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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/1/56/68/1566836.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_1566836
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            'C23 H19 N3'
_chemical_formula_weight         337.41
_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
_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                107.748(4)
_cell_angle_beta                 101.471(5)
_cell_angle_gamma                103.216(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4368(5)
_cell_length_b                   11.5205(6)
_cell_length_c                   11.7843(5)
_cell_measurement_reflns_used    6437
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.2760
_cell_measurement_theta_min      3.5670
_cell_volume                     895.98(10)
_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 0.999
_diffrn_measured_fraction_theta_max 0.947
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         61.476
_diffrn_reflns_theta_min         3.577
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86643
_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            'pale yellow'
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0076(17)
_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   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0484
_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)+(0.0715P)²+0.0889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2776
_reflns_number_total             4000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00837h2.cif
_cod_data_source_block           Compound-1
_cod_original_cell_volume        895.98(9)
_cod_database_code               1566836
_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, -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
N1 N 0.62169(17) 0.47457(11) 0.35237(11) 0.0489(3) Uani 1 1 d . . . . .
N2 N 0.5076(3) 0.05053(16) 0.32912(17) 0.0957(6) Uani 1 1 d . . . . .
N3 N 0.82520(18) 0.62947(12) 0.55302(12) 0.0565(3) Uani 1 1 d . . . . .
C1 C 0.8169(2) 0.38550(16) 0.61858(14) 0.0537(4) Uani 1 1 d . . . . .
C2 C 0.7629(3) 0.27254(18) 0.64109(17) 0.0666(5) Uani 1 1 d . . . . .
H2 H 0.668559 0.201153 0.579537 0.080 Uiso 1 1 calc R U . . .
C3 C 0.8465(3) 0.2641(2) 0.75305(18) 0.0768(5) Uani 1 1 d . . . . .
H3 H 0.808958 0.187326 0.765478 0.092 Uiso 1 1 calc R U . . .
C4 C 0.9849(3) 0.3688(2) 0.84602(17) 0.0764(5) Uani 1 1 d . . . . .
H4 H 1.040038 0.363453 0.921621 0.092 Uiso 1 1 calc R U . . .
C5 C 1.0406(3) 0.4810(2) 0.82593(16) 0.0694(5) Uani 1 1 d . . . . .
H5 H 1.133946 0.552119 0.888509 0.083 Uiso 1 1 calc R U . . .
C6 C 0.9597(2) 0.48967(17) 0.71365(15) 0.0608(4) Uani 1 1 d . . . . .
H6 H 1.001077 0.566209 0.701344 0.073 Uiso 1 1 calc R U . . .
C7 C 0.7249(2) 0.39497(14) 0.50032(13) 0.0500(4) Uani 1 1 d . . . . .
C8 C 0.6100(2) 0.29440(14) 0.38641(14) 0.0525(4) Uani 1 1 d . . . . .
C9 C 0.5477(2) 0.34299(14) 0.29724(14) 0.0514(4) Uani 1 1 d . . . . .
C10 C 0.7314(2) 0.50647(14) 0.47671(13) 0.0486(3) Uani 1 1 d . . . . .
C11 C 0.5553(3) 0.15968(16) 0.35656(16) 0.0656(5) Uani 1 1 d . . . . .
C12 C 0.4266(3) 0.26463(14) 0.16816(14) 0.0602(4) Uani 1 1 d . . . . .
C13 C 0.2283(3) 0.24150(19) 0.13655(18) 0.0774(5) Uani 1 1 d . . . . .
H13 H 0.172082 0.279216 0.195787 0.093 Uiso 1 1 calc R U . . .
C14 C 0.1143(4) 0.1631(2) 0.0181(2) 0.1137(10) Uani 1 1 d . . . . .
H14 H -0.018421 0.148487 -0.002743 0.136 Uiso 1 1 calc R U . . .
C15 C 0.1954(7) 0.1071(2) -0.0682(2) 0.1352(15) Uani 1 1 d . . . . .
H15 H 0.117907 0.055331 -0.148503 0.162 Uiso 1 1 calc R U . . .
C16 C 0.3921(7) 0.1261(3) -0.0385(2) 0.1313(13) Uani 1 1 d . . . . .
H16 H 0.446149 0.086029 -0.097871 0.158 Uiso 1 1 calc R U . . .
C17 C 0.5087(4) 0.2058(2) 0.08115(19) 0.0924(7) Uani 1 1 d . . . . .
H17 H 0.641111 0.219113 0.102099 0.111 Uiso 1 1 calc R U . . .
C18 C 0.6126(2) 0.57166(15) 0.30583(14) 0.0524(4) Uani 1 1 d . . . . .
C19 C 0.7125(2) 0.69468(15) 0.38327(15) 0.0571(4) Uani 1 1 d . . . . .
C20 C 0.8191(2) 0.72010(15) 0.50845(15) 0.0591(4) Uani 1 1 d . . . . .
C21 C 0.4941(3) 0.53491(17) 0.17463(15) 0.0646(4) Uani 1 1 d . . . . .
H21A H 0.529864 0.468904 0.120331 0.097 Uiso 1 1 calc R U . . .
H21B H 0.516596 0.608454 0.150945 0.097 Uiso 1 1 calc R U . . .
H21C H 0.359896 0.503783 0.168355 0.097 Uiso 1 1 calc R U . . .
C22 C 0.7186(3) 0.80575(18) 0.3406(2) 0.0806(6) Uani 1 1 d . . . . .
H22A H 0.622789 0.777703 0.261878 0.121 Uiso 1 1 calc R U . . .
H22B H 0.844042 0.837824 0.331776 0.121 Uiso 1 1 calc R U . . .
H22C H 0.692905 0.872549 0.400882 0.121 Uiso 1 1 calc R U . . .
C23 C 0.9326(3) 0.85401(18) 0.5963(2) 0.0860(6) Uani 1 1 d . . . . .
H23A H 1.027529 0.890780 0.562035 0.129 Uiso 1 1 calc R U . . .
H23B H 0.995720 0.852193 0.674830 0.129 Uiso 1 1 calc R U . . .
H23C H 0.847119 0.904827 0.608168 0.129 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 131.92(13) . . ?
C9 N1 C10 108.31(12) . . ?
C18 N1 C10 119.70(12) . . ?
C20 N3 C10 118.55(14) . . ?
C2 C1 C6 117.06(15) . . ?
C2 C1 C7 121.36(15) . . ?
C6 C1 C7 121.58(15) . . ?
C3 C2 C1 121.47(18) . . ?
C4 C3 C2 120.37(18) . . ?
C5 C4 C3 119.21(17) . . ?
C4 C5 C6 120.78(17) . . ?
C5 C6 C1 121.10(17) . . ?
C10 C7 C8 104.69(13) . . ?
C10 C7 C1 126.83(14) . . ?
C8 C7 C1 128.48(14) . . ?
C9 C8 C7 110.86(13) . . ?
C9 C8 C11 119.81(14) . . ?
C7 C8 C11 129.33(14) . . ?
N1 C9 C8 106.78(13) . . ?
N1 C9 C12 128.27(13) . . ?
C8 C9 C12 124.94(14) . . ?
N3 C10 C7 129.08(14) . . ?
N3 C10 N1 121.56(13) . . ?
C7 C10 N1 109.35(13) . . ?
N2 C11 C8 177.9(2) . . ?
C17 C12 C13 119.63(18) . . ?
C17 C12 C9 119.81(18) . . ?
C13 C12 C9 120.36(15) . . ?
C14 C13 C12 120.4(2) . . ?
C15 C14 C13 120.0(3) . . ?
C14 C15 C16 120.8(2) . . ?
C15 C16 C17 119.6(3) . . ?
C12 C17 C16 119.6(3) . . ?
C19 C18 N1 117.76(14) . . ?
C19 C18 C21 123.86(14) . . ?
N1 C18 C21 118.38(13) . . ?
C18 C19 C20 119.56(14) . . ?
C18 C19 C22 121.91(15) . . ?
C20 C19 C22 118.52(15) . . ?
N3 C20 C19 122.82(15) . . ?
N3 C20 C23 115.94(16) . . ?
C19 C20 C23 121.23(15) . . ?
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 1.3780(18) . ?
N1 C18 1.3964(18) . ?
N1 C10 1.4167(18) . ?
N2 C11 1.146(2) . ?
N3 C20 1.309(2) . ?
N3 C10 1.3509(19) . ?
C1 C2 1.392(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.473(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.375(3) . ?
C4 C5 1.371(3) . ?
C5 C6 1.384(2) . ?
C7 C10 1.387(2) . ?
C7 C8 1.420(2) . ?
C8 C9 1.384(2) . ?
C8 C11 1.421(2) . ?
C9 C12 1.479(2) . ?
C12 C17 1.378(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.355(5) . ?
C15 C16 1.383(5) . ?
C16 C17 1.394(4) . ?
C18 C19 1.362(2) . ?
C18 C21 1.495(2) . ?
C19 C20 1.434(2) . ?
C19 C22 1.506(2) . ?
C20 C23 1.499(2) . ?
