Synthesis of Heteroatom Substituted Naphthoporphyrazine Derivatives with Near-Infrared Absorption and Emission
Evan R. Trivedi; Sangwan Lee; Hong Zong; Carl M. Blumenfeld; Anthony G. M. Barrett; Brian M. Hoffman; Journal of Organic Chemistry 75 (2010) 1799–1802; doi:10.1021/jo9026947

data_4025280
_publ_section_title
;
 Synthesis of Heteroatom Substituted Naphthoporphyrazine Derivatives with
 Near-Infrared Absorption and Emission
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1799
_journal_page_last               1802
_journal_paper_doi               10.1021/jo9026947
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C72 H90 N8 O12 S4'
_chemical_formula_weight         1387.76
_chemical_name_systematic
; 
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.305(3)
_cell_angle_beta                 95.406(3)
_cell_angle_gamma                105.033(3)
_cell_formula_units_Z            2
_cell_length_a                   15.334(3)
_cell_length_b                   15.813(3)
_cell_length_c                   16.340(3)
_cell_measurement_reflns_used    7924
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.31
_cell_volume                     3513.7(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.884
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.1159
_diffrn_reflns_av_sigmaI/netI    0.1418
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31365
_diffrn_reflns_theta_full        28.85
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9303
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'face indexed'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.916
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     872
_refine_ls_number_reflns         16284
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.1585
_refine_ls_R_factor_gt           0.0866
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1349P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2163
_refine_ls_wR_factor_ref         0.2577
_reflns_number_gt                8108
_reflns_number_total             16284
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9026947_si_002.cif
_cod_data_source_block           s62vm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' 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 
;
_cod_original_cell_volume        3513.7(11)
_cod_database_code               4025280