#------------------------------------------------------------------------------
#$Date: 2025-08-20 20:34:49 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301835 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/39/4133920.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_4133920
loop_
_publ_author_name
'Jin, Shengfei'
'Dang, Hang T.'
'Haug, Graham C.'
'He, Ru'
'Nguyen, Viet D.'
'Nguyen, Vu T.'
'Arman, Hadi D.'
'Schanze, Kirk S.'
'Larionov, Oleg V.'
_publ_section_title
;
 Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1603
_journal_page_last               1613
_journal_paper_doi               10.1021/jacs.9b12519
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C18 H22 I N O4'
_chemical_formula_sum            'C18 H22 I N O4'
_chemical_formula_weight         443.26
_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             2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.458(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7645(4)
_cell_length_b                   7.7901(2)
_cell_length_c                   16.2371(4)
_cell_measurement_reflns_used    28664
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.9500
_cell_measurement_theta_min      2.5740
_cell_volume                     1781.52(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -85.00  39.00   1.00    4.08    --    4.20 -23.00  91.00  124
  2  ω    -42.00  82.00   1.00    4.08    --   -7.70  23.00-103.00  124
  3  ω    -97.00  23.00   1.00    4.08    --   -7.70 -57.00-180.00  120
  4  ω    -97.00  18.00   1.00    4.08    --   -7.70 -38.00 -90.00  115
  5  ω    -38.00  82.00   1.00    4.08    --   -7.70  57.00 120.00  120
  6  ω    -38.00  82.00   1.00    4.08    --   -7.70  57.00 -60.00  120
  7  ω    -97.00  23.00   1.00    4.08    --   -7.70 -57.00   0.00  120
  8  ω    -38.00  82.00   1.00    4.08    --   -7.70  57.00   0.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0373614000
_diffrn_orient_matrix_UB_12      0.0041195000
_diffrn_orient_matrix_UB_13      -0.0190312000
_diffrn_orient_matrix_UB_21      0.0326957000
_diffrn_orient_matrix_UB_22      -0.0271158000
_diffrn_orient_matrix_UB_23      0.0394984000
_diffrn_orient_matrix_UB_31      -0.0084584000
_diffrn_orient_matrix_UB_32      -0.0868050000
_diffrn_orient_matrix_UB_33      -0.0132499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46440
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_min         2.593
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.33
_refine_diff_density_max         1.175
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0336
_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)+(0.0550P)²+4.5126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3312
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cd1921c.cif
_cod_data_source_block           cd1921c
_cod_depositor_comments
'Adding full bibliography for 4133912--4133933.cif.'
_cod_database_code               4133920
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C17H22O2N1I
_chemical_oxdiff_usercomment     'Larianov NMR sample :)'
_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_max   0.585
_shelx_estimated_absorpt_t_min   0.463
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C17(H17A,H17B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.132
_oxdiff_exptl_absorpt_empirical_full_min 0.902
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
I1 I 0.43570(2) 0.72064(3) 0.38933(2) 0.01328(11) Uani 1 1 d .
O2 O 0.70786(17) 0.1738(3) 0.51314(15) 0.0129(5) Uani 1 1 d .
O3 O 0.86601(17) -0.0146(3) 0.64304(15) 0.0172(5) Uani 1 1 d .
O4 O 0.98727(18) 0.1628(4) 0.64878(17) 0.0212(6) Uani 1 1 d .
O1 O 0.8772(2) 0.2106(4) 0.33673(19) 0.0245(7) Uani 1 1 d .
N1 N 0.7875(2) 0.4527(4) 0.29172(18) 0.0146(6) Uani 1 1 d .
H1 H 0.817419 0.493427 0.256518 0.017 Uiso 1 1 calc R
C2 C 0.6606(3) 0.6781(5) 0.2666(2) 0.0125(7) Uani 1 1 d .
C6 C 0.6792(2) 0.4352(4) 0.3665(2) 0.0125(7) Uani 1 1 d .
C4 C 0.5525(2) 0.6336(4) 0.3521(2) 0.0122(7) Uani 1 1 d .
C3 C 0.5816(3) 0.7267(5) 0.2913(2) 0.0133(7) Uani 1 1 d .
H3 H 0.546687 0.825816 0.266057 0.016 Uiso 1 1 calc R
C1 C 0.7074(2) 0.5306(4) 0.3054(2) 0.0112(7) Uani 1 1 d .
C9 C 0.6911(3) 0.7772(5) 0.1995(2) 0.0162(8) Uani 1 1 d .
H9A H 0.676770 0.900415 0.203780 0.019 Uiso 1 1 calc R
H9B H 0.760543 0.765283 0.211213 0.019 Uiso 1 1 calc R
C5 C 0.6005(2) 0.4862(5) 0.3902(2) 0.0122(7) Uani 1 1 d .
H5 H 0.579999 0.422553 0.431229 0.015 Uiso 1 1 calc R
C8 C 0.8136(3) 0.3062(5) 0.3393(2) 0.0156(8) Uani 1 1 d .
C7 C 0.7434(3) 0.2811(4) 0.3925(2) 0.0128(7) Uani 1 1 d .
C11 C 0.6894(3) 0.1094(5) 0.3656(2) 0.0161(7) Uani 1 1 d .
H11A H 0.631756 0.126493 0.315904 0.019 Uiso 1 1 calc R
H11B H 0.730426 0.022829 0.349929 0.019 Uiso 1 1 calc R
C15 C 0.9061(2) 0.0836(5) 0.6082(2) 0.0142(7) Uani 1 1 d .
C12 C 0.6631(3) 0.0539(5) 0.4459(2) 0.0181(8) Uani 1 1 d .
H12A H 0.593372 0.055954 0.434309 0.022 Uiso 1 1 calc R
H12B H 0.686193 -0.064015 0.463034 0.022 Uiso 1 1 calc R
C13 C 0.7860(3) 0.2541(4) 0.4924(2) 0.0118(7) Uani 1 1 d .
C17 C 0.8074(2) 0.4170(5) 0.5472(2) 0.0151(7) Uani 1 1 d .
H17A H 0.827970 0.383778 0.608879 0.018 Uiso 1 1 calc R
H17B H 0.748040 0.484118 0.536539 0.018 Uiso 1 1 calc R
C14 C 0.8725(3) 0.1307(5) 0.5139(2) 0.0159(7) Uani 1 1 d .
H14A H 0.854799 0.024809 0.478986 0.019 Uiso 1 1 calc R
H14B H 0.925185 0.186153 0.497845 0.019 Uiso 1 1 calc R
C10 C 0.6416(4) 0.7149(5) 0.1093(3) 0.0292(11) Uani 1 1 d .
H10A H 0.662473 0.783304 0.067750 0.044 Uiso 1 1 calc GR
H10B H 0.572766 0.726949 0.097390 0.044 Uiso 1 1 calc GR
H10C H 0.657313 0.593917 0.104265 0.044 Uiso 1 1 calc GR
C18 C 0.8837(3) 0.5326(6) 0.5300(3) 0.0258(9) Uani 1 1 d .
H18A H 0.866153 0.560643 0.468413 0.039 Uiso 1 1 calc GR
H18B H 0.944819 0.472535 0.547066 0.039 Uiso 1 1 calc GR
H18C H 0.888907 0.638612 0.563645 0.039 Uiso 1 1 calc GR
C16 C 1.0287(3) 0.1186(6) 0.7393(2) 0.0238(9) Uani 1 1 d .
H16A H 1.047382 -0.002547 0.744267 0.036 Uiso 1 1 calc GR
H16B H 0.981894 0.138292 0.770235 0.036 Uiso 1 1 calc GR
H16C H 1.084700 0.190344 0.764545 0.036 Uiso 1 1 calc 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'
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'
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
C13 O2 C12 108.8(2)
C15 O4 C16 115.6(3)
C1 N1 H1 123.9
C8 N1 H1 123.9
C8 N1 C1 112.2(3)
C3 C2 C9 121.7(3)
C1 C2 C3 116.0(3)
C1 C2 C9 122.4(3)
C1 C6 C7 108.9(3)
C5 C6 C1 119.8(3)
C5 C6 C7 131.2(3)
C3 C4 I1 119.3(3)
C3 C4 C5 121.4(3)
C5 C4 I1 119.3(2)
C2 C3 H3 119.2
C4 C3 C2 121.6(3)
C4 C3 H3 119.2
C2 C1 N1 127.7(3)
C2 C1 C6 123.2(3)
C6 C1 N1 109.1(3)
C2 C9 H9A 109.2
C2 C9 H9B 109.2
H9A C9 H9B 107.9
C10 C9 C2 112.0(3)
C10 C9 H9A 109.2
C10 C9 H9B 109.2
C6 C5 C4 118.0(3)
C6 C5 H5 121.0
C4 C5 H5 121.0
O1 C8 N1 125.7(3)
O1 C8 C7 126.8(3)
N1 C8 C7 107.4(3)
C6 C7 C8 102.3(3)
C6 C7 C11 112.4(3)
C6 C7 C13 114.7(3)
C8 C7 C11 109.0(3)
C8 C7 C13 117.8(3)
C11 C7 C13 100.9(3)
C7 C11 H11A 110.9
C7 C11 H11B 110.9
H11A C11 H11B 108.9
C12 C11 C7 104.1(3)
C12 C11 H11A 110.9
C12 C11 H11B 110.9
O3 C15 O4 123.8(3)
O3 C15 C14 125.0(3)
O4 C15 C14 111.2(3)
O2 C12 C11 106.7(3)
O2 C12 H12A 110.4
O2 C12 H12B 110.4
C11 C12 H12A 110.4
C11 C12 H12B 110.4
H12A C12 H12B 108.6
O2 C13 C7 101.5(3)
O2 C13 C17 105.4(3)
O2 C13 C14 110.0(3)
C17 C13 C7 116.1(3)
C17 C13 C14 111.8(3)
C14 C13 C7 111.3(3)
C13 C17 H17A 108.6
C13 C17 H17B 108.6
C13 C17 C18 114.7(3)
H17A C17 H17B 107.6
C18 C17 H17A 108.6
C18 C17 H17B 108.6
C15 C14 C13 112.1(3)
C15 C14 H14A 109.2
C15 C14 H14B 109.2
C13 C14 H14A 109.2
C13 C14 H14B 109.2
H14A C14 H14B 107.9
C9 C10 H10A 109.5
C9 C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C17 C18 H18A 109.5
C17 C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18B 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O4 C16 H16A 109.5
O4 C16 H16B 109.5
O4 C16 H16C 109.5
H16A C16 H16B 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C4 2.104(3)
O2 C12 1.438(4)
O2 C13 1.438(4)
O3 C15 1.206(4)
O4 C15 1.334(4)
O4 C16 1.454(5)
O1 C8 1.210(5)
N1 H1 0.8800
N1 C1 1.406(4)
N1 C8 1.367(5)
C2 C3 1.396(5)
C2 C1 1.391(5)
C2 C9 1.509(5)
C6 C1 1.399(5)
C6 C5 1.386(5)
C6 C7 1.510(5)
C4 C3 1.392(5)
C4 C5 1.393(5)
C3 H3 0.9500
C9 H9A 0.9900
C9 H9B 0.9900
C9 C10 1.507(6)
C5 H5 0.9500
C8 C7 1.548(5)
C7 C11 1.551(5)
C7 C13 1.568(5)
C11 H11A 0.9900
C11 H11B 0.9900
C11 C12 1.530(5)
C15 C14 1.507(5)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C17 1.528(5)
C13 C14 1.553(5)
C17 H17A 0.9900
C17 H17B 0.9900
C17 C18 1.531(5)
C14 H14A 0.9900
C14 H14B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336036
