#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/79/7207980.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_7207980
loop_
_publ_author_name
'Cheng, Lin'
'Zhang, Limin'
'Gou, Shaohua'
'Cao, Qingna'
'Wang, Jianquan'
'Fang, Lei'
_publ_section_title
;
 Metal-directed one-dimensional chiral zigzag chains and right-handed 61
 helix with multiple chiral components: luminescence and NLO properties
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3888
_journal_paper_doi               10.1039/c2ce25043h
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C9 H13 Cu0.5 N2.5 O2'
_chemical_formula_weight         219.99
_chemical_name_systematic
;
?
;
_space_group_IT_number           178
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61 2 (0 0 5)'
_symmetry_space_group_name_H-M   'P 61 2 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                120.00
_cell_formula_units_Z            12
_cell_length_a                   13.9773(8)
_cell_length_b                   13.9773(8)
_cell_length_c                   18.263(2)
_cell_measurement_temperature    293(2)
_cell_volume                     3089.9(4)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997);
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17194
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_T_max  0.6109
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0840P)²+0.4579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                1758
_reflns_number_total             2024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25043h.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Hexagonal' changed to 'hexagonal'
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        3089.8(4)
_cod_original_sg_symbol_H-M      P6(1)22
_cod_original_formula_sum        'C9 H13 Cu0.50 N2.50 O2'
_cod_database_code               7207980
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
'y, x, -z+1/3'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'-y, -x, -z+5/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/6'
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
Cu1 Cu -0.67469(3) 0.0000 0.0000 0.04935(12) Uani 1 2 d S
N1 N -0.82884(17) -0.12692(19) 0.02955(12) 0.0529(6) Uani 1 1 d .
N2 N -0.97090(17) -0.42465(15) -0.09030(11) 0.0465(5) Uani 1 1 d .
H2B H -0.8973 -0.3969 -0.0925 0.056 Uiso 1 1 d R
C1 C -0.8678(2) -0.2301(2) 0.00465(15) 0.0514(6) Uani 1 1 d .
H1A H -0.8208 -0.2446 -0.0232 0.062 Uiso 1 1 calc R
C2 C -0.8968(2) -0.1081(3) 0.07200(15) 0.0590(7) Uani 1 1 d .
H2A H -0.8716 -0.0369 0.0895 0.071 Uiso 1 1 calc R
C3 C -1.0019(2) -0.1897(3) 0.09062(16) 0.0676(8) Uani 1 1 d .
H3A H -1.0456 -0.1742 0.1212 0.081 Uiso 1 1 calc R
C4 C -1.0413(2) -0.2953(3) 0.06299(15) 0.0625(8) Uani 1 1 d .
H4A H -1.1123 -0.3512 0.0747 0.075 Uiso 1 1 calc R
C5 C -0.9752(2) -0.3174(2) 0.01804(14) 0.0516(7) Uani 1 1 d .
C6 C -1.0169(3) -0.4314(2) -0.01564(15) 0.0620(8) Uani 1 1 d .
H6A H -0.9964 -0.4742 0.0158 0.074 Uiso 1 1 calc R
H6B H -1.0969 -0.4695 -0.0184 0.074 Uiso 1 1 calc R
C7 C -1.0198(2) -0.53536(19) -0.12622(14) 0.0489(6) Uani 1 1 d .
H7A H -1.1004 -0.5691 -0.1258 0.059 Uiso 1 1 calc R
C8 C -0.9892(3) -0.6139(2) -0.08628(18) 0.0688(8) Uani 1 1 d .
H8A H -0.9097 -0.5771 -0.0800 0.083 Uiso 1 1 calc R
H8B H -1.0227 -0.6308 -0.0380 0.083 Uiso 1 1 calc R
C9 C -1.0281(3) -0.7217(3) -0.1289(2) 0.0779(9) Uani 1 1 d .
H9A H -1.1077 -0.7599 -0.1346 0.094 Uiso 1 1 calc R
H9B H -1.0086 -0.7697 -0.1023 0.094 Uiso 1 1 calc R
N3 N -0.65354(19) -0.34646(19) -0.0833 0.168(4) Uani 1 2 d SD
O1 O -0.70106(16) -0.29894(16) -0.0833 0.1207(16) Uani 1 2 d SD
O2 O -0.6825(5) -0.4305(4) -0.1191(4) 0.299(5) Uani 1 1 d D
O1W O -0.7661(17) -0.3830(8) 0.0833 1.01(2) Uani 1 2 d S
H1WA H -0.7490 -0.3608 0.0394 1.211 Uiso 1 1 d 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'
Cu Cu 0.3201 1.2651 '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'
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
N1 Cu1 N1 104.20(15) 8 .
N1 Cu1 N2 120.23(8) 8 6_565
N1 Cu1 N2 114.08(9) . 6_565
N1 Cu1 N2 114.08(9) 8 10_444
N1 Cu1 N2 120.23(8) . 10_444
N2 Cu1 N2 84.20(11) 6_565 10_444
C1 N1 C2 117.2(2) . .
C1 N1 Cu1 121.59(18) . .
C2 N1 Cu1 121.11(19) . .
C6 N2 C7 112.12(19) . .
C6 N2 Cu1 114.85(19) . 5_444
C7 N2 Cu1 104.38(14) . 5_444
C6 N2 H2B 115.6 . .
C7 N2 H2B 105.0 . .
Cu1 N2 H2B 103.7 5_444 .
N1 C1 C5 124.0(3) . .
N1 C1 H1A 118.0 . .
C5 C1 H1A 118.0 . .
N1 C2 C3 122.9(3) . .
N1 C2 H2A 118.5 . .
C3 C2 H2A 118.5 . .
C2 C3 C4 118.9(3) . .
C2 C3 H3A 120.5 . .
C4 C3 H3A 120.5 . .
C5 C4 C3 120.0(3) . .
C5 C4 H4A 120.0 . .
C3 C4 H4A 120.0 . .
C4 C5 C1 116.9(2) . .
C4 C5 C6 121.6(2) . .
C1 C5 C6 121.5(2) . .
N2 C6 C5 112.0(2) . .
N2 C6 H6A 109.2 . .
C5 C6 H6A 109.2 . .
N2 C6 H6B 109.2 . .
C5 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
N2 C7 C8 112.5(2) . .
N2 C7 C7 107.17(16) . 9_344
C8 C7 C7 112.01(18) . 9_344
N2 C7 H7A 108.4 . .
C8 C7 H7A 108.4 . .
C7 C7 H7A 108.4 9_344 .
C9 C8 C7 111.7(3) . .
C9 C8 H8A 109.3 . .
C7 C8 H8A 109.3 . .
C9 C8 H8B 109.3 . .
C7 C8 H8B 109.3 . .
H8A C8 H8B 107.9 . .
C8 C9 C9 108.6(2) . 9_344
C8 C9 H9A 110.0 . .
C9 C9 H9A 110.0 9_344 .
C8 C9 H9B 110.0 . .
C9 C9 H9B 110.0 9_344 .
H9A C9 H9B 108.3 . .
O1 N3 O2 123.1(4) . 10_444
O1 N3 O2 123.1(4) . .
O2 N3 O2 113.9(8) 10_444 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.063(2) 8
Cu1 N1 2.063(2) .
Cu1 N2 2.145(2) 6_565
Cu1 N2 2.145(2) 10_444
N1 C1 1.340(4) .
N1 C2 1.350(4) .
N2 C6 1.490(3) .
N2 C7 1.495(3) .
N2 Cu1 2.145(2) 5_444
N2 H2B 0.9002 .
C1 C5 1.404(3) .
C1 H1A 0.9300 .
C2 C3 1.378(4) .
C2 H2A 0.9300 .
C3 C4 1.387(5) .
C3 H3A 0.9300 .
C4 C5 1.383(4) .
C4 H4A 0.9300 .
C5 C6 1.525(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.546(4) .
C7 C7 1.553(5) 9_344
C7 H7A 0.9800 .
C8 C9 1.534(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C9 1.539(7) 9_344
C9 H9A 0.9700 .
C9 H9B 0.9700 .
N3 O1 1.150(5) .
N3 O2 1.222(5) 10_444
N3 O2 1.222(5) .
O1W H1WA 0.8503 .
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
N2 H2B O1 0.90 2.38 3.271(3) 169.7
O1W H1WA O1 0.85 2.38 3.225(5) 179.9
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
N1 Cu1 N1 C1 132.4(3) 8 .
N2 Cu1 N1 C1 -94.6(2) 6_565 .
N2 Cu1 N1 C1 3.0(3) 10_444 .
N1 Cu1 N1 C2 -44.3(2) 8 .
N2 Cu1 N1 C2 88.7(2) 6_565 .
N2 Cu1 N1 C2 -173.7(2) 10_444 .
C2 N1 C1 C5 2.3(4) . .
Cu1 N1 C1 C5 -174.6(2) . .
C1 N1 C2 C3 0.6(4) . .
Cu1 N1 C2 C3 177.4(2) . .
N1 C2 C3 C4 -2.0(5) . .
C2 C3 C4 C5 0.5(5) . .
C3 C4 C5 C1 2.0(4) . .
C3 C4 C5 C6 -177.8(3) . .
N1 C1 C5 C4 -3.6(4) . .
N1 C1 C5 C6 176.3(3) . .
C7 N2 C6 C5 -174.6(2) . .
Cu1 N2 C6 C5 -55.7(3) 5_444 .
C4 C5 C6 N2 145.2(3) . .
C1 C5 C6 N2 -34.6(4) . .
C6 N2 C7 C8 -65.4(3) . .
Cu1 N2 C7 C8 169.70(18) 5_444 .
C6 N2 C7 C7 171.1(2) . 9_344
Cu1 N2 C7 C7 46.2(2) 5_444 9_344
N2 C7 C8 C9 -173.1(2) . .
C7 C7 C8 C9 -52.3(3) 9_344 .
C7 C8 C9 C9 60.3(4) . 9_344
