#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/23/4322320.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_4322320
loop_
_publ_author_name
'Karl Hensen'
'Alexander Lemke'
'Thorsten Stumpf'
'Michael Bolte'
'Holger Fleischer'
'Colin R. Pulham'
'Robert O. Gould'
'Steven Harris'
_publ_contact_author
;
      Dr. Michael Bolte
      Institut für Organische Chemie
      J. W. Goethe-Universität
      Marie-Curie-Str. 11
      60439 Frankfurt/Main
      Germany
;
_publ_contact_author_email       bolte@chemie.uni-frankfurt.de
_publ_contact_author_fax         '49 69 798 29128'
_publ_contact_author_phone       '49 69 798 29136'
_publ_section_title
;
 Synthesis and Structural Characterization of
 (1,4-Dihydropyrid-1-yl)aluminum Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4700
_journal_page_last               4704
_journal_paper_doi               10.1021/ic9905695
_journal_volume                  38
_journal_year                    1999
_chemical_formula_moiety         '[Al(Hpyr)3(pyr)].0.5PhMe'
_chemical_formula_sum            'C23.5 H27 Al N4'
_chemical_formula_weight         392.47
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL
_cell_angle_alpha                109.74(3)
_cell_angle_beta                 98.28(3)
_cell_angle_gamma                96.43(3)
_cell_formula_units_Z            2
_cell_length_a                   9.202(5)
_cell_length_b                   10.888(5)
_cell_length_c                   11.756(5)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      15
_cell_volume                     1080.6(9)
_computing_cell_refinement       'Stoe DIF4'
_computing_data_collection       'Stoe DIF4'
_computing_data_reduction        'Stoe REDU4'
_computing_molecular_graphics    SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      220(2)
_diffrn_measurement_device
; 
Stoe Stadi-4 diffractometer with 
Oxford Cryosystems variable temperature device. 
;
_diffrn_measurement_method       'Omega-theta with learnt profile (Clegg)'
_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  0.1072
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7090
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.65
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0014(23)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.021
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4919
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.046
_refine_ls_restrained_S_obs      1.029
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          -0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0512P)²+0.5330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1354
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                3656
_reflns_number_total             4950
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic9905695_1.cif
_cod_data_source_block           IV
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.5330P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.5330P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difference Fourier map' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_formula_sum        'C23.50 H27 Al N4'
_cod_database_code               4322320
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Al1 Al 0.05290(6) 0.89285(6) 0.71667(5) 0.0336(2) Uani 1 d . .
N11 N 0.1742(2) 1.0537(2) 0.7939(2) 0.0387(4) Uani 1 d . .
C21 C 0.2754(2) 1.0844(2) 0.9043(2) 0.0410(5) Uani 1 d . .
H21 H 0.2708(26) 1.0139(24) 0.9377(22) 0.051(7) Uiso 1 d . .
C31 C 0.3745(3) 1.1947(3) 0.9589(2) 0.0527(6) Uani 1 d . .
H31 H 0.4331(30) 1.2037(26) 1.0314(25) 0.060(8) Uiso 1 d . .
C41 C 0.3910(4) 1.3030(3) 0.9082(3) 0.0712(8) Uani 1 d . .
H41A H 0.4894(35) 1.3104(29) 0.8846(27) 0.076(9) Uiso 1 d . .
H41B H 0.3875(37) 1.3911(36) 0.9714(31) 0.094(11) Uiso 1 d . .
C51 C 0.2747(3) 1.2697(3) 0.7953(3) 0.0618(7) Uani 1 d . .
H51 H 0.2657(35) 1.3291(32) 0.7542(29) 0.088(10) Uiso 1 d . .
C61 C 0.1796(3) 1.1559(2) 0.7465(2) 0.0491(5) Uani 1 d . .
H61 H 0.1054(28) 1.1375(24) 0.6745(23) 0.055(7) Uiso 1 d . .
N12 N 0.0808(2) 0.8111(2) 0.5583(2) 0.0387(4) Uani 1 d . .
C22 C 0.1823(2) 0.8664(2) 0.5044(2) 0.0450(5) Uani 1 d . .
H22 H 0.2424(26) 0.9631(24) 0.5644(21) 0.049(6) Uiso 1 d . .
C32 C 0.2069(3) 0.8067(3) 0.3915(2) 0.0558(6) Uani 1 d . .
H32 H 0.2872(35) 0.8582(31) 0.3628(28) 0.089(10) Uiso 1 d . .
C42 C 0.1219(4) 0.6747(3) 0.3063(2) 0.0638(7) Uani 1 d . .
H42A H 0.2008(31) 0.6132(28) 0.2724(25) 0.068(8) Uiso 1 d . .
H42B H 0.0573(40) 0.6870(34) 0.2309(32) 0.103(11) Uiso 1 d . .
C52 C 0.0302(3) 0.6147(3) 0.3754(2) 0.0566(6) Uani 1 d . .
H52 H -0.0257(30) 0.5218(28) 0.3365(24) 0.064(8) Uiso 1 d . .
C62 C 0.0157(3) 0.6808(2) 0.4903(2) 0.0477(5) Uani 1 d . .
H62 H -0.0505(28) 0.6389(24) 0.5336(23) 0.057(7) Uiso 1 d . .
N13 N 0.0674(2) 0.7847(2) 0.80648(15) 0.0360(4) Uani 1 d . .
C23 C 0.1977(2) 0.7303(2) 0.8162(2) 0.0404(4) Uani 1 d . .
H23 H 0.2699(25) 0.7521(21) 0.7685(20) 0.043(6) Uiso 1 d . .
C33 C 0.2297(3) 0.6581(2) 0.8844(2) 0.0445(5) Uani 1 d . .
H33 H 0.3237(29) 0.6255(24) 0.8835(22) 0.054(7) Uiso 1 d . .
C43 C 0.1258(3) 0.6215(3) 0.9589(3) 0.0551(6) Uani 1 d . .
H43A H 0.0955(32) 0.5185(31) 0.9278(26) 0.077(9) Uiso 1 d . .
H43B H 0.1772(30) 0.6505(27) 1.0418(27) 0.065(8) Uiso 1 d . .
C53 C -0.0099(3) 0.6834(2) 0.9473(2) 0.0485(5) Uani 1 d . .
H53 H -0.0893(28) 0.6704(24) 0.9876(23) 0.057(7) Uiso 1 d . .
C63 C -0.0318(2) 0.7555(2) 0.8773(2) 0.0399(4) Uani 1 d . .
H63 H -0.1240(28) 0.7929(24) 0.8713(22) 0.055(7) Uiso 1 d . .
N14 N -0.1529(2) 0.9246(2) 0.71130(15) 0.0368(4) Uani 1 d . .
C24 C -0.2640(3) 0.8539(2) 0.6159(2) 0.0489(5) Uani 1 d . .
H24 H -0.2340(26) 0.7959(23) 0.5474(22) 0.048(6) Uiso 1 d . .
C34 C -0.4111(3) 0.8672(3) 0.6194(3) 0.0615(7) Uani 1 d . .
H34 H -0.4806(34) 0.8197(30) 0.5508(28) 0.078(9) Uiso 1 d . .
C44 C -0.4445(3) 0.9568(3) 0.7223(3) 0.0581(6) Uani 1 d . .
H44 H -0.5508(33) 0.9670(28) 0.7210(25) 0.072(8) Uiso 1 d . .
C54 C -0.3313(3) 1.0313(3) 0.8190(2) 0.0514(6) Uani 1 d . .
H54 H -0.3450(32) 1.0999(29) 0.8955(28) 0.076(9) Uiso 1 d . .
C64 C -0.1879(3) 1.0133(2) 0.8113(2) 0.0435(5) Uani 1 d . .
H64 H -0.1074(28) 1.0674(25) 0.8736(24) 0.056(7) Uiso 1 d . .
C1T C 0.4442(9) 0.4676(7) 0.2704(8) 0.128(4) Uani 0.50 d PD -1
H1T1 H 0.4651(80) 0.5517(12) 0.2592(9) 0.192 Uiso 0.50 calc PR -1
H1T2 H 0.3403(22) 0.4285(69) 0.2360(16) 0.192 Uiso 0.50 calc PR -1
H1T3 H 0.5070(61) 0.4084(59) 0.2288(14) 0.192 Uiso 0.50 calc PR -1
C2T C 0.4760(7) 0.4900(5) 0.4064(7) 0.063(2) Uani 0.50 d PD -1
C3T C 0.6189(9) 0.5009(6) 0.4678(6) 0.069(4) Uani 0.50 d PD -1
H3T H 0.6983(9) 0.4944(6) 0.4250(6) 0.083 Uiso 0.50 calc PR -1
C4T C 0.6455(14) 0.5211(7) 0.5911(8) 0.089(3) Uani 0.50 d PD -1
H4T H 0.7433(14) 0.5285(7) 0.6324(8) 0.106 Uiso 0.50 calc PR -1
C5T C 0.5317(10) 0.5308(8) 0.6547(10) 0.092(3) Uani 0.50 d PD -1
H5T H 0.5506(10) 0.5447(8) 0.7392(10) 0.111 Uiso 0.50 calc PR -1
C6T C 0.3905(12) 0.5199(7) 0.5938(7) 0.075(3) Uani 0.50 d PD -1
H6T H 0.3117(12) 0.5263(7) 0.6372(7) 0.091 Uiso 0.50 calc PR -1
C7T C 0.3610(12) 0.5000(6) 0.4713(6) 0.069(4) Uani 0.50 d PD -1
H7T H 0.2628(12) 0.4931(6) 0.4310(6) 0.083 Uiso 0.50 calc PR -1
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'
Al Al 0.0645 0.0514 '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
N11 Al1 N13 112.58(9) . . ?
N11 Al1 N12 112.05(9) . . ?
N13 Al1 N12 111.96(9) . . ?
N11 Al1 N14 107.05(9) . . ?
N13 Al1 N14 103.54(8) . . ?
N12 Al1 N14 109.13(8) . . ?
C21 N11 C61 113.6(2) . . ?
C21 N11 Al1 122.70(15) . . ?
C61 N11 Al1 123.70(15) . . ?
C31 C21 N11 125.3(2) . . ?
C31 C21 H21 121.1(15) . . ?
N11 C21 H21 113.5(15) . . ?
C21 C31 C41 123.2(2) . . ?
C21 C31 H31 116.9(17) . . ?
C41 C31 H31 119.8(17) . . ?
C51 C41 C31 109.5(2) . . ?
C51 C41 H41A 107.9(18) . . ?
C31 C41 H41A 109.2(18) . . ?
C51 C41 H41B 111.9(20) . . ?
C31 C41 H41B 111.6(20) . . ?
H41A C41 H41B 106.7(25) . . ?
C61 C51 C41 123.2(3) . . ?
C61 C51 H51 116.1(20) . . ?
C41 C51 H51 120.8(20) . . ?
C51 C61 N11 125.1(2) . . ?
C51 C61 H61 121.4(15) . . ?
N11 C61 H61 113.5(15) . . ?
C62 N12 C22 114.7(2) . . ?
C62 N12 Al1 121.07(14) . . ?
C22 N12 Al1 123.65(15) . . ?
C32 C22 N12 124.3(2) . . ?
C32 C22 H22 122.5(12) . . ?
N12 C22 H22 113.2(12) . . ?
C22 C32 C42 123.1(2) . . ?
C22 C32 H32 116.6(18) . . ?
C42 C32 H32 120.3(17) . . ?
C32 C42 C52 109.2(2) . . ?
C32 C42 H42A 107.9(15) . . ?
C52 C42 H42A 110.0(15) . . ?
C32 C42 H42B 108.8(19) . . ?
C52 C42 H42B 112.8(20) . . ?
H42A C42 H42B 108.0(24) . . ?
C62 C52 C42 122.8(2) . . ?
C62 C52 H52 116.1(15) . . ?
C42 C52 H52 121.1(15) . . ?
C52 C62 N12 124.7(2) . . ?
C52 C62 H62 121.1(14) . . ?
N12 C62 H62 114.1(14) . . ?
C63 N13 C23 113.4(2) . . ?
C63 N13 Al1 128.13(15) . . ?
C23 N13 Al1 118.27(13) . . ?
C33 C23 N13 125.6(2) . . ?
C33 C23 H23 120.1(13) . . ?
N13 C23 H23 114.3(13) . . ?
C23 C33 C43 123.0(2) . . ?
C23 C33 H33 118.1(15) . . ?
C43 C33 H33 118.9(14) . . ?
C33 C43 C53 109.4(2) . . ?
C33 C43 H43A 109.8(16) . . ?
C53 C43 H43A 110.0(16) . . ?
C33 C43 H43B 108.3(17) . . ?
C53 C43 H43B 111.7(17) . . ?
H43A C43 H43B 107.6(22) . . ?
C63 C53 C43 123.3(2) . . ?
C63 C53 H53 115.0(15) . . ?
C43 C53 H53 121.7(15) . . ?
C53 C63 N13 125.2(2) . . ?
C53 C63 H63 120.4(14) . . ?
N13 C63 H63 114.4(14) . . ?
C24 N14 C64 118.2(2) . . ?
C24 N14 Al1 122.5(2) . . ?
C64 N14 Al1 119.07(15) . . ?
N14 C24 C34 121.7(2) . . ?
N14 C24 H24 115.1(15) . . ?
C34 C24 H24 123.1(15) . . ?
C44 C34 C24 119.2(2) . . ?
C44 C34 H34 123.1(20) . . ?
C24 C34 H34 117.6(20) . . ?
C54 C44 C34 119.3(2) . . ?
C54 C44 H44 123.2(17) . . ?
C34 C44 H44 117.5(17) . . ?
C64 C54 C44 119.1(2) . . ?
C64 C54 H54 116.2(17) . . ?
C44 C54 H54 124.7(17) . . ?
N14 C64 C54 122.4(2) . . ?
N14 C64 H64 116.5(15) . . ?
C54 C64 H64 120.9(16) . . ?
C2T C1T H1T1 109.5(2) . . ?
C2T C1T H1T2 109.5(3) . . ?
H1T1 C1T H1T2 109.5 . . ?
C2T C1T H1T3 109.5(3) . . ?
H1T1 C1T H1T3 109.5 . . ?
H1T2 C1T H1T3 109.5 . . ?
C3T C2T C7T 118.9(7) . . ?
C3T C2T C1T 120.9(5) . . ?
C7T C2T C1T 120.2(5) . . ?
C4T C3T C2T 120.0(9) . . ?
C4T C3T H3T 120.0(7) . . ?
C2T C3T H3T 120.0(4) . . ?
C5T C4T C3T 120.8(11) . . ?
C5T C4T H4T 119.6(6) . . ?
C3T C4T H4T 119.6(7) . . ?
C6T C5T C4T 119.0(10) . . ?
C6T C5T H5T 120.5(6) . . ?
C4T C5T H5T 120.5(6) . . ?
C5T C6T C7T 121.3(11) . . ?
C5T C6T H6T 119.3(6) . . ?
C7T C6T H6T 119.3(7) . . ?
C6T C7T C2T 119.9(9) . . ?
C6T C7T H7T 120.1(7) . . ?
C2T C7T H7T 120.1(4) . . ?
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
Al1 N11 1.826(2) . ?
Al1 N13 1.831(2) . ?
Al1 N12 1.842(2) . ?
Al1 N14 1.959(2) . ?
N11 C21 1.397(3) . ?
N11 C61 1.402(3) . ?
C21 C31 1.323(3) . ?
C21 H21 0.97(2) . ?
C31 C41 1.493(4) . ?
C31 H31 0.91(3) . ?
C41 C51 1.489(4) . ?
C41 H41A 0.99(3) . ?
C41 H41B 1.00(4) . ?
C51 C61 1.328(3) . ?
C51 H51 0.93(3) . ?
C61 H61 0.95(3) . ?
N12 C62 1.385(3) . ?
N12 C22 1.392(3) . ?
C22 C32 1.331(3) . ?
C22 H22 1.08(2) . ?
C32 C42 1.494(4) . ?
C32 H32 1.04(3) . ?
C42 C52 1.494(4) . ?
C42 H42A 1.07(3) . ?
C42 H42B 1.05(4) . ?
C52 C62 1.333(3) . ?
C52 H52 1.00(3) . ?
C62 H62 1.01(3) . ?
N13 C63 1.400(2) . ?
N13 C23 1.402(3) . ?
C23 C33 1.326(3) . ?
C23 H23 0.99(2) . ?
C33 C43 1.493(3) . ?
C33 H33 0.97(3) . ?
C43 C53 1.495(4) . ?
C43 H43A 1.05(3) . ?
C43 H43B 0.95(3) . ?
C53 C63 1.326(3) . ?
C53 H53 0.95(3) . ?
C63 H63 0.98(3) . ?
N14 C24 1.344(3) . ?
N14 C64 1.353(3) . ?
C24 C34 1.383(3) . ?
C24 H24 0.94(2) . ?
C34 C44 1.373(4) . ?
C34 H34 0.91(3) . ?
C44 C54 1.372(4) . ?
C44 H44 1.00(3) . ?
C54 C64 1.367(3) . ?
C54 H54 0.99(3) . ?
C64 H64 0.94(3) . ?
C1T C2T 1.512(10) . ?
C1T H1T1 0.97 . ?
C1T H1T2 0.97 . ?
C1T H1T3 0.97 . ?
C2T C3T 1.378(10) . ?
C2T C7T 1.384(10) . ?
C3T C4T 1.371(10) . ?
C3T H3T 0.94 . ?
C4T C5T 1.365(10) . ?
C4T H4T 0.94 . ?
C5T C6T 1.362(10) . ?
C5T H5T 0.94 . ?
C6T C7T 1.363(10) . ?
C6T H6T 0.94 . ?
C7T H7T 0.94 . ?
