Synthesis and crystal structure of 2,9-diamino-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene
Valdez, Nichole; Nagel, Eric; Redline, Erica; Rodriguez, Mark; Staiger, Chad; Dugger, Jason; Foster, Jeffrey; Acta Crystallographica Section E Crystallographic Communications 80 (2024) –; doi:10.1107/S2056989024004468

data_2023137
_publ_section_title
;
 Synthesis and crystal structure of
 2,9-diamino-5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene
;
_journal_coeditor_code           VM2301
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024004468
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C16 H18 N2'
_chemical_formula_moiety         'C16 H18 N2'
_chemical_formula_sum            'C16 H18 N2'
_chemical_formula_weight         238.32
_chemical_name_systematic
;
2,9-Diamino-5,6,11,12-tetrahydrodibenzo[a,e][8]annulene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     shelXT
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8641(3)
_cell_length_b                   22.0075(6)
_cell_length_c                   6.2771(2)
_cell_measurement_reflns_used    8510
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      73.601
_cell_measurement_theta_min      4.018
_cell_volume                     1224.52(7)
_computing_cell_refinement
;
SAINT V8.40A (Bruker, 2019)
;
_computing_data_collection
;
APEX2 (Bruker, 2019)
;
_computing_data_reduction
;
SAINT V8.40A (Bruker, 2019)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL  (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i>  (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            39813
_diffrn_reflns_theta_full        65.014
_diffrn_reflns_theta_max         65.014
_diffrn_reflns_theta_min         4.017
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.223
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     172
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0353P)^2^+0.9951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                1781
_reflns_number_total             2060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vm2301.cif
_cod_data_source_block           I
_cod_database_code               2023137
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.994
_shelx_hkl_checksum              43946
_shelx_res_checksum              8739