#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:25:33 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278985 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245565.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_7245565
loop_
_publ_author_name
'Lu, Yuling'
'Chen, Chunmei'
'Zhu, Hucheng'
'Luo, Zengwei'
'Zhang, Yonghui'
_publ_section_title
;
 Highly efficient and fast synthesis of di-iodinated succinimide
 derivatives from 1,6-enyne and I2 under air at room temperature
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              8021
_journal_page_last               8028
_journal_paper_doi               10.1039/D2GC02058K
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C20 H17 I2 N O2'
_chemical_formula_weight         557.15
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-05-25 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.8590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.61260(10)
_cell_length_b                   23.4046(2)
_cell_length_c                   11.28240(10)
_cell_measurement_reflns_used    36800
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.691
_cell_measurement_theta_min      3.782
_cell_volume                     1951.66(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.796
_diffrn_reflns_theta_min         4.456
_exptl_absorpt_coefficient_mu    25.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         2.994
_refine_diff_density_min         -1.731
_refine_diff_density_rms         0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0432
_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)+(0.0837P)²+7.5408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3904
_reflns_number_total             3924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc02058k2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7245565.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245565
_shelx_shelxl_version_number     2014/7
_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   0.061
_shelx_estimated_absorpt_t_max   0.115
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
C1 C 0.8046(7) 0.5364(2) 0.6088(5) 0.0241(10) Uani 1 1 d . . . . .
H1 H 0.7290 0.5329 0.5311 0.029 Uiso 1 1 calc R U . . .
C2 C 0.9446(7) 0.4979(2) 0.6476(5) 0.0265(11) Uani 1 1 d . . . . .
H2 H 0.9638 0.4688 0.5958 0.032 Uiso 1 1 calc R U . . .
C3 C 1.0566(8) 0.5029(2) 0.7641(5) 0.0285(11) Uani 1 1 d . . . . .
H3 H 1.1503 0.4769 0.7904 0.034 Uiso 1 1 calc R U . . .
C4 C 1.0296(8) 0.5461(2) 0.8413(5) 0.0291(11) Uani 1 1 d . . . . .
H4 H 1.1051 0.5493 0.9192 0.035 Uiso 1 1 calc R U . . .
C5 C 0.8878(7) 0.5852(2) 0.8018(5) 0.0248(11) Uani 1 1 d . . . . .
H5 H 0.8691 0.6143 0.8537 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7761(8) 0.5807(2) 0.6863(5) 0.0249(11) Uani 1 1 d . . . . .
C7 C 0.6235(7) 0.6210(2) 0.6442(5) 0.0217(10) Uani 1 1 d . . . . .
C8 C 0.6350(7) 0.6729(2) 0.5984(4) 0.0217(10) Uani 1 1 d . . . . .
C9 C 0.4780(7) 0.7115(2) 0.5498(5) 0.0255(10) Uani 1 1 d . . . . .
C10 C 0.7298(7) 0.7573(2) 0.5119(5) 0.0231(10) Uani 1 1 d . . . . .
C11 C 0.8053(7) 0.7021(2) 0.5776(4) 0.0204(9) Uani 1 1 d . . . . .
C12 C 0.9444(7) 0.7208(3) 0.6976(4) 0.0325(14) Uani 1 1 d . . . . .
H12A H 0.9916 0.6876 0.7443 0.049 Uiso 1 1 calc R U . . .
H12B H 0.8850 0.7448 0.7450 0.049 Uiso 1 1 calc R U . . .
H12C H 1.0418 0.7416 0.6770 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9029(7) 0.6692(2) 0.4961(5) 0.0248(10) Uani 1 1 d . . . . .
H13A H 0.9585 0.6355 0.5394 0.030 Uiso 1 1 calc R U . . .
H13B H 0.9987 0.6930 0.4796 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4260(8) 0.8028(2) 0.4289(5) 0.0259(11) Uani 1 1 d . . . . .
H14A H 0.3126 0.7853 0.3870 0.031 Uiso 1 1 calc R U . . .
H14B H 0.4823 0.8184 0.3675 0.031 Uiso 1 1 calc R U . . .
C15 C 0.3875(7) 0.8506(2) 0.5082(5) 0.0239(11) Uani 1 1 d . . . . .
C16 C 0.2465(8) 0.8458(2) 0.5677(6) 0.0302(12) Uani 1 1 d . . . . .
H16 H 0.1738 0.8133 0.5566 0.036 Uiso 1 1 calc R U . . .
C17 C 0.2149(9) 0.8896(3) 0.6434(6) 0.0375(14) Uani 1 1 d . . . . .
H17 H 0.1218 0.8862 0.6833 0.045 Uiso 1 1 calc R U . . .
C18 C 0.3212(8) 0.9381(3) 0.6595(5) 0.0310(12) Uani 1 1 d . . . . .
H18 H 0.2999 0.9672 0.7104 0.037 Uiso 1 1 calc R U . . .
C19 C 0.4583(8) 0.9434(2) 0.6004(5) 0.0280(11) Uani 1 1 d . . . . .
H19 H 0.5281 0.9765 0.6105 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4940(7) 0.8998(2) 0.5256(5) 0.0240(10) Uani 1 1 d . . . . .
H20 H 0.5888 0.9034 0.4873 0.029 Uiso 1 1 calc R U . . .
I1 I 0.37808(4) 0.58323(2) 0.66191(3) 0.02312(14) Uani 1 1 d . . . . .
I2 I 0.72740(5) 0.64325(2) 0.32508(3) 0.02972(14) Uani 1 1 d . . . . .
N1 N 0.5450(6) 0.75861(18) 0.4986(4) 0.0248(9) Uani 1 1 d . . . . .
O1 O 0.8149(5) 0.79347(16) 0.4739(4) 0.0286(8) Uani 1 1 d . . . . .
O2 O 0.3210(5) 0.70542(17) 0.5503(4) 0.0354(9) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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 120.3(5) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 119.7(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.7(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.3(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 C7 120.8(5) . . ?
C1 C6 C7 119.7(5) . . ?
C8 C7 C6 125.8(5) . . ?
C8 C7 I1 124.0(4) . . ?
C6 C7 I1 110.1(3) . . ?
C7 C8 C9 125.0(5) . . ?
C7 C8 C11 127.1(5) . . ?
C9 C8 C11 107.8(4) . . ?
O2 C9 N1 123.8(5) . . ?
O2 C9 C8 129.4(5) . . ?
N1 C9 C8 106.8(4) . . ?
O1 C10 N1 124.6(5) . . ?
O1 C10 C11 126.4(5) . . ?
N1 C10 C11 109.0(4) . . ?
C13 C11 C10 108.4(4) . . ?
C13 C11 C8 114.8(4) . . ?
C10 C11 C8 102.6(4) . . ?
C13 C11 C12 109.7(4) . . ?
C10 C11 C12 106.2(4) . . ?
C8 C11 C12 114.4(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 I2 113.3(3) . . ?
C11 C13 H13A 108.9 . . ?
I2 C13 H13A 108.9 . . ?
C11 C13 H13B 108.9 . . ?
I2 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N1 C14 C15 112.8(4) . . ?
N1 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N1 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C20 C15 C16 119.0(5) . . ?
C20 C15 C14 120.5(5) . . ?
C16 C15 C14 120.4(5) . . ?
C17 C16 C15 120.0(5) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.3(6) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.1(6) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.0(5) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C10 N1 C9 113.7(4) . . ?
C10 N1 C14 123.7(4) . . ?
C9 N1 C14 122.4(4) . . ?
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 1.384(7) . ?
C1 C6 1.407(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.390(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(7) . ?
C7 C8 1.330(7) . ?
C7 I1 2.119(5) . ?
C8 C9 1.493(7) . ?
C8 C11 1.533(7) . ?
C9 O2 1.205(7) . ?
C9 N1 1.397(7) . ?
C10 O1 1.205(7) . ?
C10 N1 1.379(7) . ?
C10 C11 1.532(7) . ?
C11 C13 1.522(7) . ?
C11 C12 1.568(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 I2 2.154(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.472(7) . ?
C14 C15 1.505(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.395(8) . ?
C15 C16 1.400(8) . ?
C16 C17 1.391(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(8) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
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 0.5(8) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
C4 C5 C6 C1 0.4(8) . . . . ?
C4 C5 C6 C7 178.8(5) . . . . ?
C2 C1 C6 C5 -0.6(8) . . . . ?
C2 C1 C6 C7 -179.0(5) . . . . ?
C5 C6 C7 C8 82.9(7) . . . . ?
C1 C6 C7 C8 -98.7(7) . . . . ?
C5 C6 C7 I1 -98.9(5) . . . . ?
C1 C6 C7 I1 79.5(5) . . . . ?
C6 C7 C8 C9 176.2(5) . . . . ?
I1 C7 C8 C9 -1.7(7) . . . . ?
C6 C7 C8 C11 0.8(9) . . . . ?
I1 C7 C8 C11 -177.2(4) . . . . ?
C7 C8 C9 O2 5.6(9) . . . . ?
C11 C8 C9 O2 -178.2(6) . . . . ?
C7 C8 C9 N1 -173.6(5) . . . . ?
C11 C8 C9 N1 2.6(6) . . . . ?
O1 C10 C11 C13 -55.9(7) . . . . ?
N1 C10 C11 C13 122.0(4) . . . . ?
O1 C10 C11 C8 -177.7(5) . . . . ?
N1 C10 C11 C8 0.2(5) . . . . ?
O1 C10 C11 C12 61.9(6) . . . . ?
N1 C10 C11 C12 -120.2(4) . . . . ?
C7 C8 C11 C13 57.1(7) . . . . ?
C9 C8 C11 C13 -119.0(5) . . . . ?
C7 C8 C11 C10 174.4(5) . . . . ?
C9 C8 C11 C10 -1.7(5) . . . . ?
C7 C8 C11 C12 -71.0(7) . . . . ?
C9 C8 C11 C12 112.9(5) . . . . ?
C10 C11 C13 I2 -62.6(5) . . . . ?
C8 C11 C13 I2 51.3(5) . . . . ?
C12 C11 C13 I2 -178.2(3) . . . . ?
N1 C14 C15 C20 93.3(6) . . . . ?
N1 C14 C15 C16 -85.4(6) . . . . ?
C20 C15 C16 C17 -0.4(8) . . . . ?
C14 C15 C16 C17 178.3(5) . . . . ?
C15 C16 C17 C18 0.6(9) . . . . ?
C16 C17 C18 C19 0.2(9) . . . . ?
C17 C18 C19 C20 -1.2(9) . . . . ?
C18 C19 C20 C15 1.3(8) . . . . ?
C16 C15 C20 C19 -0.5(8) . . . . ?
C14 C15 C20 C19 -179.2(5) . . . . ?
O1 C10 N1 C9 179.5(5) . . . . ?
C11 C10 N1 C9 1.6(6) . . . . ?
O1 C10 N1 C14 4.1(8) . . . . ?
C11 C10 N1 C14 -173.8(4) . . . . ?
O2 C9 N1 C10 178.1(5) . . . . ?
C8 C9 N1 C10 -2.6(6) . . . . ?
O2 C9 N1 C14 -6.5(9) . . . . ?
C8 C9 N1 C14 172.8(4) . . . . ?
C15 C14 N1 C10 -95.7(6) . . . . ?
C15 C14 N1 C9 89.4(6) . . . . ?
