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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/1/56/68/1566840.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_1566840
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            'C35 H23 N3'
_chemical_formula_weight         485.56
_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                 116.236(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7978(12)
_cell_length_b                   27.007(2)
_cell_length_c                   10.7502(14)
_cell_measurement_reflns_used    9320
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60.5270
_cell_measurement_theta_min      2.8570
_cell_volume                     2551.6(6)
_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 1.000
_diffrn_measured_fraction_theta_max 0.964
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22817
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         61.289
_diffrn_reflns_theta_min         2.845
_diffrn_source                   'micro-focus metaljet'
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42123
_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            orange
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0011(4)
_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   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0883
_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)+(0.1228P)²+1.8504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2547
_refine_ls_wR_factor_ref         0.2749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4035
_reflns_number_total             5767
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00837h2.cif
_cod_data_source_block           Compound-5-41
_cod_original_cell_volume        2551.5(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1566840
_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 0.7403(3) 0.23086(8) 0.4975(3) 0.0518(6) Uani 1 1 d . . . . .
N2 N 0.9105(3) 0.28287(9) 0.4450(3) 0.0590(6) Uani 1 1 d . . . . .
N3 N 0.4179(4) 0.33276(12) 0.6063(4) 0.0825(9) Uani 1 1 d . . . . .
C1 C 0.6770(4) 0.45215(11) 0.4672(3) 0.0572(7) Uani 1 1 d . . . . .
C2 C 0.8255(4) 0.46951(11) 0.5497(4) 0.0622(8) Uani 1 1 d . . . . .
C3 C 0.8550(5) 0.52039(13) 0.5503(5) 0.0809(11) Uani 1 1 d . . . . .
H3 H 0.952319 0.532140 0.606308 0.097 Uiso 1 1 calc R U . . .
C4 C 0.7452(5) 0.55288(13) 0.4714(5) 0.0809(11) Uani 1 1 d . . . . .
H4 H 0.767324 0.586405 0.472212 0.097 Uiso 1 1 calc R U . . .
C5 C 0.5999(5) 0.53549(14) 0.3896(5) 0.0829(11) Uani 1 1 d . . . . .
H5 H 0.524333 0.557642 0.335257 0.099 Uiso 1 1 calc R U . . .
C6 C 0.5655(4) 0.48662(13) 0.3872(4) 0.0783(10) Uani 1 1 d . . . . .
H6 H 0.466740 0.475898 0.331755 0.094 Uiso 1 1 calc R U . . .
C7 C 0.6473(4) 0.40086(11) 0.4645(4) 0.0583(7) Uani 1 1 d . . . . .
H7 H 0.548185 0.389631 0.413332 0.070 Uiso 1 1 calc R U . . .
C8 C 0.7588(3) 0.36739(11) 0.5341(3) 0.0553(7) Uani 1 1 d . . . . .
C9 C 0.9082(4) 0.38503(13) 0.6149(4) 0.0707(9) Uani 1 1 d . . . . .
H9 H 0.986176 0.362673 0.662791 0.085 Uiso 1 1 calc R U . . .
C10 C 0.9390(4) 0.43416(13) 0.6233(4) 0.0776(11) Uani 1 1 d . . . . .
H10 H 1.037596 0.444922 0.679023 0.093 Uiso 1 1 calc R U . . .
C11 C 0.7289(3) 0.31367(10) 0.5275(3) 0.0538(7) Uani 1 1 d . . . . .
C12 C 0.8027(3) 0.27746(11) 0.4904(3) 0.0533(7) Uani 1 1 d . . . . .
C13 C 0.6219(3) 0.23804(11) 0.5336(3) 0.0526(7) Uani 1 1 d . . . . .
C14 C 0.6169(3) 0.28884(11) 0.5526(3) 0.0544(7) Uani 1 1 d . . . . .
C15 C 0.9621(3) 0.24310(11) 0.4107(4) 0.0581(7) Uani 1 1 d . . . . .
C16 C 0.9150(4) 0.19527(11) 0.4300(3) 0.0588(7) Uani 1 1 d . . . . .
H16 H 0.958258 0.167719 0.409344 0.071 Uiso 1 1 calc R U . . .
C17 C 0.8092(3) 0.18827(10) 0.4773(3) 0.0527(7) Uani 1 1 d . . . . .
C18 C 0.5139(3) 0.20035(11) 0.5341(4) 0.0582(8) Uani 1 1 d . . . . .
C19 C 0.4506(4) 0.16488(13) 0.4244(4) 0.0673(9) Uani 1 1 d . . . . .
H19 H 0.478766 0.166186 0.352443 0.081 Uiso 1 1 calc R U . . .
C20 C 0.3509(4) 0.12936(15) 0.4213(4) 0.0740(9) Uani 1 1 d . . . . .
H20 H 0.313988 0.106156 0.350103 0.089 Uiso 1 1 calc R U . . .
C21 C 0.3061(4) 0.12840(13) 0.5250(4) 0.0636(8) Uani 1 1 d . . . . .
C22 C 0.3532(3) 0.16364(13) 0.6303(3) 0.0603(8) Uani 1 1 d . . . . .
C23 C 0.4663(4) 0.20027(12) 0.6334(4) 0.0637(8) Uani 1 1 d . . . . .
H23 H 0.504761 0.223450 0.704646 0.076 Uiso 1 1 calc R U . . .
C24 C 0.5066(4) 0.31271(12) 0.5845(3) 0.0602(8) Uani 1 1 d . . . . .
C25 C 1.0774(4) 0.24932(14) 0.3559(4) 0.0713(9) Uani 1 1 d . . . . .
H25A H 1.070989 0.221846 0.296952 0.107 Uiso 1 1 calc R U . . .
H25B H 1.177410 0.250590 0.431927 0.107 Uiso 1 1 calc R U . . .
H25C H 1.057591 0.279526 0.303736 0.107 Uiso 1 1 calc R U . . .
C26 C 0.7779(3) 0.13891(10) 0.5178(3) 0.0540(7) Uani 1 1 d . . . . .
C27 C 0.7474(4) 0.09954(12) 0.4275(4) 0.0701(9) Uani 1 1 d . . . . .
H27 H 0.742763 0.104462 0.340105 0.084 Uiso 1 1 calc R U . . .
C28 C 0.7237(5) 0.05267(14) 0.4669(5) 0.0881(13) Uani 1 1 d . . . . .
H28 H 0.703427 0.026099 0.406260 0.106 Uiso 1 1 calc R U . . .
C29 C 0.7304(5) 0.04573(14) 0.5955(6) 0.0907(13) Uani 1 1 d . . . . .
H29 H 0.710920 0.014563 0.620767 0.109 Uiso 1 1 calc R U . . .
C30 C 0.7653(5) 0.08410(14) 0.6869(5) 0.0764(10) Uani 1 1 d . . . . .
H30 H 0.773532 0.078641 0.775352 0.092 Uiso 1 1 calc R U . . .
C31 C 0.7885(4) 0.13109(12) 0.6487(4) 0.0602(8) Uani 1 1 d . . . . .
H31 H 0.811122 0.157270 0.710906 0.072 Uiso 1 1 calc R U . . .
C32 C 0.2009(4) 0.09020(15) 0.5303(5) 0.0820(11) Uani 1 1 d . . . . .
H32 H 0.167571 0.065224 0.463856 0.098 Uiso 1 1 calc R U . . .
C33 C 0.1539(4) 0.09089(16) 0.6267(5) 0.0835(12) Uani 1 1 d . . . . .
H33 H 0.088080 0.066396 0.628602 0.100 Uiso 1 1 calc R U . . .
C34 C 0.2034(5) 0.12934(17) 0.7299(5) 0.0849(12) Uani 1 1 d . . . . .
H34 H 0.168997 0.129638 0.797837 0.102 Uiso 1 1 calc R U . . .
C35 C 0.3002(4) 0.16527(15) 0.7289(4) 0.0722(9) Uani 1 1 d . . . . .
H35 H 0.330092 0.190605 0.794208 0.087 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'
N N 0.0241 0.0134 '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'
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
C13 N1 C17 132.7(2) . . ?
C13 N1 C12 109.0(2) . . ?
C17 N1 C12 118.2(2) . . ?
C15 N2 C12 118.3(3) . . ?
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 122.7(3) . . ?
C2 C1 C7 119.1(3) . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 C10 123.3(3) . . ?
C1 C2 C10 117.8(3) . . ?
C4 C3 C2 121.7(4) . . ?
C3 C4 C5 119.1(4) . . ?
C6 C5 C4 121.2(4) . . ?
C5 C6 C1 120.8(4) . . ?
C8 C7 C1 122.1(3) . . ?
C7 C8 C9 118.4(3) . . ?
C7 C8 C11 122.2(3) . . ?
C9 C8 C11 119.4(3) . . ?
C10 C9 C8 120.7(3) . . ?
C9 C10 C2 121.9(3) . . ?
C12 C11 C14 105.7(3) . . ?
C12 C11 C8 126.4(3) . . ?
C14 C11 C8 127.8(3) . . ?
N2 C12 C11 128.5(3) . . ?
N2 C12 N1 122.7(3) . . ?
C11 C12 N1 108.7(2) . . ?
N1 C13 C14 105.5(2) . . ?
N1 C13 C18 126.6(3) . . ?
C14 C13 C18 127.6(3) . . ?
C13 C14 C11 111.1(3) . . ?
C13 C14 C24 124.1(3) . . ?
C11 C14 C24 124.6(3) . . ?
N2 C15 C16 121.1(3) . . ?
N2 C15 C25 118.2(3) . . ?
C16 C15 C25 120.7(3) . . ?
C17 C16 C15 122.3(3) . . ?
C16 C17 N1 116.5(3) . . ?
C16 C17 C26 122.0(3) . . ?
N1 C17 C26 121.3(3) . . ?
C23 C18 C19 118.6(3) . . ?
C23 C18 C13 120.6(3) . . ?
C19 C18 C13 120.7(3) . . ?
C20 C19 C18 122.5(4) . . ?
C19 C20 C21 118.7(4) . . ?
C20 C21 C22 122.6(3) . . ?
C20 C21 C32 121.7(4) . . ?
C22 C21 C32 115.6(3) . . ?
C35 C22 C21 123.2(3) . . ?
C35 C22 C23 119.9(3) . . ?
C21 C22 C23 116.9(3) . . ?
C18 C23 C22 120.4(3) . . ?
N3 C24 C14 177.7(4) . . ?
C27 C26 C31 119.6(3) . . ?
C27 C26 C17 119.8(3) . . ?
C31 C26 C17 120.5(3) . . ?
C26 C27 C28 120.1(4) . . ?
C29 C28 C27 119.6(4) . . ?
C30 C29 C28 120.6(4) . . ?
C29 C30 C31 120.3(4) . . ?
C26 C31 C30 119.6(3) . . ?
C33 C32 C21 121.1(4) . . ?
C32 C33 C34 120.3(4) . . ?
C35 C34 C33 120.5(4) . . ?
C34 C35 C22 119.1(4) . . ?
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 C13 1.390(4) . ?
N1 C17 1.398(4) . ?
N1 C12 1.416(4) . ?
N2 C15 1.307(4) . ?
N2 C12 1.353(4) . ?
N3 C24 1.133(4) . ?
C1 C6 1.404(5) . ?
C1 C2 1.408(5) . ?
C1 C7 1.413(4) . ?
C2 C3 1.404(5) . ?
C2 C10 1.412(5) . ?
C3 C4 1.357(6) . ?
C4 C5 1.383(6) . ?
C5 C6 1.360(5) . ?
C7 C8 1.360(4) . ?
C8 C9 1.414(5) . ?
C8 C11 1.476(4) . ?
C9 C10 1.355(5) . ?
C11 C12 1.376(4) . ?
C11 C14 1.410(4) . ?
C13 C14 1.391(4) . ?
C13 C18 1.470(4) . ?
C14 C24 1.425(4) . ?
C15 C16 1.417(4) . ?
C15 C25 1.496(4) . ?
C16 C17 1.355(4) . ?
C17 C26 1.476(4) . ?
C18 C23 1.341(5) . ?
C18 C19 1.430(5) . ?
C19 C20 1.359(5) . ?
C20 C21 1.367(5) . ?
C21 C22 1.393(5) . ?
C21 C32 1.477(5) . ?
C22 C35 1.372(5) . ?
C22 C23 1.474(5) . ?
C26 C27 1.380(5) . ?
C26 C31 1.381(4) . ?
C27 C28 1.387(5) . ?
C28 C29 1.367(6) . ?
C29 C30 1.364(6) . ?
C30 C31 1.383(5) . ?
C32 C33 1.308(6) . ?
C33 C34 1.438(7) . ?
C34 C35 1.360(5) . ?
