Aromaticity versus Regioisomeric Effect of β-Substituents in Porphyrinoids
Yao, Yuhang; Rao, Yu; Liu, Yi-Wei; Jiang, Liang; Xiong, Jin; Fan, Ying-Jie; Shen, Zhen; Sessler, Jonathan L.; Zhang, Jun-Long; Physical Chemistry Chemical Physics  (2019) –; doi:10.1039/C9CP01177C

data_7232701
_publ_section_title
;
 Aromaticity versus Regioisomeric Effect of \b-Substituents in
 Porphyrinoids
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/C9CP01177C
_journal_year                    2019
_chemical_formula_moiety         'C H Cl3, C45 H13 F20 N5 O4, 0.25(C12 H28)'
_chemical_formula_sum            'C49 H21 Cl3 F20 N5 O4'
_chemical_formula_weight         1230.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_symmetry_space_group_name_Hall  '-I 2y'
_symmetry_space_group_name_H-M   'I 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-08-14 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.048(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9313(9)
_cell_length_b                   16.3839(12)
_cell_length_c                   17.3825(10)
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.1580
_cell_measurement_theta_min      3.4290
_cell_volume                     5390.6(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3914
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -5.00   89.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       13.4628   77.0000 -120.0000 94

  2 omega  -11.00   83.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       13.4628   57.0000  150.0000 94

  3 omega   -9.00   84.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       13.4628   42.0000   46.6826 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0143540000
_diffrn_orient_matrix_UB_12      -0.0058769000
_diffrn_orient_matrix_UB_13      0.0375721000
_diffrn_orient_matrix_UB_21      0.0183793000
_diffrn_orient_matrix_UB_22      0.0375911000
_diffrn_orient_matrix_UB_23      -0.0027579000
_diffrn_orient_matrix_UB_31      -0.0293189000
_diffrn_orient_matrix_UB_32      0.0206876000
_diffrn_orient_matrix_UB_33      0.0156886000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19233
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.847
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       block
_exptl_crystal_F_000             2452
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.647
_refine_diff_density_min         -1.297
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         6392
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0954
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1358P)^2^+18.9961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2623
_refine_ls_wR_factor_ref         0.2963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4035
_reflns_number_total             6392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cp01177c2.cif
_cod_data_source_block           170505_sq
_cod_database_code               7232701
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C45 H13 F20 N5 O4'
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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. Restrained distances
 C6-C2
 1.56 with sigma of 0.02
 C1-C6
 1.56 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl00) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(Cl1) \\sim Ueq, Uanis(Cl00) \\sim Ueq, Uanis(Cl00) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.005
Uanis(C017) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Others
 Fixed Sof: H00C(0.5) H00E(0.5) H00G(0.5) H1A(0.5) H1B(0.5) H1C(0.5) H2A(0.5)
 H2B(0.5) H6A(0.5) H6B(0.5)
5.a Ternary CH refined with riding coordinates:
 C00L(H00L), C017(H017)
5.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C2(H2A,H2B), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 N00D(H00D), N00F(H00F), C011(H011)
5.d Idealised Me refined as rotating group:
 C00V(H00C,H00E,H00G), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              65565
_shelx_fab_checksum              6559
_olex2_submission_special_instructions 'No special instructions were received'