#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/47/4064780.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_4064780
loop_
_publ_author_name
'Koller, Jürgen'
'Bergman, Robert G.'
_publ_section_title
;
 Highly Efficient Aluminum-Catalyzed Ring-Opening Polymerization of Cyclic
 Carbonates, Lactones, and Lactides, Including a Unique Crystallographic
 Snapshot of an Intermediate
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3217
_journal_paper_doi               10.1021/om2003283
_journal_volume                  30
_journal_year                    2011
_chemical_formula_sum            'C21.59 H44.98 Al N4 O3.8 Si2'
_chemical_formula_weight         504.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-12-07 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.839(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.943(5)
_cell_length_b                   10.526(4)
_cell_length_c                   20.327(7)
_cell_measurement_reflns_used    5661
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     3117.3(19)
_computing_cell_refinement       'Bruker APEX2 v.2009.1'
_computing_data_collection       'Bruker APEX2 v.2009.1'
_computing_data_reduction        'Bruker APEX2 v.2009.1'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'φ and ω 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  0.1032
_diffrn_reflns_av_sigmaI/netI    0.1031
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25132
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.40
_diffrn_standards_decay_%        1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1565
_refine_ls_R_factor_gt           0.0652
_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)+(0.0616P)²+0.4329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                2681
_reflns_number_total             5661
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2003283_si_002.cif
_cod_data_source_block           jk-iii-194
_cod_original_cell_volume        3117.5(18)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C21.59 H44.98 Al N4 O3.80 Si2'
_cod_database_code               4064780
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Al1 Al 0.25481(8) 0.08308(11) 0.08221(5) 0.0416(3) Uani 1 1 d .
Si1 Si 0.24017(10) -0.08659(14) 0.21196(6) 0.0680(4) Uani 1 1 d .
Si2 Si 0.17882(9) 0.33853(13) 0.00272(6) 0.0616(4) Uani 1 1 d .
O1 O 0.36974(17) 0.0837(3) 0.08619(12) 0.0481(7) Uani 1 1 d .
O2 O 0.6026(2) -0.0530(3) 0.14781(13) 0.0712(10) Uani 1 1 d .
O3 O 0.73517(19) 0.0077(3) 0.12050(13) 0.0627(9) Uani 1 1 d .
N1 N 0.2040(2) 0.0297(3) 0.15215(14) 0.0490(9) Uani 1 1 d .
N2 N 0.1812(2) 0.2240(3) 0.06422(14) 0.0452(8) Uani 1 1 d .
N3 N 0.7367(3) -0.0941(4) 0.21817(16) 0.0664(11) Uani 1 1 d .
N4 N 0.2152(2) -0.0346(3) 0.00649(17) 0.0454(9) Uani 1 1 d .
H4 H 0.228(3) -0.004(4) -0.0268(19) 0.067(15) Uiso 1 1 d .
C1 C 0.1256(3) 0.1076(4) 0.1494(2) 0.0523(12) Uani 1 1 d .
C2 C 0.0588(3) 0.0892(5) 0.1871(2) 0.0722(15) Uani 1 1 d .
H2A H 0.0634 0.0175 0.2161 0.087 Uiso 1 1 calc R
C3 C -0.0139(4) 0.1730(7) 0.1833(3) 0.091(2) Uani 1 1 d .
H3A H -0.0579 0.1584 0.2098 0.109 Uiso 1 1 calc R
C4 C -0.0224(3) 0.2759(6) 0.1419(3) 0.089(2) Uani 1 1 d .
H4A H -0.0714 0.3342 0.1405 0.107 Uiso 1 1 calc R
C5 C 0.0410(3) 0.2961(5) 0.1013(2) 0.0669(14) Uani 1 1 d .
H5A H 0.0338 0.3671 0.0717 0.080 Uiso 1 1 calc R
C6 C 0.1142(3) 0.2133(4) 0.1038(2) 0.0528(12) Uani 1 1 d .
C7 C 0.1651(4) -0.2306(5) 0.1970(2) 0.0962(19) Uani 1 1 d .
H7A H 0.1024 -0.2072 0.1995 0.144 Uiso 1 1 calc R
H7B H 0.1887 -0.2946 0.2315 0.144 Uiso 1 1 calc R
H7C H 0.1648 -0.2655 0.1523 0.144 Uiso 1 1 calc R
C8 C 0.3582(3) -0.1365(5) 0.2068(2) 0.0904(17) Uani 1 1 d .
H8A H 0.3573 -0.1680 0.1613 0.136 Uiso 1 1 calc R
H8B H 0.3795 -0.2041 0.2397 0.136 Uiso 1 1 calc R
H8C H 0.3998 -0.0636 0.2167 0.136 Uiso 1 1 calc R
C9 C 0.2459(4) -0.0277(6) 0.3001(2) 0.105(2) Uani 1 1 d .
H9A H 0.1843 -0.0032 0.3047 0.158 Uiso 1 1 calc R
H9B H 0.2868 0.0460 0.3091 0.158 Uiso 1 1 calc R
H9C H 0.2695 -0.0954 0.3324 0.158 Uiso 1 1 calc R
C10 C 0.1909(4) 0.5022(5) 0.0378(3) 0.0986(18) Uani 1 1 d .
H10A H 0.2465 0.5075 0.0738 0.148 Uiso 1 1 calc R
H10B H 0.1372 0.5229 0.0561 0.148 Uiso 1 1 calc R
H10C H 0.1952 0.5626 0.0019 0.148 Uiso 1 1 calc R
C11 C 0.2787(3) 0.3052(4) -0.0354(2) 0.0765(15) Uani 1 1 d .
H11A H 0.3354 0.3085 -0.0003 0.115 Uiso 1 1 calc R
H11B H 0.2813 0.3690 -0.0701 0.115 Uiso 1 1 calc R
H11C H 0.2720 0.2205 -0.0560 0.115 Uiso 1 1 calc R
C12 C 0.0718(4) 0.3301(5) -0.0663(2) 0.0973(18) Uani 1 1 d .
H12A H 0.0181 0.3478 -0.0474 0.146 Uiso 1 1 calc R
H12B H 0.0661 0.2449 -0.0863 0.146 Uiso 1 1 calc R
H12C H 0.0753 0.3931 -0.1011 0.146 Uiso 1 1 calc R
C13 C 0.1128(3) -0.0491(5) -0.0098(2) 0.0744(15) Uani 1 1 d .
H13A H 0.0943 -0.1073 -0.0481 0.112 Uiso 1 1 calc R
H13B H 0.0841 0.0339 -0.0215 0.112 Uiso 1 1 calc R
H13C H 0.0932 -0.0835 0.0295 0.112 Uiso 1 1 calc R
C14 C 0.2606(3) -0.1610(4) 0.0146(2) 0.0652(13) Uani 1 1 d .
H14A H 0.2368 -0.2128 -0.0255 0.098 Uiso 1 1 calc R
H14B H 0.2479 -0.2036 0.0545 0.098 Uiso 1 1 calc R
H14C H 0.3270 -0.1501 0.0203 0.098 Uiso 1 1 calc R
C15 C 0.4464(3) 0.1488(4) 0.1244(2) 0.0575(12) Uani 1 1 d .
H15A H 0.4630 0.1127 0.1705 0.069 Uiso 1 1 calc R
H15B H 0.4309 0.2395 0.1281 0.069 Uiso 1 1 calc R
C16 C 0.5269(3) 0.1372(5) 0.0912(2) 0.0588(12) Uani 1 1 d .
H16A H 0.5111 0.1770 0.0460 0.071 Uiso 1 1 calc R
H16B H 0.5802 0.1832 0.1185 0.071 Uiso 1 1 calc R
C17 C 0.5524(3) 0.0008(5) 0.0843(2) 0.0705(15) Uani 1 1 d .
H17A H 0.4958 -0.0494 0.0677 0.085 Uiso 1 1 calc R
H17B H 0.5905 -0.0056 0.0504 0.085 Uiso 1 1 calc R
C18 C 0.6952(3) -0.0417(4) 0.15984(19) 0.0542(12) Uani 1 1 d .
C19 C 0.6858(4) -0.1558(6) 0.2640(3) 0.119(2) Uani 1 1 d .
H19A H 0.6198 -0.1426 0.2470 0.179 Uiso 1 1 calc R
H19B H 0.7047 -0.1186 0.3092 0.179 Uiso 1 1 calc R
H19C H 0.6991 -0.2471 0.2663 0.179 Uiso 1 1 calc R
C20 C 0.8356(4) -0.1002(5) 0.2365(2) 0.0911(17) Uani 1 1 d .
H20A H 0.8611 -0.0564 0.2022 0.137 Uiso 1 1 calc R
H20B H 0.8552 -0.1892 0.2393 0.137 Uiso 1 1 calc R
H20C H 0.8577 -0.0591 0.2803 0.137 Uiso 1 1 calc R
O4 O 0.5038(6) 0.0158(9) 0.5307(4) 0.151(4) Uani 0.795(6) 1 d P
C21 C 0.4768(9) -0.0933(15) 0.5599(7) 0.165(6) Uani 0.795(6) 1 d P
H21A H 0.4129 -0.1159 0.5379 0.198 Uiso 0.795(6) 1 calc PR
H21B H 0.5172 -0.1655 0.5548 0.198 Uiso 0.795(6) 1 calc PR
C22 C 0.4824(10) -0.0713(16) 0.6168(8) 0.233(8) Uani 0.795(6) 1 d P
H22A H 0.4644 -0.1466 0.6392 0.350 Uiso 0.795(6) 1 calc PR
H22B H 0.4417 -0.0004 0.6212 0.350 Uiso 0.795(6) 1 calc PR
H22C H 0.5459 -0.0485 0.6380 0.350 Uiso 0.795(6) 1 calc PR
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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
O1 Al1 N2 124.09(15) .
O1 Al1 N1 123.32(14) .
N2 Al1 N1 93.95(14) .
O1 Al1 N4 99.52(14) .
N2 Al1 N4 106.92(15) .
N1 Al1 N4 107.97(15) .
N1 Si1 C8 108.21(18) .
N1 Si1 C7 112.2(2) .
C8 Si1 C7 107.7(3) .
N1 Si1 C9 112.2(2) .
C8 Si1 C9 107.6(2) .
C7 Si1 C9 108.7(2) .
N2 Si2 C10 112.6(2) .
N2 Si2 C11 106.23(18) .
C10 Si2 C11 108.4(2) .
N2 Si2 C12 112.5(2) .
C10 Si2 C12 108.9(3) .
C11 Si2 C12 107.9(2) .
C15 O1 Al1 135.7(2) .
C18 O2 C17 115.5(3) .
C1 N1 Si1 124.3(3) .
C1 N1 Al1 105.8(3) .
Si1 N1 Al1 129.93(19) .
C6 N2 Si2 124.0(3) .
C6 N2 Al1 106.8(3) .
Si2 N2 Al1 128.50(17) .
C18 N3 C20 119.7(4) .
C18 N3 C19 122.8(4) .
C20 N3 C19 117.3(4) .
C14 N4 C13 110.6(3) .
C14 N4 Al1 115.3(3) .
C13 N4 Al1 110.7(2) .
C14 N4 H4 105(3) .
C13 N4 H4 106(3) .
Al1 N4 H4 109(3) .
C2 C1 N1 125.5(4) .
C2 C1 C6 117.7(4) .
N1 C1 C6 116.8(3) .
C3 C2 C1 121.8(5) .
C3 C2 H2A 119.1 .
C1 C2 H2A 119.1 .
C4 C3 C2 120.3(5) .
C4 C3 H3A 119.8 .
C2 C3 H3A 119.8 .
C3 C4 C5 120.1(5) .
C3 C4 H4A 119.9 .
C5 C4 H4A 119.9 .
C6 C5 C4 120.7(5) .
C6 C5 H5A 119.6 .
C4 C5 H5A 119.6 .
C5 C6 N2 125.2(4) .
C5 C6 C1 119.3(4) .
N2 C6 C1 115.5(4) .
Si1 C7 H7A 109.5 .
Si1 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
Si1 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
Si1 C8 H8A 109.5 .
Si1 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
Si1 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
Si1 C9 H9A 109.5 .
Si1 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
Si1 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
Si2 C10 H10A 109.5 .
Si2 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
Si2 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
Si2 C11 H11A 109.5 .
Si2 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
Si2 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
Si2 C12 H12A 109.5 .
Si2 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
Si2 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
N4 C13 H13A 109.5 .
N4 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
N4 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
N4 C14 H14A 109.5 .
N4 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
N4 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
O1 C15 C16 110.2(3) .
O1 C15 H15A 109.6 .
C16 C15 H15A 109.6 .
O1 C15 H15B 109.6 .
C16 C15 H15B 109.6 .
H15A C15 H15B 108.1 .
C17 C16 C15 111.3(4) .
C17 C16 H16A 109.4 .
C15 C16 H16A 109.4 .
C17 C16 H16B 109.4 .
C15 C16 H16B 109.4 .
H16A C16 H16B 108.0 .
O2 C17 C16 112.4(4) .
O2 C17 H17A 109.1 .
C16 C17 H17A 109.1 .
O2 C17 H17B 109.1 .
C16 C17 H17B 109.1 .
H17A C17 H17B 107.9 .
O3 C18 N3 124.4(4) .
O3 C18 O2 123.3(4) .
N3 C18 O2 112.3(4) .
N3 C19 H19A 109.5 .
N3 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
N3 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
N3 C20 H20A 109.5 .
N3 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
N3 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
O4 O4 C21 103.4(11) 3_656
C22 C21 O4 107.2(16) .
C22 C21 H21A 110.3 .
O4 C21 H21A 110.3 .
C22 C21 H21B 110.3 .
O4 C21 H21B 110.3 .
H21A C21 H21B 108.5 .
C21 C22 H22A 109.5 .
C21 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C21 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Al1 O1 1.701(3) .
Al1 N2 1.834(3) .
Al1 N1 1.842(3) .
Al1 N4 1.962(3) .
Si1 N1 1.725(3) .
Si1 C8 1.865(5) .
Si1 C7 1.870(5) .
Si1 C9 1.879(4) .
Si2 N2 1.731(3) .
Si2 C10 1.858(5) .
Si2 C11 1.862(4) .
Si2 C12 1.881(5) .
O1 C15 1.411(4) .
O2 C18 1.356(5) .
O2 C17 1.456(5) .
O3 C18 1.216(4) .
N1 C1 1.421(5) .
N2 C6 1.421(5) .
N3 C18 1.330(5) .
N3 C20 1.443(5) .
N3 C19 1.478(5) .
N4 C14 1.487(5) .
N4 C13 1.499(5) .
N4 H4 0.81(4) .
C1 C2 1.400(5) .
C1 C6 1.435(6) .
C2 C3 1.387(7) .
C2 H2A 0.9500 .
C3 C4 1.360(7) .
C3 H3A 0.9500 .
C4 C5 1.405(6) .
C4 H4A 0.9500 .
C5 C6 1.391(6) .
C5 H5A 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
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 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.508(5) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.499(6) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
O4 O4 1.273(13) 3_656
O4 C21 1.393(16) .
C21 C22 1.164(16) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
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
N4 H4 O3 0.81(4) 2.09(4) 2.854(4) 156(4) 3_655
