#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:20:31 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567656.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_1567656
loop_
_publ_author_name
'Kerckhoffs, Aidan'
'Christensen, Kirsten E.'
'Langton, Matthew J.'
_publ_section_title
;
 Fast relaxing red and near-IR switchable azobenzenes with chalcogen and
 halogen substituents: periodic trends, tuneable thermal half-lives and
 chalcogen bonding.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              11551
_journal_page_last               11559
_journal_paper_doi               10.1039/d2sc04601f
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 I4 N2 O4'
_chemical_formula_sum            'C18 H14 I4 N2 O4'
_chemical_formula_weight         829.94
_chemical_melting_point          ?
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2022-05-17
_audit_creation_method           'CRYSTALS_ver_*****_build_8199 '
_audit_update_record
;
2022-08-10 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.636(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0017(3)
_cell_length_b                   8.23620(10)
_cell_length_c                   19.1456(4)
_cell_measurement_reflns_used    12224
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.34
_cell_measurement_theta_min      4.74
_cell_volume                     2136.24(7)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_unetI/netI     0.055
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18739
_diffrn_reflns_theta_full        74.904
_diffrn_reflns_theta_max         76.433
_diffrn_reflns_theta_min         5.058
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    46.060
_exptl_absorpt_correction_T_max  0.02
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_dark_red
_exptl_crystal_density_diffrn    2.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         4.27
_refine_diff_density_min         -1.58
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0694
_refine_ls_shift/su_max          0.0008691
_refine_ls_shift/su_mean         0.0000299
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.16P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1791
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1791
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                4175
_reflns_number_total             4444
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.73
_oxford_diffrn_Wilson_scale      0.52
_oxford_refine_ls_scale          1.405(15)
_oxford_structure_analysis_title 7632
_cod_data_source_file            d2sc04601f2.cif
_cod_data_source_block           3-I4-ester
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1567655--1567664.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               1567656
_oxford_refine_reflns_threshold_expression I>-10.0\s(I)
_refine_ls_r_factor_ref          0.0716
_reflns_number_all               4443
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.7444(4) 0.5418(7) 0.7249(4) 0.0324 1.0000 Uani . . . . . .
C2 C 0.6814(5) 0.5725(7) 0.6544(4) 0.0311 1.0000 Uani . . . . . .
C3 C 0.5945(5) 0.6621(8) 0.6516(4) 0.0347 1.0000 Uani . . . . . .
C4 C 0.5344(5) 0.7105(8) 0.5860(4) 0.0341 1.0000 Uani . . . . . .
C5 C 0.5591(5) 0.6710(8) 0.5219(4) 0.0315 1.0000 Uani . . . . . .
C6 C 0.6449(5) 0.5817(7) 0.5246(4) 0.0338 1.0000 Uani . . . . . .
C7 C 0.7064(5) 0.5342(8) 0.5898(4) 0.0330 1.0000 Uani . . . . . .
I8 I 0.55713(3) 0.72824(5) 0.74603(2) 0.0339 1.0000 Uani . . . . . .
I9 I 0.84036(3) 0.42716(5) 0.58374(3) 0.0362 1.0000 Uani . . . . . .
C10 C 0.5007(5) 0.7258(8) 0.4486(5) 0.0359 1.0000 Uani . . . . . .
O11 O 0.5217(4) 0.6850(7) 0.3942(3) 0.0396 1.0000 Uani . . . . . .
O12 O 0.4281(4) 0.8275(6) 0.4517(3) 0.0358 1.0000 Uani . . . . . .
C13 C 0.3708(6) 0.8852(9) 0.3807(4) 0.0372 1.0000 Uani . . . . . .
C14 C 0.2863(6) 0.9840(9) 0.3930(4) 0.0390 1.0000 Uani . . . . . .
N21 N 0.7795(4) 0.4017(7) 0.7340(4) 0.0337 1.0000 Uani . . . . . .
C22 C 0.8526(4) 0.3834(8) 0.8010(4) 0.0304 1.0000 Uani . . . . . .
C23 C 0.8496(5) 0.2431(8) 0.8429(4) 0.0310 1.0000 Uani . . . . . .
C24 C 0.9205(5) 0.2146(8) 0.9055(4) 0.0328 1.0000 Uani . . . . . .
C25 C 0.9994(5) 0.3226(8) 0.9286(4) 0.0317 1.0000 Uani . . . . . .
C26 C 1.0066(5) 0.4604(8) 0.8870(4) 0.0361 1.0000 Uani . . . . . .
C27 C 0.9329(5) 0.4902(8) 0.8242(4) 0.0323 1.0000 Uani . . . . . .
I28 I 0.73427(3) 0.07665(5) 0.81360(3) 0.0382 1.0000 Uani . . . . . .
I29 I 0.95310(3) 0.69802(5) 0.76600(3) 0.0394 1.0000 Uani . . . . . .
C30 C 1.0735(5) 0.2906(8) 0.9990(4) 0.0345 1.0000 Uani . . . . . .
O31 O 1.0585(4) 0.1933(7) 1.0428(3) 0.0398 1.0000 Uani . . . . . .
O32 O 1.1539(4) 0.3798(7) 1.0070(3) 0.0383 1.0000 Uani . . . . . .
C33 C 1.2285(5) 0.3618(9) 1.0749(4) 0.0382 1.0000 Uani . . . . . .
H41 H 0.4773 0.7700 0.5851 0.0409 1.0000 Uiso R . . . . .
H61 H 0.6608 0.5533 0.4823 0.0408 1.0000 Uiso R . . . . .
H131 H 0.4120 0.9513 0.3585 0.0451 1.0000 Uiso R . . . . .
H132 H 0.3452 0.7937 0.3499 0.0450 1.0000 Uiso R . . . . .
H142 H 0.2521 1.0321 0.3481 0.0580 1.0000 Uiso R . . . . .
H141 H 0.3116 1.0676 0.4277 0.0581 1.0000 Uiso R . . . . .
H143 H 0.2426 0.9135 0.4103 0.0578 1.0000 Uiso R . . . . .
H241 H 0.9160 0.1224 0.9329 0.0389 1.0000 Uiso R . . . . .
H261 H 1.0599 0.5312 0.9012 0.0432 1.0000 Uiso R . . . . .
C34 C 1.2997(6) 0.5021(10) 1.0792(5) 0.0412 1.0000 Uani . . . . . .
H331 H 1.1981 0.3654 1.1149 0.0458 1.0000 Uiso R . . . . .
H332 H 1.2627 0.2601 1.0750 0.0461 1.0000 Uiso R . . . . .
H342 H 1.3346 0.5188 1.1288 0.0621 1.0000 Uiso R . . . . .
H341 H 1.2638 0.5989 1.0607 0.0620 1.0000 Uiso R . . . . .
H343 H 1.3456 0.4768 1.0507 0.0619 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . N21 . 114.9(6) yes
N1 . C2 . C3 . 116.6(6) yes
N1 . C2 . C7 . 123.9(6) yes
C3 . C2 . C7 . 119.2(6) yes
C2 . C3 . C4 . 120.5(7) yes
C2 . C3 . I8 . 120.5(5) yes
C4 . C3 . I8 . 119.0(5) yes
C3 . C4 . C5 . 120.2(6) yes
C3 . C4 . H41 . 119.4 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 119.5(7) yes
C4 . C5 . C10 . 123.6(6) yes
C6 . C5 . C10 . 116.8(6) yes
C5 . C6 . C7 . 121.0(7) yes
C5 . C6 . H61 . 119.8 no
C7 . C6 . H61 . 119.2 no
C2 . C7 . C6 . 119.7(6) yes
C2 . C7 . I9 . 124.6(5) yes
C6 . C7 . I9 . 115.4(5) yes
C5 . C10 . O11 . 122.1(6) yes
C5 . C10 . O12 . 112.8(7) yes
O11 . C10 . O12 . 125.0(7) yes
C10 . O12 . C13 . 113.9(6) yes
O12 . C13 . C14 . 107.3(6) yes
O12 . C13 . H131 . 110.0 no
C14 . C13 . H131 . 110.2 no
O12 . C13 . H132 . 110.1 no
C14 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 109.8 no
C13 . C14 . H142 . 108.6 no
C13 . C14 . H141 . 109.2 no
H142 . C14 . H141 . 109.8 no
C13 . C14 . H143 . 108.8 no
H142 . C14 . H143 . 110.0 no
H141 . C14 . H143 . 110.5 no
N1 . N21 . C22 . 112.9(6) yes
N21 . C22 . C23 . 118.5(6) yes
N21 . C22 . C27 . 123.3(6) yes
C23 . C22 . C27 . 117.9(6) yes
C22 . C23 . C24 . 121.2(6) yes
C22 . C23 . I28 . 121.1(5) yes
C24 . C23 . I28 . 117.7(5) yes
C23 . C24 . C25 . 120.5(6) yes
C23 . C24 . H241 . 119.6 no
C25 . C24 . H241 . 120.0 no
C24 . C25 . C26 . 119.9(6) yes
C24 . C25 . C30 . 118.9(6) yes
C26 . C25 . C30 . 121.2(6) yes
C25 . C26 . C27 . 119.2(6) yes
C25 . C26 . H261 . 120.5 no
C27 . C26 . H261 . 120.4 no
C22 . C27 . C26 . 121.3(6) yes
C22 . C27 . I29 . 123.1(5) yes
C26 . C27 . I29 . 115.5(5) yes
C25 . C30 . O31 . 122.3(7) yes
C25 . C30 . O32 . 112.4(6) yes
O31 . C30 . O32 . 125.3(7) yes
C30 . O32 . C33 . 116.4(6) yes
O32 . C33 . C34 . 106.6(6) yes
O32 . C33 . H331 . 110.1 no
C34 . C33 . H331 . 110.5 no
O32 . C33 . H332 . 109.6 no
C34 . C33 . H332 . 110.1 no
H331 . C33 . H332 . 110.0 no
C33 . C34 . H342 . 109.0 no
C33 . C34 . H341 . 109.7 no
H342 . C34 . H341 . 109.5 no
C33 . C34 . H343 . 109.1 no
H342 . C34 . H343 . 110.2 no
H341 . C34 . H343 . 109.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.435(9) yes
N1 . N21 . 1.249(9) yes
C2 . C3 . 1.412(9) yes
C2 . C7 . 1.403(10) yes
C3 . C4 . 1.382(10) yes
C3 . I8 . 2.079(8) yes
C4 . C5 . 1.394(10) yes
C4 . H41 . 0.934 no
C5 . C6 . 1.398(9) yes
C5 . C10 . 1.505(10) yes
C6 . C7 . 1.383(10) yes
C6 . H61 . 0.922 no
C7 . I9 . 2.103(7) yes
C10 . O11 . 1.200(11) yes
C10 . O12 . 1.330(9) yes
O12 . C13 . 1.472(9) yes
C13 . C14 . 1.502(10) yes
C13 . H131 . 0.968 no
C13 . H132 . 0.969 no
C14 . H142 . 0.957 no
C14 . H141 . 0.960 no
C14 . H143 . 0.961 no
N21 . C22 . 1.433(9) yes
C22 . C23 . 1.414(9) yes
C22 . C27 . 1.407(9) yes
C23 . C24 . 1.369(10) yes
C23 . I28 . 2.085(6) yes
C24 . C25 . 1.400(9) yes
C24 . H241 . 0.933 no
C25 . C26 . 1.405(10) yes
C25 . C30 . 1.502(10) yes
C26 . C27 . 1.394(10) yes
C26 . H261 . 0.931 no
C27 . I29 . 2.100(6) yes
C30 . O31 . 1.215(10) yes
C30 . O32 . 1.321(9) yes
O32 . C33 . 1.455(9) yes
C33 . C34 . 1.515(10) yes
C33 . H331 . 0.967 no
C33 . H332 . 0.965 no
C34 . H342 . 0.962 no
C34 . H341 . 0.962 no
C34 . H343 . 0.964 no
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 1 1 x .
