#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/83/2218378.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2218378
loop_
_publ_author_name
'Xu, Liang-Zhong'
'Yang, Zhi'
'Yi, Xu'
'An, Guang-Wei'
_publ_section_title
(E)-N-(6-Chloro-3-pyridylmethyl)-N-ethyl-N'-methyl-2-nitroethylene-1,1-diamine
_journal_coeditor_code           CV2407
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1074
_journal_paper_doi               10.1107/S1600536808013317
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H15 Cl N4 O2'
_chemical_formula_moiety         'C11 H15 Cl N4 O2'
_chemical_formula_sum            'C11 H15 Cl N4 O2'
_chemical_formula_weight         270.72
_chemical_name_systematic
(E)-N-(6-Chloro-3-pyridylmethyl)-N-ethyl-N'-methyl-2-nitroethylene-1,1-diamine
_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                 92.34(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7252(15)
_cell_length_b                   7.9281(16)
_cell_length_c                   20.787(4)
_cell_measurement_reflns_used    3653
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.888
_cell_measurement_theta_min      1.965
_cell_volume                     1272.1(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7120
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0332
_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)+(0.053P)²+0.2942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                1970
_reflns_number_total             2238
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2407.cif
_cod_data_source_block           I
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1272.0(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2218378
_cod_database_fobs_code          2218378
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 -0.46834(6) 0.13093(5) 0.15973(2) 0.03277(16) Uani d . 1
O O1 0.31814(14) 1.08651(13) -0.00180(6) 0.0256(3) Uani d . 1
O O2 0.11880(15) 1.26510(13) 0.02461(6) 0.0297(3) Uani d . 1
N N1 -0.37165(16) 0.43140(16) 0.19759(6) 0.0218(3) Uani d . 1
N N2 0.10858(15) 0.74385(14) 0.12607(6) 0.0154(3) Uani d . 1
N N3 0.34655(15) 0.80473(14) 0.06527(6) 0.0164(3) Uani d . 1
H H3A 0.4171 0.8837 0.0555 0.020 Uiso calc R 1
N N4 0.19059(16) 1.12460(14) 0.03211(6) 0.0187(3) Uani d . 1
C C1 -0.34845(19) 0.31625(19) 0.15333(7) 0.0194(3) Uani d . 1
C C2 -0.23838(19) 0.33022(19) 0.10271(8) 0.0193(3) Uani d . 1
H H2 -0.2261 0.2429 0.0734 0.023 Uiso calc R 1
C C3 -0.14779(18) 0.47891(18) 0.09762(7) 0.0183(3) Uani d . 1
H H3 -0.0727 0.4941 0.0642 0.022 Uiso calc R 1
C C4 -0.16921(18) 0.60648(17) 0.14276(7) 0.0157(3) Uani d . 1
C C5 -0.28034(19) 0.57502(19) 0.19164(7) 0.0193(3) Uani d . 1
H H5 -0.2931 0.6584 0.2225 0.023 Uiso calc R 1
C C6 -0.07572(18) 0.77266(17) 0.13772(7) 0.0170(3) Uani d . 1
H H6A -0.1280 0.8384 0.1027 0.020 Uiso calc R 1
H H6B -0.0863 0.8360 0.1773 0.020 Uiso calc R 1
C C7 0.20362(19) 0.64947(18) 0.17777(7) 0.0177(3) Uani d . 1
H H7A 0.2889 0.5772 0.1586 0.021 Uiso calc R 1
H H7B 0.1228 0.5777 0.1996 0.021 Uiso calc R 1
C C8 0.2939(2) 0.7633(2) 0.22653(9) 0.0301(4) Uani d . 1
H H8A 0.3829 0.8259 0.2062 0.045 Uiso calc R 1
H H8B 0.3449 0.6965 0.2608 0.045 Uiso calc R 1
H H8C 0.2115 0.8402 0.2436 0.045 Uiso calc R 1
C C9 0.19636(18) 0.85310(17) 0.08850(7) 0.0142(3) Uani d . 1
C C10 0.4040(2) 0.63299(18) 0.05466(8) 0.0206(3) Uani d . 1
H H10A 0.4731 0.5955 0.0913 0.031 Uiso calc R 1
H H10B 0.4718 0.6292 0.0170 0.031 Uiso calc R 1
H H10C 0.3050 0.5607 0.0486 0.031 Uiso calc R 1
C C11 0.12900(18) 1.01529(17) 0.07620(7) 0.0169(3) Uani d . 1
H H11 0.0359 1.0503 0.0999 0.020 Uiso calc R 1
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
C1 N1 C5 115.85(13)
C9 N2 C6 120.14(12)
C9 N2 C7 119.54(12)
C6 N2 C7 114.44(11)
C9 N3 C10 126.98(12)
C9 N3 H3A 116.5
C10 N3 H3A 116.5
O2 N4 O1 119.49(12)
O2 N4 C11 119.03(12)
O1 N4 C11 121.48(12)
N1 C1 C2 125.63(13)
N1 C1 Cl1 116.35(11)
C2 C1 Cl1 118.03(12)
C3 C2 C1 117.18(14)
C3 C2 H2 121.4
C1 C2 H2 121.4
C2 C3 C4 119.65(14)
C2 C3 H3 120.2
C4 C3 H3 120.2
C5 C4 C3 117.33(13)
C5 C4 C6 121.56(13)
C3 C4 C6 121.10(13)
N1 C5 C4 124.34(14)
N1 C5 H5 117.8
C4 C5 H5 117.8
N2 C6 C4 110.19(11)
N2 C6 H6A 109.6
C4 C6 H6A 109.6
N2 C6 H6B 109.6
C4 C6 H6B 109.6
H6A C6 H6B 108.1
N2 C7 C8 112.82(12)
N2 C7 H7A 109.0
C8 C7 H7A 109.0
N2 C7 H7B 109.0
C8 C7 H7B 109.0
H7A C7 H7B 107.8
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N3 C9 N2 119.04(12)
N3 C9 C11 121.26(13)
N2 C9 C11 119.69(12)
N3 C10 H10A 109.5
N3 C10 H10B 109.5
H10A C10 H10B 109.5
N3 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N4 C11 C9 124.57(13)
N4 C11 H11 117.7
C9 C11 H11 117.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7447(15)
O1 N4 1.2711(16)
O2 N4 1.2512(16)
N1 C1 1.314(2)
N1 C5 1.3478(19)
N2 C9 1.3650(18)
N2 C6 1.4717(17)
N2 C7 1.4796(19)
N3 C9 1.3313(18)
N3 C10 1.4517(18)
N3 H3A 0.8600
N4 C11 1.3613(18)
C1 C2 1.384(2)
C2 C3 1.377(2)
C2 H2 0.9300
C3 C4 1.394(2)
C3 H3 0.9300
C4 C5 1.379(2)
C4 C6 1.508(2)
C5 H5 0.9300
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.507(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C11 1.4066(19)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A O1 . 0.86 2.12 2.6376(16) 117.8
N3 H3A O1 3_675 0.86 2.38 3.0778(17) 138.4
C6 H6A O1 3_575 0.97 2.58 3.508(2) 160.0
C3 H3 O2 1_545 0.93 2.50 3.1101(19) 123.1
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 C2 0.8(2)
C5 N1 C1 Cl1 -179.06(11)
N1 C1 C2 C3 -1.3(2)
Cl1 C1 C2 C3 178.57(11)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 C5 1.0(2)
C2 C3 C4 C6 -178.39(13)
C1 N1 C5 C4 0.7(2)
C3 C4 C5 N1 -1.6(2)
C6 C4 C5 N1 177.82(13)
C9 N2 C6 C4 145.80(13)
C7 N2 C6 C4 -61.31(16)
C5 C4 C6 N2 133.23(14)
C3 C4 C6 N2 -47.41(19)
C9 N2 C7 C8 58.95(17)
C6 N2 C7 C8 -94.11(15)
C10 N3 C9 N2 23.9(2)
C10 N3 C9 C11 -157.47(15)
C6 N2 C9 N3 -163.24(13)
C7 N2 C9 N3 45.24(19)
C6 N2 C9 C11 18.2(2)
C7 N2 C9 C11 -133.36(14)
O2 N4 C11 C9 179.01(14)
O1 N4 C11 C9 -0.4(2)
N3 C9 C11 N4 11.8(2)
N2 C9 C11 N4 -169.61(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7971209
