#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:34:44 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179902 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/98/7019829.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_7019829
loop_
_publ_author_name
'Winkelhaus, Daniel'
'Neumann, Beate'
'Stammler, Hans-Georg'
'Mitzel, Norbert W.'
_publ_section_title
;
 Intramolecular Lewis acid-base pairs based on 4-ethynyl-2,6-lutidine.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9143
_journal_page_last               9150
_journal_paper_doi               10.1039/c2dt30719g
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C16 H21 Ga N'
_chemical_formula_sum            'C16 H21 Ga N'
_chemical_formula_weight         297.06
_chemical_name_systematic        ?
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 119.238(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   24.6455(10)
_cell_length_b                   15.5940(7)
_cell_length_c                   17.8708(8)
_cell_measurement_reflns_used    64086
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     5993.1(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect, Bruker AXS, 2004'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13304
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    1.820
_exptl_absorpt_correction_T_max  0.8987
_exptl_absorpt_correction_T_min  0.7847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo and Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.705
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         6848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0433
_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)+(0.0367P)²+4.5147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                4270
_reflns_number_total             6848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30719g.txt
_cod_data_source_block           compound7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7019829
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Ga1 Ga 0.379894(14) 0.43507(2) 0.27678(2) 0.02564(10) Uani 1 1 d .
Ga2 Ga 0.639400(14) -0.06411(2) 0.46272(2) 0.02544(10) Uani 1 1 d .
N1 N 0.57819(11) 0.82693(16) 0.41471(16) 0.0241(6) Uani 1 1 d .
N2 N 0.43803(11) 0.32412(15) 0.32192(16) 0.0233(6) Uani 1 1 d .
C1 C 0.43798(15) 0.5346(2) 0.3138(2) 0.0273(7) Uani 1 1 d .
C2 C 0.46777(15) 0.6010(2) 0.3300(2) 0.0296(7) Uani 1 1 d .
C3 C 0.50466(14) 0.6775(2) 0.35657(19) 0.0268(7) Uani 1 1 d .
C4 C 0.56503(14) 0.6792(2) 0.3698(2) 0.0281(7) Uani 1 1 d .
H4 H 0.5821 0.6294 0.3586 0.034 Uiso 1 1 calc R
C5 C 0.60064(14) 0.7529(2) 0.3991(2) 0.0269(7) Uani 1 1 d .
C6 C 0.51895(14) 0.8250(2) 0.4026(2) 0.0271(7) Uani 1 1 d .
C7 C 0.48249(15) 0.7527(2) 0.3738(2) 0.0296(7) Uani 1 1 d .
H7 H 0.4414 0.7542 0.3654 0.035 Uiso 1 1 calc R
C8 C 0.66691(15) 0.7498(2) 0.4169(2) 0.0357(8) Uani 1 1 d .
H8A H 0.6703 0.7805 0.3715 0.054 Uiso 1 1 calc R
H8B H 0.6796 0.6900 0.4185 0.054 Uiso 1 1 calc R
H8C H 0.6940 0.7771 0.4723 0.054 Uiso 1 1 calc R
C9 C 0.49337(15) 0.9033(2) 0.4231(2) 0.0344(8) Uani 1 1 d .
H9A H 0.5236 0.9247 0.4800 0.052 Uiso 1 1 calc R
H9B H 0.4545 0.8887 0.4226 0.052 Uiso 1 1 calc R
H9C H 0.4853 0.9478 0.3801 0.052 Uiso 1 1 calc R
C10 C 0.33292(16) 0.4250(2) 0.3410(2) 0.0369(8) Uani 1 1 d .
H10A H 0.3496 0.4683 0.3874 0.044 Uiso 1 1 calc R
H10B H 0.2890 0.4403 0.3014 0.044 Uiso 1 1 calc R
C11 C 0.33366(18) 0.3385(2) 0.3807(3) 0.0456(9) Uani 1 1 d .
H11A H 0.3167 0.2946 0.3358 0.068 Uiso 1 1 calc R
H11B H 0.3083 0.3415 0.4091 0.068 Uiso 1 1 calc R
H11C H 0.3765 0.3235 0.4230 0.068 Uiso 1 1 calc R
C12 C 0.34024(15) 0.4488(2) 0.1503(2) 0.0310(7) Uani 1 1 d .
H12A H 0.3093 0.4025 0.1226 0.037 Uiso 1 1 calc R
H12B H 0.3176 0.5041 0.1341 0.037 Uiso 1 1 calc R
C13 C 0.38581(16) 0.4467(2) 0.1150(2) 0.0374(8) Uani 1 1 d .
H13A H 0.4217 0.4832 0.1504 0.056 Uiso 1 1 calc R
H13B H 0.3650 0.4678 0.0558 0.056 Uiso 1 1 calc R
H13C H 0.3999 0.3876 0.1163 0.056 Uiso 1 1 calc R
C14 C 0.58393(14) 0.03771(19) 0.4278(2) 0.0268(7) Uani 1 1 d .
C15 C 0.55429(13) 0.1035(2) 0.40581(19) 0.0253(7) Uani 1 1 d .
C16 C 0.51527(13) 0.17869(19) 0.3784(2) 0.0243(7) Uani 1 1 d .
C17 C 0.52979(14) 0.2530(2) 0.4283(2) 0.0266(7) Uani 1 1 d .
H17 H 0.5668 0.2550 0.4822 0.032 Uiso 1 1 calc R
C18 C 0.49092(13) 0.3235(2) 0.39998(19) 0.0253(7) Uani 1 1 d .
C19 C 0.42207(14) 0.25025(19) 0.2747(2) 0.0255(7) Uani 1 1 d .
C20 C 0.45946(14) 0.17864(19) 0.3008(2) 0.0262(7) Uani 1 1 d .
H20 H 0.4472 0.1288 0.2657 0.031 Uiso 1 1 calc R
C21 C 0.50634(15) 0.4005(2) 0.4568(2) 0.0309(7) Uani 1 1 d .
H21A H 0.5170 0.4486 0.4311 0.046 Uiso 1 1 calc R
H21B H 0.5418 0.3874 0.5132 0.046 Uiso 1 1 calc R
H21C H 0.4703 0.4160 0.4633 0.046 Uiso 1 1 calc R
C22 C 0.36014(14) 0.2460(2) 0.1934(2) 0.0320(8) Uani 1 1 d .
H22A H 0.3278 0.2702 0.2040 0.048 Uiso 1 1 calc R
H22B H 0.3501 0.1861 0.1753 0.048 Uiso 1 1 calc R
H22C H 0.3623 0.2790 0.1483 0.048 Uiso 1 1 calc R
C23 C 0.68467(18) -0.0478(2) 0.3980(3) 0.0437(9) Uani 1 1 d .
H23A H 0.7066 0.0079 0.4148 0.052 Uiso 1 1 calc R
H23B H 0.7166 -0.0933 0.4153 0.052 Uiso 1 1 calc R
C24 C 0.6452(2) -0.0496(3) 0.3021(3) 0.0697(14) Uani 1 1 d .
H24A H 0.6267 -0.1067 0.2838 0.105 Uiso 1 1 calc R
H24B H 0.6710 -0.0367 0.2757 0.105 Uiso 1 1 calc R
H24C H 0.6121 -0.0067 0.2841 0.105 Uiso 1 1 calc R
C25 C 0.68315(15) -0.0878(2) 0.5873(2) 0.0329(8) Uani 1 1 d .
H25A H 0.7084 -0.1403 0.5976 0.040 Uiso 1 1 calc R
H25B H 0.7123 -0.0399 0.6167 0.040 Uiso 1 1 calc R
C26 C 0.64276(17) -0.0998(3) 0.6289(2) 0.0454(9) Uani 1 1 d .
H26A H 0.6183 -0.0476 0.6212 0.068 Uiso 1 1 calc R
H26B H 0.6692 -0.1110 0.6903 0.068 Uiso 1 1 calc R
H26C H 0.6146 -0.1484 0.6022 0.068 Uiso 1 1 calc R
C27 C 0.68729(15) 0.8223(2) 0.1283(3) 0.0424(9) Uani 1 1 d .
H27 H 0.6808 0.8816 0.1331 0.051 Uiso 1 1 calc R
C28 C 0.68945(16) 0.7656(3) 0.1887(2) 0.0453(10) Uani 1 1 d .
H28 H 0.6853 0.7862 0.2357 0.054 Uiso 1 1 calc R
C29 C 0.69771(16) 0.6788(3) 0.1816(2) 0.0441(9) Uani 1 1 d .
H29 H 0.6983 0.6396 0.2227 0.053 Uiso 1 1 calc R
C30 C 0.70507(15) 0.6495(2) 0.1137(2) 0.0402(9) Uani 1 1 d .
H30 H 0.7112 0.5902 0.1082 0.048 Uiso 1 1 calc R
C31 C 0.70334(15) 0.7072(2) 0.0543(2) 0.0373(8) Uani 1 1 d .
H31 H 0.7084 0.6874 0.0078 0.045 Uiso 1 1 calc R
C32 C 0.69444(14) 0.7934(2) 0.0614(2) 0.0388(9) Uani 1 1 d .
H32 H 0.6933 0.8326 0.0199 0.047 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'
Ga Ga 0.2307 1.6083 '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'
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
C12 Ga1 C1 99.66(13) .
C12 Ga1 C10 124.15(14) .
C1 Ga1 C10 113.29(14) .
C12 Ga1 N2 112.53(11) .
C1 Ga1 N2 105.34(11) .
C10 Ga1 N2 100.92(12) .
C23 Ga2 C25 121.98(15) .
C23 Ga2 C14 102.25(14) .
C25 Ga2 C14 114.58(14) .
C23 Ga2 N1 110.73(13) 1_545
C25 Ga2 N1 101.05(12) 1_545
C14 Ga2 N1 105.36(11) 1_545
C5 N1 C6 117.1(3) .
C5 N1 Ga2 118.3(2) 1_565
C6 N1 Ga2 124.54(19) 1_565
C19 N2 C18 117.9(3) .
C19 N2 Ga1 120.8(2) .
C18 N2 Ga1 121.33(19) .
C2 C1 Ga1 172.6(3) .
C1 C2 C3 175.1(3) .
C4 C3 C7 116.8(3) .
C4 C3 C2 121.8(3) .
C7 C3 C2 121.4(3) .
C5 C4 C3 120.6(3) .
C5 C4 H4 119.7 .
C3 C4 H4 119.7 .
N1 C5 C4 122.2(3) .
N1 C5 C8 119.3(3) .
C4 C5 C8 118.4(3) .
N1 C6 C7 122.0(3) .
N1 C6 C9 119.1(3) .
C7 C6 C9 118.9(3) .
C6 C7 C3 121.3(3) .
C6 C7 H7 119.4 .
C3 C7 H7 119.4 .
C5 C8 H8A 109.5 .
C5 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C5 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C6 C9 H9A 109.5 .
C6 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C6 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C11 C10 Ga1 117.5(2) .
C11 C10 H10A 107.9 .
Ga1 C10 H10A 107.9 .
C11 C10 H10B 107.9 .
Ga1 C10 H10B 107.9 .
H10A C10 H10B 107.2 .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C13 C12 Ga1 114.4(2) .
C13 C12 H12A 108.7 .
Ga1 C12 H12A 108.7 .
C13 C12 H12B 108.7 .
Ga1 C12 H12B 108.7 .
H12A C12 H12B 107.6 .
C12 C13 H13A 109.5 .
C12 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C12 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C15 C14 Ga2 174.1(3) .
C14 C15 C16 176.2(3) .
C20 C16 C17 117.1(3) .
C20 C16 C15 120.4(3) .
C17 C16 C15 122.5(3) .
C18 C17 C16 120.7(3) .
C18 C17 H17 119.7 .
C16 C17 H17 119.7 .
N2 C18 C17 121.6(3) .
N2 C18 C21 119.1(3) .
C17 C18 C21 119.3(3) .
N2 C19 C20 122.1(3) .
N2 C19 C22 118.8(3) .
C20 C19 C22 119.0(3) .
C19 C20 C16 120.5(3) .
C19 C20 H20 119.8 .
C16 C20 H20 119.8 .
C18 C21 H21A 109.5 .
C18 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C18 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C19 C22 H22A 109.5 .
C19 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C19 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C24 C23 Ga2 115.4(3) .
C24 C23 H23A 108.4 .
Ga2 C23 H23A 108.4 .
C24 C23 H23B 108.4 .
Ga2 C23 H23B 108.4 .
H23A C23 H23B 107.5 .
C23 C24 H24A 109.5 .
C23 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C23 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
C26 C25 Ga2 116.6(2) .
C26 C25 H25A 108.1 .
Ga2 C25 H25A 108.1 .
C26 C25 H25B 108.1 .
Ga2 C25 H25B 108.1 .
H25A C25 H25B 107.3 .
C25 C26 H26A 109.5 .
C25 C26 H26B 109.5 .
H26A C26 H26B 109.5 .
C25 C26 H26C 109.5 .
H26A C26 H26C 109.5 .
H26B C26 H26C 109.5 .
C32 C27 C28 120.2(4) .
C32 C27 H27 119.9 .
C28 C27 H27 119.9 .
C27 C28 C29 120.5(4) .
C27 C28 H28 119.8 .
C29 C28 H28 119.8 .
C28 C29 C30 119.3(4) .
C28 C29 H29 120.3 .
C30 C29 H29 120.3 .
C31 C30 C29 119.4(4) .
C31 C30 H30 120.3 .
C29 C30 H30 120.3 .
C30 C31 C32 120.9(4) .
C30 C31 H31 119.5 .
C32 C31 H31 119.5 .
C27 C32 C31 119.7(4) .
C27 C32 H32 120.2 .
C31 C32 H32 120.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ga1 C12 1.988(3) .
Ga1 C1 1.992(3) .
Ga1 C10 1.995(3) .
Ga1 N2 2.137(2) .
Ga2 C23 1.977(3) .
Ga2 C25 1.978(3) .
Ga2 C14 1.986(3) .
Ga2 N1 2.153(2) 1_545
N1 C5 1.367(4) .
N1 C6 1.368(4) .
N1 Ga2 2.153(2) 1_565
N2 C19 1.367(4) .
N2 C18 1.367(4) .
C1 C2 1.220(4) .
C2 C3 1.433(4) .
C3 C4 1.388(4) .
C3 C7 1.390(4) .
C4 C5 1.384(4) .
C4 H4 0.9500 .
C5 C8 1.505(4) .
C6 C7 1.375(4) .
C6 C9 1.501(4) .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.520(5) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.534(5) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.208(4) .
C15 C16 1.442(4) .
C16 C20 1.397(4) .
C16 C17 1.398(4) .
C17 C18 1.382(4) .
C17 H17 0.9500 .
C18 C21 1.497(4) .
C19 C20 1.376(4) .
C19 C22 1.509(4) .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C24 1.502(6) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 C26 1.517(5) .
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 C32 1.368(5) .
C27 C28 1.376(5) .
C27 H27 0.9500 .
C28 C29 1.383(5) .
C28 H28 0.9500 .
C29 C30 1.389(5) .
C29 H29 0.9500 .
C30 C31 1.375(5) .
C30 H30 0.9500 .
C31 C32 1.377(5) .
C31 H31 0.9500 .
C32 H32 0.9500 .
