#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/03/7200386.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_7200386
loop_
_publ_author_name
'Turner, David R.'
'Pek, Sze Nee'
'Batten, Stuart R.'
_publ_section_title
;
 Destabilisation of a dual-synthon hydrogen bonding motif by packing
 effects and competing hydrogen bond donors
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              87
_journal_paper_doi               10.1039/b814158d
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C14 H24 Cu1 N10 O2'
_chemical_formula_sum            'C14 H24 Cu N10 O2'
_chemical_formula_weight         427.97
_chemical_name_common            '[Cu(cdm)2(NH2(CH2)3NH2)2]'
_chemical_name_systematic
;
[Cu(cdm)2(NH2(CH2)3NH2)2]
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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            8
_cell_length_a                   17.8128(12)
_cell_length_b                   28.8740(30)
_cell_length_c                   7.1606(6)
_cell_measurement_reflns_used    5531
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.69
_cell_volume                     3682.9(6)
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_collection       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 Apex II CCD'
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5531
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.7583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2092
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0628
_refine_ls_wR_factor_ref         0.0650
_reflns_number_gt                1866
_reflns_number_total             2092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814158d.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 
;
_cod_original_sg_symbol_H-M      Fdd2
_cod_original_formula_sum        'C14 H24 Cu1 N10 O2'
_cod_database_code               7200386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.45904(6) 0.01350(11) Uani 1 2 d S . .
O1 O 0.40685(7) 0.49813(7) 0.4554(5) 0.0161(3) Uani 1 1 d . . .
N1 N 0.31100(11) 0.45058(8) 0.5288(3) 0.0183(5) Uani 1 1 d . . .
C1 C 0.28493(13) 0.52981(8) 0.4519(5) 0.0153(5) Uani 1 1 d . . .
N2 N 0.14349(12) 0.51529(7) 0.4821(4) 0.0216(5) Uani 1 1 d . . .
C2 C 0.20648(14) 0.52250(8) 0.4701(4) 0.0161(5) Uani 1 1 d . . .
N3 N 0.33290(13) 0.61013(8) 0.3581(3) 0.0228(5) Uani 1 1 d . . .
C3 C 0.31126(14) 0.57381(10) 0.4000(4) 0.0168(6) Uani 1 1 d . . .
H3N H 0.0488 0.4500 0.7210 0.050 Uiso 1 1 d . . .
H4N H -0.0329 0.4611 0.7661 0.050 Uiso 1 1 d . . .
H6N H 0.0332 0.4652 0.1613 0.050 Uiso 1 1 d . . .
H1N H 0.2665 0.4497 0.5564 0.050 Uiso 1 1 d . . .
H5N H -0.0312 0.4373 0.2161 0.050 Uiso 1 1 d . . .
H2N H 0.3406 0.4270 0.5471 0.050 Uiso 1 1 d . . .
N4 N 0.00410(11) 0.45138(9) 0.6625(4) 0.0116(6) Uani 1 1 d . . .
C4 C 0.33781(13) 0.49256(8) 0.4793(5) 0.0139(6) Uani 1 1 d . . .
N5 N 0.01475(13) 0.45116(8) 0.2601(3) 0.0133(6) Uani 1 1 d . . .
C5 C -0.01265(14) 0.40420(9) 0.5983(4) 0.0157(5) Uani 1 1 d . . .
H5A H -0.0607 0.4044 0.5289 0.019 Uiso 1 1 calc R . .
H5B H -0.0188 0.3837 0.7081 0.019 Uiso 1 1 calc R . .
C6 C 0.04850(14) 0.38481(8) 0.4733(4) 0.0180(5) Uani 1 1 d . . .
H6A H 0.0314 0.3546 0.4238 0.022 Uiso 1 1 calc R . .
H6B H 0.0936 0.3790 0.5505 0.022 Uiso 1 1 calc R . .
C7 C 0.07105(14) 0.41556(9) 0.3086(4) 0.0177(6) Uani 1 1 d . . .
H7A H 0.1191 0.4311 0.3388 0.021 Uiso 1 1 calc R . .
H7B H 0.0797 0.3957 0.1980 0.021 Uiso 1 1 calc R . .
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
_geom_angle_publ_flag
N5 Cu1 N5 90.41(14) 2_565 . ?
N5 Cu1 N4 91.07(7) 2_565 2_565 ?
N5 Cu1 N4 174.54(9) . 2_565 ?
N5 Cu1 N4 174.54(9) 2_565 . ?
N5 Cu1 N4 91.07(7) . . ?
N4 Cu1 N4 87.94(14) 2_565 . ?
N5 Cu1 N2 93.10(9) 2_565 . ?
N5 Cu1 N2 92.03(8) . . ?
N4 Cu1 N2 82.64(8) 2_565 . ?
N4 Cu1 N2 92.09(8) . . ?
N5 Cu1 N2 92.03(8) 2_565 2_565 ?
N5 Cu1 N2 93.10(9) . 2_565 ?
N4 Cu1 N2 92.09(8) 2_565 2_565 ?
N4 Cu1 N2 82.64(8) . 2_565 ?
N2 Cu1 N2 172.71(13) . 2_565 ?
C4 N1 H1N 115.8 . . ?
C4 N1 H2N 121.8 . . ?
H1N N1 H2N 121.7 . . ?
C3 C1 C2 119.2(2) . . ?
C3 C1 C4 119.5(2) . . ?
C2 C1 C4 121.3(2) . . ?
C2 N2 Cu1 172.0(3) . . ?
N2 C2 C1 177.9(3) . . ?
N3 C3 C1 179.7(3) . . ?
C5 N4 Cu1 114.23(19) . . ?
C5 N4 H3N 106.5 . . ?
Cu1 N4 H3N 113.4 . . ?
C5 N4 H4N 110.4 . . ?
Cu1 N4 H4N 107.8 . . ?
H3N N4 H4N 104.1 . . ?
O1 C4 N1 119.9(2) . . ?
O1 C4 C1 121.8(2) . . ?
N1 C4 C1 118.3(2) . . ?
C7 N5 Cu1 114.10(18) . . ?
C7 N5 H6N 104.8 . . ?
Cu1 N5 H6N 107.1 . . ?
C7 N5 H5N 111.4 . . ?
Cu1 N5 H5N 114.2 . . ?
H6N N5 H5N 104.2 . . ?
N4 C5 C6 112.4(2) . . ?
N4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 115.4(2) . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
N5 C7 C6 114.0(2) . . ?
N5 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N5 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 2.021(3) 2_565 ?
Cu1 N5 2.021(3) . ?
Cu1 N4 2.025(3) 2_565 ?
Cu1 N4 2.025(3) . ?
Cu1 N2 2.599(2) . ?
Cu1 N2 2.599(2) 2_565 ?
O1 C4 1.252(3) . ?
N1 C4 1.350(3) . ?
N1 H1N 0.8173 . ?
N1 H2N 0.8712 . ?
C1 C3 1.404(4) . ?
C1 C2 1.419(4) . ?
C1 C4 1.443(3) . ?
N2 C2 1.145(3) . ?
N3 C3 1.157(3) . ?
N4 C5 1.469(3) . ?
N4 H3N 0.9005 . ?
N4 H4N 1.0310 . ?
N5 C7 1.477(3) . ?
N5 H6N 0.8794 . ?
N5 H5N 0.9641 . ?
C5 C6 1.517(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.530(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
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
N4 H3N O1 0.90 2.38 3.007(4) 126.3 10_565
N4 H4N O1 1.03 2.03 3.037(4) 163.8 9_455
N5 H6N O1 0.88 2.11 2.976(4) 170.0 10_564
N5 H5N N3 0.96 2.53 3.335(3) 140.7 7_544
N1 H2N N3 0.87 2.40 3.274(3) 176.9 15_545
