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_1554828
_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         'C17 H15 N3 O2, 0.5(H2 O)'
_chemical_formula_sum            'C17 H16 N3 O2.5'
_chemical_formula_weight         302.33
_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
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 93.034(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6680(14)
_cell_length_b                   24.498(4)
_cell_length_c                   11.286(3)
_cell_measurement_reflns_used    609
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.1960
_cell_measurement_theta_min      1.9060
_cell_volume                     2945.4(10)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_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 10.3456
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
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  1 omega  -21.00   90.00   1.0000  350.0000
omega____ theta____ kappa____ phi______ frames
    -       15.5804   57.0000   90.0000 111

  2 omega  -92.00  -36.00   1.0000  350.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4398 -178.0000 -150.0000 56

  3 omega -110.00  -87.00   1.0000  350.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4398 -178.0000   90.0000 23
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_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0139620000
_diffrn_orient_matrix_UB_12      -0.0282062000
_diffrn_orient_matrix_UB_13      -0.0047790000
_diffrn_orient_matrix_UB_21      0.0116260000
_diffrn_orient_matrix_UB_22      -0.0014519000
_diffrn_orient_matrix_UB_23      0.0623536000
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_diffrn_orient_matrix_UB_32      -0.0064276000
_diffrn_orient_matrix_UB_33      0.0067552000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1393
_diffrn_reflns_av_unetI/netI     0.3222
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10639
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.912
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_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    1.364
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.0827
_exptl_crystal_size_mid          0.0632
_exptl_crystal_size_min          0.0486
_refine_diff_density_max         0.302
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_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.799
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.799
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                1841
_reflns_number_total             5183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00294d17.cif
_cod_data_source_block           mjp_test
_cod_original_cell_volume        2945.4(9)
_cod_original_formula_sum        'C17 H16 N3 O2.50'
_cod_database_code               1554828
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C16 H16 N2 O2'
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.49
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H006(0.02) H008(0.023) H009(0.025) H00I(0.022) H00N(0.018)
 H00S(0.017) H00V(0.021) H00A(0.027) H00C(0.027) H00D(0.027) H00X(0.02)
 H00Y(0.024) H00Z(0.027) H010(0.022) H012(0.025) H013(0.027) H014(0.021)
 H015(0.026) H016(0.029) H01A(0.044) H01B(0.044) H01C(0.044) H01D(0.045)
 H01E(0.045) H01F(0.045) H01G(0.049) H01H(0.049) H01I(0.049)
 Fixed X: H006(0.516071) H008(0.569826) H009(0.610765) H00I(0.119695)
 H00N(0.332659) H00S(0.279927) H00V(0.728757) H00A(0.192705) H00C(0.066219)
 H00D(0.136162) H00X(0.653531) H00Y(0.477531) H00Z(0.829238) H010(0.122587)
 H012(0.826533) H013(0.686622) H014(-0.051947) H015(0.863866) H016(0.292836)
 H01A(-0.143165) H01B(-0.165074) H01C(-0.091716) H01D(0.173141) H01E(0.156588)
 H01F(0.287548) H01G(0.027309) H01H(0.081735) H01I(0.122673)
 Fixed Y: H006(0.414926) H008(0.603378) H009(0.176541) H00I(0.507328)
 H00N(0.65618) H00S(0.078546) H00V(0.54486) H00A(-0.003349) H00C(-0.017579)
 H00D(0.037038) H00X(0.255404) H00Y(0.684725) H00Z(0.199817) H010(0.262192)
 H012(0.482171) H013(0.402043) H014(0.094927) H015(0.248986) H016(0.32921)
 H01A(0.179464) H01B(0.154434) H01C(0.121112) H01D(0.340614) H01E(0.329826)
 H01F(0.34773) H01G(0.587513) H01H(0.64592) H01I(0.596655)
 Fixed Z: H006(0.115788) H008(0.168494) H009(0.698193) H00I(0.621712)
 H00N(0.397739) H00S(0.655047) H00V(0.161848) H00A(0.694347) H00C(0.751937)
 H00D(0.785114) H00X(0.400388) H00Y(0.245334) H00Z(0.700343) H010(0.28503)
 H012(0.01726) H013(-0.013468) H014(0.468794) H015(0.514491) H016(0.2672)
 H01A(0.231761) H01B(0.356817) H01C(0.264218) H01D(0.523254) H01E(0.658445)
 H01F(0.614964) H01G(0.569585) H01H(0.596434) H01I(0.678266)
;
_shelx_res_checksum              37307
_shelx_hkl_checksum              93630
_olex2_submission_special_instructions 'No special instructions were received'