A controlled blue-shift in meso-nitrogen aryl fused DIPY and BODIPY skeletons
Farinone, Marco; Cybińska, Joanna; Pawlicki, Miłosz; Organic Chemistry Frontiers 6 (2019) 2825–; doi:10.1039/C9QO00294D

data_1554825
_publ_section_title
;
 A controlled blue-shift in meso-nitrogen aryl fused DIPY and BODIPY
 skeletons
;
_journal_issue                   16
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2825
_journal_paper_doi               10.1039/C9QO00294D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                62.292(14)
_cell_angle_beta                 80.059(11)
_cell_angle_gamma                76.727(11)
_cell_formula_units_Z            2
_cell_length_a                   5.4882(7)
_cell_length_b                   11.1825(15)
_cell_length_c                   11.6413(16)
_cell_measurement_reflns_used    833
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.1420
_cell_measurement_theta_min      4.3023
_cell_volume                     613.82(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      293(2)
_diffrn_detector_area_resol_mean 8.1956
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
  1 omega -105.00  -21.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.7393  -37.0000 -180.0000 84

  2 omega  -71.00   27.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.7393   37.0000    0.0000 98

  3 omega    5.00   97.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7393 -125.0000 -180.0000 92

  4 omega   87.00  119.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       42.7393  125.0000 -180.0000 32

  5 omega -109.00  -83.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      -93.0000  125.0000 -120.0000 26

  6 omega   96.00  171.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513   45.0000   90.0000 75

  7 omega   44.00   77.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  150.0000 33

  8 omega   64.00  148.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513   15.0000   30.0000 84

  9 omega   43.00   70.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  -30.0000 27

 10 omega   35.00  143.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -77.0000  -60.0000 108

 11 omega   37.00   75.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  120.0000 38

 12 omega   76.00  138.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000    0.0000 62

 13 omega  147.00  176.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000    0.0000 29

 14 omega   42.00   68.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513 -137.0000 -165.0000 26

 15 omega   45.00   70.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000  -60.0000 25

 16 omega   38.00   77.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000   60.0000 39

 17 omega   90.00  116.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000 -150.0000 26

 18 omega  148.00  177.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  125.0000 -150.0000 29

 19 omega   37.00   62.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -      111.1513  -45.0000 -150.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0782583000
_diffrn_orient_matrix_UB_12      -0.1475274000
_diffrn_orient_matrix_UB_13      0.1043833000
_diffrn_orient_matrix_UB_21      0.1124481000
_diffrn_orient_matrix_UB_22      -0.0447315000
_diffrn_orient_matrix_UB_23      -0.1075767000
_diffrn_orient_matrix_UB_31      0.2547556000
_diffrn_orient_matrix_UB_32      0.0343570000
_diffrn_orient_matrix_UB_33      0.0024017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3681
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.939
_diffrn_reflns_theta_min         4.302
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_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    1.273
_exptl_crystal_description       irregular
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.2778
_exptl_crystal_size_mid          0.1528
_exptl_crystal_size_min          0.0855
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0956
_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^)+(0.1636P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2368
_refine_ls_wR_factor_ref         0.2677
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1644
_reflns_number_total             2349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00294d17.cif
_cod_data_source_block           mjp_1
_cod_database_code               1554825
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C15 H12 N3'
_reflns_odcompleteness_completeness 96.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H001(0.039) H003(0.045) H007(0.042) H008(0.039) H009(0.04)
 H00A(0.04) H00B(0.042) H00C(0.045) H00D(0.047) H00E(0.045) H00G(0.046)
 H00H(0.043) H00I(0.048)
 Fixed X: H001(1.032603) H003(0.428675) H007(0.818204) H008(0.776617)
 H009(1.145227) H00A(0.431004) H00B(1.196104) H00C(0.469315) H00D(0.335039)
 H00E(0.640448) H00G(0.247112) H00H(1.046224) H00I(1.065088)
 Fixed Y: H001(0.353793) H003(0.219224) H007(0.076273) H008(0.442068)
 H009(0.597311) H00A(0.648091) H00B(0.13653) H00C(0.338076) H00D(0.842314)
 H00E(0.91631) H00G(0.20364) H00H(0.79046) H00I(-0.041705)
 Fixed Z: H001(0.586699) H003(0.452648) H007(0.528152) H008(0.122538)
 H009(0.144797) H00A(0.291756) H00B(0.758197) H00C(0.076382) H00D(0.102509)
 H00E(-0.068395) H00G(0.284979) H00H(-0.0458) H00I(0.724903)
;
_shelx_res_checksum              82129
_shelx_hkl_checksum              3987
_olex2_submission_special_instructions 'No special instructions were received'