Catalyst-Free Synthesis of Aryl Diamines via a Three-Step Reaction Process.
Bulut, Safak; Queen, Wendy L.; The Journal of organic chemistry 83 (2018) 3806–3818; doi:10.1021/acs.joc.8b00151

data_4035501
_publ_section_title
;
 Catalyst-Free Synthesis of Aryl Diamines via a Three-Step Reaction
 Process.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3806
_journal_page_last               3818
_journal_paper_doi               10.1021/acs.joc.8b00151
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_chemical_name_common            'CCDC 1540292_Compound 6_SB97d_2_0m'
_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     direct
_audit_creation_date             2016-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.552(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0825(12)
_cell_length_b                   10.495(3)
_cell_length_c                   13.156(3)
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      48.560
_cell_measurement_theta_min      4.999
_cell_volume                     689.9(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  Venture
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10854
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.749
_diffrn_reflns_theta_max         24.749
_diffrn_reflns_theta_min         2.499
_exptl_absorpt_coefficient_mu    0.105
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0744
_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^)+(0.1293P)^2^+0.8606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1963
_refine_ls_wR_factor_ref         0.2159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                984
_reflns_number_total             1211
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00151_si_002.cif
_cod_data_source_block           sb97d_2_0m
_cod_database_code               4035501
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.743(4) 0.257(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C006(H006), C008(H008), C00B(H00C)
3.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_shelx_res_checksum              58238
_shelx_hkl_checksum              59684
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'