#------------------------------------------------------------------------------
#$Date: 2022-10-28 03:47:08 +0300 (Fri, 28 Oct 2022) $
#$Revision: 278847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158955.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_7158955
loop_
_publ_author_name
'Zhang, You-Ya'
'Li, Lin'
'Ma, Ai-Jun'
'Wang, Wei-Feng'
'Peng, Jin-Bao'
_publ_section_title
;
 Base-promoted [4+2] Annulation of Pyrrole-2-carbaldehyde Derivatives with
 β,γ-Unsaturated α-Ketoesters : Syntheses of 5,6-Dihydroindolizines
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01903E
_journal_year                    2022
_chemical_formula_moiety         'C28 H21 N O4'
_chemical_formula_sum            'C28 H21 N O4'
_chemical_formula_weight         435.46
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-16 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.870(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1241(6)
_cell_length_b                   12.2852(5)
_cell_length_c                   14.9183(7)
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    160
_cell_measurement_theta_max      24.933
_cell_measurement_theta_min      2.612
_cell_volume                     2195.46(17)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      160.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17130
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.158
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1023 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.9109. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0572
_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)+(0.0486P)²+0.3706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             4472
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01903e2.cif
_cod_data_source_block           0314zyy210921_0m
_cod_database_code               7158955
_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.
;
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C11(H11), C18(H18), C19(H19), C23(H23), C00L(H00L), C7(H7),
 C24(H24), C16(H16), C15(H15), C6(H6), C14(H14), C13(H13), C5(H5), C3(H3),
 C4(H4)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O3 O 0.33408(14) 0.35425(13) 0.41580(11) 0.0347(4) Uani 1 1 d . . . . .
O2 O 0.24567(15) 0.17188(14) 0.30693(11) 0.0433(5) Uani 1 1 d . . . . .
O1 O 0.18871(15) 0.13707(15) 0.44002(12) 0.0475(5) Uani 1 1 d . . . . .
O4 O 0.69697(15) 0.11386(14) 0.52709(13) 0.0469(5) Uani 1 1 d . . . . .
N1 N 0.57678(16) 0.14713(15) 0.65963(12) 0.0286(5) Uani 1 1 d . . . . .
C20 C 0.42160(19) 0.21859(18) 0.51401(15) 0.0271(5) Uani 1 1 d . . . . .
C21 C 0.41994(19) 0.11431(18) 0.54317(15) 0.0278(6) Uani 1 1 d . . . . .
H21 H 0.368580 0.064415 0.510919 0.033 Uiso 1 1 calc R . . . .
C26 C 0.34059(19) 0.25850(18) 0.44089(15) 0.0259(5) Uani 1 1 d . . . . .
C10 C 0.44970(19) 0.37143(18) 0.62930(15) 0.0256(5) Uani 1 1 d . . . . .
C9 C 0.50275(18) 0.30066(17) 0.56327(15) 0.0260(5) Uani 1 1 d . . . . .
H9 H 0.526616 0.349996 0.516512 0.031 Uiso 1 1 calc R . . . .
C17 C 0.3622(2) 0.4989(2) 0.75981(16) 0.0316(6) Uani 1 1 d . . . . .
C11 C 0.4842(2) 0.47686(18) 0.64527(16) 0.0311(6) Uani 1 1 d . . . . .
H11 H 0.536732 0.506906 0.611029 0.037 Uiso 1 1 calc R . . . .
C18 C 0.3240(2) 0.3922(2) 0.73903(16) 0.0346(6) Uani 1 1 d . . . . .
H18 H 0.266550 0.362976 0.768515 0.042 Uiso 1 1 calc R . . . .
C8 C 0.60900(19) 0.24279(18) 0.61276(16) 0.0282(6) Uani 1 1 d . . . . .
H8 H 0.649238 0.294009 0.658675 0.034 Uiso 1 1 calc R . . . .
C27 C 0.2548(2) 0.18235(19) 0.38779(17) 0.0313(6) Uani 1 1 d . . . . .
C19 C 0.3678(2) 0.3300(2) 0.67746(16) 0.0328(6) Uani 1 1 d . . . . .
H19 H 0.342579 0.257294 0.666876 0.039 Uiso 1 1 calc R . . . .
C22 C 0.4926(2) 0.07814(19) 0.62025(16) 0.0294(6) Uani 1 1 d . . . . .
C2 C 0.7551(2) 0.29364(19) 0.50691(16) 0.0313(6) Uani 1 1 d . . . . .
C12 C 0.4438(2) 0.54250(18) 0.71158(16) 0.0308(6) Uani 1 1 d . . . . .
C23 C 0.4969(2) -0.01433(19) 0.67371(16) 0.0348(6) Uani 1 1 d . . . . .
H23 H 0.448476 -0.075403 0.663633 0.042 Uiso 1 1 calc R . . . .
C00L C 0.6341(2) 0.0976(2) 0.73444(16) 0.0350(6) Uani 1 1 d . . . . .
H00L H 0.697177 0.126476 0.772731 0.042 Uiso 1 1 calc R . . . .
C1 C 0.68879(19) 0.20963(19) 0.54624(16) 0.0321(6) Uani 1 1 d . . . . .
C7 C 0.7541(2) 0.4035(2) 0.52849(17) 0.0351(6) Uani 1 1 d . . . . .
H7 H 0.710037 0.427981 0.571920 0.042 Uiso 1 1 calc R . . . .
C24 C 0.5848(2) -0.0017(2) 0.74490(17) 0.0381(6) Uani 1 1 d . . . . .
H24 H 0.606798 -0.052534 0.792277 0.046 Uiso 1 1 calc R . . . .
C16 C 0.3274(2) 0.5622(2) 0.83007(17) 0.0392(7) Uani 1 1 d . . . . .
H16 H 0.272335 0.534254 0.862802 0.047 Uiso 1 1 calc R . . . .
C15 C 0.3719(2) 0.6621(2) 0.85108(18) 0.0423(7) Uani 1 1 d . . . . .
H15 H 0.349130 0.702692 0.899275 0.051 Uiso 1 1 calc R . . . .
C6 C 0.8160(2) 0.4775(2) 0.48790(18) 0.0430(7) Uani 1 1 d . . . . .
H6 H 0.814147 0.552491 0.503233 0.052 Uiso 1 1 calc R . . . .
C14 C 0.4859(3) 0.6483(2) 0.73378(19) 0.0477(8) Uani 1 1 d . . . . .
H14 H 0.539023 0.679516 0.700712 0.057 Uiso 1 1 calc R . . . .
C13 C 0.4507(3) 0.7055(2) 0.80228(19) 0.0493(8) Uani 1 1 d . . . . .
H13 H 0.480306 0.775960 0.817007 0.059 Uiso 1 1 calc R . . . .
C5 C 0.8804(3) 0.4432(2) 0.4254(2) 0.0533(8) Uani 1 1 d . . . . .
H5 H 0.922658 0.494321 0.397130 0.064 Uiso 1 1 calc R . . . .
C3 C 0.8216(3) 0.2604(2) 0.4439(2) 0.0525(8) Uani 1 1 d . . . . .
H3 H 0.824226 0.185549 0.428366 0.063 Uiso 1 1 calc R . . . .
C4 C 0.8835(3) 0.3345(3) 0.4038(2) 0.0658(10) Uani 1 1 d . . . . .
H4 H 0.928664 0.310623 0.360981 0.079 Uiso 1 1 calc R . . . .
C28 C 0.0992(3) 0.0689(3) 0.3937(2) 0.0742(11) Uani 1 1 d . . . . .
H28A H 0.053585 0.111260 0.346155 0.111 Uiso 1 1 calc GR . . . .
H28B H 0.052475 0.043298 0.437528 0.111 Uiso 1 1 calc GR . . . .
H28C H 0.131416 0.006164 0.366461 0.111 Uiso 1 1 calc GR . . . .
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
C27 O1 C28 115.9(2) . . ?
C22 N1 C8 121.76(19) . . ?
C00L N1 C8 127.9(2) . . ?
C00L N1 C22 108.84(19) . . ?
C21 C20 C26 121.6(2) . . ?
C21 C20 C9 120.9(2) . . ?
C26 C20 C9 117.21(19) . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.5(2) . . ?
C22 C21 H21 119.3 . . ?
O3 C26 C20 124.1(2) . . ?
O3 C26 C27 114.9(2) . . ?
C20 C26 C27 121.1(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 C19 118.3(2) . . ?
C19 C10 C9 121.6(2) . . ?
C20 C9 C10 112.61(18) . . ?
C20 C9 H9 107.5 . . ?
C20 C9 C8 110.74(18) . . ?
C10 C9 H9 107.5 . . ?
C10 C9 C8 110.76(18) . . ?
C8 C9 H9 107.5 . . ?
C18 C17 C12 118.2(2) . . ?
C18 C17 C16 123.2(2) . . ?
C12 C17 C16 118.6(2) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.9(2) . . ?
C12 C11 H11 119.1 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(2) . . ?
C19 C18 H18 119.3 . . ?
N1 C8 C9 109.52(18) . . ?
N1 C8 H8 108.6 . . ?
N1 C8 C1 109.75(18) . . ?
C9 C8 H8 108.6 . . ?
C1 C8 C9 111.78(19) . . ?
C1 C8 H8 108.6 . . ?
O2 C27 O1 125.1(2) . . ?
O2 C27 C26 122.5(2) . . ?
O1 C27 C26 112.2(2) . . ?
C10 C19 H19 119.3 . . ?
C18 C19 C10 121.3(2) . . ?
C18 C19 H19 119.3 . . ?
N1 C22 C21 118.7(2) . . ?
C23 C22 N1 107.4(2) . . ?
C23 C22 C21 133.8(2) . . ?
C7 C2 C1 124.0(2) . . ?
C7 C2 C3 118.0(2) . . ?
C3 C2 C1 118.0(2) . . ?
C17 C12 C11 118.8(2) . . ?
C17 C12 C14 118.9(2) . . ?
C14 C12 C11 122.2(2) . . ?
C22 C23 H23 126.2 . . ?
C22 C23 C24 107.7(2) . . ?
C24 C23 H23 126.2 . . ?
N1 C00L H00L 125.9 . . ?
N1 C00L C24 108.2(2) . . ?
C24 C00L H00L 125.9 . . ?
O4 C1 C8 119.2(2) . . ?
O4 C1 C2 120.7(2) . . ?
C2 C1 C8 120.2(2) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C23 C24 H24 126.1 . . ?
C00L C24 C23 107.9(2) . . ?
C00L C24 H24 126.1 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.6 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C13 120.3(2) . . ?
C13 C15 H15 119.8 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C12 C14 H14 119.8 . . ?
C13 C14 C12 120.3(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C13 H13 119.5 . . ?
C14 C13 C15 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C6 C5 H5 120.1 . . ?
C6 C5 C4 119.8(3) . . ?
C4 C5 H5 120.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
O1 C28 H28A 109.5 . . ?
O1 C28 H28B 109.5 . . ?
O1 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
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
O3 C26 1.233(3) . ?
O2 C27 1.201(3) . ?
O1 C27 1.324(3) . ?
O1 C28 1.458(3) . ?
O4 C1 1.218(3) . ?
N1 C8 1.452(3) . ?
N1 C22 1.385(3) . ?
N1 C00L 1.364(3) . ?
C20 C21 1.354(3) . ?
C20 C26 1.437(3) . ?
C20 C9 1.517(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.409(3) . ?
C26 C27 1.526(3) . ?
C10 C9 1.528(3) . ?
C10 C11 1.371(3) . ?
C10 C19 1.407(3) . ?
C9 H9 1.0000 . ?
C9 C8 1.555(3) . ?
C17 C18 1.408(3) . ?
C17 C12 1.415(3) . ?
C17 C16 1.420(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.421(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.364(3) . ?
C8 H8 1.0000 . ?
C8 C1 1.544(3) . ?
C19 H19 0.9500 . ?
C22 C23 1.384(3) . ?
C2 C1 1.484(3) . ?
C2 C7 1.388(3) . ?
C2 C3 1.390(4) . ?
C12 C14 1.417(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(3) . ?
C00L H00L 0.9500 . ?
C00L C24 1.378(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.378(3) . ?
C24 H24 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.358(4) . ?
C15 H15 0.9500 . ?
C15 C13 1.393(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.371(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.362(4) . ?
C13 H13 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
