Dibenzoylbenzodipyrroles: Key Precursors for the Synthesis of Fused Meso-Aryl Sapphyrins.
Isar, Prosenjit; Ravikanth, Mangalampalli; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00663

data_4038414
_publ_section_title
;
 Dibenzoylbenzodipyrroles: Key Precursors for the Synthesis of Fused
 Meso-Aryl Sapphyrins.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00663
_journal_year                    2020
_chemical_formula_moiety         '0.5(C38 H28 N2 O2), 0.5(C38 H29 N2 O2)'
_chemical_formula_sum            'C38 H28 N2 O2'
_chemical_formula_weight         544.62
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-13
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.618(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3713(14)
_cell_length_b                   30.827(3)
_cell_length_c                   15.0142(13)
_cell_measurement_reflns_used    3539
_cell_measurement_temperature    150
_cell_measurement_theta_max      21.9760
_cell_measurement_theta_min      1.9050
_cell_volume                     5698.5(10)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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   -110.00  19.00   1.00   12.00    --  -20.00 -72.00 -36.00  129
  2  \w    -95.00  19.00   1.00   12.00    --  -20.00 -72.00-180.00  114
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0321329000
_diffrn_orient_matrix_UB_12      -0.0059834000
_diffrn_orient_matrix_UB_13      0.0346388000
_diffrn_orient_matrix_UB_21      -0.0142158000
_diffrn_orient_matrix_UB_22      0.0220600000
_diffrn_orient_matrix_UB_23      0.0056040000
_diffrn_orient_matrix_UB_31      -0.0456399000
_diffrn_orient_matrix_UB_32      -0.0026089000
_diffrn_orient_matrix_UB_33      -0.0319943000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1796
_diffrn_reflns_av_unetI/netI     0.2664
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26041
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.117
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     761
_refine_ls_number_reflns         9997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.2673
_refine_ls_R_factor_gt           0.0982
_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^)+(0.0800P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.2939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3228
_reflns_number_total             9997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00663_si_002.cif
_cod_data_source_block           mr-pi-bpy-g-1_mo
_cod_original_cell_volume        5698.4(10)
_cod_database_code               4038414
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H28N2O2
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 90.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.05
_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.a Riding coordinates:
 N006(H006)
2.b Secondary CH2 refined with riding coordinates:
 C016(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 N005(H005), N007(H007), N008(H008), C00N(H00N), C00O(H00O), C00R(H00R),
 C00S(H00S), C00V(H00V), C00X(H00X), C010(H010), C011(H011), C012(H012),
 C014(H014), C015(H015), C017(H017), C018(H018), C019(H019), C01B(H01C),
 C01C(H01D), C01D(H01E), C01J(H01J), C01K(H01K), C01M(H01M), C01N(H01N),
 C01O(H01O), C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T),
 C01U(H01U), C01V(H01V), C01W(H01W), C01Z(H01Z), C021(H021), C022(H022),
 C023(H023), C024(H024), C025(H025), C026(H026), C027(H027), C028(H028)
2.d Idealised Me refined as rotating group:
 C029(H02G,H02H,H02I), C02A(H02A,H02B,H02C), C02B(H02J,H02K,H02L), C02C(H02D,
 H02E,H02F)
;
_shelx_res_checksum              595
_shelx_hkl_checksum              21833
_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 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.779