#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:03:54 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228999 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/03/7230376.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_7230376
loop_
_publ_author_name
'Carballo, Rosa'
'Castiñeiras, Alfonso'
'Covelo, Berta'
'Lago, Ana B.'
'Vázquez-López, Ezequiel M.'
'Gómez-Paz, Olaya'
'Balboa, Susana'
'Prieto, Inmaculada'
_publ_section_title
;
 Chiral and achiral 1D copper(ii) coordination polymers based on glycolato
 and chelating aromatic diamine ligands
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2455
_journal_paper_doi               10.1039/C8CE00279G
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C12 H13 Cu N3 O4'
_chemical_formula_weight         326.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-02-19 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.0214(12)
_cell_length_b                   18.010(3)
_cell_length_c                   19.735(3)
_cell_measurement_reflns_used    942
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.49
_cell_volume                     2495.6(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13769
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.025
_diffrn_reflns_theta_min         2.064
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_T_max  0.588
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0361P)²+1.7530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2480
_reflns_number_total             2967
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00279g1.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 7230374--7230379.cif.'
_cod_original_cell_volume        2495.7(7)
_cod_database_code               7230376
_shelx_shelxl_version_number     2016/6
_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. 
;
loop_
_space_group_symop_operation_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_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
Cu Cu 0.06289(5) 0.18326(2) 0.36018(2) 0.02522(11) Uani 1 1 d . .
O11 O -0.0246(3) 0.19341(10) 0.26609(10) 0.0371(5) Uani 1 1 d . .
O12 O -0.1505(3) 0.12587(11) 0.18292(9) 0.0354(5) Uani 1 1 d . .
O13 O -0.0697(3) 0.09093(11) 0.35942(9) 0.0317(4) Uani 1 1 d . .
C11 C -0.0977(4) 0.13416(15) 0.24285(14) 0.0277(6) Uani 1 1 d . .
C12 C -0.1172(4) 0.07013(15) 0.29313(14) 0.0304(6) Uani 1 1 d . .
H12A H -0.247386 0.052167 0.292426 0.036 Uiso 1 1 calc R U
H12B H -0.034969 0.029697 0.279031 0.036 Uiso 1 1 calc R U
N1 N 0.1491(3) 0.28823(12) 0.36161(10) 0.0257(5) Uani 1 1 d . .
N3 N 0.0916(3) 0.30398(13) 0.47869(12) 0.0287(5) Uani 1 1 d . .
N2 N 0.1139(3) 0.17473(12) 0.45916(11) 0.0270(5) Uani 1 1 d . .
C1 C 0.2047(4) 0.31986(15) 0.30202(13) 0.0313(6) Uani 1 1 d . .
H1 H 0.222142 0.289242 0.264588 0.038 Uiso 1 1 calc R U
C2 C 0.2359(5) 0.39413(15) 0.29461(14) 0.0344(7) Uani 1 1 d . .
H2 H 0.277461 0.413289 0.253424 0.041 Uiso 1 1 calc R U
C3 C 0.2044(5) 0.44088(15) 0.34976(14) 0.0351(7) Uani 1 1 d . .
H3 H 0.219101 0.491975 0.345373 0.042 Uiso 1 1 calc R U
C4 C 0.1516(4) 0.41051(14) 0.41045(14) 0.0332(6) Uani 1 1 d . .
H4 H 0.129474 0.440752 0.447824 0.040 Uiso 1 1 calc R U
C5 C 0.1310(4) 0.33296(14) 0.41572(13) 0.0248(5) Uani 1 1 d . .
C6 C 0.1076(4) 0.23236(14) 0.50254(13) 0.0248(5) Uani 1 1 d . .
C7 C 0.1148(4) 0.22168(17) 0.57268(14) 0.0339(7) Uani 1 1 d . .
H7 H 0.104591 0.261916 0.601989 0.041 Uiso 1 1 calc R U
C8 C 0.1371(5) 0.15144(18) 0.59767(15) 0.0401(7) Uani 1 1 d . .
H8 H 0.142642 0.143536 0.644197 0.048 Uiso 1 1 calc R U
C9 C 0.1514(5) 0.09165(17) 0.55297(15) 0.0401(7) Uani 1 1 d . .
H9 H 0.170130 0.043654 0.569024 0.048 Uiso 1 1 calc R U
C10 C 0.1372(4) 0.10526(16) 0.48537(15) 0.0349(7) Uani 1 1 d . .
H10 H 0.143658 0.065301 0.455616 0.042 Uiso 1 1 calc R U
O1W O 0.5986(4) 0.08678(14) 0.42301(11) 0.0394(5) Uani 1 1 d . .
H1B H 0.698(6) 0.087(2) 0.4069(19) 0.051(12) Uiso 1 1 d . .
H3B H 0.088(4) 0.3319(17) 0.5083(17) 0.032(9) Uiso 1 1 d . .
H1A H 0.524(6) 0.094(2) 0.396(2) 0.049(12) Uiso 1 1 d . .
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'
Cu Cu 0.3201 1.2651 '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_3
O13 Cu O11 85.47(8) .
O13 Cu N1 168.51(9) .
O11 Cu N1 91.16(8) .
O13 Cu N2 91.61(8) .
O11 Cu N2 172.05(9) .
N1 Cu N2 90.27(9) .
O13 Cu O12 91.76(8) 6_656
O11 Cu O12 88.14(8) 6_656
N1 Cu O12 99.12(8) 6_656
N2 Cu O12 99.35(8) 6_656
C11 O11 Cu 112.93(17) .
C11 O12 Cu 121.97(17) 6_556
C12 O13 Cu 110.91(16) .
O12 C11 O11 124.2(3) .
O12 C11 C12 119.9(2) .
O11 C11 C12 115.8(2) .
O13 C12 C11 112.5(2) .
C5 N1 C1 117.5(2) .
C5 N1 Cu 123.61(18) .
C1 N1 Cu 118.21(17) .
C5 N3 C6 130.3(2) .
C6 N2 C10 118.0(2) .
C6 N2 Cu 123.93(18) .
C10 N2 Cu 117.67(19) .
C2 C1 N1 123.3(3) .
C1 C2 C3 118.9(3) .
C4 C3 C2 119.0(2) .
C3 C4 C5 119.3(2) .
N1 C5 N3 120.6(2) .
N1 C5 C4 121.8(2) .
N3 C5 C4 117.6(2) .
N2 C6 N3 120.5(2) .
N2 C6 C7 121.5(2) .
N3 C6 C7 118.0(2) .
C8 C7 C6 119.3(3) .
C7 C8 C9 119.6(3) .
C10 C9 C8 118.4(3) .
C9 C10 N2 123.1(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu O13 1.9058(19) .
Cu O11 1.964(2) .
Cu N1 1.985(2) .
Cu N2 1.992(2) .
Cu O12 2.417(2) 6_656
O11 C11 1.270(3) .
O12 C11 1.248(3) .
O13 C12 1.401(3) .
C11 C12 1.528(4) .
N1 C5 1.344(3) .
N1 C1 1.364(3) .
N3 C5 1.376(3) .
N3 C6 1.378(3) .
N2 C6 1.346(3) .
N2 C10 1.364(3) .
C1 C2 1.363(4) .
C2 C3 1.394(4) .
C3 C4 1.368(4) .
C4 C5 1.408(4) .
C6 C7 1.399(4) .
C7 C8 1.367(4) .
C8 C9 1.396(4) .
C9 C10 1.360(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O13 0.93 2.46 2.890(3) 108.2 .
C3 H3 O12 0.93 2.52 3.415(3) 161.0 3
C1 H1 O11 0.93 2.55 3.257(4) 133.0 6_656
C1 H1 O11 0.93 2.45 2.878(3) 108.4 .
O1W H1A O12 0.76(4) 2.07(4) 2.815(3) 171(4) 6_656
N3 H3B O1W 0.77(3) 2.00(3) 2.764(3) 172(3) 4_456
O1W H1B O13 0.77(4) 1.88(4) 2.647(3) 174(4) 1_655
