#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024858.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_4024858
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            'C14 H14 Cl N O2'
_chemical_formula_weight         263.71
_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                 94.713(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.479(2)
_cell_length_b                   10.3508(15)
_cell_length_c                   8.7720(13)
_cell_measurement_temperature    298(2)
_cell_volume                     1310.2(3)
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_collection       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_molecular_graphics    'BRUKER 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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4997
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.9348
_exptl_absorpt_correction_T_min  0.8546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0399
_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)+(0.0691P)²+0.4167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                1498
_reflns_number_total             1710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901463k_si_002.cif
_cod_data_source_block           dt1038m
_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               4024858
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 0.45758(17) 0.6880(2) 0.4994(3) 0.0471(6) Uani 1 1 d . . .
Cl1 Cl 0.04206(6) 0.55976(10) 0.31223(12) 0.0937(4) Uani 1 1 d . . .
O1 O 0.42132(13) 0.30326(19) 0.1835(2) 0.0669(6) Uani 1 1 d . . .
O2 O 0.40136(13) 0.46553(18) 0.3380(2) 0.0623(6) Uani 1 1 d . . .
C1 C 0.37201(17) 0.3870(2) 0.2379(3) 0.0435(6) Uani 1 1 d . . .
C2 C 0.27056(16) 0.3894(2) 0.1853(3) 0.0396(6) Uani 1 1 d . . .
C3 C 0.21036(18) 0.4655(2) 0.2603(3) 0.0484(7) Uani 1 1 d . . .
H3 H 0.2329 0.5176 0.3413 0.058 Uiso 1 1 calc R . .
C4 C 0.11696(18) 0.4643(3) 0.2154(3) 0.0536(7) Uani 1 1 d . . .
C5 C 0.0823(2) 0.3889(3) 0.0959(3) 0.0609(8) Uani 1 1 d . . .
H5 H 0.0191 0.3878 0.0672 0.073 Uiso 1 1 calc R . .
C6 C 0.1418(2) 0.3149(3) 0.0188(4) 0.0666(9) Uani 1 1 d . . .
H6 H 0.1190 0.2648 -0.0639 0.080 Uiso 1 1 calc R . .
C7 C 0.23548(19) 0.3146(2) 0.0639(3) 0.0539(7) Uani 1 1 d . . .
H7 H 0.2753 0.2635 0.0118 0.065 Uiso 1 1 calc R . .
C8 C 0.39592(19) 0.7859(2) 0.5621(3) 0.0527(7) Uani 1 1 d . . .
H8A H 0.4335 0.8494 0.6201 0.063 Uiso 1 1 calc R . .
H8B H 0.3566 0.7438 0.6316 0.063 Uiso 1 1 calc R . .
C9 C 0.33641(17) 0.8529(2) 0.4391(3) 0.0443(6) Uani 1 1 d . . .
C10 C 0.24501(19) 0.8157(3) 0.4060(3) 0.0565(7) Uani 1 1 d . . .
H10 H 0.2204 0.7492 0.4614 0.068 Uiso 1 1 calc R . .
C11 C 0.1900(2) 0.8769(3) 0.2912(4) 0.0676(8) Uani 1 1 d . . .
H11 H 0.1289 0.8509 0.2691 0.081 Uiso 1 1 calc R . .
C12 C 0.2255(2) 0.9752(3) 0.2105(4) 0.0663(8) Uani 1 1 d . . .
H12 H 0.1883 1.0168 0.1341 0.080 Uiso 1 1 calc R . .
C13 C 0.3160(2) 1.0128(3) 0.2419(3) 0.0598(8) Uani 1 1 d . . .
H13 H 0.3403 1.0794 0.1863 0.072 Uiso 1 1 calc R . .
C14 C 0.37087(19) 0.9518(2) 0.3558(3) 0.0503(7) Uani 1 1 d . . .
H14 H 0.4321 0.9779 0.3767 0.060 Uiso 1 1 calc R . .
H1N1 H 0.4920(19) 0.726(3) 0.432(3) 0.052(8) Uiso 1 1 d . . .
H3N1 H 0.423(2) 0.629(3) 0.447(3) 0.062(9) Uiso 1 1 d . . .
H2N1 H 0.495(2) 0.651(3) 0.574(4) 0.068(9) Uiso 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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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
C8 N1 H1N1 109.3(17) . . ?
C8 N1 H3N1 108.8(18) . . ?
H1N1 N1 H3N1 106(2) . . ?
C8 N1 H2N1 111.2(19) . . ?
H1N1 N1 H2N1 110(3) . . ?
H3N1 N1 H2N1 111(3) . . ?
O1 C1 O2 123.5(2) . 1 ?
O1 C1 O2 123.5(2) . . ?
O1 C1 C2 118.1(2) . . ?
O2 C1 C2 118.3(2) 1 . ?
O2 C1 C2 118.3(2) . . ?
C7 C2 C3 118.7(2) . . ?
C7 C2 C1 121.1(2) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 Cl1 119.6(2) . . ?
C3 C4 Cl1 119.5(2) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.7(3) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C9 112.2(2) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C8 121.1(2) . . ?
C10 C9 C8 120.4(2) . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.9(3) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
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
N1 C8 1.485(3) . ?
N1 H1N1 0.90(3) . ?
N1 H3N1 0.90(3) . ?
N1 H2N1 0.90(3) . ?
Cl1 C4 1.739(3) . ?
O1 C1 1.243(3) . ?
O2 C1 1.245(3) . ?
C1 O2 1.245(3) 1 ?
C1 C2 1.503(3) . ?
C2 C7 1.379(4) . ?
C2 C3 1.381(3) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.495(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.375(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 H14 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 H1N1 O1 0.90(3) 1.86(3) 2.745(3) 171(2) 2_655
N1 H3N1 O2 0.90(3) 1.96(3) 2.789(3) 154(3) 1
N1 H2N1 O2 0.90(3) 2.03(3) 2.873(3) 156(3) 3_666
N1 H2N1 O1 0.90(3) 2.41(3) 3.165(3) 142(2) 3_666
