#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/84/2218418.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_2218418
loop_
_publ_author_name
'Hu, Xian-Chao'
'Lv, Lu-Ping'
'Li, Wei-Wei'
'Yu, Wen-Bo'
_publ_section_title
;
 (E)-Methyl 2-[4-(dimethylamino)benzylidene]hydrazinecarboxylate
 at 123 K
;
_journal_coeditor_code           HB2730
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1081
_journal_paper_doi               10.1107/S1600536808013950
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H15 N3 O2'
_chemical_formula_moiety         'C11 H15 N3 O2'
_chemical_formula_sum            'C11 H15 N3 O2'
_chemical_formula_weight         221.26
_chemical_name_systematic
;
(E)-Methyl 2-[4-(dimethylamino)benzylidene]hydrazinecarboxylate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.051(3)
_cell_length_b                   9.838(2)
_cell_length_c                   18.637(4)
_cell_measurement_reflns_used    2111
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.2
_cell_volume                     2392.9(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19378
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0456
_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)+(0.0719P)²+0.3078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1335
_reflns_number_gt                1592
_reflns_number_total             2111
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2730.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_database_code               2218418
_cod_database_fobs_code          2218418
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
N N2 0.27645(11) 0.23338(15) 0.56388(7) 0.0539(4) Uani d . 1
C C9 0.29967(13) 0.13610(19) 0.60663(9) 0.0546(5) Uani d . 1
H H9 0.2897 0.0469 0.5916 0.066 Uiso calc R 1
O O2 0.17803(10) 0.22366(12) 0.38955(6) 0.0610(4) Uani d . 1
N N3 0.23964(12) 0.19224(14) 0.49757(7) 0.0554(4) Uani d . 1
H H3 0.2363 0.1072 0.4871 0.067 Uiso calc R 1
O O1 0.20751(10) 0.40732(12) 0.45884(7) 0.0656(4) Uani d . 1
C C3 0.42170(14) 0.20049(17) 0.81830(9) 0.0536(4) Uani d . 1
C C8 0.34112(13) 0.16094(17) 0.67786(9) 0.0513(4) Uani d . 1
C C5 0.40355(14) 0.31063(17) 0.77132(10) 0.0567(5) Uani d . 1
H H5 0.4182 0.3986 0.7865 0.068 Uiso calc R 1
C C10 0.20925(12) 0.28641(17) 0.44977(9) 0.0492(4) Uani d . 1
N N1 0.45818(14) 0.22037(16) 0.88679(9) 0.0725(5) Uani d . 1
C C7 0.36472(13) 0.29041(18) 0.70360(10) 0.0542(4) Uani d . 1
H H7 0.3538 0.3652 0.6741 0.065 Uiso calc R 1
C C6 0.35985(14) 0.05251(18) 0.72400(10) 0.0593(5) Uani d . 1
H H6 0.3453 -0.0352 0.7085 0.071 Uiso calc R 1
C C4 0.39921(15) 0.07084(18) 0.79189(10) 0.0621(5) Uani d . 1
H H4 0.4111 -0.0046 0.8208 0.075 Uiso calc R 1
C C11 0.14121(16) 0.30910(19) 0.33264(10) 0.0667(5) Uani d . 1
H H11A 0.1216 0.2538 0.2925 0.100 Uiso calc R 1
H H11B 0.1945 0.3707 0.3183 0.100 Uiso calc R 1
H H11C 0.0830 0.3599 0.3491 0.100 Uiso calc R 1
C C1 0.48056(19) 0.1055(2) 0.93250(11) 0.0833(7) Uani d . 1
H H1A 0.5057 0.1373 0.9779 0.125 Uiso calc R 1
H H1B 0.5316 0.0494 0.9101 0.125 Uiso calc R 1
H H1C 0.4193 0.0534 0.9398 0.125 Uiso calc R 1
C C2 0.48463(18) 0.3522(2) 0.91387(11) 0.0787(6) Uani d . 1
H H2A 0.5090 0.3439 0.9623 0.118 Uiso calc R 1
H H2B 0.4252 0.4098 0.9130 0.118 Uiso calc R 1
H H2C 0.5374 0.3912 0.8845 0.118 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N2 0.0641(9) 0.0466(9) 0.0509(9) 0.0017(6) -0.0001(7) -0.0056(7)
C9 0.0610(10) 0.0438(10) 0.0590(11) 0.0027(8) 0.0039(8) -0.0028(8)
O2 0.0838(9) 0.0425(7) 0.0568(8) 0.0004(6) -0.0117(6) -0.0050(6)
N3 0.0736(10) 0.0383(8) 0.0544(9) 0.0020(6) -0.0048(7) -0.0056(6)
O1 0.0912(9) 0.0344(7) 0.0713(9) 0.0016(6) -0.0085(7) -0.0070(6)
C3 0.0545(10) 0.0476(10) 0.0588(11) 0.0041(7) -0.0009(8) 0.0036(8)
C8 0.0537(9) 0.0449(9) 0.0555(11) 0.0020(7) 0.0052(8) 0.0011(8)
C5 0.0671(11) 0.0407(10) 0.0622(11) 0.0004(8) -0.0026(9) 0.0013(8)
C10 0.0564(9) 0.0376(9) 0.0537(10) -0.0007(7) 0.0042(8) -0.0053(7)
N1 0.0990(13) 0.0545(10) 0.0639(10) 0.0029(9) -0.0233(9) 0.0063(8)
C7 0.0626(10) 0.0429(9) 0.0571(11) 0.0038(8) 0.0000(8) 0.0074(8)
C6 0.0717(11) 0.0401(9) 0.0660(12) 0.0005(8) -0.0003(9) 0.0013(8)
C4 0.0780(12) 0.0444(10) 0.0639(12) 0.0062(9) -0.0030(9) 0.0113(8)
C11 0.0797(13) 0.0577(12) 0.0628(12) 0.0020(9) -0.0115(10) 0.0015(9)
C1 0.0978(16) 0.0752(15) 0.0768(14) 0.0021(12) -0.0256(12) 0.0202(11)
C2 0.0936(15) 0.0716(14) 0.0708(13) -0.0055(11) -0.0135(11) -0.0009(12)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N2 N3 114.71(15)
N2 C9 C8 122.00(16)
N2 C9 H9 119.0
C8 C9 H9 119.0
C10 O2 C11 116.70(13)
C10 N3 N2 119.44(14)
C10 N3 H3 120.3
N2 N3 H3 120.3
N1 C3 C4 121.92(16)
N1 C3 C5 121.59(16)
C4 C3 C5 116.49(16)
C6 C8 C7 116.64(16)
C6 C8 C9 120.04(16)
C7 C8 C9 123.32(16)
C7 C5 C3 121.32(16)
C7 C5 H5 119.3
C3 C5 H5 119.3
O1 C10 O2 124.50(16)
O1 C10 N3 126.45(16)
O2 C10 N3 109.03(14)
C3 N1 C2 122.56(16)
C3 N1 C1 120.36(17)
C2 N1 C1 116.83(17)
C5 C7 C8 121.95(16)
C5 C7 H7 119.0
C8 C7 H7 119.0
C4 C6 C8 122.19(17)
C4 C6 H6 118.9
C8 C6 H6 118.9
C6 C4 C3 121.41(16)
C6 C4 H4 119.3
C3 C4 H4 119.3
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N2 C9 1.282(2) no
N2 N3 1.386(2) no
C9 C8 1.454(2) ?
C9 H9 0.9300 ?
O2 C10 1.344(2) ?
O2 C11 1.436(2) ?
N3 C10 1.345(2) no
N3 H3 0.8600 ?
O1 C10 1.202(2) ?
C3 N1 1.376(2) ?
C3 C4 1.398(2) ?
C3 C5 1.413(2) ?
C8 C6 1.392(2) ?
C8 C7 1.395(2) ?
C5 C7 1.374(3) ?
C5 H5 0.9300 ?
N1 C2 1.434(3) ?
N1 C1 1.445(2) ?
C7 H7 0.9300 ?
C6 C4 1.377(3) ?
C6 H6 0.9300 ?
C4 H4 0.9300 ?
C11 H11A 0.9600 ?
C11 H11B 0.9600 ?
C11 H11C 0.9600 ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
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
_geom_hbond_publ_flag
N3 H3 O1 8_655 0.86 2.16 2.976(2) 157 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5268035
