#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023215.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_4023215
loop_
_publ_author_name
'Xiao-an Zhang'
'Datong Song'
'Stephen J. Lippard'
_publ_section_title
;
 A Reversible pH-Dependent Intramolecular Pyridine-Aldehyde Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              734
_journal_page_last               737
_journal_paper_doi               10.1021/jo702394v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H17 Cl2 N3 O'
_chemical_formula_weight         314.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 109.7010(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3529(6)
_cell_length_b                   12.6172(8)
_cell_length_c                   13.3481(9)
_cell_measurement_temperature    426(2)
_cell_volume                     1482.97(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      426(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12477
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  0.8802
_exptl_absorpt_correction_T_min  0.8447
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0468
_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)+(0.0532P)²+0.8213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                3114
_reflns_number_total             3387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702394v-File003.cif
_cod_data_source_block           zxa2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cl1 Cl 0.91150(5) 0.76773(4) 0.35291(4) 0.03061(15) Uani 1 1 d . . .
Cl2 Cl 0.21304(5) 0.50544(4) 0.24360(4) 0.03400(15) Uani 1 1 d . . .
O1A O 0.5710(2) 0.71355(19) 0.25085(15) 0.0285(4) Uani 0.80 1 d P A 1
H1B H 0.650(4) 0.724(3) 0.265(3) 0.039(10) Uiso 0.80 1 d P B 1
O1B O 0.4498(12) 0.6609(11) 0.2629(9) 0.075(3) Uani 0.20 1 d P C 2
H1BA H 0.3930 0.6064 0.2508 0.090 Uiso 0.20 1 d PR C 2
N1 N 0.65254(19) 0.53946(14) 0.30359(13) 0.0307(4) Uani 1 1 d . . .
N2 N 0.73266(17) 0.59948(13) 0.13016(12) 0.0246(3) Uani 1 1 d . . .
N3 N 0.97564(18) 0.71988(12) 0.14317(12) 0.0238(3) Uani 1 1 d . . .
H1A H 0.928(3) 0.7196(18) 0.1869(19) 0.032(6) Uiso 1 1 d . . .
C1 C 0.6157(3) 0.5268(2) 0.3926(2) 0.0433(5) Uani 1 1 d . . .
H1 H 0.527(3) 0.565(2) 0.393(2) 0.054(8) Uiso 1 1 d . . .
C2 C 0.7063(3) 0.4670(2) 0.47574(19) 0.0455(6) Uani 1 1 d . . .
H2 H 0.682(3) 0.464(2) 0.540(2) 0.052(8) Uiso 1 1 d . . .
C3 C 0.8335(3) 0.41867(19) 0.46628(18) 0.0426(6) Uani 1 1 d . . .
H3 H 0.891(3) 0.383(2) 0.517(2) 0.056(8) Uiso 1 1 d . . .
C4 C 0.8677(3) 0.43204(17) 0.37435(18) 0.0357(5) Uani 1 1 d . . .
H4 H 0.948(3) 0.401(2) 0.367(2) 0.043(7) Uiso 1 1 d . . .
C5 C 0.7770(2) 0.49497(15) 0.29265(16) 0.0268(4) Uani 1 1 d . . .
C6 C 0.8132(2) 0.50998(16) 0.19286(16) 0.0280(4) Uani 1 1 d . . .
H6B H 0.786(3) 0.445(2) 0.1545(19) 0.036(6) Uiso 1 1 d . . .
H6A H 0.921(3) 0.5198(17) 0.2105(18) 0.029(6) Uiso 1 1 d . . .
C7 C 0.5719(2) 0.5897(2) 0.11538(18) 0.0344(5) Uani 1 1 d . . .
H7B H 0.516(3) 0.6414(19) 0.0662(19) 0.037(6) Uiso 1 1 d . . .
H7A H 0.535(3) 0.519(2) 0.096(2) 0.047(7) Uiso 1 1 d . . .
C8A C 0.5450(4) 0.6086(3) 0.2154(3) 0.0255(8) Uani 0.80 1 d P A 1
H8A H 0.446(3) 0.5893(18) 0.2101(18) 0.009(5) Uiso 0.80 1 d P D 1
C8B C 0.581(2) 0.638(2) 0.2427(14) 0.038(5) Uani 0.20 1 d P C 2
H8BA H 0.6519 0.6976 0.2636 0.046 Uiso 0.20 1 calc PR C 2
C9 C 0.7665(2) 0.61106(18) 0.03193(16) 0.0314(4) Uani 1 1 d . . .
H9B H 0.767(3) 0.541(2) -0.0061(19) 0.037(6) Uiso 1 1 d . . .
H9A H 0.691(3) 0.6523(19) -0.014(2) 0.038(6) Uiso 1 1 d . . .
C10 C 0.9173(2) 0.66502(15) 0.05239(14) 0.0253(4) Uani 1 1 d . A .
C11 C 0.9964(3) 0.66334(18) -0.01858(16) 0.0342(5) Uani 1 1 d . . .
H11 H 0.951(3) 0.626(2) -0.083(2) 0.047(7) Uiso 1 1 d . . .
C12 C 1.1330(3) 0.71659(19) 0.00671(19) 0.0384(5) Uani 1 1 d . A .
H12 H 1.182(3) 0.717(2) -0.042(2) 0.048(7) Uiso 1 1 d . . .
C13 C 1.1895(3) 0.77153(18) 0.10167(19) 0.0380(5) Uani 1 1 d . . .
H13 H 1.276(3) 0.808(2) 0.120(2) 0.047(7) Uiso 1 1 d . . .
C14 C 1.1081(2) 0.77186(16) 0.16967(17) 0.0307(4) Uani 1 1 d . A .
H14 H 1.141(3) 0.8041(18) 0.2329(18) 0.028(6) Uiso 1 1 d . . .
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'
O O 0.0106 0.0060 '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
C8B O1B Cl2 123.0(13) . . ?
C5 N1 C1 122.15(19) . . ?
C5 N1 C8B 121.8(7) . . ?
C1 N1 C8B 111.8(7) . . ?
C5 N1 C8A 121.4(2) . . ?
C1 N1 C8A 116.5(2) . . ?
C8B N1 C8A 20.7(7) . . ?
C7 N2 C6 108.84(16) . . ?
C7 N2 C9 114.51(15) . . ?
C6 N2 C9 111.61(16) . . ?
C14 N3 C10 123.35(17) . . ?
N1 C1 C2 120.3(2) . . ?
C1 C2 C3 119.0(2) . . ?
C4 C3 C2 119.6(2) . . ?
C3 C4 C5 120.4(2) . . ?
N1 C5 C4 118.50(19) . . ?
N1 C5 C6 120.61(17) . . ?
C4 C5 C6 120.86(19) . . ?
N2 C6 C5 112.50(16) . . ?
N2 C7 C8A 110.6(2) . . ?
N2 C7 C8B 97.3(6) . . ?
C8A C7 C8B 15.8(7) . . ?
O1A C8A C7 113.6(3) . . ?
O1A C8A N1 106.5(3) . . ?
C7 C8A N1 109.8(3) . . ?
O1B C8B N1 109.3(14) . . ?
O1B C8B C7 120.1(13) . . ?
N1 C8B C7 95.9(12) . . ?
N2 C9 C10 110.89(15) . . ?
N3 C10 C11 118.51(18) . . ?
N3 C10 C9 117.91(17) . . ?
C11 C10 C9 123.55(18) . . ?
C12 C11 C10 119.3(2) . . ?
C11 C12 C13 120.3(2) . . ?
C14 C13 C12 118.9(2) . . ?
N3 C14 C13 119.7(2) . . ?
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
Cl2 O1B 2.904(12) . ?
O1A C8A 1.400(4) . ?
O1B C8B 1.37(2) . ?
N1 C5 1.344(3) . ?
N1 C1 1.354(3) . ?
N1 C8B 1.51(2) . ?
N1 C8A 1.536(4) . ?
N2 C7 1.454(2) . ?
N2 C6 1.455(2) . ?
N2 C9 1.456(2) . ?
N3 C14 1.339(3) . ?
N3 C10 1.341(2) . ?
C1 C2 1.373(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.384(3) . ?
C5 C6 1.493(3) . ?
C7 C8A 1.459(5) . ?
C7 C8B 1.780(18) . ?
C9 C10 1.506(3) . ?
C10 C11 1.385(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.368(3) . ?
