Non-planar porphyrins with mixed substituent pattern: bromination and formylation of ethyl-substituted tetraphenylporphyrins and tetraalkylporphyrins
Senge, Mathias O.; Gerstung, Vanessa; Ruhlandt-Senge, Karin; Runge, Steffen; Lehmann, Ingo; Journal of the Chemical Society, Dalton Transactions  (1998) 4187–; doi:10.1039/a806460a

data_7027065
_publ_section_title
;
 Non-planar porphyrins with mixed substituent pattern: bromination and
 formylation of ethyl-substituted tetraphenylporphyrins and
 tetraalkylporphyrins
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              4187
_journal_paper_doi               10.1039/a806460a
_journal_year                    1998
_chemical_formula_moiety         'C48 H36 Br2 N4'
_chemical_formula_sum            'C48 H36 Br2 N4'
_chemical_formula_weight         828.63
_chemical_name_systematic
; 
 2,13-Dibromo-7,8-diethyl-5,10,15,20-tetra- 
 phenylporphyrin (monoclinic modification)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.19
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8426(2)
_cell_length_b                   14.1555(3)
_cell_length_c                   22.6044(4)
_cell_measurement_reflns_used
;
 6744 reflections with I > 10 sigma I
;
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      n/a
_cell_measurement_theta_min      n/a
_cell_volume                     3717.32(12)
_computing_cell_refinement       SMART
_computing_data_collection
; 
 SMART, Software Reference Manual (1994). Siemens Anal.
 Instr. WI
;
_computing_data_reduction
;
 SAINT Version 4, Software Reference Manual (1995). Siemens
 Analystical Instr. WI
;
_computing_molecular_graphics    'XP, Shelxtl-Plus, Siemens, 1994'
_computing_publication_material  'XCIF, Shelxtl-Plus, Siemens, 1994'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.907
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22596
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        stable
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    2.222
_exptl_absorpt_correction_T_max  0.6176
_exptl_absorpt_correction_T_min  0.3911
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_refine_diff_density_max         1.438
_refine_diff_density_min         -0.976
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       n/d
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.1430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1242
_reflns_number_gt                6693
_reflns_number_total             8740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            806460asup1.cif
_cod_data_source_block           ms360
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/d' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.1430P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.1430P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3717.33(12)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7027065