#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/10/2011077.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011077
loop_
_publ_author_name
'Goddard, Richard'
'Hütte, Stephan'
'Reetz, Manfred T.'
_publ_section_title
;
 Tetrabutylammonium α-acetyl-γ-butyrolactonate containing a
 three-dimensional hydrogen-bonded network
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              878
_journal_page_last               880
_journal_paper_doi               10.1107/S0108270100004959
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C16 H36 N +, C6 H7 O3 -'
_chemical_formula_sum            'C22 H43 N O3'
_chemical_formula_weight         369.57
_chemical_melting_point          428
_chemical_name_systematic
;
  tetrabutylammonium-α-acetyl-γ-butyrolactonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                89.920(10)
_cell_angle_beta                 94.100(10)
_cell_angle_gamma                95.01(2)
_cell_formula_units_Z            4
_cell_length_a                   12.309(4)
_cell_length_b                   13.659(3)
_cell_length_c                   13.6110(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.1
_cell_measurement_theta_min      12.7
_cell_volume                     2273.8(9)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS  (Enraf-Nonius, 1995)'
_computing_data_reduction        'DATAP (Coppens et al., 1965)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full .996
_diffrn_measured_fraction_theta_max .996
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .038
_diffrn_reflns_av_sigmaI/netI    .061
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11019
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         1.50
_diffrn_standards_decay_%        4.7
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          .63
_exptl_crystal_size_mid          .39
_exptl_crystal_size_min          .18
_refine_diff_density_max         .53
_refine_diff_density_min         -.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         10330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          .113
_refine_ls_R_factor_gt           .0743
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.098P)²+2.206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .219
_reflns_number_gt                7010
_reflns_number_total             10330
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1402.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2011077
_cod_database_fobs_code          2011077
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .49742(15) -.36096(15) -.36924(14) .0339(5) Uani d . 1 . . O
O2 .50227(15) -.13762(15) -.13849(13) .0322(4) Uani d . 1 . . O
O3 .51419(18) -.03879(15) -.26826(15) .0390(5) Uani d . 1 . . O
O4 -.01567(16) -.37392(16) .35216(16) .0395(5) Uani d . 1 . . O
O5 .00909(15) -.14199(13) .13132(15) .0315(4) Uani d . 1 . . O
O6 .02016(18) -.27096(16) .03429(16) .0417(5) Uani d . 1 . . O
N1 -.25003(15) .48491(13) -.47121(13) .0148(4) Uani d . 1 . . N
N2 .24988(15) .01817(14) .96618(13) .0168(4) Uani d . 1 . . N
C1 -.31881(18) .39637(16) -.43582(16) .0167(4) Uani d . 1 . . C
H1A -.3655 .3690 -.4913 .020 Uiso calc R 1 . . H
H1B -.3659 .4184 -.3877 .020 Uiso calc R 1 . . H
C2 -.25583(19) .31531(17) -.39008(17) .0200(5) Uani d . 1 . . C
H2A -.2023 .3427 -.3395 .024 Uiso calc R 1 . . H
H2B -.2172 .2850 -.4400 .024 Uiso calc R 1 . . H
C3 -.3343(2) .23811(17) -.34490(18) .0225(5) Uani d . 1 . . C
H3A -.3697 .2682 -.2926 .027 Uiso calc R 1 . . H
H3B -.3906 .2143 -.3948 .027 Uiso calc R 1 . . H
C4 -.2761(2) .15211(18) -.3035(2) .0284(6) Uani d . 1 . . C
H4A -.3278 .1058 -.2750 .043 Uiso calc R 1 . . H
H4B -.2205 .1753 -.2539 .043 Uiso calc R 1 . . H
H4C -.2431 .1208 -.3555 .043 Uiso calc R 1 . . H
C5 -.33182(18) .55141(16) -.51783(16) .0172(4) Uani d . 1 . . C
H5A -.3723 .5163 -.5726 .021 Uiso calc R 1 . . H
H5B -.3837 .5634 -.4697 .021 Uiso calc R 1 . . H
C6 -.28552(19) .64984(17) -.55504(18) .0210(5) Uani d . 1 . . C
H6A -.2297 .6404 -.6000 .025 Uiso calc R 1 . . H
H6B -.2525 .6901 -.5003 .025 Uiso calc R 1 . . H
C7 -.3783(2) .70060(18) -.60775(18) .0237(5) Uani d . 1 . . C
H7A -.4062 .6624 -.6656 .028 Uiso calc R 1 . . H
H7B -.4373 .7024 -.5644 .028 Uiso calc R 1 . . H
C8 -.3430(2) .80474(19) -.6390(2) .0304(6) Uani d . 1 . . C
H8A -.4038 .8328 -.6731 .046 Uiso calc R 1 . . H
H8B -.2845 .8035 -.6819 .046 Uiso calc R 1 . . H
H8C -.3184 .8438 -.5818 .046 Uiso calc R 1 . . H
C9 -.16980(18) .45642(17) -.54346(16) .0172(4) Uani d . 1 . . C
H9A -.1247 .5151 -.5600 .021 Uiso calc R 1 . . H
H9B -.1220 .4119 -.5106 .021 Uiso calc R 1 . . H
C10 -.21943(19) .40820(18) -.63835(16) .0213(5) Uani d . 1 . . C
H10A -.2588 .4549 -.6774 .026 Uiso calc R 1 . . H
H10B -.2706 .3529 -.6237 .026 Uiso calc R 1 . . H
C11 -.1280(2) .37318(19) -.69558(18) .0249(5) Uani d . 1 . . C
H11A -.0723 .4272 -.7018 .030 Uiso calc R 1 . . H
H11B -.0947 .3212 -.6590 .030 Uiso calc R 1 . . H
C12 -.1690(2) .3352(2) -.79786(19) .0334(6) Uani d . 1 . . C
H12A -.1090 .3136 -.8310 .050 Uiso calc R 1 . . H
H12B -.2004 .3869 -.8349 .050 Uiso calc R 1 . . H
H12C -.2235 .2811 -.7921 .050 Uiso calc R 1 . . H
C13 -.17959(18) .53591(16) -.38701(16) .0172(4) Uani d . 1 . . C
H13A -.1249 .4927 -.3638 .021 Uiso calc R 1 . . H
H13B -.1413 .5945 -.4125 .021 Uiso calc R 1 . . H
C14 -.2395(2) .56520(18) -.29993(17) .0217(5) Uani d . 1 . . C
H14A -.2687 .5068 -.2668 .026 Uiso calc R 1 . . H
H14B -.3000 .6024 -.3225 .026 Uiso calc R 1 . . H
C15 -.1610(2) .62760(19) -.22839(18) .0254(5) Uani d . 1 . . C
H15A -.0988 .5911 -.2089 .030 Uiso calc R 1 . . H
H15B -.1340 .6868 -.2616 .030 Uiso calc R 1 . . H
C16 -.2147(3) .6558(2) -.1375(2) .0384(7) Uani d . 1 . . C
H16A -.1629 .6955 -.0951 .058 Uiso calc R 1 . . H
H16B -.2394 .5975 -.1033 .058 Uiso calc R 1 . . H
H16C -.2759 .6924 -.1564 .058 Uiso calc R 1 . . H
C17 .17103(19) .03625(17) 1.04401(16) .0188(5) Uani d . 1 . . C
H17A .1231 .0847 1.0189 .023 Uiso calc R 1 . . H
H17B .1259 -.0244 1.0536 .023 Uiso calc R 1 . . H
C18 .2233(2) .07132(18) 1.14320(17) .0221(5) Uani d . 1 . . C
H18A .2692 .1318 1.1353 .027 Uiso calc R 1 . . H
H18B .2689 .0224 1.1712 .027 Uiso calc R 1 . . H
C19 .1341(2) .08878(19) 1.21214(18) .0267(5) Uani d . 1 . . C
H19A .0918 .1407 1.1857 .032 Uiso calc R 1 . . H
H19B .0850 .0295 1.2153 .032 Uiso calc R 1 . . H
C20 .1814(3) .1171(2) 1.3154(2) .0356(6) Uani d . 1 . . C
H20A .1231 .1276 1.3563 .053 Uiso calc R 1 . . H
H20B .2291 .1763 1.3126 .053 Uiso calc R 1 . . H
H20C .2219 .0652 1.3424 .053 Uiso calc R 1 . . H
C21 .17774(19) -.01864(17) .87630(16) .0193(5) Uani d . 1 . . C
H21A .1280 .0307 .8582 .023 Uiso calc R 1 . . H
H21B .1338 -.0774 .8946 .023 Uiso calc R 1 . . H
C22 .2368(2) -.04243(18) .78587(17) .0229(5) Uani d . 1 . . C
H22A .2794 .0159 .7647 .027 Uiso calc R 1 . . H
H22B .2863 -.0926 .8018 .027 Uiso calc R 1 . . H
C23 .1527(2) -.0789(2) .70363(19) .0319(6) Uani d . 1 . . C
H23A .1095 -.1362 .7262 .038 Uiso calc R 1 . . H
H23B .1037 -.0282 .6884 .038 Uiso calc R 1 . . H
C24 .2052(3) -.1054(3) .6108(2) .0457(8) Uani d . 1 . . C
H24A .1493 -.1278 .5611 .069 Uiso calc R 1 . . H
H24B .2526 -.1566 .6251 .069 Uiso calc R 1 . . H
H24C .2470 -.0485 .5874 .069 Uiso calc R 1 . . H
C25 .32915(18) -.05611(17) 1.00083(16) .0184(5) Uani d . 1 . . C
H25A .3801 -.0622 .9504 .022 Uiso calc R 1 . . H
H25B .3710 -.0302 1.0596 .022 Uiso calc R 1 . . H
C26 .2786(2) -.15765(17) 1.02362(18) .0224(5) Uani d . 1 . . C
H26A .2413 -.1875 .9644 .027 Uiso calc R 1 . . H
H26B .2254 -.1533 1.0724 .027 Uiso calc R 1 . . H
C27 .3686(2) -.22050(18) 1.06299(19) .0260(5) Uani d . 1 . . C
H27A .4243 -.2198 1.0159 .031 Uiso calc R 1 . . H
H27B .4026 -.1918 1.1240 .031 Uiso calc R 1 . . H
C28 .3263(3) -.3265(2) 1.0816(2) .0351(6) Uani d . 1 . . C
H28A .3857 -.3625 1.1068 .053 Uiso calc R 1 . . H
H28B .2947 -.3560 1.0210 .053 Uiso calc R 1 . . H
H28C .2717 -.3278 1.1287 .053 Uiso calc R 1 . . H
C29 .32066(18) .11107(17) .94416(17) .0185(5) Uani d . 1 . . C
H29A .3660 .1303 1.0034 .022 Uiso calc R 1 . . H
H29B .3691 .0957 .8943 .022 Uiso calc R 1 . . H
C30 .26102(19) .19837(17) .90925(17) .0199(5) Uani d . 1 . . C
H30A .2105 .2142 .9572 .024 Uiso calc R 1 . . H
H30B .2194 .1826 .8472 .024 Uiso calc R 1 . . H
C31 .3441(2) .28674(18) .89582(19) .0243(5) Uani d . 1 . . C
H31A .3852 .3020 .9582 .029 Uiso calc R 1 . . H
H31B .3953 .2696 .8490 .029 Uiso calc R 1 . . H
C32 .2901(2) .37753(19) .8593(2) .0317(6) Uani d . 1 . . C
H32A .3451 .4311 .8531 .048 Uiso calc R 1 . . H
H32B .2395 .3950 .9054 .048 Uiso calc R 1 . . H
H32C .2517 .3637 .7963 .048 Uiso calc R 1 . . H
C33 .4833(2) -.3546(2) -.1960(2) .0363(6) Uani d . 1 . . C
H33A .4077 -.3755 -.1892 .054 Uiso calc R 1 . . H
H33B .5091 -.3086 -.1444 .054 Uiso calc R 1 . . H
H33C .5254 -.4106 -.1914 .054 Uiso calc R 1 . . H
C34 .49556(19) -.3053(2) -.29612(19) .0272(6) Uani d . 1 . . C
C35 .5024(2) -.2038(2) -.30395(18) .0271(5) Uani d . 1 . . C
C36 .5125(3) -.1528(2) -.4010(2) .0379(7) Uani d . 1 . . C
H36A .4511 -.1734 -.4472 .046 Uiso calc R 1 . . H
H36B .5799 -.1657 -.4295 .046 Uiso calc R 1 . . H
C37 .5124(3) -.0453(2) -.3735(2) .0426(8) Uani d . 1 . . C
H37A .5762 -.0081 -.3969 .051 Uiso calc R 1 . . H
H37B .4475 -.0187 -.4034 .051 Uiso calc R 1 . . H
C38 .5050(2) -.1330(2) -.22900(19) .0270(5) Uani d . 1 . . C
C39 -.0225(3) -.1984(2) .3430(3) .0440(8) Uani d . 1 . . C
H39A -.0553 -.2061 .4047 .066 Uiso calc R 1 . . H
H39B -.0676 -.1621 .2984 .066 Uiso calc R 1 . . H
H39C .0486 -.1635 .3534 .066 Uiso calc R 1 . . H
C40 -.0114(2) -.2987(2) .2994(2) .0334(6) Uani d . 1 . . C
C41 .0055(2) -.3066(2) .1976(2) .0322(6) Uani d . 1 . . C
C42 .0169(3) -.4028(2) .1493(2) .0391(7) Uani d . 1 . . C
H42A -.0444 -.4500 .1609 .047 Uiso calc R 1 . . H
H42B .0843 -.4297 .1730 .047 Uiso calc R 1 . . H
C43 .0182(3) -.3765(2) .0408(2) .0436(7) Uani d . 1 . . C
H43A .0824 -.3989 .0135 .052 Uiso calc R 1 . . H
H43B -.0463 -.4072 .0044 .052 Uiso calc R 1 . . H
C44 .0098(2) -.2309(2) .1287(2) .0320(6) Uani d . 1 . . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_publ_flag
C38 O3 C37 109.3(2) n
C44 O6 C43 109.6(2) n
C1 N1 C9 111.89(17) n
C1 N1 C13 111.54(16) n
C9 N1 C13 104.95(16) n
C1 N1 C5 104.95(16) n
C9 N1 C5 112.00(16) n
C13 N1 C5 111.69(17) n
C29 N2 C21 111.73(17) n
C29 N2 C25 105.51(17) n
C21 N2 C25 111.68(17) n
C29 N2 C17 111.50(17) n
C21 N2 C17 105.07(17) n
C25 N2 C17 111.50(17) n
N1 C1 C2 115.65(18) n
C1 C2 C3 109.90(19) n
C4 C3 C2 111.9(2) n
C6 C5 N1 116.57(18) n
C5 C6 C7 108.45(19) n
C8 C7 C6 112.8(2) n
C10 C9 N1 116.05(18) n
C9 C10 C11 108.82(19) n
C12 C11 C10 112.3(2) n
C14 C13 N1 115.86(18) n
C13 C14 C15 109.6(2) n
C16 C15 C14 112.3(2) n
C18 C17 N2 115.65(19) n
C17 C18 C19 109.5(2) n
C20 C19 C18 111.9(2) n
N2 C21 C22 116.08(19) n
C23 C22 C21 109.1(2) n
C24 C23 C22 112.4(2) n
C26 C25 N2 116.03(19) n
C25 C26 C27 109.0(2) n
C28 C27 C26 112.8(2) n
C30 C29 N2 116.36(19) n
C29 C30 C31 109.41(19) n
C32 C31 C30 112.5(2) n
O1 C34 C35 122.6(3) n
O1 C34 C33 116.9(3) n
C35 C34 C33 120.4(2) n
C34 C35 C38 128.8(2) n
C34 C35 C36 122.0(2) n
C38 C35 C36 109.2(2) n
C35 C36 C37 102.8(2) n
O3 C37 C36 107.9(2) n
O2 C38 O3 115.8(2) n
O2 C38 C35 133.7(3) n
O3 C38 C35 110.5(2) n
O4 C40 C41 120.0(3) n
O4 C40 C39 120.8(3) n
C41 C40 C39 119.2(3) n
C44 C41 C40 127.1(3) n
C44 C41 C42 110.5(3) n
C40 C41 C42 122.3(3) n
C41 C42 C43 103.1(2) n
O6 C43 C42 107.2(3) n
O5 C44 C41 135.8(3) n
O5 C44 O6 115.0(2) n
C41 C44 O6 109.2(2) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C34 . 1.256(3) y
O2 C38 . 1.236(3) y
O3 C38 . 1.391(3) y
O3 C37 . 1.434(3) y
O4 C40 . 1.253(3) y
O5 C44 . 1.216(3) y
O6 C44 . 1.416(4) n
O6 C43 . 1.442(4) n
N1 C1 . 1.513(3) n
N1 C9 . 1.517(3) n
N1 C13 . 1.518(3) n
N1 C5 . 1.519(3) n
N2 C29 . 1.517(3) n
N2 C21 . 1.519(3) n
N2 C25 . 1.520(3) n
N2 C17 . 1.522(3) n
C1 C2 . 1.514(3) n
C2 C3 . 1.526(3) n
C3 C4 . 1.516(3) n
C5 C6 . 1.515(3) n
C6 C7 . 1.523(3) n
C7 C8 . 1.520(3) n
C9 C10 . 1.515(3) n
C10 C11 . 1.524(3) n
C11 C12 . 1.522(3) n
C13 C14 . 1.512(3) n
C14 C15 . 1.527(3) n
C15 C16 . 1.509(4) n
C17 C18 . 1.513(3) n
C18 C19 . 1.529(3) n
C19 C20 . 1.519(4) n
C21 C22 . 1.523(3) n
C22 C23 . 1.523(3) n
C23 C24 . 1.518(4) n
C25 C26 . 1.511(3) n
C26 C27 . 1.527(3) n
C27 C28 . 1.523(4) n
C29 C30 . 1.513(3) n
C30 C31 . 1.532(3) n
C31 C32 . 1.524(3) n
C33 C34 . 1.531(4) n
C34 C35 . 1.387(4) y
C35 C38 . 1.403(4) y
C35 C36 . 1.500(4) n
C36 C37 . 1.516(4) n
C39 C40 . 1.513(4) n
C40 C41 . 1.422(4) y
C41 C44 . 1.394(4) y
C41 C42 . 1.492(4) n
C42 C43 . 1.520(4) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652293
2 PubChem 139057777
