#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:03:54 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228999 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/03/7230374.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_7230374
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            'C14 H11 Cl Cu N2 O7'
_chemical_formula_weight         418.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.4852(2)
_cell_length_b                   14.3549(4)
_cell_length_c                   15.7193(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.29
_cell_measurement_theta_min      18.90
_cell_volume                     1463.38(12)
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_collection       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        'GENHKL (Kretschmar, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       omega/2theta-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3279
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         72.957
_diffrn_reflns_theta_min         4.171
_exptl_absorpt_coefficient_mu    4.223
_exptl_absorpt_correction_T_max  0.509
_exptl_absorpt_correction_T_min  0.341
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_description       prism
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1033P)²+1.2250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2799
_reflns_number_total             2908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00279g1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7230374--7230379.cif.'
_cod_database_code               7230374
_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+1/2, -y+1/2, -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
Cu Cu 0.87842(12) 0.68349(6) 0.61394(5) 0.0296(3) Uani 1 1 d . .
O11 O 1.0265(7) 0.7428(3) 0.5176(3) 0.0328(9) Uani 1 1 d . .
O12 O 1.1690(7) 0.8702(3) 0.4633(3) 0.0358(10) Uani 1 1 d . .
O13 O 0.7462(7) 0.8432(3) 0.6063(3) 0.0383(10) Uani 1 1 d . .
H13 H 0.661(16) 0.834(7) 0.568(6) 0.057 Uiso 1 1 d . U
C11 C 1.0458(9) 0.8303(4) 0.5117(3) 0.0291(11) Uani 1 1 d . .
C12 C 0.9090(10) 0.8920(4) 0.5669(4) 0.0345(13) Uani 1 1 d . .
H12A H 0.993169 0.921001 0.610438 0.041 Uiso 1 1 calc R U
H12B H 0.851556 0.941173 0.531817 0.041 Uiso 1 1 calc R U
N1 N 1.0911(8) 0.7243(3) 0.7004(3) 0.0304(10) Uani 1 1 d . .
N2 N 0.7461(8) 0.6257(3) 0.7151(3) 0.0304(10) Uani 1 1 d . .
C1 C 1.2667(10) 0.7707(4) 0.6906(4) 0.0350(13) Uani 1 1 d . .
H1 H 1.303612 0.790555 0.636435 0.042 Uiso 1 1 calc R U
C2 C 1.3979(11) 0.7908(4) 0.7586(4) 0.0368(13) Uani 1 1 d . .
H2 H 1.519876 0.823276 0.749304 0.044 Uiso 1 1 calc R U
C3 C 1.3461(10) 0.7623(4) 0.8389(5) 0.0372(13) Uani 1 1 d . .
H3 H 1.431229 0.776331 0.884742 0.045 Uiso 1 1 calc R U
C4 C 1.1622(10) 0.7115(4) 0.8513(4) 0.0325(12) Uani 1 1 d . .
C4N C 1.0390(9) 0.6945(4) 0.7797(4) 0.0299(11) Uani 1 1 d . .
C5 C 1.0982(11) 0.6756(5) 0.9322(4) 0.0396(13) Uani 1 1 d . .
H5 H 1.177435 0.687441 0.980269 0.048 Uiso 1 1 calc R U
C6 C 0.9224(13) 0.6241(5) 0.9393(4) 0.0417(15) Uani 1 1 d . .
H6 H 0.884244 0.600949 0.992269 0.050 Uiso 1 1 calc R U
C7 C 0.7953(10) 0.6049(4) 0.8669(4) 0.0343(13) Uani 1 1 d . .
C7N C 0.8546(10) 0.6415(4) 0.7872(4) 0.0295(11) Uani 1 1 d . .
C8 C 0.6173(11) 0.5494(4) 0.8686(4) 0.0391(14) Uani 1 1 d . .
H8 H 0.571486 0.523825 0.919615 0.047 Uiso 1 1 calc R U
C9 C 0.5110(11) 0.5331(5) 0.7944(5) 0.0418(16) Uani 1 1 d . .
H9 H 0.393470 0.495965 0.794922 0.050 Uiso 1 1 calc R U
C10 C 0.5794(10) 0.5721(4) 0.7184(4) 0.0340(13) Uani 1 1 d . .
H10 H 0.506551 0.560244 0.668572 0.041 Uiso 1 1 calc R U
Cl Cl 1.0957(2) 0.45346(10) 0.62550(11) 0.0401(4) Uani 1 1 d . .
O1 O 1.1126(11) 0.5485(4) 0.5956(5) 0.0705(19) Uani 1 1 d . .
O4 O 1.2972(11) 0.4121(5) 0.6182(5) 0.078(2) Uani 1 1 d . .
O2 O 1.0347(13) 0.4528(5) 0.7120(5) 0.077(2) Uani 1 1 d . .
O3 O 0.9554(14) 0.4059(6) 0.5735(6) 0.091(3) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
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
O12 Cu O11 91.75(19) 3_466 .
O12 Cu N2 91.8(2) 3_466 .
O11 Cu N2 176.3(2) . .
O12 Cu N1 173.36(19) 3_466 .
O11 Cu N1 93.4(2) . .
N2 Cu N1 83.0(2) . .
O12 Cu O13 95.41(17) 3_466 .
O11 Cu O13 74.40(17) . .
N2 Cu O13 106.15(18) . .
N1 Cu O13 90.05(18) . .
O12 Cu O1 92.6(2) 3_466 .
O11 Cu O1 87.1(2) . .
N2 Cu O1 91.8(2) . .
N1 Cu O1 83.5(2) . .
O13 Cu O1 160.06(18) . .
C11 O11 Cu 121.9(4) . .
C11 O12 Cu 129.6(4) . 3_566
C12 O13 Cu 102.9(3) . .
O12 C11 O11 124.4(6) . .
O12 C11 C12 117.0(5) . .
O11 C11 C12 118.5(5) . .
O13 C12 C11 113.4(5) . .
C1 N1 C4N 118.4(6) . .
C1 N1 Cu 130.7(5) . .
C4N N1 Cu 110.8(4) . .
C10 N2 C7N 119.2(6) . .
C10 N2 Cu 128.6(5) . .
C7N N2 Cu 112.1(4) . .
N1 C1 C2 122.6(6) . .
C3 C2 C1 119.6(6) . .
C2 C3 C4 119.3(6) . .
C4N C4 C3 117.4(6) . .
C4N C4 C5 119.0(6) . .
C3 C4 C5 123.6(6) . .
N1 C4N C4 122.7(6) . .
N1 C4N C7N 117.0(5) . .
C4 C4N C7N 120.3(5) . .
C6 C5 C4 120.7(6) . .
C5 C6 C7 121.4(6) . .
C8 C7 C7N 117.0(6) . .
C8 C7 C6 124.6(6) . .
C7N C7 C6 118.5(6) . .
N2 C7N C7 122.6(6) . .
N2 C7N C4N 117.2(5) . .
C7 C7N C4N 120.2(6) . .
C9 C8 C7 119.5(6) . .
C8 C9 C10 120.0(6) . .
N2 C10 C9 121.7(6) . .
O3 Cl O2 112.1(6) . .
O3 Cl O4 110.0(6) . .
O2 Cl O4 109.1(5) . .
O3 Cl O1 108.6(5) . .
O2 Cl O1 109.8(5) . .
O4 Cl O1 107.1(5) . .
Cl O1 Cu 130.8(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu O12 1.978(5) 3_466
Cu O11 1.985(4) .
Cu N2 1.989(5) .
Cu N1 2.022(5) .
Cu O13 2.450(5) .
Cu O1 2.479(6) .
O11 C11 1.266(8) .
O12 C11 1.243(8) .
O13 C12 1.411(7) .
C11 C12 1.524(8) .
N1 C1 1.328(8) .
N1 C4N 1.360(8) .
N2 C10 1.328(8) .
N2 C7N 1.353(8) .
C1 C2 1.396(10) .
C2 C3 1.368(9) .
C3 C4 1.412(9) .
C4 C4N 1.403(9) .
C4 C5 1.433(9) .
C4N C7N 1.422(8) .
C5 C6 1.363(11) .
C6 C7 1.432(10) .
C7 C8 1.403(10) .
C7 C7N 1.411(8) .
C8 C9 1.376(10) .
C9 C10 1.392(9) .
Cl O3 1.401(7) .
Cl O2 1.416(7) .
Cl O4 1.440(6) .
Cl O1 1.447(6) .
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
C6 H6 O3 0.93 2.55 3.261(10) 133.8 2_665
C10 H10 O12 0.93 2.53 3.030(8) 114.0 3_466
C12 H12B O1 0.97 2.54 3.309(10) 136.5 3_466
O13 H13 O11 0.82(10) 1.95(9) 2.710(7) 153(9) 3_466
