Stepwise fusion of porphyrin β,β'-pyrrolic positions to imidazole rings.
Lo, Mamadou; Lefebvre, Jean-François; Leclercq, Dominique; van der Lee, Arie; Richeter, Sébastien; Organic letters 13 (2011) 3110–3113; doi:10.1021/ol2010215

data_1502224
_publ_section_title
;
 Stepwise fusion of porphyrin \b,\b'-pyrrolic positions to imidazole
 rings.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3110
_journal_page_last               3113
_journal_paper_doi               10.1021/ol2010215
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C62 H62 N8 Ni, 3(C2 H F3 O2), 2(C2 F3 O2) '
_chemical_formula_sum            'C72 H65 F15 N8 Ni O10'
_chemical_formula_weight         1546.01
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                94.0274(17)
_cell_angle_beta                 108.2509(19)
_cell_angle_gamma                99.0435(17)
_cell_formula_units_Z            2
_cell_length_a                   12.1781(3)
_cell_length_b                   18.0930(4)
_cell_length_c                   18.6755(4)
_cell_measurement_reflns_used    16249
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.0229
_cell_measurement_theta_min      1.5204
_cell_volume                     3827.91(16)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.4205
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details
;
  1 omega   -2.00  100.00   1.0000   37.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2314   77.0000 -120.0000 102

  2 omega  -10.00  100.00   1.0000   37.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2314   77.0000    0.0000 110

  3 omega  -19.00   88.00   1.0000   37.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2314   77.0000  150.0000 107

  4 omega  -57.00   69.00   1.0000   37.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5126   77.0000 -120.0000 126

  5 omega  -61.00   49.00   1.0000   37.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5126   77.0000    0.0000 110

  6 omega  -61.00   50.00   1.0000   37.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5126   77.0000  120.0000 111

;
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0386057000
_diffrn_orient_matrix_UB_12      0.0349892000
_diffrn_orient_matrix_UB_13      0.0160256000
_diffrn_orient_matrix_UB_21      -0.0392554000
_diffrn_orient_matrix_UB_22      0.0097454000
_diffrn_orient_matrix_UB_23      0.0186498000
_diffrn_orient_matrix_UB_31      0.0294883000
_diffrn_orient_matrix_UB_32      -0.0168051000
_diffrn_orient_matrix_UB_33      0.0319506000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_sigmaI/netI    0.1194
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            48919
_diffrn_reflns_theta_full        26.127
_diffrn_reflns_theta_max         29.031
_diffrn_reflns_theta_min         2.892
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_platon_squeeze_details
;
possible solvants: pentane/chloroforme
;
_refine_diff_density_max         1.17
_refine_diff_density_min         -0.93
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9552
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     935
_refine_ls_number_reflns         12985
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.0003173
_refine_ls_shift/su_mean         0.0000129
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are:
 7.12 2.51 5.17 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1034
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0746
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              24
_reflns_limit_k_min              -24
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                12985
_reflns_number_total             17527
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.36
_oxford_diffrn_Wilson_scale      0.43
_oxford_refine_ls_r_factor_ref   0.0655
_oxford_refine_ls_scale          1.322(2)
_oxford_reflns_number_all        17525
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            ol2010215_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        3827.91(15)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               1502224
_montpellier_reflns_maxres       0.77
_montpellier_reflns_completeness_maxres 99.8
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE ,  NI(1,X'S,U'S) UNTIL O(107), 
CONT F(100,X'S,U[ISO],SIZE,DECLINATION,AZIMUTH) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 143,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S)
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) H   ( 303,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
RIDE C   (  32,X'S) H   ( 323,X'S) H   ( 322,X'S) H   ( 321,X'S)
RIDE N   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE N   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) H   ( 502,X'S) H   ( 503,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) H   ( 512,X'S) H   ( 513,X'S) 
RIDE C   (  52,X'S) H   ( 523,X'S) H   ( 522,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  58,X'S) H   ( 581,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) H   ( 642,X'S) H   ( 643,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) H   ( 652,X'S) H   ( 653,X'S) 
RIDE C   (  66,X'S) H   ( 663,X'S) H   ( 662,X'S) H   ( 661,X'S) 
RIDE N   (  69,X'S) H   ( 691,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE N   (  71,X'S) H   ( 711,X'S) 
RIDE O   (  92,X'S) H   ( 921,X'S) 
RIDE O   (  99,X'S) H   ( 991,X'S) 
RIDE O   ( 107,X'S) H   (1071,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;