#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/10/2011089.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_2011089
loop_
_publ_author_name
'Medina, Gerardo'
'Gasque, Laura'
'Bernès, Sylvain'
_publ_section_title
;Aqua(5,6-dimethyl-1,10-phenanthroline-N,N')(glycolato-O,O')copper(II)
 nitrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              766
_journal_page_last               768
_journal_paper_doi               10.1107/S0108270100004777
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          '[Cu(C2 H3 O3 )(C14 H12 N2 )(H2 O)]NO3 '
_chemical_formula_moiety         'C16 H17 Cu N2 O4 + , NO3 - '
_chemical_formula_sum            'C16 H17 Cu N3 O7'
_chemical_formula_weight         426.87
_chemical_name_systematic
;
Aqua(5,6-dimethyl-1,10-phenanthroline)(glycolato)copper(II) nitrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.225(8)
_cell_angle_beta                 105.450(12)
_cell_angle_gamma                103.760(9)
_cell_formula_units_Z            2
_cell_length_a                   7.0373(7)
_cell_length_b                   10.0928(11)
_cell_length_c                   13.1649(13)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.51
_cell_measurement_theta_min      4.57
_cell_volume                     831.68(17)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS  (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL  (Sheldrick, 1995)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .985
_diffrn_measured_fraction_theta_max .985
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0191
_diffrn_reflns_av_sigmaI/netI    .0369
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4927
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        7.20
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  .762
_exptl_absorpt_correction_T_min  .614
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '24 psi scans with XSCANS (Fait, 1991)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             438
_exptl_crystal_size_max          .7
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .2
_refine_diff_density_max         .378
_refine_diff_density_min         -.359
_refine_ls_extinction_coef       .0109(14)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          .0429
_refine_ls_R_factor_gt           .0339
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;calc w = 1/[σ²(Fo²)+(0.0419P)²+0.3303P] where
  P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0919
_reflns_number_gt                3406
_reflns_number_total             3969
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1111.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        831.68(15)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2011089
_cod_database_fobs_code          2011089
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 .00049(4) .18606(2) .306460(18) .03179(10) Uani d . 1 . . Cu
N1 -.0404(3) .36015(18) .26942(13) .0298(4) Uani d . 1 . . N
C2 .0097(4) .4922(2) .33640(18) .0376(5) Uani d . 1 . . C
H2A .0703 .5108 .4123 .045 Uiso calc R 1 . . H
C3 -.0252(4) .6040(2) .2972(2) .0415(5) Uani d . 1 . . C
H3A .0107 .6955 .3464 .050 Uiso calc R 1 . . H
C4 -.1127(4) .5786(2) .18570(19) .0385(5) Uani d . 1 . . C
H4A -.1353 .6533 .1591 .046 Uiso calc R 1 . . H
C5 -.1689(3) .4393(2) .11067(17) .0299(4) Uani d . 1 . . C
C6 -.2596(3) .4025(2) -.00892(17) .0314(4) Uani d . 1 . . C
C7 -.3100(3) .2640(2) -.07512(17) .0323(4) Uani d . 1 . . C
C8 -.2707(3) .1539(2) -.02594(15) .0281(4) Uani d . 1 . . C
C9 -.3182(3) .0088(2) -.08691(16) .0336(4) Uani d . 1 . . C
H9A -.3790 -.0217 -.1637 .040 Uiso calc R 1 . . H
C10 -.2748(4) -.0875(2) -.03289(17) .0349(5) Uani d . 1 . . C
H10A -.3073 -.1835 -.0728 .042 Uiso calc R 1 . . H
C11 -.1814(3) -.0402(2) .08263(16) .0321(4) Uani d . 1 . . C
H11A -.1518 -.1058 .1187 .038 Uiso calc R 1 . . H
N12 -.1340(3) .09543(17) .14184(13) .0278(3) Uani d . 1 . . N
C13 -.1780(3) .1902(2) .08941(15) .0258(4) Uani d . 1 . . C
C14 -.1281(3) .3345(2) .15818(15) .0263(4) Uani d . 1 . . C
C15 -.2911(4) .5220(3) -.0550(2) .0423(5) Uani d . 1 . . C
H15A -.3516 .4846 -.1344 .063 Uiso calc R 1 . . H
H15B -.1594 .5945 -.0346 .063 Uiso calc R 1 . . H
H15C -.3823 .5631 -.0255 .063 Uiso calc R 1 . . H
C16 -.4092(4) .2181(3) -.19971(18) .0485(6) Uani d . 1 . . C
H16A -.4276 .2996 -.2222 .073 Uiso calc R 1 . . H
H16B -.5421 .1460 -.2222 .073 Uiso calc R 1 . . H
H16C -.3211 .1796 -.2339 .073 Uiso calc R 1 . . H
O17 .0560(3) .01614(16) .32853(12) .0427(4) Uani d . 1 . . O
C18 .1748(4) .0287(2) .42474(17) .0359(5) Uani d . 1 . . C
O19 .2113(3) -.07235(19) .45395(14) .0538(5) Uani d . 1 . . O
C20 .2771(4) .1779(2) .50724(18) .0406(5) Uani d . 1 . . C
H20A .2529 .1786 .5765 .049 Uiso calc R 1 . . H
H20B .4260 .2065 .5221 .049 Uiso calc R 1 . . H
O21 .1923(3) .27627(16) .46286(12) .0438(4) Uani d . 1 . . O
H21 .2678 .3578 .5119 .066 Uiso d R 1 . . H
O22 -.2927(3) .13929(19) .35139(14) .0453(4) Uani d . 1 . . O
H22A -.2642 .1166 .4027 .068 Uiso d R 1 . . H
H22B -.3535 .2060 .3584 .068 Uiso d R 1 . . H
N23 .4971(3) .4160(2) .34116(14) .0381(4) Uani d . 1 . . N
O24 .6400(3) .4286(2) .42635(16) .0614(5) Uani d . 1 . . O
O25 .4569(4) .5245(2) .32854(18) .0662(6) Uani d . 1 . . O
O26 .3957(4) .2972(2) .27269(17) .0733(7) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu .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_publ_flag
O17 Cu1 N1 172.93(7) y
O17 Cu1 O21 83.09(6) y
N1 Cu1 O21 99.98(6) y
O17 Cu1 N12 93.32(7) y
N1 Cu1 N12 82.30(7) y
O21 Cu1 N12 167.20(7) y
O17 Cu1 O22 93.45(7) y
N1 Cu1 O22 92.64(7) y
O21 Cu1 O22 94.83(7) y
N12 Cu1 O22 97.65(7) y
O22 Cu1 O26 170.12(16) y
C2 N1 C14 118.26(18) ?
C2 N1 Cu1 129.10(15) ?
C14 N1 Cu1 112.62(13) ?
N1 C2 C3 122.2(2) ?
C4 C3 C2 119.6(2) ?
C3 C4 C5 120.3(2) ?
C14 C5 C4 115.71(19) ?
C14 C5 C6 119.96(18) ?
C4 C5 C6 124.31(19) ?
C7 C6 C5 120.14(18) ?
C7 C6 C15 122.63(19) ?
C5 C6 C15 117.2(2) ?
C6 C7 C8 120.12(18) ?
C6 C7 C16 122.71(19) ?
C8 C7 C16 117.2(2) ?
C13 C8 C9 115.97(18) ?
C13 C8 C7 119.77(18) ?
C9 C8 C7 124.26(18) ?
C10 C9 C8 120.01(18) ?
C9 C10 C11 119.52(19) ?
N12 C11 C10 121.75(19) ?
C11 N12 C13 119.01(17) ?
C11 N12 Cu1 128.38(14) ?
C13 N12 Cu1 112.61(13) ?
N12 C13 C8 123.73(18) ?
N12 C13 C14 116.42(16) ?
C8 C13 C14 119.84(17) ?
N1 C14 C5 123.86(18) ?
N1 C14 C13 116.00(17) ?
C5 C14 C13 120.14(17) ?
C18 O17 Cu1 116.71(14) ?
O19 C18 O17 124.2(2) ?
O19 C18 C20 118.24(19) ?
O17 C18 C20 117.59(19) ?
O21 C20 C18 109.29(17) ?
C20 O21 Cu1 112.77(12) ?
O25 N23 O26 120.8(2) ?
O25 N23 O24 118.5(2) ?
O26 N23 O24 120.7(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O17 . 1.9144(15) y
Cu1 N1 . 1.9913(17) y
Cu1 O21 . 1.9918(15) y
Cu1 N12 . 2.0044(16) y
Cu1 O22 . 2.2681(18) y
Cu1 O26 . 2.932(3) y
N1 C2 . 1.323(3) ?
N1 C14 . 1.365(2) ?
C2 C3 . 1.390(3) ?
C3 C4 . 1.367(3) ?
C4 C5 . 1.414(3) ?
C5 C14 . 1.394(3) ?
C5 C6 . 1.452(3) ?
C6 C7 . 1.372(3) ?
C6 C15 . 1.504(3) ?
C7 C8 . 1.453(3) ?
C7 C16 . 1.510(3) ?
C8 C13 . 1.403(3) ?
C8 C9 . 1.410(3) ?
C9 C10 . 1.373(3) ?
C10 C11 . 1.400(3) ?
C11 N12 . 1.322(2) ?
N12 C13 . 1.348(2) ?
C13 C14 . 1.431(3) ?
O17 C18 . 1.277(2) ?
C18 O19 . 1.227(3) ?
C18 C20 . 1.512(3) ?
C20 O21 . 1.430(3) ?
N23 O25 . 1.230(3) ?
N23 O26 . 1.231(3) ?
N23 O24 . 1.248(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
O21 H21 O24 2_666 .862 1.995 2.795(2) 154.05 y
O21 H21 O25 2_666 .862 2.274 3.030(2) 146.44 y
O21 H21 N23 2_666 .862 2.484 3.344(2) 175.91 y
O22 H22A O19 2_556 .880 1.997 2.747(3) 172.24 y
O22 H22B O24 1_455 .880 2.237 3.052(3) 153.97 y
O22 H22B O26 1_455 .880 2.329 3.103(3) 146.85 y
O22 H22B N23 1_455 .880 2.608 3.469(3) 166.26 y
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
O17 Cu1 N1 C2 -127.8(5)
O21 Cu1 N1 C2 -12.6(2)
N12 Cu1 N1 C2 -179.8(2)
O22 Cu1 N1 C2 82.8(2)
O17 Cu1 N1 C14 50.5(6)
O21 Cu1 N1 C14 165.70(14)
N12 Cu1 N1 C14 -1.55(14)
O22 Cu1 N1 C14 -98.92(15)
C14 N1 C2 C3 .3(4)
Cu1 N1 C2 C3 178.52(18)
N1 C2 C3 C4 -.5(4)
C2 C3 C4 C5 .5(4)
C3 C4 C5 C14 -.3(3)
C3 C4 C5 C6 -179.1(2)
C14 C5 C6 C7 1.6(3)
C4 C5 C6 C7 -179.7(2)
C14 C5 C6 C15 -177.4(2)
C4 C5 C6 C15 1.3(3)
C5 C6 C7 C8 -.7(3)
C15 C6 C7 C8 178.3(2)
C5 C6 C7 C16 178.6(2)
C15 C6 C7 C16 -2.5(4)
C6 C7 C8 C13 -1.0(3)
C16 C7 C8 C13 179.7(2)
C6 C7 C8 C9 179.6(2)
C16 C7 C8 C9 .3(3)
C13 C8 C9 C10 .4(3)
C7 C8 C9 C10 179.9(2)
C8 C9 C10 C11 -.7(3)
C9 C10 C11 N12 .3(3)
C10 C11 N12 C13 .3(3)
C10 C11 N12 Cu1 -179.65(16)
O17 Cu1 N12 C11 7.3(2)
N1 Cu1 N12 C11 -178.3(2)
O21 Cu1 N12 C11 80.5(3)
O22 Cu1 N12 C11 -86.63(19)
O17 Cu1 N12 C13 -172.69(15)
N1 Cu1 N12 C13 1.74(14)
O21 Cu1 N12 C13 -99.5(3)
O22 Cu1 N12 C13 93.38(14)
C11 N12 C13 C8 -.6(3)
Cu1 N12 C13 C8 179.42(16)
C11 N12 C13 C14 178.38(19)
Cu1 N12 C13 C14 -1.6(2)
C9 C8 C13 N12 .2(3)
C7 C8 C13 N12 -179.31(19)
C9 C8 C13 C14 -178.74(19)
C7 C8 C13 C14 1.8(3)
C2 N1 C14 C5 -.2(3)
Cu1 N1 C14 C5 -178.64(16)
C2 N1 C14 C13 179.60(19)
Cu1 N1 C14 C13 1.1(2)
C4 C5 C14 N1 .2(3)
C6 C5 C14 N1 178.97(19)
C4 C5 C14 C13 -179.61(19)
C6 C5 C14 C13 -.8(3)
N12 C13 C14 N1 .3(3)
C8 C13 C14 N1 179.34(18)
N12 C13 C14 C5 -179.87(18)
C8 C13 C14 C5 -.9(3)
N1 Cu1 O17 C18 118.1(5)
O21 Cu1 O17 C18 1.88(18)
N12 Cu1 O17 C18 169.55(18)
O22 Cu1 O17 C18 -92.58(19)
Cu1 O17 C18 O19 174.0(2)
Cu1 O17 C18 C20 -6.3(3)
O19 C18 C20 O21 -171.9(2)
O17 C18 C20 O21 8.4(3)
C18 C20 O21 Cu1 -6.4(3)
O17 Cu1 O21 C20 3.01(17)
N1 Cu1 O21 C20 -170.56(16)
N12 Cu1 O21 C20 -71.3(3)
O22 Cu1 O21 C20 95.90(17)
