#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/38/1553846.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_1553846
loop_
_publ_author_name
'Wu, Shangze'
'Huang, Xin'
'Fu, Chunling'
'Ma, Shengming'
_publ_section_title
;
 Asymmetric SN2′-type C--H functionalization of arenes with
 propargylic alcohols
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2002
_journal_paper_doi               10.1039/C7QO00588A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C17 H22 I N O2'
_chemical_formula_sum            'C17 H22 I N O2'
_chemical_formula_weight         399.26
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2017-01-05 deposited with the CCDC.
2017-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.261(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7810(10)
_cell_length_b                   12.2621(7)
_cell_length_c                   12.7517(10)
_cell_measurement_reflns_used    1713
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5383
_cell_measurement_theta_min      3.2568
_cell_volume                     1728.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0228349000
_diffrn_orient_matrix_UB_12      0.0361227000
_diffrn_orient_matrix_UB_13      0.0313510000
_diffrn_orient_matrix_UB_21      0.0200980000
_diffrn_orient_matrix_UB_22      0.0451702000
_diffrn_orient_matrix_UB_23      -0.0236650000
_diffrn_orient_matrix_UB_31      -0.0565105000
_diffrn_orient_matrix_UB_32      0.0014125000
_diffrn_orient_matrix_UB_33      -0.0444033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7006
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0460
_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)+(0.0438P)²+1.2462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1149
_reflns_number_gt                2229
_reflns_number_total             3159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00588a2.cif
_cod_data_source_block           161102_wsz_9_97
_cod_database_code               1553846
_chemical_oxdiff_formula         'c10 h10 n2 o8 I1'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C17 \\sim C17A \\sim C16A: within 3.8A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3. Others
 Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C15(H15C,H15D), C16(H16A,H16B), C16A(H16C,H16D)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C17A(H17D,H17E,H17F)
;
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I 0.26192(4) 0.87167(3) 0.03871(3) 0.0754(2) Uani 1 d . . .
O1 O 0.1160(3) 0.5672(3) -0.1265(3) 0.0546(8) Uani 1 d . . .
O2 O -0.0351(3) 0.4195(3) -0.2126(3) 0.0648(9) Uani 1 d . . .
N1 N -0.0016(4) 0.4826(3) -0.2913(3) 0.0537(10) Uani 1 d . . .
C1 C 0.1177(5) 0.6512(5) -0.4002(5) 0.0675(15) Uani 1 d . . .
H1 H 0.0669 0.6078 -0.4569 0.081 Uiso 1 calc . . R
C2 C 0.1853(6) 0.7341(5) -0.4223(5) 0.0843(18) Uani 1 d . . .
H2 H 0.1792 0.7476 -0.4958 0.101 Uiso 1 calc . . R
C3 C 0.2615(6) 0.7973(5) -0.3381(6) 0.086(2) Uani 1 d . . .
H3 H 0.3069 0.8517 -0.3556 0.103 Uiso 1 calc . . R
C4 C 0.2718(6) 0.7815(5) -0.2291(5) 0.0786(18) Uani 1 d . . .
H4 H 0.3238 0.8243 -0.1726 0.094 Uiso 1 calc . . R
C5 C 0.2034(5) 0.7006(4) -0.2047(4) 0.0569(13) Uani 1 d . . .
C6 C 0.1290(4) 0.6359(4) -0.2901(4) 0.0531(12) Uani 1 d . . .
C7 C 0.0738(4) 0.5552(4) -0.2393(4) 0.0502(12) Uani 1 d . . .
C8 C 0.1968(4) 0.6618(4) -0.0948(4) 0.0529(12) Uani 1 d . . .
C9 C -0.1193(7) 0.3406(6) -0.2725(5) 0.101(2) Uani 1 d . . .
H9A H -0.1869 0.3761 -0.3267 0.151 Uiso 1 calc . . GR
H9B H -0.1467 0.2996 -0.2217 0.151 Uiso 1 calc . . GR
H9C H -0.0815 0.2923 -0.3098 0.151 Uiso 1 calc . . GR
C10 C 0.1372(4) 0.7461(4) -0.0420(4) 0.0502(12) Uani 1 d . . .
C11 C 0.0264(5) 0.7514(4) -0.0398(4) 0.0534(12) Uani 1 d . . .
C12 C -0.0727(5) 0.6694(5) -0.0914(6) 0.0844(19) Uani 1 d . . .
H12A H -0.0951 0.6713 -0.1713 0.127 Uiso 1 calc . . GR
H12B H -0.1418 0.6871 -0.0711 0.127 Uiso 1 calc . . GR
H12C H -0.0444 0.5978 -0.0646 0.127 Uiso 1 calc . . GR
C13 C -0.0188(6) 0.8419(5) 0.0155(5) 0.0774(17) Uani 1 d . . .
H13A H 0.0484 0.8850 0.0605 0.116 Uiso 1 calc . . GR
H13B H -0.0597 0.8111 0.0620 0.116 Uiso 1 calc . . GR
H13C H -0.0740 0.8871 -0.0407 0.116 Uiso 1 calc . . GR
C14 C 0.3157(5) 0.6166(5) -0.0169(6) 0.0799(19) Uani 1 d A . .
H14A H 0.3434 0.5608 -0.0564 0.096 Uiso 1 calc . . R
H14B H 0.3753 0.6747 0.0019 0.096 Uiso 1 calc . . R
C15 C 0.3103(7) 0.5682(6) 0.0901(6) 0.116(3) Uani 1 d . . .
H15A H 0.2313 0.5344 0.0713 0.139 Uiso 0.555(19) calc A 1 R
H15B H 0.3111 0.6292 0.1388 0.139 Uiso 0.555(19) calc A 1 R
H15C H 0.2574 0.5053 0.0777 0.139 Uiso 0.445(19) calc A 2 R
H15D H 0.2894 0.6213 0.1368 0.139 Uiso 0.445(19) calc A 2 R
C16 C 0.4042(19) 0.4833(17) 0.1634(16) 0.131(5) Uani 0.555(19) d A 1 .
H16A H 0.3761 0.4526 0.2201 0.157 Uiso 0.555(19) calc A 1 R
H16B H 0.4158 0.4245 0.1172 0.157 Uiso 0.555(19) calc A 1 R
C17 C 0.514(2) 0.5416(19) 0.2137(18) 0.140(6) Uani 0.555(19) d A 1 .
H17A H 0.5453 0.5642 0.1570 0.210 Uiso 0.555(19) calc A 1 GR
H17B H 0.5717 0.4954 0.2665 0.210 Uiso 0.555(19) calc A 1 GR
H17C H 0.4987 0.6047 0.2514 0.210 Uiso 0.555(19) calc A 1 GR
C16A C 0.454(2) 0.536(2) 0.137(2) 0.129(5) Uani 0.445(19) d A 2 .
H16C H 0.4723 0.4889 0.0834 0.155 Uiso 0.445(19) calc A 2 R
H16D H 0.5031 0.6011 0.1471 0.155 Uiso 0.445(19) calc A 2 R
C17A C 0.477(3) 0.484(2) 0.234(2) 0.141(7) Uani 0.445(19) d A 2 .
H17D H 0.4230 0.4226 0.2241 0.212 Uiso 0.445(19) calc A 2 GR
H17E H 0.4642 0.5329 0.2881 0.212 Uiso 0.445(19) calc A 2 GR
H17F H 0.5589 0.4587 0.2610 0.212 Uiso 0.445(19) calc A 2 GR
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'
I I -0.4742 1.8119 '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
C7 O1 C8 110.0(4)
C9 O2 N1 107.8(4)
C7 N1 O2 109.1(4)
C2 C1 H1 121.6
C6 C1 H1 121.6
C6 C1 C2 116.7(5)
C1 C2 H2 119.3
C3 C2 C1 121.5(6)
C3 C2 H2 119.3
C2 C3 H3 119.4
C4 C3 C2 121.2(6)
C4 C3 H3 119.4
C3 C4 H4 120.7
C3 C4 C5 118.6(5)
C5 C4 H4 120.7
C4 C5 C6 119.6(5)
C4 C5 C8 131.2(5)
C6 C5 C8 109.1(4)
C1 C6 C5 122.3(5)
C1 C6 C7 130.3(5)
C5 C6 C7 107.4(4)
O1 C7 C6 110.0(4)
N1 C7 O1 124.2(5)
N1 C7 C6 125.8(4)
O1 C8 C5 103.4(4)
O1 C8 C10 107.6(4)
O1 C8 C14 104.8(4)
C5 C8 C10 112.0(4)
C5 C8 C14 113.1(5)
C14 C8 C10 114.9(4)
O2 C9 H9A 109.5
O2 C9 H9B 109.5
O2 C9 H9C 109.5
H9A C9 H9B 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 I1 110.8(3)
C11 C10 I1 118.5(4)
C11 C10 C8 130.7(4)
C10 C11 C12 125.5(5)
C10 C11 C13 124.1(5)
C13 C11 C12 110.4(5)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12B 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13B 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C8 C14 H14A 108.6
C8 C14 H14B 108.6
H14A C14 H14B 107.6
C15 C14 C8 114.7(5)
C15 C14 H14A 108.6
C15 C14 H14B 108.6
C14 C15 H15A 106.4
C14 C15 H15B 106.4
C14 C15 H15C 113.0
C14 C15 H15D 113.0
C14 C15 C16 123.8(11)
C14 C15 C16A 93.5(12)
H15A C15 H15B 106.4
H15A C15 H15C 27.5
H15A C15 H15D 90.7
H15B C15 H15C 125.5
H15B C15 H15D 15.8
H15C C15 H15D 110.4
C16 C15 H15A 106.4
C16 C15 H15B 106.4
C16 C15 H15C 81.4
C16 C15 H15D 110.8
C16 C15 C16A 36.5(8)
C16A C15 H15A 140.3
C16A C15 H15B 100.1
C16A C15 H15C 113.0
C16A C15 H15D 113.0
C15 C16 H16A 110.5
C15 C16 H16B 110.5
H16A C16 H16B 108.7
C17 C16 C15 106.2(18)
C17 C16 H16A 110.5
C17 C16 H16B 110.5
C15 C16A H16C 110.2
C15 C16A H16D 110.2
H16C C16A H16D 108.5
C17A C16A C15 108(3)
C17A C16A H16C 110.2
C17A C16A H16D 110.2
C16A C17A H17D 109.5
C16A C17A H17E 109.5
C16A C17A H17F 109.5
H17D C17A H17E 109.5
H17D C17A H17F 109.5
H17E C17A H17F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C10 2.132(5)
O1 C7 1.358(5)
O1 C8 1.467(6)
O2 N1 1.427(5)
O2 C9 1.406(6)
N1 C7 1.270(6)
C1 H1 0.9300
C1 C2 1.380(8)
C1 C6 1.376(8)
C2 H2 0.9300
C2 C3 1.375(8)
C3 H3 0.9300
C3 C4 1.366(8)
C4 H4 0.9300
C4 C5 1.379(7)
C5 C6 1.387(7)
C5 C8 1.507(7)
C6 C7 1.454(7)
C8 C10 1.530(7)
C8 C14 1.514(7)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.317(7)
C11 C12 1.508(7)
C11 C13 1.508(7)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9700
C14 H14B 0.9700
C14 C15 1.510(10)
C15 H15A 0.9700
C15 H15B 0.9700
C15 H15C 0.9700
C15 H15D 0.9700
C15 C16 1.570(19)
C15 C16A 1.63(2)
C16 H16A 0.9700
C16 H16B 0.9700
C16 C17 1.42(4)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C16A H16C 0.9700
C16A H16D 0.9700
C16A C17A 1.34(5)
C17A H17D 0.9600
C17A H17E 0.9600
C17A H17F 0.9600
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
I1 C10 C11 C12 -179.4(4)
I1 C10 C11 C13 0.7(7)
O1 C8 C10 I1 167.8(3)
O1 C8 C10 C11 -12.3(7)
O1 C8 C14 C15 -63.2(6)
O2 N1 C7 O1 1.3(6)
O2 N1 C7 C6 -179.8(4)
C1 C2 C3 C4 -1.1(11)
C1 C6 C7 O1 176.8(5)
C1 C6 C7 N1 -2.3(8)
C2 C1 C6 C5 0.7(8)
C2 C1 C6 C7 -178.1(5)
C2 C3 C4 C5 -0.3(10)
C3 C4 C5 C6 1.8(9)
C3 C4 C5 C8 178.2(6)
C4 C5 C6 C1 -2.0(8)
C4 C5 C6 C7 177.0(5)
C4 C5 C8 O1 -174.6(6)
C4 C5 C8 C10 69.9(7)
C4 C5 C8 C14 -61.8(8)
C5 C6 C7 O1 -2.2(5)
C5 C6 C7 N1 178.7(5)
C5 C8 C10 I1 -79.3(4)
C5 C8 C10 C11 100.6(6)
C5 C8 C14 C15 -175.1(5)
C6 C1 C2 C3 0.9(10)
C6 C5 C8 O1 2.2(5)
C6 C5 C8 C10 -113.4(4)
C6 C5 C8 C14 114.9(5)
C7 O1 C8 C5 -3.5(5)
C7 O1 C8 C10 115.1(4)
C7 O1 C8 C14 -122.2(4)
C8 O1 C7 N1 -177.2(4)
C8 O1 C7 C6 3.7(5)
C8 C5 C6 C1 -179.2(5)
C8 C5 C6 C7 -0.1(5)
C8 C10 C11 C12 0.7(9)
C8 C10 C11 C13 -179.3(5)
C8 C14 C15 C16 158.4(11)
C8 C14 C15 C16A -179.8(11)
C9 O2 N1 C7 179.5(5)
C10 C8 C14 C15 54.6(7)
C14 C8 C10 I1 51.5(5)
C14 C8 C10 C11 -128.6(6)
C14 C15 C16 C17 70.9(19)
C14 C15 C16A C17A -177(2)
C16 C15 C16A C17A -28(2)
C16A C15 C16 C17 32(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304084
