#------------------------------------------------------------------------------
#$Date: 2019-11-22 18:59:12 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231248 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/63/4516322.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_4516322
loop_
_publ_author_name
'Duggirala, Naga Kiran'
'Wood, Geoffrey P. F.'
'Fischer, Addison'
'Wojtas, Łukasz'
'Perry, Miranda L.'
'Zaworotko, Michael J.'
_publ_section_title
;
 Hydrogen Bond Hierarchy: Persistent
 Phenol···Chloride Hydrogen Bonds in the Presence of
 Carboxylic Acid Moieties
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4341
_journal_paper_doi               10.1021/acs.cgd.5b00628
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         '2(C11 H8 O3), C5 H6 N, Cl'
_chemical_formula_sum            'C27 H22 Cl N O6'
_chemical_formula_weight         491.91
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/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                 106.166(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.8495(9)
_cell_length_b                   11.3672(4)
_cell_length_c                   8.5460(3)
_cell_measurement_temperature    228(2)
_cell_volume                     2318.53(14)
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_publication_material  'OLEX2 (Dolomanov,2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008), OLEX2 (2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      228(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10107
_diffrn_reflns_theta_full        68.26
_diffrn_reflns_theta_max         68.26
_diffrn_reflns_theta_min         6.49
_exptl_absorpt_coefficient_mu    1.842
_exptl_absorpt_correction_T_max  0.8666
_exptl_absorpt_correction_T_min  0.6079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0371
_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)+(0.0548P)²+0.9697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                1751
_reflns_number_total             2060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00628_si_022.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4516322
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Cl1 Cl 0.5000 -0.07328(5) 0.2500 0.0637(3) Uani 1 2 d S . .
O1 O 0.26476(5) 0.33386(10) -0.33055(14) 0.0429(3) Uani 1 1 d . . .
H1 H 0.2516 0.3548 -0.4327 0.064 Uiso 0.30(3) 1 d PR A 2
C2 C 0.31231(6) 0.31842(13) 0.00700(19) 0.0317(4) Uani 1 1 d . . .
H2 H 0.2958 0.3900 -0.0362 0.038 Uiso 1 1 calc R . .
C3 C 0.33771(6) 0.30899(12) 0.17545(18) 0.0296(3) Uani 1 1 d . . .
O4 O 0.28574(5) 0.14598(10) -0.36014(13) 0.0447(3) Uani 1 1 d . . .
H4 H 0.2678 0.1569 -0.4807 0.067 Uiso 0.70(3) 1 d PR A 1
O5 O 0.42023(6) 0.28510(13) 0.67029(15) 0.0543(4) Uani 1 1 d . . .
C6 C 0.31124(6) 0.22497(13) -0.09565(18) 0.0320(4) Uani 1 1 d . . .
C7 C 0.28545(6) 0.23763(13) -0.27251(18) 0.0320(4) Uani 1 1 d . . .
C8 C 0.36242(6) 0.20009(13) 0.24043(18) 0.0312(4) Uani 1 1 d . . .
C9 C 0.34028(7) 0.40409(14) 0.2846(2) 0.0361(4) Uani 1 1 d . . .
H9 H 0.3231 0.4760 0.2448 0.043 Uiso 1 1 calc R . .
C10 C 0.38992(7) 0.19119(14) 0.40825(19) 0.0356(4) Uani 1 1 d . . .
H10 H 0.4063 0.1194 0.4515 0.043 Uiso 1 1 calc R . .
C11 C 0.35889(7) 0.10394(13) 0.13228(19) 0.0363(4) Uani 1 1 d . . .
H11 H 0.3739 0.0307 0.1737 0.044 Uiso 1 1 calc R . .
C12 C 0.39292(7) 0.28602(15) 0.50830(19) 0.0375(4) Uani 1 1 d . . .
C13 C 0.36708(7) 0.39301(14) 0.44558(19) 0.0392(4) Uani 1 1 d . . .
H13 H 0.3684 0.4572 0.5159 0.047 Uiso 1 1 calc R . .
C14 C 0.33425(7) 0.11565(14) -0.02986(19) 0.0362(4) Uani 1 1 d . . .
H14 H 0.3324 0.0507 -0.0992 0.043 Uiso 1 1 calc R . .
C15 C 0.47707(9) 0.2487(2) 0.1118(3) 0.0649(6) Uani 1 1 d . . .
H15 H 0.4614 0.2057 0.0159 0.078 Uiso 1 1 calc R . .
N16 N 0.5000 0.1939(2) 0.2500 0.0582(7) Uani 1 2 d S . .
C17 C 0.47637(11) 0.3675(2) 0.1096(4) 0.0837(8) Uani 1 1 d . . .
H17 H 0.4598 0.4085 0.0126 0.100 Uiso 1 1 calc R . .
C19 C 0.5000 0.4269(3) 0.2500 0.0996(17) Uani 1 2 d S . .
H19 H 0.5000 0.512(5) 0.2500 0.132(16) Uiso 1 2 d S . .
H5 H 0.4363(10) 0.228(2) 0.690(3) 0.064(8) Uiso 1 1 d . . .
H16 H 0.5000 0.117(3) 0.2500 0.080(11) Uiso 1 2 d S . .
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'
Cl Cl 0.3639 0.7018 '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'
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
C7 O1 H1 129.1 . .
C6 C2 C3 121.24(14) . .
C6 C2 H2 119.4 . .
C3 C2 H2 119.4 . .
C2 C3 C9 122.73(13) . .
C2 C3 C8 119.18(13) . .
C9 C3 C8 118.09(14) . .
C7 O4 H4 115.0 . .
C12 O5 H5 108.8(18) . .
C2 C6 C14 119.40(14) . .
C2 C6 C7 120.31(14) . .
C14 C6 C7 120.28(13) . .
O1 C7 O4 123.13(14) . .
O1 C7 C6 120.32(14) . .
O4 C7 C6 116.55(13) . .
C10 C8 C11 122.14(14) . .
C10 C8 C3 119.56(14) . .
C11 C8 C3 118.30(14) . .
C13 C9 C3 121.04(14) . .
C13 C9 H9 119.5 . .
C3 C9 H9 119.5 . .
C12 C10 C8 120.45(14) . .
C12 C10 H10 119.8 . .
C8 C10 H10 119.8 . .
C14 C11 C8 121.23(14) . .
C14 C11 H11 119.4 . .
C8 C11 H11 119.4 . .
O5 C12 C10 123.75(15) . .
O5 C12 C13 116.01(15) . .
C10 C12 C13 120.23(15) . .
C9 C13 C12 120.57(14) . .
C9 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C11 C14 C6 120.59(14) . .
C11 C14 H14 119.7 . .
C6 C14 H14 119.7 . .
N16 C15 C17 119.1(2) . .
N16 C15 H15 120.4 . .
C17 C15 H15 120.4 . .
C15 N16 C15 123.5(3) 2_655 .
C15 N16 H16 118.26(14) 2_655 .
C15 N16 H16 118.26(14) . .
C15 C17 C19 118.9(3) . .
C15 C17 H17 120.5 . .
C19 C17 H17 120.5 . .
C17 C19 C17 120.4(3) . 2_655
C17 C19 H19 119.78(17) . .
C17 C19 H19 119.78(17) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.2510(18) .
O1 H1 0.8758 .
C2 C6 1.373(2) .
C2 C3 1.406(2) .
C2 H2 0.9400 .
C3 C9 1.418(2) .
C3 C8 1.424(2) .
O4 C7 1.2842(18) .
O4 H4 1.0097 .
O5 C12 1.3616(19) .
O5 H5 0.75(2) .
C6 C14 1.417(2) .
C6 C7 1.475(2) .
C8 C10 1.410(2) .
C8 C11 1.418(2) .
C9 C13 1.357(2) .
C9 H9 0.9400 .
C10 C12 1.365(2) .
C10 H10 0.9400 .
C11 C14 1.357(2) .
C11 H11 0.9400 .
C12 C13 1.410(2) .
C13 H13 0.9400 .
C14 H14 0.9400 .
C15 N16 1.317(3) .
C15 C17 1.351(3) .
C15 H15 0.9400 .
N16 C15 1.317(3) 2_655
N16 H16 0.87(4) .
C17 C19 1.359(3) .
C17 H17 0.9400 .
C19 C17 1.359(3) 2_655
C19 H19 0.97(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 O4 0.88 1.76 2.6015(15) 161.8 7_554
O4 H4 O1 1.01 1.59 2.6015(15) 174.9 7_554
O5 H5 Cl1 0.75(2) 2.33(2) 3.0723(16) 170(2) 5_656
N16 H16 Cl1 0.87(4) 2.16(4) 3.037(2) 180.0 .
