Regioselective Opening of Nitroepoxides with Unsymmetrical Diamines.
Nosood, Yazdanbakhsh L.; Ziyaei Halimehjani, Azim; González, Florenci V; The Journal of organic chemistry 83 (2018) 1252–1258; doi:10.1021/acs.joc.7b02795

data_4033387
_publ_section_title
;
 Regioselective Opening of Nitroepoxides with Unsymmetrical Diamines.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1252
_journal_page_last               1258
_journal_paper_doi               10.1021/acs.joc.7b02795
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H19 N3 O2, 2(Cl)'
_chemical_formula_sum            'C16 H19 Cl2 N3 O2'
_chemical_formula_weight         356.24
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-10-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.12.12 svn.r3370 for OlexSys, GUI svn.r5273)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.8091(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.00669(15)
_cell_length_b                   7.22338(7)
_cell_length_c                   17.81970(18)
_cell_measurement_reflns_used    14982
_cell_measurement_temperature    199.95(10)
_cell_measurement_theta_max      73.2600
_cell_measurement_theta_min      5.1820
_cell_volume                     1716.53(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      199.95(10)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -49.00  36.00   0.50    1.50    --  -40.19  37.00 -60.00  170
  2  \w   -116.00 -14.00   0.50    1.50    --  -40.19 -37.00-180.00  204
  3  \w    -50.00  35.00   0.50    1.50    --  -40.19  39.00 121.00  170
  4  \w   -116.00 -14.00   0.50    1.50    --  -40.19 -37.00   0.00  204
  5  \w   -114.00 -11.00   0.50    1.50    --  -40.19 -57.00 150.00  206
  6  \w     57.00 130.00   0.50    1.50    --   40.19 178.00 -90.00  146
  7  \w     94.00 178.00   0.50    5.00    --  107.12 125.00  30.00  168
  8  \w     32.00  98.00   0.50    5.00    --  107.12 -45.00 150.00  132
  9  \w     77.00 178.00   0.50    5.00    --  107.12  62.00-147.86  202
 10  \w     73.00 178.00   0.50    5.00    --  107.12  77.00-120.00  210
 11  \w     80.00 178.00   0.50    5.00    --  107.12  45.00-150.00  196
 12  \w     23.00 109.00   0.50    5.00    --  107.12 -94.00  60.00  172
 13  \w     75.00 178.00   0.50    5.00    --  107.12  68.00 152.94  206
 14  \w     73.00 178.00   0.50    5.00    --  107.12  77.00-180.00  210
 15  \w     78.00 178.00   0.50    5.00    --  107.12  52.00  -0.79  200
 16  \w     73.00 178.00   0.50    5.00    --  107.12  77.00-150.00  210
 17  \w     77.00 178.00   0.50    5.00    --  107.12  61.00-150.00  202
 18  \w     73.00 178.00   0.50    5.00    --  107.12  77.00 150.00  210
 19  \w     77.00 178.00   0.50    5.00    --  107.12  61.00-120.00  202
 20  \w     77.00 178.00   0.50    5.00    --  107.12  61.00-180.00  202
 21  \w     29.00  91.00   0.50    5.00    --  107.12 -30.00-120.00  124
 22  \w     80.00 178.00   0.50    5.00    --  107.12  45.00-120.00  196
 23  \w     80.00 178.00   0.50    5.00    --  107.12  45.00 -90.00  196
 24  \w     77.00 178.00   0.50    5.00    --  107.12  61.00 150.00  202
 25  \w     77.00 178.00   0.50    5.00    --  107.12  30.00-120.00  202
 26  \w     77.00 178.00   0.50    5.00    --  107.12  30.00 -60.00  202
 27  \w     32.00  98.00   0.50    5.00    --  107.12 -45.00  90.00  132
 28  \w     74.00 178.00   0.50    5.00    --  107.12  74.00-161.54  208
 29  \w     77.00 178.00   0.50    5.00    --  107.12  60.00-133.42  202
 30  \w   -114.00 -11.00   0.50    1.50    --  -40.19 -57.00 -60.00  206
 31  \w   -119.00 -33.00   0.50    1.50    --  -40.19 -77.00  90.00  172
 32  \w     57.00 130.00   0.50    1.50    --   40.19 178.00 120.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         5.214
_exptl_absorpt_coefficient_mu    3.509
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.483
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.701
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.893
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0525
_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^)+(0.1029P)^2^+1.9345P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2873
_reflns_number_total             3035
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02795_si_002.cif
_cod_data_source_block           str2012_cmpd_4f
_cod_depositor_comments
'Adding full bibliography for 4033385--4033387.cif.'
_cod_database_code               4033387
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), C4(H4A,H4B), N14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C1B(H1B)
2.d Idealised Me refined as rotating group:
 C1C(H1CA,H1CB,H1CC)
;
_shelx_res_checksum              99180
_shelx_hkl_checksum              93942
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;