#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025855.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_4025855
loop_
_publ_author_name
'Jinbao Xiang'
'Tong Zhu'
'Qun Dang'
'Xu Bai'
_publ_section_title
;
 Stereochemistry as a Tool in Deciphering the Processes of a Tandem
 Iminium Cyclization and Smiles Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8147
_journal_page_last               8154
_journal_paper_doi               10.1021/jo101798p
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H17 Cl2 N5'
_chemical_formula_sum            'C19 H17 Cl2 N5'
_chemical_formula_weight         386.28
_chemical_melting_point          ?
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 106.79(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.511(2)
_cell_length_b                   7.9696(16)
_cell_length_c                   11.326(2)
_cell_measurement_temperature    293(2)
_cell_volume                     908.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_measured_fraction_theta_full 0.992
_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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8959
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.902
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4058
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.827
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1354P)²+0.2288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2158
_reflns_number_gt                3349
_reflns_number_total             4058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101798p_si_003.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4025855
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7573(6) 0.9281(9) 0.0069(5) 0.0478(13) Uani 1 1 d D . .
C2 C 0.7114(7) 0.8406(10) -0.1056(5) 0.0569(16) Uani 1 1 d D . .
H2 H 0.6334 0.7781 -0.1235 0.068 Uiso 1 1 calc R . .
C3 C 0.7853(9) 0.8499(12) -0.1891(6) 0.069(2) Uani 1 1 d . . .
H3 H 0.7557 0.7961 -0.2650 0.083 Uiso 1 1 calc R . .
C4 C 0.9044(7) 0.9404(12) -0.1590(6) 0.0624(19) Uani 1 1 d . . .
C5 C 0.9488(7) 1.0211(13) -0.0496(7) 0.070(2) Uani 1 1 d . . .
H5 H 1.0289 1.0792 -0.0303 0.084 Uiso 1 1 calc R . .
C6 C 0.8747(6) 1.0168(12) 0.0333(6) 0.0624(19) Uani 1 1 d . . .
H6 H 0.9044 1.0744 0.1077 0.075 Uiso 1 1 calc R . .
C7 C 0.7558(5) 0.9249(9) 0.2278(5) 0.0485(14) Uani 1 1 d . . .
H7 H 0.8478 0.8903 0.2383 0.058 Uiso 1 1 calc R . .
C8 C 0.6958(6) 0.8023(8) 0.2956(5) 0.0469(13) Uani 1 1 d . . .
C9 C 0.7461(8) 0.7050(10) 0.3966(6) 0.0630(18) Uani 1 1 d . . .
H9 H 0.8352 0.6957 0.4415 0.076 Uiso 1 1 calc R . .
C10 C 0.6365(10) 0.6190(11) 0.4212(7) 0.073(2) Uani 1 1 d . . .
H10 H 0.6417 0.5443 0.4855 0.088 Uiso 1 1 calc R . .
C11 C 0.5249(8) 0.6659(10) 0.3347(6) 0.0598(17) Uani 1 1 d . . .
H11 H 0.4395 0.6272 0.3278 0.072 Uiso 1 1 calc R . .
C12 C 0.4810(6) 0.8553(8) 0.1478(5) 0.0432(11) Uani 1 1 d . . .
C13 C 0.5464(5) 0.9135(8) 0.0628(5) 0.0425(11) Uani 1 1 d . . .
C14 C 0.3468(6) 0.9754(9) -0.0718(6) 0.0514(14) Uani 1 1 d . . .
H14 H 0.2989 1.0075 -0.1511 0.062 Uiso 1 1 calc R . .
C15 C 0.3451(6) 0.8847(9) 0.1137(6) 0.0505(14) Uani 1 1 d . . .
C16 C 0.7587(7) 1.1042(10) 0.2764(5) 0.0552(16) Uani 1 1 d . . .
H16 H 0.7894 1.1792 0.2217 0.066 Uiso 1 1 calc R . .
C17 C 0.8554(11) 1.1204(13) 0.4094(7) 0.085(3) Uani 1 1 d DU . .
H17A H 0.8910 1.0116 0.4406 0.102 Uiso 1 1 calc R . .
H17B H 0.9285 1.1950 0.4103 0.102 Uiso 1 1 calc R . .
C18 C 0.7744(17) 1.189(3) 0.4832(17) 0.142(5) Uani 1 1 d DU . .
H18A H 0.7903 1.3088 0.4956 0.170 Uiso 1 1 calc R . .
H18B H 0.7963 1.1351 0.5632 0.170 Uiso 1 1 calc R . .
C19 C 0.6267(13) 1.1560(19) 0.4109(13) 0.106(3) Uani 1 1 d U . .
H19A H 0.5976 1.0474 0.4317 0.127 Uiso 1 1 calc R . .
H19B H 0.5691 1.2424 0.4274 0.127 Uiso 1 1 calc R . .
Cl1 Cl 0.25341(18) 0.8535(3) 0.21816(19) 0.0744(6) Uani 1 1 d . . .
Cl2 Cl 0.9956(2) 0.9513(5) -0.26567(19) 0.0909(7) Uani 1 1 d U . .
N1 N 0.6837(5) 0.9124(8) 0.0954(4) 0.0468(11) Uani 1 1 d . . .
N2 N 0.5590(5) 0.7815(7) 0.2578(4) 0.0458(11) Uani 1 1 d . . .
N3 N 0.4783(5) 0.9698(7) -0.0488(4) 0.0458(11) Uani 1 1 d . . .
N4 N 0.2762(5) 0.9409(8) 0.0046(5) 0.0557(13) Uani 1 1 d . . .
N5 N 0.6282(7) 1.1609(9) 0.2810(6) 0.0663(16) Uani 1 1 d . . .
H5A H 0.5538 1.1801 0.2201 0.080 Uiso 1 1 d 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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 120.1(6) . . ?
C6 C1 N1 121.4(5) . . ?
C2 C1 N1 118.3(6) . . ?
C3 C2 C1 118.4(7) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 121.1(6) . . ?
C5 C4 Cl2 119.7(6) . . ?
C3 C4 Cl2 119.2(6) . . ?
C4 C5 C6 119.8(7) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.6(7) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C8 108.0(5) . . ?
N1 C7 C16 112.3(5) . . ?
C8 C7 C16 113.3(5) . . ?
N1 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C16 C7 H7 107.6 . . ?
C9 C8 N2 108.0(6) . . ?
C9 C8 C7 133.6(6) . . ?
N2 C8 C7 118.3(5) . . ?
C8 C9 C10 107.3(7) . . ?
C8 C9 H9 126.3 . . ?
C10 C9 H9 126.3 . . ?
C11 C10 C9 107.8(6) . . ?
C11 C10 H10 126.1 . . ?
C9 C10 H10 126.1 . . ?
C10 C11 N2 108.2(7) . . ?
C10 C11 H11 125.9 . . ?
N2 C11 H11 125.9 . . ?
C15 C12 N2 127.3(5) . . ?
C15 C12 C13 114.8(5) . . ?
N2 C12 C13 117.8(5) . . ?
N3 C13 N1 119.2(5) . . ?
N3 C13 C12 121.4(5) . . ?
N1 C13 C12 119.5(5) . . ?
N4 C14 N3 127.7(6) . . ?
N4 C14 H14 116.1 . . ?
N3 C14 H14 116.1 . . ?
N4 C15 C12 124.1(5) . . ?
N4 C15 Cl1 115.0(5) . . ?
C12 C15 Cl1 120.9(5) . . ?
N5 C16 C7 112.4(5) . . ?
N5 C16 C17 107.3(7) . . ?
C7 C16 C17 111.4(6) . . ?
N5 C16 H16 108.6 . . ?
C7 C16 H16 108.6 . . ?
C17 C16 H16 108.6 . . ?
C18 C17 C16 105.0(10) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C17 C18 C19 107.0(14) . . ?
C17 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
C17 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
N5 C19 C18 102.9(11) . . ?
N5 C19 H19A 111.2 . . ?
C18 C19 H19A 111.2 . . ?
N5 C19 H19B 111.2 . . ?
C18 C19 H19B 111.2 . . ?
H19A C19 H19B 109.1 . . ?
C13 N1 C1 122.9(4) . . ?
C13 N1 C7 117.5(4) . . ?
C1 N1 C7 118.7(4) . . ?
C11 N2 C8 108.6(5) . . ?
C11 N2 C12 130.2(6) . . ?
C8 N2 C12 120.6(5) . . ?
C14 N3 C13 116.0(5) . . ?
C15 N4 C14 115.1(5) . . ?
C16 N5 C19 107.9(8) . . ?
C16 N5 H5A 130.4 . . ?
C19 N5 H5A 120.9 . . ?
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
C1 C6 1.378(10) . ?
C1 C2 1.410(9) . ?
C1 N1 1.439(7) . ?
C2 C3 1.389(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(12) . ?
C4 Cl2 1.748(6) . ?
C5 C6 1.383(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.475(7) . ?
C7 C8 1.490(9) . ?
C7 C16 1.529(11) . ?
C7 H7 0.9800 . ?
C8 C9 1.356(9) . ?
C8 N2 1.387(8) . ?
C9 C10 1.435(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.346(12) . ?
C10 H10 0.9300 . ?
C11 N2 1.384(9) . ?
C11 H11 0.9300 . ?
C12 C15 1.388(8) . ?
C12 N2 1.408(7) . ?
C12 C13 1.412(8) . ?
C13 N3 1.337(7) . ?
C13 N1 1.382(7) . ?
C14 N4 1.322(9) . ?
C14 N3 1.331(8) . ?
C14 H14 0.9300 . ?
C15 N4 1.317(9) . ?
C15 Cl1 1.746(6) . ?
C16 N5 1.458(10) . ?
C16 C17 1.560(9) . ?
C16 H16 0.9800 . ?
C17 C18 1.462(18) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.55(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N5 1.477(15) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
N5 H5A 0.8942 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659316
