#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/34/2233472.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_2233472
loop_
_publ_author_name
'Wang, Dong-Yue'
'Liu, Min'
'Ma, Jing-Jun'
_publ_section_title
;
 2-[(5-Chloro-2-oxidobenzylidene)azaniumyl]-2-methylpropane-1,3-diol
;
_journal_coeditor_code           HB6578
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o295
_journal_paper_doi               10.1107/S1600536811055784
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C11 H14 Cl N O3'
_chemical_formula_moiety         'C11 H14 Cl N O3'
_chemical_formula_sum            'C11 H14 Cl N O3'
_chemical_formula_weight         243.68
_chemical_name_systematic
;
2-[(5-Chloro-2-oxidobenzylidene)azaniumyl]-2-methylpropane-1,3-diol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.0019(16)
_cell_length_b                   8.838(3)
_cell_length_c                   21.555(3)
_cell_measurement_reflns_used    1733
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.15
_cell_measurement_theta_min      2.49
_cell_volume                     1143.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       'ω scan'
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5744
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.9589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.151
_refine_ls_abs_structure_details 'Flack (1983), 842 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.06(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0389
_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)+(0.0287P)²+0.1130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                1745
_reflns_number_total             2105
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6578.cif
_cod_data_source_block           I
_cod_database_code               2233472
_cod_database_fobs_code          2233472
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'
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
_atom_site_symmetry_multiplicity
Cl Cl1 0.67835(15) -0.07637(8) -0.02077(3) 0.0613(2) Uani d . 1 1
N N1 0.8677(3) 0.4851(2) 0.15414(9) 0.0356(5) Uani d D 1 1
O O1 1.2095(3) 0.30421(19) 0.14623(7) 0.0422(4) Uani d . 1 1
O O3 0.5214(3) 0.6832(2) 0.27003(8) 0.0462(5) Uani d D 1 1
O O4 1.0926(3) 0.6167(2) 0.24842(11) 0.0609(6) Uani d D 1 1
C C1 1.0897(4) 0.2197(3) 0.11037(11) 0.0350(6) Uani d . 1 1
C C2 1.1701(5) 0.0789(3) 0.08645(11) 0.0442(6) Uani d . 1 1
H H2 1.3107 0.0449 0.0981 0.053 Uiso calc R 1 1
C C3 1.0452(5) -0.0064(3) 0.04693(12) 0.0470(7) Uani d . 1 1
H H3 1.1032 -0.0965 0.0316 0.056 Uiso calc R 1 1
C C4 0.8320(5) 0.0388(3) 0.02898(11) 0.0412(6) Uani d . 1 1
C C5 0.7447(4) 0.1709(3) 0.05062(10) 0.0366(6) Uani d . 1 1
H H5 0.6031 0.2012 0.0383 0.044 Uiso calc R 1 1
C C6 0.8698(4) 0.2620(3) 0.09192(10) 0.0315(5) Uani d . 1 1
C C7 0.7671(4) 0.3945(3) 0.11616(10) 0.0352(6) Uani d . 1 1
H H7 0.6219 0.4170 0.1042 0.042 Uiso calc R 1 1
C C8 0.7731(4) 0.6211(3) 0.18423(10) 0.0350(6) Uani d . 1 1
C C9 0.6345(6) 0.7147(3) 0.13884(12) 0.0603(8) Uani d . 1 1
H H9A 0.7202 0.7341 0.1021 0.090 Uiso calc R 1 1
H H9B 0.5940 0.8089 0.1579 0.090 Uiso calc R 1 1
H H9C 0.5020 0.6598 0.1280 0.090 Uiso calc R 1 1
C C10 0.6293(4) 0.5634(3) 0.23840(11) 0.0384(6) Uani d . 1 1
H H10A 0.5181 0.4938 0.2226 0.046 Uiso calc R 1 1
H H10B 0.7229 0.5085 0.2674 0.046 Uiso calc R 1 1
C C11 0.9699(4) 0.7115(3) 0.20833(12) 0.0462(7) Uani d . 1 1
H H11A 1.0627 0.7446 0.1741 0.055 Uiso calc R 1 1
H H11B 0.9180 0.8002 0.2306 0.055 Uiso calc R 1 1
H H3A 0.603(4) 0.720(3) 0.2983(10) 0.069 Uiso d D 1 1
H H4 1.215(3) 0.651(3) 0.2621(12) 0.069 Uiso d D 1 1
H H1 1.005(2) 0.452(3) 0.1646(11) 0.055 Uiso d D 1 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
C7 N1 C8 126.9(2)
C7 N1 H1 112.7(17)
C8 N1 H1 120.1(17)
C10 O3 H3A 112(2)
C11 O4 H4 117(2)
O1 C1 C6 121.9(2)
O1 C1 C2 122.0(2)
C6 C1 C2 116.1(2)
C3 C2 C1 121.4(2)
C3 C2 H2 119.3
C1 C2 H2 119.3
C2 C3 C4 121.3(2)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 120.2(2)
C5 C4 Cl1 120.5(2)
C3 C4 Cl1 119.27(19)
C4 C5 C6 119.9(2)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C7 118.0(2)
C5 C6 C1 121.1(2)
C7 C6 C1 120.9(2)
N1 C7 C6 122.6(2)
N1 C7 H7 118.7
C6 C7 H7 118.7
N1 C8 C11 106.2(2)
N1 C8 C9 111.61(19)
C11 C8 C9 111.0(2)
N1 C8 C10 106.20(18)
C11 C8 C10 110.55(19)
C9 C8 C10 111.1(2)
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O3 C10 C8 111.98(19)
O3 C10 H10A 109.2
C8 C10 H10A 109.2
O3 C10 H10B 109.2
C8 C10 H10B 109.2
H10A C10 H10B 107.9
O4 C11 C8 107.65(19)
O4 C11 H11A 110.2
C8 C11 H11A 110.2
O4 C11 H11B 110.2
C8 C11 H11B 110.2
H11A C11 H11B 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.743(2)
N1 C7 1.294(3)
N1 C8 1.479(3)
N1 H1 0.903(10)
O1 C1 1.293(3)
O3 C10 1.416(3)
O3 H3A 0.847(10)
O4 C11 1.411(3)
O4 H4 0.847(10)
C1 C6 1.428(3)
C1 C2 1.431(3)
C2 C3 1.362(3)
C2 H2 0.9300
C3 C4 1.395(4)
C3 H3 0.9300
C4 C5 1.362(3)
C5 C6 1.416(3)
C5 H5 0.9300
C6 C7 1.423(3)
C7 H7 0.9300
C8 C11 1.517(3)
C8 C9 1.528(3)
C8 C10 1.539(3)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
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
N1 H1 O1 . 0.903(10) 1.837(18) 2.606(3) 142(2)
O4 H4 O3 1_655 0.847(10) 1.870(14) 2.680(2) 160(3)
O3 H3A O1 3_755 0.847(10) 1.802(11) 2.648(2) 176(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657411
