#------------------------------------------------------------------------------
#$Date: 2019-11-03 11:39:03 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/31/2243166.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243166
loop_
_publ_author_name
'Saffon-Merceron, Nathalie'
'Vigroux, Alain'
'Hoffmann, Pascal'
_publ_section_title
;
 Crystal structure of a two-dimensional coordination polymer of formula
 [Zn(NDC)(DEF)] (H₂NDC is naphthalene-2,6-dicarboxylic acid and DEF is
 N,N-diethylformamide)
;
_journal_coeditor_code           ZL2761
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1759
_journal_page_last               1762
_journal_paper_doi               10.1107/S2056989019014142
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '[Zn (C12 H6 O4) (C15 H11 N O)]'
_chemical_formula_moiety         'C17 H17 N O5 Zn'
_chemical_formula_sum            'C17 H17 N O5 Zn'
_chemical_formula_weight         380.68
_chemical_name_systematic
Poly[bis(N,N-diethylformamide)(μ₄-naphthalene-2,6-dicarboxylato)(μ₂-naphthalene-2,6-dicarboxylato)dizinc(II)]
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                97.873(4)
_cell_angle_beta                 91.620(4)
_cell_angle_gamma                91.991(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9134(5)
_cell_length_b                   8.3006(5)
_cell_length_c                   12.6413(8)
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      21.536
_cell_measurement_theta_min      2.479
_cell_volume                     821.57(9)
_computing_cell_refinement
;
APEX2 (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0751
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13141
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.771
_diffrn_source                   'fine-focus selaed tube'
_exptl_absorpt_coefficient_mu    1.521
_exptl_absorpt_correction_T_max  0.9417
_exptl_absorpt_correction_T_min  0.8628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0419
_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)+(0.0318P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                2436
_reflns_number_total             3336
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2761sup1.cif
_cod_data_source_block           global
_cod_database_code               2243166
_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   0.863
_shelx_estimated_absorpt_t_max   0.942
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.02528(5) 0.13460(5) 0.62683(3) 0.02329(12) Uani d 1 . .
O O1 -0.0138(3) 0.0539(3) 0.8118(2) 0.0495(7) Uani d 1 . .
O O2 -0.1959(3) 0.1010(3) 0.68613(17) 0.0311(5) Uani d 1 . .
O O3 0.0472(2) -0.1661(2) 0.52376(16) 0.0249(5) Uani d 1 . .
O O4 0.1080(3) 0.3581(3) 0.68413(19) 0.0376(6) Uani d 1 . .
O O5 0.2353(2) 0.0121(2) 0.60995(16) 0.0267(5) Uani d 1 . .
C C1 -0.1604(4) 0.0679(4) 0.7800(3) 0.0292(8) Uani d 1 . .
C C2 -0.3060(4) 0.0478(4) 0.8506(2) 0.0229(7) Uani d 1 . .
C C3 -0.4729(4) 0.0766(4) 0.8157(3) 0.0259(7) Uani d 1 . .
H H3 -0.491459 0.106685 0.746526 0.031 Uiso calc 1 . .
C C4 -0.6065(4) 0.0621(4) 0.8792(2) 0.0253(7) Uani d 1 . .
H H4 -0.716770 0.083839 0.854527 0.030 Uiso calc 1 . .
C C5 -0.5832(3) 0.0151(3) 0.9818(2) 0.0204(7) Uani d 1 . .
C C6 -0.7197(4) -0.0032(4) 1.0501(2) 0.0247(7) Uani d 1 . .
H H6 -0.831308 0.016042 1.026474 0.030 Uiso calc 1 . .
C C7 0.1971(4) -0.1257(4) 0.5574(2) 0.0232(7) Uani d 1 . .
C C8 0.3342(4) -0.2464(4) 0.5386(2) 0.0231(7) Uani d 1 . .
C C9 0.2888(4) -0.4062(4) 0.5012(2) 0.0266(7) Uani d 1 . .
H H9 0.173329 -0.437095 0.484564 0.032 Uiso calc 1 . .
C C10 0.4136(4) -0.5243(4) 0.4875(2) 0.0241(7) Uani d 1 . .
C C11 0.5046(4) -0.1977(4) 0.5621(3) 0.0281(8) Uani d 1 . .
H H11 0.534020 -0.086805 0.587033 0.034 Uiso calc 1 . .
C C12 0.6283(4) -0.3091(4) 0.5492(3) 0.0285(8) Uani d 1 . .
H H12 0.743193 -0.274861 0.564835 0.034 Uiso calc 1 . .
C C13 0.2535(5) 0.4026(4) 0.7188(3) 0.0369(9) Uani d 1 . .
H H13 0.341309 0.327989 0.705702 0.044 Uiso calc 1 . .
C C14 0.1574(6) 0.6627(5) 0.7929(4) 0.0628(13) Uani d 1 . .
H H14A 0.078313 0.652571 0.729974 0.075 Uiso calc 1 . .
H H14B 0.208053 0.774681 0.803717 0.075 Uiso calc 1 . .
C C15 0.0611(7) 0.6341(6) 0.8898(4) 0.0970(18) Uani d 1 . .
H H15A 0.013080 0.522378 0.879973 0.145 Uiso calc 1 . .
H H15B -0.030364 0.710761 0.899858 0.145 Uiso calc 1 . .
H H15C 0.137829 0.650364 0.952935 0.145 Uiso calc 1 . .
N N1 0.2922(4) 0.5454(4) 0.7719(2) 0.0448(8) Uani d 1 . .
C C16 0.4576(17) 0.6215(19) 0.815(2) 0.061(4) Uani d 0.516(8) A 1
H H16A 0.487379 0.713730 0.775639 0.074 Uiso calc 0.516(8) A 1
H H16B 0.447852 0.665014 0.890959 0.074 Uiso calc 0.516(8) A 1
C C17 0.5911(12) 0.5053(11) 0.8035(8) 0.065(3) Uani d 0.516(8) A 1
H H17A 0.563272 0.415235 0.843378 0.098 Uiso calc 0.516(8) A 1
H H17B 0.698301 0.559271 0.831750 0.098 Uiso calc 0.516(8) A 1
H H17C 0.601884 0.462995 0.727791 0.098 Uiso calc 0.516(8) A 1
C C16' 0.4774(18) 0.575(2) 0.8054(19) 0.062(4) Uani d 0.484(8) A 2
H H16C 0.544874 0.496333 0.760003 0.074 Uiso calc 0.484(8) A 2
H H16D 0.513676 0.685674 0.792220 0.074 Uiso calc 0.484(8) A 2
C C17' 0.5149(13) 0.5600(11) 0.9178(7) 0.074(3) Uani d 0.484(8) A 2
H H17D 0.426986 0.611745 0.962205 0.110 Uiso calc 0.484(8) A 2
H H17E 0.625043 0.613689 0.939854 0.110 Uiso calc 0.484(8) A 2
H H17F 0.517878 0.444637 0.926528 0.110 Uiso calc 0.484(8) A 2
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'
Zn Zn 0.2839 1.4301 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 Zn1 O4 . . 107.22(9)
O2 Zn1 O5 . . 136.08(9)
O4 Zn1 O5 . . 103.46(9)
O2 Zn1 O3 . 2_556 99.73(8)
O4 Zn1 O3 . 2_556 100.55(9)
O5 Zn1 O3 . 2_556 104.71(8)
O2 Zn1 C1 . . 28.93(9)
O4 Zn1 C1 . . 100.44(10)
O5 Zn1 C1 . . 115.09(9)
O3 Zn1 C1 2_556 . 128.55(9)
C1 O2 Zn1 . . 103.60(19)
C7 O3 Zn1 . 2_556 119.47(19)
C13 O4 Zn1 . . 127.3(2)
C7 O5 Zn1 . . 107.70(19)
O1 C1 O2 . . 122.1(3)
O1 C1 C2 . . 121.0(3)
O2 C1 C2 . . 116.8(3)
O1 C1 Zn1 . . 74.8(2)
O2 C1 Zn1 . . 47.47(15)
C2 C1 Zn1 . . 163.8(2)
C6 C2 C3 2_457 . 119.1(3)
C6 C2 C1 2_457 . 120.6(3)
C3 C2 C1 . . 120.3(3)
C4 C3 C2 . . 121.2(3)
C4 C3 H3 . . 119.4
C2 C3 H3 . . 119.4
C3 C4 C5 . . 120.7(3)
C3 C4 H4 . . 119.7
C5 C4 H4 . . 119.7
C4 C5 C6 . . 122.4(3)
C4 C5 C5 . 2_457 119.0(3)
C6 C5 C5 . 2_457 118.6(3)
C2 C6 C5 2_457 . 121.4(3)
C2 C6 H6 2_457 . 119.3
C5 C6 H6 . . 119.3
O5 C7 O3 . . 122.1(3)
O5 C7 C8 . . 118.2(3)
O3 C7 C8 . . 119.6(3)
C9 C8 C11 . . 120.8(3)
C9 C8 C7 . . 118.7(3)
C11 C8 C7 . . 120.5(3)
C8 C9 C10 . . 120.1(3)
C8 C9 H9 . . 119.9
C10 C9 H9 . . 119.9
C9 C10 C12 . 2_646 121.8(3)
C9 C10 C10 . 2_646 119.2(4)
C12 C10 C10 2_646 2_646 118.9(3)
C12 C11 C8 . . 120.4(3)
C12 C11 H11 . . 119.8
C8 C11 H11 . . 119.8
C11 C12 C10 . 2_646 120.5(3)
C11 C12 H12 . . 119.7
C10 C12 H12 2_646 . 119.7
O4 C13 N1 . . 123.8(3)
O4 C13 H13 . . 118.1
N1 C13 H13 . . 118.1
N1 C14 C15 . . 111.5(4)
N1 C14 H14A . . 109.3
C15 C14 H14A . . 109.3
N1 C14 H14B . . 109.3
C15 C14 H14B . . 109.3
H14A C14 H14B . . 108.0
C14 C15 H15A . . 109.5
C14 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C14 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C13 N1 C14 . . 118.8(3)
C13 N1 C16 . . 131.2(8)
C14 N1 C16 . . 110.0(8)
C13 N1 C16' . . 115.1(9)
C14 N1 C16' . . 126.1(9)
C17 C16 N1 . . 111.5(12)
C17 C16 H16A . . 109.3
N1 C16 H16A . . 109.3
C17 C16 H16B . . 109.3
N1 C16 H16B . . 109.3
H16A C16 H16B . . 108.0
C16 C17 H17A . . 109.5
C16 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
C16 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
C17' C16' N1 . . 114.1(15)
C17' C16' H16C . . 108.7
N1 C16' H16C . . 108.7
C17' C16' H16D . . 108.7
N1 C16' H16D . . 108.7
H16C C16' H16D . . 107.6
C16' C17' H17D . . 109.5
C16' C17' H17E . . 109.5
H17D C17' H17E . . 109.5
C16' C17' H17F . . 109.5
H17D C17' H17F . . 109.5
H17E C17' H17F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn1 O2 . 1.949(2)
Zn1 O4 . 1.979(2)
Zn1 O5 . 1.980(2)
Zn1 O3 2_556 2.026(2)
Zn1 C1 . 2.571(3)
O1 C1 . 1.231(4)
O2 C1 . 1.280(4)
O3 C7 . 1.267(3)
O4 C13 . 1.246(4)
O5 C7 . 1.264(4)
C1 C2 . 1.496(4)
C2 C6 2_457 1.368(4)
C2 C3 . 1.419(4)
C3 C4 . 1.358(4)
C3 H3 . 0.9500
C4 C5 . 1.413(4)
C4 H4 . 0.9500
C5 C6 . 1.420(4)
C5 C5 2_457 1.424(5)
C6 H6 . 0.9500
C7 C8 . 1.504(4)
C8 C9 . 1.378(4)
C8 C11 . 1.406(4)
C9 C10 . 1.413(4)
C9 H9 . 0.9500
C10 C12 2_646 1.422(4)
C10 C10 2_646 1.426(6)
C11 C12 . 1.368(4)
C11 H11 . 0.9500
C12 H12 . 0.9500
C13 N1 . 1.302(4)
C13 H13 . 0.9500
C14 N1 . 1.474(5)
C14 C15 . 1.503(6)
C14 H14A . 0.9900
C14 H14B . 0.9900
C15 H15A . 0.9800
C15 H15B . 0.9800
C15 H15C . 0.9800
N1 C16 . 1.488(11)
N1 C16' . 1.517(11)
C16 C17 . 1.452(17)
C16 H16A . 0.9900
C16 H16B . 0.9900
C17 H17A . 0.9800
C17 H17B . 0.9800
C17 H17C . 0.9800
C16' C17' . 1.47(2)
C16' H16C . 0.9900
C16' H16D . 0.9900
C17' H17D . 0.9800
C17' H17E . 0.9800
C17' H17F . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O1 1_555 1_555 1_455 0.95 2.39 3.307(4) 161 yes
C12 H12 O3 1_555 1_555 1_655 0.95 2.63 3.548(4) 156 yes
C16 H16 <i>Cg</i>1 1_555 1_555 1_665 0.95 2.99 3.520(17) 114 yes
C16 H16 <i>Cg</i>2 1_555 1_555 2_567 0.95 2.99 3.520(17) 114 yes
