#------------------------------------------------------------------------------
#$Date: 2023-12-07 04:14:00 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288110 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247843.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_7247843
loop_
_publ_author_name
'Luo, Zheng'
'Hu, Huayou'
'Wang, Chao'
'Yang, Zhen'
'Wang, Yefei'
_publ_section_title
;
 A domino reaction for the synthesis of pyrrolo[2,1-a]isoquinolines from
 2-aryl-pyrrolidines and alkynes promoted by a four-component catalytic
 system under aerobic conditions
;
_journal_issue                   50
_journal_name_full               'RSC Advances'
_journal_page_first              35617
_journal_page_last               35620
_journal_paper_doi               10.1039/D3RA07653A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C26 H23 N O6'
_chemical_formula_sum            'C26 H23 N O6'
_chemical_formula_weight         445.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-10-06 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.105(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3722(4)
_cell_length_b                   10.3911(4)
_cell_length_c                   18.8309(8)
_cell_measurement_reflns_used    3927
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.66
_cell_volume                     2212.62(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12879
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_min         2.802
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0441
_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)+(0.0504P)²+1.1565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3034
_reflns_number_total             4045
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra07653a2.cif
_cod_data_source_block           1_CCDC1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7247843
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.21876(16) 0.55662(18) 1.03514(10) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.26528(17) 0.45888(18) 1.07918(10) 0.0231(4) Uani 1 1 d . . . . .
C3 C 0.34250(16) 0.38453(18) 1.04131(10) 0.0222(4) Uani 1 1 d . . . . .
C4 C 0.34263(16) 0.43874(18) 0.97434(10) 0.0212(4) Uani 1 1 d . . . . .
C5 C 0.40280(16) 0.40693(18) 0.91295(10) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.49458(17) 0.31615(19) 0.91718(11) 0.0269(4) Uani 1 1 d . . . . .
H6 H 0.5173 0.2731 0.9610 0.032 Uiso 1 1 calc R U . . .
C7 C 0.55195(17) 0.2891(2) 0.85811(11) 0.0293(5) Uani 1 1 d . . . . .
H7 H 0.6144 0.2279 0.8615 0.035 Uiso 1 1 calc R U . . .
C8 C 0.51903(18) 0.3510(2) 0.79358(12) 0.0318(5) Uani 1 1 d . . . . .
H8 H 0.5582 0.3311 0.7528 0.038 Uiso 1 1 calc R U . . .
C9 C 0.43015(18) 0.4405(2) 0.78874(11) 0.0294(5) Uani 1 1 d . . . . .
H9 H 0.4083 0.4820 0.7443 0.035 Uiso 1 1 calc R U . . .
C10 C 0.37043(17) 0.47252(19) 0.84827(10) 0.0244(4) Uani 1 1 d . . . . .
C11 C 0.28242(17) 0.57439(19) 0.84562(10) 0.0254(4) Uani 1 1 d . . . . .
C12 C 0.23520(17) 0.61172(18) 0.90551(10) 0.0235(4) Uani 1 1 d . . . . .
C13 C 0.13762(17) 0.65947(19) 1.05658(10) 0.0230(4) Uani 1 1 d . . . . .
C14 C -0.05561(19) 0.6958(2) 1.08701(14) 0.0386(6) Uani 1 1 d . . . . .
H14A H -0.0186 0.7403 1.1295 0.058 Uiso 1 1 calc R U . . .
H14B H -0.1235 0.6459 1.0996 0.058 Uiso 1 1 calc R U . . .
H14C H -0.0824 0.7593 1.0503 0.058 Uiso 1 1 calc R U . . .
C15 C 0.24650(17) 0.44855(19) 1.15504(10) 0.0258(4) Uani 1 1 d . . . . .
C16 C 0.3032(2) 0.3351(2) 1.26192(12) 0.0453(6) Uani 1 1 d . . . . .
H16A H 0.3566 0.3987 1.2865 0.068 Uiso 1 1 calc R U . . .
H16B H 0.3290 0.2483 1.2768 0.068 Uiso 1 1 calc R U . . .
H16C H 0.2226 0.3496 1.2741 0.068 Uiso 1 1 calc R U . . .
C17 C 0.40303(17) 0.26373(19) 1.06782(11) 0.0255(4) Uani 1 1 d . . . . .
C18 C 0.3722(3) 0.0427(2) 1.08901(17) 0.0594(8) Uani 1 1 d . . . . .
H18A H 0.4433 0.0191 1.0668 0.089 Uiso 1 1 calc R U . . .
H18B H 0.3118 -0.0239 1.0789 0.089 Uiso 1 1 calc R U . . .
H18C H 0.3920 0.0505 1.1408 0.089 Uiso 1 1 calc R U . . .
C19 C 0.2440(2) 0.6397(2) 0.77517(11) 0.0387(6) Uani 1 1 d . . . . .
H19A H 0.3144 0.6578 0.7501 0.046 Uiso 1 1 calc R U . . .
H19B H 0.2058 0.7229 0.7843 0.046 Uiso 1 1 calc R U . . .
C20 C 0.1575(3) 0.5562(3) 0.72768(14) 0.0604(8) Uani 1 1 d . . . . .
H20A H 0.1938 0.4724 0.7203 0.091 Uiso 1 1 calc R U . . .
H20B H 0.1381 0.5987 0.6815 0.091 Uiso 1 1 calc R U . . .
H20C H 0.0851 0.5438 0.7508 0.091 Uiso 1 1 calc R U . . .
C21 C 0.15585(17) 0.72496(18) 0.90826(10) 0.0234(4) Uani 1 1 d . . . . .
C22 C 0.20551(18) 0.84725(19) 0.91638(11) 0.0288(5) Uani 1 1 d . . . . .
H22 H 0.2890 0.8571 0.9201 0.035 Uiso 1 1 calc R U . . .
C23 C 0.1342(2) 0.9544(2) 0.91910(12) 0.0333(5) Uani 1 1 d . . . . .
H23 H 0.1687 1.0375 0.9250 0.040 Uiso 1 1 calc R U . . .
C24 C 0.01200(19) 0.9409(2) 0.91319(11) 0.0326(5) Uani 1 1 d . . . . .
H24 H -0.0371 1.0145 0.9153 0.039 Uiso 1 1 calc R U . . .
C25 C -0.03773(19) 0.8198(2) 0.90416(12) 0.0332(5) Uani 1 1 d . . . . .
H25 H -0.1213 0.8104 0.8995 0.040 Uiso 1 1 calc R U . . .
C26 C 0.03352(17) 0.7120(2) 0.90189(11) 0.0280(5) Uani 1 1 d . . . . .
H26 H -0.0013 0.6291 0.8960 0.034 Uiso 1 1 calc R U . . .
N1 N 0.26523(13) 0.54446(14) 0.97047(8) 0.0210(4) Uani 1 1 d . . . . .
O1 O 0.02956(11) 0.61021(13) 1.05984(8) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.16637(12) 0.76823(13) 1.07228(7) 0.0282(3) Uani 1 1 d . . . . .
O3 O 0.30519(14) 0.34789(14) 1.18560(8) 0.0353(4) Uani 1 1 d . . . . .
O4 O 0.18797(14) 0.52192(15) 1.18637(8) 0.0371(4) Uani 1 1 d . . . . .
O5 O 0.32715(13) 0.16493(13) 1.06022(9) 0.0380(4) Uani 1 1 d . . . . .
O6 O 0.50448(13) 0.25235(15) 1.09104(9) 0.0437(4) 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C2 C1 N1 107.67(16) . . ?
C2 C1 C13 124.87(17) . . ?
N1 C1 C13 127.39(16) . . ?
C1 C2 C3 108.49(17) . . ?
C1 C2 C15 123.45(17) . . ?
C3 C2 C15 127.63(17) . . ?
C4 C3 C2 107.33(16) . . ?
C4 C3 C17 127.11(18) . . ?
C2 C3 C17 125.36(17) . . ?
C3 C4 N1 107.74(16) . . ?
C3 C4 C5 133.21(18) . . ?
N1 C4 C5 119.05(16) . . ?
C6 C5 C10 119.90(18) . . ?
C6 C5 C4 121.46(18) . . ?
C10 C5 C4 118.60(17) . . ?
C7 C6 C5 120.32(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.34(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.02(19) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 121.43(19) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C9 117.96(18) . . ?
C5 C10 C11 119.82(17) . . ?
C9 C10 C11 122.14(18) . . ?
C12 C11 C10 120.77(18) . . ?
C12 C11 C19 119.85(18) . . ?
C10 C11 C19 119.38(17) . . ?
C11 C12 N1 119.72(17) . . ?
C11 C12 C21 123.41(18) . . ?
N1 C12 C21 116.82(16) . . ?
O2 C13 O1 125.03(18) . . ?
O2 C13 C1 125.29(17) . . ?
O1 C13 C1 109.57(16) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O3 124.03(19) . . ?
O4 C15 C2 125.00(18) . . ?
O3 C15 C2 110.96(17) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 O5 123.31(18) . . ?
O6 C17 C3 126.77(18) . . ?
O5 C17 C3 109.89(16) . . ?
O5 C18 H18A 109.5 . . ?
O5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C19 C20 111.5(2) . . ?
C11 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C11 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 119.24(18) . . ?
C26 C21 C12 121.72(17) . . ?
C22 C21 C12 119.03(17) . . ?
C23 C22 C21 120.44(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 119.63(19) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.44(19) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.14(19) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C1 N1 C4 108.76(15) . . ?
C1 N1 C12 129.37(16) . . ?
C4 N1 C12 121.47(16) . . ?
C13 O1 C14 115.66(16) . . ?
C15 O3 C16 116.08(17) . . ?
C17 O5 C18 115.64(17) . . ?
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
C1 C2 1.380(3) . ?
C1 N1 1.384(2) . ?
C1 C13 1.495(3) . ?
C2 C3 1.418(3) . ?
C2 C15 1.471(3) . ?
C3 C4 1.381(3) . ?
C3 C17 1.492(3) . ?
C4 N1 1.405(2) . ?
C4 C5 1.443(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.410(3) . ?
C6 C7 1.377(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.370(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.411(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.454(3) . ?
C11 C12 1.356(3) . ?
C11 C19 1.513(3) . ?
C12 N1 1.419(2) . ?
C12 C21 1.487(3) . ?
C13 O2 1.205(2) . ?
C13 O1 1.339(2) . ?
C14 O1 1.448(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 O4 1.207(2) . ?
C15 O3 1.338(2) . ?
C16 O3 1.446(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O6 1.195(2) . ?
C17 O5 1.339(2) . ?
C18 O5 1.453(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.527(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.390(3) . ?
C21 C22 1.392(3) . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
