A rapid, metal-free synthesis of amino- and hydroxyphenanthrenes with tunable photophysical properties.
Ozomarisi, Hamza Enesi; Outlaw, Victor K.; RSC advances 15 (2025) 38024–38028; doi:10.1039/d5ra06485f

data_7251037
_publ_section_title
;
 A rapid, metal-free synthesis of amino- and hydroxyphenanthrenes with
 tunable photophysical properties.
;
_journal_issue                   45
_journal_name_full               'RSC advances'
_journal_page_first              38024
_journal_page_last               38028
_journal_paper_doi               10.1039/d5ra06485f
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C15 H10 N2'
_chemical_formula_sum            'C15 H10 N2'
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_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-09-18 deposited with the CCDC.	2025-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                99.9568(12)
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_cell_angle_gamma                116.6025(12)
_cell_formula_units_Z            2
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_cell_length_b                   8.4139(2)
_cell_length_c                   9.3777(3)
_cell_measurement_reflns_used    9373
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.33
_cell_volume                     531.76(3)
_computing_cell_refinement       'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_computing_data_collection       'Bruker Apex4 V.2022.1-1'
_computing_data_reduction        'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture P2'
_diffrn_measurement_method       'shutterless omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23305
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_min         2.909
_diffrn_source                   'Incoatec IMuS microfocus Mo tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.112(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0642P)^2^+0.1959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2160
_reflns_number_total             2637
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra06485f2.cif
_cod_data_source_block           6d
_cod_database_code               7251037
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              79213