#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/29/4512921.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_4512921
loop_
_publ_author_name
'Yahsi, Yasemin'
'Gungor, Elif'
'Kara, Hulya'
_publ_section_title
;
 Chlorometallate-Pyridinium Boronic Acid Salts for Crystal Engineering:
 Synthesis of One-, Two-, and Three-Dimensional Hydrogen Bond Networks
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2652
_journal_paper_doi               10.1021/cg501769b
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C10 H14 B2 Cl4 Cu N2 O4'
_chemical_formula_weight         453.19
_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                79.53(3)
_cell_angle_beta                 65.87(3)
_cell_angle_gamma                71.62(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0727(18)
_cell_length_b                   9.5234(19)
_cell_length_c                   10.835(2)
_cell_measurement_reflns_used    2159
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      2.6165
_cell_volume                     809.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SHELXTL (Bruker, 2002)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.1218
_diffrn_reflns_av_sigmaI/netI    0.1175
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8899
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.026
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.221
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1251
_reflns_number_gt                2613
_reflns_number_total             3679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501769b_si_001.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4512919--4512925.cif.
;
_cod_original_cell_volume        809.3(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4512921
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
Cu1 Cu 0.36726(6) 0.38595(6) 0.60190(5) 0.01131(17) Uani 1 1 d .
Cl1 Cl 0.11671(11) 0.37145(13) 0.62290(11) 0.0178(3) Uani 1 1 d .
Cl2 Cl 0.24274(11) 0.52524(12) 0.79412(10) 0.0135(2) Uani 1 1 d .
Cl3 Cl 0.62116(11) 0.38744(12) 0.59180(10) 0.0124(2) Uani 1 1 d .
Cl4 Cl 0.49734(11) 0.19616(12) 0.45192(10) 0.0136(2) Uani 1 1 d .
B1 B -0.0258(5) -0.0385(6) 0.2092(5) 0.0126(10) Uani 1 1 d .
B2 B 0.7721(5) 0.7734(6) 1.0239(5) 0.0127(10) Uani 1 1 d .
C1 C 0.0493(5) 0.0299(5) 0.2864(4) 0.0110(9) Uani 1 1 d .
C2 C 0.2123(5) -0.0380(5) 0.2827(4) 0.0141(9) Uani 1 1 d .
H2 H 0.2758 -0.1269 0.2373 0.017 Uiso 1 1 calc R
C3 C 0.2808(5) 0.0237(5) 0.3446(4) 0.0136(9) Uani 1 1 d .
H3 H 0.3911 -0.0220 0.3424 0.016 Uiso 1 1 calc R
C4 C 0.0319(5) 0.2185(5) 0.4158(4) 0.0142(9) Uani 1 1 d .
H4 H -0.0283 0.3076 0.4614 0.017 Uiso 1 1 calc R
C5 C -0.0407(5) 0.1583(5) 0.3568(4) 0.0129(9) Uani 1 1 d .
H5 H -0.1531 0.2044 0.3641 0.015 Uiso 1 1 calc R
C6 C 0.6960(5) 0.7043(5) 0.9489(4) 0.0127(9) Uani 1 1 d .
C7 C 0.7874(5) 0.5803(5) 0.8722(4) 0.0152(10) Uani 1 1 d .
H7 H 0.9003 0.5341 0.8632 0.018 Uiso 1 1 calc R
C8 C 0.7145(5) 0.5248(5) 0.8097(4) 0.0160(10) Uani 1 1 d .
H8 H 0.7773 0.4405 0.7574 0.019 Uiso 1 1 calc R
C9 C 0.4628(5) 0.7105(5) 0.8940(4) 0.0163(10) Uani 1 1 d .
H9 H 0.3506 0.7551 0.9002 0.020 Uiso 1 1 calc R
C10 C 0.5309(5) 0.7690(5) 0.9579(5) 0.0170(10) Uani 1 1 d .
H10 H 0.4655 0.8540 1.0087 0.020 Uiso 1 1 calc R
N1 N 0.5553(4) 0.5895(5) 0.8224(4) 0.0148(8) Uani 1 1 d U
N2 N 0.1890(4) 0.1497(4) 0.4082(4) 0.0132(8) Uani 1 1 d U
O1 O 0.0847(3) -0.1347(4) 0.1143(3) 0.0178(7) Uani 1 1 d .
H1 H 0.0325 -0.1765 0.0904 0.027 Uiso 1 1 calc R
O2 O -0.1915(3) 0.0036(4) 0.2304(3) 0.0169(7) Uani 1 1 d .
H2A H -0.2453 0.0542 0.2988 0.025 Uiso 1 1 calc R
O3 O 0.9404(3) 0.7469(3) 0.9910(3) 0.0147(7) Uani 1 1 d .
H3A H 0.9930 0.6795 0.9363 0.022 Uiso 1 1 calc R
O4 O 0.6634(3) 0.8702(4) 1.1186(3) 0.0194(8) Uani 1 1 d .
H4A H 0.7156 0.8952 1.1558 0.029 Uiso 1 1 calc R
H1A H 0.521(6) 0.561(6) 0.776(5) 0.023 Uiso 1 1 d .
H2B H 0.239(6) 0.169(6) 0.441(5) 0.023 Uiso 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'
B B 0.0013 0.0007 '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_3
Cl1 Cu1 Cl3 176.00(5) .
Cl1 Cu1 Cl4 89.71(5) .
Cl3 Cu1 Cl4 89.87(5) .
Cl1 Cu1 Cl2 90.88(5) .
Cl3 Cu1 Cl2 88.51(5) .
Cl4 Cu1 Cl2 165.14(5) .
Cl1 Cu1 Cl3 94.38(5) 2_666
Cl3 Cu1 Cl3 89.62(5) 2_666
Cl4 Cu1 Cl3 95.90(4) 2_666
Cl2 Cu1 Cl3 98.86(4) 2_666
Cu1 Cl3 Cu1 90.38(5) 2_666
O1 B1 O2 120.7(4) .
O1 B1 C1 116.8(3) .
O2 B1 C1 122.3(4) .
O4 B2 O3 119.4(4) .
O4 B2 C6 117.2(4) .
O3 B2 C6 123.3(4) .
C5 C1 C2 117.9(4) .
C5 C1 B1 122.2(4) .
C2 C1 B1 119.8(4) .
C3 C2 C1 120.2(4) .
C3 C2 H2 119.9 .
C1 C2 H2 119.9 .
N2 C3 C2 119.0(4) .
N2 C3 H3 120.5 .
C2 C3 H3 120.5 .
N2 C4 C5 119.2(4) .
N2 C4 H4 120.4 .
C5 C4 H4 120.4 .
C4 C5 C1 120.5(4) .
C4 C5 H5 119.8 .
C1 C5 H5 119.8 .
C7 C6 C10 117.6(4) .
C7 C6 B2 122.8(4) .
C10 C6 B2 119.6(4) .
C8 C7 C6 120.2(4) .
C8 C7 H7 119.9 .
C6 C7 H7 119.9 .
N1 C8 C7 120.1(4) .
N1 C8 H8 120.0 .
C7 C8 H8 120.0 .
N1 C9 C10 119.9(4) .
N1 C9 H9 120.1 .
C10 C9 H9 120.1 .
C9 C10 C6 120.4(4) .
C9 C10 H10 119.8 .
C6 C10 H10 119.8 .
C9 N1 C8 121.8(4) .
C9 N1 H1A 121(4) .
C8 N1 H1A 117(4) .
C4 N2 C3 123.2(4) .
C4 N2 H2B 129(4) .
C3 N2 H2B 108(4) .
B1 O1 H1 109.5 .
B1 O2 H2A 109.5 .
B2 O3 H3A 109.5 .
B2 O4 H4A 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cl1 2.2364(12) .
Cu1 Cl3 2.2656(11) .
Cu1 Cl4 2.3355(14) .
Cu1 Cl2 2.3472(14) .
Cu1 Cl3 2.7185(16) 2_666
Cl3 Cu1 2.7185(16) 2_666
B1 O1 1.350(5) .
B1 O2 1.358(5) .
B1 C1 1.591(6) .
B2 O4 1.349(5) .
B2 O3 1.367(5) .
B2 C6 1.584(6) .
C1 C5 1.395(5) .
C1 C2 1.402(6) .
C2 C3 1.377(6) .
C2 H2 0.9500 .
C3 N2 1.346(5) .
C3 H3 0.9500 .
C4 N2 1.342(6) .
C4 C5 1.374(6) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 C7 1.395(6) .
C6 C10 1.397(6) .
C7 C8 1.375(6) .
C7 H7 0.9500 .
C8 N1 1.339(6) .
C8 H8 0.9500 .
C9 N1 1.348(6) .
C9 C10 1.371(6) .
C9 H9 0.9500 .
C10 H10 0.9500 .
N1 H1A 0.81(6) .
N2 H2B 0.76(6) .
O1 H1 0.8400 .
O2 H2A 0.8400 .
O3 H3A 0.8400 .
O4 H4A 0.8400 .
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
Cl1 Cu1 Cl3 Cu1 180(100) . 2_666
Cl4 Cu1 Cl3 Cu1 95.90(4) . 2_666
Cl2 Cu1 Cl3 Cu1 -98.87(4) . 2_666
Cl3 Cu1 Cl3 Cu1 0.0 2_666 2_666
O1 B1 C1 C5 161.5(4) . .
O2 B1 C1 C5 -14.4(7) . .
O1 B1 C1 C2 -17.3(6) . .
O2 B1 C1 C2 166.8(4) . .
C5 C1 C2 C3 -1.5(7) . .
B1 C1 C2 C3 177.4(4) . .
C1 C2 C3 N2 -0.1(7) . .
N2 C4 C5 C1 -1.9(7) . .
C2 C1 C5 C4 2.5(7) . .
B1 C1 C5 C4 -176.4(4) . .
O4 B2 C6 C7 -165.3(4) . .
O3 B2 C6 C7 19.0(7) . .
O4 B2 C6 C10 15.1(7) . .
O3 B2 C6 C10 -160.6(5) . .
C10 C6 C7 C8 -0.6(7) . .
B2 C6 C7 C8 179.8(4) . .
C6 C7 C8 N1 -0.1(7) . .
N1 C9 C10 C6 0.2(7) . .
C7 C6 C10 C9 0.5(7) . .
B2 C6 C10 C9 -179.8(4) . .
C10 C9 N1 C8 -1.0(7) . .
C7 C8 N1 C9 1.0(7) . .
C5 C4 N2 C3 0.3(7) . .
C2 C3 N2 C4 0.7(7) . .
