Naphtho[2,1- e]-1,2-azaphosphorine 2-Oxide Derivatives: Synthesis, Optoelectronic Properties, and Self-Dimerization Phenomena.
Deng, Chun-Lin; Bard, Jeremy P.; Zakharov, Lev N.; Johnson, Darren W.; Haley, Michael M.; The Journal of organic chemistry 84 (2019) 8131–8139; doi:10.1021/acs.joc.9b00994

data_4034646
_publ_section_title
;
 Naphtho[2,1- e]-1,2-azaphosphorine 2-Oxide Derivatives: Synthesis,
 Optoelectronic Properties, and Self-Dimerization Phenomena.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8131
_journal_page_last               8139
_journal_paper_doi               10.1021/acs.joc.9b00994
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C26 H18 Cl3 N2 O2 P'
_chemical_formula_weight         527.74
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                117.135(3)
_cell_angle_beta                 106.977(3)
_cell_angle_gamma                94.402(4)
_cell_formula_units_Z            4
_cell_length_a                   12.7196(6)
_cell_length_b                   14.8501(7)
_cell_length_c                   15.4304(7)
_cell_measurement_reflns_used    5629
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.35
_cell_measurement_theta_min      3.45
_cell_volume                     2404.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30824
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.722
_diffrn_reflns_theta_max         66.722
_diffrn_reflns_theta_min         3.450
_diffrn_source                   'Incoatec I\mS'
_exptl_absorpt_coefficient_mu    4.310
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       cut-block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_platon_squeeze_details
;
Solvent molecules CHCl3 fill a space between main 
molecules and its positions are partially occupied.
These solvents molecules were treated by SQUEEZE. 
;
_refine_diff_density_max         1.335
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8446
_refine_ls_number_restraints     500
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.1027
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2856
_refine_ls_wR_factor_ref         0.3052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5721
_reflns_number_total             8446
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00994_si_002.cif
_cod_data_source_block           cu_mh217_0m_a_sqd
_cod_database_code               4034646
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.604
_shelx_estimated_absorpt_t_max   0.846
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              17973
_shelx_hkl_checksum              54882