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#$Date: 2016-03-24 02:26:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179579 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/44/4504439.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_4504439
loop_
_publ_author_name
'Braverman, Maxwell A.'
'LaDuca, Robert L.'
_publ_section_title
;
 Luminescent Two- and Three-Dimensional Zinc Coordination Polymers
 Containing Isomers of Phenylenediacetate and a Kinked Tethering
 Organodiimine
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2343
_journal_paper_doi               10.1021/cg070599f
_journal_volume                  7
_journal_year                    2007
_chemical_formula_sum            'C20 H17 N3 O4 Zn'
_chemical_formula_weight         428.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.972(11)
_cell_length_b                   13.188(17)
_cell_length_c                   15.573(19)
_cell_measurement_reflns_used    19324
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.02
_cell_volume                     1843(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19324
_diffrn_reflns_theta_full        28.10
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    1.365
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.7866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4228
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0350P)²+1.8830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                2713
_reflns_number_total             4228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg070599f-file004.cif
_cod_data_source_block           ortho1
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4504439
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.95237(6) 0.07407(4) 0.83034(5) 0.04136(17) Uani 1 1 d .
O1 O 1.0191(14) 0.1505(6) 0.6819(8) 0.276(8) Uani 1 1 d .
O2 O 0.9160(9) 0.2084(4) 0.7827(4) 0.119(2) Uani 1 1 d .
O3 O 0.7295(5) 0.5460(3) 0.3991(3) 0.0601(11) Uani 1 1 d .
O4 O 0.8446(6) 0.4788(3) 0.2872(3) 0.0631(12) Uani 1 1 d .
N1 N 1.4111(5) -0.3972(3) 0.4351(3) 0.0384(11) Uani 1 1 d .
N2 N 1.1753(5) -0.3274(3) 0.6603(3) 0.0429(11) Uani 1 1 d D
H2N H 1.168(6) -0.384(3) 0.693(3) 0.051 Uiso 1 1 d D
N3 N 1.0324(5) -0.0546(3) 0.7736(3) 0.0386(10) Uani 1 1 d .
C1 C 1.4087(6) -0.4592(4) 0.5039(3) 0.0410(13) Uani 1 1 d .
H1 H 1.4620 -0.5196 0.5014 0.049 Uiso 1 1 calc R
C2 C 1.3317(6) -0.4374(4) 0.5770(3) 0.0377(12) Uani 1 1 d .
H2 H 1.3313 -0.4835 0.6221 0.045 Uiso 1 1 calc R
C3 C 1.2536(6) -0.3467(3) 0.5847(3) 0.0330(11) Uani 1 1 d .
C4 C 1.2495(6) -0.2834(4) 0.5124(3) 0.0432(14) Uani 1 1 d .
H4 H 1.1932 -0.2242 0.5127 0.052 Uiso 1 1 calc R
C5 C 1.3311(7) -0.3110(4) 0.4406(3) 0.0413(14) Uani 1 1 d .
H5 H 1.3306 -0.2676 0.3936 0.050 Uiso 1 1 calc R
C6 C 0.9852(6) -0.1475(4) 0.8004(3) 0.0389(13) Uani 1 1 d .
H6 H 0.9181 -0.1506 0.8458 0.047 Uiso 1 1 calc R
C7 C 1.0309(6) -0.2356(4) 0.7643(3) 0.0424(13) Uani 1 1 d .
H7 H 0.9948 -0.2969 0.7853 0.051 Uiso 1 1 calc R
C8 C 1.1329(6) -0.2351(4) 0.6951(3) 0.0363(12) Uani 1 1 d .
C9 C 1.1863(6) -0.1402(4) 0.6696(4) 0.0428(13) Uani 1 1 d .
H9 H 1.2562 -0.1350 0.6257 0.051 Uiso 1 1 calc R
C10 C 1.1340(6) -0.0538(4) 0.7104(4) 0.0423(13) Uani 1 1 d .
H10 H 1.1716 0.0085 0.6929 0.051 Uiso 1 1 calc R
C11 C 1.0402(6) 0.3388(4) 0.5851(3) 0.0421(13) Uani 1 1 d .
C12 C 0.9902(6) 0.4200(4) 0.5362(4) 0.0432(14) Uani 1 1 d .
H12 H 0.9157 0.4612 0.5586 0.052 Uiso 1 1 calc R
C13 C 1.0463(6) 0.4426(4) 0.4552(4) 0.0444(14) Uani 1 1 d .
C14 C 1.1557(7) 0.3793(5) 0.4225(4) 0.0521(15) Uani 1 1 d .
H14 H 1.1954 0.3923 0.3685 0.063 Uiso 1 1 calc R
C15 C 1.2069(7) 0.2969(5) 0.4690(4) 0.0586(17) Uani 1 1 d .
H15 H 1.2793 0.2544 0.4460 0.070 Uiso 1 1 calc R
C16 C 1.1492(7) 0.2783(5) 0.5503(4) 0.0555(15) Uani 1 1 d .
H16 H 1.1852 0.2236 0.5818 0.067 Uiso 1 1 calc R
C17 C 0.9830(8) 0.3259(5) 0.6760(4) 0.0608(18) Uani 1 1 d .
H17A H 1.0455 0.3672 0.7129 0.073 Uiso 1 1 calc R
H17B H 0.8838 0.3551 0.6779 0.073 Uiso 1 1 calc R
C18 C 0.9737(8) 0.2226(5) 0.7159(5) 0.0640(18) Uani 1 1 d .
C19 C 0.9931(7) 0.5350(5) 0.4066(5) 0.0599(18) Uani 1 1 d .
H19A H 1.0682 0.5541 0.3648 0.072 Uiso 1 1 calc R
H19B H 0.9818 0.5909 0.4466 0.072 Uiso 1 1 calc R
C20 C 0.8445(7) 0.5179(4) 0.3600(3) 0.0345(13) 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
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 Zn1 O3 103.7(2) . 4_645
O2 Zn1 N3 130.5(2) . .
O3 Zn1 N3 111.54(18) 4_645 .
O2 Zn1 N1 103.4(3) . 4_755
O3 Zn1 N1 95.5(2) 4_645 4_755
N3 Zn1 N1 106.52(18) . 4_755
C18 O2 Zn1 114.1(5) . .
C20 O3 Zn1 118.0(4) . 4_654
C5 N1 C1 116.9(5) . .
C5 N1 Zn1 121.3(4) . 4_744
C1 N1 Zn1 121.6(4) . 4_744
C8 N2 C3 129.0(4) . .
C10 N3 C6 116.3(4) . .
C10 N3 Zn1 123.3(4) . .
C6 N3 Zn1 120.4(3) . .
N1 C1 C2 123.0(5) . .
C1 C2 C3 120.6(5) . .
C2 C3 N2 118.9(4) . .
C2 C3 C4 117.1(5) . .
N2 C3 C4 123.8(4) . .
C5 C4 C3 118.5(5) . .
N1 C5 C4 123.7(5) . .
C7 C6 N3 123.4(5) . .
C6 C7 C8 120.5(5) . .
N2 C8 C9 125.5(5) . .
N2 C8 C7 118.1(5) . .
C9 C8 C7 116.3(5) . .
C10 C9 C8 119.3(5) . .
N3 C10 C9 124.1(5) . .
C16 C11 C12 117.4(5) . .
C16 C11 C17 123.0(6) . .
C12 C11 C17 119.3(5) . .
C11 C12 C13 123.1(5) . .
C14 C13 C12 117.4(5) . .
C14 C13 C19 121.8(6) . .
C12 C13 C19 120.8(6) . .
C15 C14 C13 121.1(6) . .
C14 C15 C16 119.5(6) . .
C11 C16 C15 121.5(6) . .
C18 C17 C11 120.5(6) . .
O1 C18 O2 115.2(7) . .
O1 C18 C17 122.4(8) . .
O2 C18 C17 122.4(7) . .
C13 C19 C20 113.1(4) . .
O4 C20 O3 124.3(6) . .
O4 C20 C19 119.4(6) . .
O3 C20 C19 116.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O2 1.949(6) .
Zn1 O3 1.986(5) 4_645
Zn1 N3 2.044(5) .
Zn1 N1 2.075(5) 4_755
O1 C18 1.161(11) .
O2 C18 1.177(8) .
O3 C20 1.253(7) .
O3 Zn1 1.986(5) 4_654
O4 C20 1.246(6) .
N1 C5 1.347(7) .
N1 C1 1.348(7) .
N1 Zn1 2.075(5) 4_744
N2 C8 1.387(7) .
N2 C3 1.395(7) .
N3 C10 1.341(7) .
N3 C6 1.362(7) .
C1 C2 1.362(7) .
C2 C3 1.390(6) .
C3 C4 1.402(7) .
C4 C5 1.385(7) .
C6 C7 1.353(7) .
C7 C8 1.414(7) .
C8 C9 1.398(7) .
C9 C10 1.386(7) .
C11 C16 1.375(8) .
C11 C12 1.388(7) .
C11 C17 1.514(8) .
C12 C13 1.391(8) .
C13 C14 1.385(8) .
C13 C19 1.512(8) .
C14 C15 1.383(8) .
C15 C16 1.389(8) .
C17 C18 1.500(9) .
C19 C20 1.534(8) .
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
N2 H2N O4 0.898(19) 1.94(2) 2.815(7) 164(5) 2_755
