#------------------------------------------------------------------------------
#$Date: 2024-07-02 04:19:49 +0300 (Tue, 02 Jul 2024) $
#$Revision: 292680 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/89/7248917.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_7248917
loop_
_publ_author_name
'Kotásková, Lucie'
'Jewula, Pawel'
'Herchel, Radovan'
'Nemec, Ivan'
'Neugebauer, Petr'
_publ_section_title
;
 Photoswitchable hydrazones with pyridine-based rotors and halogen
 substituents
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              20856
_journal_page_last               20866
_journal_paper_doi               10.1039/D4RA02909G
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H14 I N3 O2'
_chemical_formula_sum            'C15 H14 I N3 O2'
_chemical_formula_weight         395.19
_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             2023-10-18
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-02-25 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.506(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6839(2)
_cell_length_b                   18.5687(8)
_cell_length_c                   16.9966(6)
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.3040
_cell_measurement_theta_min      3.4770
_cell_volume                     1471.44(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  23.00   0.50    2.00    --  -43.25  81.00  14.00  114
  2  ω     -9.00  28.00   0.50    2.00    --   44.82 -81.00-108.00   74
  3  ω   -120.00 -94.00   0.50    6.00    --  -95.95  81.00  14.00   52
  4  ω   -151.00 -78.00   0.50    6.00    --  -95.95 -81.00-108.00  146
  5  ω     52.00  78.00   0.50    6.00    --   97.51 -81.00-108.00   52
  6  ω    122.00 147.00   0.50    6.00    --   97.51  81.00  14.00   50
  7  ω   -108.00 -28.00   0.50    2.00    --  -43.25 -54.00  90.00  160
  8  ω    -99.00 -74.00   0.50    2.00    --  -43.25-138.00   0.00   50
  9  ω    -19.00  22.00   0.50    2.00    --  -43.25  11.00  30.00   82
 10  ω   -108.00 -73.00   0.50    2.00    --  -43.25-138.00-150.00   70
 11  ω    -78.00 -49.00   0.50    2.00    --  -43.25 -32.00 -90.00   58
 12  ω   -108.00 -83.00   0.50    2.00    --  -43.25 -32.00 -90.00   50
 13  ω     -5.00  34.00   0.50    2.00    --   44.82 -32.00-120.00   78
 14  ω    -13.00  14.00   0.50    2.00    --   44.82 -21.00-180.00   54
 15  ω    -14.00  35.00   0.50    2.00    --   44.82 -32.00   0.00   98
 16  ω    -81.00 -51.00   0.50    6.00    --  -95.95  68.00  90.00   60
 17  ω   -163.00 -88.00   0.50    6.00    --  -95.95 -25.00-180.00  150
 18  ω   -118.00 -81.00   0.50    6.00    --  -95.95-117.00 -30.00   74
 19  ω    -88.00 -38.00   0.50    6.00    --  -95.95  81.00  14.00  100
 20  ω    -68.00 -32.00   0.50    6.00    --  -95.95  59.00   0.00   72
 21  ω   -106.00 -45.00   0.50    6.00    --  -95.95  96.00 120.00  122
 22  ω   -158.00 -79.00   0.50    6.00    --  -95.95 -86.00 -30.00  158
 23  ω   -161.00-126.00   0.50    6.00    --  -95.95-117.00 -30.00   70
 24  ω   -151.00-101.00   0.50    6.00    --  -95.95 -96.00 -60.00  100
 25  ω     31.00  56.00   0.50    6.00    --   97.51 -59.00-150.00   50
 26  ω     55.00  82.00   0.50    6.00    --   97.51 -68.00-120.00   54
 27  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00 150.00   50
 28  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00 -30.00   50
 29  ω     31.00  57.00   0.50    6.00    --   97.51 -50.00  90.00   52
 30  ω     81.00 163.00   0.50    6.00    --   97.51  50.00  60.00  164
 31  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00-120.00   50
 32  ω     34.00  59.00   0.50    6.00    --   97.51 -68.00  30.00   50
 33  ω     34.00  63.00   0.50    6.00    --   97.51 -59.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1091821000
_diffrn_orient_matrix_UB_12      -0.0490319000
_diffrn_orient_matrix_UB_13      -0.0637898000
_diffrn_orient_matrix_UB_21      -0.1208190000
_diffrn_orient_matrix_UB_22      0.0529245000
_diffrn_orient_matrix_UB_23      -0.0646209000
_diffrn_orient_matrix_UB_31      0.2874846000
_diffrn_orient_matrix_UB_32      0.0409427000
_diffrn_orient_matrix_UB_33      0.0071153000
_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  0.0441
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7046
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.574
_diffrn_reflns_theta_min         3.534
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    17.176
_exptl_absorpt_correction_T_max  0.396
_exptl_absorpt_correction_T_min  0.119
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.217
_refine_diff_density_min         -2.092
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0550
_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)+(0.1215P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2461
_reflns_number_total             2730
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra02909g2.cif
_cod_data_source_block           2-I
_cod_database_code               7248917
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C60  H56  I4  N12  O8  '
_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   0.340
_shelx_estimated_absorpt_t_min   0.086
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C10(H10), C8(H8), C6(H6), C5(H5), C9(H9), C3(H3A), C4(H4), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.466
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
I1 I 0.36498(7) 0.64388(2) 0.92807(2) 0.0354(2) Uani 1 1 d . . . . .
O2 O 0.4391(8) 0.6204(2) 0.5201(2) 0.0378(8) Uani 1 1 d . . . . .
O1 O 0.1459(9) 0.7129(2) 0.4925(2) 0.0423(9) Uani 1 1 d . . . . .
N3 N 0.3725(10) 0.6148(2) 0.7431(2) 0.0333(9) Uani 1 1 d . . . . .
H3 H 0.259647 0.642385 0.768627 0.040 Uiso 1 1 calc R U . . .
N2 N 0.3737(9) 0.6206(2) 0.6654(2) 0.0317(9) Uani 1 1 d . . . . .
N1 N -0.0048(10) 0.7148(2) 0.7380(2) 0.0353(9) Uani 1 1 d . . . . .
C1 C 0.5515(11) 0.5645(3) 0.7841(3) 0.0310(10) Uani 1 1 d . . . . .
C10 C -0.1741(11) 0.7664(3) 0.6139(3) 0.0350(11) Uani 1 1 d . . . . .
H10 H -0.167335 0.769094 0.558254 0.042 Uiso 1 1 calc R U . . .
C11 C 0.0034(11) 0.7177(3) 0.6592(3) 0.0312(10) Uani 1 1 d . . . . .
C8 C -0.3626(12) 0.8061(3) 0.7326(3) 0.0377(11) Uani 1 1 d . . . . .
H8 H -0.487219 0.835883 0.759196 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5679(11) 0.5632(3) 0.8667(3) 0.0326(10) Uani 1 1 d . . . . .
C6 C 0.7126(12) 0.5153(3) 0.7454(3) 0.0349(11) Uani 1 1 d . . . . .
H6 H 0.707147 0.516218 0.689414 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8817(12) 0.4648(3) 0.7885(3) 0.0370(11) Uani 1 1 d . . . . .
H5 H 0.992735 0.431652 0.761602 0.044 Uiso 1 1 calc R U . . .
C12 C 0.2068(12) 0.6679(3) 0.6260(3) 0.0335(10) Uani 1 1 d . . . . .
C9 C -0.3572(12) 0.8099(3) 0.6508(3) 0.0382(11) Uani 1 1 d . . . . .
H9 H -0.479853 0.842566 0.620727 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7325(12) 0.5117(3) 0.9089(3) 0.0360(11) Uani 1 1 d . . . . .
H3A H 0.736942 0.510317 0.964854 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2570(12) 0.6697(3) 0.5402(3) 0.0342(11) Uani 1 1 d . . . . .
C4 C 0.8900(12) 0.4622(3) 0.8705(3) 0.0378(11) Uani 1 1 d . . . . .
H4 H 1.002477 0.426896 0.899702 0.045 Uiso 1 1 calc R U . . .
C7 C -0.1804(12) 0.7574(3) 0.7737(3) 0.0403(12) Uani 1 1 d . . . . .
H7 H -0.180910 0.754465 0.829483 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5131(13) 0.6225(3) 0.4386(3) 0.0393(11) Uani 1 1 d . . . . .
H14A H 0.604739 0.669048 0.427862 0.047 Uiso 1 1 calc R U . . .
H14B H 0.338116 0.617183 0.401462 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7153(14) 0.5619(3) 0.4280(3) 0.0470(14) Uani 1 1 d . . . . .
H15A H 0.777717 0.563852 0.374656 0.070 Uiso 1 1 calc R U . . .
H15B H 0.618332 0.515999 0.435409 0.070 Uiso 1 1 calc R U . . .
H15C H 0.882517 0.566183 0.467051 0.070 Uiso 1 1 calc R U . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.0422
0 -1 1 0.0397
0 1 -1 0.0360
0 -2 1 0.0392
0 2 -1 0.0417
0 -1 0 0.0391
0 1 0 0.0417
2 1 0 0.1260
-1 1 0 0.1424
1 2 0 0.1217
0 0 1 0.0399
0 -1 -2 0.0475
-1 -1 2 0.1255
-1 0 2 0.1336
1 0 -2 0.1214
0 -1 -1 0.0452
0 1 2 0.0337
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
C13 O2 C14 116.5(4) . . ?
N2 N3 H3 120.2 . . ?
N2 N3 C1 119.5(4) . . ?
C1 N3 H3 120.2 . . ?
C12 N2 N3 120.2(4) . . ?
C7 N1 C11 120.5(5) . . ?
N3 C1 C2 119.1(5) . . ?
C6 C1 N3 122.0(4) . . ?
C6 C1 C2 118.9(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.3(5) . . ?
N1 C11 C10 120.0(5) . . ?
N1 C11 C12 115.9(4) . . ?
C10 C11 C12 124.1(4) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C9 117.9(5) . . ?
C1 C2 I1 120.1(4) . . ?
C3 C2 I1 119.4(4) . . ?
C3 C2 C1 120.4(5) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.7(5) . . ?
C4 C5 H5 119.7 . . ?
N2 C12 C11 126.6(4) . . ?
N2 C12 C13 111.7(4) . . ?
C11 C12 C13 121.7(4) . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3A 119.6 . . ?
O2 C13 C12 113.7(4) . . ?
O1 C13 O2 121.9(5) . . ?
O1 C13 C12 124.3(5) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?
N1 C7 C8 122.5(5) . . ?
N1 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
O2 C14 H14A 110.2 . . ?
O2 C14 H14B 110.2 . . ?
O2 C14 C15 107.8(4) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 C2 2.104(5) . ?
O2 C13 1.319(7) . ?
O2 C14 1.460(6) . ?
O1 C13 1.220(6) . ?
N3 H3 0.8800 . ?
N3 N2 1.326(6) . ?
N3 C1 1.395(6) . ?
N2 C12 1.316(7) . ?
N1 C11 1.345(6) . ?
N1 C7 1.329(7) . ?
C1 C2 1.399(6) . ?
C1 C6 1.391(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.407(7) . ?
C10 C9 1.374(8) . ?
C11 C12 1.478(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(8) . ?
C8 C7 1.385(8) . ?
C2 C3 1.385(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.393(7) . ?
C12 C13 1.499(7) . ?
C9 H9 0.9500 . ?
C3 H3A 0.9500 . ?
C3 C4 1.380(8) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.492(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0005 1.0016 -1.9997 0.0785 0.1822 0.0269
-0.0007 -1.0006 0.9996 -0.0148 -0.1175 -0.0340
0.0007 1.0006 -0.9996 0.0148 0.1175 0.0340
-0.0015 -2.0001 0.9991 0.0342 -0.1702 -0.0752
0.0015 2.0001 -0.9991 -0.0342 0.1702 0.0752
-0.0008 -0.9996 -0.0005 0.0490 -0.0528 -0.0412
0.0008 0.9996 0.0005 -0.0490 0.0528 0.0412
2.0014 0.9903 -0.0047 0.1703 -0.1891 0.6159
-0.9994 1.0042 0.0032 -0.1586 0.1737 -0.2462
1.0019 1.9945 -0.0015 0.0117 -0.0154 0.3697
0.0002 -0.0010 1.0001 -0.0637 -0.0647 0.0071
-0.0011 -0.9976 -2.0008 0.1764 0.0766 -0.0554
-1.0008 -0.9969 2.0024 -0.1881 -0.0612 -0.3143
-0.9999 0.0027 2.0029 -0.2371 -0.0085 -0.2731
0.9999 -0.0027 -2.0029 0.2371 0.0085 0.2731
-0.0010 -0.9986 -1.0007 0.1127 0.0119 -0.0483
0.0011 0.9976 2.0008 -0.1764 -0.0766 0.0554
