#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:55:20 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180485 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/54/7215481.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_7215481
loop_
_publ_author_name
'Adalder, Tapas Kumar'
'Dastidar, Parthasarathi'
_publ_section_title
;
 The role of secondary ammonium cations in controlling the conformation of
 C3-symmetric acid moieties and its implication for the design of
 supramolecular capsules
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              4867
_journal_paper_doi               10.1039/c3ce42655f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C15 H17 O6, C6 H16 N'
_chemical_formula_sum            'C21 H33 N O6'
_chemical_formula_weight         379.36
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 112.740(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.566(10)
_cell_length_b                   9.991(7)
_cell_length_c                   17.129(11)
_cell_measurement_temperature    296(2)
_cell_volume                     2299(3)
_computing_cell_refinement       'BRUKER APEX II'
_computing_data_collection       'BRUKER APEX II'
_computing_data_reduction        'BRUKER APEX II'
_computing_molecular_graphics    'MERCURY 2.3, PLATON'
_computing_publication_material  'MERCURY 2.3, PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA SCAN'
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10415
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BOLOCK
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.065
_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     254
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0866
_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)+(0.1513P)²+0.3672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2308
_refine_ls_wR_factor_ref         0.2754
_reflns_number_gt                2223
_reflns_number_total             4035
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42655f2.cif
_cod_data_source_block           iacs_ta
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7215472--7215483.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7215481
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C17A C -0.0189(11) 0.8090(16) 0.3502(10) 0.118(4) Uiso 0.43 1 d P A 1
C20A C 0.1274(10) 0.8251(14) 0.1761(8) 0.122(4) Uiso 0.57 1 d P A 1
C21A C 0.1073(10) 0.8221(15) 0.0838(9) 0.137(4) Uiso 0.58 1 d P A 1
N1A N 0.1173(4) 0.9450(5) 0.3024(3) 0.0600(14) Uiso 0.60 1 d P A 1
C17B C 0.0147(7) 0.8994(11) 0.3853(7) 0.102(3) Uiso 0.57 1 d P A 2
C20B C 0.1229(19) 0.897(3) 0.1315(19) 0.191(9) Uiso 0.43 1 d P A 2
C21B C 0.1810(19) 0.772(3) 0.1524(16) 0.182(8) Uiso 0.42 1 d P A 2
N1B N 0.0638(6) 0.8436(8) 0.2501(5) 0.066(2) Uiso 0.40 1 d P A 2
O1 O 0.4105(2) -0.0365(4) 0.1440(2) 0.1006(12) Uani 1 1 d . . .
H1 H 0.3658 -0.0497 0.0977 0.151 Uiso 1 1 calc R . .
O2 O 0.3056(3) 0.1137(4) 0.1515(2) 0.1084(13) Uani 1 1 d . . .
O3 O 0.14439(18) 0.4150(2) 0.4113(2) 0.0748(9) Uani 1 1 d . . .
H3 H 0.1914 0.4637 0.4381 0.112 Uiso 1 1 calc R . .
O4 O 0.11851(19) 0.2077(3) 0.3674(2) 0.0800(10) Uani 1 1 d . . .
O5 O 0.2177(2) -0.2860(3) 0.3781(2) 0.1017(12) Uani 1 1 d . . .
O6 O 0.2854(2) -0.4210(2) 0.48676(18) 0.0719(8) Uani 1 1 d . . .
C1 C 0.3819(3) 0.0510(5) 0.1852(3) 0.0659(11) Uani 1 1 d . . .
C2 C 0.4541(3) 0.0694(5) 0.2765(3) 0.0710(12) Uani 1 1 d . . .
H2A H 0.4828 0.1583 0.2829 0.085 Uiso 1 1 calc R . .
H2B H 0.5079 0.0053 0.2888 0.085 Uiso 1 1 calc R . .
C3 C 0.4063(2) 0.0517(4) 0.3414(2) 0.0501(9) Uani 1 1 d . . .
C4 C 0.3647(2) 0.1613(3) 0.3663(2) 0.0519(9) Uani 1 1 d . . .
C5 C 0.3581(4) 0.2976(4) 0.3229(3) 0.0824(14) Uani 1 1 d . . .
H5A H 0.3008 0.3453 0.3227 0.124 Uiso 1 1 calc R . .
H5B H 0.3523 0.2840 0.2657 0.124 Uiso 1 1 calc R . .
H5C H 0.4171 0.3486 0.3531 0.124 Uiso 1 1 calc R . .
C6 C 0.3275(2) 0.1461(3) 0.4296(2) 0.0483(9) Uani 1 1 d . . .
C7 C 0.2869(3) 0.2685(4) 0.4590(3) 0.0651(11) Uani 1 1 d . . .
H7A H 0.2976 0.2570 0.5181 0.078 Uiso 1 1 calc R . .
H7B H 0.3242 0.3467 0.4549 0.078 Uiso 1 1 calc R . .
C8 C 0.1770(3) 0.2938(4) 0.4086(2) 0.0572(10) Uani 1 1 d . . .
C9 C 0.3291(2) 0.0207(4) 0.4674(2) 0.0483(9) Uani 1 1 d . . .
C10 C 0.2845(3) 0.0053(5) 0.5337(3) 0.0810(14) Uani 1 1 d . . .
H10A H 0.2680 -0.0870 0.5371 0.121 Uiso 1 1 calc R . .
H10B H 0.2254 0.0589 0.5181 0.121 Uiso 1 1 calc R . .
H10C H 0.3319 0.0342 0.5876 0.121 Uiso 1 1 calc R . .
C11 C 0.3708(2) -0.0897(3) 0.4422(2) 0.0482(9) Uani 1 1 d . . .
C12 C 0.3765(3) -0.2243(4) 0.4854(3) 0.0625(11) Uani 1 1 d . . .
H12A H 0.3866 -0.2084 0.5440 0.075 Uiso 1 1 calc R . .
H12B H 0.4343 -0.2721 0.4852 0.075 Uiso 1 1 calc R . .
C13 C 0.2846(3) -0.3141(4) 0.4452(3) 0.0586(10) Uani 1 1 d . . .
C14 C 0.4082(2) -0.0757(4) 0.3785(2) 0.0508(9) Uani 1 1 d . . .
C15 C 0.4475(3) -0.1961(4) 0.3476(3) 0.0824(14) Uani 1 1 d . . .
H15A H 0.4524 -0.1750 0.2946 0.124 Uiso 1 1 calc R . .
H15B H 0.4029 -0.2702 0.3399 0.124 Uiso 1 1 calc R . .
H15C H 0.5121 -0.2194 0.3885 0.124 Uiso 1 1 calc R . .
C16 C 0.0160(3) 0.9148(5) 0.2996(3) 0.0867(14) Uani 1 1 d . . .
C19 C 0.1159(4) 0.9559(5) 0.2128(4) 0.0959(16) Uani 1 1 d . . .
C18 C -0.0883(6) 0.8680(10) 0.3872(6) 0.180(4) Uani 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 C17A C16 112.4(11)
C19 C20A C21A 117.2(12)
C16 N1A C19 110.7(4)
C16 C17B C18 115.2(8)
C21B C20B C19 109(2)
C16 N1B C19 107.0(6)
O2 C1 O1 121.5(4)
O2 C1 C2 124.7(4)
O1 C1 C2 113.7(4)
C1 C2 C3 113.8(3)
C4 C3 C14 120.1(3)
C4 C3 C2 120.3(3)
C14 C3 C2 119.6(3)
C3 C4 C6 119.8(3)
C3 C4 C5 120.0(4)
C6 C4 C5 120.1(4)
C4 C6 C9 120.8(3)
C4 C6 C7 119.0(3)
C9 C6 C7 120.2(3)
C8 C7 C6 113.8(3)
O4 C8 O3 119.4(3)
O4 C8 C7 123.8(3)
O3 C8 C7 116.8(3)
C11 C9 C6 119.4(3)
C11 C9 C10 120.7(3)
C6 C9 C10 119.9(3)
C14 C11 C9 120.3(3)
C14 C11 C12 120.2(3)
C9 C11 C12 119.5(3)
C11 C12 C13 115.1(3)
O5 C13 O6 123.3(4)
O5 C13 C12 122.0(4)
O6 C13 C12 114.8(3)
C11 C14 C3 119.5(3)
C11 C14 C15 120.4(4)
C3 C14 C15 120.0(4)
N1B C16 C17B 135.3(6)
N1B C16 N1A 55.4(4)
C17B C16 N1A 112.4(5)
N1B C16 C17A 108.6(7)
N1A C16 C17A 130.3(7)
C20A C19 N1A 113.7(7)
N1A C19 C20B 153.4(12)
C20A C19 N1B 72.9(7)
N1A C19 N1B 51.8(4)
C20B C19 N1B 107.2(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C17A C18 1.506(16)
C17A C16 1.571(16)
C20A C19 1.488(14)
C20A C21A 1.492(19)
N1A C16 1.489(7)
N1A C19 1.530(8)
C17B C16 1.482(11)
C17B C18 1.546(12)
C20B C21B 1.47(3)
C20B C19 1.55(3)
N1B C16 1.472(9)
N1B C19 1.617(9)
O1 C1 1.289(5)
O2 C1 1.209(5)
O3 C8 1.308(4)
O4 C8 1.223(4)
O5 C13 1.218(4)
O6 C13 1.281(4)
C1 C2 1.522(6)
C2 C3 1.532(5)
C3 C4 1.395(5)
C3 C14 1.418(5)
C4 C6 1.396(5)
C4 C5 1.537(5)
C6 C9 1.405(5)
C6 C7 1.526(5)
C7 C8 1.518(5)
C9 C11 1.405(5)
C9 C10 1.518(5)
C11 C14 1.401(5)
C11 C12 1.522(5)
C12 C13 1.536(5)
C14 C15 1.513(5)
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
O1 H1 O6 0.82 1.83 2.639(5) 168.8 4
O3 H3 O6 0.82 1.74 2.553(4) 174.2 1_565
