# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB160K
_database_code_depnum_ccdc_archive 'CCDC 953962'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.126(2)
_cell_length_b                   10.606(1)
_cell_length_c                   25.328(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2451.5(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    9798
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      32.94

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12929
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.870
_diffrn_reflns_theta_max         31.099
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2439
_reflns_number_gt                2398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0603P)²+0.5351P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.235(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2439
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25395(9) 0.29477(7) 0.75058(3) 0.0315(2) Uani 1 1 d . . . . .
H1_1 H 0.1927(19) 0.3395(16) 0.7279(7) 0.059(5) Uiso 1 1 d . . . . .
C2_1 C 0.33290(11) 0.37202(9) 0.78196(4) 0.0256(3) Uani 1 1 d . . . . .
C3_1 C 0.43637(12) 0.31664(10) 0.81529(4) 0.0295(3) Uani 1 1 d . . . . .
H3_1 H 0.4487 0.2277 0.8153 0.035 Uiso 1 1 calc R U . . .
C4_1 C 0.52070(12) 0.39042(10) 0.84815(4) 0.0302(3) Uani 1 1 d . . . . .
H4_1 H 0.5913 0.3526 0.8707 0.036 Uiso 1 1 calc R U . . .
C5_1 C 0.50194(11) 0.52111(10) 0.84814(4) 0.0275(3) Uani 1 1 d . . . . .
C6_1 C 0.39905(12) 0.57669(10) 0.81461(4) 0.0286(3) Uani 1 1 d . . . . .
H6_1 H 0.3871 0.6657 0.8145 0.034 Uiso 1 1 calc R U . . .
C7_1 C 0.31464(11) 0.50278(10) 0.78168(4) 0.0270(3) Uani 1 1 d . . . . .
H7_1 H 0.2445 0.5406 0.7589 0.032 Uiso 1 1 calc R U . . .
C8_1 C 0.58475(12) 0.60009(10) 0.88304(4) 0.0318(3) Uani 1 1 d . . . . .
N9_1 N 0.64758(11) 0.66652(10) 0.91077(4) 0.0402(3) Uani 1 1 d . . . . .
O1_2 O 0.29089(9) 0.64023(8) 1.03356(3) 0.0363(2) Uani 1 1 d . . . . .
H1_2 H 0.2392(19) 0.7028(18) 1.0480(7) 0.059(5) Uiso 1 1 d . . . . .
C2_2 C 0.21552(11) 0.59407(9) 0.99176(4) 0.0261(3) Uani 1 1 d . . . . .
C3_2 C 0.27308(12) 0.48939(11) 0.96583(4) 0.0315(3) Uani 1 1 d . . . . .
H3_2 H 0.3622 0.4527 0.9777 0.038 Uiso 1 1 calc R U . . .
C4_2 C 0.20070(11) 0.43887(10) 0.92287(4) 0.0309(3) Uani 1 1 d . . . . .
H4_2 H 0.2395 0.3672 0.9053 0.037 Uiso 1 1 calc R U . . .
C5_2 C 0.07029(11) 0.49356(9) 0.90541(4) 0.0268(3) Uani 1 1 d . . . . .
C6_2 C 0.01261(11) 0.59747(10) 0.93180(4) 0.0284(3) Uani 1 1 d . . . . .
H6_2 H -0.0767 0.6340 0.9201 0.034 Uiso 1 1 calc R U . . .
C7_2 C 0.08423(11) 0.64758(9) 0.97484(4) 0.0276(3) Uani 1 1 d . . . . .
H7_2 H 0.0443 0.7182 0.9929 0.033 Uiso 1 1 calc R U . . .
C8_2 C -0.00425(12) 0.44536(10) 0.85968(4) 0.0320(3) Uani 1 1 d . . . . .
N9_2 N -0.06470(12) 0.40987(10) 0.82302(4) 0.0421(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3498(12) . ?
O1_1 H1_1 0.931(18) . ?
C2_1 C3_1 1.3962(14) . ?
C2_1 C7_1 1.3969(15) . ?
C3_1 C4_1 1.3775(15) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.3966(15) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3965(14) . ?
C5_1 C8_1 1.4332(15) . ?
C6_1 C7_1 1.3798(15) . ?
C6_1 H6_1 0.9500 . ?
C7_1 H7_1 0.9500 . ?
C8_1 N9_1 1.1483(15) . ?
O1_2 C2_2 1.3541(12) . ?
O1_2 H1_2 0.893(19) . ?
C2_2 C3_2 1.3927(14) . ?
C2_2 C7_2 1.3933(14) . ?
C3_2 C4_2 1.3810(15) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3959(15) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3923(15) . ?
C5_2 C8_2 1.4372(14) . ?
C6_2 C7_2 1.3777(14) . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7_2 0.9500 . ?
C8_2 N9_2 1.1438(15) . ?

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
C2_1 O1_1 H1_1 112.0(11) . . ?
O1_1 C2_1 C3_1 117.49(9) . . ?
O1_1 C2_1 C7_1 122.41(9) . . ?
C3_1 C2_1 C7_1 120.10(9) . . ?
C4_1 C3_1 C2_1 120.28(9) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.68(9) . . ?
C3_1 C4_1 H4_1 120.2 . . ?
C5_1 C4_1 H4_1 120.2 . . ?
C6_1 C5_1 C4_1 120.10(9) . . ?
C6_1 C5_1 C8_1 118.87(9) . . ?
C4_1 C5_1 C8_1 121.01(9) . . ?
C7_1 C6_1 C5_1 120.21(9) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.63(9) . . ?
C6_1 C7_1 H7_1 120.2 . . ?
C2_1 C7_1 H7_1 120.2 . . ?
N9_1 C8_1 C5_1 177.67(11) . . ?
C2_2 O1_2 H1_2 108.7(11) . . ?
O1_2 C2_2 C3_2 117.73(9) . . ?
O1_2 C2_2 C7_2 122.00(9) . . ?
C3_2 C2_2 C7_2 120.27(9) . . ?
C4_2 C3_2 C2_2 120.03(9) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.75(9) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.94(9) . . ?
C6_2 C5_2 C8_2 119.31(9) . . ?
C4_2 C5_2 C8_2 120.74(9) . . ?
C7_2 C6_2 C5_2 120.39(9) . . ?
C7_2 C6_2 H6_2 119.8 . . ?
C5_2 C6_2 H6_2 119.8 . . ?
C6_2 C7_2 C2_2 119.61(9) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.36(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.81(9) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.18(15) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.20(16) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.55(15) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.05(10) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.53(16) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.10(9) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.15(16) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.82(9) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.21(15) . . . . ?
O1_2 C2_2 C3_2 C4_2 -179.81(9) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.59(16) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.37(17) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.97(16) . . . . ?
C3_2 C4_2 C5_2 C8_2 177.81(10) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.62(15) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.18(9) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.33(15) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.47(9) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.94(15) . . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB200K
_database_code_depnum_ccdc_archive 'CCDC 954031'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.147(2)
_cell_length_b                   10.640(1)
_cell_length_c                   25.365(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2468.6(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9588
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      33.04

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12913
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.867
_diffrn_reflns_theta_max         31.086
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2442
_reflns_number_gt                2401
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0622P)²+0.4497P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.366(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2442
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25388(9) 0.29794(7) 0.75070(3) 0.0401(3) Uani 1 1 d . . . . .
H1_1 H 0.1942(19) 0.3441(17) 0.7293(7) 0.066(5) Uiso 1 1 d . . . . .
C2_1 C 0.33253(11) 0.37494(10) 0.78203(4) 0.0323(3) Uani 1 1 d . . . . .
C3_1 C 0.43549(12) 0.31974(10) 0.81535(4) 0.0371(3) Uani 1 1 d . . . . .
H3_1 H 0.4476 0.2311 0.8154 0.045 Uiso 1 1 calc R U . . .
C4_1 C 0.51959(12) 0.39319(11) 0.84815(4) 0.0380(3) Uani 1 1 d . . . . .
H4_1 H 0.5898 0.3554 0.8708 0.046 Uiso 1 1 calc R U . . .
C5_1 C 0.50131(11) 0.52322(10) 0.84804(4) 0.0346(3) Uani 1 1 d . . . . .
C6_1 C 0.39912(12) 0.57857(10) 0.81453(4) 0.0360(3) Uani 1 1 d . . . . .
H6_1 H 0.3875 0.6673 0.8143 0.043 Uiso 1 1 calc R U . . .
C7_1 C 0.31480(12) 0.50507(10) 0.78165(4) 0.0337(3) Uani 1 1 d . . . . .
H7_1 H 0.2451 0.5429 0.7589 0.040 Uiso 1 1 calc R U . . .
C8_1 C 0.58429(13) 0.60197(11) 0.88284(4) 0.0401(3) Uani 1 1 d . . . . .
N9_1 N 0.64724(13) 0.66770(10) 0.91051(4) 0.0513(3) Uani 1 1 d . . . . .
O1_2 O 0.28975(9) 0.63975(9) 1.03355(3) 0.0460(3) Uani 1 1 d . . . . .
H1_2 H 0.240(2) 0.7041(19) 1.0465(7) 0.069(5) Uiso 1 1 d . . . . .
C2_2 C 0.21445(11) 0.59435(10) 0.99169(4) 0.0331(3) Uani 1 1 d . . . . .
C3_2 C 0.27125(12) 0.49029(11) 0.96573(4) 0.0399(3) Uani 1 1 d . . . . .
H3_2 H 0.3599 0.4534 0.9776 0.048 Uiso 1 1 calc R U . . .
C4_2 C 0.19915(12) 0.44046(11) 0.92275(4) 0.0390(3) Uani 1 1 d . . . . .
H4_2 H 0.2377 0.3690 0.9051 0.047 Uiso 1 1 calc R U . . .
C5_2 C 0.06972(12) 0.49539(10) 0.90532(4) 0.0337(3) Uani 1 1 d . . . . .
C6_2 C 0.01267(11) 0.59896(10) 0.93177(4) 0.0360(3) Uani 1 1 d . . . . .
H6_2 H -0.0761 0.6358 0.9200 0.043 Uiso 1 1 calc R U . . .
C7_2 C 0.08403(12) 0.64829(10) 0.97478(4) 0.0349(3) Uani 1 1 d . . . . .
H7_2 H 0.0445 0.7188 0.9928 0.042 Uiso 1 1 calc R U . . .
C8_2 C -0.00494(12) 0.44770(11) 0.85970(5) 0.0403(3) Uani 1 1 d . . . . .
N9_2 N -0.06539(13) 0.41251(12) 0.82311(4) 0.0536(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3492(13) . ?
O1_1 H1_1 0.913(19) . ?
C2_1 C7_1 1.3941(15) . ?
C2_1 C3_1 1.3952(14) . ?
C3_1 C4_1 1.3765(16) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.3936(16) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3939(15) . ?
C5_1 C8_1 1.4343(15) . ?
C6_1 C7_1 1.3791(15) . ?
C6_1 H6_1 0.9500 . ?
C7_1 H7_1 0.9500 . ?
C8_1 N9_1 1.1460(15) . ?
O1_2 C2_2 1.3548(13) . ?
O1_2 H1_2 0.89(2) . ?
C2_2 C3_2 1.3890(15) . ?
C2_2 C7_2 1.3915(15) . ?
C3_2 C4_2 1.3801(15) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3923(16) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3918(16) . ?
C5_2 C8_2 1.4362(15) . ?
C6_2 C7_2 1.3754(15) . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7_2 0.9500 . ?
C8_2 N9_2 1.1434(16) . ?

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
C2_1 O1_1 H1_1 110.0(11) . . ?
O1_1 C2_1 C7_1 122.48(9) . . ?
O1_1 C2_1 C3_1 117.46(9) . . ?
C7_1 C2_1 C3_1 120.06(9) . . ?
C4_1 C3_1 C2_1 120.29(10) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.70(10) . . ?
C3_1 C4_1 H4_1 120.2 . . ?
C5_1 C4_1 H4_1 120.2 . . ?
C4_1 C5_1 C6_1 120.07(10) . . ?
C4_1 C5_1 C8_1 121.01(10) . . ?
C6_1 C5_1 C8_1 118.91(10) . . ?
C7_1 C6_1 C5_1 120.28(10) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.60(9) . . ?
C6_1 C7_1 H7_1 120.2 . . ?
C2_1 C7_1 H7_1 120.2 . . ?
N9_1 C8_1 C5_1 177.85(12) . . ?
C2_2 O1_2 H1_2 107.8(12) . . ?
O1_2 C2_2 C3_2 117.75(10) . . ?
O1_2 C2_2 C7_2 122.03(10) . . ?
C3_2 C2_2 C7_2 120.22(9) . . ?
C4_2 C3_2 C2_2 120.13(10) . . ?
C4_2 C3_2 H3_2 119.9 . . ?
C2_2 C3_2 H3_2 119.9 . . ?
C3_2 C4_2 C5_2 119.73(10) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.87(10) . . ?
C6_2 C5_2 C8_2 119.34(10) . . ?
C4_2 C5_2 C8_2 120.79(10) . . ?
C7_2 C6_2 C5_2 120.44(10) . . ?
C7_2 C6_2 H6_2 119.8 . . ?
C5_2 C6_2 H6_2 119.8 . . ?
C6_2 C7_2 C2_2 119.60(10) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.41(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.77(10) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.27(16) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.13(17) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.52(16) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.19(11) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.53(17) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.21(10) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.13(17) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.74(10) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.27(16) . . . . ?
O1_2 C2_2 C3_2 C4_2 -179.82(10) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.52(17) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.39(18) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.96(17) . . . . ?
C3_2 C4_2 C5_2 C8_2 178.05(11) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.62(16) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.40(10) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.29(16) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.49(10) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.86(16) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB220K
_database_code_depnum_ccdc_archive 'CCDC 954032'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.158(2)
_cell_length_b                   10.658(1)
_cell_length_c                   25.383(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2477.5(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    9352
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      32.87

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13354
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         31.095
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2458
_reflns_number_gt                2382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0637P)²+0.3546P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.415(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2458
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25377(9) 0.29965(7) 0.75079(3) 0.0446(3) Uani 1 1 d . . . . .
H1_1 H 0.1943(19) 0.3453(16) 0.7282(7) 0.068(5) Uiso 1 1 d . . . . .
C2_1 C 0.33242(11) 0.37649(10) 0.78207(4) 0.0358(3) Uani 1 1 d . . . . .
C3_1 C 0.43515(13) 0.32139(10) 0.81541(4) 0.0415(3) Uani 1 1 d . . . . .
H3_1 H 0.4470 0.2338 0.8155 0.050 Uiso 1 1 calc R U . . .
C4_1 C 0.51906(12) 0.39468(11) 0.84809(4) 0.0423(3) Uani 1 1 d . . . . .
H4_1 H 0.5884 0.3574 0.8704 0.051 Uiso 1 1 calc R U . . .
C5_1 C 0.50092(11) 0.52436(10) 0.84797(4) 0.0380(3) Uani 1 1 d . . . . .
C6_1 C 0.39900(12) 0.57978(10) 0.81445(4) 0.0398(3) Uani 1 1 d . . . . .
H6_1 H 0.3876 0.6674 0.8142 0.048 Uiso 1 1 calc R U . . .
C7_1 C 0.31490(12) 0.50628(10) 0.78167(4) 0.0378(3) Uani 1 1 d . . . . .
H7_1 H 0.2460 0.5436 0.7591 0.045 Uiso 1 1 calc R U . . .
C8_1 C 0.58394(13) 0.60280(11) 0.88271(4) 0.0446(3) Uani 1 1 d . . . . .
N9_1 N 0.64693(13) 0.66838(11) 0.91035(4) 0.0571(3) Uani 1 1 d . . . . .
O1_2 O 0.28910(10) 0.63943(9) 1.03357(3) 0.0512(3) Uani 1 1 d . . . . .
H1_2 H 0.2403(19) 0.7023(18) 1.0470(7) 0.068(5) Uiso 1 1 d . . . . .
C2_2 C 0.21403(11) 0.59447(10) 0.99164(4) 0.0368(3) Uani 1 1 d . . . . .
C3_2 C 0.27051(13) 0.49080(11) 0.96567(4) 0.0442(3) Uani 1 1 d . . . . .
H3_2 H 0.3582 0.4542 0.9773 0.053 Uiso 1 1 calc R U . . .
C4_2 C 0.19817(13) 0.44124(11) 0.92274(4) 0.0436(3) Uani 1 1 d . . . . .
H4_2 H 0.2359 0.3705 0.9053 0.052 Uiso 1 1 calc R U . . .
C5_2 C 0.06927(12) 0.49633(10) 0.90528(4) 0.0372(3) Uani 1 1 d . . . . .
C6_2 C 0.01264(11) 0.59972(10) 0.93173(4) 0.0400(3) Uani 1 1 d . . . . .
H6_2 H -0.0750 0.6364 0.9201 0.048 Uiso 1 1 calc R U . . .
C7_2 C 0.08404(12) 0.64861(10) 0.97477(4) 0.0388(3) Uani 1 1 d . . . . .
H7_2 H 0.0452 0.7182 0.9927 0.047 Uiso 1 1 calc R U . . .
C8_2 C -0.00535(12) 0.44894(11) 0.85968(5) 0.0447(3) Uani 1 1 d . . . . .
N9_2 N -0.06569(14) 0.41406(12) 0.82319(4) 0.0596(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3491(13) . ?
O1_1 H1_1 0.928(18) . ?
C2_1 C7_1 1.3926(15) . ?
C2_1 C3_1 1.3951(14) . ?
C3_1 C4_1 1.3744(16) . ?
C3_1 H3_1 0.9400 . ?
C4_1 C5_1 1.3920(16) . ?
C4_1 H4_1 0.9400 . ?
C5_1 C6_1 1.3943(15) . ?
C5_1 C8_1 1.4336(15) . ?
C6_1 C7_1 1.3781(15) . ?
C6_1 H6_1 0.9400 . ?
C7_1 H7_1 0.9400 . ?
C8_1 N9_1 1.1459(16) . ?
O1_2 C2_2 1.3546(12) . ?
O1_2 H1_2 0.875(19) . ?
C2_2 C3_2 1.3868(15) . ?
C2_2 C7_2 1.3905(15) . ?
C3_2 C4_2 1.3803(16) . ?
C3_2 H3_2 0.9400 . ?
C4_2 C5_2 1.3910(16) . ?
C4_2 H4_2 0.9400 . ?
C5_2 C6_2 1.3906(16) . ?
C5_2 C8_2 1.4360(15) . ?
C6_2 C7_2 1.3758(15) . ?
C6_2 H6_2 0.9400 . ?
C7_2 H7_2 0.9400 . ?
C8_2 N9_2 1.1408(16) . ?

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
C2_1 O1_1 H1_1 111.0(10) . . ?
O1_1 C2_1 C7_1 122.50(9) . . ?
O1_1 C2_1 C3_1 117.49(10) . . ?
C7_1 C2_1 C3_1 120.02(10) . . ?
C4_1 C3_1 C2_1 120.27(10) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.75(9) . . ?
C3_1 C4_1 H4_1 120.1 . . ?
C5_1 C4_1 H4_1 120.1 . . ?
C4_1 C5_1 C6_1 120.13(10) . . ?
C4_1 C5_1 C8_1 120.95(9) . . ?
C6_1 C5_1 C8_1 118.91(10) . . ?
C7_1 C6_1 C5_1 120.12(10) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.73(9) . . ?
C6_1 C7_1 H7_1 120.1 . . ?
C2_1 C7_1 H7_1 120.1 . . ?
N9_1 C8_1 C5_1 177.82(12) . . ?
C2_2 O1_2 H1_2 108.5(11) . . ?
O1_2 C2_2 C3_2 117.78(10) . . ?
O1_2 C2_2 C7_2 121.98(10) . . ?
C3_2 C2_2 C7_2 120.24(9) . . ?
C4_2 C3_2 C2_2 120.08(10) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.82(10) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.82(10) . . ?
C6_2 C5_2 C8_2 119.37(10) . . ?
C4_2 C5_2 C8_2 120.81(10) . . ?
C7_2 C6_2 C5_2 120.41(10) . . ?
C7_2 C6_2 H6_2 119.8 . . ?
C5_2 C6_2 H6_2 119.8 . . ?
C6_2 C7_2 C2_2 119.63(10) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.41(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.77(10) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.23(16) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.20(17) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.61(16) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.20(11) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.60(17) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.23(10) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.17(17) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.76(10) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.24(16) . . . . ?
O1_2 C2_2 C3_2 C4_2 179.94(10) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.32(18) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.65(18) . . . . ?
C3_2 C4_2 C5_2 C6_2 -1.11(17) . . . . ?
C3_2 C4_2 C5_2 C8_2 177.95(11) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.61(17) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.46(10) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.35(16) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.58(10) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.82(17) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.040

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB140K
_database_code_depnum_ccdc_archive 'CCDC 954030'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.116(2)
_cell_length_b                   10.590(1)
_cell_length_c                   25.311(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2443.5(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    10030
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      32.94

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12853
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.871
_diffrn_reflns_theta_max         31.093
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2433
_reflns_number_gt                2400
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0567P)²+0.6081P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.202(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2433
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25406(9) 0.29331(7) 0.75053(3) 0.0278(2) Uani 1 1 d . . . . .
H1_1 H 0.1926(19) 0.3385(16) 0.7283(7) 0.050(4) Uiso 1 1 d . . . . .
C2_1 C 0.33300(11) 0.37071(10) 0.78195(4) 0.0227(3) Uani 1 1 d . . . . .
C3_1 C 0.43670(12) 0.31514(10) 0.81525(4) 0.0263(3) Uani 1 1 d . . . . .
H3_1 H 0.4491 0.2261 0.8152 0.032 Uiso 1 1 calc R U . . .
C4_1 C 0.52124(12) 0.38918(10) 0.84819(4) 0.0268(3) Uani 1 1 d . . . . .
H4_1 H 0.5920 0.3514 0.8708 0.032 Uiso 1 1 calc R U . . .
C5_1 C 0.50227(11) 0.52004(10) 0.84817(4) 0.0244(3) Uani 1 1 d . . . . .
C6_1 C 0.39912(12) 0.57570(10) 0.81467(4) 0.0254(3) Uani 1 1 d . . . . .
H6_1 H 0.3871 0.6648 0.8146 0.030 Uiso 1 1 calc R U . . .
C7_1 C 0.31468(11) 0.50178(10) 0.78170(4) 0.0239(3) Uani 1 1 d . . . . .
H7_1 H 0.2445 0.5397 0.7590 0.029 Uiso 1 1 calc R U . . .
C8_1 C 0.58522(12) 0.59929(10) 0.88310(4) 0.0280(3) Uani 1 1 d . . . . .
N9_1 N 0.64775(11) 0.66589(10) 0.91089(4) 0.0354(3) Uani 1 1 d . . . . .
O1_2 O 0.29147(9) 0.64046(8) 1.03354(3) 0.0320(2) Uani 1 1 d . . . . .
H1_2 H 0.240(2) 0.7031(18) 1.0475(7) 0.055(5) Uiso 1 1 d . . . . .
C2_2 C 0.21601(11) 0.59383(10) 0.99177(4) 0.0234(3) Uani 1 1 d . . . . .
C3_2 C 0.27385(12) 0.48912(11) 0.96587(4) 0.0278(3) Uani 1 1 d . . . . .
H3_2 H 0.3632 0.4527 0.9777 0.033 Uiso 1 1 calc R U . . .
C4_2 C 0.20140(12) 0.43809(10) 0.92294(4) 0.0273(3) Uani 1 1 d . . . . .
H4_2 H 0.2403 0.3662 0.9054 0.033 Uiso 1 1 calc R U . . .
C5_2 C 0.07069(11) 0.49268(10) 0.90542(4) 0.0237(3) Uani 1 1 d . . . . .
C6_2 C 0.01254(11) 0.59683(10) 0.93180(4) 0.0253(3) Uani 1 1 d . . . . .
H6_2 H -0.0770 0.6332 0.9201 0.030 Uiso 1 1 calc R U . . .
C7_2 C 0.08442(11) 0.64721(9) 0.97484(4) 0.0246(3) Uani 1 1 d . . . . .
H7_2 H 0.0445 0.7180 0.9929 0.030 Uiso 1 1 calc R U . . .
C8_2 C -0.00395(12) 0.44421(10) 0.85968(4) 0.0282(3) Uani 1 1 d . . . . .
N9_2 N -0.06450(12) 0.40865(10) 0.82296(4) 0.0374(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3499(12) . ?
O1_1 H1_1 0.927(18) . ?
C2_1 C3_1 1.3966(14) . ?
C2_1 C7_1 1.3980(14) . ?
C3_1 C4_1 1.3799(15) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.3965(15) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3966(14) . ?
C5_1 C8_1 1.4346(15) . ?
C6_1 C7_1 1.3790(15) . ?
C6_1 H6_1 0.9500 . ?
C7_1 H7_1 0.9500 . ?
C8_1 N9_1 1.1477(15) . ?
O1_2 C2_2 1.3545(12) . ?
O1_2 H1_2 0.89(2) . ?
C2_2 C3_2 1.3919(15) . ?
C2_2 C7_2 1.3936(15) . ?
C3_2 C4_2 1.3816(15) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3966(15) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3941(15) . ?
C5_2 C8_2 1.4377(15) . ?
C6_2 C7_2 1.3786(15) . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7_2 0.9500 . ?
C8_2 N9_2 1.1446(15) . ?

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
C2_1 O1_1 H1_1 111.5(10) . . ?
O1_1 C2_1 C3_1 117.42(9) . . ?
O1_1 C2_1 C7_1 122.45(9) . . ?
C3_1 C2_1 C7_1 120.13(9) . . ?
C4_1 C3_1 C2_1 120.22(10) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.63(9) . . ?
C3_1 C4_1 H4_1 120.2 . . ?
C5_1 C4_1 H4_1 120.2 . . ?
C4_1 C5_1 C6_1 120.17(9) . . ?
C4_1 C5_1 C8_1 121.00(9) . . ?
C6_1 C5_1 C8_1 118.82(10) . . ?
C7_1 C6_1 C5_1 120.24(9) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.62(9) . . ?
C6_1 C7_1 H7_1 120.2 . . ?
C2_1 C7_1 H7_1 120.2 . . ?
N9_1 C8_1 C5_1 177.57(11) . . ?
C2_2 O1_2 H1_2 108.4(11) . . ?
O1_2 C2_2 C3_2 117.75(9) . . ?
O1_2 C2_2 C7_2 121.95(9) . . ?
C3_2 C2_2 C7_2 120.29(9) . . ?
C4_2 C3_2 C2_2 120.06(10) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.71(10) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.99(9) . . ?
C6_2 C5_2 C8_2 119.22(10) . . ?
C4_2 C5_2 C8_2 120.78(10) . . ?
C7_2 C6_2 C5_2 120.25(10) . . ?
C7_2 C6_2 H6_2 119.9 . . ?
C5_2 C6_2 H6_2 119.9 . . ?
C6_2 C7_2 C2_2 119.68(9) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.28(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.77(9) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.22(16) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.18(16) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.52(15) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.07(10) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.46(16) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.16(10) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.06(16) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.81(9) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.28(15) . . . . ?
O1_2 C2_2 C3_2 C4_2 -179.81(10) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.45(16) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.54(17) . . . . ?
C3_2 C4_2 C5_2 C6_2 -1.12(16) . . . . ?
C3_2 C4_2 C5_2 C8_2 177.71(10) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.72(16) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.12(9) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.26(16) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.42(9) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.85(16) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB300K
_database_code_depnum_ccdc_archive 'CCDC 953966'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.203(2)
_cell_length_b                   10.737(1)
_cell_length_c                   25.458(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2515.6(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8379
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      33.02

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13515
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.391
_diffrn_reflns_theta_max         31.104
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2484
_reflns_number_gt                2387
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0722P)²+0.2770P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.481(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2484
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25330(11) 0.30642(8) 0.75109(3) 0.0653(3) Uani 1 1 d . . . . .
H1_1 H 0.1978(19) 0.3513(17) 0.7290(7) 0.090(5) Uiso 1 1 d . . . . .
C2_1 C 0.33180(12) 0.38270(10) 0.78224(4) 0.0516(3) Uani 1 1 d . . . . .
C3_1 C 0.43341(14) 0.32814(11) 0.81550(4) 0.0597(3) Uani 1 1 d . . . . .
H3_1 H 0.4448 0.2421 0.8157 0.072 Uiso 1 1 calc R U . . .
C4_1 C 0.51678(13) 0.40036(12) 0.84800(5) 0.0606(3) Uani 1 1 d . . . . .
H4_1 H 0.5846 0.3635 0.8702 0.073 Uiso 1 1 calc R U . . .
C5_1 C 0.49974(12) 0.52901(11) 0.84776(4) 0.0548(3) Uani 1 1 d . . . . .
C6_1 C 0.39881(13) 0.58364(11) 0.81422(4) 0.0571(3) Uani 1 1 d . . . . .
H6_1 H 0.3880 0.6698 0.8138 0.069 Uiso 1 1 calc R U . . .
C7_1 C 0.31511(13) 0.51122(11) 0.78175(4) 0.0543(3) Uani 1 1 d . . . . .
H7_1 H 0.2475 0.5480 0.7595 0.065 Uiso 1 1 calc R U . . .
C8_1 C 0.58290(14) 0.60651(12) 0.88242(5) 0.0645(4) Uani 1 1 d . . . . .
N9_1 N 0.64625(15) 0.67102(12) 0.90981(5) 0.0832(4) Uani 1 1 d . . . . .
O1_2 O 0.28660(11) 0.63858(10) 1.03361(4) 0.0740(3) Uani 1 1 d . . . . .
H1_2 H 0.238(2) 0.708(2) 1.0469(8) 0.102(6) Uiso 1 1 d . . . . .
C2_2 C 0.21192(12) 0.59521(10) 0.99149(4) 0.0532(3) Uani 1 1 d . . . . .
C3_2 C 0.26699(14) 0.49254(13) 0.96547(5) 0.0641(4) Uani 1 1 d . . . . .
H3_2 H 0.3528 0.4557 0.9769 0.077 Uiso 1 1 calc R U . . .
C4_2 C 0.19477(14) 0.44464(13) 0.92251(5) 0.0632(3) Uani 1 1 d . . . . .
H4_2 H 0.2312 0.3750 0.9052 0.076 Uiso 1 1 calc R U . . .
C5_2 C 0.06776(12) 0.50049(11) 0.90511(4) 0.0528(3) Uani 1 1 d . . . . .
C6_2 C 0.01290(12) 0.60288(11) 0.93153(5) 0.0576(3) Uani 1 1 d . . . . .
H6_2 H -0.0727 0.6400 0.9200 0.069 Uiso 1 1 calc R U . . .
C7_2 C 0.08379(12) 0.65017(10) 0.97459(5) 0.0562(3) Uani 1 1 d . . . . .
H7_2 H 0.0461 0.7187 0.9923 0.067 Uiso 1 1 calc R U . . .
C8_2 C -0.00675(14) 0.45422(12) 0.85962(5) 0.0643(4) Uani 1 1 d . . . . .
N9_2 N -0.06664(15) 0.41996(14) 0.82327(5) 0.0850(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3496(14) . ?
O1_1 H1_1 0.899(19) . ?
C2_1 C7_1 1.3885(16) . ?
C2_1 C3_1 1.3909(15) . ?
C3_1 C4_1 1.3692(17) . ?
C3_1 H3_1 0.9300 . ?
C4_1 C5_1 1.3902(18) . ?
C4_1 H4_1 0.9300 . ?
C5_1 C6_1 1.3915(15) . ?
C5_1 C8_1 1.4341(16) . ?
C6_1 C7_1 1.3716(16) . ?
C6_1 H6_1 0.9300 . ?
C7_1 H7_1 0.9300 . ?
C8_1 N9_1 1.1427(17) . ?
O1_2 C2_2 1.3562(13) . ?
O1_2 H1_2 0.93(2) . ?
C2_2 C3_2 1.3824(16) . ?
C2_2 C7_2 1.3870(16) . ?
C3_2 C4_2 1.3791(17) . ?
C3_2 H3_2 0.9300 . ?
C4_2 C5_2 1.3865(17) . ?
C4_2 H4_2 0.9300 . ?
C5_2 C6_2 1.3841(17) . ?
C5_2 C8_2 1.4346(16) . ?
C6_2 C7_2 1.3729(16) . ?
C6_2 H6_2 0.9300 . ?
C7_2 H7_2 0.9300 . ?
C8_2 N9_2 1.1383(17) . ?

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
C2_1 O1_1 H1_1 110.2(11) . . ?
O1_1 C2_1 C7_1 122.59(10) . . ?
O1_1 C2_1 C3_1 117.51(10) . . ?
C7_1 C2_1 C3_1 119.90(10) . . ?
C4_1 C3_1 C2_1 120.40(11) . . ?
C4_1 C3_1 H3_1 119.8 . . ?
C2_1 C3_1 H3_1 119.8 . . ?
C3_1 C4_1 C5_1 119.79(10) . . ?
C3_1 C4_1 H4_1 120.1 . . ?
C5_1 C4_1 H4_1 120.1 . . ?
C4_1 C5_1 C6_1 119.80(10) . . ?
C4_1 C5_1 C8_1 120.90(10) . . ?
C6_1 C5_1 C8_1 119.29(11) . . ?
C7_1 C6_1 C5_1 120.38(10) . . ?
C7_1 C6_1 H6_1 119.8 . . ?
C5_1 C6_1 H6_1 119.8 . . ?
C6_1 C7_1 C2_1 119.73(10) . . ?
C6_1 C7_1 H7_1 120.1 . . ?
C2_1 C7_1 H7_1 120.1 . . ?
N9_1 C8_1 C5_1 177.98(14) . . ?
C2_2 O1_2 H1_2 108.6(12) . . ?
O1_2 C2_2 C3_2 117.83(11) . . ?
O1_2 C2_2 C7_2 122.01(11) . . ?
C3_2 C2_2 C7_2 120.16(10) . . ?
C4_2 C3_2 C2_2 120.04(11) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.89(11) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.72(10) . . ?
C6_2 C5_2 C8_2 119.54(11) . . ?
C4_2 C5_2 C8_2 120.74(11) . . ?
C7_2 C6_2 C5_2 120.56(10) . . ?
C7_2 C6_2 H6_2 119.7 . . ?
C5_2 C6_2 H6_2 119.7 . . ?
C6_2 C7_2 C2_2 119.62(10) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.58(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.84(11) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.30(18) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.02(19) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.47(18) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.31(12) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.61(18) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.19(11) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.29(18) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.68(11) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.17(18) . . . . ?
O1_2 C2_2 C3_2 C4_2 179.78(12) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.16(19) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.7(2) . . . . ?
C3_2 C4_2 C5_2 C6_2 -1.06(19) . . . . ?
C3_2 C4_2 C5_2 C8_2 178.23(12) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.49(18) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.81(11) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.40(18) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.67(11) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.73(18) . . . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB120K
_database_code_depnum_ccdc_archive 'CCDC 954029'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.107(2)
_cell_length_b                   10.575(1)
_cell_length_c                   25.296(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2436.2(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9616
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      32.94

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12739
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         31.104
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2416
_reflns_number_gt                2388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0493P)²+0.6899P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.162(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2416
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25409(8) 0.29185(6) 0.75050(3) 0.0243(2) Uani 1 1 d . . . . .
H1_1 H 0.1931(17) 0.3369(16) 0.7288(6) 0.046(4) Uiso 1 1 d . . . . .
C2_1 C 0.33309(10) 0.36940(9) 0.78197(3) 0.0200(2) Uani 1 1 d . . . . .
C3_1 C 0.43705(11) 0.31371(9) 0.81526(4) 0.0232(2) Uani 1 1 d . . . . .
H3_1 H 0.4494 0.2245 0.8152 0.028 Uiso 1 1 calc R U . . .
C4_1 C 0.52174(11) 0.38787(10) 0.84818(4) 0.0235(2) Uani 1 1 d . . . . .
H4_1 H 0.5927 0.3500 0.8707 0.028 Uiso 1 1 calc R U . . .
C5_1 C 0.50263(11) 0.51912(10) 0.84821(4) 0.0214(2) Uani 1 1 d . . . . .
C6_1 C 0.39916(11) 0.57480(9) 0.81476(4) 0.0224(2) Uani 1 1 d . . . . .
H6_1 H 0.3869 0.6640 0.8147 0.027 Uiso 1 1 calc R U . . .
C7_1 C 0.31458(11) 0.50065(9) 0.78173(4) 0.0211(2) Uani 1 1 d . . . . .
H7_1 H 0.2442 0.5386 0.7590 0.025 Uiso 1 1 calc R U . . .
C8_1 C 0.58551(11) 0.59851(10) 0.88320(4) 0.0246(2) Uani 1 1 d . . . . .
N9_1 N 0.64795(10) 0.66543(9) 0.91098(4) 0.0307(2) Uani 1 1 d . . . . .
O1_2 O 0.29208(8) 0.64067(8) 1.03354(3) 0.0278(2) Uani 1 1 d . . . . .
H1_2 H 0.2413(19) 0.7026(17) 1.0487(7) 0.052(4) Uiso 1 1 d . . . . .
C2_2 C 0.21643(10) 0.59374(9) 0.99182(4) 0.0206(2) Uani 1 1 d . . . . .
C3_2 C 0.27457(11) 0.48859(10) 0.96595(4) 0.0243(2) Uani 1 1 d . . . . .
H3_2 H 0.3640 0.4522 0.9779 0.029 Uiso 1 1 calc R U . . .
C4_2 C 0.20213(11) 0.43734(10) 0.92297(4) 0.0239(2) Uani 1 1 d . . . . .
H4_2 H 0.2413 0.3655 0.9054 0.029 Uiso 1 1 calc R U . . .
C5_2 C 0.07096(11) 0.49173(9) 0.90547(4) 0.0209(2) Uani 1 1 d . . . . .
C6_2 C 0.01256(10) 0.59613(9) 0.93181(4) 0.0221(2) Uani 1 1 d . . . . .
H6_2 H -0.0771 0.6324 0.9201 0.027 Uiso 1 1 calc R U . . .
C7_2 C 0.08453(11) 0.64690(9) 0.97486(4) 0.0216(2) Uani 1 1 d . . . . .
H7_2 H 0.0444 0.7178 0.9929 0.026 Uiso 1 1 calc R U . . .
C8_2 C -0.00367(11) 0.44305(10) 0.85969(4) 0.0248(2) Uani 1 1 d . . . . .
N9_2 N -0.06416(11) 0.40731(10) 0.82290(4) 0.0323(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3505(12) . ?
O1_1 H1_1 0.915(17) . ?
C2_1 C3_1 1.3972(13) . ?
C2_1 C7_1 1.3983(14) . ?
C3_1 C4_1 1.3796(14) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.3989(14) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3967(14) . ?
C5_1 C8_1 1.4346(14) . ?
C6_1 C7_1 1.3807(14) . ?
C6_1 H6_1 0.9500 . ?
C7_1 H7_1 0.9500 . ?
C8_1 N9_1 1.1480(14) . ?
O1_2 C2_2 1.3546(12) . ?
O1_2 H1_2 0.888(19) . ?
C2_2 C7_2 1.3940(14) . ?
C2_2 C3_2 1.3946(14) . ?
C3_2 C4_2 1.3823(14) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3978(14) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3949(14) . ?
C5_2 C8_2 1.4379(14) . ?
C6_2 C7_2 1.3798(14) . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7_2 0.9500 . ?
C8_2 N9_2 1.1458(14) . ?

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
C2_1 O1_1 H1_1 111.2(10) . . ?
O1_1 C2_1 C3_1 117.41(9) . . ?
O1_1 C2_1 C7_1 122.41(9) . . ?
C3_1 C2_1 C7_1 120.18(9) . . ?
C4_1 C3_1 C2_1 120.20(9) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.66(9) . . ?
C3_1 C4_1 H4_1 120.2 . . ?
C5_1 C4_1 H4_1 120.2 . . ?
C6_1 C5_1 C4_1 120.13(9) . . ?
C6_1 C5_1 C8_1 118.82(9) . . ?
C4_1 C5_1 C8_1 121.03(9) . . ?
C7_1 C6_1 C5_1 120.24(9) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.60(9) . . ?
C6_1 C7_1 H7_1 120.2 . . ?
C2_1 C7_1 H7_1 120.2 . . ?
N9_1 C8_1 C5_1 177.47(11) . . ?
C2_2 O1_2 H1_2 109.9(11) . . ?
O1_2 C2_2 C7_2 122.02(9) . . ?
O1_2 C2_2 C3_2 117.69(9) . . ?
C7_2 C2_2 C3_2 120.29(9) . . ?
C4_2 C3_2 C2_2 120.03(9) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.72(9) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 120.01(9) . . ?
C6_2 C5_2 C8_2 119.20(9) . . ?
C4_2 C5_2 C8_2 120.78(9) . . ?
C7_2 C6_2 C5_2 120.26(9) . . ?
C7_2 C6_2 H6_2 119.9 . . ?
C5_2 C6_2 H6_2 119.9 . . ?
C6_2 C7_2 C2_2 119.68(9) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.27(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.69(9) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.16(15) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.24(15) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.52(14) . . . . ?
C3_1 C4_1 C5_1 C8_1 177.93(9) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.40(15) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.09(9) . . . . ?
C5_1 C6_1 C7_1 C2_1 0.01(15) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.79(9) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.29(14) . . . . ?
O1_2 C2_2 C3_2 C4_2 -179.68(9) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.62(15) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.31(16) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.94(15) . . . . ?
C3_2 C4_2 C5_2 C8_2 177.71(9) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.63(15) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.04(9) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.30(15) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.38(9) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.93(15) . . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB180K
_database_code_depnum_ccdc_archive 'CCDC 953963'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.136(2)
_cell_length_b                   10.622(1)
_cell_length_c                   25.346(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2459.6(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9369
_cell_measurement_theta_min      1.87
_cell_measurement_theta_max      32.93

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12381
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         31.102
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2422
_reflns_number_gt                2397
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0572P)²+0.5496P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.331(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2422
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25387(9) 0.29638(7) 0.75066(3) 0.0356(2) Uani 1 1 d . . . . .
H1_1 H 0.1918(19) 0.3412(17) 0.7286(7) 0.059(5) Uiso 1 1 d . . . . .
C2_1 C 0.33276(11) 0.37347(10) 0.78200(4) 0.0286(3) Uani 1 1 d . . . . .
C3_1 C 0.43590(12) 0.31812(10) 0.81529(4) 0.0332(3) Uani 1 1 d . . . . .
H3_1 H 0.4481 0.2293 0.8153 0.040 Uiso 1 1 calc R U . . .
C4_1 C 0.52012(13) 0.39175(11) 0.84813(4) 0.0340(3) Uani 1 1 d . . . . .
H4_1 H 0.5905 0.3539 0.8707 0.041 Uiso 1 1 calc R U . . .
C5_1 C 0.50167(12) 0.52213(10) 0.84810(4) 0.0306(3) Uani 1 1 d . . . . .
C6_1 C 0.39906(12) 0.57758(10) 0.81454(4) 0.0320(3) Uani 1 1 d . . . . .
H6_1 H 0.3873 0.6664 0.8143 0.038 Uiso 1 1 calc R U . . .
C7_1 C 0.31473(12) 0.50387(10) 0.78167(4) 0.0302(3) Uani 1 1 d . . . . .
H7_1 H 0.2447 0.5417 0.7589 0.036 Uiso 1 1 calc R U . . .
C8_1 C 0.58453(13) 0.60105(11) 0.88290(4) 0.0359(3) Uani 1 1 d . . . . .
N9_1 N 0.64744(12) 0.66708(10) 0.91064(4) 0.0453(3) Uani 1 1 d . . . . .
O1_2 O 0.29030(10) 0.64004(9) 1.03359(3) 0.0407(3) Uani 1 1 d . . . . .
H1_2 H 0.239(2) 0.7028(19) 1.0468(7) 0.063(5) Uiso 1 1 d . . . . .
C2_2 C 0.21492(11) 0.59416(10) 0.99169(4) 0.0295(3) Uani 1 1 d . . . . .
C3_2 C 0.27221(12) 0.48986(12) 0.96580(4) 0.0352(3) Uani 1 1 d . . . . .
H3_2 H 0.3611 0.4532 0.9777 0.042 Uiso 1 1 calc R U . . .
C4_2 C 0.19997(12) 0.43949(11) 0.92285(4) 0.0347(3) Uani 1 1 d . . . . .
H4_2 H 0.2386 0.3678 0.9053 0.042 Uiso 1 1 calc R U . . .
C5_2 C 0.07000(12) 0.49444(10) 0.90537(4) 0.0299(3) Uani 1 1 d . . . . .
C6_2 C 0.01260(12) 0.59818(10) 0.93176(4) 0.0320(3) Uani 1 1 d . . . . .
H6_2 H -0.0764 0.6349 0.9200 0.038 Uiso 1 1 calc R U . . .
C7_2 C 0.08421(12) 0.64790(10) 0.97480(4) 0.0311(3) Uani 1 1 d . . . . .
H7_2 H 0.0446 0.7185 0.9929 0.037 Uiso 1 1 calc R U . . .
C8_2 C -0.00451(13) 0.44653(11) 0.85970(5) 0.0357(3) Uani 1 1 d . . . . .
N9_2 N -0.06489(13) 0.41123(11) 0.82308(4) 0.0476(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3495(13) . ?
O1_1 H1_1 0.928(18) . ?
C2_1 C7_1 1.3949(16) . ?
C2_1 C3_1 1.3949(15) . ?
C3_1 C4_1 1.3771(16) . ?
C3_1 H3_1 0.9500 . ?
C4_1 C5_1 1.3952(16) . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.3961(15) . ?
C5_1 C8_1 1.4332(15) . ?
C6_1 C7_1 1.3785(16) . ?
C6_1 H6_1 0.9500 . ?
C7_1 H7_1 0.9500 . ?
C8_1 N9_1 1.1474(16) . ?
O1_2 C2_2 1.3563(13) . ?
O1_2 H1_2 0.88(2) . ?
C2_2 C3_2 1.3899(16) . ?
C2_2 C7_2 1.3911(15) . ?
C3_2 C4_2 1.3810(16) . ?
C3_2 H3_2 0.9500 . ?
C4_2 C5_2 1.3954(16) . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.3916(16) . ?
C5_2 C8_2 1.4360(15) . ?
C6_2 C7_2 1.3774(15) . ?
C6_2 H6_2 0.9500 . ?
C7_2 H7_2 0.9500 . ?
C8_2 N9_2 1.1429(16) . ?

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
C2_1 O1_1 H1_1 111.7(11) . . ?
O1_1 C2_1 C7_1 122.41(9) . . ?
O1_1 C2_1 C3_1 117.47(10) . . ?
C7_1 C2_1 C3_1 120.13(10) . . ?
C4_1 C3_1 C2_1 120.25(10) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.72(10) . . ?
C3_1 C4_1 H4_1 120.1 . . ?
C5_1 C4_1 H4_1 120.1 . . ?
C4_1 C5_1 C6_1 120.02(10) . . ?
C4_1 C5_1 C8_1 121.09(10) . . ?
C6_1 C5_1 C8_1 118.88(10) . . ?
C7_1 C6_1 C5_1 120.25(10) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.63(10) . . ?
C6_1 C7_1 H7_1 120.2 . . ?
C2_1 C7_1 H7_1 120.2 . . ?
N9_1 C8_1 C5_1 177.82(12) . . ?
C2_2 O1_2 H1_2 107.4(12) . . ?
O1_2 C2_2 C3_2 117.70(10) . . ?
O1_2 C2_2 C7_2 121.96(10) . . ?
C3_2 C2_2 C7_2 120.33(10) . . ?
C4_2 C3_2 C2_2 120.07(10) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.66(10) . . ?
C3_2 C4_2 H4_2 120.2 . . ?
C5_2 C4_2 H4_2 120.2 . . ?
C6_2 C5_2 C4_2 119.95(10) . . ?
C6_2 C5_2 C8_2 119.30(10) . . ?
C4_2 C5_2 C8_2 120.74(10) . . ?
C7_2 C6_2 C5_2 120.35(10) . . ?
C7_2 C6_2 H6_2 119.8 . . ?
C5_2 C6_2 H6_2 119.8 . . ?
C6_2 C7_2 C2_2 119.62(10) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.38(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.83(10) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.22(17) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.16(17) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.55(16) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.15(11) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.57(17) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.16(10) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.19(17) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.79(10) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.21(16) . . . . ?
O1_2 C2_2 C3_2 C4_2 -179.89(10) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.46(17) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.50(18) . . . . ?
C3_2 C4_2 C5_2 C6_2 -1.07(17) . . . . ?
C3_2 C4_2 C5_2 C8_2 177.84(10) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.67(17) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.25(10) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.30(16) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.50(10) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.87(17) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB260K
_database_code_depnum_ccdc_archive 'CCDC 953965'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.179(2)
_cell_length_b                   10.697(1)
_cell_length_c                   25.420(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2495.9(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    8762
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      32.96

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13384
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.863
_diffrn_reflns_theta_max         31.098
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2463
_reflns_number_gt                2386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0598P)²+0.3390P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.455(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2463
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25359(10) 0.30306(8) 0.75093(3) 0.0546(3) Uani 1 1 d . . . . .
H1_1 H 0.1943(19) 0.3487(16) 0.7289(7) 0.078(5) Uiso 1 1 d . . . . .
C2_1 C 0.33209(12) 0.37968(10) 0.78215(4) 0.0436(3) Uani 1 1 d . . . . .
C3_1 C 0.43430(13) 0.32462(10) 0.81547(4) 0.0502(3) Uani 1 1 d . . . . .
H3_1 H 0.4459 0.2383 0.8156 0.060 Uiso 1 1 calc R U . . .
C4_1 C 0.51784(13) 0.39754(11) 0.84805(4) 0.0510(3) Uani 1 1 d . . . . .
H4_1 H 0.5860 0.3607 0.8702 0.061 Uiso 1 1 calc R U . . .
C5_1 C 0.50040(11) 0.52664(11) 0.84788(4) 0.0461(3) Uani 1 1 d . . . . .
C6_1 C 0.39887(13) 0.58170(10) 0.81435(4) 0.0481(3) Uani 1 1 d . . . . .
H6_1 H 0.3877 0.6681 0.8140 0.058 Uiso 1 1 calc R U . . .
C7_1 C 0.31496(12) 0.50853(10) 0.78168(4) 0.0459(3) Uani 1 1 d . . . . .
H7_1 H 0.2471 0.5453 0.7594 0.055 Uiso 1 1 calc R U . . .
C8_1 C 0.58342(13) 0.60476(12) 0.88255(5) 0.0543(3) Uani 1 1 d . . . . .
N9_1 N 0.64654(14) 0.66973(11) 0.91010(5) 0.0698(4) Uani 1 1 d . . . . .
O1_2 O 0.28781(10) 0.63890(10) 1.03359(3) 0.0623(3) Uani 1 1 d . . . . .
H1_2 H 0.239(2) 0.7028(19) 1.0469(7) 0.082(5) Uiso 1 1 d . . . . .
C2_2 C 0.21299(11) 0.59485(10) 0.99152(4) 0.0450(3) Uani 1 1 d . . . . .
C3_2 C 0.26866(13) 0.49168(12) 0.96558(4) 0.0538(3) Uani 1 1 d . . . . .
H3_2 H 0.3549 0.4551 0.9771 0.065 Uiso 1 1 calc R U . . .
C4_2 C 0.19656(13) 0.44301(12) 0.92265(4) 0.0529(3) Uani 1 1 d . . . . .
H4_2 H 0.2336 0.3732 0.9054 0.064 Uiso 1 1 calc R U . . .
C5_2 C 0.06846(12) 0.49838(10) 0.90517(4) 0.0447(3) Uani 1 1 d . . . . .
C6_2 C 0.01258(12) 0.60123(11) 0.93163(5) 0.0486(3) Uani 1 1 d . . . . .
H6_2 H -0.0737 0.6378 0.9202 0.058 Uiso 1 1 calc R U . . .
C7_2 C 0.08382(12) 0.64940(10) 0.97469(4) 0.0474(3) Uani 1 1 d . . . . .
H7_2 H 0.0458 0.7181 0.9924 0.057 Uiso 1 1 calc R U . . .
C8_2 C -0.00604(13) 0.45159(12) 0.85962(5) 0.0542(3) Uani 1 1 d . . . . .
N9_2 N -0.06616(14) 0.41689(13) 0.82323(5) 0.0718(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3493(13) . ?
O1_1 H1_1 0.921(18) . ?
C2_1 C7_1 1.3873(16) . ?
C2_1 C3_1 1.3945(15) . ?
C3_1 C4_1 1.3718(16) . ?
C3_1 H3_1 0.9300 . ?
C4_1 C5_1 1.3902(17) . ?
C4_1 H4_1 0.9300 . ?
C5_1 C6_1 1.3935(15) . ?
C5_1 C8_1 1.4339(16) . ?
C6_1 C7_1 1.3768(16) . ?
C6_1 H6_1 0.9300 . ?
C7_1 H7_1 0.9300 . ?
C8_1 N9_1 1.1442(16) . ?
O1_2 C2_2 1.3556(13) . ?
O1_2 H1_2 0.88(2) . ?
C2_2 C3_2 1.3834(16) . ?
C2_2 C7_2 1.3891(16) . ?
C3_2 C4_2 1.3783(16) . ?
C3_2 H3_2 0.9300 . ?
C4_2 C5_2 1.3895(16) . ?
C4_2 H4_2 0.9300 . ?
C5_2 C6_2 1.3878(16) . ?
C5_2 C8_2 1.4350(16) . ?
C6_2 C7_2 1.3750(16) . ?
C6_2 H6_2 0.9300 . ?
C7_2 H7_2 0.9300 . ?
C8_2 N9_2 1.1391(17) . ?

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
C2_1 O1_1 H1_1 110.5(11) . . ?
O1_1 C2_1 C7_1 122.54(9) . . ?
O1_1 C2_1 C3_1 117.39(10) . . ?
C7_1 C2_1 C3_1 120.07(10) . . ?
C4_1 C3_1 C2_1 120.17(10) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.90(10) . . ?
C3_1 C4_1 H4_1 120.0 . . ?
C5_1 C4_1 H4_1 120.0 . . ?
C4_1 C5_1 C6_1 119.92(10) . . ?
C4_1 C5_1 C8_1 121.06(10) . . ?
C6_1 C5_1 C8_1 119.01(10) . . ?
C7_1 C6_1 C5_1 120.18(10) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.75(10) . . ?
C6_1 C7_1 H7_1 120.1 . . ?
C2_1 C7_1 H7_1 120.1 . . ?
N9_1 C8_1 C5_1 177.98(13) . . ?
C2_2 O1_2 H1_2 108.5(12) . . ?
O1_2 C2_2 C3_2 117.79(10) . . ?
O1_2 C2_2 C7_2 121.97(10) . . ?
C3_2 C2_2 C7_2 120.24(10) . . ?
C4_2 C3_2 C2_2 120.09(10) . . ?
C4_2 C3_2 H3_2 120.0 . . ?
C2_2 C3_2 H3_2 120.0 . . ?
C3_2 C4_2 C5_2 119.89(10) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.72(10) . . ?
C6_2 C5_2 C8_2 119.44(10) . . ?
C4_2 C5_2 C8_2 120.83(10) . . ?
C7_2 C6_2 C5_2 120.47(10) . . ?
C7_2 C6_2 H6_2 119.8 . . ?
C5_2 C6_2 H6_2 119.8 . . ?
C6_2 C7_2 C2_2 119.58(10) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.58(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.80(10) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.27(17) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.08(18) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.45(17) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.27(11) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.49(17) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.26(10) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.15(17) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.73(10) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.23(17) . . . . ?
O1_2 C2_2 C3_2 C4_2 179.83(11) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.41(18) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.56(19) . . . . ?
C3_2 C4_2 C5_2 C6_2 -1.08(18) . . . . ?
C3_2 C4_2 C5_2 C8_2 178.11(11) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.63(17) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.56(10) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.33(17) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.76(10) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.85(17) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB240K
_database_code_depnum_ccdc_archive 'CCDC 954045'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.168(2)
_cell_length_b                   10.677(1)
_cell_length_c                   25.402(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2486.5(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    8947
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      32.89

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13423
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         31.102
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2463
_reflns_number_gt                2375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0552P)²+0.3589P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.422(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2463
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25374(10) 0.30132(8) 0.75085(3) 0.0497(3) Uani 1 1 d . . . . .
H1_1 H 0.1950(19) 0.3478(17) 0.7292(7) 0.074(5) Uiso 1 1 d . . . . .
C2_1 C 0.33236(11) 0.37807(10) 0.78213(4) 0.0397(3) Uani 1 1 d . . . . .
C3_1 C 0.43472(13) 0.32296(10) 0.81545(4) 0.0459(3) Uani 1 1 d . . . . .
H3_1 H 0.4464 0.2355 0.8156 0.055 Uiso 1 1 calc R U . . .
C4_1 C 0.51856(13) 0.39615(11) 0.84808(4) 0.0469(3) Uani 1 1 d . . . . .
H4_1 H 0.5877 0.3589 0.8705 0.056 Uiso 1 1 calc R U . . .
C5_1 C 0.50075(11) 0.52546(10) 0.84791(4) 0.0422(3) Uani 1 1 d . . . . .
C6_1 C 0.39898(12) 0.58058(10) 0.81444(4) 0.0441(3) Uani 1 1 d . . . . .
H6_1 H 0.3876 0.6681 0.8142 0.053 Uiso 1 1 calc R U . . .
C7_1 C 0.31498(12) 0.50745(10) 0.78167(4) 0.0419(3) Uani 1 1 d . . . . .
H7_1 H 0.2463 0.5448 0.7591 0.050 Uiso 1 1 calc R U . . .
C8_1 C 0.58367(13) 0.60380(11) 0.88264(5) 0.0496(3) Uani 1 1 d . . . . .
N9_1 N 0.64676(13) 0.66909(11) 0.91021(5) 0.0636(3) Uani 1 1 d . . . . .
O1_2 O 0.28840(10) 0.63920(9) 1.03358(3) 0.0569(3) Uani 1 1 d . . . . .
H1_2 H 0.238(2) 0.7038(19) 1.0473(7) 0.083(5) Uiso 1 1 d . . . . .
C2_2 C 0.21353(11) 0.59465(10) 0.99160(4) 0.0410(3) Uani 1 1 d . . . . .
C3_2 C 0.26957(13) 0.49121(12) 0.96561(4) 0.0490(3) Uani 1 1 d . . . . .
H3_2 H 0.3570 0.4544 0.9773 0.059 Uiso 1 1 calc R U . . .
C4_2 C 0.19741(13) 0.44205(12) 0.92268(4) 0.0483(3) Uani 1 1 d . . . . .
H4_2 H 0.2350 0.3714 0.9053 0.058 Uiso 1 1 calc R U . . .
C5_2 C 0.06889(12) 0.49731(10) 0.90524(4) 0.0409(3) Uani 1 1 d . . . . .
C6_2 C 0.01270(12) 0.60045(10) 0.93169(4) 0.0443(3) Uani 1 1 d . . . . .
H6_2 H -0.0747 0.6373 0.9201 0.053 Uiso 1 1 calc R U . . .
C7_2 C 0.08396(12) 0.64899(10) 0.97469(4) 0.0431(3) Uani 1 1 d . . . . .
H7_2 H 0.0453 0.7185 0.9926 0.052 Uiso 1 1 calc R U . . .
C8_2 C -0.00565(13) 0.45023(11) 0.85963(5) 0.0495(3) Uani 1 1 d . . . . .
N9_2 N -0.06590(14) 0.41550(12) 0.82319(4) 0.0657(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3499(13) . ?
O1_1 H1_1 0.916(18) . ?
C2_1 C7_1 1.3906(16) . ?
C2_1 C3_1 1.3940(15) . ?
C3_1 C4_1 1.3742(16) . ?
C3_1 H3_1 0.9400 . ?
C4_1 C5_1 1.3902(17) . ?
C4_1 H4_1 0.9400 . ?
C5_1 C6_1 1.3927(15) . ?
C5_1 C8_1 1.4339(16) . ?
C6_1 C7_1 1.3769(16) . ?
C6_1 H6_1 0.9400 . ?
C7_1 H7_1 0.9400 . ?
C8_1 N9_1 1.1449(16) . ?
O1_2 C2_2 1.3545(13) . ?
O1_2 H1_2 0.90(2) . ?
C2_2 C3_2 1.3855(16) . ?
C2_2 C7_2 1.3900(16) . ?
C3_2 C4_2 1.3792(16) . ?
C3_2 H3_2 0.9400 . ?
C4_2 C5_2 1.3902(16) . ?
C4_2 H4_2 0.9400 . ?
C5_2 C6_2 1.3891(16) . ?
C5_2 C8_2 1.4361(15) . ?
C6_2 C7_2 1.3742(15) . ?
C6_2 H6_2 0.9400 . ?
C7_2 H7_2 0.9400 . ?
C8_2 N9_2 1.1398(16) . ?

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
C2_1 O1_1 H1_1 109.8(11) . . ?
O1_1 C2_1 C7_1 122.46(9) . . ?
O1_1 C2_1 C3_1 117.43(10) . . ?
C7_1 C2_1 C3_1 120.11(10) . . ?
C4_1 C3_1 C2_1 120.18(10) . . ?
C4_1 C3_1 H3_1 119.9 . . ?
C2_1 C3_1 H3_1 119.9 . . ?
C3_1 C4_1 C5_1 119.81(10) . . ?
C3_1 C4_1 H4_1 120.1 . . ?
C5_1 C4_1 H4_1 120.1 . . ?
C4_1 C5_1 C6_1 120.02(10) . . ?
C4_1 C5_1 C8_1 121.00(10) . . ?
C6_1 C5_1 C8_1 118.97(10) . . ?
C7_1 C6_1 C5_1 120.27(10) . . ?
C7_1 C6_1 H6_1 119.9 . . ?
C5_1 C6_1 H6_1 119.9 . . ?
C6_1 C7_1 C2_1 119.61(9) . . ?
C6_1 C7_1 H7_1 120.2 . . ?
C2_1 C7_1 H7_1 120.2 . . ?
N9_1 C8_1 C5_1 177.94(13) . . ?
C2_2 O1_2 H1_2 108.2(12) . . ?
O1_2 C2_2 C3_2 117.85(10) . . ?
O1_2 C2_2 C7_2 121.98(10) . . ?
C3_2 C2_2 C7_2 120.16(10) . . ?
C4_2 C3_2 C2_2 120.14(10) . . ?
C4_2 C3_2 H3_2 119.9 . . ?
C2_2 C3_2 H3_2 119.9 . . ?
C3_2 C4_2 C5_2 119.80(10) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.78(10) . . ?
C6_2 C5_2 C8_2 119.43(10) . . ?
C4_2 C5_2 C8_2 120.79(10) . . ?
C7_2 C6_2 C5_2 120.47(10) . . ?
C7_2 C6_2 H6_2 119.8 . . ?
C5_2 C6_2 H6_2 119.8 . . ?
C6_2 C7_2 C2_2 119.63(10) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.47(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.73(10) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.19(17) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.19(17) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.50(17) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.15(11) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.43(17) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.24(10) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.05(17) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.77(10) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.26(16) . . . . ?
O1_2 C2_2 C3_2 C4_2 179.89(11) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.32(18) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.59(19) . . . . ?
C3_2 C4_2 C5_2 C6_2 -1.06(18) . . . . ?
C3_2 C4_2 C5_2 C8_2 178.00(11) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.61(17) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.46(10) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.30(17) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.68(10) . . . . ?
C3_2 C2_2 C7_2 C6_2 -0.77(17) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034

_shelxl_version_number           2012-9

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4HCB280K
_database_code_depnum_ccdc_archive 'CCDC 953964'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            4-hydroxycyanobenzene
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 N O'
_chemical_formula_sum            'C7 H5 N O'
_chemical_formula_weight         119.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0031 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0042 0.0085 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   9.191(4)
_cell_length_b                   10.716(3)
_cell_length_c                   25.440(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2505.6(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    280(2)
_cell_measurement_reflns_used    3114
_cell_measurement_theta_min      0.93
_cell_measurement_theta_max      32.87

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      280(2)
_diffrn_radiation_wavelength     0.8266
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6776
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         30.266
_diffrn_reflns_theta_full        29.733
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             2187
_reflns_number_gt                2009
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - SCALA (Winn, 2011)'
_computing_structure_solution    'Sir2011 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2015)'
_computing_molecular_graphics    'Coot (Emsley, 2004)'
_computing_publication_material  enCIFer/publCIF

_refine_special_details          
;
Anisotropic thermal motion modeling was then applied to atoms with 
full occupancy. In the final refinement, all non-hydrogen atoms 
were treated anisotropically and the hydrogen atoms were included 
at calculated positions with isotropic Ufactors = 1.2 Ueq, except 
for H1 which has coordinates and isotropic thermal motion parameters 
refined without restrains. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0744P)²+0.2463P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.51(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2187
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.25357(12) 0.30444(10) 0.75097(4) 0.0596(3) Uani 1 1 d . . . . .
H1_1 H 0.198(2) 0.346(3) 0.7296(9) 0.102(7) Uiso 1 1 d . . . . .
C2_1 C 0.33212(13) 0.38128(13) 0.78221(4) 0.0476(4) Uani 1 1 d . . . . .
C3_1 C 0.43405(15) 0.32624(13) 0.81544(5) 0.0543(4) Uani 1 1 d . . . . .
H3_1 H 0.4457 0.2400 0.8155 0.065 Uiso 1 1 calc R U . . .
C4_1 C 0.51729(15) 0.39906(14) 0.84806(5) 0.0557(4) Uani 1 1 d . . . . .
H4_1 H 0.5852 0.3622 0.8703 0.067 Uiso 1 1 calc R U . . .
C5_1 C 0.50020(13) 0.52773(14) 0.84793(5) 0.0504(4) Uani 1 1 d . . . . .
C6_1 C 0.39858(14) 0.58300(14) 0.81430(5) 0.0521(4) Uani 1 1 d . . . . .
H6_1 H 0.3874 0.6693 0.8140 0.062 Uiso 1 1 calc R U . . .
C7_1 C 0.31508(14) 0.50960(13) 0.78169(5) 0.0499(4) Uani 1 1 d . . . . .
H7_1 H 0.2473 0.5462 0.7593 0.060 Uiso 1 1 calc R U . . .
C8_1 C 0.58293(15) 0.60543(15) 0.88250(5) 0.0590(4) Uani 1 1 d . . . . .
N9_1 N 0.64641(16) 0.67044(15) 0.90991(5) 0.0769(5) Uani 1 1 d . . . . .
O1_2 O 0.28694(12) 0.63883(13) 1.03352(4) 0.0680(4) Uani 1 1 d . . . . .
H1_2 H 0.239(2) 0.700(2) 1.0479(8) 0.082(6) Uiso 1 1 d . . . . .
C2_2 C 0.21250(13) 0.59531(13) 0.99147(4) 0.0487(4) Uani 1 1 d . . . . .
C3_2 C 0.26768(15) 0.49210(16) 0.96552(5) 0.0590(4) Uani 1 1 d . . . . .
H3_2 H 0.3534 0.4552 0.9771 0.071 Uiso 1 1 calc R U . . .
C4_2 C 0.19587(15) 0.44401(15) 0.92256(5) 0.0580(4) Uani 1 1 d . . . . .
H4_2 H 0.2328 0.3745 0.9052 0.070 Uiso 1 1 calc R U . . .
C5_2 C 0.06806(13) 0.49958(13) 0.90519(4) 0.0488(4) Uani 1 1 d . . . . .
C6_2 C 0.01281(13) 0.60204(14) 0.93157(5) 0.0531(4) Uani 1 1 d . . . . .
H6_2 H -0.0731 0.6389 0.9201 0.064 Uiso 1 1 calc R U . . .
C7_2 C 0.08386(14) 0.64974(14) 0.97463(5) 0.0519(4) Uani 1 1 d . . . . .
H7_2 H 0.0458 0.7182 0.9924 0.062 Uiso 1 1 calc R U . . .
C8_2 C -0.00634(15) 0.45282(15) 0.85967(5) 0.0586(4) Uani 1 1 d . . . . .
N9_2 N -0.06632(17) 0.41798(17) 0.82329(5) 0.0787(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1_1 C2_1 1.3532(16) . ?
O1_1 H1_1 0.87(3) . ?
C2_1 C7_1 1.384(2) . ?
C2_1 C3_1 1.3928(18) . ?
C3_1 C4_1 1.3722(19) . ?
C3_1 H3_1 0.9300 . ?
C4_1 C5_1 1.388(2) . ?
C4_1 H4_1 0.9300 . ?
C5_1 C6_1 1.3982(18) . ?
C5_1 C8_1 1.4300(19) . ?
C6_1 C7_1 1.3769(19) . ?
C6_1 H6_1 0.9300 . ?
C7_1 H7_1 0.9300 . ?
C8_1 N9_1 1.1454(19) . ?
O1_2 C2_2 1.3529(15) . ?
O1_2 H1_2 0.87(2) . ?
C2_2 C3_2 1.384(2) . ?
C2_2 C7_2 1.3862(19) . ?
C3_2 C4_2 1.3769(19) . ?
C3_2 H3_2 0.9300 . ?
C4_2 C5_2 1.389(2) . ?
C4_2 H4_2 0.9300 . ?
C5_2 C6_2 1.383(2) . ?
C5_2 C8_2 1.4351(18) . ?
C6_2 C7_2 1.3739(18) . ?
C6_2 H6_2 0.9300 . ?
C7_2 H7_2 0.9300 . ?
C8_2 N9_2 1.1400(19) . ?

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
C2_1 O1_1 H1_1 111.5(17) . . ?
O1_1 C2_1 C7_1 122.59(11) . . ?
O1_1 C2_1 C3_1 117.24(12) . . ?
C7_1 C2_1 C3_1 120.17(12) . . ?
C4_1 C3_1 C2_1 120.08(13) . . ?
C4_1 C3_1 H3_1 120.0 . . ?
C2_1 C3_1 H3_1 120.0 . . ?
C3_1 C4_1 C5_1 120.03(11) . . ?
C3_1 C4_1 H4_1 120.0 . . ?
C5_1 C4_1 H4_1 120.0 . . ?
C4_1 C5_1 C6_1 119.87(12) . . ?
C4_1 C5_1 C8_1 121.12(11) . . ?
C6_1 C5_1 C8_1 119.00(13) . . ?
C7_1 C6_1 C5_1 119.93(13) . . ?
C7_1 C6_1 H6_1 120.0 . . ?
C5_1 C6_1 H6_1 120.0 . . ?
C6_1 C7_1 C2_1 119.92(11) . . ?
C6_1 C7_1 H7_1 120.0 . . ?
C2_1 C7_1 H7_1 120.0 . . ?
N9_1 C8_1 C5_1 178.01(16) . . ?
C2_2 O1_2 H1_2 109.6(13) . . ?
O1_2 C2_2 C3_2 117.86(12) . . ?
O1_2 C2_2 C7_2 122.05(13) . . ?
C3_2 C2_2 C7_2 120.09(11) . . ?
C4_2 C3_2 C2_2 120.13(12) . . ?
C4_2 C3_2 H3_2 119.9 . . ?
C2_2 C3_2 H3_2 119.9 . . ?
C3_2 C4_2 C5_2 119.83(13) . . ?
C3_2 C4_2 H4_2 120.1 . . ?
C5_2 C4_2 H4_2 120.1 . . ?
C6_2 C5_2 C4_2 119.76(12) . . ?
C6_2 C5_2 C8_2 119.58(12) . . ?
C4_2 C5_2 C8_2 120.66(13) . . ?
C7_2 C6_2 C5_2 120.50(12) . . ?
C7_2 C6_2 H6_2 119.7 . . ?
C5_2 C6_2 H6_2 119.7 . . ?
C6_2 C7_2 C2_2 119.68(13) . . ?
C6_2 C7_2 H7_2 120.2 . . ?
C2_2 C7_2 H7_2 120.2 . . ?
N9_2 C8_2 C5_2 178.66(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1_1 C2_1 C3_1 C4_1 179.93(11) . . . . ?
C7_1 C2_1 C3_1 C4_1 0.4(2) . . . . ?
C2_1 C3_1 C4_1 C5_1 -0.1(2) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.35(19) . . . . ?
C3_1 C4_1 C5_1 C8_1 178.37(13) . . . . ?
C4_1 C5_1 C6_1 C7_1 0.5(2) . . . . ?
C8_1 C5_1 C6_1 C7_1 -178.29(12) . . . . ?
C5_1 C6_1 C7_1 C2_1 -0.1(2) . . . . ?
O1_1 C2_1 C7_1 C6_1 -179.78(12) . . . . ?
C3_1 C2_1 C7_1 C6_1 -0.33(19) . . . . ?
O1_2 C2_2 C3_2 C4_2 179.86(13) . . . . ?
C7_2 C2_2 C3_2 C4_2 0.7(2) . . . . ?
C2_2 C3_2 C4_2 C5_2 0.2(2) . . . . ?
C3_2 C4_2 C5_2 C6_2 -0.8(2) . . . . ?
C3_2 C4_2 C5_2 C8_2 178.37(13) . . . . ?
C4_2 C5_2 C6_2 C7_2 0.4(2) . . . . ?
C8_2 C5_2 C6_2 C7_2 -178.75(12) . . . . ?
C5_2 C6_2 C7_2 C2_2 0.5(2) . . . . ?
O1_2 C2_2 C7_2 C6_2 179.81(12) . . . . ?
C3_2 C2_2 C7_2 C6_2 -1.1(2) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039

_shelxl_version_number           2012-9

