#------------------------------------------------------------------------------
#$Date: 2021-09-03 22:31:20 +0300 (Fri, 03 Sep 2021) $
#$Revision: 268395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/89/4518963.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_4518963
loop_
_publ_author_name
'Hasani, Morteza'
'Kalhor, Hamid R.'
_publ_section_title
;
 Enzyme-Inspired Lysine-Modified Carbon Quantum Dots Performing
 Carbonylation Using Urea and a Cascade Reaction for Synthesizing
 2-Benzoxazolinone
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10778
_journal_page_last               10788
_journal_paper_doi               10.1021/acscatal.1c01276
_journal_year                    2021
_chemical_formula_moiety         'C7 H5 N O2'
_chemical_formula_sum            'C7 H5 N O2'
_chemical_formula_weight         135.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4456(13)
_cell_length_b                   6.653(4)
_cell_length_c                   21.0100(9)
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.76
_cell_volume                     621.4(4)
_computing_cell_refinement       'automar Data Processing Suite'
_computing_data_collection       'automar Data Processing Suite'
_computing_data_reduction        'automar Data Processing Suite'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL, PLATON (Spek, 2009)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'MAR345 Diffractometer'
_diffrn_measurement_method       'φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.884
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4094
_diffrn_reflns_point_group_measured_fraction_full 0.898
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.879
_diffrn_reflns_theta_min         1.939
_diffrn_standards_decay_%        0.
_diffrn_standards_interval_count 0.
_diffrn_standards_interval_time  0.
_diffrn_standards_number         0.
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scans
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0413
_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)+(0.0431P)²+0.0832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.626
_reflns_Friedel_fraction_full    0.920
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                1046
_reflns_number_total             1081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c01276_si_002.cif
_cod_data_source_block           compound
_cod_database_code               4518963
_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_min   0.987
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.0504(6) 1.0109(4) 0.65083(12) 0.0501(6) Uani 1 1 d . . . . .
C2 C -0.0790(8) 1.1976(4) 0.64493(16) 0.0654(8) Uani 1 1 d . . . . .
H2 H -0.037487 1.300678 0.673522 0.078 Uiso 1 1 calc R U . . .
C3 C -0.2736(8) 1.2245(5) 0.59442(18) 0.0736(10) Uani 1 1 d . . . . .
H3 H -0.365800 1.348805 0.589053 0.088 Uiso 1 1 calc R U . . .
C4 C -0.3350(8) 1.0737(6) 0.55200(16) 0.0718(9) Uani 1 1 d . . . . .
H4 H -0.467288 1.098329 0.518598 0.086 Uiso 1 1 calc R U . . .
C5 C -0.2054(8) 0.8865(6) 0.55766(13) 0.0640(8) Uani 1 1 d . . . . .
H5 H -0.246721 0.783485 0.529026 0.077 Uiso 1 1 calc R U . . .
C6 C -0.0123(6) 0.8603(4) 0.60774(12) 0.0501(6) Uani 1 1 d . . . . .
C7 C 0.3140(7) 0.7351(5) 0.67685(13) 0.0603(8) Uani 1 1 d . . . . .
N3 N 0.2544(6) 0.9266(4) 0.69362(11) 0.0598(7) Uani 1 1 d . . . . .
H3N1 H 0.330815 0.987627 0.725880 0.072 Uiso 1 1 calc R U . . .
O1 O 0.4796(6) 0.6129(4) 0.70124(12) 0.0875(8) Uani 1 1 d . . . . .
O2 O 0.1483(5) 0.6893(3) 0.62376(9) 0.0600(6) 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 C6 120.8(3) . . ?
C2 C1 N3 133.9(3) . . ?
C6 C1 N3 105.2(2) . . ?
C1 C2 C3 116.6(3) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 116.3(3) . . ?
C6 C5 H5 121.8 . . ?
C4 C5 H5 121.8 . . ?
C5 C6 C1 122.6(3) . . ?
C5 C6 O2 127.9(3) . . ?
C1 C6 O2 109.4(2) . . ?
O1 C7 N3 130.0(3) . . ?
O1 C7 O2 121.5(3) . . ?
N3 C7 O2 108.5(3) . . ?
C7 N3 C1 109.8(2) . . ?
C7 N3 H3N1 125.1 . . ?
C1 N3 H3N1 125.1 . . ?
C7 O2 C6 107.0(2) . . ?
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 1.375(4) . ?
C1 C6 1.379(4) . ?
C1 N3 1.395(4) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 O2 1.385(3) . ?
C7 O1 1.210(4) . ?
C7 N3 1.348(5) . ?
C7 O2 1.371(4) . ?
N3 H3N1 0.8600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(4) . . . . ?
N3 C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 O2 -179.3(3) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
N3 C1 C6 C5 -179.7(3) . . . . ?
C2 C1 C6 O2 179.2(3) . . . . ?
N3 C1 C6 O2 0.0(3) . . . . ?
O1 C7 N3 C1 179.3(3) . . . . ?
O2 C7 N3 C1 -0.9(3) . . . . ?
C2 C1 N3 C7 -178.5(3) . . . . ?
C6 C1 N3 C7 0.5(3) . . . . ?
O1 C7 O2 C6 -179.3(3) . . . . ?
N3 C7 O2 C6 0.9(3) . . . . ?
C5 C6 O2 C7 179.2(3) . . . . ?
C1 C6 O2 C7 -0.6(3) . . . . ?
