#------------------------------------------------------------------------------
#$Date: 2023-10-10 00:56:30 +0300 (Tue, 10 Oct 2023) $
#$Revision: 286850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132191.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_7132191
loop_
_publ_author_name
'Ahsan, Mollah Rohan'
'Singh, Lavanya'
'Varma, Harshit'
'Mukherjee, Arijit'
_publ_section_title
;
 Exploiting benzilic acid as a modular template: controlling
 photoreactivity and solid to liquid transition during photodimerization.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc04257j
_journal_year                    2023
_chemical_formula_moiety         'C14 H12 O3, C5 H4 I N'
_chemical_formula_sum            'C19 H16 I N O3'
_chemical_formula_weight         433.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-08-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-21 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                83.149(2)
_cell_angle_beta                 86.845(2)
_cell_angle_gamma                83.349(2)
_cell_formula_units_Z            2
_cell_length_a                   6.45360(10)
_cell_length_b                   8.3751(2)
_cell_length_c                   16.1607(5)
_cell_measurement_reflns_used    6639
_cell_measurement_temperature    140
_cell_measurement_theta_max      79.3380
_cell_measurement_theta_min      5.3650
_cell_volume                     860.65(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  32.00   0.50    0.50    --    0.00 -82.00  30.00  242
  2  ω    -89.00 -32.00   0.50    0.50    --    0.00   0.00  90.00  114
  3  ω    -15.00  50.00   0.50    0.50    --    0.00  37.00-150.00  130
  4  ω      5.00  30.00   0.50    0.50    --    0.00   0.00  90.00   50
  5  ω     18.00 134.00   0.50    1.00    --  107.20 -15.00 -60.00  232
  6  ω     25.00  51.00   0.50    1.00    --  107.20 -30.00-150.00   52
  7  ω     56.00 137.00   0.50    1.00    --  107.20 -82.00-150.00  162
  8  ω     91.00 116.00   0.50    1.00    --  107.20 -82.00  60.00   50
  9  ω     80.00 196.00   0.50    1.00    --  107.20  15.00 -30.00  232
 10  ω     19.00  71.00   0.50    1.00    --  107.20 -82.00-120.00  104
 11  ω     86.00 138.00   0.50    1.00    --  107.20 -82.00-120.00  104
 12  ω     40.00 136.00   0.50    1.00    --  107.20 -82.00   0.00  192
 13  ω     21.00  85.00   0.50    1.00    --  107.20 -61.00 150.00  128
 14  ω     80.00 149.00   0.50    1.00    --  107.20  15.00 -90.00  138
 15  ω     72.00  98.00   0.50    1.00    --  107.20 -82.00 -30.00   52
 16  ω     22.00 136.00   0.50    1.00    --  107.20 -82.00 150.00  228
 17  ω    171.00 197.00   0.50    1.00    --  107.20  15.00 -90.00   52
 18  ω     43.00  76.00   0.50    1.00    --  107.20 -82.00  60.00   66
 19  ω     57.00 120.00   0.50    1.00    --  107.20 -30.00-150.00  126
 20  ω    152.00 177.00   0.50    1.00    --  107.20  30.00-180.00   50
 21  ω     96.00 128.00   0.50    1.00    --  107.20 -45.00   0.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0367045000
_diffrn_orient_matrix_UB_12      0.0706228000
_diffrn_orient_matrix_UB_13      0.0840188000
_diffrn_orient_matrix_UB_21      0.2247831000
_diffrn_orient_matrix_UB_22      -0.0653925000
_diffrn_orient_matrix_UB_23      0.0233234000
_diffrn_orient_matrix_UB_31      0.0773656000
_diffrn_orient_matrix_UB_32      0.1596331000
_diffrn_orient_matrix_UB_33      -0.0403927000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8384
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.796
_diffrn_reflns_theta_min         5.352
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
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    1.672
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.569
_refine_diff_density_min         -1.524
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0399
_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)+(0.0572P)²+2.3242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3506
_reflns_number_total             3605
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04257j2.cif
_cod_data_source_block           260-nme-crysalis
_cod_database_code               7132191
_shelx_shelxl_version_number     2019/3
_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   0.320
_shelx_estimated_absorpt_t_min   0.156
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C20(H20), C24(H24), C13(H13), C21(H21), C9(H9), C19(H19), C15(H15),
 C10(H10), C18(H18), C11(H11), C16(H16), C17(H17), C12(H12)
;
_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 2.302
_oxdiff_exptl_absorpt_empirical_full_min 0.590
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
I1 I 1.25210(4) -0.36426(3) 0.50054(2) 0.03158(12) Uani 1 1 d . . . . .
O2 O 0.5708(5) 0.2651(4) 0.25244(19) 0.0259(6) Uani 1 1 d . . . . .
O4 O 0.0707(5) 0.4883(4) 0.28265(19) 0.0281(6) Uani 1 1 d . . . . .
O3 O 0.3325(5) 0.2669(4) 0.35799(19) 0.0323(7) Uani 1 1 d . . . . .
N5 N 0.8004(6) 0.0490(4) 0.3413(2) 0.0238(7) Uani 1 1 d . . . . .
C14 C 0.3678(6) 0.6067(5) 0.2166(2) 0.0211(7) Uani 1 1 d . . . . .
C7 C 0.2597(6) 0.4520(5) 0.2353(2) 0.0190(7) Uani 1 1 d . . . . .
C8 C 0.2127(6) 0.3876(5) 0.1540(2) 0.0204(7) Uani 1 1 d . . . . .
C22 C 1.0539(6) -0.1890(5) 0.4312(2) 0.0225(7) Uani 1 1 d . . . . .
C6 C 0.3950(6) 0.3168(5) 0.2882(2) 0.0194(7) Uani 1 1 d . . . . .
C23 C 1.1345(6) -0.1045(5) 0.3596(3) 0.0240(8) Uani 1 1 d . . . . .
H23 H 1.275702 -0.127663 0.340950 0.029 Uiso 1 1 calc R U . . .
C20 C 0.7264(7) -0.0345(5) 0.4096(3) 0.0262(8) Uani 1 1 d . . . . .
H20 H 0.583881 -0.010574 0.426431 0.031 Uiso 1 1 calc R U . . .
C24 C 1.0009(7) 0.0152(5) 0.3164(3) 0.0248(8) Uani 1 1 d . . . . .
H24 H 1.053331 0.074932 0.267560 0.030 Uiso 1 1 calc R U . . .
C13 C 0.0171(6) 0.3425(5) 0.1421(3) 0.0250(8) Uani 1 1 d . . . . .
H13 H -0.091664 0.355960 0.183605 0.030 Uiso 1 1 calc R U . . .
C21 C 0.8470(7) -0.1542(5) 0.4570(3) 0.0268(8) Uani 1 1 d . . . . .
H21 H 0.790159 -0.210977 0.505868 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3688(7) 0.3709(5) 0.0909(3) 0.0252(8) Uani 1 1 d . . . . .
H9 H 0.502403 0.403620 0.097762 0.030 Uiso 1 1 calc R U . . .
C19 C 0.5616(7) 0.6253(5) 0.2454(3) 0.0256(8) Uani 1 1 d . . . . .
H19 H 0.636235 0.538057 0.278361 0.031 Uiso 1 1 calc R U . . .
C15 C 0.2600(7) 0.7379(5) 0.1696(3) 0.0284(9) Uani 1 1 d . . . . .
H15 H 0.126676 0.727716 0.149968 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3306(8) 0.3074(6) 0.0189(3) 0.0311(9) Uani 1 1 d . . . . .
H10 H 0.437571 0.297005 -0.023514 0.037 Uiso 1 1 calc R U . . .
C18 C 0.6471(8) 0.7713(6) 0.2262(3) 0.0340(10) Uani 1 1 d . . . . .
H18 H 0.780684 0.782196 0.245363 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1352(8) 0.2585(6) 0.0083(3) 0.0336(10) Uani 1 1 d . . . . .
H11 H 0.109520 0.212485 -0.040580 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3461(9) 0.8833(5) 0.1513(3) 0.0369(11) Uani 1 1 d . . . . .
H16 H 0.271476 0.971684 0.119205 0.044 Uiso 1 1 calc R U . . .
C17 C 0.5402(9) 0.8999(6) 0.1797(3) 0.0386(11) Uani 1 1 d . . . . .
H17 H 0.598998 0.999231 0.167151 0.046 Uiso 1 1 calc R U . . .
C12 C -0.0205(7) 0.2776(6) 0.0695(3) 0.0334(10) Uani 1 1 d . . . . .
H12 H -0.154467 0.246210 0.062168 0.040 Uiso 1 1 calc R U . . .
H4 H 0.092(10) 0.432(8) 0.333(4) 0.044(17) Uiso 1 1 d . . . . .
H2 H 0.645(12) 0.180(10) 0.296(5) 0.06(2) Uiso 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'
I I -0.3257 6.8362 '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'
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
C6 O2 H2 106(4) . . ?
C7 O4 H4 104(4) . . ?
C20 N5 C24 119.1(4) . . ?
C19 C14 C7 124.2(4) . . ?
C19 C14 C15 118.6(4) . . ?
C15 C14 C7 117.2(4) . . ?
O4 C7 C14 108.4(3) . . ?
O4 C7 C8 110.2(3) . . ?
O4 C7 C6 107.3(3) . . ?
C14 C7 C8 110.7(3) . . ?
C14 C7 C6 111.9(3) . . ?
C8 C7 C6 108.3(3) . . ?
C13 C8 C7 121.0(3) . . ?
C13 C8 C9 118.8(4) . . ?
C9 C8 C7 120.2(3) . . ?
C23 C22 I1 118.9(3) . . ?
C21 C22 I1 120.8(3) . . ?
C21 C22 C23 120.3(4) . . ?
O2 C6 C7 115.1(3) . . ?
O3 C6 O2 125.2(4) . . ?
O3 C6 C7 119.7(3) . . ?
C22 C23 H23 121.2 . . ?
C22 C23 C24 117.6(4) . . ?
C24 C23 H23 121.2 . . ?
N5 C20 H20 118.5 . . ?
N5 C20 C21 123.0(4) . . ?
C21 C20 H20 118.5 . . ?
N5 C24 C23 122.2(4) . . ?
N5 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C8 C13 H13 119.9 . . ?
C8 C13 C12 120.3(4) . . ?
C12 C13 H13 119.9 . . ?
C22 C21 H21 121.1 . . ?
C20 C21 C22 117.8(4) . . ?
C20 C21 H21 121.1 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.7 . . ?
C14 C19 H19 119.9 . . ?
C14 C19 C18 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C19 C18 H18 119.6 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C13 C12 H12 119.7 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
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 C22 2.092(4) . ?
O2 C6 1.297(5) . ?
O2 H2 1.03(8) . ?
O4 C7 1.426(4) . ?
O4 H4 0.90(7) . ?
O3 C6 1.218(5) . ?
N5 C20 1.331(6) . ?
N5 C24 1.342(5) . ?
C14 C7 1.532(5) . ?
C14 C19 1.390(6) . ?
C14 C15 1.396(6) . ?
C7 C8 1.536(5) . ?
C7 C6 1.549(5) . ?
C8 C13 1.389(5) . ?
C8 C9 1.401(5) . ?
C22 C23 1.390(6) . ?
C22 C21 1.386(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(6) . ?
C24 H24 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.394(6) . ?
C21 H21 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.382(6) . ?
C19 H19 0.9500 . ?
C19 C18 1.394(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(7) . ?
C18 H18 0.9500 . ?
C18 C17 1.375(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(8) . ?
C17 H17 0.9500 . ?
C12 H12 0.9500 . ?
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
I1 C22 C23 C24 -177.8(3) . . . . ?
I1 C22 C21 C20 178.4(3) . . . . ?
O4 C7 C8 C13 -12.3(5) . . . . ?
O4 C7 C8 C9 168.7(3) . . . . ?
O4 C7 C6 O2 177.5(3) . . . . ?
O4 C7 C6 O3 -2.3(5) . . . . ?
N5 C20 C21 C22 -0.7(7) . . . . ?
C14 C7 C8 C13 -132.2(4) . . . . ?
C14 C7 C8 C9 48.8(5) . . . . ?
C14 C7 C6 O2 -63.7(4) . . . . ?
C14 C7 C6 O3 116.5(4) . . . . ?
C14 C19 C18 C17 1.0(7) . . . . ?
C14 C15 C16 C17 -0.1(7) . . . . ?
C7 C14 C19 C18 -179.2(4) . . . . ?
C7 C14 C15 C16 178.9(4) . . . . ?
C7 C8 C13 C12 -177.2(4) . . . . ?
C7 C8 C9 C10 177.5(4) . . . . ?
C8 C7 C6 O2 58.6(4) . . . . ?
C8 C7 C6 O3 -121.2(4) . . . . ?
C8 C13 C12 C11 -0.5(7) . . . . ?
C8 C9 C10 C11 -0.2(7) . . . . ?
C22 C23 C24 N5 -0.5(6) . . . . ?
C6 C7 C8 C13 104.7(4) . . . . ?
C6 C7 C8 C9 -74.2(4) . . . . ?
C23 C22 C21 C20 0.1(6) . . . . ?
C20 N5 C24 C23 0.0(6) . . . . ?
C24 N5 C20 C21 0.7(6) . . . . ?
C13 C8 C9 C10 -1.4(6) . . . . ?
C21 C22 C23 C24 0.5(6) . . . . ?
C9 C8 C13 C12 1.8(6) . . . . ?
C9 C10 C11 C12 1.5(7) . . . . ?
C19 C14 C7 O4 116.6(4) . . . . ?
C19 C14 C7 C8 -122.4(4) . . . . ?
C19 C14 C7 C6 -1.5(5) . . . . ?
C19 C14 C15 C16 0.7(6) . . . . ?
C19 C18 C17 C16 -0.4(7) . . . . ?
C15 C14 C7 O4 -61.5(4) . . . . ?
C15 C14 C7 C8 59.5(4) . . . . ?
C15 C14 C7 C6 -179.6(3) . . . . ?
C15 C14 C19 C18 -1.1(6) . . . . ?
C15 C16 C17 C18 0.0(7) . . . . ?
C10 C11 C12 C13 -1.1(7) . . . . ?
