#------------------------------------------------------------------------------
#$Date: 2021-10-06 19:16:10 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269784 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158169.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_7158169
loop_
_publ_author_name
'Lai, Huifang'
'Xu, Jiexin'
'Lin, Jin'
'Zha, Daijun'
_publ_section_title
;
 Copper-promoted direct amidation of isoindolinone scaffolds by sodium
 persulfate.
;
_journal_issue                   35
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7621
_journal_page_last               7626
_journal_paper_doi               10.1039/d1ob01054a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2021-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-01 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.446(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.806(3)
_cell_length_b                   11.637(3)
_cell_length_c                   9.954(3)
_cell_measurement_reflns_used    2624
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      27.4855
_cell_measurement_theta_min      2.1547
_cell_volume                     1094.8(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8554
_diffrn_reflns_theta_full        27.4844
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.3119
_exptl_crystal_description       Prism
_exptl_crystal_F_000             456.2227
_refine_diff_density_max         0.1982
_refine_diff_density_min         -0.2286
_refine_diff_density_rms         0.0412
_refine_ls_d_res_high            0.7700
_refine_ls_d_res_low             7.8608
_refine_ls_goodness_of_fit_ref   1.0483
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0483
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0794P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1413
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -7
_reflns_number_gt                1717
_reflns_number_total             2504
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ob01054a2.cif
_cod_data_source_block           2-lactam-isoindolinone
_cod_depositor_comments
'Adding full bibliography for 7158168--7158169.cif.'
_cod_original_cell_volume        1094.8(6)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7158169
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C15(H15a,H15b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C8(H8), C11(H11), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-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_refinement_flags_posn
O1 O 0.01512(12) 0.55720(9) 0.83470(10) 0.0631(3) Uani 1.000000 .
N2 N 0.14306(12) 0.80198(10) 1.20182(11) 0.0507(3) Uani 1.000000 .
N3 N 0.10373(14) 0.63236(10) 1.05488(12) 0.0544(3) Uani 1.000000 .
H3 H 0.05671(14) 0.58772(10) 1.09822(12) 0.0652(4) Uiso 1.000000 R
C4 C 0.08968(16) 0.62574(11) 0.91634(14) 0.0494(4) Uani 1.000000 .
C5 C 0.18279(15) 0.71555(12) 0.88389(14) 0.0484(4) Uani 1.000000 .
C6 C 0.20353(15) 0.71982(12) 1.12659(14) 0.0502(4) Uani 1.000000 .
H6 H 0.28607(15) 0.68153(12) 1.19237(14) 0.0602(4) Uiso 1.000000 R
O7 O 0.24425(16) 0.72920(13) 1.41750(12) 0.0949(5) Uani 1.000000 .
C8 C 0.20918(16) 0.74443(13) 0.75733(15) 0.0559(4) Uani 1.000000 .
H8 H 0.16331(16) 0.70532(13) 0.67373(15) 0.0670(5) Uiso 1.000000 R
C9 C 0.16948(18) 0.79983(15) 1.34190(17) 0.0636(5) Uani 1.000000 .
C10 C 0.25050(15) 0.77109(12) 1.00599(15) 0.0514(4) Uani 1.000000 .
C11 C 0.30430(17) 0.83185(15) 0.75774(17) 0.0651(5) Uani 1.000000 .
H11 H 0.32469(17) 0.85367(15) 0.67318(17) 0.0781(5) Uiso 1.000000 R
C12 C 0.0463(2) 0.89135(15) 1.13440(19) 0.0773(6) Uani 1.000000 .
H12a H 0.0918(2) 0.94346(15) 1.08067(19) 0.0927(7) Uiso 1.000000 R
H12b H -0.0397(2) 0.85792(15) 1.07066(19) 0.0927(7) Uiso 1.000000 R
C13 C 0.37031(19) 0.88808(16) 0.88047(19) 0.0740(5) Uani 1.000000 .
H13 H 0.43465(19) 0.94858(16) 0.87803(19) 0.0888(6) Uiso 1.000000 R
C14 C 0.34536(18) 0.85878(15) 1.00643(18) 0.0689(5) Uani 1.000000 .
H14 H 0.39176(18) 0.89754(15) 1.09012(18) 0.0827(6) Uiso 1.000000 R
C15 C 0.0103(2) 0.95474(18) 1.2533(2) 0.0897(6) Uani 1.000000 .
H15a H 0.0377(2) 1.03661(18) 1.2532(2) 0.1076(8) Uiso 1.000000 R
H15b H -0.0926(2) 0.95046(18) 1.2442(2) 0.1076(8) Uiso 1.000000 R
C16 C 0.0912(2) 0.89763(18) 1.3848(2) 0.0910(6) Uani 1.000000 .
H16a H 0.0259(2) 0.86896(18) 1.4379(2) 0.1093(8) Uiso 1.000000 R
H16b H 0.1582(2) 0.95238(18) 1.4442(2) 0.1093(8) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C9 N2 C6 122.29(12) . . ?
C12 N2 C6 123.20(12) . . ?
C12 N2 C9 114.49(13) . . ?
C6 N3 C4 114.31(11) . . ?
N3 C4 O1 126.31(13) . . ?
C5 C4 O1 127.33(13) . . ?
C5 C4 N3 106.35(12) . . ?
C8 C5 C4 129.95(13) . . ?
C10 C5 C4 108.58(12) . . ?
C10 C5 C8 121.44(13) . . ?
N3 C6 N2 113.76(11) . . ?
C10 C6 N2 113.90(12) . . ?
C10 C6 N3 101.10(11) . . ?
C11 C8 C5 117.61(14) . . ?
O7 C9 N2 124.69(16) . . ?
C16 C9 N2 108.00(15) . . ?
C16 C9 O7 127.31(16) . . ?
C6 C10 C5 109.65(12) . . ?
C14 C10 C5 120.98(13) . . ?
C14 C10 C6 129.38(14) . . ?
C13 C11 C8 120.52(14) . . ?
C15 C12 N2 104.38(15) . . ?
C14 C13 C11 121.96(15) . . ?
C13 C14 C10 117.48(15) . . ?
C16 C15 C12 106.77(16) . . ?
C15 C16 C9 106.30(16) . . ?
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 C4 1.2306(16) . ?
N2 C6 1.4363(18) . ?
N2 C9 1.3488(19) . ?
N2 C12 1.4468(19) . ?
N3 C4 1.3510(18) . ?
N3 C6 1.4598(18) . ?
C4 C5 1.4790(19) . ?
C5 C8 1.3930(19) . ?
C5 C10 1.380(2) . ?
C6 C10 1.518(2) . ?
O7 C9 1.219(2) . ?
C8 C11 1.379(2) . ?
C9 C16 1.497(3) . ?
C10 C14 1.380(2) . ?
C11 C13 1.385(2) . ?
C12 C15 1.514(3) . ?
C13 C14 1.383(2) . ?
C15 C16 1.494(3) . ?
