#------------------------------------------------------------------------------
#$Date: 2024-01-06 11:26:01 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288869 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159607.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_7159607
loop_
_publ_author_name
'Qiu, Yi-Feng'
'Cao, Jian-He'
'Wang, Shutao'
'Wang, Qiang'
'Li, Ming'
'Wang, Jun-Jiao'
'Quan, Zheng-Jun'
'Wang, Xi-Cun'
_publ_section_title
;
 Synthesis of 3(2H)-furanone derivatives:
 p-TsOH/halotrimethylsilane promoted cycloketonization of
 γ-hydroxyl ynones.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8744
_journal_page_last               8748
_journal_paper_doi               10.1039/d3ob01500a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H15 N3 O2'
_chemical_formula_sum            'C22 H15 N3 O2'
_chemical_formula_weight         353.37
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-04
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-05-24 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.134(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7255(2)
_cell_length_b                   19.0167(4)
_cell_length_c                   8.36520(18)
_cell_measurement_reflns_used    8452
_cell_measurement_temperature    295.77(10)
_cell_measurement_theta_max      76.9540
_cell_measurement_theta_min      2.3290
_cell_volume                     1800.58(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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_environment      air
_diffrn_ambient_temperature      295.77(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00 105.00   0.50    0.05    --   47.57  28.00  93.00   90
  2  ω     97.00 133.00   0.50    0.05    --  107.75  28.00  93.00   72
  3  ω     98.00 175.00   0.50    0.05    --  107.75  37.00-180.00  154
  4  ω     38.00  63.00   0.50    0.05    --  107.75 -57.00 150.00   50
  5  ω     37.00  63.00   0.50    0.05    --  107.75 -77.00 120.00   52
  6  ω     78.00 103.00   0.50    0.05    --  107.75 -77.00 120.00   50
  7  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00 -30.00   50
  8  ω    -18.00  30.00   0.50    0.05    --   47.57 -28.00 -67.00   96
  9  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00  30.00   50
 10  ω     35.00  61.00   0.50    0.05    --  107.75 -57.00-120.00   52
 11  ω     53.00  79.00   0.50    0.05    --  107.75 -77.00-180.00   52
 12  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00-150.00   50
 13  ω    -93.00 -26.00   0.50    0.05    --  -47.57 125.00-120.00  134
 14  ω    -74.00 -28.00   0.50    0.05    -- -100.00  77.00 -90.00   92
 15  ω   -109.00 -62.00   0.50    0.05    -- -100.00  77.00  60.00   94
 16  ω    -67.00 -28.00   0.50    0.05    -- -100.00  57.00  30.00   78
 17  ω    -69.00 -36.00   0.50    0.05    -- -100.00  57.00  90.00   66
 18  ω    -68.00 -33.00   0.50    0.05    -- -100.00  57.00   0.00   70
 19  ω    -69.00 -28.00   0.50    0.05    -- -100.00  57.00 -90.00   82
 20  ω    -62.00 -36.00   0.50    0.05    -- -100.00  57.00-120.00   52
 21  ω   -174.00 -99.00   0.50    0.05    -- -100.00 -28.00 -67.00  150
 22  ω   -122.00 -50.00   0.50    0.05    --  -47.57 -28.00 -67.00  144
 23  ω     35.00 109.00   0.50    0.05    --  107.75-125.00-180.00  148
 24  ω    -31.00  26.00   0.50    0.05    --  -47.57  28.00  93.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0859237000
_diffrn_orient_matrix_UB_12      0.0291464000
_diffrn_orient_matrix_UB_13      0.0950422000
_diffrn_orient_matrix_UB_21      -0.0969373000
_diffrn_orient_matrix_UB_22      0.0065094000
_diffrn_orient_matrix_UB_23      -0.1638925000
_diffrn_orient_matrix_UB_31      -0.0417105000
_diffrn_orient_matrix_UB_32      -0.0753075000
_diffrn_orient_matrix_UB_33      0.0226308000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11937
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.300
_diffrn_reflns_theta_min         4.546
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0488
_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)+(0.0754P)²+0.2758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3236
_reflns_number_total             3640
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01500a2.cif
_cod_data_source_block           exp_51_auto
_cod_depositor_comments
'Adding full bibliography for 7159607--7159608.cif.'
_cod_original_cell_volume        1800.58(7)
_cod_database_code               7159607
_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.
;
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.092
_oxdiff_exptl_absorpt_empirical_full_min 0.533
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
O1 O 0.35210(7) 0.66826(5) 0.68244(11) 0.0427(2) Uani 1 1 d . . . . .
O2 O 0.32849(8) 0.49236(5) 0.80580(12) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.69072(11) 0.64523(7) 0.9911(2) 0.0634(4) Uani 1 1 d . . . . .
N2 N 0.78778(11) 0.64173(8) 1.0947(2) 0.0661(4) Uani 1 1 d . . . . .
N3 N 0.87379(14) 0.63132(11) 1.1873(3) 0.0968(6) Uani 1 1 d . . . . .
C1 C 0.45047(10) 0.65705(7) 0.80860(15) 0.0392(3) Uani 1 1 d . . . . .
C2 C 0.45689(11) 0.59229(7) 0.87589(16) 0.0420(3) Uani 1 1 d . . . . .
H2 H 0.516809 0.575893 0.964124 0.050 Uiso 1 1 calc R . . . .
C3 C 0.26832(11) 0.58030(7) 0.48107(15) 0.0419(3) Uani 1 1 d . . . . .
C4 C 0.28168(10) 0.60410(6) 0.65809(15) 0.0378(3) Uani 1 1 d . . . . .
C5 C 0.35598(11) 0.55325(6) 0.78850(15) 0.0381(3) Uani 1 1 d . . . . .
C6 C 0.52877(11) 0.71833(7) 0.84642(16) 0.0427(3) Uani 1 1 d . . . . .
C7 C 0.64655(12) 0.71305(7) 0.94045(18) 0.0478(3) Uani 1 1 d . . . . .
C8 C 0.16413(10) 0.61835(7) 0.69737(15) 0.0411(3) Uani 1 1 d . . . . .
C9 C 0.48563(14) 0.78461(7) 0.7891(2) 0.0538(4) Uani 1 1 d . . . . .
H9 H 0.408077 0.788938 0.725323 0.065 Uiso 1 1 calc R . . . .
C10 C 0.33538(13) 0.52616(9) 0.44312(19) 0.0563(4) Uani 1 1 d . . . . .
H10 H 0.389327 0.502721 0.527615 0.068 Uiso 1 1 calc R . . . .
C11 C 0.08214(13) 0.56421(9) 0.6751(2) 0.0553(4) Uani 1 1 d . . . . .
H11 H 0.099273 0.520833 0.635510 0.066 Uiso 1 1 calc R . . . .
C12 C 0.71632(14) 0.77303(9) 0.9747(2) 0.0616(4) Uani 1 1 d . . . . .
H12 H 0.794450 0.769401 1.036738 0.074 Uiso 1 1 calc R . . . .
C13 C 0.13741(14) 0.68208(8) 0.7570(2) 0.0564(4) Uani 1 1 d . . . . .
H13 H 0.191779 0.718716 0.773305 0.068 Uiso 1 1 calc R . . . .
C14 C 0.67096(16) 0.83761(9) 0.9179(3) 0.0697(5) Uani 1 1 d . . . . .
H14 H 0.718348 0.877441 0.942268 0.084 Uiso 1 1 calc R . . . .
C15 C 0.55542(16) 0.84371(8) 0.8248(2) 0.0666(5) Uani 1 1 d . . . . .
H15 H 0.524885 0.887514 0.786519 0.080 Uiso 1 1 calc R . . . .
C16 C 0.18943(16) 0.61421(10) 0.35270(19) 0.0653(4) Uani 1 1 d . . . . .
H16 H 0.143230 0.650663 0.375605 0.078 Uiso 1 1 calc R . . . .
C17 C 0.02916(15) 0.69162(10) 0.7928(2) 0.0690(5) Uani 1 1 d . . . . .
H17 H 0.011484 0.734782 0.832773 0.083 Uiso 1 1 calc R . . . .
C18 C -0.05127(14) 0.63849(11) 0.7700(2) 0.0667(5) Uani 1 1 d . . . . .
H18 H -0.123610 0.645401 0.793803 0.080 Uiso 1 1 calc R . . . .
C19 C -0.02511(14) 0.57470(11) 0.7116(2) 0.0666(5) Uani 1 1 d . . . . .
H19 H -0.079804 0.538267 0.696546 0.080 Uiso 1 1 calc R . . . .
C20 C 0.24459(19) 0.54052(14) 0.1544(2) 0.0818(6) Uani 1 1 d . . . . .
H20 H 0.236276 0.527089 0.045084 0.098 Uiso 1 1 calc R . . . .
C21 C 0.32265(16) 0.50658(12) 0.2796(2) 0.0745(5) Uani 1 1 d . . . . .
H21 H 0.367895 0.469910 0.255417 0.089 Uiso 1 1 calc R . . . .
C22 C 0.1786(2) 0.59444(13) 0.1905(2) 0.0861(6) Uani 1 1 d . . . . .
H22 H 0.125786 0.618087 0.105031 0.103 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 C4 108.15(9) . . ?
N2 N1 C7 117.16(13) . . ?
N3 N2 N1 172.9(2) . . ?
O1 C1 C6 113.51(11) . . ?
C2 C1 O1 114.23(11) . . ?
C2 C1 C6 132.26(12) . . ?
C1 C2 C5 108.25(11) . . ?
C10 C3 C4 121.77(12) . . ?
C16 C3 C4 119.83(13) . . ?
C16 C3 C10 118.37(14) . . ?
O1 C4 C3 107.25(10) . . ?
O1 C4 C5 103.34(9) . . ?
O1 C4 C8 109.42(10) . . ?
C3 C4 C5 113.46(10) . . ?
C3 C4 C8 113.28(10) . . ?
C8 C4 C5 109.53(10) . . ?
O2 C5 C2 129.98(12) . . ?
O2 C5 C4 124.03(11) . . ?
C2 C5 C4 105.99(10) . . ?
C7 C6 C1 122.24(12) . . ?
C9 C6 C1 119.56(12) . . ?
C9 C6 C7 118.20(12) . . ?
C6 C7 N1 117.60(12) . . ?
C12 C7 N1 122.52(13) . . ?
C12 C7 C6 119.83(13) . . ?
C11 C8 C4 118.26(12) . . ?
C13 C8 C4 122.62(12) . . ?
C13 C8 C11 119.11(13) . . ?
C15 C9 C6 121.41(14) . . ?
C3 C10 C21 120.35(16) . . ?
C19 C11 C8 120.06(15) . . ?
C14 C12 C7 120.59(15) . . ?
C8 C13 C17 119.97(15) . . ?
C12 C14 C15 120.34(14) . . ?
C9 C15 C14 119.63(15) . . ?
C3 C16 C22 120.54(18) . . ?
C18 C17 C13 120.75(16) . . ?
C17 C18 C19 119.69(15) . . ?
C18 C19 C11 120.43(16) . . ?
C21 C20 C22 119.52(17) . . ?
C20 C21 C10 120.61(19) . . ?
C20 C22 C16 120.60(18) . . ?
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
O1 C1 1.3616(14) . ?
O1 C4 1.4575(14) . ?
O2 C5 1.2206(15) . ?
N1 N2 1.2392(18) . ?
N1 C7 1.4131(19) . ?
N2 N3 1.117(2) . ?
C1 C2 1.3479(18) . ?
C1 C6 1.4661(17) . ?
C2 C5 1.4261(17) . ?
C3 C4 1.5169(17) . ?
C3 C10 1.382(2) . ?
C3 C16 1.381(2) . ?
C4 C5 1.5452(16) . ?
C4 C8 1.5225(17) . ?
C6 C7 1.4031(19) . ?
C6 C9 1.3958(19) . ?
C7 C12 1.389(2) . ?
C8 C11 1.3875(19) . ?
C8 C13 1.378(2) . ?
C9 C15 1.376(2) . ?
C10 C21 1.387(2) . ?
C11 C19 1.384(2) . ?
C12 C14 1.373(2) . ?
C13 C17 1.390(2) . ?
C14 C15 1.380(3) . ?
C16 C22 1.382(3) . ?
C17 C18 1.361(3) . ?
C18 C19 1.372(3) . ?
C20 C21 1.360(3) . ?
C20 C22 1.365(3) . ?
