Synthesis of Salts of 1,2,5,6- and 1,4,5,8-Naphthalenetetramine.
Langis-Barsetti, Sophie; Maris, Thierry; Wuest, James D.; ACS omega 2 (2017) 6023–6030; doi:10.1021/acsomega.7b01055

data_4516916
_publ_section_title
;
 Synthesis of Salts of 1,2,5,6- and 1,4,5,8-Naphthalenetetramine.
;
_journal_issue                   9
_journal_name_full               'ACS omega'
_journal_page_first              6023
_journal_page_last               6030
_journal_paper_doi               10.1021/acsomega.7b01055
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C26 H20 N4 O8'
_chemical_formula_sum            'C26 H20 N4 O8'
_chemical_formula_weight         516.46
_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
_audit_creation_date             2017-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.402(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   21.374(2)
_cell_length_b                   5.9585(5)
_cell_length_c                   10.0311(8)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.999
_cell_measurement_theta_min      4.141
_cell_volume                     1276.41(19)
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS, 2016)'
_computing_data_collection       'APEX2 (Bruker AXS, 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27338
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.662
_diffrn_reflns_theta_min         2.069
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1170 before and 0.0821 after correction. The Ratio of minimum to maximum transmission is 0.7517. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       lozenge
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.537
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.490
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.1112
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3257
_refine_ls_wR_factor_ref         0.3528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1850
_reflns_number_total             2425
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b01055_si_003.cif
_cod_data_source_block           jw1779
_cod_original_cell_volume        1276.44(19)
_cod_database_code               4516916
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.878
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C7A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim C13A \\sim C7B
\\sim C8B \\sim C9B \\sim C10B \\sim C11B \\sim C12B \\sim C13B \\sim C7C \\sim
C8C \\sim C9C \\sim C10C \\sim C11C \\sim C12C \\sim C13C \\sim C7D \\sim C8D
\\sim C9D \\sim C10D \\sim C11D \\sim C12D \\sim C13D: within 1A with sigma of
0.005 and sigma for terminal atoms of 0.005
Uanis(C7A) \\sim Ueq, Uanis(C8A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A)
\\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13A) \\sim Ueq,
Uanis(C7B) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C9B) \\sim Ueq, Uanis(C10B)
\\sim Ueq, Uanis(C11B) \\sim Ueq, Uanis(C12B) \\sim Ueq, Uanis(C13B) \\sim Ueq,
Uanis(C7C) \\sim Ueq, Uanis(C8C) \\sim Ueq, Uanis(C9C) \\sim Ueq, Uanis(C10C)
\\sim Ueq, Uanis(C11C) \\sim Ueq, Uanis(C12C) \\sim Ueq, Uanis(C13C) \\sim Ueq,
Uanis(C7D) \\sim Ueq, Uanis(C8D) \\sim Ueq, Uanis(C9D) \\sim Ueq, Uanis(C10D)
\\sim Ueq, Uanis(C11D) \\sim Ueq, Uanis(C12D) \\sim Ueq, Uanis(C13D) \\sim Ueq:
with sigma of 0.02 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C7A, C8A, C9A, C10A, C11A, C12A, C13A, C7B, C8B, C9B, C10B, C11B, C12B, C13B,
 C7C, C8C, C9C, C10C, C11C, C12C, C13C, C7D, C8D, C9D, C10D, C11D, C12D, C13D
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Same fragment restrains
{C7A, C8A, C9A, C10A, C11A, C12A, C13A} sigma for 1-2: 0.01, 1-3: 0.04
as
{C7B, C8B, C9B, C10B, C11B, C12B, C13B}
{C7A, C8A, C9A, C10A, C11A, C12A, C13A} sigma for 1-2: 0.01, 1-3: 0.04
as
{C7C, C8C, C9C, C10C, C11C, C12C, C13C}
6. Others
 Sof(C7B)=Sof(H7BA)=Sof(H7BB)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=0.5*(1-FVAR(2))
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=0.5*FVAR(2)
 Sof(C7D)=Sof(H7DA)=Sof(H7DB)=Sof(C8D)=Sof(C9D)=Sof(H9D)=Sof(C10D)=Sof(H10D)=
 Sof(C11D)=Sof(H11D)=Sof(C12D)=Sof(H12D)=Sof(C13D)=Sof(H13D)=0.5*(1-FVAR(3))
 Sof(C7C)=Sof(H7CA)=Sof(H7CB)=Sof(C8C)=Sof(C9C)=Sof(H9C)=Sof(C10C)=Sof(H10C)=
 Sof(C11C)=Sof(H11C)=Sof(C12C)=Sof(H12C)=Sof(C13C)=Sof(H13C)=0.5*FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C7B(H7BA,H7BB), C7C(H7CA,H7CB), C7D(H7DA,H7DB)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B), C9C(H9C),
  C10C(H10C), C11C(H11C), C12C(H12C), C13C(H13C), C9D(H9D), C10D(H10D),
 C11D(H11D), C12D(H12D), C13D(H13D)
7.c Fitted hexagon refined as free rotating group:
 C8A(C9A,C10A,C11A,C12A,C13A), C8B(C9B,C10B,C11B,C12B,C13B), C8C(C9C,C10C,C11C,
 C12C,C13C), C8D(C9D,C10D,C11D,C12D,C13D)
;
_shelx_res_checksum              81526
_shelx_hkl_checksum              67025
_olex2_submission_special_instructions 'No special instructions were received'