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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/1/56/68/1566837.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_1566837
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            'C22 H17 N3'
_chemical_formula_weight         323.38
_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                104.037(2)
_cell_angle_beta                 99.019(2)
_cell_angle_gamma                104.020(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5636(2)
_cell_length_b                   10.6070(3)
_cell_length_c                   11.4880(3)
_cell_measurement_reflns_used    6633
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.2850
_cell_measurement_theta_min      5.6370
_cell_volume                     844.45(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 0.970
_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  0.0226
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10297
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         60.617
_diffrn_reflns_theta_min         5.653
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74060
_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    1.272
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.032(3)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0415
_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)+(0.0479P)²+0.1379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3115
_reflns_number_total             3772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00837h2.cif
_cod_data_source_block           Compound-1_CCDC1
_cod_original_cell_volume        844.44(4)
_cod_database_code               1566837
_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 0.37411(13) 0.51869(9) 0.64809(9) 0.0392(2) Uani 1 1 d . . . . .
N2 N 0.3884(2) 0.96564(12) 0.65707(12) 0.0721(4) Uani 1 1 d . . . . .
N3 N 0.20538(14) 0.35701(10) 0.44974(9) 0.0438(2) Uani 1 1 d . . . . .
C1 C 0.17479(16) 0.61932(12) 0.37983(10) 0.0406(3) Uani 1 1 d . . . . .
C2 C 0.04052(17) 0.51033(13) 0.29100(11) 0.0463(3) Uani 1 1 d . . . . .
H2 H -0.000400 0.428230 0.308164 0.056 Uiso 1 1 calc R U . . .
C3 C -0.0324(2) 0.52283(15) 0.17798(12) 0.0551(3) Uani 1 1 d . . . . .
H3 H -0.119995 0.448408 0.119328 0.066 Uiso 1 1 calc R U . . .
C4 C 0.0225(2) 0.64338(16) 0.15070(13) 0.0613(4) Uani 1 1 d . . . . .
H4 H -0.028079 0.651046 0.074443 0.074 Uiso 1 1 calc R U . . .
C5 C 0.1533(2) 0.75285(15) 0.23767(13) 0.0614(4) Uani 1 1 d . . . . .
H5 H 0.190304 0.835257 0.220386 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2298(2) 0.74103(13) 0.35045(12) 0.0519(3) Uani 1 1 d . . . . .
H6 H 0.319500 0.815404 0.407774 0.062 Uiso 1 1 calc R U . . .
C7 C 0.26028(16) 0.60568(11) 0.49883(10) 0.0390(3) Uani 1 1 d . . . . .
C8 C 0.35235(17) 0.71023(12) 0.61067(11) 0.0414(3) Uani 1 1 d . . . . .
C9 C 0.42297(17) 0.65742(11) 0.70058(11) 0.0413(3) Uani 1 1 d . . . . .
C10 C 0.27348(16) 0.48646(11) 0.52444(10) 0.0387(3) Uani 1 1 d . . . . .
C11 C 0.37242(19) 0.85187(13) 0.63559(11) 0.0492(3) Uani 1 1 d . . . . .
C12 C 0.53492(18) 0.73519(12) 0.82597(11) 0.0448(3) Uani 1 1 d . . . . .
C13 C 0.4511(2) 0.79101(14) 0.91617(12) 0.0582(4) Uani 1 1 d . . . . .
H13 H 0.322636 0.778330 0.897998 0.070 Uiso 1 1 calc R U . . .
C14 C 0.5570(3) 0.86547(16) 1.03305(14) 0.0755(5) Uani 1 1 d . . . . .
H14 H 0.499357 0.901097 1.093633 0.091 Uiso 1 1 calc R U . . .
C15 C 0.7468(3) 0.88689(16) 1.05980(15) 0.0808(6) Uani 1 1 d . . . . .
H15 H 0.817571 0.936304 1.138733 0.097 Uiso 1 1 calc R U . . .
C16 C 0.8329(3) 0.83539(16) 0.97002(16) 0.0737(5) Uani 1 1 d . . . . .
H16 H 0.962148 0.851985 0.987973 0.088 Uiso 1 1 calc R U . . .
C17 C 0.7280(2) 0.75912(14) 0.85333(13) 0.0569(3) Uani 1 1 d . . . . .
H17 H 0.786515 0.723821 0.793140 0.068 Uiso 1 1 calc R U . . .
C18 C 0.39431(17) 0.41404(12) 0.69753(11) 0.0434(3) Uani 1 1 d . . . . .
C19 C 0.22699(18) 0.25940(12) 0.49680(12) 0.0470(3) Uani 1 1 d . . . . .
C20 C 0.31879(18) 0.28625(13) 0.62164(12) 0.0485(3) Uani 1 1 d . . . . .
H20 H 0.327128 0.213679 0.651983 0.058 Uiso 1 1 calc R U . . .
C21 C 0.4956(2) 0.44420(14) 0.82778(12) 0.0550(3) Uani 1 1 d . . . . .
H21A H 0.481219 0.361017 0.849524 0.082 Uiso 1 1 calc R U . . .
H21B H 0.444898 0.503501 0.881067 0.082 Uiso 1 1 calc R U . . .
H21C H 0.626151 0.487520 0.836707 0.082 Uiso 1 1 calc R U . . .
C22 C 0.1506(2) 0.11605(13) 0.41438(14) 0.0638(4) Uani 1 1 d . . . . .
H22A H 0.023138 0.079791 0.418262 0.096 Uiso 1 1 calc R U . . .
H22B H 0.224193 0.061783 0.440965 0.096 Uiso 1 1 calc R U . . .
H22C H 0.155569 0.114767 0.331121 0.096 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 131.70(10) . . ?
C9 N1 C10 108.71(9) . . ?
C18 N1 C10 119.37(10) . . ?
C19 N3 C10 117.85(10) . . ?
C2 C1 C6 117.50(11) . . ?
C2 C1 C7 121.40(11) . . ?
C6 C1 C7 121.06(11) . . ?
C3 C2 C1 120.78(12) . . ?
C4 C3 C2 121.02(13) . . ?
C3 C4 C5 119.16(12) . . ?
C4 C5 C6 120.40(13) . . ?
C5 C6 C1 121.12(13) . . ?
C10 C7 C8 104.85(10) . . ?
C10 C7 C1 126.93(11) . . ?
C8 C7 C1 128.19(10) . . ?
C9 C8 C7 111.00(10) . . ?
C9 C8 C11 121.28(11) . . ?
C7 C8 C11 127.71(11) . . ?
N1 C9 C8 106.46(10) . . ?
N1 C9 C12 126.91(10) . . ?
C8 C9 C12 126.58(11) . . ?
N3 C10 C7 128.86(11) . . ?
N3 C10 N1 122.17(10) . . ?
C7 C10 N1 108.97(10) . . ?
N2 C11 C8 179.15(14) . . ?
C13 C12 C17 119.07(13) . . ?
C13 C12 C9 120.65(12) . . ?
C17 C12 C9 120.20(12) . . ?
C14 C13 C12 120.43(16) . . ?
C15 C14 C13 120.12(16) . . ?
C14 C15 C16 120.11(15) . . ?
C15 C16 C17 120.25(17) . . ?
C16 C17 C12 119.97(15) . . ?
C20 C18 N1 116.66(11) . . ?
C20 C18 C21 122.58(11) . . ?
N1 C18 C21 120.77(11) . . ?
N3 C19 C20 121.95(11) . . ?
N3 C19 C22 117.87(12) . . ?
C20 C19 C22 120.18(11) . . ?
C18 C20 C19 121.87(11) . . ?
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 1.3790(14) . ?
N1 C18 1.3924(14) . ?
N1 C10 1.4190(14) . ?
N2 C11 1.1433(16) . ?
N3 C19 1.3103(15) . ?
N3 C10 1.3543(14) . ?
C1 C2 1.3939(17) . ?
C1 C6 1.3960(17) . ?
C1 C7 1.4738(16) . ?
C2 C3 1.3791(18) . ?
C3 C4 1.372(2) . ?
C4 C5 1.377(2) . ?
C5 C6 1.3814(18) . ?
C7 C10 1.3885(15) . ?
C7 C8 1.4211(16) . ?
C8 C9 1.3852(16) . ?
C8 C11 1.4245(16) . ?
C9 C12 1.4748(16) . ?
C12 C13 1.3845(18) . ?
C12 C17 1.3906(19) . ?
C13 C14 1.382(2) . ?
C14 C15 1.370(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.382(2) . ?
C18 C20 1.3487(17) . ?
C18 C21 1.4894(17) . ?
C19 C20 1.4191(18) . ?
C19 C22 1.4989(18) . ?
