#------------------------------------------------------------------------------
#$Date: 2021-09-06 14:06:11 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268744 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/76/7707699.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_7707699
loop_
_publ_author_name
'Laiwattanapaisarn, Nattiya'
'Virachotikul, Arnut'
'Phomphrai, Khamphee'
_publ_section_title
;
 Cycloaddition of carbon dioxide to epoxides by highly active constrained
 aluminum chloride complexes.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11039
_journal_page_last               11048
_journal_paper_doi               10.1039/d1dt01903a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C23 H25 Al N2 O3'
_chemical_formula_sum            'C23 H25 Al N2 O3'
_chemical_formula_weight         404.43
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-26 deposited with the CCDC.	2021-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.4020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.8129(8)
_cell_length_b                   15.1936(5)
_cell_length_c                   13.9917(4)
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.430
_cell_measurement_theta_min      2.420
_cell_volume                     4627.7(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36235
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         2.681
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0989 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.8919. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0352P)²+4.6474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4285
_reflns_number_total             4739
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt01903a2.cif
_cod_data_source_block           kpav1_0m_a_sq
_cod_depositor_comments
'Adding full bibliography for 7707698--7707700.cif.'
_cod_database_code               7707699
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C10(H10A,H10B), C7(H7A,H7B), C13(H13A,H13B),
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C2(H2), C18(H18), C3(H3), C4(H4), C17(H17)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Al01 Al 0.64828(2) 0.47581(2) 0.48597(3) 0.01818(10) Uani 1 1 d . . . . .
O2 O 0.64651(4) 0.42015(6) 0.37021(6) 0.02133(19) Uani 1 1 d . . . . .
O3 O 0.72018(4) 0.51583(6) 0.55196(6) 0.02268(19) Uani 1 1 d . . . . .
O1 O 0.60942(4) 0.56722(6) 0.40691(6) 0.0234(2) Uani 1 1 d . . . . .
N2 N 0.65929(5) 0.35998(7) 0.55961(7) 0.0199(2) Uani 1 1 d . . . . .
N1 N 0.59580(5) 0.49229(7) 0.57907(7) 0.0190(2) Uani 1 1 d . . . . .
C12 C 0.66633(5) 0.28345(8) 0.52500(9) 0.0194(2) Uani 1 1 d . . . . .
C6 C 0.55352(5) 0.63080(8) 0.50782(9) 0.0203(2) Uani 1 1 d . . . . .
C9 C 0.56179(5) 0.56038(8) 0.57909(8) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.57728(6) 0.63345(8) 0.42613(9) 0.0211(2) Uani 1 1 d . . . . .
C20 C 0.65877(5) 0.33780(8) 0.35121(9) 0.0200(2) Uani 1 1 d . . . . .
C5 C 0.51839(6) 0.69854(9) 0.53057(9) 0.0237(3) Uani 1 1 d . . . . .
C16 C 0.66665(5) 0.27120(8) 0.42332(9) 0.0201(2) Uani 1 1 d . . . . .
C8 C 0.52603(6) 0.58112(9) 0.65123(9) 0.0224(3) Uani 1 1 d . . . . .
H8A H 0.552909 0.578087 0.721310 0.027 Uiso 1 1 calc R . . . .
H8B H 0.491604 0.539226 0.642772 0.027 Uiso 1 1 calc R . . . .
C11 C 0.65841(6) 0.37130(8) 0.66323(9) 0.0229(3) Uani 1 1 d . . . . .
H11A H 0.695881 0.402338 0.703220 0.027 Uiso 1 1 calc R . . . .
H11B H 0.656374 0.313407 0.694551 0.027 Uiso 1 1 calc R . . . .
C10 C 0.60145(6) 0.42553(8) 0.65805(9) 0.0218(3) Uani 1 1 d . . . . .
H10A H 0.564572 0.387414 0.641398 0.026 Uiso 1 1 calc R . . . .
H10B H 0.605743 0.454369 0.723239 0.026 Uiso 1 1 calc R . . . .
C15 C 0.67663(6) 0.18296(8) 0.40492(10) 0.0244(3) Uani 1 1 d . . . . .
C19 C 0.66320(6) 0.31188(9) 0.25709(9) 0.0242(3) Uani 1 1 d . . . . .
H19 H 0.659007 0.354369 0.205667 0.029 Uiso 1 1 calc R . . . .
C7 C 0.50166(6) 0.67583(9) 0.62446(10) 0.0274(3) Uani 1 1 d . . . . .
H7A H 0.456603 0.678140 0.611814 0.033 Uiso 1 1 calc R . . . .
H7B H 0.521392 0.717150 0.679366 0.033 Uiso 1 1 calc R . . . .
C2 C 0.56365(7) 0.70907(9) 0.36605(10) 0.0285(3) Uani 1 1 d . . . . .
H2 H 0.578182 0.714280 0.309371 0.034 Uiso 1 1 calc R . . . .
C18 C 0.67373(6) 0.22405(9) 0.23926(10) 0.0287(3) Uani 1 1 d . . . . .
H18 H 0.676465 0.208068 0.175094 0.034 Uiso 1 1 calc R . . . .
C13 C 0.67569(6) 0.19494(8) 0.57714(10) 0.0240(3) Uani 1 1 d . . . . .
H13A H 0.640339 0.180292 0.601481 0.029 Uiso 1 1 calc R . . . .
H13B H 0.713554 0.195096 0.634790 0.029 Uiso 1 1 calc R . . . .
C21 C 0.74207(6) 0.60301(8) 0.55580(10) 0.0269(3) Uani 1 1 d . . . . .
H21 H 0.708156 0.644135 0.557402 0.032 Uiso 1 1 calc R . . . .
C3 C 0.52896(7) 0.77640(9) 0.38917(10) 0.0330(3) Uani 1 1 d . . . . .
H3 H 0.520743 0.827236 0.347762 0.040 Uiso 1 1 calc R . . . .
C4 C 0.50557(7) 0.77248(9) 0.47102(10) 0.0313(3) Uani 1 1 d . . . . .
H4 H 0.481700 0.819238 0.484920 0.038 Uiso 1 1 calc R . . . .
C14 C 0.68115(7) 0.12813(9) 0.49674(10) 0.0288(3) Uani 1 1 d . . . . .
H14A H 0.720965 0.096747 0.518848 0.035 Uiso 1 1 calc R . . . .
H14B H 0.647493 0.084376 0.483065 0.035 Uiso 1 1 calc R . . . .
C17 C 0.68044(7) 0.15839(9) 0.31159(10) 0.0300(3) Uani 1 1 d . . . . .
H17 H 0.687382 0.098853 0.297275 0.036 Uiso 1 1 calc R . . . .
C23 C 0.76227(9) 0.62392(10) 0.46413(13) 0.0421(4) Uani 1 1 d . . . . .
H23A H 0.795332 0.583730 0.461422 0.063 Uiso 1 1 calc GR . . . .
H23B H 0.777123 0.684739 0.468307 0.063 Uiso 1 1 calc GR . . . .
H23C H 0.727355 0.616761 0.403570 0.063 Uiso 1 1 calc GR . . . .
C22 C 0.79454(8) 0.61454(11) 0.65147(13) 0.0445(4) Uani 1 1 d . . . . .
H22A H 0.780795 0.597893 0.708976 0.067 Uiso 1 1 calc GR . . . .
H22B H 0.807727 0.676207 0.658121 0.067 Uiso 1 1 calc GR . . . .
H22C H 0.829009 0.576969 0.649186 0.067 Uiso 1 1 calc GR . . . .
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'
Al Al 0.0645 0.0514 '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'
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
O2 Al01 O1 86.38(4) . . ?
O2 Al01 N2 90.88(4) . . ?
O2 Al01 N1 140.25(5) . . ?
O3 Al01 O2 113.78(4) . . ?
O3 Al01 O1 105.41(4) . . ?
O3 Al01 N2 94.62(4) . . ?
O3 Al01 N1 105.10(4) . . ?
O1 Al01 N2 159.15(5) . . ?
O1 Al01 N1 91.28(4) . . ?
N2 Al01 N1 77.71(4) . . ?
C20 O2 Al01 131.92(8) . . ?
C21 O3 Al01 128.11(8) . . ?
C1 O1 Al01 130.82(8) . . ?
C12 N2 Al01 127.32(8) . . ?
C12 N2 C11 121.19(10) . . ?
C11 N2 Al01 111.49(8) . . ?
C9 N1 Al01 124.58(8) . . ?
C9 N1 C10 117.86(10) . . ?
C10 N1 Al01 117.32(8) . . ?
N2 C12 C16 121.82(11) . . ?
N2 C12 C13 129.50(11) . . ?
C16 C12 C13 108.68(10) . . ?
C1 C6 C9 125.74(11) . . ?
C5 C6 C9 110.83(11) . . ?
C5 C6 C1 123.44(11) . . ?
N1 C9 C6 123.37(11) . . ?
N1 C9 C8 127.72(11) . . ?
C6 C9 C8 108.90(10) . . ?
O1 C1 C6 121.15(11) . . ?
O1 C1 C2 122.67(11) . . ?
C2 C1 C6 116.16(11) . . ?
O2 C20 C16 121.73(10) . . ?
O2 C20 C19 122.03(11) . . ?
C16 C20 C19 116.22(11) . . ?
C6 C5 C7 109.89(11) . . ?
C4 C5 C6 119.68(12) . . ?
C4 C5 C7 130.41(12) . . ?
C20 C16 C12 125.56(11) . . ?
C15 C16 C12 110.87(11) . . ?
C15 C16 C20 123.58(11) . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
C9 C8 C7 105.03(10) . . ?
H8A C8 H8B 108.8 . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
N2 C11 H11A 110.5 . . ?
N2 C11 H11B 110.5 . . ?
N2 C11 C10 106.29(9) . . ?
H11A C11 H11B 108.7 . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
N1 C10 C11 106.84(9) . . ?
N1 C10 H10A 110.4 . . ?
N1 C10 H10B 110.4 . . ?
C11 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C16 C15 C14 110.27(11) . . ?
C17 C15 C16 119.47(12) . . ?
C17 C15 C14 130.26(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 C20 120.06(12) . . ?
C18 C19 H19 120.0 . . ?
C5 C7 C8 104.86(10) . . ?
C5 C7 H7A 110.8 . . ?
C5 C7 H7B 110.8 . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.22(12) . . ?
C3 C2 H2 119.9 . . ?
C19 C18 H18 118.6 . . ?
C19 C18 C17 122.86(12) . . ?
C17 C18 H18 118.6 . . ?
C12 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
C12 C13 C14 105.23(10) . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 H13A 110.7 . . ?
C14 C13 H13B 110.7 . . ?
O3 C21 H21 108.7 . . ?
O3 C21 C23 110.92(11) . . ?
O3 C21 C22 108.62(11) . . ?
C23 C21 H21 108.7 . . ?
C22 C21 H21 108.7 . . ?
C22 C21 C23 111.26(13) . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.78(13) . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 117.72(12) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C15 C14 C13 104.89(10) . . ?
C15 C14 H14A 110.8 . . ?
C15 C14 H14B 110.8 . . ?
C13 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 108.8 . . ?
C15 C17 C18 117.79(12) . . ?
C15 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 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
_geom_bond_publ_flag
Al01 O2 1.8168(9) . ?
Al01 O3 1.7340(10) . ?
Al01 O1 1.8307(9) . ?
Al01 N2 2.0167(11) . ?
Al01 N1 2.0311(10) . ?
O2 C20 1.3262(15) . ?
O3 C21 1.4110(15) . ?
O1 C1 1.3194(15) . ?
N2 C12 1.2880(16) . ?
N2 C11 1.4662(14) . ?
N1 C9 1.2932(16) . ?
N1 C10 1.4770(15) . ?
C12 C16 1.4370(16) . ?
C12 C13 1.5142(16) . ?
C6 C9 1.4360(17) . ?
C6 C1 1.4044(17) . ?
C6 C5 1.3984(17) . ?
C9 C8 1.5087(16) . ?
C1 C2 1.4025(18) . ?
C20 C16 1.4021(17) . ?
C20 C19 1.4068(16) . ?
C5 C7 1.5134(17) . ?
C5 C4 1.3770(19) . ?
C16 C15 1.3966(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5478(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.5219(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 C14 1.5087(18) . ?
C15 C17 1.3857(18) . ?
C19 H19 0.9500 . ?
C19 C18 1.3915(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.3893(19) . ?
C18 H18 0.9500 . ?
C18 C17 1.396(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5477(18) . ?
C21 H21 1.0000 . ?
C21 C23 1.5205(18) . ?
C21 C22 1.515(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(2) . ?
C4 H4 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 H17 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.012 402 101 ' '
2 1.000 0.500 0.024 402 101 ' '
