#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024864.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_4024864
loop_
_publ_author_name
'Uttam Kumar Das'
'Darshak R Trivedi'
'N. N. Adarsh'
'Parthasarathi Dastidar'
_publ_section_title
;
Supramolecular Synthons in Noncovalent Synthesis of a Class of Gelators
Derived from Simple Organic Salts: Instant Gelation of Organic Fluids at
Room Temperature via in Situ Synthesis of the Gelators
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7111
_journal_page_last               7121
_journal_paper_doi               10.1021/jo901463k
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C15 H17 N O2'
_chemical_formula_weight         243.30
_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                 100.725(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.327(3)
_cell_length_b                   6.6298(14)
_cell_length_c                   15.688(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1361.9(5)
_computing_cell_refinement       'SMART APEX II'
_computing_data_collection       'SMART APEX II'
_computing_data_reduction        'SMART APEX SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'MERCURY 2.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14428
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.052
_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     165
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0503
_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)+(0.0838P)²+0.2123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                2456
_reflns_number_total             3113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901463k_si_008.cif
_cod_data_source_block           UD0104
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024864
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
N1 N 0.06071(8) 0.69154(17) 0.80238(7) 0.0468(3) Uani 1 1 d . . .
H1A H 0.0888 0.8137 0.8078 0.070 Uiso 1 1 calc R . .
H1B H 0.0091 0.6903 0.7573 0.070 Uiso 1 1 calc R . .
H1C H 0.1073 0.6013 0.7940 0.070 Uiso 1 1 calc R . .
O1 O 0.11688(7) 1.09783(15) 0.81351(6) 0.0548(3) Uani 1 1 d . . .
O2 O 0.17198(8) 1.37501(15) 0.75920(8) 0.0640(3) Uani 1 1 d . . .
C1 C 0.18734(10) 1.20826(19) 0.79579(8) 0.0446(3) Uani 1 1 d . . .
C2 C 0.29559(9) 1.13552(18) 0.81992(8) 0.0428(3) Uani 1 1 d . . .
C3 C 0.31962(10) 0.9597(2) 0.86736(8) 0.0486(3) Uani 1 1 d . . .
H3 H 0.2676 0.8864 0.8850 0.058 Uiso 1 1 calc R . .
C4 C 0.41913(12) 0.8908(2) 0.88910(10) 0.0582(4) Uani 1 1 d . . .
C5 C 0.44392(17) 0.6984(3) 0.93983(14) 0.0882(6) Uani 1 1 d . . .
H5A H 0.4433 0.5875 0.9004 0.132 Uiso 1 1 calc R . .
H5B H 0.3939 0.6758 0.9756 0.132 Uiso 1 1 calc R . .
H5C H 0.5104 0.7094 0.9758 0.132 Uiso 1 1 calc R . .
C6 C 0.49460(12) 1.0033(3) 0.86198(12) 0.0728(5) Uani 1 1 d . . .
H6 H 0.5622 0.9608 0.8763 0.087 Uiso 1 1 calc R . .
C7 C 0.47195(13) 1.1769(3) 0.81425(14) 0.0793(5) Uani 1 1 d . . .
H7 H 0.5239 1.2491 0.7960 0.095 Uiso 1 1 calc R . .
C8 C 0.37255(11) 1.2441(2) 0.79341(10) 0.0590(4) Uani 1 1 d . . .
H8 H 0.3574 1.3622 0.7616 0.071 Uiso 1 1 calc R . .
C9 C 0.02218(11) 0.6404(3) 0.88241(10) 0.0677(5) Uani 1 1 d . . .
H9A H -0.0090 0.5078 0.8756 0.081 Uiso 1 1 calc R . .
H9B H -0.0304 0.7365 0.8898 0.081 Uiso 1 1 calc R . .
C10 C 0.10370(10) 0.6411(2) 0.96286(9) 0.0527(3) Uani 1 1 d . . .
C11 C 0.15829(13) 0.4689(3) 0.98931(11) 0.0667(4) Uani 1 1 d . . .
H11 H 0.1472 0.3524 0.9559 0.080 Uiso 1 1 calc R . .
C12 C 0.22950(15) 0.4690(4) 1.06532(14) 0.0890(7) Uani 1 1 d . . .
H12 H 0.2668 0.3528 1.0828 0.107 Uiso 1 1 calc R . .
C13 C 0.24548(16) 0.6399(5) 1.11519(13) 0.0991(8) Uani 1 1 d . . .
H13 H 0.2926 0.6386 1.1670 0.119 Uiso 1 1 calc R . .
C14 C 0.19304(19) 0.8098(4) 1.08939(13) 0.0942(7) Uani 1 1 d . . .
H14 H 0.2046 0.9256 1.1232 0.113 Uiso 1 1 calc R . .
C15 C 0.12174(14) 0.8128(3) 1.01250(12) 0.0720(5) Uani 1 1 d . . .
H15 H 0.0863 0.9308 0.9946 0.086 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O2 C1 O1 123.47(12) . 1 ?
O2 C1 O1 123.47(12) . . ?
O2 C1 C2 117.99(12) . . ?
O1 C1 C2 118.53(11) 1 . ?
O1 C1 C2 118.53(11) . . ?
C8 C2 C3 119.33(12) . . ?
C8 C2 C1 119.33(12) . . ?
C3 C2 C1 121.33(12) . . ?
C4 C3 C2 121.63(14) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C6 C4 C3 117.70(14) . . ?
C6 C4 C5 121.27(15) . . ?
C3 C4 C5 121.03(16) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.39(15) . . ?
C7 C6 H6 119.3 . . ?
C4 C6 H6 119.3 . . ?
C6 C7 C8 120.25(17) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C2 119.70(15) . . ?
C7 C8 H8 120.2 . . ?
C2 C8 H8 120.2 . . ?
N1 C9 C10 113.59(12) . . ?
N1 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 119.29(14) . . ?
C15 C10 C9 120.06(15) . . ?
C11 C10 C9 120.61(15) . . ?
C10 C11 C12 120.05(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 120.17(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.94(19) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
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
N1 C9 1.4815(19) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O1 O1 0.000(3) 1 ?
O1 C1 1.2618(16) . ?
O2 C1 1.2449(16) . ?
C1 O1 1.2618(16) 1 ?
C1 C2 1.5013(18) . ?
C2 C8 1.379(2) . ?
C2 C3 1.3878(18) . ?
C3 C4 1.3842(19) . ?
C3 H3 0.9300 . ?
C4 C6 1.381(3) . ?
C4 C5 1.507(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.5044(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.375(2) . ?
C10 C11 1.376(2) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.347(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
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
N1 H1A O1 0.89 1.92 2.7924(16) 166.6 1
N1 H1B O1 0.89 1.93 2.7733(14) 156.9 2_546
N1 H1C O2 0.89 1.86 2.7268(16) 163.6 1_545
