Structure–property investigations in urea tethered iodinated triphenylamines
Hossain, Muhammad Saddam; Ahmed, Fiaz; Karakalos, Stavros G.; Smith, Mark D.; Pant, Namrata; Garashchuk, Sophya; Greytak, Andrew B.; Docampo, Pablo; Shimizu, Linda S.; Physical Chemistry Chemical Physics  (2022) –; doi:10.1039/D2CP01856J

data_7245228
_publ_section_title
;
 Structure--property investigations in urea tethered iodinated
 triphenylamines
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D2CP01856J
_journal_year                    2022
_chemical_formula_moiety         'C39 H30 I4 N4 O, 0.72(C4 H8 O2)'
_chemical_formula_sum            'C41.89 H35.78 I4 N4 O2.45'
_chemical_formula_weight         1141.92
_chemical_properties_physical    Light-sensitive
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-04-11 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.092(2)
_cell_angle_beta                 100.214(2)
_cell_angle_gamma                114.586(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5202(4)
_cell_length_b                   10.0356(4)
_cell_length_c                   23.9703(9)
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.360
_cell_measurement_theta_min      2.309
_cell_volume                     2033.89(15)
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            46016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.399
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         2.249
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.106
_exptl_absorpt_correction_T_max  0.6465
_exptl_absorpt_correction_T_min  0.5171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.7998.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_description       needle
_exptl_crystal_F_000             1093
_exptl_crystal_preparation       'Conductive, Persistent radical'
_exptl_crystal_recrystallization_method 'Slow Evaporation'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.00083(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         8313
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0362
_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/[\s^2^(Fo^2^)+9.7083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7239
_reflns_number_total             8313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cp01856j2.cif
_cod_data_source_block           tpa_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        2033.89(14)
_cod_database_code               7245228
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.418
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C21 = O1-C1
 1.2 with sigma of 0.01
 O71-C72 = O51-C52 = O61-C62
 1.21 with sigma of 0.015
 C72-C71 = C52-C51 = C62-C61
 1.478 with sigma of 0.015
 O72-C72 = O62-C62 = O52-C52
 1.324 with sigma of 0.015
 O62-C63 = O52-C53 = O72-C73
 1.456 with sigma of 0.015
 C54-C53 = C74-C73 = C64-C63
 1.456 with sigma of 0.015
 O71-C71 = C51-O51 = C61-O61
 2.39 with sigma of 0.02
 O72-C71 = C51-O52 = C61-O62
 2.33 with sigma of 0.02
 O72-C74 = O52-C54 = O62-C64
 2.37 with sigma of 0.02
 N4-C21 \\sim N5-C21 \\sim N1-C1 \\sim N2-C1
 with sigma of 0.01
 N4_$1-C22 \\sim N5-C22 \\sim N1_$2-C2 \\sim N2-C2
 with sigma of 0.01
 N5-C21 \\sim N4-C21 \\sim N2-C1 \\sim N1-C1
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Sof(O51)=Sof(O52)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52)=Sof(C53)=
 Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(1)
 Sof(O61)=Sof(O62)=Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(H61C)=Sof(C62)=Sof(C63)=
 Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(2)
 Sof(O71)=Sof(O72)=Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(H71C)=Sof(C72)=Sof(C73)=
 Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(3)
 Uiso(O51)=Uiso(O52)=Uiso(C51)=Uiso(C52)=Uiso(C53)=Uiso(C54)=Uiso(O61)=
 Uiso(O62)=Uiso(C61)=Uiso(C62)=Uiso(C63)=Uiso(C64)=Uiso(O71)=Uiso(O72)=
 Uiso(C71)=Uiso(C72)=Uiso(C73)=Uiso(C74)=FVAR(4)
 Fixed Sof: O1(0.5) N1(0.5) H1(0.5) N2(0.5) H2(0.5) C1(0.5) H2AA(0.5)
 H2AB(0.5) H2BC(0.5) H2BD(0.5) O2(0.5) N4(0.5) H4A(0.5) N5(0.5) H5A(0.5)
 C21(0.5) H22A(0.5) H22B(0.5) H22C(0.5) H22D(0.5)
5.a Riding coordinates:
 N1(H1), N2(H2), C2(H2AA,H2AB), C2(H2BC,H2BD), N4(H4A), N5(H5A), C22(H22A,
 H22B), C22(H22C,H22D)
5.b Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B), C63(H63A,H63B), C73(H73A,H73B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C24(H24), C25(H25), C27(H27), C28(H28),
  C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40)
5.d Idealised Me refined with riding coordinates:
 C51(H51A,H51B,H51C), C54(H54A,H54B,H54C), C61(H61A,H61B,H61C), C64(H64A,H64B,
 H64C), C71(H71A,H71B,H71C), C74(H74A,H74B,H74C)
;
_shelx_res_checksum              12078
_shelx_hkl_checksum              27662
_olex2_submission_special_instructions 'No special instructions were received'