#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/82/7008254.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_7008254
loop_
_publ_author_name
'Spingler, Bernhard'
'Da Pieve, Chiara'
_publ_section_title
;
 Induction of B- to Z-DNA transition by copper and zinc complexes with
 C(15) substituted macrocyclic pentaaza ligands.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1637
_journal_page_last               1643
_journal_paper_doi               10.1039/b500317b
_journal_year                    2005
_chemical_formula_sum            'C11 H24 Cl2 F N5 O2'
_chemical_formula_weight         348.25
_chemical_name_systematic
;
?
;
_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                82.753(12)
_cell_angle_beta                 82.007(12)
_cell_angle_gamma                65.594(11)
_cell_formula_units_Z            2
_cell_length_a                   9.2491(9)
_cell_length_b                   9.9016(10)
_cell_length_c                   10.0535(10)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    183(2)
_cell_volume                     827.88(16)
_computing_cell_refinement       'IPDS (Stoe, 1999)'
_computing_data_collection       'IPDS (Stoe, 1999)'
_computing_data_reduction        'X-RED (Stoe, 1999)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       '/f oscillation 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  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17872
_diffrn_reflns_theta_full        30.53
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_min         2.94
_diffrn_standards_interval_count 'every image'
_diffrn_standards_interval_time  15
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9198
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4567
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.4699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1541
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                3156
_reflns_number_total             4567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b500317b.txt
_cod_data_source_block           1
_cod_original_cell_volume        827.88(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7008254
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
C16 C 0.4174(3) 0.6818(3) 1.1245(3) 0.0382(5) Uani 1 1 d . . .
C2 C 0.6956(3) 0.6559(3) 1.0840(3) 0.0414(6) Uani 1 1 d . . .
H2A H 0.7170 0.5511 1.1018 0.050 Uiso 1 1 calc R . .
H2B H 0.7393 0.6838 1.1531 0.050 Uiso 1 1 calc R . .
C3 C 0.7788(3) 0.6799(3) 0.9467(3) 0.0410(6) Uani 1 1 d . . .
H3A H 0.7650 0.7831 0.9325 0.049 Uiso 1 1 calc R . .
H3B H 0.8922 0.6188 0.9465 0.049 Uiso 1 1 calc R . .
C5 C 0.8373(3) 0.5979(4) 0.7115(3) 0.0470(6) Uani 1 1 d . . .
H5A H 0.8783 0.6740 0.6849 0.056 Uiso 1 1 calc R . .
H5B H 0.9259 0.5058 0.7348 0.056 Uiso 1 1 calc R . .
C6 C 0.7630(3) 0.5774(3) 0.5955(3) 0.0447(6) Uani 1 1 d . . .
H6A H 0.8432 0.5451 0.5198 0.054 Uiso 1 1 calc R . .
H6B H 0.7220 0.5012 0.6218 0.054 Uiso 1 1 calc R . .
C8 C 0.5341(4) 0.7027(4) 0.4623(3) 0.0489(7) Uani 1 1 d . . .
H8A H 0.5100 0.6165 0.4916 0.059 Uiso 1 1 calc R . .
H8B H 0.5915 0.6883 0.3733 0.059 Uiso 1 1 calc R . .
C9 C 0.3800(3) 0.8415(4) 0.4564(3) 0.0479(7) Uani 1 1 d . . .
H9A H 0.4037 0.9251 0.4158 0.058 Uiso 1 1 calc R . .
H9B H 0.3112 0.8271 0.4001 0.058 Uiso 1 1 calc R . .
C11 C 0.2407(3) 0.7594(3) 0.6631(3) 0.0429(6) Uani 1 1 d . . .
H11A H 0.3304 0.6773 0.7004 0.052 Uiso 1 1 calc R . .
H11B H 0.2014 0.7212 0.5983 0.052 Uiso 1 1 calc R . .
C12 C 0.1088(3) 0.8233(4) 0.7761(3) 0.0463(6) Uani 1 1 d . . .
H12A H 0.0305 0.9175 0.7423 0.056 Uiso 1 1 calc R . .
H12B H 0.0558 0.7560 0.8014 0.056 Uiso 1 1 calc R . .
C14 C 0.1694(3) 0.7611(3) 1.0105(3) 0.0386(5) Uani 1 1 d . . .
C15 C 0.2411(3) 0.7915(3) 1.1248(3) 0.0402(5) Uani 1 1 d . . .
H15 H 0.1835 0.7752 1.2105 0.048 Uiso 1 1 calc R . .
N1 N 0.5234(3) 0.7423(3) 1.0917(2) 0.0395(5) Uani 1 1 d . . .
H1 H 0.489(4) 0.836(4) 1.074(4) 0.056(10) Uiso 1 1 d . . .
N4 N 0.7167(3) 0.6426(3) 0.8327(2) 0.0380(5) Uani 1 1 d . . .
H4A H 0.630(4) 0.726(4) 0.809(3) 0.047(9) Uiso 1 1 d . . .
H4B H 0.682(4) 0.569(4) 0.860(4) 0.059(10) Uiso 1 1 d . . .
N7 N 0.6331(3) 0.7174(3) 0.5558(2) 0.0425(5) Uani 1 1 d . . .
H7 H 0.674(4) 0.790(4) 0.524(4) 0.056(10) Uiso 1 1 d . . .
N10 N 0.2951(3) 0.8755(3) 0.5933(2) 0.0390(5) Uani 1 1 d D . .
H10A H 0.358(4) 0.888(4) 0.645(3) 0.055(10) Uiso 1 1 d D . .
H10B H 0.213(4) 0.966(3) 0.586(5) 0.081(13) Uiso 1 1 d D . .
N13 N 0.1659(3) 0.8465(3) 0.8952(2) 0.0430(5) Uani 1 1 d . . .
H13 H 0.212(4) 0.905(4) 0.892(4) 0.047(9) Uiso 1 1 d . . .
O16 O 0.4504(2) 0.5473(2) 1.1523(2) 0.0482(5) Uani 1 1 d . . .
O14 O 0.1212(2) 0.6604(2) 1.0287(2) 0.0460(5) Uani 1 1 d . . .
F1 F 0.2281(2) 0.93796(19) 1.11150(19) 0.0497(4) Uani 1 1 d . . .
Cl1 Cl 0.44286(8) 0.97504(7) 0.81074(7) 0.04232(18) Uani 1 1 d . . .
Cl2 Cl 0.03303(9) 1.19388(8) 0.57271(8) 0.0538(2) Uani 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'
F F 0.0171 0.0103 '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'
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
O16 C16 N1 125.3(3) . . ?
O16 C16 C15 119.3(2) . . ?
N1 C16 C15 115.4(2) . . ?
N1 C2 C3 112.3(2) . . ?
N1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
N4 C3 C2 113.1(2) . . ?
N4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
N4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C6 C5 N4 110.9(2) . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
N4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N7 C6 C5 110.0(2) . . ?
N7 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N7 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N7 C8 C9 110.1(2) . . ?
N7 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N7 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
N10 C9 C8 111.4(2) . . ?
N10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N10 C11 C12 111.1(2) . . ?
N10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N13 C12 C11 113.7(2) . . ?
N13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
N13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O14 C14 N13 124.8(3) . . ?
O14 C14 C15 118.8(2) . . ?
N13 C14 C15 116.3(2) . . ?
F1 C15 C14 111.0(2) . . ?
F1 C15 C16 110.5(2) . . ?
C14 C15 C16 108.8(2) . . ?
F1 C15 H15 108.8 . . ?
C14 C15 H15 108.8 . . ?
C16 C15 H15 108.8 . . ?
C16 N1 C2 123.3(2) . . ?
C16 N1 H1 118(3) . . ?
C2 N1 H1 118(3) . . ?
C3 N4 C5 113.3(2) . . ?
C3 N4 H4A 107(2) . . ?
C5 N4 H4A 109(2) . . ?
C3 N4 H4B 111(2) . . ?
C5 N4 H4B 109(2) . . ?
H4A N4 H4B 107(3) . . ?
C8 N7 C6 114.1(2) . . ?
C8 N7 H7 113(2) . . ?
C6 N7 H7 110(2) . . ?
C9 N10 C11 114.7(2) . . ?
C9 N10 H10A 109(2) . . ?
C11 N10 H10A 109(2) . . ?
C9 N10 H10B 108(3) . . ?
C11 N10 H10B 111(3) . . ?
H10A N10 H10B 104(4) . . ?
C14 N13 C12 121.8(2) . . ?
C14 N13 H13 116(2) . . ?
C12 N13 H13 121(2) . . ?
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
C16 O16 1.240(3) . ?
C16 N1 1.332(3) . ?
C16 C15 1.541(4) . ?
C2 N1 1.460(3) . ?
C2 C3 1.526(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.498(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.507(4) . ?
C5 N4 1.508(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N7 1.464(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 N7 1.458(4) . ?
C8 C9 1.519(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N10 1.491(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 N10 1.498(3) . ?
C11 C12 1.528(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N13 1.453(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 O14 1.234(3) . ?
C14 N13 1.342(3) . ?
C14 C15 1.522(4) . ?
C15 F1 1.395(3) . ?
C15 H15 0.9800 . ?
N1 H1 0.85(4) . ?
N4 H4A 0.92(4) . ?
N4 H4B 0.91(4) . ?
N7 H7 0.95(4) . ?
N10 H10A 0.884(19) . ?
N10 H10B 0.905(19) . ?
N13 H13 0.85(4) . ?
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 H1 Cl1 0.85(4) 2.64(4) 3.223(2) 127(3) 2_677
N4 H4A Cl1 0.92(4) 2.36(4) 3.222(2) 158(3) .
N4 H4B O16 0.91(4) 2.02(4) 2.866(3) 154(3) 2_667
N10 H10A Cl1 0.884(19) 2.33(2) 3.179(3) 161(3) .
N10 H10B Cl2 0.905(19) 2.18(2) 3.085(2) 174(4) .
N13 H13 Cl1 0.85(4) 2.51(4) 3.274(2) 151(3) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N4 -57.6(3) . . . . ?
N4 C5 C6 N7 61.4(3) . . . . ?
N7 C8 C9 N10 -54.1(3) . . . . ?
N10 C11 C12 N13 -74.8(3) . . . . ?
O14 C14 C15 F1 -155.4(2) . . . . ?
N13 C14 C15 F1 25.5(3) . . . . ?
O14 C14 C15 C16 82.8(3) . . . . ?
N13 C14 C15 C16 -96.3(3) . . . . ?
O16 C16 C15 F1 171.0(2) . . . . ?
N1 C16 C15 F1 -9.8(3) . . . . ?
O16 C16 C15 C14 -66.9(3) . . . . ?
N1 C16 C15 C14 112.3(3) . . . . ?
O16 C16 N1 C2 0.2(4) . . . . ?
C15 C16 N1 C2 -179.0(2) . . . . ?
C3 C2 N1 C16 123.9(3) . . . . ?
C2 C3 N4 C5 -153.7(2) . . . . ?
C6 C5 N4 C3 -174.1(2) . . . . ?
C9 C8 N7 C6 164.9(2) . . . . ?
C5 C6 N7 C8 -168.8(2) . . . . ?
C8 C9 N10 C11 -63.3(3) . . . . ?
C12 C11 N10 C9 -160.2(2) . . . . ?
O14 C14 N13 C12 -2.5(4) . . . . ?
C15 C14 N13 C12 176.5(2) . . . . ?
C11 C12 N13 C14 -109.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21145204
