#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:19:41 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179660 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/13/4511386.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_4511386
loop_
_publ_author_name
'Dias, Sara S. P.'
'André, Vânia'
'Kłak, Julia'
'Duarte, M. Teresa'
'Kirillov, Alexander M.'
_publ_section_title
;
 Topological Diversity of Supramolecular Networks Constructed from
 Copper(II) Aminoalcohol Blocks and 2,6-Naphthalenedicarboxylate Linkers:
 Self-Assembly Synthesis, Structural Features, and Magnetic Properties
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3398
_journal_paper_doi               10.1021/cg500716d
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C11 H17 Cu N O5'
_chemical_formula_weight         306.80
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.350(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1134(10)
_cell_length_b                   9.2965(8)
_cell_length_c                   12.0316(10)
_cell_measurement_temperature    273(2)
_cell_volume                     1332.86(19)
_computing_cell_refinement       'BRUKER SMART (Bruker, 2005)'
_computing_data_collection       'BRUKER APEX2 (Bruker, 2005)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP 3.2 (Farrugia, 1997) and Mercury 2.3'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR 97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31544
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    1.650
_exptl_absorpt_correction_T_max  0.8523
_exptl_absorpt_correction_T_min  0.7337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0398
_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)+(0.0561P)²+0.6622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                2862
_reflns_number_total             3840
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            Compound2.cif
_cod_data_source_block           spd059dp21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4511386--4511389.cif.
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4511386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.22390(17) 0.2108(2) 0.43492(19) 0.0333(4) Uani 1 1 d .
C2 C 0.13406(16) 0.3206(2) 0.44026(18) 0.0309(4) Uani 1 1 d .
C3 C 0.11751(16) 0.3720(2) 0.54296(18) 0.0320(4) Uani 1 1 d .
H6 H 0.1623 0.3385 0.6088 0.038 Uiso 1 1 calc R
C4 C 0.03376(17) 0.4747(2) 0.55018(17) 0.0299(4) Uani 1 1 d .
C5 C 0.01619(19) 0.5307(3) 0.65572(19) 0.0379(5) Uani 1 1 d .
H7 H 0.0607 0.4990 0.7224 0.046 Uiso 1 1 calc R
C6 C -0.06528(19) 0.6306(3) 0.65979(19) 0.0382(5) Uani 1 1 d .
H5 H -0.0757 0.6669 0.7292 0.046 Uiso 1 1 calc R
C7 C 0.5493(2) 0.2636(3) 0.4704(2) 0.0452(6) Uani 1 1 d .
H1A H 0.5264 0.3362 0.5195 0.054 Uiso 1 1 calc R
H1B H 0.5123 0.2834 0.3935 0.054 Uiso 1 1 calc R
C8 C 0.3244(3) -0.2673(3) 0.5218(3) 0.0585(7) Uani 1 1 d .
H2A H 0.2882 -0.2745 0.4433 0.070 Uiso 1 1 calc R
H2B H 0.3036 -0.3511 0.5614 0.070 Uiso 1 1 calc R
C9 C 0.3079(3) -0.1490(4) 0.6993(2) 0.0600(8) Uani 1 1 d .
H9A H 0.2429 -0.1918 0.7229 0.072 Uiso 1 1 calc R
H9B H 0.3713 -0.2126 0.7226 0.072 Uiso 1 1 calc R
C10 C 0.3316(3) -0.0084(4) 0.7558(2) 0.0608(8) Uani 1 1 d .
H8A H 0.2672 0.0544 0.7349 0.073 Uiso 1 1 calc R
H8B H 0.3439 -0.0218 0.8371 0.073 Uiso 1 1 calc R
C11 C 0.1650(2) -0.1117(4) 0.5315(3) 0.0717(10) Uani 1 1 d .
H11A H 0.1418 -0.0256 0.5649 0.108 Uiso 1 1 calc R
H11B H 0.1235 -0.1922 0.5524 0.108 Uiso 1 1 calc R
H11C H 0.1511 -0.1019 0.4508 0.108 Uiso 1 1 calc R
N1 N 0.28627(17) -0.1354(2) 0.57225(18) 0.0413(4) Uani 1 1 d .
O1 O 0.23040(14) 0.1521(2) 0.34452(14) 0.0472(4) Uani 1 1 d .
O2 O 0.28833(13) 0.18507(19) 0.52925(14) 0.0408(4) Uani 1 1 d .
O1W O 0.61500(18) -0.0934(3) 0.79934(19) 0.0581(5) Uani 1 1 d D
O3 O 0.52019(16) 0.1299(2) 0.5025(2) 0.0616(6) Uani 1 1 d .
O4 O 0.42602(19) 0.0559(2) 0.72559(17) 0.0533(5) Uani 1 1 d .
Cu1 Cu 0.38952(2) 0.02581(3) 0.52998(2) 0.03453(11) Uani 1 1 d .
H1W H 0.624(3) -0.161(3) 0.845(3) 0.090(13) Uiso 1 1 d D
H2W H 0.658(3) -0.111(4) 0.752(3) 0.084(13) Uiso 1 1 d D
H001 H 0.472(4) 0.006(4) 0.750(4) 0.086(15) 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_1
_geom_angle_site_symmetry_3
O1 C1 O2 125.09(19) . .
O1 C1 C2 120.03(19) . .
O2 C1 C2 114.88(19) . .
C3 C2 C6 119.77(18) . 3_566
C3 C2 C1 119.96(18) . .
C6 C2 C1 120.26(19) 3_566 .
C2 C3 C4 121.02(19) . .
C2 C3 H6 119.5 . .
C4 C3 H6 119.5 . .
C3 C4 C4 119.1(2) . 3_566
C3 C4 C5 121.90(18) . .
C4 C4 C5 119.0(2) 3_566 .
C6 C5 C4 120.5(2) . .
C6 C5 H7 119.8 . .
C4 C5 H7 119.8 . .
C5 C6 C2 120.6(2) . 3_566
C5 C6 H5 119.7 . .
C2 C6 H5 119.7 3_566 .
O3 C7 C8 108.2(2) . 3_656
O3 C7 H1A 110.1 . .
C8 C7 H1A 110.1 3_656 .
O3 C7 H1B 110.1 . .
C8 C7 H1B 110.1 3_656 .
H1A C7 H1B 108.4 . .
N1 C8 C7 110.0(2) . 3_656
N1 C8 H2A 109.7 . .
C7 C8 H2A 109.7 3_656 .
N1 C8 H2B 109.7 . .
C7 C8 H2B 109.7 3_656 .
H2A C8 H2B 108.2 . .
C10 C9 N1 112.1(2) . .
C10 C9 H9A 109.2 . .
N1 C9 H9A 109.2 . .
C10 C9 H9B 109.2 . .
N1 C9 H9B 109.2 . .
H9A C9 H9B 107.9 . .
O4 C10 C9 111.1(2) . .
O4 C10 H8A 109.4 . .
C9 C10 H8A 109.4 . .
O4 C10 H8B 109.4 . .
C9 C10 H8B 109.4 . .
H8A C10 H8B 108.0 . .
N1 C11 H11A 109.5 . .
N1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C11 N1 C8 110.6(2) . .
C11 N1 C9 109.3(2) . .
C8 N1 C9 109.6(2) . .
C11 N1 Cu1 114.71(19) . .
C8 N1 Cu1 104.61(15) . .
C9 N1 Cu1 107.83(17) . .
C1 O2 Cu1 115.81(14) . .
H1W O1W H2W 106(4) . .
C7 O3 Cu1 116.62(15) . 3_656
C7 O3 Cu1 139.85(16) . .
Cu1 O3 Cu1 99.98(9) 3_656 .
C10 O4 Cu1 101.28(16) . .
C10 O4 H001 102(3) . .
Cu1 O4 H001 109(4) . .
O3 Cu1 O2 168.03(9) 3_656 .
O3 Cu1 O3 80.02(9) 3_656 .
O2 Cu1 O3 98.90(7) . .
O3 Cu1 N1 83.94(9) 3_656 .
O2 Cu1 N1 98.38(8) . .
O3 Cu1 N1 162.21(8) . .
O3 Cu1 O4 106.72(9) 3_656 .
O2 Cu1 O4 85.25(7) . .
O3 Cu1 O4 95.74(10) . .
N1 Cu1 O4 81.52(8) . .
O3 Cu1 Cu1 40.47(6) 3_656 3_656
O2 Cu1 Cu1 137.26(6) . 3_656
O3 Cu1 Cu1 39.54(5) . 3_656
N1 Cu1 Cu1 124.01(6) . 3_656
O4 Cu1 Cu1 104.59(6) . 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.232(3) .
C1 O2 1.279(3) .
C1 C2 1.501(3) .
C2 C3 1.373(3) .
C2 C6 1.410(3) 3_566
C3 C4 1.407(3) .
C3 H6 0.9300 .
C4 C4 1.412(4) 3_566
C4 C5 1.424(3) .
C5 C6 1.362(3) .
C5 H7 0.9300 .
C6 C2 1.410(3) 3_566
C6 H5 0.9300 .
C7 O3 1.367(3) .
C7 C8 1.515(4) 3_656
C7 H1A 0.9700 .
C7 H1B 0.9700 .
C8 N1 1.479(3) .
C8 C7 1.515(4) 3_656
C8 H2A 0.9700 .
C8 H2B 0.9700 .
C9 C10 1.477(5) .
C9 N1 1.509(3) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 O4 1.396(4) .
C10 H8A 0.9700 .
C10 H8B 0.9700 .
C11 N1 1.479(4) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
N1 Cu1 2.073(2) .
O2 Cu1 1.9211(15) .
O1W H1W 0.835(19) .
O1W H2W 0.856(18) .
O3 Cu1 1.8968(17) 3_656
O3 Cu1 1.9338(19) .
O4 Cu1 2.332(2) .
O4 H001 0.74(4) .
Cu1 O3 1.8968(17) 3_656
Cu1 Cu1 2.9341(5) 3_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 171.5(2) . .
O2 C1 C2 C3 -7.7(3) . .
O1 C1 C2 C6 -7.5(3) . 3_566
O2 C1 C2 C6 173.3(2) . 3_566
C6 C2 C3 C4 -0.9(4) 3_566 .
C1 C2 C3 C4 -179.9(2) . .
C2 C3 C4 C4 -0.1(4) . 3_566
C2 C3 C4 C5 -179.2(2) . .
C3 C4 C5 C6 179.7(2) . .
C4 C4 C5 C6 0.7(4) 3_566 .
C4 C5 C6 C2 0.4(4) . 3_566
N1 C9 C10 O4 -59.9(3) . .
C7 C8 N1 C11 160.2(3) 3_656 .
C7 C8 N1 C9 -79.2(3) 3_656 .
C7 C8 N1 Cu1 36.2(3) 3_656 .
C10 C9 N1 C11 -89.7(3) . .
C10 C9 N1 C8 148.9(3) . .
C10 C9 N1 Cu1 35.6(3) . .
O1 C1 O2 Cu1 -8.0(3) . .
C2 C1 O2 Cu1 171.19(14) . .
C8 C7 O3 Cu1 -31.7(3) 3_656 3_656
C8 C7 O3 Cu1 174.8(2) 3_656 .
C9 C10 O4 Cu1 46.7(3) . .
C1 O2 Cu1 O3 11.0(5) . 3_656
C1 O2 Cu1 O3 94.83(18) . .
C1 O2 Cu1 N1 -89.40(17) . .
C1 O2 Cu1 O4 -170.09(18) . .
C1 O2 Cu1 Cu1 83.50(18) . 3_656
C7 O3 Cu1 O3 156.1(4) . 3_656
Cu1 O3 Cu1 O3 0.0 3_656 3_656
C7 O3 Cu1 O2 -11.8(3) . .
Cu1 O3 Cu1 O2 -167.91(9) 3_656 .
C7 O3 Cu1 N1 -178.0(3) . .
Cu1 O3 Cu1 N1 25.9(4) 3_656 .
C7 O3 Cu1 O4 -97.9(3) . .
Cu1 O3 Cu1 O4 106.02(10) 3_656 .
C7 O3 Cu1 Cu1 156.1(4) . 3_656
C11 N1 Cu1 O3 -137.4(2) . 3_656
C8 N1 Cu1 O3 -15.97(19) . 3_656
C9 N1 Cu1 O3 100.67(19) . 3_656
C11 N1 Cu1 O2 30.8(2) . .
C8 N1 Cu1 O2 152.19(18) . .
C9 N1 Cu1 O2 -91.17(18) . .
C11 N1 Cu1 O3 -163.0(3) . .
C8 N1 Cu1 O3 -41.6(4) . .
C9 N1 Cu1 O3 75.0(4) . .
C11 N1 Cu1 O4 114.7(2) . .
C8 N1 Cu1 O4 -123.93(19) . .
C9 N1 Cu1 O4 -7.29(17) . .
C11 N1 Cu1 Cu1 -143.4(2) . 3_656
C8 N1 Cu1 Cu1 -22.0(2) . 3_656
C9 N1 Cu1 Cu1 94.64(17) . 3_656
C10 O4 Cu1 O3 -102.31(19) . 3_656
C10 O4 Cu1 O2 77.92(19) . .
C10 O4 Cu1 O3 176.42(18) . .
C10 O4 Cu1 N1 -21.30(18) . .
C10 O4 Cu1 Cu1 -144.36(17) . 3_656
