#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023244.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_4023244
loop_
_publ_author_name
'Clare E. Jamookeeah'
'Christopher D. Beadle'
'Richard F. W. Jackson'
'Joseph P. A. Harrity'
_publ_section_title
;
 Investigation of a Flexible Enantiospecific Approach to Aziridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1128
_journal_page_last               1130
_journal_paper_doi               10.1021/jo7023637
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C23 H22 N4'
_chemical_formula_weight         354.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           169
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   8.9977(4)
_cell_length_b                   8.9977(4)
_cell_length_c                   40.312(2)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.61
_cell_volume                     2826.4(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            59143
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.68
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0726P)²+0.2258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                2659
_reflns_number_total             2932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7023637-File001.cif
_cod_data_source_block           ohj135p61
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023244
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7443(2) 0.0196(2) 0.82833(4) 0.0226(3) Uani 1 1 d . . .
N2 N 0.3735(3) -0.2099(3) 0.79357(6) 0.0350(4) Uani 1 1 d . . .
N3 N 0.3311(3) -0.3535(3) 0.80440(5) 0.0322(4) Uani 1 1 d . . .
N4 N 0.2792(3) -0.4885(3) 0.81485(6) 0.0370(5) Uani 1 1 d . . .
C1 C 0.7480(2) 0.1011(2) 0.86101(5) 0.0194(3) Uani 1 1 d . . .
C2 C 0.5893(2) -0.0294(2) 0.88082(5) 0.0189(3) Uani 1 1 d . . .
C3 C 0.5220(3) 0.0213(3) 0.90717(5) 0.0222(4) Uani 1 1 d . . .
H3 H 0.5706 0.1398 0.9122 0.027 Uiso 1 1 calc R . .
C4 C 0.3853(3) -0.0997(3) 0.92590(5) 0.0268(4) Uani 1 1 d . . .
H4 H 0.3410 -0.0632 0.9435 0.032 Uiso 1 1 calc R . .
C5 C 0.3126(3) -0.2741(3) 0.91910(5) 0.0257(4) Uani 1 1 d . . .
H5 H 0.2187 -0.3564 0.9319 0.031 Uiso 1 1 calc R . .
C6 C 0.3789(3) -0.3265(3) 0.89339(6) 0.0248(4) Uani 1 1 d . . .
H6 H 0.3306 -0.4452 0.8886 0.030 Uiso 1 1 calc R . .
C7 C 0.5163(3) -0.2050(2) 0.87453(5) 0.0221(4) Uani 1 1 d . . .
H7 H 0.5609 -0.2424 0.8571 0.027 Uiso 1 1 calc R . .
C8 C 0.7579(2) 0.2763(2) 0.85691(5) 0.0200(3) Uani 1 1 d . . .
C9 C 0.6092(3) 0.2861(3) 0.85183(5) 0.0241(4) Uani 1 1 d . . .
H9 H 0.5003 0.1842 0.8521 0.029 Uiso 1 1 calc R . .
C10 C 0.6191(3) 0.4442(3) 0.84643(6) 0.0290(4) Uani 1 1 d . . .
H10 H 0.5170 0.4492 0.8433 0.035 Uiso 1 1 calc R . .
C11 C 0.7767(3) 0.5933(3) 0.84566(6) 0.0300(5) Uani 1 1 d . . .
H11 H 0.7829 0.7006 0.8421 0.036 Uiso 1 1 calc R . .
C12 C 0.9260(3) 0.5860(3) 0.85010(5) 0.0270(4) Uani 1 1 d . . .
H12 H 1.0346 0.6882 0.8493 0.032 Uiso 1 1 calc R . .
C13 C 0.9165(3) 0.4288(2) 0.85572(5) 0.0227(4) Uani 1 1 d . . .
H13 H 1.0191 0.4248 0.8588 0.027 Uiso 1 1 calc R . .
C14 C 0.9070(2) 0.1243(2) 0.88021(6) 0.0236(4) Uani 1 1 d . . .
C15 C 0.9467(3) 0.2060(3) 0.91086(6) 0.0280(4) Uani 1 1 d . . .
H15 H 0.8761 0.2473 0.9196 0.034 Uiso 1 1 calc R . .
C16 C 1.0881(3) 0.2283(3) 0.92898(6) 0.0344(5) Uani 1 1 d . . .
H16 H 1.1144 0.2857 0.9498 0.041 Uiso 1 1 calc R . .
C17 C 1.1908(3) 0.1660(3) 0.91647(8) 0.0393(6) Uani 1 1 d . . .
H17 H 1.2876 0.1809 0.9287 0.047 Uiso 1 1 calc R . .
C18 C 1.1514(3) 0.0827(3) 0.88634(8) 0.0403(6) Uani 1 1 d . . .
H18 H 1.2204 0.0385 0.8780 0.048 Uiso 1 1 calc R . .
C19 C 1.0115(3) 0.0626(3) 0.86791(6) 0.0306(5) Uani 1 1 d . . .
H19 H 0.9869 0.0069 0.8470 0.037 Uiso 1 1 calc R . .
C20 C 0.8480(3) 0.1281(3) 0.80060(6) 0.0309(5) Uani 1 1 d . . .
H20A H 0.9047 0.0830 0.7860 0.037 Uiso 1 1 calc R . .
H20B H 0.9132 0.2538 0.8041 0.037 Uiso 1 1 calc R . .
C21 C 0.6575(3) 0.0426(3) 0.79951(5) 0.0269(4) Uani 1 1 d . . .
H21 H 0.6094 0.1202 0.8033 0.032 Uiso 1 1 calc R . .
C22 C 0.5491(3) -0.1116(3) 0.77774(5) 0.0311(5) Uani 1 1 d . . .
H22 H 0.5338 -0.0666 0.7561 0.037 Uiso 1 1 calc R . .
C23 C 0.6261(4) -0.2236(3) 0.76995(6) 0.0356(5) Uani 1 1 d . . .
H23A H 0.6533 -0.2616 0.7907 0.053 Uiso 1 1 calc R . .
H23B H 0.7313 -0.1577 0.7569 0.053 Uiso 1 1 calc R . .
H23C H 0.5436 -0.3238 0.7572 0.053 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 0.0033 0.0000 '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 0.0061 0.0000 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 N1 C21 60.77(15) . . ?
C20 N1 C1 119.42(16) . . ?
C21 N1 C1 120.53(15) . . ?
N3 N2 C22 116.7(2) . . ?
N4 N3 N2 174.6(3) . . ?
N1 C1 C2 107.27(15) . . ?
N1 C1 C8 112.44(16) . . ?
C2 C1 C8 113.08(15) . . ?
N1 C1 C14 107.33(15) . . ?
C2 C1 C14 106.59(16) . . ?
C8 C1 C14 109.80(15) . . ?
C7 C2 C3 117.90(17) . . ?
C7 C2 C1 119.98(17) . . ?
C3 C2 C1 121.94(17) . . ?
C4 C3 C2 120.83(19) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.62(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.30(19) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 121.19(19) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C9 C8 C13 118.10(18) . . ?
C9 C8 C1 120.76(17) . . ?
C13 C8 C1 120.97(17) . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.90(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 121.04(19) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C15 C14 C19 118.6(2) . . ?
C15 C14 C1 119.45(18) . . ?
C19 C14 C1 121.9(2) . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.7(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
N1 C20 C21 59.64(13) . . ?
N1 C20 H20A 117.8 . . ?
C21 C20 H20A 117.8 . . ?
N1 C20 H20B 117.8 . . ?
C21 C20 H20B 117.8 . . ?
H20A C20 H20B 114.9 . . ?
N1 C21 C20 59.59(14) . . ?
N1 C21 C22 118.23(18) . . ?
C20 C21 C22 122.6(2) . . ?
N1 C21 H21 115.0 . . ?
C20 C21 H21 115.0 . . ?
C22 C21 H21 115.0 . . ?
N2 C22 C23 113.0(2) . . ?
N2 C22 C21 107.29(19) . . ?
C23 C22 C21 115.5(2) . . ?
N2 C22 H22 106.9 . . ?
C23 C22 H22 106.9 . . ?
C21 C22 H22 106.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C20 1.471(3) . ?
N1 C21 1.471(3) . ?
N1 C1 1.500(3) . ?
N2 N3 1.230(3) . ?
N2 C22 1.512(3) . ?
N3 N4 1.141(3) . ?
C1 C2 1.542(3) . ?
C1 C8 1.542(3) . ?
C1 C14 1.547(3) . ?
C2 C7 1.398(3) . ?
C2 C3 1.407(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.399(3) . ?
C8 C13 1.401(3) . ?
C9 C10 1.397(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C14 C19 1.399(3) . ?
C15 C16 1.392(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.488(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.514(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.514(4) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
