#------------------------------------------------------------------------------
#$Date: 2017-03-24 08:12:22 +0200 (Fri, 24 Mar 2017) $
#$Revision: 194471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/79/7227924.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_7227924
loop_
_publ_author_name
'Demadis, Konstantinos D.'
'Anagnostou, Zafeiria'
'Panera, Aggeliki'
'Mezei, Gellert'
'Kirillova, Marina V.'
'Kirillov, Alexander M.'
_publ_section_title
;
 Three-component 1D and 2D metal phosphonates: structural variability,
 topological analysis and catalytic hydrocarboxylation of alkanes
;
_journal_issue                   29
_journal_name_full               'RSC Adv.'
_journal_page_first              17788
_journal_paper_doi               10.1039/C7RA00738H
_journal_volume                  7
_journal_year                    2017
_chemical_formula_sum            'C13 H14 Cu N2 O7 P2'
_chemical_formula_weight         435.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-11-05 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.6160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.3946(4)
_cell_length_b                   4.88940(10)
_cell_length_c                   16.9441(3)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.39
_cell_volume                     1562.73(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27347
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_min         2.159
_exptl_absorpt_coefficient_mu    1.645
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_description       prism
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2017 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0232P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0500
_refine_ls_wR_factor_ref         0.0512
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4360
_reflns_number_total             4637
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ra00738h2.cif
_cod_data_source_block           GMKDCuphenMDP_0m_a
_cod_database_code               7227924
_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   0.559
_shelx_estimated_absorpt_t_max   0.922
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
Cu1 Cu 0.49248(2) 0.76850(5) 0.54906(2) 0.01966(7) Uani 1 1 d . .
P1 P 0.41616(3) 0.30703(12) 0.40312(5) 0.01907(13) Uani 1 1 d . .
P2 P 0.34965(3) 0.51941(11) 0.50462(4) 0.01915(13) Uani 1 1 d . .
O1 O 0.48178(10) 0.4786(3) 0.46264(15) 0.0265(4) Uani 1 1 d . .
O2 O 0.41872(10) 0.0186(4) 0.43215(14) 0.0282(4) Uani 1 1 d . .
O3 O 0.40045(12) 0.3158(4) 0.29962(15) 0.0313(5) Uani 1 1 d D .
H3O H 0.388(2) 0.173(5) 0.275(3) 0.038 Uiso 1 1 d D U
O4 O 0.42445(10) 0.6132(4) 0.57444(13) 0.0255(4) Uani 1 1 d . .
O5 O 0.32669(12) 0.2648(3) 0.53050(16) 0.0275(4) Uani 1 1 d . .
O6 O 0.29505(11) 0.7501(3) 0.48896(17) 0.0285(4) Uani 1 1 d D .
H6O H 0.3078(18) 0.904(5) 0.496(2) 0.034 Uiso 1 1 d D U
O7 O 0.34860(13) 0.8434(5) 0.20326(17) 0.0357(5) Uani 1 1 d D .
H7A H 0.346(2) 0.808(8) 0.154(2) 0.043 Uiso 1 1 d D U
H7B H 0.357(2) 0.698(5) 0.225(3) 0.043 Uiso 1 1 d D U
N1 N 0.52599(12) 1.0322(4) 0.65716(15) 0.0226(4) Uani 1 1 d . .
N2 N 0.58246(11) 0.9029(4) 0.56067(16) 0.0226(4) Uani 1 1 d . .
C1 C 0.34091(13) 0.4764(5) 0.39315(17) 0.0202(5) Uani 1 1 d . .
H1A H 0.2985 0.3706 0.3520 0.024 Uiso 1 1 calc R U
H1B H 0.3352 0.6546 0.3647 0.024 Uiso 1 1 calc R U
C2 C 0.49609(15) 1.0870(6) 0.7046(2) 0.0307(6) Uani 1 1 d . .
H2 H 0.4565 0.9872 0.6920 0.037 Uiso 1 1 calc R U
C3 C 0.52239(17) 1.2914(7) 0.7737(2) 0.0369(7) Uani 1 1 d . .
H3 H 0.4998 1.3282 0.8052 0.044 Uiso 1 1 calc R U
C4 C 0.58116(16) 1.4357(6) 0.7943(2) 0.0348(7) Uani 1 1 d . .
H4 H 0.5992 1.5695 0.8406 0.042 Uiso 1 1 calc R U
C5 C 0.61445(15) 1.3815(5) 0.74526(19) 0.0267(5) Uani 1 1 d . .
C6 C 0.58394(13) 1.1755(5) 0.67684(18) 0.0219(5) Uani 1 1 d . .
C7 C 0.61471(13) 1.1065(5) 0.62461(18) 0.0219(5) Uani 1 1 d . .
C8 C 0.67553(15) 1.2428(5) 0.6405(2) 0.0276(6) Uani 1 1 d . .
C9 C 0.70304(16) 1.1594(7) 0.5874(2) 0.0374(7) Uani 1 1 d . .
H9 H 0.7427 1.2460 0.5946 0.045 Uiso 1 1 calc R U
C10 C 0.67142(17) 0.9502(7) 0.5249(2) 0.0389(7) Uani 1 1 d . .
H10 H 0.6902 0.8899 0.4907 0.047 Uiso 1 1 calc R U
C11 C 0.61061(16) 0.8267(6) 0.5126(2) 0.0312(6) Uani 1 1 d . .
H11 H 0.5892 0.6861 0.4691 0.037 Uiso 1 1 calc R U
C12 C 0.70529(15) 1.4546(6) 0.7103(2) 0.0331(7) Uani 1 1 d . .
H12 H 0.7452 1.5486 0.7214 0.040 Uiso 1 1 calc R U
C13 C 0.67617(15) 1.5197(6) 0.7603(2) 0.0323(6) Uani 1 1 d . .
H13 H 0.6967 1.6568 0.8053 0.039 Uiso 1 1 calc R 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'
P P 0.1023 0.0942 '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
O4 Cu1 O1 95.04(8) .
O4 Cu1 N1 90.07(9) .
O1 Cu1 N1 166.93(9) .
O4 Cu1 N2 163.97(8) .
O1 Cu1 N2 91.25(9) .
N1 Cu1 N2 80.87(9) .
O4 Cu1 O2 96.97(8) 1_565
O1 Cu1 O2 89.95(8) 1_565
N1 Cu1 O2 101.39(8) 1_565
N2 Cu1 O2 97.76(9) 1_565
O2 P1 O1 117.15(11) .
O2 P1 O3 109.66(12) .
O1 P1 O3 106.15(12) .
O2 P1 C1 109.57(12) .
O1 P1 C1 109.36(11) .
O3 P1 C1 104.13(12) .
O5 P2 O4 115.68(12) .
O5 P2 O6 106.61(12) .
O4 P2 O6 110.29(11) .
O5 P2 C1 110.41(11) .
O4 P2 C1 107.72(11) .
O6 P2 C1 105.69(12) .
P1 O1 Cu1 125.74(12) .
P1 O2 Cu1 135.98(12) 1_545
P1 O3 H3O 111(3) .
P2 O4 Cu1 127.97(11) .
P2 O6 H6O 118(3) .
H7A O7 H7B 100(4) .
C2 N1 C6 118.7(2) .
C2 N1 Cu1 128.1(2) .
C6 N1 Cu1 113.10(18) .
C11 N2 C7 118.2(2) .
C11 N2 Cu1 128.87(19) .
C7 N2 Cu1 112.89(17) .
P1 C1 P2 112.79(13) .
P1 C1 H1A 109.0 .
P2 C1 H1A 109.0 .
P1 C1 H1B 109.0 .
P2 C1 H1B 109.0 .
H1A C1 H1B 107.8 .
N1 C2 C3 121.9(3) .
N1 C2 H2 119.1 .
C3 C2 H2 119.1 .
C4 C3 C2 119.7(3) .
C4 C3 H3 120.1 .
C2 C3 H3 120.1 .
C3 C4 C5 119.8(3) .
C3 C4 H4 120.1 .
C5 C4 H4 120.1 .
C6 C5 C4 116.4(3) .
C6 C5 C13 118.6(3) .
C4 C5 C13 125.0(3) .
N1 C6 C5 123.5(3) .
N1 C6 C7 116.5(2) .
C5 C6 C7 120.0(2) .
N2 C7 C8 123.0(3) .
N2 C7 C6 116.2(2) .
C8 C7 C6 120.8(2) .
C9 C8 C7 117.1(3) .
C9 C8 C12 124.8(3) .
C7 C8 C12 118.1(3) .
C10 C9 C8 119.6(3) .
C10 C9 H9 120.2 .
C8 C9 H9 120.2 .
C9 C10 C11 119.8(3) .
C9 C10 H10 120.1 .
C11 C10 H10 120.1 .
N2 C11 C10 122.3(3) .
N2 C11 H11 118.8 .
C10 C11 H11 118.8 .
C13 C12 C8 121.1(3) .
C13 C12 H12 119.4 .
C8 C12 H12 119.4 .
C12 C13 C5 121.4(3) .
C12 C13 H13 119.3 .
C5 C13 H13 119.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O4 1.9466(19) .
Cu1 O1 1.9576(19) .
Cu1 N1 2.025(2) .
Cu1 N2 2.026(2) .
Cu1 O2 2.1495(19) 1_565
P1 O2 1.4845(18) .
P1 O1 1.5110(19) .
P1 O3 1.592(2) .
P1 C1 1.802(3) .
P2 O5 1.4998(18) .
P2 O4 1.5098(19) .
P2 O6 1.577(2) .
P2 C1 1.803(3) .
O2 Cu1 2.1494(19) 1_545
O3 H3O 0.78(2) .
O6 H6O 0.79(2) .
O7 H7A 0.82(3) .
O7 H7B 0.78(2) .
N1 C2 1.322(4) .
N1 C6 1.349(3) .
N2 C11 1.324(4) .
N2 C7 1.358(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 C3 1.404(4) .
C2 H2 0.9300 .
C3 C4 1.362(5) .
C3 H3 0.9300 .
C4 C5 1.409(4) .
C4 H4 0.9300 .
C5 C6 1.404(4) .
C5 C13 1.432(4) .
C6 C7 1.424(4) .
C7 C8 1.406(4) .
C8 C9 1.399(5) .
C8 C12 1.437(4) .
C9 C10 1.363(5) .
C9 H9 0.9300 .
C10 C11 1.398(4) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C13 1.357(5) .
C12 H12 0.9300 .
C13 H13 0.9300 .
