#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/33/4033385.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4033385
loop_
_publ_author_name
'Nosood, Yazdanbakhsh L.'
'Ziyaei Halimehjani, Azim'
'González, Florenci V'
_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_sum            'C17 H16 N2'
_chemical_formula_weight         248.32
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.117(4)
_cell_angle_beta                 89.625(3)
_cell_angle_gamma                79.854(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1210(3)
_cell_length_b                   8.6165(4)
_cell_length_c                   10.0149(4)
_cell_measurement_reflns_used    3683
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.1100
_cell_measurement_theta_min      4.4410
_cell_volume                     681.40(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7146
_diffrn_reflns_theta_full        66.55
_diffrn_reflns_theta_max         66.55
_diffrn_reflns_theta_min         4.47
_exptl_absorpt_coefficient_mu    0.553
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   gaussian
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0806P)²+0.0535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                2127
_reflns_number_total             2418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02795_si_002.cif
_cod_data_source_block           str2009_cmpd_2b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033385--4033387.cif.
;
_cod_original_cell_volume        681.41(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4033385
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C12 C 0.31960(14) 0.18293(13) 0.07009(11) 0.0445(3) Uani 1 1 d .
C1 C 0.24155(15) 0.14245(14) 0.20251(12) 0.0451(3) Uani 1 1 d .
N10 N 0.01245(13) -0.00643(13) 0.26340(11) 0.0519(3) Uani 1 1 d .
N2 N 0.32867(14) 0.12837(14) 0.31077(10) 0.0544(3) Uani 1 1 d .
C17 C 0.27328(16) 0.12398(15) -0.04275(13) 0.0524(3) Uani 1 1 d .
H17 H 0.1887 0.0633 -0.0362 0.063 Uiso 1 1 calc R
C9 C 0.11947(15) -0.12754(16) 0.34890(13) 0.0507(3) Uani 1 1 d .
C16 C 0.35111(19) 0.15435(18) -0.16439(14) 0.0630(4) Uani 1 1 d .
H16 H 0.3200 0.1130 -0.2390 0.076 Uiso 1 1 calc R
C11 C 0.06263(15) 0.11743(15) 0.20146(12) 0.0485(3) Uani 1 1 d .
C4 C 0.23023(16) -0.09296(18) 0.44172(12) 0.0558(3) Uani 1 1 d .
C13 C 0.44539(16) 0.27392(16) 0.05822(13) 0.0543(3) Uani 1 1 d .
H13 H 0.4784 0.3138 0.1330 0.065 Uiso 1 1 calc R
C3 C 0.2481(2) 0.0778(2) 0.43785(13) 0.0630(4) Uani 1 1 d .
H3A H 0.1390 0.1440 0.4422 0.076 Uiso 1 1 calc R
H3B H 0.3159 0.0881 0.5143 0.076 Uiso 1 1 calc R
C14 C 0.52174(18) 0.30557(18) -0.06389(15) 0.0635(4) Uani 1 1 d .
H14 H 0.6053 0.3675 -0.0713 0.076 Uiso 1 1 calc R
C18 C -0.06423(17) 0.24807(18) 0.12379(16) 0.0632(4) Uani 1 1 d .
H18A H -0.1751 0.2223 0.1387 0.076 Uiso 1 1 calc R
H18B H -0.0424 0.2539 0.0280 0.076 Uiso 1 1 calc R
C8 C 0.10108(19) -0.28425(18) 0.34770(16) 0.0646(4) Uani 1 1 d .
H8 H 0.0243 -0.3069 0.2882 0.078 Uiso 1 1 calc R
C15 C 0.47471(19) 0.24579(18) -0.17521(14) 0.0650(4) Uani 1 1 d .
H15 H 0.5266 0.2673 -0.2574 0.078 Uiso 1 1 calc R
C5 C 0.3225(2) -0.2182(2) 0.53055(14) 0.0727(5) Uani 1 1 d .
H5 H 0.3959 -0.1967 0.5933 0.087 Uiso 1 1 calc R
C6 C 0.3056(2) -0.3728(2) 0.52583(18) 0.0837(5) Uani 1 1 d .
H6 H 0.3686 -0.4555 0.5849 0.100 Uiso 1 1 calc R
C19 C -0.0601(2) 0.40947(19) 0.16546(18) 0.0793(5) Uani 1 1 d .
H19A H -0.1475 0.4878 0.1179 0.119 Uiso 1 1 calc R
H19B H 0.0463 0.4397 0.1438 0.119 Uiso 1 1 calc R
H19C H -0.0767 0.4030 0.2610 0.119 Uiso 1 1 calc R
C7 C 0.1964(2) -0.4069(2) 0.43451(19) 0.0808(5) Uani 1 1 d .
H7 H 0.1867 -0.5122 0.4313 0.097 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 C12 C17 118.76(12)
C13 C12 C1 120.72(11)
C17 C12 C1 120.45(11)
N2 C1 C12 119.03(11)
N2 C1 C11 123.28(11)
C12 C1 C11 117.68(10)
C11 N10 C9 122.23(10)
C1 N2 C3 116.42(11)
C16 C17 C12 120.80(12)
C8 C9 C4 119.88(13)
C8 C9 N10 117.79(12)
C4 C9 N10 122.06(12)
C15 C16 C17 119.91(13)
N10 C11 C18 118.46(11)
N10 C11 C1 124.08(11)
C18 C11 C1 117.45(11)
C5 C4 C9 118.96(15)
C5 C4 C3 122.99(13)
C9 C4 C3 118.03(12)
C14 C13 C12 120.33(12)
N2 C3 C4 107.82(11)
C13 C14 C15 120.29(13)
C11 C18 C19 112.19(12)
C7 C8 C9 120.25(15)
C16 C15 C14 119.90(13)
C6 C5 C4 120.37(15)
C5 C6 C7 120.69(15)
C6 C7 C8 119.80(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C12 C13 1.3871(17)
C12 C17 1.3881(17)
C12 C1 1.4854(16)
C1 N2 1.2766(16)
C1 C11 1.5064(16)
N10 C11 1.2788(16)
N10 C9 1.4113(17)
N2 C3 1.4683(16)
C17 C16 1.3790(19)
C9 C8 1.386(2)
C9 C4 1.3975(18)
C16 C15 1.375(2)
C11 C18 1.5050(18)
C4 C5 1.395(2)
C4 C3 1.498(2)
C13 C14 1.3787(19)
C14 C15 1.381(2)
C18 C19 1.518(2)
C8 C7 1.382(2)
C5 C6 1.371(3)
C6 C7 1.377(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095913
