#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:26:46 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249662.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_7249662
loop_
_publ_author_name
'Yuan, Yong'
'Liu, Xincong'
'Zhang, Feng'
'Bai, Chunyan'
'Tao, Yuyan'
'Bao, Xiazhen'
'Ji, Dongsheng'
'Huo, Congde'
_publ_section_title
;
 Electrochemical dehydrogenative annulation for the synthesis of
 4-oxo-oxazolines
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              96
_journal_page_last               101
_journal_paper_doi               10.1039/D4GC05119J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C10 H11 N O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_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             2023-09-21
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.820(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5314(9)
_cell_length_b                   4.1737(2)
_cell_length_c                   14.2425(9)
_cell_measurement_reflns_used    2646
_cell_measurement_temperature    304.23(10)
_cell_measurement_theta_max      30.6690
_cell_measurement_theta_min      2.6100
_cell_volume                     923.15(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.23(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.828
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  61.00   1.00    2.00    --   -6.19   5.00 124.00   80
  2  ω      2.00  32.00   1.00    2.00    --    4.16 -99.00 -30.00   30
  3  ω    -61.00   9.00   1.00    2.00    --   -6.19 -57.00 -90.00   70
  4  ω    -75.00 -50.00   1.00    2.00    --   -6.19  -5.00 -52.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0405773000
_diffrn_orient_matrix_UB_12      0.0085642000
_diffrn_orient_matrix_UB_13      -0.0221099000
_diffrn_orient_matrix_UB_21      0.0207949000
_diffrn_orient_matrix_UB_22      0.0065127000
_diffrn_orient_matrix_UB_23      0.0446202000
_diffrn_orient_matrix_UB_31      0.0028575000
_diffrn_orient_matrix_UB_32      -0.1696396000
_diffrn_orient_matrix_UB_33      0.0005967000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.828
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7692
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.382
_diffrn_reflns_theta_min         2.623
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2294
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0455
_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)+(0.0703P)²+0.1315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1515
_reflns_number_total             2294
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc05119j2.cif
_cod_data_source_block           liuxc_0921_auto
_cod_depositor_comments          'Adding full bibliography for 7249662.cif.'
_cod_original_cell_volume        923.14(10)
_cod_database_code               7249662
_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   0.990
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.787
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 0.31747(7) 0.1778(3) 0.66454(7) 0.0655(3) Uani 1 1 d . . . . .
O2 O 0.52201(6) 0.1063(3) 0.62898(7) 0.0627(3) Uani 1 1 d . . . . .
H2 H 0.552330 0.074133 0.583274 0.094 Uiso 1 1 calc R U . . .
N1 N 0.39467(7) 0.0369(3) 0.53876(8) 0.0557(3) Uani 1 1 d . . . . .
C1 C 0.26050(9) 0.3352(3) 0.51497(10) 0.0517(4) Uani 1 1 d . . . . .
C2 C 0.26719(10) 0.3544(4) 0.41853(11) 0.0673(4) Uani 1 1 d . . . . .
H2A H 0.314950 0.267408 0.389237 0.081 Uiso 1 1 calc R U . . .
C3 C 0.20371(11) 0.5011(5) 0.36528(12) 0.0739(5) Uani 1 1 d . . . . .
H3 H 0.209313 0.510961 0.300416 0.089 Uiso 1 1 calc R U . . .
C4 C 0.13200(10) 0.6338(4) 0.40623(13) 0.0656(4) Uani 1 1 d . . . . .
C5 C 0.12580(10) 0.6149(4) 0.50230(13) 0.0718(5) Uani 1 1 d . . . . .
H5 H 0.078065 0.702806 0.531410 0.086 Uiso 1 1 calc R U . . .
C6 C 0.18896(10) 0.4683(4) 0.55663(12) 0.0653(4) Uani 1 1 d . . . . .
H6 H 0.183291 0.459037 0.621489 0.078 Uiso 1 1 calc R U . . .
C7 C 0.06274(13) 0.7922(5) 0.34688(15) 0.0899(6) Uani 1 1 d . . . . .
H7A H 0.008448 0.775078 0.377858 0.135 Uiso 1 1 calc R U . . .
H7B H 0.059016 0.687963 0.286867 0.135 Uiso 1 1 calc R U . . .
H7C H 0.076763 1.014127 0.338187 0.135 Uiso 1 1 calc R U . . .
C8 C 0.32793(9) 0.1750(3) 0.57046(9) 0.0508(3) Uani 1 1 d . . . . .
C9 C 0.38870(11) -0.0053(5) 0.70355(12) 0.0673(4) Uani 1 1 d . . . . .
H9A H 0.368530 -0.203697 0.731095 0.081 Uiso 1 1 calc R U . . .
H9B H 0.419414 0.116951 0.751278 0.081 Uiso 1 1 calc R U . . .
C10 C 0.44608(10) -0.0719(4) 0.61999(10) 0.0573(4) Uani 1 1 d . . . . .
H10 H 0.458839 -0.301245 0.615130 0.069 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 0.0033 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
C8 O1 C9 105.87(11) . . ?
C8 N1 C10 107.25(12) . . ?
C2 C1 C6 118.40(14) . . ?
C2 C1 C8 119.98(13) . . ?
C6 C1 C8 121.62(13) . . ?
C3 C2 C1 120.62(15) . . ?
C2 C3 C4 121.37(16) . . ?
C3 C4 C7 120.75(17) . . ?
C5 C4 C3 117.76(15) . . ?
C5 C4 C7 121.49(16) . . ?
C4 C5 C6 121.51(15) . . ?
C1 C6 C5 120.34(15) . . ?
O1 C8 C1 115.82(12) . . ?
N1 C8 O1 117.72(13) . . ?
N1 C8 C1 126.46(13) . . ?
O1 C9 C10 104.41(12) . . ?
O2 C10 N1 110.84(13) . . ?
O2 C10 C9 109.48(12) . . ?
N1 C10 C9 103.98(12) . . ?
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 C8 1.3520(16) . ?
O1 C9 1.4489(18) . ?
O2 C10 1.3986(18) . ?
N1 C8 1.2743(17) . ?
N1 C10 1.4684(19) . ?
C1 C2 1.381(2) . ?
C1 C6 1.383(2) . ?
C1 C8 1.465(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.375(2) . ?
C4 C7 1.511(2) . ?
C5 C6 1.383(2) . ?
C9 C10 1.523(2) . ?
