#------------------------------------------------------------------------------
#$Date: 2026-03-04 04:03:29 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304728 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/67/1576751.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_1576751
loop_
_publ_author_name
'Qi, Jun-Chao'
'Chen, Xiao-Gang'
'Wang, Zhen-Yu'
'Tang, Yuan-Yuan'
'Song, Xian-Jiang'
'Qin, Yan'
'Lv, Hui-Peng'
'Xiong, Ren-Gen'
'Liao, Wei-Qiang'
_publ_section_title
;
 Organic-inorganic perovskite ferroelectric catalytic selective alkyne
 coupling under ultrasound sonication.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1792
_journal_page_last               1800
_journal_paper_doi               10.1039/d5sc07784b
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C16 H8 Cl2'
_chemical_formula_sum            'C16 H8 Cl2'
_chemical_formula_weight         271.12
_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
_audit_creation_date             2025-10-07
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-07 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.301(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.9499(7)
_cell_length_b                   24.878(4)
_cell_length_c                   6.5419(15)
_cell_measurement_reflns_used    1483
_cell_measurement_temperature    299.66(10)
_cell_measurement_theta_max      71.9460
_cell_measurement_theta_min      3.5440
_cell_volume                     642.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.66(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     55.00 121.00   0.50    0.05    --   74.97  15.00 -30.00  132
  2  ω     57.00  83.00   0.50    0.05    --   75.32-125.00 -30.00   52
  3  ω     57.00  87.00   0.50    0.05    --   75.32-114.00  23.00   60
  4  ω     27.00  53.00   0.50    0.05    --   60.40-114.00  23.00   52
  5  ω   -105.00 -78.00   0.50    0.05    --  -60.77 -15.00  90.00   54
  6  ω    -99.00 -69.00   0.50    0.05    --  -75.45 -15.00  60.00   60
  7  ω    -70.00 -44.00   0.50    0.05    --  -60.77 -15.00  90.00   52
  8  ω   -100.00 -49.00   0.50    0.05    --  -60.77 -15.00  30.00  102
  9  ω   -120.00 -75.00   0.50    0.05    --  -75.45 -15.00  30.00   90
 10  ω    -79.00 -49.00   0.50    0.05    --  -60.77 -15.00 -30.00   60
 11  ω   -102.00 -59.00   0.50    0.05    --  -75.45 -15.00 -60.00   86
 12  ω    -96.00 -53.00   0.50    0.05    --  -75.45 125.00 150.00   86
 13  ω    -87.00 -62.00   0.50    0.05    --  -75.45 114.00 114.00   50
 14  ω    -83.00 -33.00   0.50    0.05    --  -73.82 114.00 114.00  100
 15  ω    -49.00 -21.00   0.50    0.05    --  -60.77 114.00 114.00   56
 16  ω    -61.00 -36.00   0.50    0.05    --  -78.89 124.00  29.58   50
 17  ω    -98.00 -43.00   0.50    0.05    --  -78.89 124.00   1.01  110
 18  ω    -99.00 -74.00   0.50    0.05    --  -78.89 124.00  29.58   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1313656000
_diffrn_orient_matrix_UB_12      0.0226130000
_diffrn_orient_matrix_UB_13      0.2075415000
_diffrn_orient_matrix_UB_21      -0.1213426000
_diffrn_orient_matrix_UB_22      0.0565388000
_diffrn_orient_matrix_UB_23      -0.0650465000
_diffrn_orient_matrix_UB_31      -0.3470399000
_diffrn_orient_matrix_UB_32      -0.0112437000
_diffrn_orient_matrix_UB_33      0.0906646000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3359
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         87.422
_diffrn_reflns_theta_min         3.553
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0684P)²+0.2152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                933
_reflns_number_total             1212
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc07784b2.cif
_cod_data_source_block           2g
_cod_database_code               1576751
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H Cl'
_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.
;
_diffrn_oxdiff_digest_hkl
;
4317b0051fb84be5cf993b28e02c1ead2dbb38
;
_reflns_odcompleteness_completeness 98.40
_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:
 C2(H2), C6(H6), C4(H4), C5(H5)
;
_shelx_res_file
;
TITL qjc-3cl_auto_a.res in P2(1)/n
    2g.res
    created by SHELXL-2019/3 at 23:19:31 on 07-Oct-2025
REM Old TITL QJC-3Cl_auto in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.176, Rweak 0.211, Alpha 0.018
REM <I/s> 0.332 for 41 systematic absences, Orientation as input
REM Formula found by SHELXT: C5 Cl
CELL 1.54184 3.9499 24.8776 6.5419 90 92.301 90
ZERR 2 0.0007 0.0043 0.0015 0 0.017 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cl
UNIT 32 16 4

L.S. 4
PLAN  5
TEMP 27
CONF
BOND
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\2g.hkl">
REM </olex2.extras>

WGHT    0.068400    0.215200
FVAR       1.32808
CL9   3    0.277215    0.267008    0.650642    11.00000    0.07658    0.04907 =
         0.09501    0.00917   -0.00629   -0.01135
C1    1    0.672306    0.414332    0.656864    11.00000    0.04612    0.04378 =
         0.05798   -0.00804    0.00798    0.00119
C3    1    0.414784    0.329687    0.571840    11.00000    0.04598    0.03976 =
         0.06684    0.00068    0.00310   -0.00102
C2    1    0.568523    0.363235    0.716592    11.00000    0.05456    0.04917 =
         0.05473   -0.00066    0.00094    0.00316
AFIX  43
H2    2    0.602132    0.351929    0.851385    11.00000   -1.20000
AFIX   0
C8    1    0.935300    0.481914    0.929163    11.00000    0.05660    0.04431 =
         0.05790   -0.00101    0.00442   -0.00301
C7    1    0.821637    0.450654    0.805790    11.00000    0.05009    0.04749 =
         0.06153   -0.00371    0.00597   -0.00099
C6    1    0.623397    0.429889    0.454176    11.00000    0.06275    0.04363 =
         0.06028    0.00073    0.01141    0.00028
AFIX  43
H6    2    0.695064    0.463662    0.412953    11.00000   -1.20000
AFIX   0
C4    1    0.365374    0.345121    0.372775    11.00000    0.05819    0.04831 =
         0.06208   -0.00932   -0.00264    0.00567
AFIX  43
H4    2    0.262675    0.321859    0.277846    11.00000   -1.20000
AFIX   0
C5    1    0.469127    0.395578    0.313393    11.00000    0.07206    0.05442 =
         0.05337   -0.00121    0.00313    0.00567
AFIX  43
H5    2    0.434901    0.406454    0.178129    11.00000   -1.20000
AFIX   0
HKLF 4




REM  qjc-3cl_auto_a.res in P2(1)/n
REM wR2 = 0.1563, GooF = S = 1.168, Restrained GooF = 1.168 for all data
REM R1 = 0.0474 for 933 Fo > 4sig(Fo) and 0.0652 for all 1212 data
REM 82 parameters refined using 0 restraints

END

WGHT      0.0684      0.2152

REM Highest difference peak  0.301,  deepest hole -0.356,  1-sigma level  0.052
Q1    1   0.3161  0.3743  0.1684  11.00000  0.05    0.30
Q2    1   0.5954  0.3440  0.6049  11.00000  0.05    0.18
Q3    1   0.2894  0.3162  0.5982  11.00000  0.05    0.18
Q4    1   0.2819  0.2657  0.8164  11.00000  0.05    0.18
Q5    1   0.6148  0.3915  0.7094  11.00000  0.05    0.17
;
_shelx_res_checksum              77340
_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 2.331
_oxdiff_exptl_absorpt_empirical_full_min 0.646
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
Cl9 Cl 0.2772(2) 0.26701(3) 0.65064(15) 0.0738(4) Uani 1 1 d . . . . .
C1 C 0.6723(7) 0.41433(12) 0.6569(5) 0.0491(7) Uani 1 1 d . . . . .
C3 C 0.4148(7) 0.32969(11) 0.5718(5) 0.0508(7) Uani 1 1 d . . . . .
C2 C 0.5685(7) 0.36323(12) 0.7166(5) 0.0529(7) Uani 1 1 d . . . . .
H2 H 0.602132 0.351929 0.851385 0.063 Uiso 1 1 calc R U . . .
C8 C 0.9353(7) 0.48191(12) 0.9292(5) 0.0529(7) Uani 1 1 d . . . . .
C7 C 0.8216(7) 0.45065(12) 0.8058(5) 0.0529(7) Uani 1 1 d . . . . .
C6 C 0.6234(8) 0.42989(12) 0.4542(5) 0.0553(8) Uani 1 1 d . . . . .
H6 H 0.695064 0.463662 0.412953 0.066 Uiso 1 1 calc R U . . .
C4 C 0.3654(8) 0.34512(12) 0.3728(5) 0.0563(8) Uani 1 1 d . . . . .
H4 H 0.262675 0.321859 0.277846 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4691(8) 0.39558(13) 0.3134(5) 0.0599(8) Uani 1 1 d . . . . .
H5 H 0.434901 0.406454 0.178129 0.072 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl9 0.0766(6) 0.0491(5) 0.0950(8) 0.0092(4) -0.0063(5) -0.0113(4)
C1 0.0461(15) 0.0438(15) 0.0580(18) -0.0080(13) 0.0080(12) 0.0012(12)
C3 0.0460(15) 0.0398(14) 0.0668(19) 0.0007(13) 0.0031(13) -0.0010(12)
C2 0.0546(17) 0.0492(16) 0.0547(17) -0.0007(14) 0.0009(13) 0.0032(13)
C8 0.0566(16) 0.0443(15) 0.0579(18) -0.0010(14) 0.0044(13) -0.0030(13)
C7 0.0501(16) 0.0475(16) 0.0615(18) -0.0037(14) 0.0060(13) -0.0010(13)
C6 0.0628(18) 0.0436(16) 0.0603(19) 0.0007(14) 0.0114(14) 0.0003(14)
C4 0.0582(18) 0.0483(17) 0.0621(19) -0.0093(14) -0.0026(14) 0.0057(13)
C5 0.072(2) 0.0544(18) 0.0534(18) -0.0012(14) 0.0031(15) 0.0057(15)
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'
Cl Cl 0.3639 0.7018 '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
C2 C1 C7 120.0(3) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 C7 120.7(3) . . ?
C2 C3 Cl9 118.2(2) . . ?
C4 C3 Cl9 120.1(2) . . ?
C4 C3 C2 121.7(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C7 C8 C8 179.7(4) . 3_767 ?
C8 C7 C1 177.6(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
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
Cl9 C3 1.736(3) . ?
C1 C2 1.396(4) . ?
C1 C7 1.438(4) . ?
C1 C6 1.387(4) . ?
C3 C2 1.384(4) . ?
C3 C4 1.364(4) . ?
C2 H2 0.9300 . ?
C8 C8 1.375(6) 3_767 ?
C8 C7 1.195(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 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
Cl9 C3 C2 C1 -178.3(2) . . . . ?
Cl9 C3 C4 C5 178.5(2) . . . . ?
C1 C6 C5 C4 -0.7(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C7 C1 C2 C3 177.8(3) . . . . ?
C7 C1 C6 C5 -177.7(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C4 C3 C2 C1 0.6(5) . . . . ?
