#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:21:06 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180334 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/03/7200384.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_7200384
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         'C32 H20 Cl2 Cu2 N10 O2, 2(C H4 O)'
_chemical_formula_sum            'C34 H28 Cl2 Cu2 N10 O4'
_chemical_formula_weight         838.64
_chemical_name_common            '[Cu(cdm)Cl(1,10-phen)]2.2MeOH'
_chemical_name_systematic
;
[(carbamoyldicyanomethanide)(chloro)(1,10-phenanthroline)copper(II)]
methanol solvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                108.736(5)
_cell_angle_beta                 91.509(5)
_cell_angle_gamma                99.329(5)
_cell_formula_units_Z            1
_cell_length_a                   7.4044(7)
_cell_length_b                   9.9340(9)
_cell_length_c                   12.0617(13)
_cell_measurement_reflns_used    4985
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.20
_cell_volume                     826.15(14)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4985
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.507
_exptl_absorpt_correction_T_max  0.9150
_exptl_absorpt_correction_T_min  0.7328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_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          0.0717
_refine_ls_wR_factor_ref         0.0759
_reflns_number_gt                2465
_reflns_number_total             2864
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814158d.txt
_cod_data_source_block           2
_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      P-1
_cod_database_code               7200384
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.57927(5) 0.66570(4) 0.80510(3) 0.01211(12) Uani 1 1 d . . .
Cl1 Cl 0.49885(11) 0.87839(7) 0.82208(7) 0.0253(2) Uani 1 1 d . . .
O1 O 0.0664(3) 0.7194(2) 0.40236(18) 0.0215(5) Uani 1 1 d . . .
N1 N 0.2163(4) 0.8313(3) 0.5822(2) 0.0185(6) Uani 1 1 d . . .
C1 C 0.2213(4) 0.5801(3) 0.4834(3) 0.0127(6) Uani 1 1 d . . .
H1N H 0.195(4) 0.913(4) 0.582(3) 0.025(9) Uiso 1 1 d . . .
H1O H -0.134(4) 0.839(3) 0.430(3) 0.010(9) Uiso 1 1 d . . .
O2 O -0.2030(3) 0.8835(2) 0.43693(19) 0.0200(5) Uani 1 1 d . . .
N2 N 0.4120(3) 0.5789(2) 0.6614(2) 0.0167(5) Uani 1 1 d . . .
C2 C 0.3255(4) 0.5733(3) 0.5783(3) 0.0133(6) Uani 1 1 d . . .
H2N H 0.283(5) 0.831(4) 0.639(3) 0.030(10) Uiso 1 1 d . . .
N3 N 0.1481(3) 0.3565(3) 0.2998(2) 0.0177(5) Uani 1 1 d . . .
C3 C 0.1762(4) 0.4572(3) 0.3831(3) 0.0141(6) Uani 1 1 d . . .
N4 N 0.5921(3) 0.4757(2) 0.8280(2) 0.0113(5) Uani 1 1 d . . .
C4 C 0.1630(4) 0.7146(3) 0.4868(3) 0.0152(6) Uani 1 1 d . . .
N5 N 0.7279(3) 0.7435(2) 0.9614(2) 0.0123(5) Uani 1 1 d . . .
C5 C 0.5239(4) 0.3432(3) 0.7574(3) 0.0143(6) Uani 1 1 d . . .
H5 H 0.4584 0.3310 0.6850 0.017 Uiso 1 1 calc R . .
C6 C 0.5453(4) 0.2210(3) 0.7861(3) 0.0155(6) Uani 1 1 d . . .
H6 H 0.4953 0.1272 0.7337 0.019 Uiso 1 1 calc R . .
C7 C 0.6388(4) 0.2372(3) 0.8902(3) 0.0158(6) Uani 1 1 d . . .
H7 H 0.6530 0.1545 0.9106 0.019 Uiso 1 1 calc R . .
C8 C 0.7138(4) 0.3757(3) 0.9668(3) 0.0136(6) Uani 1 1 d . . .
C9 C 0.8152(4) 0.4061(3) 1.0774(3) 0.0152(6) Uani 1 1 d . . .
H9 H 0.8329 0.3283 1.1036 0.018 Uiso 1 1 calc R . .
C10 C 0.8859(4) 0.5422(3) 1.1452(3) 0.0156(6) Uani 1 1 d . . .
H10 H 0.9532 0.5584 1.2178 0.019 Uiso 1 1 calc R . .
C11 C 0.8617(3) 0.6634(3) 1.1098(2) 0.0127(6) Uani 1 1 d . . .
C12 C 0.9346(4) 0.8086(3) 1.1743(3) 0.0159(6) Uani 1 1 d . . .
H12 H 1.0063 0.8323 1.2467 0.019 Uiso 1 1 calc R . .
C13 C 0.9015(4) 0.9153(3) 1.1319(3) 0.0162(6) Uani 1 1 d . . .
H13 H 0.9496 1.0136 1.1750 0.019 Uiso 1 1 calc R . .
C14 C 0.7967(4) 0.8789(3) 1.0252(3) 0.0140(6) Uani 1 1 d . . .
H1 H 0.7738 0.9543 0.9972 0.017 Uiso 1 1 calc R . .
C15 C 0.7609(3) 0.6366(3) 1.0028(2) 0.0117(6) Uani 1 1 d . . .
C16 C 0.6866(3) 0.4919(3) 0.9307(2) 0.0107(6) Uani 1 1 d . . .
C17 C -0.2770(5) 0.8871(4) 0.5453(3) 0.0291(8) Uani 1 1 d . . .
H17A H -0.1766 0.9071 0.6061 0.044 Uiso 1 1 calc R . .
H17B H -0.3541 0.7936 0.5361 0.044 Uiso 1 1 calc R . .
H17C H -0.3514 0.9632 0.5683 0.044 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'
Cl Cl 0.1484 0.1585 '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
N2 Cu1 N4 94.29(10) . . ?
N2 Cu1 N5 173.30(10) . . ?
N4 Cu1 N5 82.14(9) . . ?
N2 Cu1 Cl1 88.51(7) . . ?
N4 Cu1 Cl1 161.56(7) . . ?
N5 Cu1 Cl1 93.13(7) . . ?
N2 Cu1 N3 93.65(9) . 2_666 ?
N4 Cu1 N3 88.58(8) . 2_666 ?
N5 Cu1 N3 91.93(9) . 2_666 ?
Cl1 Cu1 N3 109.46(6) . 2_666 ?
C4 N1 H1N 119(2) . . ?
C4 N1 H2N 123(2) . . ?
H1N N1 H2N 117(3) . . ?
C2 C1 C3 119.4(2) . . ?
C2 C1 C4 120.5(3) . . ?
C3 C1 C4 120.1(3) . . ?
C17 O2 H1O 106(3) . . ?
C2 N2 Cu1 158.1(2) . . ?
N2 C2 C1 174.7(3) . . ?
C3 N3 Cu1 110.2(2) . 2_666 ?
N3 C3 C1 176.7(3) . . ?
C5 N4 C16 118.5(2) . . ?
C5 N4 Cu1 128.93(19) . . ?
C16 N4 Cu1 112.53(18) . . ?
O1 C4 N1 121.5(3) . . ?
O1 C4 C1 120.2(3) . . ?
N1 C4 C1 118.2(3) . . ?
C14 N5 C15 118.2(2) . . ?
C14 N5 Cu1 129.50(19) . . ?
C15 N5 Cu1 112.33(18) . . ?
N4 C5 C6 122.0(3) . . ?
N4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C16 C8 C7 116.6(3) . . ?
C16 C8 C9 118.3(3) . . ?
C7 C8 C9 125.1(3) . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C15 C11 C12 117.0(3) . . ?
C15 C11 C10 118.3(3) . . ?
C12 C11 C10 124.7(3) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
N5 C14 C13 122.5(3) . . ?
N5 C14 H1 118.8 . . ?
C13 C14 H1 118.8 . . ?
N5 C15 C11 123.1(3) . . ?
N5 C15 C16 116.5(2) . . ?
C11 C15 C16 120.4(2) . . ?
N4 C16 C8 123.3(3) . . ?
N4 C16 C15 116.5(2) . . ?
C8 C16 C15 120.2(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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 N2 1.965(3) . ?
Cu1 N4 2.010(2) . ?
Cu1 N5 2.010(2) . ?
Cu1 Cl1 2.2354(8) . ?
Cu1 N3 2.413(2) 2_666 ?
O1 C4 1.247(3) . ?
N1 C4 1.340(4) . ?
N1 H1N 0.86(3) . ?
N1 H2N 0.83(4) . ?
C1 C2 1.389(4) . ?
C1 C3 1.401(4) . ?
C1 C4 1.459(4) . ?
O2 C17 1.423(4) . ?
O2 H1O 0.72(3) . ?
N2 C2 1.156(4) . ?
N3 C3 1.153(4) . ?
N3 Cu1 2.413(2) 2_666 ?
N4 C5 1.324(4) . ?
N4 C16 1.357(4) . ?
N5 C14 1.324(4) . ?
N5 C15 1.361(3) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(4) . ?
C7 H7 0.9500 . ?
C8 C16 1.398(4) . ?
C8 C9 1.432(4) . ?
C9 C10 1.344(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.435(4) . ?
C10 H10 0.9500 . ?
C11 C15 1.400(4) . ?
C11 C12 1.408(4) . ?
C12 C13 1.367(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(4) . ?
C13 H13 0.9500 . ?
C14 H1 0.9500 . ?
C15 C16 1.429(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
N1 H1N O2 0.86(3) 2.09(4) 2.932(4) 166(3) 2_576
O2 H1O O1 0.72(3) 2.02(3) 2.733(3) 177(3) .
N1 H2N Cl1 0.83(4) 2.56(4) 3.386(3) 170(3) .
