#------------------------------------------------------------------------------
#$Date: 2022-04-08 03:35:24 +0300 (Fri, 08 Apr 2022) $
#$Revision: 274422 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158629.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_7158629
loop_
_publ_author_name
'Wong, Man Kin'
'Cui, Jian-Fang'
'Yu, Qiong'
'O, Wa-Yi'
'Huang, Liwu'
'Yang, Bin'
_publ_section_title
;
 Synthesis of 1H-Isoindoliums by Electrophile-Mediated Cascade
 Cyclization/Iodination of Propargylamine-based 1,6-Diynes
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00316C
_journal_year                    2022
_chemical_formula_sum            'C21 H18 Cl F6 I N O P'
_chemical_formula_weight         607.68
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-06-28 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.944(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0081(9)
_cell_length_b                   12.9824(11)
_cell_length_c                   17.1316(16)
_cell_measurement_reflns_used    9631
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.38
_cell_volume                     2220.6(3)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8_VENTURE PHOTOS 100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            64193
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    1.699
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SAINT
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.0006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5096
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0622
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0812P)²+10.6500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.1851
_reflns_number_gt                3940
_reflns_number_total             5096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob00316c2.cif
_cod_data_source_block           cjf21
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7158629
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.30285(3) 0.56073(3) 0.06660(2) 0.07115(11) Uani 1 1 d . . .
Cl1 Cl 0.19622(14) 0.12441(11) 0.17844(11) 0.0865(5) Uani 1 1 d . . .
O1 O 0.9809(3) 0.2825(2) 0.30078(19) 0.0585(8) Uani 1 1 d . . .
N1 N 0.9576(3) 0.4521(2) 0.19319(18) 0.0390(7) Uani 1 1 d . . .
C1 C 0.8185(4) 0.4997(3) 0.1841(2) 0.0465(10) Uani 1 1 d . . .
C2 C 0.8247(4) 0.5855(3) 0.1303(2) 0.0447(9) Uani 1 1 d . . .
C3 C 0.7248(5) 0.6514(4) 0.1060(3) 0.0585(12) Uani 1 1 d . . .
H3A H 0.654(5) 0.641(4) 0.123(3) 0.053(13) Uiso 1 1 d . . .
C4 C 0.7534(6) 0.7304(4) 0.0561(3) 0.0669(14) Uani 1 1 d . . .
H4A H 0.6857 0.7757 0.0387 0.080 Uiso 1 1 calc R . .
C5 C 0.8810(6) 0.7434(4) 0.0317(3) 0.0687(14) Uani 1 1 d . . .
H5A H 0.8988 0.7984 -0.0007 0.082 Uiso 1 1 calc R . .
C6 C 0.9808(5) 0.6767(4) 0.0546(3) 0.0580(12) Uani 1 1 d . . .
H6A H 1.0659 0.6847 0.0368 0.070 Uiso 1 1 calc R . .
C7 C 0.9542(4) 0.5958(3) 0.1051(2) 0.0447(9) Uani 1 1 d . . .
C8 C 1.0409(4) 0.5160(3) 0.1394(2) 0.0428(9) Uani 1 1 d . . .
C9 C 1.1664(4) 0.4889(3) 0.1335(3) 0.0506(10) Uani 1 1 d . . .
H9A H 1.1966 0.4317 0.1623 0.061 Uiso 1 1 calc R . .
C10 C 1.0171(4) 0.4613(3) 0.2770(2) 0.0503(10) Uani 1 1 d . . .
H10A H 1.1135 0.4532 0.2777 0.055(13) Uiso 1 1 calc R . .
H10B H 0.9988 0.5296 0.2966 0.066 Uiso 1 1 calc R . .
C11 C 0.9620(4) 0.3828(4) 0.3299(2) 0.0545(11) Uani 1 1 d . . .
H11A H 1.0066 0.3889 0.3818 0.090(18) Uiso 1 1 calc R . .
H11B H 0.8672 0.3952 0.3340 0.108 Uiso 1 1 calc R . .
C12 C 0.9040(4) 0.2695(3) 0.2286(3) 0.0541(11) Uani 1 1 d . . .
H12A H 0.8107 0.2847 0.2358 0.065 Uiso 1 1 calc R . .
H12B H 0.9099 0.1985 0.2115 0.065 Uiso 1 1 calc R . .
C13 C 0.9542(4) 0.3400(3) 0.1670(2) 0.0478(10) Uani 1 1 d . . .
H13B H 1.055(5) 0.324(4) 0.160(3) 0.076(16) Uiso 1 1 d . . .
H13A H 0.904(5) 0.336(4) 0.113(3) 0.064(14) Uiso 1 1 d . . .
C14 C 0.7174(4) 0.4664(3) 0.2203(3) 0.0532(11) Uani 1 1 d . . .
C15 C 0.6124(5) 0.4440(4) 0.2590(3) 0.0585(12) Uani 1 1 d . . .
H15A H 0.6019 0.4806 0.3048 0.070 Uiso 1 1 calc R . .
C16 C 0.5104(4) 0.3666(4) 0.2365(3) 0.0510(10) Uani 1 1 d . . .
C17 C 0.4123(4) 0.3447(3) 0.2867(3) 0.0520(11) Uani 1 1 d . . .
H17A H 0.4116 0.3810 0.3335 0.062 Uiso 1 1 calc R . .
C18 C 0.3153(4) 0.2712(4) 0.2701(3) 0.0544(11) Uani 1 1 d . . .
H18A H 0.244(4) 0.261(3) 0.306(2) 0.051(12) Uiso 1 1 d . . .
C19 C 0.3163(4) 0.2172(3) 0.2016(3) 0.0562(12) Uani 1 1 d . . .
C20 C 0.4143(5) 0.2380(4) 0.1490(3) 0.0662(14) Uani 1 1 d . . .
H20A H 0.415(5) 0.203(4) 0.113(3) 0.056(13) Uiso 1 1 d . . .
C21 C 0.5096(5) 0.3104(4) 0.1676(3) 0.0614(13) Uani 1 1 d . . .
H21A H 0.5760 0.3224 0.1333 0.074 Uiso 1 1 calc R . .
P1 P 0.73726(10) 0.10276(8) 0.03537(6) 0.0452(2) Uani 1 1 d D . .
F1 F 0.5884(5) 0.1252(7) 0.0150(3) 0.197(3) Uani 1 1 d D . .
F2 F 0.7047(4) 0.0977(3) 0.1255(2) 0.1044(12) Uani 1 1 d D . .
F3 F 0.8893(5) 0.1051(9) 0.0598(4) 0.231(4) Uani 1 1 d D . .
F4 F 0.7701(5) 0.1156(4) -0.0530(2) 0.1224(16) Uani 1 1 d D . .
F5 F 0.7533(8) 0.2223(4) 0.0485(3) 0.189(3) Uani 1 1 d D . .
F6 F 0.7370(10) -0.0138(4) 0.0301(4) 0.271(4) Uani 1 1 d 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C11 O1 C12 109.8(3) . . ?
C1 N1 C10 111.2(3) . . ?
C1 N1 C13 110.9(3) . . ?
C10 N1 C13 110.7(3) . . ?
C1 N1 C8 104.5(3) . . ?
C10 N1 C8 109.4(3) . . ?
C13 N1 C8 110.1(3) . . ?
C14 C1 C2 129.0(4) . . ?
C14 C1 N1 123.6(4) . . ?
C2 C1 N1 107.4(3) . . ?
C3 C2 C7 121.5(4) . . ?
C3 C2 C1 128.0(4) . . ?
C7 C2 C1 110.5(3) . . ?
C2 C3 C4 118.6(5) . . ?
C2 C3 H3A 115(3) . . ?
C4 C3 H3A 126(3) . . ?
C3 C4 C5 120.9(5) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
C6 C7 C2 118.8(4) . . ?
C6 C7 C8 130.8(4) . . ?
C2 C7 C8 110.4(3) . . ?
C9 C8 C7 135.1(4) . . ?
C9 C8 N1 117.7(3) . . ?
C7 C8 N1 107.2(3) . . ?
C8 C9 I1 126.4(3) . . ?
C8 C9 H9A 116.8 . . ?
I1 C9 H9A 116.8 . . ?
C11 C10 N1 112.4(3) . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
N1 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
O1 C11 C10 110.6(4) . . ?
O1 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O1 C12 C13 110.5(3) . . ?
O1 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 N1 112.0(3) . . ?
C12 C13 H13B 109(3) . . ?
N1 C13 H13B 103(3) . . ?
C12 C13 H13A 116(3) . . ?
N1 C13 H13A 108(3) . . ?
H13B C13 H13A 107(4) . . ?
C1 C14 C15 173.2(5) . . ?
C14 C15 C16 125.9(5) . . ?
C14 C15 H15A 117.1 . . ?
C16 C15 H15A 117.1 . . ?
C17 C16 C21 117.4(4) . . ?
C17 C16 C15 119.4(4) . . ?
C21 C16 C15 123.2(4) . . ?
C18 C17 C16 122.4(4) . . ?
C18 C17 H17A 118.8 . . ?
C16 C17 H17A 118.8 . . ?
C19 C18 C17 119.1(4) . . ?
C19 C18 H18A 121(3) . . ?
C17 C18 H18A 120(3) . . ?
C18 C19 C20 119.9(4) . . ?
C18 C19 Cl1 120.5(4) . . ?
C20 C19 Cl1 119.6(4) . . ?
C21 C20 C19 119.5(5) . . ?
C21 C20 H20A 124(4) . . ?
C19 C20 H20A 116(4) . . ?
C20 C21 C16 121.7(4) . . ?
C20 C21 H21A 119.1 . . ?
C16 C21 H21A 119.1 . . ?
F6 P1 F1 100.3(5) . . ?
F6 P1 F3 91.9(6) . . ?
F1 P1 F3 167.7(6) . . ?
F6 P1 F5 172.7(5) . . ?
F1 P1 F5 86.2(4) . . ?
F3 P1 F5 81.6(5) . . ?
F6 P1 F4 92.7(3) . . ?
F1 P1 F4 91.4(3) . . ?
F3 P1 F4 89.5(3) . . ?
F5 P1 F4 90.4(3) . . ?
F6 P1 F2 91.0(3) . . ?
F1 P1 F2 88.2(2) . . ?
F3 P1 F2 90.1(3) . . ?
F5 P1 F2 85.8(3) . . ?
F4 P1 F2 176.3(3) . . ?
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
I1 C9 2.065(4) . ?
Cl1 C19 1.728(5) . ?
O1 C11 1.412(6) . ?
O1 C12 1.421(5) . ?
N1 C1 1.521(5) . ?
N1 C10 1.521(5) . ?
N1 C13 1.523(5) . ?
N1 C8 1.529(5) . ?
C1 C14 1.297(6) . ?
C1 C2 1.450(6) . ?
C2 C3 1.359(6) . ?
C2 C7 1.400(6) . ?
C3 C4 1.378(7) . ?
C3 H3A 0.80(5) . ?
C4 C5 1.381(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.360(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.398(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.449(5) . ?
C8 C9 1.315(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.494(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.509(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13B 1.05(5) . ?
C13 H13A 1.03(5) . ?
C14 C15 1.313(7) . ?
C15 C16 1.466(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.379(6) . ?
C16 C21 1.386(7) . ?
C17 C18 1.377(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.368(7) . ?
C18 H18A 0.98(4) . ?
C19 C20 1.403(7) . ?
C20 C21 1.362(7) . ?
C20 H20A 0.77(5) . ?
C21 H21A 0.9300 . ?
P1 F6 1.515(5) . ?
P1 F1 1.535(5) . ?
P1 F3 1.550(5) . ?
P1 F5 1.575(5) . ?
P1 F4 1.580(3) . ?
P1 F2 1.602(3) . ?
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
C10 N1 C1 C14 -62.6(5) . . . . ?
C13 N1 C1 C14 60.9(5) . . . . ?
C8 N1 C1 C14 179.5(4) . . . . ?
C10 N1 C1 C2 116.8(3) . . . . ?
C13 N1 C1 C2 -119.7(3) . . . . ?
C8 N1 C1 C2 -1.1(4) . . . . ?
C14 C1 C2 C3 0.7(8) . . . . ?
N1 C1 C2 C3 -178.7(4) . . . . ?
C14 C1 C2 C7 179.3(4) . . . . ?
N1 C1 C2 C7 -0.1(4) . . . . ?
C7 C2 C3 C4 -0.6(7) . . . . ?
C1 C2 C3 C4 177.9(4) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C3 C4 C5 C6 1.9(8) . . . . ?
C4 C5 C6 C7 -1.8(7) . . . . ?
C5 C6 C7 C2 0.5(6) . . . . ?
C5 C6 C7 C8 -178.7(4) . . . . ?
C3 C2 C7 C6 0.6(6) . . . . ?
C1 C2 C7 C6 -178.1(4) . . . . ?
C3 C2 C7 C8 -180.0(4) . . . . ?
C1 C2 C7 C8 1.3(5) . . . . ?
C6 C7 C8 C9 -3.5(8) . . . . ?
C2 C7 C8 C9 177.2(5) . . . . ?
C6 C7 C8 N1 177.3(4) . . . . ?
C2 C7 C8 N1 -2.0(4) . . . . ?
C1 N1 C8 C9 -177.5(4) . . . . ?
C10 N1 C8 C9 63.4(5) . . . . ?
C13 N1 C8 C9 -58.4(4) . . . . ?
C1 N1 C8 C7 1.8(4) . . . . ?
C10 N1 C8 C7 -117.3(3) . . . . ?
C13 N1 C8 C7 120.9(3) . . . . ?
C7 C8 C9 I1 1.4(7) . . . . ?
N1 C8 C9 I1 -179.5(3) . . . . ?
C1 N1 C10 C11 78.5(4) . . . . ?
C13 N1 C10 C11 -45.1(5) . . . . ?
C8 N1 C10 C11 -166.6(3) . . . . ?
C12 O1 C11 C10 -65.5(4) . . . . ?
N1 C10 C11 O1 55.8(5) . . . . ?
C11 O1 C12 C13 65.1(4) . . . . ?
O1 C12 C13 N1 -54.8(4) . . . . ?
C1 N1 C13 C12 -79.2(4) . . . . ?
C10 N1 C13 C12 44.6(4) . . . . ?
C8 N1 C13 C12 165.6(3) . . . . ?
C2 C1 C14 C15 -46(4) . . . . ?
N1 C1 C14 C15 133(4) . . . . ?
C1 C14 C15 C16 140(4) . . . . ?
C14 C15 C16 C17 173.9(5) . . . . ?
C14 C15 C16 C21 -3.5(8) . . . . ?
C21 C16 C17 C18 -0.8(7) . . . . ?
C15 C16 C17 C18 -178.4(4) . . . . ?
C16 C17 C18 C19 0.4(7) . . . . ?
C17 C18 C19 C20 -0.7(7) . . . . ?
C17 C18 C19 Cl1 -179.9(3) . . . . ?
C18 C19 C20 C21 1.5(7) . . . . ?
Cl1 C19 C20 C21 -179.4(4) . . . . ?
C19 C20 C21 C16 -1.9(8) . . . . ?
C17 C16 C21 C20 1.5(7) . . . . ?
C15 C16 C21 C20 179.1(5) . . . . ?
