#------------------------------------------------------------------------------
#$Date: 2019-11-10 04:15:41 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225611 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/50/7235007.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_7235007
loop_
_publ_author_name
'Bravo, Catarina'
'Galego, Filipa'
'Andre, Vania'
_publ_section_title
;
 Hydrogen bonding networks of Nalidixic acid-Copper(II) complexes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01057B
_journal_year                    2019
_chemical_formula_sum            'C12 H13 Cu0.5 N2 O4'
_chemical_formula_weight         281.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-07-05 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.821(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2633(5)
_cell_length_b                   7.4357(4)
_cell_length_c                   19.1577(12)
_cell_measurement_reflns_used    2663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.492
_cell_measurement_theta_min      2.501
_cell_volume                     1159.86(12)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_collection       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Mercury 4.1.3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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     0.71069
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17756
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.501
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             582
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0482P)²+1.6015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1905
_reflns_number_total             2663
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01057b2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C12 H13 Cu0.50 N2 O4'
_cod_database_code               7235007
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.795
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.8761(4) 0.4383(4) 0.63070(17) 0.0313(7) Uani 1 1 d . . .
C2 C 0.7189(3) 0.3695(4) 0.58831(16) 0.0272(6) Uani 1 1 d . . .
C3 C 0.6940(3) 0.3378(4) 0.51462(16) 0.0272(6) Uani 1 1 d . . .
C4 C 0.5361(3) 0.2628(4) 0.48353(16) 0.0270(6) Uani 1 1 d . . .
C5 C 0.4124(3) 0.2351(4) 0.52459(17) 0.0298(7) Uani 1 1 d . . .
C6 C 0.5923(4) 0.3376(4) 0.62485(17) 0.0341(7) Uani 1 1 d . . .
H6 H 0.6111 0.3604 0.6733 0.041 Uiso 1 1 calc R U .
C7 C 0.4981(4) 0.2168(4) 0.41222(18) 0.0350(7) Uani 1 1 d . . .
H7 H 0.5751 0.2339 0.3827 0.042 Uiso 1 1 calc R U .
C8 C 0.3469(4) 0.1461(5) 0.38561(19) 0.0392(8) Uani 1 1 d . . .
H8 H 0.3218 0.1115 0.3383 0.047 Uiso 1 1 calc R U .
C9 C 0.2303(4) 0.1265(4) 0.43053(19) 0.0349(7) Uani 1 1 d . . .
C10 C 0.3158(4) 0.2553(9) 0.6413(2) 0.0759(16) Uani 1 1 d . . .
H10A H 0.2861 0.3747 0.6552 0.091 Uiso 1 1 calc R U .
H10B H 0.2191 0.2042 0.6123 0.091 Uiso 1 1 calc R U .
C11 C 0.3508(6) 0.1550(10) 0.7005(3) 0.111(3) Uani 1 1 d . . .
H11A H 0.2576 0.1534 0.7244 0.167 Uiso 1 1 calc R U .
H11B H 0.3762 0.0345 0.6881 0.167 Uiso 1 1 calc R U .
H11C H 0.4435 0.2057 0.7313 0.167 Uiso 1 1 calc R U .
C12 C 0.0628(4) 0.0529(5) 0.4030(2) 0.0482(10) Uani 1 1 d . . .
H12A H 0.0544 0.0251 0.3536 0.072 Uiso 1 1 calc R U .
H12B H 0.0454 -0.0544 0.4286 0.072 Uiso 1 1 calc R U .
H12C H -0.0187 0.1408 0.4092 0.072 Uiso 1 1 calc R U .
Cu01 Cu 1.0000 0.5000 0.5000 0.03135(18) Uani 1 2 d S . P
N1 N 0.4444(3) 0.2762(4) 0.59580(14) 0.0373(7) Uani 1 1 d . . .
N2 N 0.2616(3) 0.1717(4) 0.49845(15) 0.0363(6) Uani 1 1 d . . .
O1 O 0.7975(3) 0.3696(3) 0.47396(12) 0.0365(5) Uani 1 1 d . . .
O2 O 0.9877(3) 0.4966(3) 0.59764(12) 0.0361(5) Uani 1 1 d . . .
O1W O 0.7738(4) 0.1646(6) 0.7783(3) 0.1092(17) Uani 1 1 d D . .
O3 O 0.8936(3) 0.4381(4) 0.69521(13) 0.0505(7) Uani 1 1 d . . .
H3W H 0.842(6) 0.092(4) 0.758(3) 0.076 Uiso 1 1 d D U .
H4W H 0.817(5) 0.272(3) 0.765(2) 0.076 Uiso 1 1 d D U .
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'
Cu Cu 0.3201 1.2651 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 C1 O2 122.0(3) . .
O3 C1 C2 119.4(3) . .
O2 C1 C2 118.6(3) . .
C6 C2 C3 119.1(3) . .
C6 C2 C1 116.6(3) . .
C3 C2 C1 124.3(3) . .
O1 C3 C2 125.6(3) . .
O1 C3 C4 118.1(3) . .
C2 C3 C4 116.3(2) . .
C7 C4 C5 116.7(3) . .
C7 C4 C3 122.3(3) . .
C5 C4 C3 121.0(3) . .
N2 C5 N1 117.0(3) . .
N2 C5 C4 123.9(3) . .
N1 C5 C4 119.0(3) . .
N1 C6 C2 124.7(3) . .
N1 C6 H6 117.7 . .
C2 C6 H6 117.7 . .
C8 C7 C4 119.9(3) . .
C8 C7 H7 120.1 . .
C4 C7 H7 120.1 . .
C7 C8 C9 119.2(3) . .
C7 C8 H8 120.4 . .
C9 C8 H8 120.4 . .
N2 C9 C8 122.4(3) . .
N2 C9 C12 116.9(3) . .
C8 C9 C12 120.7(3) . .
C11 C10 N1 118.5(4) . .
C11 C10 H10A 107.7 . .
N1 C10 H10A 107.7 . .
C11 C10 H10B 107.7 . .
N1 C10 H10B 107.7 . .
H10A C10 H10B 107.1 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O2 Cu01 O2 180.0 3_766 .
O2 Cu01 O1 93.36(9) 3_766 3_766
O2 Cu01 O1 86.64(9) . 3_766
O2 Cu01 O1 86.64(9) 3_766 .
O2 Cu01 O1 93.36(9) . .
O1 Cu01 O1 180.0 3_766 .
C6 N1 C5 119.7(3) . .
C6 N1 C10 119.0(3) . .
C5 N1 C10 121.3(3) . .
C9 N2 C5 117.8(3) . .
C3 O1 Cu01 125.5(2) . .
C1 O2 Cu01 131.2(2) . .
H3W O1W H4W 95(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O3 1.220(4) .
C1 O2 1.280(4) .
C1 C2 1.499(4) .
C2 C6 1.375(4) .
C2 C3 1.411(4) .
C3 O1 1.273(3) .
C3 C4 1.450(4) .
C4 C7 1.391(4) .
C4 C5 1.408(4) .
C5 N2 1.346(4) .
C5 N1 1.379(4) .
C6 N1 1.334(4) .
C6 H6 0.9300 .
C7 C8 1.371(4) .
C7 H7 0.9300 .
C8 C9 1.405(5) .
C8 H8 0.9300 .
C9 N2 1.326(4) .
C9 C12 1.498(4) .
C10 C11 1.347(6) .
C10 N1 1.493(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
Cu01 O2 1.891(2) 3_766
Cu01 O2 1.891(2) .
Cu01 O1 1.925(2) 3_766
Cu01 O1 1.925(2) .
O1W H3W 0.918(18) .
O1W H4W 0.925(19) .
