Synthesis, crystallographic characterization and homogeneous catalytic activity of novel unsymmetric porphyrins
Antonangelo, A. R.; Westrup, K. C. M.; Burt, L. A.; Bezzu, C. Grazia; Malewschik, T.; Machado, G. S.; Nunes, F. S.; McKeown, N. B.; Nakagaki, S.; RSC Adv. 7 (2017) 50610–; doi:10.1039/C7RA08734A

data_7229459
_publ_section_title
;
 Synthesis, crystallographic characterization and homogeneous catalytic
 activity of novel unsymmetric porphyrins
;
_journal_issue                   80
_journal_name_full               'RSC Adv.'
_journal_page_first              50610
_journal_paper_doi               10.1039/C7RA08734A
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         '2(C H Cl3), C48 H28 F10 N4 O4'
_chemical_formula_sum            'C50 H30 Cl6 F10 N4 O4'
_chemical_formula_weight         1153.48
_chemical_name_systematic
'trans-5,15-bis(pentafluorophenyl)-10,20-bis(3,4-dimethoxyphenyl)porphyrin (P1)'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-03-07 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.177(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.948(3)
_cell_length_b                   15.6771(17)
_cell_length_c                   11.2006(16)
_cell_measurement_reflns_used    1482
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.1630
_cell_measurement_theta_min      1.9540
_cell_volume                     2313.3(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 0.172
_diffrn_detector_dtime           '0.004 (microseconds)'
_diffrn_detector_type            'Dectris Pilatus M2'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      'shutterless data collection'
_diffrn_measurement_device       i19-FFD-air
_diffrn_measurement_device_details 'custom build fixed Chi diffractometer'
_diffrn_measurement_device_type  'i19-FFD-air (fixed Chi) Pilatus M2'
_diffrn_measurement_method       'omega and phi rotation'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0455982000
_diffrn_orient_matrix_UB_12      -0.0214890000
_diffrn_orient_matrix_UB_13      0.0205219000
_diffrn_orient_matrix_UB_21      -0.0257510000
_diffrn_orient_matrix_UB_22      -0.0382360000
_diffrn_orient_matrix_UB_23      -0.0088606000
_diffrn_orient_matrix_UB_31      0.0007536000
_diffrn_orient_matrix_UB_32      -0.0016462000
_diffrn_orient_matrix_UB_33      -0.0611203000
_diffrn_radiation_collimation    '0.1 Pinhole'
_diffrn_radiation_monochromator  'double crystal Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8341
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        20.134
_diffrn_reflns_theta_max         20.134
_diffrn_reflns_theta_min         1.498
_diffrn_source                   'Diamond Light Source Beamline I19'
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       plate
_exptl_crystal_F_000             1164
_exptl_crystal_recrystallization_method
'Vapour diffussion of methanol into a chloroform solution'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.242
_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     336
_refine_ls_number_reflns         2340
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0725
_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^)+(0.1958P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1593
_reflns_number_total             2340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra08734a2.cif
_cod_data_source_block           P1
_cod_original_cell_volume        2313.2(7)
_cod_database_code               7229459
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 96.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     20.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 F1, F2, F3, F4, F5, O1, O2, N1, N2, C1, C2, C3, C4, C5, C6, C7, C8, C9, C11,
 C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Cl1, Cl2, Cl3, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C25(H25)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C12(H12), C15(H15), C17(H17), C18(H18), C20(H20)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_olex2_date_sample_completion    2016-02-24
_olex2_date_sample_data_collection 2016-02-24
_olex2_date_sample_submission    2016-02-24
_olex2_exptl_crystal_mounting_method Paratone
_olex2_submission_original_sample_id Ar2_2_0
_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 4.164
_oxdiff_exptl_absorpt_empirical_full_min 0.585