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_1554827
_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 H14 B F2 N3 O2, C2 H3 N'
_chemical_formula_sum            'C19 H17 B F2 N4 O2'
_chemical_formula_weight         382.17
_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             2019-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-12 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                93.791(5)
_cell_angle_beta                 100.927(5)
_cell_angle_gamma                98.538(5)
_cell_formula_units_Z            2
_cell_length_a                   7.1859(4)
_cell_length_b                   12.0427(7)
_cell_length_c                   12.0895(9)
_cell_measurement_reflns_used    1917
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.5860
_cell_measurement_theta_min      2.2710
_cell_volume                     1011.05(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3456
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.862
_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      1.00  94.00   1.00    7.50    --   15.81  77.00 -90.00   93
  2  \w     -7.00  97.00   1.00    7.50    --   15.81  77.00 150.00  104
  3  \w    -56.00  44.00   1.00    7.50    --  -16.75  77.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0050883000
_diffrn_orient_matrix_UB_12      -0.0579359000
_diffrn_orient_matrix_UB_13      0.0045796000
_diffrn_orient_matrix_UB_21      -0.1012144000
_diffrn_orient_matrix_UB_22      -0.0135059000
_diffrn_orient_matrix_UB_23      -0.0180686000
_diffrn_orient_matrix_UB_31      0.0107902000
_diffrn_orient_matrix_UB_32      -0.0064846000
_diffrn_orient_matrix_UB_33      -0.0570708000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6891
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.762
_diffrn_reflns_theta_min         1.718
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.255
_exptl_crystal_description       irregular
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0600P)^2^+0.1304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3331
_reflns_number_total             4547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00294d17.cif
_cod_data_source_block           mf006
_cod_database_code               1554827
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H005(0.018) H00G(0.02) H00I(0.022) H00K(0.023) H00L(0.023)
 H00M(0.024) H00N(0.025) H00P(0.029) H00A(0.033) H00B(0.033) H00C(0.033)
 H00D(0.04) H00E(0.04) H00F(0.04) H00H(0.078) H00J(0.078) H00O(0.078)
 Fixed X: H005(0.297272) H00G(0.219505) H00I(0.282855) H00K(0.12532)
 H00L(0.346411) H00M(0.367631) H00N(0.458106) H00P(0.44936) H00A(0.060139)
 H00B(0.27346) H00C(0.108082) H00D(0.130806) H00E(0.007771) H00F(0.221522)
 H00H(0.092691) H00J(0.305871) H00O(0.252564)
 Fixed Y: H005(0.67549) H00G(0.571343) H00I(0.280342) H00K(0.231761)
 H00L(0.405719) H00M(0.873306) H00N(0.888587) H00P(1.005015) H00A(0.533312)
 H00B(0.519202) H00C(0.45959) H00D(0.050216) H00E(0.105119) H00F(0.09499)
 H00H(0.835505) H00J(0.895602) H00O(0.764978)
 Fixed Z: H005(0.524767) H00G(0.671214) H00I(0.227543) H00K(0.616665)
 H00L(0.08106) H00M(0.4603) H00N(0.144014) H00P(0.317573) H00A(0.810552)
 H00B(0.856998) H00C(0.911042) H00D(0.385991) H00E(0.461728) H00F(0.512324)
 H00H(0.859722) H00J(0.902204) H00O(0.905425)
;
_shelx_res_checksum              64228
_shelx_hkl_checksum              34121
_shelx_fab_checksum              4380
_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 1.053
_oxdiff_exptl_absorpt_empirical_full_min 0.966