#------------------------------------------------------------------------------
#$Date: 2016-03-24 13:04:12 +0100 (jue 24 de mar de 2016) $
#$Revision: 179650 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/03/4510381.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_4510381
loop_
_publ_author_name
'Carter, Kelsey K.'
'Rycenga, Halley B.'
'McNeil, Anne J.'
_publ_section_title
;
 Improving Hg-Triggered Gelation via Structural Modifications.
;
_journal_issue                   12
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_page_first              3522
_journal_page_last               3527
_journal_paper_doi               10.1021/la404567b
_journal_volume                  30
_journal_year                    2014
_chemical_formula_moiety         'C8 H5 Cl N2 O'
_chemical_formula_sum            'C8 H5 Cl N2 O'
_chemical_formula_weight         180.59
_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                 93.081(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.67810(10)
_cell_length_b                   4.72700(10)
_cell_length_c                   26.8696(19)
_cell_measurement_reflns_used    10009
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.30
_cell_volume                     720.15(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      85(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15464
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         3.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.228
_exptl_absorpt_correction_T_max  0.7021
_exptl_absorpt_correction_T_min  0.5334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.043(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.0638P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                1197
_reflns_number_total             1313
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la404567b_si_002.cif
_cod_data_source_block           clqox
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4510381
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
O1 O 0.2793(2) 0.24974(19) 0.50343(5) 0.0169(4) Uani 1 1 d .
Cl1 Cl 0.42039(7) 1.24469(6) 0.294043(13) 0.0133(2) Uani 1 1 d .
N1 N -0.1163(2) 0.3811(2) 0.39873(5) 0.0137(4) Uani 1 1 d .
N2 N 0.3172(3) 0.5674(3) 0.44052(5) 0.0124(3) Uani 1 1 d .
H2 H 0.454(4) 0.621(4) 0.4565(7) 0.016(5) Uiso 1 1 d .
C1 C 0.2633(3) 0.9973(3) 0.32704(5) 0.0119(4) Uani 1 1 d .
C2 C 0.0449(3) 0.9107(3) 0.30642(5) 0.0132(4) Uani 1 1 d .
H2A H -0.0159 0.9881 0.2766 0.016 Uiso 1 1 calc R
C3 C -0.0797(3) 0.7083(3) 0.33099(6) 0.0135(4) Uani 1 1 d .
H3A H -0.2262 0.6492 0.3177 0.016 Uiso 1 1 calc R
C4 C 0.0122(3) 0.5911(3) 0.37574(5) 0.0121(4) Uani 1 1 d .
C5 C 0.2308(3) 0.6866(3) 0.39599(6) 0.0113(4) Uani 1 1 d .
C6 C 0.3588(3) 0.8934(3) 0.37175(5) 0.0119(4) Uani 1 1 d .
H6A H 0.5029 0.9585 0.3853 0.014 Uiso 1 1 calc R
C7 C -0.0243(3) 0.2730(3) 0.43942(7) 0.0140(4) Uani 1 1 d .
H7A H -0.1078 0.1299 0.4544 0.017 Uiso 1 1 calc R
C8 C 0.2014(3) 0.3584(3) 0.46377(5) 0.0127(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0190(8) 0.0192(7) 0.0122(7) 0.0037(3) -0.0030(6) -0.0046(4)
Cl1 0.0149(4) 0.0140(3) 0.0109(3) 0.00171(10) -0.0003(2) -0.00298(11)
N1 0.0133(8) 0.0147(7) 0.0132(7) -0.0020(4) 0.0016(6) -0.0016(5)
N2 0.0122(8) 0.0144(6) 0.0102(6) 0.0002(5) -0.0025(6) -0.0026(5)
C1 0.0140(9) 0.0112(7) 0.0108(7) -0.0014(5) 0.0026(6) -0.0001(5)
C2 0.0155(9) 0.0132(7) 0.0106(7) -0.0007(5) -0.0020(6) 0.0019(6)
C3 0.0110(9) 0.0164(7) 0.0130(8) -0.0032(6) -0.0018(7) 0.0000(6)
C4 0.0116(9) 0.0121(7) 0.0126(7) -0.0026(5) 0.0012(6) 0.0001(6)
C5 0.0124(9) 0.0123(6) 0.0093(7) -0.0022(6) -0.0003(6) 0.0015(6)
C6 0.0117(9) 0.0125(7) 0.0115(7) -0.0024(5) -0.0011(6) -0.0007(6)
C7 0.0155(10) 0.0151(8) 0.0116(9) -0.0002(5) 0.0028(7) -0.0025(6)
C8 0.0152(10) 0.0126(8) 0.0105(7) -0.0011(6) 0.0018(6) 0.0001(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C7 N1 C4 117.30(14)
C8 N2 C5 122.31(14)
C6 C1 C2 122.76(14)
C6 C1 Cl1 119.58(12)
C2 C1 Cl1 117.66(11)
C3 C2 C1 118.84(15)
C2 C3 C4 120.56(15)
N1 C4 C3 118.81(14)
N1 C4 C5 122.01(14)
C3 C4 C5 119.18(14)
N2 C5 C6 121.08(15)
N2 C5 C4 117.92(15)
C6 C5 C4 120.99(15)
C1 C6 C5 117.64(15)
N1 C7 C8 125.02(14)
O1 C8 N2 122.46(15)
O1 C8 C7 122.12(14)
N2 C8 C7 115.40(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.243(2)
Cl1 C1 1.7420(15)
N1 C7 1.291(2)
N1 C4 1.3957(18)
N2 C8 1.3574(19)
N2 C5 1.388(2)
C1 C6 1.381(2)
C1 C2 1.392(2)
C2 C3 1.380(2)
C3 C4 1.399(2)
C4 C5 1.403(2)
C5 C6 1.400(2)
C7 C8 1.464(3)
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
N2 H2 O1 0.90(2) 1.91(2) 2.809(2) 173.0(17) 3_666
