#------------------------------------------------------------------------------
#$Date: 2019-11-22 19:01:01 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231256 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/63/4516330.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_4516330
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         'C7 H6 O3, C5 H6 N, Cl'
_chemical_formula_sum            'C12 H12 Cl N O3'
_chemical_formula_weight         253.68
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.3740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4053(3)
_cell_length_b                   6.7701(2)
_cell_length_c                   14.9514(3)
_cell_measurement_temperature    228(2)
_cell_volume                     1204.77(5)
_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 0.995
_diffrn_measured_fraction_theta_max 0.979
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10334
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         68.06
_diffrn_reflns_theta_min         4.10
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  0.7487
_exptl_absorpt_correction_T_min  0.4502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2148
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0297
_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)+(0.0475P)²+0.2858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                1928
_reflns_number_total             2148
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00628_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4516330
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl01 Cl 0.34553(3) 0.61909(5) 0.29119(2) 0.03324(14) Uani 1 1 d .
O002 O 0.56625(10) 0.46785(17) 0.25995(8) 0.0407(3) Uani 1 1 d D
O003 O 0.42445(9) -0.34750(16) 0.05280(8) 0.0390(3) Uani 1 1 d .
O004 O 0.60153(10) -0.32614(17) 0.04748(9) 0.0429(3) Uani 1 1 d .
N005 N 0.19939(11) 0.5449(2) 0.09024(10) 0.0401(3) Uani 1 1 d .
C006 C 0.55175(12) 0.2912(2) 0.21453(10) 0.0304(3) Uani 1 1 d .
C007 C 0.53116(12) -0.0702(2) 0.12244(10) 0.0280(3) Uani 1 1 d .
C008 C 0.63103(13) 0.0365(3) 0.14186(11) 0.0353(4) Uani 1 1 d .
C009 C 0.51871(12) -0.2589(2) 0.07156(10) 0.0308(3) Uani 1 1 d .
C010 C 0.45230(12) 0.1851(2) 0.19720(10) 0.0295(3) Uani 1 1 d .
C011 C 0.44230(13) 0.0063(2) 0.15122(10) 0.0300(3) Uani 1 1 d .
C012 C 0.64151(14) 0.2156(3) 0.18735(12) 0.0376(4) Uani 1 1 d .
C013 C 0.14338(16) 0.4185(3) -0.06025(12) 0.0446(4) Uani 1 1 d .
C014 C 0.15432(15) 0.7190(3) 0.06207(13) 0.0467(4) Uani 1 1 d .
C015 C 0.19597(15) 0.3952(3) 0.03237(12) 0.0419(4) Uani 1 1 d .
C016 C 0.09476(17) 0.5958(3) -0.09211(13) 0.0520(5) Uani 1 1 d .
C017 C 0.10031(18) 0.7482(3) -0.02993(15) 0.0567(5) Uani 1 1 d .
H003 H 0.4195 -0.4679 0.0172 0.074(14) Uiso 0.50 1 d PR
H004 H 0.5964 -0.4437 0.0167 0.100(19) Uiso 0.50 1 d PR
H010 H 0.3924(15) 0.234(3) 0.2182(13) 0.040(5) Uiso 1 1 d .
H011 H 0.3749(15) -0.069(3) 0.1411(13) 0.038(5) Uiso 1 1 d .
H008 H 0.6926(17) -0.012(3) 0.1229(13) 0.049(5) Uiso 1 1 d .
H012 H 0.7082(17) 0.288(3) 0.2013(13) 0.049(5) Uiso 1 1 d .
H014 H 0.1626(18) 0.811(3) 0.1084(16) 0.060(6) Uiso 1 1 d .
H002 H 0.5044(14) 0.501(3) 0.2664(14) 0.055(6) Uiso 1 1 d D
H005 H 0.2366(19) 0.542(3) 0.1496(16) 0.059(6) Uiso 1 1 d .
H013 H 0.1409(18) 0.309(3) -0.1005(16) 0.064(6) Uiso 1 1 d .
H015 H 0.2300(19) 0.275(4) 0.0598(16) 0.065(6) Uiso 1 1 d .
H016 H 0.056(2) 0.614(3) -0.1568(17) 0.070(7) Uiso 1 1 d .
H017 H 0.067(2) 0.868(3) -0.0500(17) 0.074(7) 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 0.0181 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
C006 O002 H002 107.2(15)
C009 O003 H003 115.5
C009 O004 H004 120.7
C014 N005 C015 122.75(15)
C014 N005 H005 113.2(15)
C015 N005 H005 123.8(15)
O002 C006 C012 117.80(14)
O002 C006 C010 122.22(14)
C012 C006 C010 119.96(14)
C011 C007 C008 118.60(14)
C011 C007 C009 120.37(13)
C008 C007 C009 121.03(13)
C012 C008 C007 120.93(15)
C012 C008 H008 118.7(12)
C007 C008 H008 120.3(12)
O004 C009 O003 122.45(14)
O004 C009 C007 118.94(13)
O003 C009 C007 118.61(13)
C011 C010 C006 119.83(14)
C011 C010 H010 120.4(11)
C006 C010 H010 119.7(11)
C010 C011 C007 120.82(14)
C010 C011 H011 120.0(11)
C007 C011 H011 119.1(11)
C008 C012 C006 119.85(15)
C008 C012 H012 121.7(12)
C006 C012 H012 118.4(12)
C015 C013 C016 119.55(17)
C015 C013 H013 118.2(14)
C016 C013 H013 122.2(13)
N005 C014 C017 119.60(18)
N005 C014 H014 114.8(14)
C017 C014 H014 125.6(14)
N005 C015 C013 119.53(17)
N005 C015 H015 116.3(14)
C013 C015 H015 124.2(14)
C013 C016 C017 119.27(17)
C013 C016 H016 120.7(13)
C017 C016 H016 120.0(13)
C014 C017 C016 119.29(19)
C014 C017 H017 120.2(16)
C016 C017 H017 120.5(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O002 C006 1.3619(19)
O002 H002 0.830(15)
O003 C009 1.2732(19)
O003 H003 0.9665
O004 C009 1.2655(18)
O004 H004 0.9131
N005 C014 1.322(3)
N005 C015 1.325(2)
N005 H005 0.88(2)
C006 C012 1.386(2)
C006 C010 1.387(2)
C007 C011 1.391(2)
C007 C008 1.392(2)
C007 C009 1.473(2)
C008 C012 1.378(2)
C008 H008 0.94(2)
C010 C011 1.381(2)
C010 H010 0.945(19)
C011 H011 0.955(18)
C012 H012 0.93(2)
C013 C015 1.363(3)
C013 C016 1.367(3)
C013 H013 0.95(2)
C014 C017 1.364(3)
C014 H014 0.92(2)
C015 H015 0.95(2)
C016 C017 1.377(3)
C016 H016 0.96(2)
C017 H017 0.92(2)
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
O002 H002 Cl01 0.830(15) 2.253(16) 3.0797(13) 174(2) .
O003 H003 O004 0.97 1.67 2.6384(15) 174.9 3_645
O004 H004 O003 0.91 1.73 2.6384(15) 173.2 3_645
N005 H005 Cl01 0.88(2) 2.23(2) 3.0814(14) 164(2) .
