#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/09/2010941.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_2010941
loop_
_publ_author_name
'Billington, David C.'
'Lowe, Philip R.'
'Rathbone, Daniel L.'
'Schwalbe, Carl H.'
_publ_section_title
;
 A new amidrazone derivative with antimycobacterial activity
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e211
_journal_page_last               e212
_journal_paper_doi               10.1107/S0108270100004807
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C18 H22 N4'
_chemical_formula_weight         294.40
_chemical_melting_point          360.5(11)
_chemical_name_systematic
;
N'-(4-(1,1-dimethylpropyl)-benzylidene)-2-pyridinecarboxamidrazone
;
_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'
_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                   21.957(4)
_cell_length_b                   20.518(2)
_cell_length_c                   7.5220(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      8.64
_cell_volume                     3388.8(8)
_computing_cell_refinement       'CAD-4 Foftware'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'CADABS (Gould & Smith, 1986)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .994
_diffrn_measured_fraction_theta_max .994
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  .072
_diffrn_reflns_av_sigmaI/netI    .0733
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6157
_diffrn_reflns_theta_full        72.06
_diffrn_reflns_theta_max         72.07
_diffrn_reflns_theta_min         4.03
_diffrn_standards_decay_%        3.1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .549
_exptl_absorpt_correction_T_max  .921
_exptl_absorpt_correction_T_min  .469
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(CADABS; Gould & Smith, 1986)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          .65
_exptl_crystal_size_mid          .33
_exptl_crystal_size_min          .15
_refine_diff_density_max         .372
_refine_diff_density_min         -.246
_refine_ls_extinction_coef       .0011(3)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          .153
_refine_ls_R_factor_gt           .072
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.1267P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .231
_reflns_number_gt                1635
_reflns_number_total             3316
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0258.cif
_cod_data_source_block           I
_cod_depositor_comments
;
'_chemical_melting_point' value '86.3 - 88.4\% corrected' was changed to
'360.5(11)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Adriana Da\<skevi\<c, 2007-06-07
;
_cod_database_code               2010941
_cod_database_fobs_code          2010941
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .83084(14) .86269(14) .8422(4) .0530(8) Uani d . 1 . . C
C2 .83927(15) .81339(16) .9658(5) .0632(9) Uani d . 1 . . C
H2 .8174 .7748 .9543 .076 Uiso calc R 1 . . H
C3 .87930(15) .82041(17) 1.1052(5) .0683(9) Uani d . 1 . . C
H3 .8836 .7863 1.1858 .082 Uiso calc R 1 . . H
C4 .91333(16) .87617(16) 1.1296(5) .0650(9) Uani d . 1 . . C
C5 .90318(17) .92599(17) 1.0086(5) .0726(10) Uani d . 1 . . C
H5 .9237 .9652 1.0235 .087 Uiso calc R 1 . . H
C6 .86411(15) .91955(17) .8684(5) .0643(9) Uani d . 1 . . C
H6 .8597 .9539 .7888 .077 Uiso calc R 1 . . H
C11 .79085(14) .85122(15) .6927(4) .0567(8) Uani d . 1 . . C
H11 .7729 .8103 .6827 .068 Uiso calc R 1 . . H
N12 .77841(12) .89370(12) .5727(4) .0566(7) Uani d . 1 . . N
N13 .74264(12) .86728(12) .4377(4) .0576(7) Uani d . 1 . . N
C14 .73423(13) .90759(14) .3061(4) .0492(7) Uani d . 1 . . C
N141 .75509(13) .96872(12) .2965(4) .0641(8) Uani d . 1 . . N
H141 .7762 .9846 .3825 .077 Uiso calc R 1 . . H
H142 .7474 .9921 .2044 .077 Uiso calc R 1 . . H
C1P .69906(12) .88248(13) .1540(4) .0478(7) Uani d . 1 . . C
N2P .68382(12) .92546(12) .0268(3) .0567(7) Uani d . 1 . . N
C3P .65236(16) .90296(18) -.1108(5) .0693(10) Uani d . 1 . . C
H3P .6421 .9321 -.2006 .083 Uiso calc R 1 . . H
C4P .63403(17) .8394(2) -.1288(5) .0757(11) Uani d . 1 . . C
H4P .6112 .8260 -.2264 .091 Uiso calc R 1 . . H
C5P .65041(19) .79634(19) .0010(5) .0792(11) Uani d . 1 . . C
H5P .6391 .7528 -.0076 .095 Uiso calc R 1 . . H
C6P .68324(15) .81746(15) .1427(5) .0622(9) Uani d . 1 . . C
H6P .6950 .7884 .2313 .075 Uiso calc R 1 . . H
C41 .95916(17) .8845(2) 1.2811(5) .0805(11) Uani d D 1 A . C
C411 .9368(3) .9445(4) 1.4028(9) .092(3) Uiso d PD .703(14) . . C
H41A .9398 .9843 1.3363 .137 Uiso calc PR .703(14) . . H
H41B .9620 .9473 1.5067 .137 Uiso calc PR .703(14) . . H
H41C .8953 .9375 1.4379 .137 Uiso calc PR .703(14) . . H
C412 .9332(9) .8960(13) 1.451(2) .124(9) Uiso d PD .297(14) . . C
H41D .9047 .9314 1.4435 .186 Uiso calc PR .297(14) . . H
H41E .9648 .9069 1.5341 .186 Uiso calc PR .297(14) . . H
H41F .9124 .8575 1.4908 .186 Uiso calc PR .297(14) . . H
C413 .9566(4) .8314(4) 1.4198(12) .087(3) Uiso d PD .578(17) . . C
H41G .9157 .8273 1.4633 .130 Uiso calc PR .578(17) . . H
H41H .9833 .8423 1.5165 .130 Uiso calc PR .578(17) . . H
H41I .9693 .7909 1.3678 .130 Uiso calc PR .578(17) . . H
C414 .9846(8) .8132(6) 1.338(3) .130(6) Uiso d PD .422(17) . . C
H41J .9521 .7880 1.3886 .195 Uiso calc PR .422(17) . . H
H41K 1.0167 .8181 1.4235 .195 Uiso calc PR .422(17) . . H
H41L 1.0001 .7912 1.2345 .195 Uiso calc PR .422(17) . . H
C42 1.01975(18) .9067(3) 1.2154(6) .0992(14) Uani d D 1 . . C
H42A 1.0477 .9143 1.3131 .119 Uiso calc PR .542(19) A 1 H
H42B 1.0161 .9463 1.1456 .119 Uiso calc PR .542(19) A 1 H
H42C 1.0473 .9012 1.3150 .119 Uiso calc PR .458(19) A 2 H
H42D 1.0157 .9534 1.1982 .119 Uiso calc PR .458(19) A 2 H
C431 1.0414(5) .8479(8) 1.0970(17) .117(4) Uiso d PD .542(19) A 1 C
H43A 1.0812 .8570 1.0501 .175 Uiso calc PR .542(19) A 1 H
H43B 1.0133 .8417 1.0007 .175 Uiso calc PR .542(19) A 1 H
H43C 1.0430 .8090 1.1679 .175 Uiso calc PR .542(19) A 1 H
C432 1.0542(4) .8827(7) 1.0561(13) .083(4) Uiso d PD .458(19) A 2 C
H43D 1.0919 .9061 1.0460 .125 Uiso calc PR .458(19) A 2 H
H43E 1.0302 .8896 .9510 .125 Uiso calc PR .458(19) A 2 H
H43F 1.0624 .8370 1.0695 .125 Uiso calc PR .458(19) A 2 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 '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_publ_flag
C2 C1 C6 116.5(3) ?
C2 C1 C11 119.0(3) ?
C6 C1 C11 124.5(3) ?
C3 C2 C1 121.3(3) ?
C2 C3 C4 122.3(3) ?
C3 C4 C5 115.9(3) ?
C3 C4 C41 123.2(3) ?
C5 C4 C41 120.8(3) ?
C6 C5 C4 122.4(3) ?
C5 C6 C1 121.4(3) ?
N12 C11 C1 124.4(3) ?
C11 N12 N13 111.6(3) ?
C14 N13 N12 112.7(2) ?
N13 C14 N141 126.0(3) yes
N13 C14 C1P 116.2(3) yes
N141 C14 C1P 117.8(3) yes
N2P C1P C6P 121.8(3) ?
N2P C1P C14 117.0(3) ?
C6P C1P C14 121.2(3) ?
C3P N2P C1P 117.2(3) ?
N2P C3P C4P 124.1(3) ?
C5P C4P C3P 117.9(4) ?
C6P C5P C4P 119.7(3) ?
C5P C6P C1P 119.3(3) ?
C412 C41 C42 127.3(10) ?
C412 C41 C413 58.9(12) ?
C42 C41 C413 118.9(5) ?
C412 C41 C4 115.2(9) ?
C42 C41 C4 112.0(3) ?
C413 C41 C4 114.2(4) ?
C412 C41 C411 40.4(10) ?
C42 C41 C411 103.1(4) ?
C413 C41 C411 98.5(5) ?
C4 C41 C411 108.0(4) ?
C412 C41 C414 93.0(14) ?
C42 C41 C414 93.2(8) ?
C413 C41 C414 35.0(6) ?
C4 C41 C414 108.7(6) ?
C411 C41 C414 130.1(9) ?
C41 C42 C432 127.9(6) ?
C41 C42 C431 102.9(7) ?
C432 C42 C431 31.1(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.387(4) ?
C1 C6 . 1.391(4) ?
C1 C11 . 1.446(4) yes
C2 C3 . 1.376(5) ?
C3 C4 . 1.379(5) ?
C4 C5 . 1.387(5) ?
C4 C41 . 1.530(5) ?
C5 C6 . 1.366(5) ?
C11 N12 . 1.284(4) yes
N12 N13 . 1.393(4) yes
N13 C14 . 1.303(4) yes
C14 N141 . 1.337(4) yes
C14 C1P . 1.473(4) yes
C1P N2P . 1.344(4) yes
C1P C6P . 1.381(4) ?
N2P C3P . 1.327(4) yes
C3P C4P . 1.372(5) ?
C4P C5P . 1.365(5) ?
C5P C6P . 1.358(5) ?
C41 C412 . 1.421(15) ?
C41 C42 . 1.491(5) ?
C41 C413 . 1.510(8) ?
C41 C411 . 1.610(7) ?
C41 C414 . 1.624(12) ?
C42 C432 . 1.500(9) ?
C42 C431 . 1.574(10) ?
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
N141 H141 N12 . .86 2.35 2.636(4) 100 yes
N141 H142 N2P . .86 2.37 2.712(4) 104 yes
N141 H141 N2P 4_675 .86 2.31 3.085(4) 149 yes
N141 H142 N12 4_674 .86 2.61 3.368(4) 148 yes
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.0(5) ?
C11 C1 C2 C3 176.4(3) ?
C1 C2 C3 C4 -.3(6) ?
C2 C3 C4 C5 2.3(6) ?
C2 C3 C4 C41 -178.6(3) ?
C3 C4 C5 C6 -3.0(6) ?
C41 C4 C5 C6 177.8(3) ?
C4 C5 C6 C1 1.8(6) ?
C2 C1 C6 C5 .3(5) ?
C11 C1 C6 C5 -177.0(3) ?
C2 C1 C11 N12 178.1(3) yes
C6 C1 C11 N12 -4.6(5) ?
C1 C11 N12 N13 175.1(3) yes
C11 N12 N13 C14 -173.9(3) yes
N12 N13 C14 N141 -1.7(4) ?
N12 N13 C14 C1P 177.4(2) yes
N13 C14 C1P N2P 172.4(3) yes
N141 C14 C1P N2P -8.3(4) ?
N13 C14 C1P C6P -8.3(4) ?
N141 C14 C1P C6P 170.9(3) ?
C6P C1P N2P C3P .4(5) ?
C14 C1P N2P C3P 179.7(3) ?
C1P N2P C3P C4P 1.0(5) ?
N2P C3P C4P C5P -1.6(6) ?
C3P C4P C5P C6P .7(6) ?
C4P C5P C6P C1P .6(6) ?
N2P C1P C6P C5P -1.2(5) ?
C14 C1P C6P C5P 179.5(3) ?
C3 C4 C41 C412 -75.2(13) ?
C5 C4 C41 C412 103.9(13) ?
C3 C4 C41 C42 129.0(4) ?
C5 C4 C41 C42 -51.9(5) ?
C3 C4 C41 C413 -9.8(7) ?
C5 C4 C41 C413 169.3(6) ?
C3 C4 C41 C411 -118.2(5) ?
C5 C4 C41 C411 60.9(5) ?
C3 C4 C41 C414 27.5(9) ?
C5 C4 C41 C414 -153.4(9) ?
C412 C41 C42 C432 164.2(15) ?
C413 C41 C42 C432 93.0(9) ?
C4 C41 C42 C432 -43.6(8) ?
C411 C41 C42 C432 -159.4(8) ?
C414 C41 C42 C432 68.0(10) ?
C412 C41 C42 C431 143.5(15) ?
C413 C41 C42 C431 72.3(8) ?
C4 C41 C42 C431 -64.3(6) ?
C411 C41 C42 C431 179.9(6) ?
C414 C41 C42 C431 47.3(9) ?
