C9 129.5(4) . .
C6 C5 C4 121.3(4) . .
C6 C5 C9 109.2(4) . .
C1 C6 C5 120.5(4) . .
C1 C6 C7 127.8(4) . .
C5 C6 C7 111.7(3) . .
C6 C7 H7A 111.1 . .
C6 C7 H7B 111.1 . .
H7A C7 H7B 109.1 . .
C8 C7 C6 103.4(3) . .
C8 C7 H7A 111.1 . .
C8 C7 H7B 111.1 . .
C9 C8 C7 108.8(3) . .
C10 C8 C7 130.8(4) . .
C10 C8 C9 120.4(4) . .
O1 C9 C5 126.0(4) . .
O1 C9 C8 127.1(4) . .
C8 C9 C5 106.9(3) . .
C8 C10 H10 114.2 . .
C8 C10 C11 131.7(4) . .
C11 C10 H10 114.2 . .
C12 C11 C10 119.1(4) . .
C12 C11 C16 116.2(4) . .
C16 C11 C10 124.6(4) . .
C11 C12 H12 118.7 . .
C13 C12 C11 122.6(4) . .
C13 C12 H12 118.7 . .
C12 C13 H13 119.6 . .
C12 C13 C14 120.8(4) . .
C14 C13 H13 119.6 . .
C13 C14 N1 120.7(4) . .
C13 C14 C15 117.5(4) . .
C15 C14 N1 121.7(4) . .
C14 C15 H15 119.4 . .
C16 C15 C14 121.1(4) . .
C16 C15 H15 119.4 . .
C11 C16 H16 119.1 . .
C15 C16 C11 121.7(4) . .
C15 C16 H16 119.1 . .
C18 C17 N1 120.5(4) . .
C18 C17 C22 118.4(4) . .
C22 C17 N1 121.1(4) . .
C17 C18 H18 119.6 . .
C19 C18 C17 120.9(5) . .
C19 C18 H18 119.6 . .
C18 C19 H19 119.9 . .
C20 C19 C18 120.1(5) . .
C20 C19 H19 119.9 . .
C19 C20 H20 119.9 . .
C19 C20 C21 120.2(5) . .
C21 C20 H20 119.9 . .
C20 C21 H21 120.0 . .
C22 C21 C20 120.0(5) . .
C22 C21 H21 120.0 . .
C17 C22 H22 119.8 . .
C21 C22 C17 120.3(5) . .
C21 C22 H22 119.8 . .
C24 C23 N1 121.1(4) . .
C24 C23 C28 119.7(5) . .
C28 C23 N1 119.3(5) . .
C23 C24 H24 120.2 . .
C23 C24 C25 119.7(6) . .
C25 C24 H24 120.2 . .
C24 C25 H25 119.9 . .
C26 C25 C24 120.1(7) . .
C26 C25 H25 119.9 . .
C25 C26 H26 120.0 . .
C27 C26 C25 119.9(6) . .
C27 C26 H26 120.0 . .
C26 C27 H27 119.7 . .
C26 C27 C28 120.7(6) . .
C28 C27 H27 119.7 . .
C23 C28 H28 120.0 . .
C27 C28 C23 119.9(6) . .
C27 C28 H28 120.0 . .
Cl2 C29 Cl3 113.1(4) . .
Cl2 C29 Cl4 107.7(4) . .
Cl2 C29 H29 108.8 . .
Cl3 C29 Cl4 109.5(4) . .
Cl3 C29 H29 108.8 . .
Cl4 C29 H29 108.8 . .
Cl5 C30 H30 105.3 . .
Cl6 C30 Cl5 110.2(5) . .
Cl6 C30 H30 105.3 . .
Cl7 C30 Cl5 112.9(5) . .
Cl7 C30 Cl6 116.8(5) . .
Cl7 C30 H30 105.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.736(5) .
O1 C9 1.230(5) .
N1 C14 1.403(5) .
N1 C17 1.414(5) .
N1 C23 1.427(5) .
C1 H1 0.9300 .
C1 C2 1.381(6) .
C1 C6 1.383(6) .
C2 C3 1.394(7) .
C3 H3 0.9300 .
C3 C4 1.388(6) .
C4 H4 0.9300 .
C4 C5 1.385(6) .
C5 C6 1.383(6) .
C5 C9 1.483(6) .
C6 C7 1.512(6) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C7 C8 1.509(6) .
C8 C9 1.480(6) .
C8 C10 1.342(6) .
C10 H10 0.9300 .
C10 C11 1.462(5) .
C11 C12 1.393(6) .
C11 C16 1.406(6) .
C12 H12 0.9300 .
C12 C13 1.371(6) .
C13 H13 0.9300 .
C13 C14 1.392(6) .
C14 C15 1.402(6) .
C15 H15 0.9300 .
C15 C16 1.368(6) .
C16 H16 0.9300 .
C17 C18 1.388(6) .
C17 C22 1.391(6) .
C18 H18 0.9300 .
C18 C19 1.386(7) .
C19 H19 0.9300 .
C19 C20 1.358(8) .
C20 H20 0.9300 .
C20 C21 1.386(8) .
C21 H21 0.9300 .
C21 C22 1.383(7) .
C22 H22 0.9300 .
C23 C24 1.370(7) .
C23 C28 1.386(7) .
C24 H24 0.9300 .
C24 C25 1.386(8) .
C25 H25 0.9300 .
C25 C26 1.378(11) .
C26 H26 0.9300 .
C26 C27 1.353(11) .
C27 H27 0.9300 .
C27 C28 1.374(9) .
C28 H28 0.9300 .
Cl2 C29 1.716(8) .
Cl3 C29 1.735(7) .
Cl4 C29 1.764(8) .
C29 H29 0.9800 .
Cl5 C30 1.755(8) .
Cl6 C30 1.715(9) .
Cl7 C30 1.629(8) .
C30 H30 0.9800 .
