#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:57:01 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159306.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_7159306
loop_
_publ_author_name
'Nam, Seonghyeon'
'Lee, Sunhee'
'Kim, Woojin'
'Kim, Ikyon'
_publ_section_title
;
 Divergent synthesis of two types of indolizines from
 pyridine-2-acetonitrile, (hetero)arylglyoxal, and TMSCN.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3881
_journal_page_last               3895
_journal_paper_doi               10.1039/d3ob00471f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C15 H10 N2 O'
_chemical_formula_weight         234.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1137(8)
_cell_length_b                   9.2789(7)
_cell_length_c                   21.5088(15)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.0967
_cell_measurement_theta_min      2.3893
_cell_volume                     2417.6(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2019.11.0.3'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            95310
_diffrn_reflns_theta_full        28.17
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0468
_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)+(0.0383P)²+0.9253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2186
_reflns_number_total             2964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00471f2.cif
_cod_data_source_block           KWJ2143
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159305--7159306.cif.
;
_cod_database_code               7159306
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.31248(9) 0.67997(12) 0.41921(6) 0.0580(3) Uani d . . . 1 . .
N N1 0.28550(10) 0.29862(15) 0.25472(6) 0.0529(3) Uani d . . . 1 . .
C C9 0.23456(12) 0.45606(16) 0.33810(6) 0.0417(3) Uani d . . . 1 . .
C C11 0.20225(11) 0.35391(16) 0.28813(7) 0.0421(3) Uani d . . . 1 . .
C C6 0.49344(12) 0.58556(16) 0.42001(6) 0.0423(3) Uani d . . . 1 . .
C C7 0.37668(12) 0.59056(16) 0.39897(6) 0.0432(3) Uani d . . . 1 . .
C C8 0.33982(12) 0.48636(16) 0.35091(7) 0.0450(3) Uani d . . . 1 . .
H H8 0.393928 0.438811 0.328098 0.054 Uiso calc U . R 1 . .
C C12 0.09301(12) 0.31870(17) 0.27673(7) 0.0494(4) Uani d . . . 1 . .
H H12 0.036802 0.359557 0.300323 0.059 Uiso calc U . R 1 . .
C C5 0.56359(13) 0.47308(19) 0.40527(8) 0.0534(4) Uani d . . . 1 . .
H H5 0.538498 0.397585 0.380588 0.064 Uiso calc U . R 1 . .
C C10 0.14459(13) 0.51887(18) 0.37268(8) 0.0521(4) Uani d . . . 1 . .
C C1 0.53208(14) 0.69590(18) 0.45781(8) 0.0558(4) Uani d . . . 1 . .
H H1 0.485578 0.771762 0.468417 0.067 Uiso calc U . R 1 . .
N N2 0.06729(13) 0.5606(2) 0.39660(8) 0.0806(5) Uani d . . . 1 . .
C C14 0.15306(14) 0.16503(19) 0.19563(8) 0.0582(4) Uani d . . . 1 . .
H H14 0.139053 0.099912 0.163724 0.07 Uiso calc U . R 1 . .
C C13 0.06870(13) 0.22216(19) 0.22987(8) 0.0565(4) Uani d . . . 1 . .
H H13 -0.004056 0.196361 0.221706 0.068 Uiso calc U . R 1 . .
C C15 0.25934(15) 0.2064(2) 0.20964(8) 0.0590(4) Uani d . . . 1 . .
H H15 0.316463 0.167546 0.186119 0.071 Uiso calc U . R 1 . .
C C4 0.67104(15) 0.4725(2) 0.42714(9) 0.0644(5) Uani d . . . 1 . .
H H4 0.718315 0.397333 0.416724 0.077 Uiso calc U . R 1 . .
C C3 0.70780(15) 0.5828(2) 0.46415(8) 0.0659(5) Uani d . . . 1 . .
H H3 0.780056 0.582236 0.478769 0.079 Uiso calc U . R 1 . .
C C2 0.63885(16) 0.6936(2) 0.47967(8) 0.0655(5) Uani d . . . 1 . .
H H2 0.664121 0.767635 0.505083 0.079 Uiso calc U . R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 N1 C11 . . 117.22(14) ?
C8 C9 C10 . . 122.03(14) ?
C8 C9 C11 . . 122.38(13) ?
C10 C9 C11 . . 115.58(13) ?
N1 C11 C12 . . 122.26(14) ?
N1 C11 C9 . . 115.71(12) ?
C12 C11 C9 . . 122.03(13) ?
C5 C6 C1 . . 118.92(14) ?
C5 C6 C7 . . 122.60(14) ?
C1 C6 C7 . . 118.44(14) ?
O1 C7 C8 . . 120.06(14) ?
O1 C7 C6 . . 121.35(14) ?
C8 C7 C6 . . 118.57(13) ?
C9 C8 C7 . . 124.64(14) ?
C9 C8 H8 . . 117.7 ?
C7 C8 H8 . . 117.7 ?
C13 C12 C11 . . 119.10(15) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C6 C5 C4 . . 120.19(16) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
N2 C10 C9 . . 173.57(18) ?
C2 C1 C6 . . 120.34(17) ?
C2 C1 H1 . . 119.8 ?
C6 C1 H1 . . 119.8 ?
C13 C14 C15 . . 118.23(15) ?
C13 C14 H14 . . 120.9 ?
C15 C14 H14 . . 120.9 ?
C14 C13 C12 . . 119.06(15) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
N1 C15 C14 . . 124.14(16) ?
N1 C15 H15 . . 117.9 ?
C14 C15 H15 . . 117.9 ?
C3 C4 C5 . . 120.00(18) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C2 C3 C4 . . 120.33(17) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C3 C2 C1 . . 120.21(17) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.2176(18) ?
N1 C15 . 1.331(2) ?
N1 C11 . 1.3403(19) ?
C9 C8 . 1.335(2) ?
C9 C10 . 1.442(2) ?
C9 C11 . 1.486(2) ?
C11 C12 . 1.385(2) ?
C6 C5 . 1.383(2) ?
C6 C1 . 1.389(2) ?
C6 C7 . 1.486(2) ?
C7 C8 . 1.484(2) ?
C8 H8 . 0.93 ?
C12 C13 . 1.380(2) ?
C12 H12 . 0.93 ?
C5 C4 . 1.384(2) ?
C5 H5 . 0.93 ?
C10 N2 . 1.137(2) ?
C1 C2 . 1.376(2) ?
C1 H1 . 0.93 ?
C14 C13 . 1.367(2) ?
C14 C15 . 1.377(2) ?
C14 H14 . 0.93 ?
C13 H13 . 0.93 ?
C15 H15 . 0.93 ?
C4 C3 . 1.371(3) ?
C4 H4 . 0.93 ?
C3 C2 . 1.366(3) ?
C3 H3 . 0.93 ?
C2 H2 . 0.93 ?
