#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/09/2200918.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_2200918
loop_
_publ_author_name
'Yu Zhang'
'Yizhi Li'
'Hanbin Tao'
'Longgen Zhu'
_publ_section_title
;
 4-(Antipyrin-4-yliminomethyl)benzoic acid
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o24
_journal_page_last               o26
_journal_paper_doi               10.1107/S1600536801020207
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C19 H17 N3 O3'
_chemical_formula_moiety         'C19 H17 N3 O3'
_chemical_formula_sum            'C19 H17 N3 O3'
_chemical_formula_weight         335.36
_chemical_name_systematic
;
 ?
;
_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                   13.0859(14)
_cell_length_b                   11.4837(13)
_cell_length_c                   22.422(2)
_cell_measurement_reflns_used    none
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      -28
_cell_measurement_theta_min      -28
_cell_volume                     3369.5(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'SMART APEX CCD'
_diffrn_measurement_method       'φ and w scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0859
_diffrn_reflns_av_sigmaI/netI    .0711
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16332
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    .092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .15
_refine_diff_density_max         .144
_refine_diff_density_min         -.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          .0889
_refine_ls_R_factor_gt           .0453
_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)+(0.0150P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .0714
_refine_ls_wR_factor_ref         .0764
_reflns_number_gt                1643
_reflns_number_total             2986
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6113.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               2200918
_cod_database_fobs_code          2200918
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_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 .33395(16) 1.06156(18) .23355(9) .0466(5) Uani d . 1 . . C
C2 .25674(17) .99866(19) .20789(10) .0634(7) Uani d . 1 . . C
H2 .2067 .9643 .2315 .076 Uiso calc R 1 . . H
C3 .2538(2) .9867(2) .14697(12) .0811(8) Uani d . 1 . . C
H3 .2014 .9444 .1291 .097 Uiso calc R 1 . . H
C4 .3276(2) 1.0368(2) .11269(11) .0802(8) Uani d . 1 . . C
H4 .3262 1.0273 .0715 .096 Uiso calc R 1 . . H
C5 .40325(19) 1.1005(2) .13826(11) .0786(8) Uani d . 1 . . C
H5 .4531 1.1349 .1145 .094 Uiso calc R 1 . . H
C6 .40653(16) 1.1143(2) .19937(10) .0633(7) Uani d . 1 . . C
H6 .4576 1.1590 .2170 .076 Uiso calc R 1 . . H
C7 .39880(16) .99487(18) .33258(9) .0436(5) Uani d . 1 . . C
C8 .35261(15) 1.00154(16) .38990(9) .0412(5) Uani d . 1 . . C
C9 .26972(15) 1.07502(18) .38594(9) .0456(6) Uani d . 1 . . C
C10 .45656(16) .88319(18) .44854(8) .0453(5) Uani d . 1 . . C
H10 .5025 .8769 .4171 .054 Uiso calc R 1 . . H
C11 .47756(16) .82356(17) .50478(8) .0429(5) Uani d . 1 . . C
C12 .56452(16) .75732(18) .51280(9) .0506(6) Uani d . 1 . . C
H12 .6110 .7500 .4817 .061 Uiso calc R 1 . . H
C13 .58365(15) .70187(17) .56612(9) .0502(6) Uani d . 1 . . C
H13 .6423 .6569 .5704 .060 Uiso calc R 1 . . H
C14 .51649(15) .71240(17) .61332(9) .0435(5) Uani d . 1 . . C
C15 .42974(16) .77912(18) .60565(9) .0586(7) Uani d . 1 . . C
H15 .3838 .7877 .6370 .070 Uiso calc R 1 . . H
C16 .41074(15) .83277(19) .55226(9) .0563(6) Uani d . 1 . . C
H16 .3514 .8765 .5478 .068 Uiso calc R 1 . . H
C17 .53889(18) .6524(2) .67018(9) .0502(6) Uani d . 1 . . C
C18 .19721(16) 1.2054(2) .30667(10) .0761(8) Uani d . 1 . . C
H18A .1499 1.2302 .3368 .114 Uiso calc R 1 . . H
H18B .1601 1.1765 .2728 .114 Uiso calc R 1 . . H
H18C .2388 1.2702 .2947 .114 Uiso calc R 1 . . H
C19 .19754(15) 1.1105(2) .43377(9) .0672(7) Uani d . 1 . . C
H19A .1939 1.1940 .4354 .101 Uiso calc R 1 . . H
H19B .2211 1.0811 .4714 .101 Uiso calc R 1 . . H
H19C .1310 1.0795 .4254 .101 Uiso calc R 1 . . H
N1 .34201(13) 1.06922(15) .29687(7) .0487(5) Uani d . 1 . . N
N2 .26160(12) 1.11428(15) .33023(8) .0493(5) Uani d . 1 . . N
N3 .37562(12) .94371(14) .44242(7) .0461(5) Uani d . 1 . . N
O1 .47157(11) .93502(12) .31377(5) .0534(4) Uani d . 1 . . O
O2 .61096(12) .58904(15) .67767(6) .0788(6) Uani d . 1 . . O
O3 .47082(10) .67435(12) .71210(6) .0590(4) Uani d . 1 . . O
H33 .4770 .6319 .7413 .071 Uiso d R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
_geom_angle_publ_flag
C6 C1 C2 120.8(2) y
C6 C1 N1 118.7(2) ?
C2 C1 N1 120.4(2) ?
C1 C2 C3 119.4(2) ?
C1 C2 H2 120.3 ?
C3 C2 H2 120.3 ?
C4 C3 C2 120.0(2) ?
C4 C3 H3 120.0 ?
C2 C3 H3 120.0 ?
C5 C4 C3 120.4(2) ?
C5 C4 H4 119.8 ?
C3 C4 H4 119.8 ?
C4 C5 C6 120.3(2) ?
C4 C5 H5 119.9 ?
C6 C5 H5 119.9 ?
C1 C6 C5 119.1(2) ?
C1 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
O1 C7 N1 123.57(18) y
O1 C7 C8 131.25(19) y
N1 C7 C8 105.13(18) y
C9 C8 N3 121.32(19) y
C9 C8 C7 108.03(18) y
N3 C8 C7 130.55(19) ?
N2 C9 C8 109.31(18) ?
N2 C9 C19 122.21(19) ?
C8 C9 C19 128.5(2) ?
N3 C10 C11 120.33(19) ?
N3 C10 H10 119.8 ?
C11 C10 H10 119.8 ?
C12 C11 C16 117.61(19) ?
C12 C11 C10 121.72(19) ?
C16 C11 C10 120.67(19) ?
C13 C12 C11 121.17(19) ?
C13 C12 H12 119.4 ?
C11 C12 H12 119.4 ?
C12 C13 C14 120.6(2) ?
C12 C13 H13 119.7 ?
C14 C13 H13 119.7 ?
C15 C14 C13 118.46(19) ?
C15 C14 C17 121.9(2) ?
C13 C14 C17 119.6(2) ?
C16 C15 C14 120.53(19) ?
C16 C15 H15 119.7 ?
C14 C15 H15 119.7 ?
C15 C16 C11 121.62(19) ?
C15 C16 H16 119.2 ?
C11 C16 H16 119.2 ?
O2 C17 O3 123.1(2) y
O2 C17 C14 123.9(2) y
O3 C17 C14 113.0(2) y
N2 C18 H18A 109.5 ?
N2 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
N2 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C9 C19 H19A 109.5 ?
C9 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C9 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C7 N1 N2 108.90(16) y
C7 N1 C1 125.21(18) ?
N2 N1 C1 120.15(16) ?
C9 N2 N1 108.54(16) ?
C9 N2 C18 129.42(19) ?
N1 N2 C18 120.96(17) ?
C10 N3 C8 122.26(18) ?
C17 O3 H33 112.8 ?
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 C6 . 1.362(3) y
C1 C2 . 1.369(3) ?
C1 N1 . 1.426(2) y
C2 C3 . 1.373(3) ?
C2 H2 . .9300 ?
C3 C4 . 1.362(3) ?
C3 H3 . .9300 ?
C4 C5 . 1.358(3) ?
C4 H4 . .9300 ?
C5 C6 . 1.380(3) ?
C5 H5 . .9300 ?
C6 H6 . .9300 ?
C7 O1 . 1.248(2) y
C7 N1 . 1.387(2) y
C7 C8 . 1.422(2) ?
C8 C9 . 1.377(2) ?
C8 N3 . 1.385(2) y
C9 N2 . 1.332(2) y
C9 C19 . 1.486(2) ?
C10 N3 . 1.274(2) y
C10 C11 . 1.461(2) y
C10 H10 . .9300 ?
C11 C12 . 1.381(2) y
C11 C16 . 1.382(2) ?
C12 C13 . 1.377(2) ?
C12 H12 . .9300 ?
C13 C14 . 1.381(2) ?
C13 H13 . .9300 ?
C14 C15 . 1.380(2) ?
C14 C17 . 1.479(3) y
C15 C16 . 1.369(2) ?
C15 H15 . .9300 ?
C16 H16 . .9300 ?
C17 O2 . 1.203(2) y
C17 O3 . 1.319(2) y
C18 N2 . 1.444(2) y
C18 H18A . .9600 ?
C18 H18B . .9600 ?
C18 H18C . .9600 ?
C19 H19A . .9600 ?
C19 H19B . .9600 ?
C19 H19C . .9600 ?
N1 N2 . 1.391(2) y
O3 H33 . .8202 ?
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
O3 H33 O1 7_576 .82 1.80 2.603(2) 166 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
C6 C1 C2 C3 1.3(4)
N1 C1 C2 C3 -176.2(2)
C1 C2 C3 C4 .3(4)
C2 C3 C4 C5 -1.2(4)
C3 C4 C5 C6 .5(4)
C2 C1 C6 C5 -2.0(3)
N1 C1 C6 C5 175.5(2)
C4 C5 C6 C1 1.1(4)
O1 C7 C8 C9 -175.5(2)
N1 C7 C8 C9 1.9(2)
O1 C7 C8 N3 .7(4)
N1 C7 C8 N3 178.12(18)
N3 C8 C9 N2 -176.71(17)
C7 C8 C9 N2 -.1(2)
N3 C8 C9 C19 3.9(3)
C7 C8 C9 C19 -179.5(2)
N3 C10 C11 C12 180.0(8)
N3 C10 C11 C16 -.7(3)
C16 C11 C12 C13 .4(3)
C10 C11 C12 C13 179.76(18)
C11 C12 C13 C14 -.8(3)
C12 C13 C14 C15 .4(3)
C12 C13 C14 C17 -179.78(18)
C13 C14 C15 C16 .4(3)
C17 C14 C15 C16 -179.42(19)
C14 C15 C16 C11 -.8(3)
C12 C11 C16 C15 .4(3)
C10 C11 C16 C15 -178.96(19)
C15 C14 C17 O2 176.3(2)
C13 C14 C17 O2 -3.6(3)
C15 C14 C17 O3 -3.1(3)
C13 C14 C17 O3 177.07(18)
O1 C7 N1 N2 174.70(18)
C8 C7 N1 N2 -3.0(2)
O1 C7 N1 C1 21.7(3)
C8 C7 N1 C1 -156.04(19)
C6 C1 N1 C7 -85.8(3)
C2 C1 N1 C7 91.8(3)
C6 C1 N1 N2 123.9(2)
C2 C1 N1 N2 -58.5(3)
C8 C9 N2 N1 -1.8(2)
C19 C9 N2 N1 177.67(18)
C8 C9 N2 C18 -169.8(2)
C19 C9 N2 C18 9.7(3)
C7 N1 N2 C9 3.1(2)
C1 N1 N2 C9 157.70(18)
C7 N1 N2 C18 172.25(17)
C1 N1 N2 C18 -33.1(3)
C11 C10 N3 C8 -179.91(17)
C9 C8 N3 C10 -173.96(19)
C7 C8 N3 C10 10.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654647
