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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/1/56/68/1566838.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_1566838
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            'C24 H21 N3'
_chemical_formula_weight         351.44
_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                 113.683(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9544(12)
_cell_length_b                   15.4590(15)
_cell_length_c                   12.2647(13)
_cell_measurement_reflns_used    8311
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.3190
_cell_measurement_theta_min      4.2070
_cell_volume                     1902.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.971
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14592
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.800
_diffrn_reflns_theta_min         4.230
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.377
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.377
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0802
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2643
_refine_ls_wR_factor_ref         0.3583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2792
_reflns_number_total             4270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00837h2.cif
_cod_data_source_block           Compound-4-66
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566838
_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
N1 N 0.5261(2) 0.40224(13) 0.63276(16) 0.0536(6) Uani 1 1 d . . . . .
N2 N 0.9615(3) 0.3947(2) 0.6551(3) 0.0994(10) Uani 1 1 d . . . . .
N3 N 0.3640(2) 0.37483(15) 0.43183(18) 0.0632(7) Uani 1 1 d . . . . .
C1 C 0.6152(3) 0.36206(16) 0.37472(19) 0.0575(7) Uani 1 1 d . . . . .
C2 C 0.7260(3) 0.3888(2) 0.3549(2) 0.0663(8) Uani 1 1 d . . . . .
H2 H 0.795195 0.417080 0.415351 0.080 Uiso 1 1 calc R U . . .
C3 C 0.7354(4) 0.3741(2) 0.2472(3) 0.0773(9) Uani 1 1 d . . . . .
H3 H 0.811290 0.391181 0.236501 0.093 Uiso 1 1 calc R U . . .
C4 C 0.6319(4) 0.3342(2) 0.1556(2) 0.0819(10) Uani 1 1 d . . . . .
H4 H 0.636989 0.324866 0.082648 0.098 Uiso 1 1 calc R U . . .
C5 C 0.5214(4) 0.30824(19) 0.1735(2) 0.0733(9) Uani 1 1 d . . . . .
H5 H 0.450877 0.281847 0.111895 0.088 Uiso 1 1 calc R U . . .
C6 C 0.5140(3) 0.32105(18) 0.2821(2) 0.0652(8) Uani 1 1 d . . . . .
H6 H 0.439361 0.301671 0.293089 0.078 Uiso 1 1 calc R U . . .
C7 C 0.6063(3) 0.37912(15) 0.4896(2) 0.0541(7) Uani 1 1 d . . . . .
C8 C 0.7115(3) 0.39377(16) 0.6030(2) 0.0546(7) Uani 1 1 d . . . . .
C9 C 0.6613(3) 0.40762(16) 0.68816(19) 0.0528(7) Uani 1 1 d . . . . .
C10 C 0.4916(3) 0.38422(16) 0.51009(19) 0.0535(7) Uani 1 1 d . . . . .
C11 C 0.8489(3) 0.3940(2) 0.6313(2) 0.0659(8) Uani 1 1 d . . . . .
C12 C 0.7393(3) 0.42727(17) 0.81560(19) 0.0551(7) Uani 1 1 d . . . . .
C13 C 0.8022(3) 0.3608(2) 0.8941(2) 0.0686(8) Uani 1 1 d . . . . .
H13 H 0.796310 0.304141 0.867116 0.082 Uiso 1 1 calc R U . . .
C14 C 0.8740(3) 0.3802(3) 1.0135(2) 0.0828(11) Uani 1 1 d . . . . .
H14 H 0.915261 0.335860 1.066839 0.099 Uiso 1 1 calc R U . . .
C15 C 0.8849(3) 0.4633(3) 1.0535(2) 0.0855(11) Uani 1 1 d . . . . .
H15 H 0.933072 0.475294 1.133829 0.103 Uiso 1 1 calc R U . . .
C16 C 0.8253(3) 0.5288(2) 0.9760(3) 0.0812(10) Uani 1 1 d . . . . .
H16 H 0.833646 0.585436 1.003604 0.097 Uiso 1 1 calc R U . . .
C17 C 0.7524(3) 0.5117(2) 0.8566(2) 0.0673(8) Uani 1 1 d . . . . .
H17 H 0.712352 0.556738 0.804007 0.081 Uiso 1 1 calc R U . . .
C18 C 0.4272(3) 0.40399(17) 0.6761(2) 0.0585(7) Uani 1 1 d . . . . .
C19 C 0.2998(3) 0.3924(2) 0.5956(3) 0.0679(8) Uani 1 1 d . . . . .
H19 H 0.230624 0.392964 0.621216 0.081 Uiso 1 1 calc R U . . .
C20 C 0.2707(3) 0.37956(19) 0.4728(2) 0.0654(8) Uani 1 1 d . . . . .
C21 C 0.4633(3) 0.4178(2) 0.8062(2) 0.0708(8) Uani 1 1 d . . . . .
H21A H 0.492985 0.477098 0.825670 0.085 Uiso 1 1 calc R U . . .
H21B H 0.537999 0.380482 0.850627 0.085 Uiso 1 1 calc R U . . .
C22 C 0.3526(4) 0.4007(3) 0.8480(3) 0.0894(11) Uani 1 1 d . . . . .
H22A H 0.277632 0.437076 0.804666 0.134 Uiso 1 1 calc R U . . .
H22B H 0.383967 0.413222 0.931523 0.134 Uiso 1 1 calc R U . . .
H22C H 0.326136 0.341165 0.834282 0.134 Uiso 1 1 calc R U . . .
C23 C 0.1295(3) 0.3665(2) 0.3867(3) 0.0841(10) Uani 1 1 d . . . . .
H23A H 0.072365 0.405073 0.407478 0.101 Uiso 1 1 calc R U . . .
H23B H 0.121696 0.381977 0.307519 0.101 Uiso 1 1 calc R U . . .
C24 C 0.0835(5) 0.2796(4) 0.3844(7) 0.193(3) Uani 1 1 d . . . . .
H24A H 0.098330 0.247476 0.323822 0.289 Uiso 1 1 calc R U . . .
H24B H -0.010052 0.280109 0.367322 0.289 Uiso 1 1 calc R U . . .
H24C H 0.131319 0.252950 0.460406 0.289 Uiso 1 1 calc R U . . .
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'
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 C18 132.0(2) . . ?
C9 N1 C10 108.2(2) . . ?
C18 N1 C10 119.5(2) . . ?
C20 N3 C10 117.8(2) . . ?
C6 C1 C2 117.4(2) . . ?
C6 C1 C7 121.9(3) . . ?
C2 C1 C7 120.7(2) . . ?
C3 C2 C1 121.5(3) . . ?
C4 C3 C2 119.8(3) . . ?
C5 C4 C3 119.3(3) . . ?
C4 C5 C6 120.6(3) . . ?
C5 C6 C1 121.4(3) . . ?
C10 C7 C8 104.6(2) . . ?
C10 C7 C1 126.8(2) . . ?
C8 C7 C1 128.5(2) . . ?
C9 C8 C11 121.8(2) . . ?
C9 C8 C7 110.6(2) . . ?
C11 C8 C7 127.6(2) . . ?
N1 C9 C8 107.3(2) . . ?
N1 C9 C12 126.2(2) . . ?
C8 C9 C12 126.5(2) . . ?
N3 C10 C7 128.6(2) . . ?
N3 C10 N1 122.2(2) . . ?
C7 C10 N1 109.2(2) . . ?
N2 C11 C8 179.4(3) . . ?
C17 C12 C13 119.7(2) . . ?
C17 C12 C9 120.5(2) . . ?
C13 C12 C9 119.7(2) . . ?
C12 C13 C14 119.1(3) . . ?
C15 C14 C13 120.9(3) . . ?
C16 C15 C14 120.0(3) . . ?
C15 C16 C17 120.6(3) . . ?
C16 C17 C12 119.7(3) . . ?
C19 C18 N1 116.8(2) . . ?
C19 C18 C21 123.2(3) . . ?
N1 C18 C21 120.0(3) . . ?
C18 C19 C20 121.1(3) . . ?
N3 C20 C19 122.4(3) . . ?
N3 C20 C23 117.8(3) . . ?
C19 C20 C23 119.7(3) . . ?
C18 C21 C22 115.5(3) . . ?
C24 C23 C20 113.4(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
N1 C9 1.361(3) . ?
N1 C18 1.386(3) . ?
N1 C10 1.424(3) . ?
N2 C11 1.148(4) . ?
N3 C20 1.310(4) . ?
N3 C10 1.349(3) . ?
C1 C6 1.382(4) . ?
C1 C2 1.393(4) . ?
C1 C7 1.475(3) . ?
C2 C3 1.385(4) . ?
C3 C4 1.380(5) . ?
C4 C5 1.375(5) . ?
C5 C6 1.380(3) . ?
C7 C10 1.378(4) . ?
C7 C8 1.423(3) . ?
C8 C9 1.379(3) . ?
C8 C11 1.402(4) . ?
C9 C12 1.481(3) . ?
C12 C17 1.386(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.364(5) . ?
C15 C16 1.363(5) . ?
C16 C17 1.383(4) . ?
C18 C19 1.359(4) . ?
C18 C21 1.497(3) . ?
C19 C20 1.422(4) . ?
C20 C23 1.496(4) . ?
C21 C22 1.517(4) . ?
C23 C24 1.430(6) . ?
