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_4516914
_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, C4 H8 O'
_chemical_formula_sum            'C30 H28 N4 O9'
_chemical_formula_weight         588.56
_chemical_name_systematic
'Bis(phenylmethyl) 2,8-Dinitro-1,5-naphthalenediylcarbamate THF solvate'
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-05-16 deposited with the CCDC.
2017-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.741(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.095(4)
_cell_length_b                   21.593(5)
_cell_length_c                   8.257(2)
_cell_measurement_reflns_used    4006
_cell_measurement_temperature    150
_cell_measurement_theta_max      47.557
_cell_measurement_theta_min      2.440
_cell_volume                     2809.6(12)
_computing_cell_refinement
'SAINT (2013) V8.37A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
'SAINT (2013) V8.37A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1580
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            24254
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        48.518
_diffrn_reflns_theta_max         48.518
_diffrn_reflns_theta_min         2.439
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.561
_exptl_absorpt_correction_T_max  0.7495
_exptl_absorpt_correction_T_min  0.3021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1832 before and 0.1070 after correction. The Ratio of minimum to maximum transmission is 0.4031. The \l/2 correction factor is Not present.'
_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    1.391
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method 'crystallized in THF'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         4070
_refine_ls_number_restraints     212
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1921
_refine_ls_R_factor_gt           0.0978
_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^)+(0.1471P)^2^+2.2889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2271
_refine_ls_wR_factor_ref         0.2893
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1961
_reflns_number_total             4070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao7b01055_si_005.cif
_cod_data_source_block           jw1893
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4516914
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.936
_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. Restrained distances
 C12A-C13A \\sim C12B-C13B
 with sigma of 0.02
 O1-C12A \\sim O1-C12B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C12A \\sim C13A \\sim C14A \\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim
C12B \\sim C13B \\sim C14B \\sim C15B \\sim C16B \\sim C17B \\sim C18B: within
2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C12A) = Uanis(C12B)
4. Others
 Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=
 Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=1-FVAR(1)
 Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,
 H30B), C12A(H12A,H12B), C12B(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A), C18A(H18A),
  C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B)
5.c Fitted hexagon refined as free rotating group:
 C13A(C14A,C15A,C16A,C17A,C18A), C13B(C14B,C15B,C16B,C17B,C18B)
;
_shelx_res_checksum              2938
_shelx_hkl_checksum              33596
_olex2_date_sample_data_collection 2017-02-06
_olex2_date_sample_submission    2017-02-06
_olex2_exptl_crystal_mounting_method 'mounted on a Cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'