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_7232706
_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         'C45 H13 F20 N5 O4'
_chemical_formula_sum            'C45 H11 F20 N5 O4'
_chemical_formula_weight         1065.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-08-14 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.592(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.7880(5)
_cell_length_b                   16.3752(3)
_cell_length_c                   12.6133(2)
_cell_measurement_reflns_used    32345
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      30.2550
_cell_measurement_theta_min      3.5730
_cell_volume                     5326.11(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_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 (Sheldrick ,2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -22.00  88.00   0.50    8.00    --   -1.70  49.00 -91.84  220
  2  \w    -28.00  82.00   0.50    8.00    --   -1.70  71.00 122.84  220
  3  \w    -24.00   2.00   0.50    8.00    --   -1.70  57.00-180.00   52
  4  \w      6.00  88.00   0.50    8.00    --   -1.70  57.00-180.00  164
  5  \w    -24.00  84.00   0.50    8.00    --   -1.70  57.00   0.00  216
  6  \w    -24.00   3.00   0.50    8.00    --   -1.70  57.00-150.00   54
  7  \w     18.00  80.00   0.50    8.00    --   -1.70  57.00-150.00  124
  8  \w    -24.00  80.00   0.50    8.00    --   -1.70  57.00  60.00  208
  9  \w    -29.00  73.00   0.50    8.00    --   -1.70  72.00 -47.11  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0027706000
_diffrn_orient_matrix_UB_12      0.0001668000
_diffrn_orient_matrix_UB_13      0.0559987000
_diffrn_orient_matrix_UB_21      0.0273156000
_diffrn_orient_matrix_UB_22      0.0024765000
_diffrn_orient_matrix_UB_23      -0.0050909000
_diffrn_orient_matrix_UB_31      -0.0015964000
_diffrn_orient_matrix_UB_32      0.0432593000
_diffrn_orient_matrix_UB_33      0.0000792000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            78894
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         3.534
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'reddish violet'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.148
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         7075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0690
_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^)+(0.0936P)^2^+14.3766P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.1948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6205
_reflns_number_total             7075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cp01177c2.cif
_cod_data_source_block           c2m_sq_s
_cod_database_code               7232706
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C59 H45 Cl4 F20 N5 O4'
_reflns_odcompleteness_completeness 99.72
_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. Shared sites
{O1A, C5B}
{O1B, C5A}
3. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(C5B)
Uanis(O1B) = Uanis(C5A)
4. Others
 Sof(O1B)=Sof(C5B)=Sof(O2B)=1-FVAR(1)
 Sof(C5A)=Sof(O1A)=Sof(O2A)=FVAR(1)
 Fixed Sof: H11A(0.5) H11B(0.5) H11C(0.5)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.c Me refined with riding coordinates:
 C11(H11A,H11B,H11C)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C1(H1A)
;
_shelx_res_checksum              55049
_shelx_fab_checksum              99151
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.878