#------------------------------------------------------------------------------
#$Date: 2019-11-28 17:33:14 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244193 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/84/7238492.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7238492
loop_
_publ_author_name
'Wang, Lei'
'Zhao, Lei'
'Xu, Lingyan'
'Chen, Ruixin'
'Yang, Yu'
_publ_section_title
;
 Interesting organic supramolecular structures constructed by
 piperazine/N,N′-dimethylpiperazine with aromatic multicomponent
 acids: synthon cooperation and structural diversity
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6998
_journal_paper_doi               10.1039/c2ce25627d
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C12 H4 N2 O5'
_chemical_formula_sum            'C12 H4 N2 O5'
_chemical_formula_weight         256.17
_chemical_melting_point          ?
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                 114.8030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0146(9)
_cell_length_b                   9.6205(7)
_cell_length_c                   11.9970(9)
_cell_measurement_temperature    293(2)
_cell_volume                     1258.78(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 12.00cm
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6817
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.0001
_exptl_absorpt_correction_T_min  0.0001
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0782
_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)+(0.1807P)²+1.2848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2502
_refine_ls_wR_factor_ref         0.2579
_reflns_number_gt                2178
_reflns_number_total             2456
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25627d.txt
_cod_data_source_block           w5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7238492
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O2 O 0.61688(17) 0.2217(2) 0.09929(18) 0.0366(6) Uani 1 1 d .
O4 O 0.08280(18) 0.0370(3) -0.28831(18) 0.0393(6) Uani 1 1 d .
O5 O 0.2983(2) 0.0739(3) 0.25502(18) 0.0409(6) Uani 1 1 d .
H5A H 0.3579 0.1116 0.3088 0.061 Uiso 1 1 calc R
O3 O -0.02416(18) 0.0971(3) -0.18444(19) 0.0438(7) Uani 1 1 d .
C2 C 0.7410(2) 0.1013(3) 0.3219(2) 0.0204(6) Uani 1 1 d .
H2A H 0.6794 0.1175 0.2392 0.024 Uiso 1 1 calc R
H2B H 0.8134 0.0642 0.3161 0.024 Uiso 1 1 calc R
C7 C 0.2978(2) 0.1403(3) -0.0861(2) 0.0258(6) Uani 1 1 d .
H7A H 0.2977 0.1515 -0.1632 0.031 Uiso 1 1 calc R
O1 O 0.4975(2) 0.2975(3) -0.0854(2) 0.0553(8) Uani 1 1 d .
C9 C 0.1919(2) 0.0774(3) 0.0386(2) 0.0267(6) Uani 1 1 d .
H9A H 0.1202 0.0517 0.0451 0.032 Uiso 1 1 calc R
C4 C 0.8073(2) 0.1141(3) 0.5819(2) 0.0211(6) Uani 1 1 d .
H4A H 0.8645 0.1006 0.6669 0.025 Uiso 1 1 calc R
H4B H 0.7316 0.1510 0.5806 0.025 Uiso 1 1 calc R
C11 C 0.4046(2) 0.1441(3) 0.1334(2) 0.0260(6) Uani 1 1 d .
H11A H 0.4762 0.1593 0.2039 0.031 Uiso 1 1 calc R
C12 C 0.0747(2) 0.0744(3) -0.1916(2) 0.0271(6) Uani 1 1 d .
C8 C 0.1917(2) 0.0957(3) -0.0762(2) 0.0238(6) Uani 1 1 d .
C10 C 0.2993(2) 0.0977(3) 0.1440(2) 0.0270(6) Uani 1 1 d .
C6 C 0.4037(2) 0.1679(3) 0.0190(2) 0.0248(6) Uani 1 1 d .
C5 C 0.5144(2) 0.2333(3) 0.0105(2) 0.0296(6) Uani 1 1 d .
N1 N 0.8595(3) 0.2147(3) 0.5223(3) 0.0453(7) Uani 1 1 d .
H1A H 0.9315 0.1822 0.5267 0.080 Uiso 1 1 calc .
H1B H 0.8736 0.2964 0.5623 0.080 Uiso 1 1 calc .
C3 C 0.7828(3) -0.0211(3) 0.5160(3) 0.0322(7) Uani 1 1 d .
H3A H 0.7492 -0.0862 0.5555 0.039 Uiso 1 1 calc R
H3B H 0.8590 -0.0594 0.5198 0.039 Uiso 1 1 calc R
N2 N 0.6937(3) -0.0024(3) 0.3838(3) 0.0427(7) Uani 1 1 d .
H2C H 0.6819 -0.0844 0.3443 0.080 Uiso 1 1 calc .
H2D H 0.6210 0.0265 0.3801 0.080 Uiso 1 1 calc .
C1 C 0.7726(3) 0.2362(3) 0.3901(3) 0.0328(7) Uani 1 1 d .
H5 H 0.6982 0.2800 0.3858 0.039 Uiso 1 1 calc R
H6 H 0.8099 0.2978 0.3515 0.039 Uiso 1 1 calc R
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
C10 O5 H5A 109.5
N2 C2 C1 111.8(2)
N2 C2 H2A 109.3
C1 C2 H2A 109.3
N2 C2 H2B 109.3
C1 C2 H2B 109.3
H2A C2 H2B 107.9
C6 C7 C8 120.1(2)
C6 C7 H7A 119.9
C8 C7 H7A 119.9
C8 C9 C10 119.9(2)
C8 C9 H9A 120.0
C10 C9 H9A 120.0
C3 C4 N1 110.0(2)
C3 C4 H4A 109.7
N1 C4 H4A 109.7
C3 C4 H4B 109.7
N1 C4 H4B 109.7
H4A C4 H4B 108.2
C6 C11 C10 120.7(2)
C6 C11 H11A 119.6
C10 C11 H11A 119.6
O3 C12 O4 124.0(2)
O3 C12 C8 117.3(2)
O4 C12 C8 118.7(2)
C9 C8 C7 120.1(2)
C9 C8 C12 120.3(2)
C7 C8 C12 119.5(2)
O5 C10 C9 118.8(2)
O5 C10 C11 121.6(2)
C9 C10 C11 119.5(2)
C11 C6 C7 119.4(2)
C11 C6 C5 119.5(2)
C7 C6 C5 120.9(2)
O1 C5 O2 123.5(3)
O1 C5 C6 117.5(2)
O2 C5 C6 119.0(2)
C4 N1 C1 110.5(2)
C4 N1 H1A 109.6
C1 N1 H1A 109.6
C4 N1 H1B 109.6
C1 N1 H1B 109.6
H1A N1 H1B 108.1
C4 C3 N2 110.5(2)
C4 C3 H3A 109.5
N2 C3 H3A 109.5
C4 C3 H3B 109.5
N2 C3 H3B 109.5
H3A C3 H3B 108.1
C2 N2 C3 110.7(2)
C2 N2 H2C 109.5
C3 N2 H2C 109.5
C2 N2 H2D 109.5
C3 N2 H2D 109.5
H2C N2 H2D 108.1
C2 C1 N1 111.2(2)
C2 C1 H5 109.4
N1 C1 H5 109.4
C2 C1 H6 109.4
N1 C1 H6 109.4
H5 C1 H6 108.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C5 1.250(3)
O4 C12 1.256(3)
O5 C10 1.357(3)
O5 H5A 0.8200
O3 C12 1.246(4)
C2 N2 1.491(4)
C2 C1 1.495(4)
C2 H2A 0.9700
C2 H2B 0.9700
C7 C6 1.391(4)
C7 C8 1.397(4)
C7 H7A 0.9300
O1 C5 1.246(4)
C9 C8 1.387(4)
C9 C10 1.390(4)
C9 H9A 0.9300
C4 C3 1.487(4)
C4 N1 1.489(4)
C4 H4A 0.9700
C4 H4B 0.9700
C11 C6 1.387(4)
C11 C10 1.397(4)
C11 H11A 0.9300
C12 C8 1.517(3)
C6 C5 1.513(4)
N1 C1 1.503(4)
N1 H1A 0.9000
N1 H1B 0.9000
C3 N2 1.506(4)
C3 H3A 0.9700
C3 H3B 0.9700
N2 H2C 0.9000
N2 H2D 0.9000
C1 H5 0.9700
C1 H6 0.9700
