#------------------------------------------------------------------------------
#$Date: 2020-12-06 09:41:43 +0100 (dom 06 de dic de 2020) $
#$Revision: 259587 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/16/7241679.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_7241679
loop_
_publ_author_name
'Leduskrasts, Kaspars'
'Suna, Edgars'
_publ_section_title
;
 Aggregation induced emission in one easy step: pyridinium AIEgens and
 counter ion effect
;
_journal_issue                   62
_journal_name_full               'RSC Advances'
_journal_page_first              38107
_journal_page_last               38113
_journal_paper_doi               10.1039/D0RA07137D
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'Cl O4, C11 H10 N'
_chemical_formula_sum            'C11 H10 Cl N O4'
_chemical_formula_weight         255.66
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-13
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_audit_update_record
;
2020-03-07 deposited with the CCDC.	2020-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.383(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8571(1)
_cell_length_b                   18.2247(2)
_cell_length_c                   9.2749(1)
_cell_measurement_reflns_used    7507
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      77.1220
_cell_measurement_theta_min      4.8290
_cell_volume                     1093.38(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  19.00   0.50    8.33    --  -49.35  96.00  83.00   96
  2  ω    -72.00 -47.00   0.50    8.33    --  -84.25  96.00  83.00   50
  3  ω    -78.00 -34.00   0.50    8.33    --  -49.35  96.00  83.00   88
  4  ω   -115.00 -90.00   0.50    8.33    --  -49.35 -77.00  30.00   50
  5  ω   -119.00 -92.00   0.50    8.33    --  -49.35 -77.00  90.00   54
  6  ω   -119.00 -94.00   0.50    8.33    --  -49.35 -77.00 120.00   50
  7  ω   -116.00 -81.00   0.50    8.33    --  -49.35-125.00 120.00   70
  8  ω   -117.00 -89.00   0.50    8.33    --  -49.35 -77.00   0.00   56
  9  ω   -143.00-118.00   0.50    8.33    --  -84.25 -96.00 -25.00   50
 10  ω     12.00  53.00   0.50    8.33    --   49.66 -96.00 -25.00   82
 11  ω     50.00  76.00   0.50    8.33    --  105.75 -96.00 -25.00   52
 12  ω     79.00 104.00   0.50    8.33    --  105.75 -94.00   0.00   50
 13  ω     70.00  96.00   0.50    8.33    --  105.75 -94.00  30.00   52
 14  ω     56.00  99.00   0.50    8.33    --  105.75 -77.00   0.00   86
 15  ω     43.00  68.00   0.50    8.33    --  105.75 -94.00  30.00   50
 16  ω     50.00  76.00   0.50    8.33    --  105.75 -79.00  -9.73   52
 17  ω     36.00  77.00   0.50    8.33    --  105.75 -77.00  60.00   82
 18  ω     35.00  71.00   0.50    8.33    --  105.75 -94.00   0.00   72
 19  ω     35.00  66.00   0.50    8.33    --  105.75 -77.00  30.00   62
 20  ω    132.00 158.00   0.50    8.33    --  105.75  15.00 -60.00   52
 21  ω    105.00 158.00   0.50    8.33    --  105.75  30.00-180.00  106
 22  ω    118.00 168.00   0.50    8.33    --  105.75 125.00-150.00  100
 23  ω     93.00 151.00   0.50    8.33    --  105.75  61.00 -60.00  116
 24  ω     98.00 124.00   0.50    8.33    --  105.75  45.00  30.00   52
 25  ω    100.00 155.00   0.50    8.33    --  105.75  45.00  90.00  110
 26  ω    107.00 133.00   0.50    8.33    --  105.75  96.00  83.00   52
 27  ω    101.00 128.00   0.50    8.33    --  105.75  61.00 120.00   54
 28  ω     76.00 113.00   0.50    8.33    --  105.75 154.00 117.47   74
 29  ω    142.00 167.00   0.50    8.33    --  105.75 154.00 117.47   50
 30  ω     98.00 174.00   0.50    8.33    --  105.75  61.00-150.00  152
 31  ω     74.00 100.00   0.50    8.33    --  105.75 -77.00-120.00   52
 32  ω     35.00  69.00   0.50    8.33    --  105.75 -61.00-120.00   68
 33  ω     45.00  71.00   0.50    8.33    --  105.75 -61.00-150.00   52
 34  ω     34.00  87.00   0.50    8.33    --  105.75 -94.00-150.00  106
 35  ω     45.00  85.00   0.50    8.33    --  105.75 -86.00 174.27   80
 36  ω     89.00 114.00   0.50    8.33    --  105.75 -86.00 174.27   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1322291000
_diffrn_orient_matrix_UB_12      -0.0694345000
_diffrn_orient_matrix_UB_13      0.0102302000
_diffrn_orient_matrix_UB_21      -0.1841707000
_diffrn_orient_matrix_UB_22      -0.0380788000
_diffrn_orient_matrix_UB_23      -0.1193012000
_diffrn_orient_matrix_UB_31      0.0727598000
_diffrn_orient_matrix_UB_32      0.0296713000
_diffrn_orient_matrix_UB_33      -0.1290902000
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10027
_diffrn_reflns_theta_full        77.2643
_diffrn_reflns_theta_max         77.26
_diffrn_reflns_theta_min         4.85
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.155
_exptl_absorpt_correction_T_max  0.91048
_exptl_absorpt_correction_T_min  0.69642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.5530
_exptl_crystal_description       Block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.3367
_refine_diff_density_min         -0.6010
_refine_diff_density_rms         0.0929
_refine_ls_d_res_high            0.7904
_refine_ls_d_res_low             9.1123
_refine_ls_goodness_of_fit_ref   1.0242
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0242
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0670P)²+0.8907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2098
_reflns_number_total             2308
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ra07137d2.cif
_cod_data_source_block           KL1248
_cod_database_code               7241679
_chemical_oxdiff_formula         'C44 H40 Cl4 N4 O16 '
_chemical_oxdiff_usercomment     'from Kaspars'
_diffrn_oxdiff_digest_frames
;
0175de1edc245abbe347a256a32224d9c200026318a
;
_diffrn_oxdiff_digest_hkl
;
01587f8538602881b2f95c1de280da1710bc93
;
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_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), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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 1.383
_oxdiff_exptl_absorpt_empirical_full_min 0.714
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
Cl1 Cl 0.51332(7) 0.15878(2) 0.60789(5) 0.02630(17) Uani 1.000000 .
O4 O 0.4184(2) 0.08736(8) 0.58303(17) 0.0333(4) Uani 1.000000 .
O2 O 0.4964(2) 0.19236(8) 0.46341(15) 0.0312(3) Uani 1.000000 .
O3 O 0.7277(3) 0.15138(9) 0.69806(19) 0.0407(4) Uani 1.000000 .
O1 O 0.4097(3) 0.20448(9) 0.68687(19) 0.0434(4) Uani 1.000000 .
N1 N 0.3605(3) 0.36404(10) 0.6460(2) 0.0271(4) Uani 1.000000 .
H1 H 0.398(4) 0.3264(16) 0.702(3) 0.036(7) Uiso 1.000000 .
C7 C 0.1832(3) 0.55083(10) 0.3589(2) 0.0219(4) Uani 1.000000 .
C4 C 0.2411(3) 0.48498(10) 0.4580(2) 0.0210(4) Uani 1.000000 .
C5 C 0.2852(3) 0.49000(11) 0.6167(2) 0.0247(4) Uani 1.000000 .
H5 H 0.2743(3) 0.53506(11) 0.6604(2) 0.0296(5) Uiso 1.000000 R
C3 C 0.2584(3) 0.41541(11) 0.3995(2) 0.0274(4) Uani 1.000000 .
H3 H 0.2283(3) 0.40937(11) 0.2948(2) 0.0328(5) Uiso 1.000000 R
C12 C 0.1654(3) 0.61962(11) 0.4200(2) 0.0267(4) Uani 1.000000 .
H12 H 0.1887(3) 0.62412(11) 0.5243(2) 0.0320(5) Uiso 1.000000 R
C9 C 0.0970(3) 0.60797(13) 0.1097(2) 0.0335(5) Uani 1.000000 .
H9 H 0.0744(3) 0.60403(13) 0.0054(2) 0.0402(6) Uiso 1.000000 R
C6 C 0.3444(3) 0.42911(11) 0.7080(2) 0.0270(4) Uani 1.000000 .
H6 H 0.3733(3) 0.43309(11) 0.8130(2) 0.0324(5) Uiso 1.000000 R
C8 C 0.1483(3) 0.54608(12) 0.2017(2) 0.0281(4) Uani 1.000000 .
H8 H 0.1596(3) 0.50092(12) 0.1585(2) 0.0338(5) Uiso 1.000000 R
C11 C 0.1133(3) 0.68137(12) 0.3273(3) 0.0321(5) Uani 1.000000 .
H11 H 0.1012(3) 0.72671(12) 0.3695(3) 0.0385(5) Uiso 1.000000 R
C2 C 0.3194(3) 0.35595(11) 0.4949(2) 0.0296(4) Uani 1.000000 .
H2 H 0.3321(3) 0.31011(11) 0.4548(2) 0.0355(5) Uiso 1.000000 R
C10 C 0.0794(3) 0.67554(13) 0.1724(3) 0.0340(5) Uani 1.000000 .
H10 H 0.0449(3) 0.71691(13) 0.1103(3) 0.0409(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
O2 Cl1 O4 110.00(9) . . ?
O3 Cl1 O4 109.24(10) . . ?
O3 Cl1 O2 109.40(10) . . ?
O1 Cl1 O4 109.32(10) . . ?
O1 Cl1 O2 108.99(9) . . ?
O1 Cl1 O3 109.88(11) . . ?
C6 N1 H1 120.1(19) . . ?
C2 N1 H1 118.1(19) . . ?
C2 N1 C6 121.81(18) . . ?
C12 C7 C4 121.06(17) . . ?
C8 C7 C4 120.90(17) . . ?
C8 C7 C12 118.04(17) . . ?
C5 C4 C7 121.14(17) . . ?
C3 C4 C7 122.17(17) . . ?
C3 C4 C5 116.67(17) . . ?
H5 C5 C4 119.63(11) . . ?
C6 C5 C4 120.74(18) . . ?
C6 C5 H5 119.63(12) . . ?
H3 C3 C4 119.60(11) . . ?
C2 C3 C4 120.80(18) . . ?
C2 C3 H3 119.60(12) . . ?
H12 C12 C7 119.51(11) . . ?
C11 C12 C7 120.98(19) . . ?
C11 C12 H12 119.51(13) . . ?
C8 C9 H9 119.86(13) . . ?
C10 C9 H9 119.86(12) . . ?
C10 C9 C8 120.3(2) . . ?
C5 C6 N1 120.02(18) . . ?
H6 C6 N1 119.99(11) . . ?
H6 C6 C5 119.99(12) . . ?
C9 C8 C7 120.8(2) . . ?
H8 C8 C7 119.62(11) . . ?
H8 C8 C9 119.62(13) . . ?
H11 C11 C12 119.94(13) . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 119.94(13) . . ?
C3 C2 N1 119.95(19) . . ?
H2 C2 N1 120.03(12) . . ?
H2 C2 C3 120.03(12) . . ?
C11 C10 C9 119.8(2) . . ?
H10 C10 C9 120.09(12) . . ?
H10 C10 C11 120.09(13) . . ?
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
Cl1 O4 1.4392(15) . ?
Cl1 O2 1.4424(14) . ?
Cl1 O3 1.4363(18) . ?
Cl1 O1 1.4423(16) . ?
N1 H1 0.85(3) . ?
N1 C6 1.339(3) . ?
N1 C2 1.343(3) . ?
C7 C4 1.483(3) . ?
C7 C12 1.398(3) . ?
C7 C8 1.399(3) . ?
C4 C5 1.404(3) . ?
C4 C3 1.400(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.373(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.389(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.388(3) . ?
C9 C10 1.384(3) . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.381(3) . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?
