#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150557.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_7150557
loop_
_publ_author_name
'Winkelmann, Ole'
'Näther, Christian'
'Lüning, Ulrich'
_publ_section_title
;
 Organocatalysis by bimacrocyclic NHCs: unexpected formation of a
 cyclic hemiacetal instead of a γ-butyrolactone
;
_journal_issue                   3
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              553
_journal_page_last               556
_journal_paper_doi               10.1039/b815828b
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C37 H53 Cl7 N2 O4'
_chemical_formula_weight         837.96
_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                 128.674(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.471(3)
_cell_length_b                   12.5614(7)
_cell_length_c                   16.7632(14)
_cell_measurement_reflns_used    5299
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      2.5
_cell_volume                     4351.7(9)
_computing_cell_refinement       'STOE IPDS-1 program package'
_computing_data_collection       'STOE IPDS-1 program package'
_computing_data_reduction        'STOE IPDS-1 program package'
_computing_molecular_graphics    'XP in SHELXTL-PC'
_computing_publication_material  'XCIF in SHELXTL-PC'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS-1'
_diffrn_measurement_method       'Phi 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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9095
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.82
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3828
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0628
_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)+(0.1066P)²+0.0104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1870
_reflns_number_gt                2266
_reflns_number_total             3828
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b815828b.txt
_cod_data_source_block           luen25
_cod_original_cell_volume        4351.6(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7150557
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54506(16) 0.7494(2) 0.49454(19) 0.0712(9) Uani 1 1 d . . .
O2 O 0.38466(12) 0.5570(2) 0.20630(18) 0.0513(6) Uani 1 1 d . . .
N1 N 0.48820(13) 0.6881(2) 0.30216(19) 0.0374(6) Uani 1 1 d . . .
C1 C 0.46560(17) 0.6476(3) 0.3545(2) 0.0437(8) Uani 1 1 d . . .
C2 C 0.41330(17) 0.5787(3) 0.3057(3) 0.0477(9) Uani 1 1 d . . .
C3 C 0.3931(2) 0.5375(4) 0.3581(4) 0.0673(11) Uani 1 1 d . . .
H3 H 0.3583 0.4893 0.3262 0.081 Uiso 1 1 calc R . .
C4 C 0.4248(3) 0.5683(4) 0.4580(4) 0.0756(13) Uani 1 1 d . . .
H4 H 0.4113 0.5393 0.4938 0.091 Uiso 1 1 calc R . .
C5 C 0.4744(2) 0.6384(4) 0.5066(3) 0.0684(12) Uani 1 1 d . . .
H5 H 0.4942 0.6592 0.5742 0.082 Uiso 1 1 calc R . .
C6 C 0.4956(2) 0.6792(3) 0.4548(3) 0.0553(10) Uani 1 1 d . . .
C7 C 0.5751(3) 0.7888(5) 0.5968(3) 0.0920(17) Uani 1 1 d . . .
H7A H 0.5419 0.8143 0.6009 0.110 Uiso 1 1 calc R . .
H7B H 0.5992 0.7313 0.6467 0.110 Uiso 1 1 calc R . .
C8 C 0.6186(4) 0.8749(6) 0.6193(4) 0.120(2) Uani 1 1 d . . .
H8A H 0.6392 0.9001 0.6887 0.144 Uiso 1 1 calc R . .
H8B H 0.5927 0.9339 0.5726 0.144 Uiso 1 1 calc R . .
C9 C 0.6692(4) 0.8510(5) 0.6119(5) 0.111(2) Uani 1 1 d . . .
H9A H 0.6990 0.9116 0.6392 0.133 Uiso 1 1 calc R . .
H9B H 0.6494 0.8439 0.5395 0.133 Uiso 1 1 calc R . .
C10 C 0.7073(3) 0.7535(6) 0.6661(5) 0.108(2) Uani 1 1 d . . .
H10A H 0.6786 0.6917 0.6333 0.130 Uiso 1 1 calc R . .
H10B H 0.7229 0.7566 0.7366 0.130 Uiso 1 1 calc R . .
C11 C 0.7661(4) 0.7369(6) 0.6678(5) 0.124(3) Uani 1 1 d . . .
H11A H 0.7528 0.7551 0.6003 0.149 Uiso 1 1 calc R . .
H11B H 0.8002 0.7869 0.7171 0.149 Uiso 1 1 calc R . .
C12 C 0.7942(3) 0.6275(6) 0.6946(5) 0.111(2) Uani 1 1 d . . .
H12A H 0.8091 0.6100 0.7632 0.133 Uiso 1 1 calc R . .
H12B H 0.8320 0.6273 0.6967 0.133 Uiso 1 1 calc R . .
C13 C 0.7485(2) 0.5431(5) 0.6224(4) 0.0859(15) Uani 1 1 d . . .
H13A H 0.7111 0.5429 0.6216 0.103 Uiso 1 1 calc R . .
H13B H 0.7700 0.4740 0.6491 0.103 Uiso 1 1 calc R . .
C14 C 0.7239(2) 0.5531(4) 0.5138(3) 0.0760(14) Uani 1 1 d . . .
H14A H 0.6978 0.6180 0.4839 0.091 Uiso 1 1 calc R . .
H14B H 0.7610 0.5609 0.5145 0.091 Uiso 1 1 calc R . .
C15 C 0.6838(2) 0.4602(4) 0.4466(3) 0.0676(12) Uani 1 1 d . . .
H15A H 0.7097 0.3951 0.4768 0.081 Uiso 1 1 calc R . .
H15B H 0.6465 0.4526 0.4455 0.081 Uiso 1 1 calc R . .
C16 C 0.6600(2) 0.4697(4) 0.3402(3) 0.0653(11) Uani 1 1 d . . .
H16A H 0.6963 0.4828 0.3396 0.078 Uiso 1 1 calc R . .
H16B H 0.6384 0.4037 0.3025 0.078 Uiso 1 1 calc R . .
C17 C 0.5000 0.6304(3) 0.2500 0.0340(10) Uani 1 2 d S . .
H17 H 0.5000 0.5556 0.2500 0.041 Uiso 1 2 calc SR . .
C18 C 0.4854(2) 0.8021(3) 0.2768(3) 0.0539(10) Uani 1 1 d . . .
H18A H 0.5108 0.8461 0.3387 0.065 Uiso 1 1 calc R . .
H18B H 0.4407 0.8281 0.2317 0.065 Uiso 1 1 calc R . .
C19 C 0.8971(3) 0.6646(4) 1.0907(4) 0.106(2) Uani 1 1 d D . .
H19 H 0.9209 0.7300 1.1290 0.127 Uiso 1 1 calc R A 1
Cl1 Cl 0.5000 0.35635(9) 0.2500 0.0462(4) Uani 1 2 d S B 1
Cl2 Cl 0.8297(5) 0.6879(10) 0.9799(9) 0.199(6) Uani 0.381(8) 1 d PD C 1
Cl3 Cl 0.8945(5) 0.5693(8) 1.1652(6) 0.163(4) Uani 0.381(8) 1 d PD C 1
Cl4 Cl 0.9431(5) 0.5770(8) 1.0636(11) 0.188(6) Uani 0.381(8) 1 d PD C 1
Cl2' Cl 0.8347(3) 0.6916(4) 0.9597(3) 0.1096(16) Uani 0.619(8) 1 d PD C 2
Cl3' Cl 0.8553(3) 0.6610(5) 1.1442(2) 0.150(3) Uani 0.619(8) 1 d PD C 2
Cl4' Cl 0.9405(4) 0.5622(5) 1.1109(6) 0.227(6) Uani 0.619(8) 1 d PD C 2
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'
Cl Cl 0.1484 0.1585 '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
C6 O1 C7 116.8(4) . . ?
C2 O2 C16 117.3(3) . 2_655 ?
C17 N1 C1 125.2(3) . . ?
C17 N1 C18 109.4(3) . . ?
C1 N1 C18 123.7(3) . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 N1 120.5(3) . . ?
C6 C1 N1 119.7(3) . . ?
O2 C2 C3 124.2(4) . . ?
O2 C2 C1 115.8(3) . . ?
C3 C2 C1 120.0(4) . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 122.7(4) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
O1 C6 C1 115.2(4) . . ?
O1 C6 C5 125.0(4) . . ?
C1 C6 C5 119.8(4) . . ?
C8 C7 O1 108.8(5) . . ?
C8 C7 H7A 109.9 . . ?
O1 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
O1 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 C9 116.7(6) . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 C10 115.5(6) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 C11 114.4(7) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 115.8(6) . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 C13 114.3(5) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 116.1(5) . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
C14 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C15 C14 C13 114.1(4) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 114.1(4) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
O2 C16 C15 107.5(3) 2_655 . ?
O2 C16 H16A 110.2 2_655 . ?
C15 C16 H16A 110.2 . . ?
O2 C16 H16B 110.2 2_655 . ?
C15 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
N1 C17 N1 113.1(4) 2_655 . ?
N1 C17 H17 123.4 2_655 . ?
N1 C17 H17 123.4 . . ?
N1 C18 C18 102.6(2) . 2_655 ?
N1 C18 H18A 111.2 . . ?
C18 C18 H18A 111.2 2_655 . ?
N1 C18 H18B 111.2 . . ?
C18 C18 H18B 111.2 2_655 . ?
H18A C18 H18B 109.2 . . ?
Cl2 C19 Cl4' 121.3(7) . . ?
Cl2 C19 Cl3 115.9(7) . . ?
Cl4' C19 Cl3 69.4(5) . . ?
Cl2 C19 Cl2' 13.7(7) . . ?
Cl4' C19 Cl2' 113.9(5) . . ?
Cl3 C19 Cl2' 126.2(4) . . ?
Cl2 C19 Cl3' 89.8(7) . . ?
Cl4' C19 Cl3' 116.9(5) . . ?
Cl3 C19 Cl3' 47.5(3) . . ?
Cl2' C19 Cl3' 103.5(4) . . ?
Cl2 C19 Cl4 104.2(6) . . ?
Cl4' C19 Cl4 26.8(5) . . ?
Cl3 C19 Cl4 95.2(5) . . ?
Cl2' C19 Cl4 93.2(6) . . ?
Cl3' C19 Cl4 142.0(5) . . ?
Cl2 C19 H19 113.2 . . ?
Cl4' C19 H19 116.5 . . ?
Cl3 C19 H19 113.2 . . ?
Cl2' C19 H19 111.5 . . ?
Cl3' C19 H19 92.1 . . ?
Cl4 C19 H19 113.2 . . ?
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
O1 C6 1.357(5) . ?
O1 C7 1.452(5) . ?
O2 C2 1.359(4) . ?
O2 C16 1.435(5) 2_655 ?
N1 C17 1.315(3) . ?
N1 C1 1.429(4) . ?
N1 C18 1.483(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.395(5) . ?
C2 C3 1.384(6) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.351(7) . ?
C4 H4 0.9400 . ?
C5 C6 1.395(6) . ?
C5 H5 0.9400 . ?
C7 C8 1.447(9) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.451(10) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.481(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.553(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.491(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.491(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.509(7) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.504(7) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.481(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 O2 1.435(5) 2_655 ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 N1 1.315(3) 2_655 ?
C17 H17 0.9400 . ?
C18 C18 1.508(8) 2_655 ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 Cl2 1.605(10) . ?
C19 Cl4' 1.613(8) . ?
C19 Cl3 1.761(8) . ?
C19 Cl2' 1.770(6) . ?
C19 Cl3' 1.810(7) . ?
C19 Cl4 1.895(11) . ?
C19 H19 0.9900 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190121
