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#$Date: 2022-04-21 01:13:48 +0300 (Thu, 21 Apr 2022) $
#$Revision: 274606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566841.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_1566841
loop_
_publ_author_name
'Li, Taian'
'Chiou, Mong-Feng'
'Li, Yajun'
'Ye, Changqing'
'Su, Min'
'Xue, Mengyu'
'Yuan, Xiaobin'
'Wang, Chuanchuan'
'Wan, Wen-Ming'
'Li, Daliang'
'Bao, Hongli'
_publ_section_title
;
 Synthesis of Unsymmetrically Tetrasubstituted Pyrroles and Studies of
 AIEE in Pyrrolo[1,2-a]pyrimidine Derivatives
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00837H
_journal_year                    2022
_chemical_formula_sum            'C38 H25 Cl2 N3'
_chemical_formula_weight         594.51
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.611(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6662(4)
_cell_length_b                   23.9537(7)
_cell_length_c                   12.5820(4)
_cell_measurement_reflns_used    12581
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.0480
_cell_measurement_theta_min      3.7420
_cell_volume                     3170.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28166
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.706
_diffrn_reflns_theta_min         3.748
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    1.367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_refine_diff_density_max         1.047
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.755
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.755
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.1166
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3977
_refine_ls_wR_factor_ref         0.4111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5505
_reflns_number_total             7132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00837h2.cif
_cod_data_source_block           Compound-1_CCDC3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566841
_shelx_shelxl_version_number     2018/3
_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.
;
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
Cl1 Cl 0.2967(5) 0.7656(5) 0.7709(5) 0.231(5) Uani 0.386(5) 1 d . . P A 1
Cl2 Cl 0.1921(9) 0.8330(3) 0.5016(14) 0.339(11) Uani 0.386(5) 1 d . . P A 1
Cl3 Cl 0.2300(5) 0.8367(2) 0.6852(6) 0.222(3) Uani 0.614(5) 1 d . . P A 2
Cl4 Cl 0.1464(2) 0.72767(12) 0.5523(2) 0.1274(11) Uani 0.614(5) 1 d . . P A 2
N1 N 0.8221(2) 0.70881(10) 0.3328(2) 0.0560(6) Uani 1 1 d . . . . .
N2 N 0.7279(2) 0.78559(10) 0.39517(19) 0.0532(6) Uani 1 1 d . . . . .
N3 N 0.4966(4) 0.7130(2) 0.5921(4) 0.1079(13) Uani 1 1 d . . . . .
C1 C 0.5086(4) 0.87103(19) 0.3554(3) 0.0859(12) Uani 1 1 d . . . . .
H1A H 0.505228 0.859854 0.283332 0.103 Uiso 1 1 calc R U . . .
C2 C 0.4405(5) 0.9173(2) 0.3621(5) 0.1133(18) Uani 1 1 d . . . . .
H2 H 0.394828 0.938121 0.294396 0.136 Uiso 1 1 calc R U . . .
C3 C 0.4391(7) 0.9327(3) 0.4638(5) 0.126(2) Uani 1 1 d . . . . .
H3 H 0.389367 0.962740 0.465634 0.151 Uiso 1 1 calc R U . . .
C4 C 0.5116(6) 0.9039(2) 0.5658(4) 0.1050(16) Uani 1 1 d . . . . .
H4 H 0.512509 0.915129 0.636889 0.126 Uiso 1 1 calc R U . . .
C5 C 0.5834(4) 0.85815(17) 0.5627(3) 0.0791(10) Uani 1 1 d . . . . .
H5 H 0.632466 0.838737 0.631503 0.095 Uiso 1 1 calc R U . . .
C6 C 0.5812(3) 0.84177(14) 0.4568(3) 0.0666(8) Uani 1 1 d . . . . .
C7 C 0.6482(3) 0.79079(13) 0.4494(2) 0.0587(7) Uani 1 1 d . . . . .
C8 C 0.6302(3) 0.73738(14) 0.4825(3) 0.0616(8) Uani 1 1 d . . . . .
C9 C 0.6949(3) 0.69774(13) 0.4448(3) 0.0577(7) Uani 1 1 d . . . . .
C10 C 0.7542(3) 0.72853(12) 0.3894(2) 0.0545(7) Uani 1 1 d . . . . .
C11 C 0.9406(3) 0.72576(14) 0.2187(3) 0.0676(8) Uani 1 1 d . . . . .
H11A H 0.959804 0.686818 0.234698 0.101 Uiso 1 1 calc R U . . .
H11B H 1.018363 0.746544 0.244096 0.101 Uiso 1 1 calc R U . . .
H11C H 0.890924 0.731052 0.135567 0.101 Uiso 1 1 calc R U . . .
C12 C 0.8669(3) 0.74585(12) 0.2838(3) 0.0572(7) Uani 1 1 d . . . . .
C13 C 0.8524(3) 0.80400(12) 0.2951(3) 0.0590(7) Uani 1 1 d . . . . .
H13 H 0.890244 0.828795 0.263016 0.071 Uiso 1 1 calc R U . . .
C14 C 0.7852(3) 0.82459(12) 0.3511(2) 0.0539(7) Uani 1 1 d . . . . .
C15 C 0.7836(3) 0.88540(12) 0.3733(3) 0.0595(7) Uani 1 1 d . . . . .
C16 C 0.7517(4) 0.92174(14) 0.2786(3) 0.0667(8) Uani 1 1 d . . . . .
H16 H 0.722140 0.907600 0.202543 0.080 Uiso 1 1 calc R U . . .
C17 C 0.7637(4) 0.97869(15) 0.2969(3) 0.0820(11) Uani 1 1 d . . . . .
H17 H 0.743246 1.002714 0.233200 0.098 Uiso 1 1 calc R U . . .
C18 C 0.8050(5) 0.99964(16) 0.4071(4) 0.0951(14) Uani 1 1 d . . . . .
H18 H 0.810526 1.038067 0.418818 0.114 Uiso 1 1 calc R U . . .
C19 C 0.8387(6) 0.96420(17) 0.5016(4) 0.0954(13) Uani 1 1 d . . . . .
H19 H 0.870616 0.978545 0.577685 0.115 Uiso 1 1 calc R U . . .
C20 C 0.8250(4) 0.90696(14) 0.4835(3) 0.0774(10) Uani 1 1 d . . . . .
H20 H 0.844353 0.883165 0.547401 0.093 Uiso 1 1 calc R U . . .
C21 C 0.5544(3) 0.72496(17) 0.5430(3) 0.0746(9) Uani 1 1 d . . . . .
C22 C 0.6882(3) 0.63635(13) 0.4518(3) 0.0571(7) Uani 1 1 d . . . . .
C23 C 0.5682(3) 0.61132(19) 0.3967(3) 0.0784(10) Uani 1 1 d . . . . .
H23 H 0.496637 0.633587 0.358841 0.094 Uiso 1 1 calc R U . . .
C24 C 0.5545(4) 0.55392(19) 0.3976(3) 0.0834(11) Uani 1 1 d . . . . .
H24 H 0.473992 0.538293 0.358732 0.100 Uiso 1 1 calc R U . . .
C25 C 0.6560(4) 0.52000(15) 0.4540(3) 0.0720(9) Uani 1 1 d . . . . .
C26 C 0.6442(5) 0.45981(18) 0.4560(4) 0.0879(12) Uani 1 1 d . . . . .
H26 H 0.564663 0.443438 0.415504 0.105 Uiso 1 1 calc R U . . .
C27 C 0.7429(6) 0.42809(18) 0.5134(4) 0.0951(14) Uani 1 1 d . . . . .
H27 H 0.730667 0.389755 0.514074 0.114 Uiso 1 1 calc R U . . .
C28 C 0.8690(5) 0.44962(14) 0.5753(3) 0.0770(11) Uani 1 1 d . . . . .
C29 C 0.9732(6) 0.41632(18) 0.6320(4) 0.0912(13) Uani 1 1 d . . . . .
H29 H 0.963303 0.377811 0.632291 0.109 Uiso 1 1 calc R U . . .
C30 C 1.0926(6) 0.4394(2) 0.6884(4) 0.1023(18) Uani 1 1 d . . . . .
H30 H 1.162699 0.416009 0.723932 0.123 Uiso 1 1 calc R U . . .
C31 C 1.1107(4) 0.49702(18) 0.6935(3) 0.0843(11) Uani 1 1 d . . . . .
H31 H 1.191827 0.511645 0.735259 0.101 Uiso 1 1 calc R U . . .
C32 C 1.0068(4) 0.53342(14) 0.6359(3) 0.0671(8) Uani 1 1 d . . . . .
C33 C 1.0217(3) 0.59249(14) 0.6349(3) 0.0627(7) Uani 1 1 d . . . . .
H33 H 1.101679 0.608342 0.675757 0.075 Uiso 1 1 calc R U . . .
C34 C 0.9200(3) 0.62567(12) 0.5746(2) 0.0561(7) Uani 1 1 d . . . . .
H34 H 0.931506 0.664051 0.573797 0.067 Uiso 1 1 calc R U . . .
C35 C 0.7945(3) 0.60269(11) 0.5120(2) 0.0506(6) Uani 1 1 d . . . . .
C36 C 0.7794(3) 0.54402(12) 0.5144(2) 0.0589(7) Uani 1 1 d . . . . .
C37 C 0.8856(3) 0.50918(13) 0.5759(3) 0.0637(8) Uani 1 1 d . . . . .
C38 C 0.2611(6) 0.7779(4) 0.6226(8) 0.165(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 '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
C12 N1 C10 116.9(2) . . ?
C7 N2 C14 132.7(2) . . ?
C7 N2 C10 108.8(2) . . ?
C14 N2 C10 118.4(2) . . ?
C6 C1 C2 119.3(4) . . ?
C3 C2 C1 121.5(4) . . ?
C2 C3 C4 119.7(4) . . ?
C3 C4 C5 120.3(4) . . ?
C6 C5 C4 119.4(4) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C7 120.5(3) . . ?
C1 C6 C7 119.6(3) . . ?
N2 C7 C8 106.7(2) . . ?
N2 C7 C6 126.6(3) . . ?
C8 C7 C6 126.2(3) . . ?
C7 C8 C9 110.2(3) . . ?
C7 C8 C21 124.2(3) . . ?
C9 C8 C21 125.6(3) . . ?
C10 C9 C8 105.4(3) . . ?
C10 C9 C22 127.6(2) . . ?
C8 C9 C22 126.7(3) . . ?
N1 C10 C9 127.5(3) . . ?
N1 C10 N2 123.6(2) . . ?
C9 C10 N2 108.8(2) . . ?
N1 C12 C13 121.9(2) . . ?
N1 C12 C11 118.6(3) . . ?
C13 C12 C11 119.5(3) . . ?
C14 C13 C12 122.1(3) . . ?
C13 C14 N2 116.6(3) . . ?
C13 C14 C15 120.8(3) . . ?
N2 C14 C15 122.4(2) . . ?
C20 C15 C16 118.8(3) . . ?
C20 C15 C14 122.5(3) . . ?
C16 C15 C14 118.3(3) . . ?
C17 C16 C15 120.4(3) . . ?
C18 C17 C16 120.2(3) . . ?
C17 C18 C19 120.0(4) . . ?
C18 C19 C20 119.9(4) . . ?
C15 C20 C19 120.5(3) . . ?
N3 C21 C8 177.2(4) . . ?
C35 C22 C23 119.0(3) . . ?
C35 C22 C9 123.3(2) . . ?
C23 C22 C9 117.7(3) . . ?
C24 C23 C22 121.0(4) . . ?
C25 C24 C23 121.4(3) . . ?
C24 C25 C36 119.3(3) . . ?
C24 C25 C26 122.4(4) . . ?
C36 C25 C26 118.3(4) . . ?
C27 C26 C25 121.3(4) . . ?
C26 C27 C28 123.0(4) . . ?
C29 C28 C27 123.1(4) . . ?
C29 C28 C37 119.2(4) . . ?
C27 C28 C37 117.7(4) . . ?
C28 C29 C30 120.6(4) . . ?
C29 C30 C31 121.3(4) . . ?
C30 C31 C32 120.6(5) . . ?
C37 C32 C31 117.4(3) . . ?
C37 C32 C33 120.1(3) . . ?
C31 C32 C33 122.4(4) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 121.3(3) . . ?
C22 C35 C36 119.7(3) . . ?
C22 C35 C34 122.1(2) . . ?
C36 C35 C34 118.2(3) . . ?
C37 C36 C35 120.6(3) . . ?
C37 C36 C25 119.8(3) . . ?
C35 C36 C25 119.6(3) . . ?
C32 C37 C36 119.3(3) . . ?
C32 C37 C28 120.9(3) . . ?
C36 C37 C28 119.9(3) . . ?
Cl3 C38 Cl4 122.1(4) . . ?
Cl1 C38 Cl2 142.2(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
Cl1 C38 1.752(12) . ?
Cl2 C38 1.910(15) . ?
Cl3 C38 1.725(10) . ?
Cl4 C38 1.732(8) . ?
N1 C12 1.312(4) . ?
N1 C10 1.358(4) . ?
N2 C7 1.376(3) . ?
N2 C14 1.395(4) . ?
N2 C10 1.410(4) . ?
N3 C21 1.130(5) . ?
C1 C6 1.379(5) . ?
C1 C2 1.388(6) . ?
C2 C3 1.339(7) . ?
C3 C4 1.378(7) . ?
C4 C5 1.390(6) . ?
C5 C6 1.379(5) . ?
C6 C7 1.474(4) . ?
C7 C8 1.389(4) . ?
C8 C9 1.417(4) . ?
C8 C21 1.426(4) . ?
C9 C10 1.387(4) . ?
C9 C22 1.477(4) . ?
C11 C12 1.500(4) . ?
C12 C13 1.418(4) . ?
C13 C14 1.354(4) . ?
C14 C15 1.485(4) . ?
C15 C20 1.358(5) . ?
C15 C16 1.390(4) . ?
C16 C17 1.380(5) . ?
C17 C18 1.352(6) . ?
C18 C19 1.373(6) . ?
C19 C20 1.388(5) . ?
C22 C35 1.396(4) . ?
C22 C23 1.400(5) . ?
C23 C24 1.385(6) . ?
C24 C25 1.356(6) . ?
C25 C36 1.427(5) . ?
C25 C26 1.450(5) . ?
C26 C27 1.306(7) . ?
C27 C28 1.430(7) . ?
C28 C29 1.369(7) . ?
C28 C37 1.439(4) . ?
C29 C30 1.376(8) . ?
C30 C31 1.394(6) . ?
C31 C32 1.412(5) . ?
C32 C37 1.409(5) . ?
C32 C33 1.426(5) . ?
C33 C34 1.355(4) . ?
C34 C35 1.439(4) . ?
C35 C36 1.418(4) . ?
C36 C37 1.414(5) . ?
