#------------------------------------------------------------------------------
#$Date: 2024-10-09 03:51:26 +0300 (Wed, 09 Oct 2024) $
#$Revision: 295374 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160174.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_7160174
loop_
_publ_author_name
'Duari, Surajit'
'Biswas, Subrata'
'Roy, Arnab'
'Maity, Srabani'
'Elsharif, Asma'
'Biswas, Srijit'
_publ_section_title
;
 MeOTf- catalyzed Friedel-Crafts alkylation of benzoxazolones,
 benzothiazolones, indolinones and benzimidazolones with activated
 secondary alcohols
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D4OB01372G
_journal_year                    2024
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36
_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             2024-04-04
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-06-28 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.779(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0708(12)
_cell_length_b                   12.580(2)
_cell_length_c                   21.139(4)
_cell_measurement_reflns_used    7321
_cell_measurement_temperature    229.24
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.52
_cell_volume                     1613.6(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      229.24
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.989
_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  0.0823
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16013
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.005
_diffrn_reflns_theta_min         3.239
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5025
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1538 before and 0.1135 after correction.
The Ratio of minimum to maximum transmission is 0.6746.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0626
_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)+(0.0927P)²+0.5215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2781
_reflns_number_total             3487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01372g2.cif
_cod_data_source_block           om36
_cod_original_cell_volume        1613.5(5)
_cod_database_code               7160174
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C9(H9)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
1.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.8393(2) 0.43173(11) 0.45961(8) 0.0589(5) Uani 1 1 d . . . . .
O2 O 0.7934(3) 0.27723(13) 0.51381(9) 0.0710(5) Uani 1 1 d . . . . .
N1 N 0.5154(2) 0.35196(12) 0.45129(7) 0.0384(4) Uani 1 1 d . . . . .
C1 C 0.7188(3) 0.34454(15) 0.47898(10) 0.0461(5) Uani 1 1 d . . . . .
C2 C 0.5037(3) 0.44272(14) 0.41338(8) 0.0349(4) Uani 1 1 d . . . . .
C3 C 0.7062(3) 0.49160(14) 0.41920(8) 0.0367(4) Uani 1 1 d . . . . .
C4 C 0.7583(3) 0.58342(14) 0.38727(9) 0.0405(4) Uani 1 1 d . . . . .
H4 H 0.897954 0.615167 0.392294 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5954(3) 0.62729(14) 0.34719(8) 0.0343(4) Uani 1 1 d . . . . .
C6 C 0.3918(3) 0.57875(19) 0.34147(11) 0.0565(6) Uani 1 1 d . . . . .
H6 H 0.283117 0.609424 0.314599 0.068 Uiso 1 1 calc R U . . .
C7 C 0.3410(3) 0.4856(2) 0.37419(12) 0.0620(7) Uani 1 1 d . . . . .
H7 H 0.201613 0.453489 0.369606 0.074 Uiso 1 1 calc R U . . .
C8 C 0.3421(4) 0.27421(18) 0.45963(12) 0.0592(6) Uani 1 1 d . . . . .
H8A H 0.302575 0.242131 0.419121 0.089 Uiso 1 1 calc R U . . .
H8B H 0.213961 0.308981 0.476515 0.089 Uiso 1 1 calc R U . . .
H8C H 0.393865 0.219535 0.488837 0.089 Uiso 1 1 calc R U . . .
C9 C 0.6353(3) 0.72954(13) 0.30984(8) 0.0341(4) Uani 1 1 d . . . . .
H9 H 0.499955 0.741682 0.283509 0.041 Uiso 1 1 calc R U . . .
C10 C 0.8242(3) 0.72064(13) 0.26362(7) 0.0350(4) Uani 1 1 d . . . . .
C11 C 0.8730(4) 0.62532(17) 0.23537(10) 0.0556(6) Uani 1 1 d . . . . .
H11 H 0.795030 0.563906 0.246515 0.067 Uiso 1 1 calc R U . . .
C12 C 1.0351(5) 0.61812(19) 0.19074(11) 0.0657(7) Uani 1 1 d . . . . .
H12 H 1.063540 0.552361 0.171520 0.079 Uiso 1 1 calc R U . . .
C13 C 1.1542(4) 0.70587(18) 0.17442(9) 0.0534(6) Uani 1 1 d . . . . .
H13 H 1.265335 0.700578 0.144587 0.064 Uiso 1 1 calc R U . . .
C14 C 1.1092(4) 0.80088(18) 0.20203(10) 0.0572(6) Uani 1 1 d . . . . .
H14 H 1.189618 0.861624 0.190993 0.069 Uiso 1 1 calc R U . . .
C15 C 0.9461(4) 0.80901(16) 0.24624(10) 0.0519(5) Uani 1 1 d . . . . .
H15 H 0.917453 0.875304 0.264770 0.062 Uiso 1 1 calc R U . . .
C16 C 0.6571(3) 0.82531(13) 0.35413(7) 0.0336(4) Uani 1 1 d . . . . .
C17 C 0.8450(3) 0.84283(14) 0.39183(8) 0.0412(4) Uani 1 1 d . . . . .
H17 H 0.965370 0.796203 0.389307 0.049 Uiso 1 1 calc R U . . .
C18 C 0.8568(4) 0.92824(16) 0.43311(9) 0.0500(5) Uani 1 1 d . . . . .
H18 H 0.984189 0.938436 0.458815 0.060 Uiso 1 1 calc R U . . .
C19 C 0.6830(4) 0.99859(16) 0.43681(9) 0.0503(5) Uani 1 1 d . . . . .
H19 H 0.692421 1.057041 0.464469 0.060 Uiso 1 1 calc R U . . .
C20 C 0.4971(4) 0.98246(19) 0.39989(12) 0.0593(6) Uani 1 1 d . . . . .
H20 H 0.378173 1.030005 0.402230 0.071 Uiso 1 1 calc R U . . .
C21 C 0.4830(3) 0.89600(17) 0.35884(10) 0.0523(5) Uani 1 1 d . . . . .
H21 H 0.353742 0.885380 0.333989 0.063 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
C3 O1 C1 108.08(14) . . ?
C1 N1 C2 109.54(15) . . ?
C1 N1 C8 123.79(17) . . ?
C2 N1 C8 126.66(16) . . ?
O2 C1 O1 123.09(19) . . ?
O2 C1 N1 129.44(19) . . ?
N1 C1 O1 107.47(16) . . ?
C3 C2 N1 106.54(15) . . ?
C3 C2 C7 120.00(17) . . ?
C7 C2 N1 133.45(16) . . ?
C2 C3 O1 108.38(15) . . ?
C2 C3 C4 123.23(16) . . ?
C4 C3 O1 128.38(16) . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.32(15) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 C9 121.60(15) . . ?
C6 C5 C4 119.60(17) . . ?
C6 C5 C9 118.80(16) . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.49(18) . . ?
C7 C6 H6 118.8 . . ?
C2 C7 C6 117.36(18) . . ?
C2 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9 106.1 . . ?
C5 C9 C10 113.60(14) . . ?
C10 C9 H9 106.1 . . ?
C16 C9 C5 110.97(13) . . ?
C16 C9 H9 106.1 . . ?
C16 C9 C10 113.29(14) . . ?
C11 C10 C9 121.04(16) . . ?
C11 C10 C15 117.26(17) . . ?
C15 C10 C9 121.63(15) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.27(19) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.01(18) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.7(2) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.08(19) . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C9 122.04(15) . . ?
C21 C16 C9 119.81(16) . . ?
C21 C16 C17 118.12(17) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.71(19) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.41(19) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.9(2) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
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 1.387(2) . ?
O1 C3 1.381(2) . ?
O2 C1 1.201(2) . ?
N1 C1 1.353(2) . ?
N1 C2 1.395(2) . ?
N1 C8 1.451(2) . ?
C2 C3 1.377(2) . ?
C2 C7 1.379(3) . ?
C3 C4 1.380(2) . ?
C4 H4 0.9400 . ?
C4 C5 1.396(2) . ?
C5 C6 1.380(3) . ?
C5 C9 1.532(2) . ?
C6 H6 0.9400 . ?
C6 C7 1.400(3) . ?
C7 H7 0.9400 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9 0.9900 . ?
C9 C10 1.533(2) . ?
C9 C16 1.529(2) . ?
C10 C11 1.376(3) . ?
C10 C15 1.391(3) . ?
C11 H11 0.9400 . ?
C11 C12 1.387(3) . ?
C12 H12 0.9400 . ?
C12 C13 1.370(3) . ?
C13 H13 0.9400 . ?
C13 C14 1.362(3) . ?
C14 H14 0.9400 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.388(3) . ?
C16 C21 1.388(3) . ?
C17 H17 0.9400 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9400 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9400 . ?
C19 C20 1.367(3) . ?
C20 H20 0.9400 . ?
C20 C21 1.392(3) . ?
C21 H21 0.9400 . ?
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
O1 C3 C4 C5 177.86(18) . . . . ?
N1 C2 C3 O1 0.25(19) . . . . ?
N1 C2 C3 C4 178.66(16) . . . . ?
N1 C2 C7 C6 -178.25(19) . . . . ?
C1 O1 C3 C2 0.2(2) . . . . ?
C1 O1 C3 C4 -178.11(18) . . . . ?
C1 N1 C2 C3 -0.62(19) . . . . ?
C1 N1 C2 C7 177.9(2) . . . . ?
C2 N1 C1 O1 0.7(2) . . . . ?
C2 N1 C1 O2 -178.7(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 O1 C1 O2 178.9(2) . . . . ?
C3 O1 C1 N1 -0.6(2) . . . . ?
C3 C2 C7 C6 0.1(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C9 179.57(15) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C4 C5 C9 C10 60.7(2) . . . . ?
C4 C5 C9 C16 -68.3(2) . . . . ?
C5 C6 C7 C2 0.2(4) . . . . ?
C5 C9 C10 C11 30.8(2) . . . . ?
C5 C9 C10 C15 -152.29(18) . . . . ?
C5 C9 C16 C17 74.46(19) . . . . ?
C5 C9 C16 C21 -103.56(18) . . . . ?
C6 C5 C9 C10 -120.23(19) . . . . ?
C6 C5 C9 C16 110.75(19) . . . . ?
C7 C2 C3 O1 -178.50(19) . . . . ?
C7 C2 C3 C4 -0.1(3) . . . . ?
C8 N1 C1 O1 179.28(18) . . . . ?
C8 N1 C1 O2 -0.1(4) . . . . ?
C8 N1 C2 C3 -179.10(18) . . . . ?
C8 N1 C2 C7 -0.6(3) . . . . ?
C9 C5 C6 C7 -179.6(2) . . . . ?
C9 C10 C11 C12 176.2(2) . . . . ?
C9 C10 C15 C14 -176.76(19) . . . . ?
C9 C16 C17 C18 -177.73(16) . . . . ?
C9 C16 C21 C20 178.56(18) . . . . ?
C10 C9 C16 C17 -54.7(2) . . . . ?
C10 C9 C16 C21 127.26(17) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C10 C15 C14 0.3(3) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
C16 C9 C10 C11 158.62(17) . . . . ?
C16 C9 C10 C15 -24.5(2) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C17 C16 C21 C20 0.5(3) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C16 -0.6(3) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
