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_1554829
_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 H16 B F2 N3 O2'
_chemical_formula_sum            'C17.14 H14.5 B F2 N3 O2'
_chemical_formula_weight         343.29
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-30
_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                90
_cell_angle_beta                 91.217(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1306(3)
_cell_length_b                   11.7622(3)
_cell_length_c                   24.0194(7)
_cell_measurement_reflns_used    8060
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8775
_cell_measurement_theta_min      3.0160
_cell_volume                     3143.92(15)
_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 8.3359
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details
;
  1 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000    0.0000 153

  2 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000   90.0000 153

  3 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000  180.0000 153

  4 omega  -54.00   60.75   0.7500   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.0000  -79.0000  270.0000 153
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0024937000
_diffrn_orient_matrix_UB_12      -0.0343354000
_diffrn_orient_matrix_UB_13      -0.0242852000
_diffrn_orient_matrix_UB_21      -0.0634537000
_diffrn_orient_matrix_UB_22      -0.0028337000
_diffrn_orient_matrix_UB_23      0.0017589000
_diffrn_orient_matrix_UB_31      -0.0054430000
_diffrn_orient_matrix_UB_32      0.0495313000
_diffrn_orient_matrix_UB_33      -0.0166961000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20535
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         3.016
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70772
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1419
_exptl_crystal_size_max          0.829
_exptl_crystal_size_mid          0.548
_exptl_crystal_size_min          0.366
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6900
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0599
_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^)+(0.0863P)^2^+1.5087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1730
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5157
_reflns_number_total             6900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00294d17.cif
_cod_data_source_block           mf004
_cod_original_formula_sum        'C17.14 H14.50 B F2 N3 O2'
_cod_database_code               1554829
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H007(0.027) H009(0.03) H00O(0.029) H00P(0.028) H00Q(0.031)
 H00R(0.032) H00S(0.029) H00U(0.032) H00V(0.03) H00W(0.033) H00X(0.03)
 H00Y(0.03) H00Z(0.035) H010(0.035) H012(0.037) H013(0.045) H014(0.041)
 H015(0.042) H01D(0.05) H01E(0.05) H01F(0.05) H017(0.047) H019(0.044)
 H01G(0.052) H01H(0.052) H01I(0.052) H01A(0.142) H01B(0.142) H01C(0.142)
 H00A(0.054) H00B(0.054) H00C(0.054) H0AA(0.052) H0AB(0.052) H0AC(0.052)
 Fixed X: H007(0.838323) H009(0.562977) H00O(0.588494) H00P(0.768367)
 H00Q(0.477443) H00R(0.528055) H00S(0.463786) H00U(0.436467) H00V(0.706881)
 H00W(0.732406) H00X(0.764435) H00Y(0.958662) H00Z(0.801515) H010(0.741593)
 H012(0.985278) H013(1.016083) H014(0.879472) H015(0.844897) H01D(0.412475)
 H01E(0.387913) H01F(0.52032) H017(1.068843) H019(0.815632) H01G(0.792292)
 H01H(0.659754) H01I(0.76709) H01A(0.679549) H01B(0.799196) H01C(0.674973)
 H00A(0.90203) H00B(1.03552) H00C(1.007683) H0AA(1.108557) H0AB(1.081408)
 H0AC(1.004974)
 Fixed Y: H007(0.460389) H009(0.580521) H00O(0.34223) H00P(0.358896)
 H00Q(0.649576) H00R(0.471951) H00S(0.340785) H00U(0.646751) H00V(0.577031)
 H00W(0.319801) H00X(0.328399) H00Y(0.458676) H00Z(0.487826) H010(0.713035)
 H012(0.759851) H013(0.877761) H014(0.171769) H015(0.695334) H01D(0.238935)
 H01E(0.120047) H01F(0.161794) H017(0.91768) H019(0.161551) H01G(0.51775)
 H01H(0.474333) H01I(0.396068) H01A(0.81506) H01B(0.879168) H01C(0.936989)
 H00A(0.531812) H00B(0.489834) H00C(0.617236) H0AA(0.455558) H0AB(0.431623)
 H0AC(0.371835)
 Fixed Z: H007(0.401693) H009(0.180228) H00O(-0.021109) H00P(0.471267)
 H00Q(0.261532) H00R(0.402533) H00S(0.135687) H00U(0.362969) H00V(0.090734)
 H00W(0.571946) H00X(0.146525) H00Y(0.313387) H00Z(0.625142) H010(0.362698)
 H012(0.384106) H013(0.54001) H014(0.192718) H015(0.202415) H01D(-0.035645)
 H01E(-0.008668) H01F(-0.016242) H017(0.442842) H019(0.290248) H01G(-0.085213)
 H01H(-0.080416) H01I(-0.061527) H01A(0.191734) H01B(0.207107) H01C(0.217961)
 H00A(0.144082) H00B(0.141885) H00C(0.155795) H0AA(0.240676) H0AB(0.177447)
 H0AC(0.223048)
;
_shelx_res_checksum              97414
_shelx_hkl_checksum              25489
_olex2_submission_special_instructions 'No special instructions were received'