# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5-chloro-4'-methyl-2'-nitro-[1,1'-biphenyl]-2-ol

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Cl N O3'
_chemical_formula_weight         261.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.9194(3)
_cell_length_b                   8.8519(3)
_cell_length_c                   17.3430(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1215.77(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.312
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8652
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.647
_diffrn_reflns_theta_max         28.064
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2912
_reflns_number_gt                2551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2912
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Cl1 Cl 0.67530(10) 0.45124(9) 1.18155(4) 0.0622(2) Uani 1 1 d . . . . .
O1 O 0.7897(3) -0.2056(2) 0.88861(13) 0.0695(7) Uani 1 1 d . . . . .
O2 O 0.8495(2) -0.0610(2) 0.98425(10) 0.0541(5) Uani 1 1 d . . . . .
O3 O 0.4660(2) -0.0790(2) 1.00423(10) 0.0509(5) Uani 1 1 d . . . . .
H7 H 0.417(4) -0.147(5) 1.0301(19) 0.076 Uiso 1 1 d . U . . .
C13 C 0.6448(4) 0.1642(3) 0.67366(14) 0.0566(7) Uani 1 1 d . . . . .
H10 H 0.5341 0.1872 0.6544 0.085 Uiso 1 1 calc R U . . .
H8 H 0.6794 0.0669 0.6550 0.085 Uiso 1 1 calc R U . . .
H9 H 0.7232 0.2396 0.6562 0.085 Uiso 1 1 calc R U . . .
C10 C 0.5247(3) 0.1796(3) 1.16696(12) 0.0419(6) Uani 1 1 d . . . . .
H5 H 0.5003 0.1871 1.2193 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6103(3) 0.2930(3) 1.13000(12) 0.0375(5) Uani 1 1 d . . . . .
C12 C 0.6454(3) 0.2851(3) 1.05190(13) 0.0346(5) Uani 1 1 d . . . . .
H6 H 0.7011 0.3645 1.0277 0.042 Uiso 1 1 calc R U . . .
C7 C 0.5976(3) 0.1589(3) 1.00962(11) 0.0314(5) Uani 1 1 d . . . . .
C6 C 0.6239(2) 0.1574(3) 0.92471(11) 0.0298(4) Uani 1 1 d . . . . .
C1 C 0.6996(3) 0.0432(3) 0.88225(11) 0.0317(4) Uani 1 1 d . . . . .
C2 C 0.7069(3) 0.0426(3) 0.80248(12) 0.0357(5) Uani 1 1 d . . . . .
H1 H 0.7559 -0.0385 0.7768 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6412(3) 0.1627(3) 0.76079(12) 0.0364(5) Uani 1 1 d . . . . .
N1 N 0.7842(3) -0.0834(2) 0.92170(12) 0.0427(5) Uani 1 1 d . . . . .
C9 C 0.4755(3) 0.0544(3) 1.12558(12) 0.0423(6) Uani 1 1 d . . . . .
H4 H 0.4170 -0.0230 1.1501 0.051 Uiso 1 1 calc R U . . .
C8 C 0.5124(3) 0.0427(3) 1.04744(12) 0.0351(5) Uani 1 1 d . . . . .
C5 C 0.5613(3) 0.2772(3) 0.88198(12) 0.0359(5) Uani 1 1 d . . . . .
H3 H 0.5113 0.3578 0.9077 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5710(3) 0.2808(3) 0.80189(12) 0.0394(5) Uani 1 1 d . . . . .
H2 H 0.5293 0.3644 0.7755 0.047 Uiso 1 1 calc R U . . .


_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
Cl1 C11 1.739(3) . ?
O1 N1 1.225(3) . ?
O2 N1 1.218(3) . ?
O3 C8 1.363(3) . ?
O3 H7 0.84(4) . ?
C13 C3 1.511(3) . ?
C13 H10 0.9600 . ?
C13 H8 0.9600 . ?
C13 H9 0.9600 . ?
C10 C11 1.370(4) . ?
C10 C9 1.377(4) . ?
C10 H5 0.9300 . ?
C11 C12 1.385(3) . ?
C12 C7 1.389(3) . ?
C12 H6 0.9300 . ?
C7 C8 1.394(3) . ?
C7 C6 1.487(3) . ?
C6 C5 1.386(3) . ?
C6 C1 1.387(3) . ?
C1 C2 1.385(3) . ?
C1 N1 1.474(3) . ?
C2 C3 1.386(3) . ?
C2 H1 0.9300 . ?
C3 C4 1.383(3) . ?
C9 C8 1.390(3) . ?
C9 H4 0.9300 . ?
C5 C4 1.392(3) . ?
C5 H3 0.9300 . ?
C4 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 H7 113(2) . . ?
C3 C13 H10 109.5 . . ?
C3 C13 H8 109.5 . . ?
H10 C13 H8 109.5 . . ?
C3 C13 H9 109.5 . . ?
H10 C13 H9 109.5 . . ?
H8 C13 H9 109.5 . . ?
C11 C10 C9 119.09(19) . . ?
C11 C10 H5 120.5 . . ?
C9 C10 H5 120.5 . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 Cl1 119.73(16) . . ?
C12 C11 Cl1 119.0(2) . . ?
C11 C12 C7 120.2(2) . . ?
C11 C12 H6 119.9 . . ?
C7 C12 H6 119.9 . . ?
C12 C7 C8 118.48(18) . . ?
C12 C7 C6 119.47(19) . . ?
C8 C7 C6 121.79(19) . . ?
C5 C6 C1 115.39(17) . . ?
C5 C6 C7 118.20(19) . . ?
C1 C6 C7 126.35(18) . . ?
C2 C1 C6 123.4(2) . . ?
C2 C1 N1 116.3(2) . . ?
C6 C1 N1 120.27(17) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H1 119.9 . . ?
C3 C2 H1 119.9 . . ?
C4 C3 C2 117.50(18) . . ?
C4 C3 C13 121.1(2) . . ?
C2 C3 C13 121.4(2) . . ?
O2 N1 O1 123.1(2) . . ?
O2 N1 C1 118.9(2) . . ?
O1 N1 C1 118.0(2) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H4 119.7 . . ?
C8 C9 H4 119.7 . . ?
O3 C8 C9 122.6(2) . . ?
O3 C8 C7 117.08(18) . . ?
C9 C8 C7 120.4(2) . . ?
C6 C5 C4 122.1(2) . . ?
C6 C5 H3 118.9 . . ?
C4 C5 H3 118.9 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H2 119.4 . . ?
C5 C4 H2 119.4 . . ?

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
C9 C10 C11 C12 1.1(3) . . . . ?
C9 C10 C11 Cl1 -179.37(17) . . . . ?
C10 C11 C12 C7 -1.6(3) . . . . ?
Cl1 C11 C12 C7 178.83(17) . . . . ?
C11 C12 C7 C8 0.8(3) . . . . ?
C11 C12 C7 C6 175.14(19) . . . . ?
C12 C7 C6 C5 -52.4(3) . . . . ?
C8 C7 C6 C5 121.8(2) . . . . ?
C12 C7 C6 C1 130.7(2) . . . . ?
C8 C7 C6 C1 -55.1(3) . . . . ?
C5 C6 C1 C2 -2.9(3) . . . . ?
C7 C6 C1 C2 174.1(2) . . . . ?
C5 C6 C1 N1 174.5(2) . . . . ?
C7 C6 C1 N1 -8.5(3) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
N1 C1 C2 C3 -175.44(19) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C13 -179.0(2) . . . . ?
C2 C1 N1 O2 147.1(2) . . . . ?
C6 C1 N1 O2 -30.6(3) . . . . ?
C2 C1 N1 O1 -30.8(3) . . . . ?
C6 C1 N1 O1 151.6(2) . . . . ?
C11 C10 C9 C8 0.2(3) . . . . ?
C10 C9 C8 O3 -179.9(2) . . . . ?
C10 C9 C8 C7 -1.0(3) . . . . ?
C12 C7 C8 O3 179.4(2) . . . . ?
C6 C7 C8 O3 5.2(3) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C6 C7 C8 C9 -173.7(2) . . . . ?
C1 C6 C5 C4 1.2(3) . . . . ?
C7 C6 C5 C4 -176.0(2) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C13 C3 C4 C5 177.4(2) . . . . ?
C6 C5 C4 C3 1.2(4) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 992291'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_5-bromo-4'-methyl-2'-nitro-[1,1'-biphenyl]-2-ol

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Br N O3'
_chemical_formula_weight         308.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.9842(14)
_cell_length_b                   8.9505(15)
_cell_length_c                   17.463(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1248.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    305(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.292
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      305(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.557
_diffrn_reflns_theta_max         30.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.570
_diffrn_reflns_point_group_measured_fraction_full 0.586
_reflns_number_total             2091
_reflns_number_gt                1538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.415(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2091
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1396
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Br1 Br 0.32108(7) 0.03621(6) 1.17886(3) 0.0608(2) Uani 1 1 d . . . . .
O3 O 0.5339(5) 0.5806(4) 1.0032(2) 0.0535(9) Uani 1 1 d . . . . .
H7 H 0.5789 0.6420 1.0313 0.080 Uiso 1 1 calc R U . . .
O2 O 0.1518(5) 0.5644(5) 0.9831(2) 0.0582(10) Uani 1 1 d . . . . .
O1 O 0.2133(7) 0.7105(4) 0.8902(3) 0.0736(13) Uani 1 1 d . . . . .
C3 C 0.3588(6) 0.3501(5) 0.7598(3) 0.0392(10) Uani 1 1 d . . . . .
C10 C 0.4760(6) 0.3189(6) 1.1626(3) 0.0445(11) Uani 1 1 d . . . . .
H5 H 0.4996 0.3098 1.2146 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3906(6) 0.2089(5) 1.1245(3) 0.0391(9) Uani 1 1 d . . . . .
C8 C 0.3557(5) 0.2188(5) 1.0472(2) 0.0372(9) Uani 1 1 d . . . . .
H4 H 0.3007 0.1409 1.0225 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4026(5) 0.3450(5) 1.0065(2) 0.0331(8) Uani 1 1 d . . . . .
C6 C 0.3757(5) 0.3492(5) 0.9222(2) 0.0322(8) Uani 1 1 d . . . . .
C5 C 0.4376(6) 0.2310(5) 0.8790(3) 0.0387(9) Uani 1 1 d . . . . .
H3 H 0.4878 0.1504 0.9036 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4257(6) 0.2315(5) 0.7996(2) 0.0415(10) Uani 1 1 d . . . . .
H2 H 0.4642 0.1490 0.7725 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3568(9) 0.3529(7) 0.6743(3) 0.0600(14) Uani 1 1 d . . . . .
H8 H 0.3399 0.4536 0.6569 0.090 Uiso 1 1 calc R U . . .
H10 H 0.2675 0.2908 0.6559 0.090 Uiso 1 1 calc R U . . .
H9 H 0.4618 0.3162 0.6551 0.090 Uiso 1 1 calc R U . . .
C11 C 0.5265(6) 0.4443(5) 1.1219(3) 0.0443(10) Uani 1 1 d . . . . .
H6 H 0.5869 0.5188 1.1467 0.053 Uiso 1 1 calc R U . . .
C12 C 0.4882(5) 0.4601(5) 1.0447(2) 0.0369(8) Uani 1 1 d . . . . .
C1 C 0.3001(5) 0.4663(4) 0.8811(2) 0.0335(8) Uani 1 1 d . . . . .
N1 N 0.2178(5) 0.5889(5) 0.9217(3) 0.0473(10) Uani 1 1 d . . . . .
C2 C 0.2924(5) 0.4679(5) 0.8021(3) 0.0379(9) Uani 1 1 d . . . . .
H1 H 0.2427 0.5481 0.7770 0.046 Uiso 1 1 calc R U . . .


_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
Br1 C9 1.897(5) . ?
O3 C12 1.349(6) . ?
O3 H7 0.8200 . ?
O2 N1 1.214(6) . ?
O1 N1 1.221(6) . ?
C3 C4 1.377(7) . ?
C3 C2 1.392(6) . ?
C3 C13 1.493(7) . ?
C10 C9 1.370(7) . ?
C10 C11 1.389(7) . ?
C10 H5 0.9300 . ?
C9 C8 1.382(6) . ?
C8 C7 1.387(6) . ?
C8 H4 0.9300 . ?
C7 C12 1.405(6) . ?
C7 C6 1.488(6) . ?
C6 C5 1.391(6) . ?
C6 C1 1.406(6) . ?
C5 C4 1.389(6) . ?
C5 H3 0.9300 . ?
C4 H2 0.9300 . ?
C13 H8 0.9600 . ?
C13 H10 0.9600 . ?
C13 H9 0.9600 . ?
C11 C12 1.390(6) . ?
C11 H6 0.9300 . ?
C1 C2 1.381(6) . ?
C1 N1 1.463(6) . ?
C2 H1 0.9300 . ?

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
C12 O3 H7 109.5 . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 C13 121.5(4) . . ?
C2 C3 C13 120.9(4) . . ?
C9 C10 C11 118.4(4) . . ?
C9 C10 H5 120.8 . . ?
C11 C10 H5 120.8 . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 Br1 119.2(3) . . ?
C8 C9 Br1 118.8(4) . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H4 120.0 . . ?
C7 C8 H4 120.0 . . ?
C8 C7 C12 119.0(4) . . ?
C8 C7 C6 119.3(4) . . ?
C12 C7 C6 121.4(4) . . ?
C5 C6 C1 116.3(4) . . ?
C5 C6 C7 117.8(4) . . ?
C1 C6 C7 125.9(4) . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H3 119.5 . . ?
C6 C5 H3 119.5 . . ?
C3 C4 C5 122.2(4) . . ?
C3 C4 H2 118.9 . . ?
C5 C4 H2 118.9 . . ?
C3 C13 H8 109.5 . . ?
C3 C13 H10 109.5 . . ?
H8 C13 H10 109.5 . . ?
C3 C13 H9 109.5 . . ?
H8 C13 H9 109.5 . . ?
H10 C13 H9 109.5 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H6 119.5 . . ?
C12 C11 H6 119.5 . . ?
O3 C12 C11 122.9(4) . . ?
O3 C12 C7 117.6(4) . . ?
C11 C12 C7 119.5(4) . . ?
C2 C1 C6 122.4(4) . . ?
C2 C1 N1 117.2(4) . . ?
C6 C1 N1 120.3(4) . . ?
O2 N1 O1 123.1(4) . . ?
O2 N1 C1 119.2(4) . . ?
O1 N1 C1 117.6(4) . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H1 119.8 . . ?
C3 C2 H1 119.8 . . ?

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
C11 C10 C9 C8 0.8(7) . . . . ?
C11 C10 C9 Br1 179.8(3) . . . . ?
C10 C9 C8 C7 -2.1(7) . . . . ?
Br1 C9 C8 C7 178.9(3) . . . . ?
C9 C8 C7 C12 1.2(6) . . . . ?
C9 C8 C7 C6 175.4(4) . . . . ?
C8 C7 C6 C5 -52.2(6) . . . . ?
C12 C7 C6 C5 121.9(5) . . . . ?
C8 C7 C6 C1 131.3(4) . . . . ?
C12 C7 C6 C1 -54.6(6) . . . . ?
C1 C6 C5 C4 0.6(7) . . . . ?
C7 C6 C5 C4 -176.3(4) . . . . ?
C2 C3 C4 C5 -4.0(7) . . . . ?
C13 C3 C4 C5 176.1(5) . . . . ?
C6 C5 C4 C3 2.6(7) . . . . ?
C9 C10 C11 C12 1.5(7) . . . . ?
C10 C11 C12 O3 179.5(5) . . . . ?
C10 C11 C12 C7 -2.4(7) . . . . ?
C8 C7 C12 O3 179.2(4) . . . . ?
C6 C7 C12 O3 5.1(6) . . . . ?
C8 C7 C12 C11 1.0(6) . . . . ?
C6 C7 C12 C11 -173.1(4) . . . . ?
C5 C6 C1 C2 -2.3(6) . . . . ?
C7 C6 C1 C2 174.3(4) . . . . ?
C5 C6 C1 N1 174.4(4) . . . . ?
C7 C6 C1 N1 -8.9(7) . . . . ?
C2 C1 N1 O2 145.7(4) . . . . ?
C6 C1 N1 O2 -31.2(7) . . . . ?
C2 C1 N1 O1 -31.3(7) . . . . ?
C6 C1 N1 O1 151.7(5) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
N1 C1 C2 C3 -176.0(4) . . . . ?
C4 C3 C2 C1 2.3(7) . . . . ?
C13 C3 C2 C1 -177.8(5) . . . . ?

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 993002'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2,3,4',5-tetramethyl-2'-nitro-[1,1'-biphenyl]-4-ol

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8419(3)
_cell_length_b                   8.4340(3)
_cell_length_c                   12.6395(5)
_cell_angle_alpha                82.195(3)
_cell_angle_beta                 79.847(3)
_cell_angle_gamma                85.040(2)
_cell_volume                     709.82(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2208
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.242
_reflns_number_total             2208
_reflns_number_gt                1787
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0732P)²+0.1709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2208
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0248(2) 0.74295(17) -0.14039(12) 0.0601(4) Uani 1 1 d . . .
H1 H -0.116(4) 0.680(3) -0.141(2) 0.090 Uiso 1 1 d . . .
O3 O 0.1723(3) 0.37230(18) 0.39304(15) 0.1008(7) Uani 1 1 d . . .
O2 O 0.2850(3) 0.45272(17) 0.22689(15) 0.0701(5) Uani 1 1 d . . .
N1 N 0.2229(3) 0.47828(18) 0.31991(16) 0.0569(5) Uani 1 1 d . . .
C1 C 0.0078(3) 0.74893(19) -0.03661(16) 0.0439(5) Uani 1 1 d . . .
C2 C -0.1193(3) 0.68245(19) 0.05402(17) 0.0440(5) Uani 1 1 d . . .
C3 C -0.0745(3) 0.6883(2) 0.15704(16) 0.0454(5) Uani 1 1 d . . .
C4 C 0.0988(3) 0.75933(19) 0.16743(15) 0.0434(5) Uani 1 1 d . . .
C10 C 0.1587(3) 0.7718(2) 0.27335(16) 0.0442(5) Uani 1 1 d . . .
C16 C 0.1641(3) 0.9221(2) 0.30615(17) 0.0547(5) Uani 1 1 d . . .
H17 H 0.1323 1.0127 0.2601 0.066 Uiso 1 1 calc R . .
C15 C 0.2147(3) 0.9423(2) 0.40426(18) 0.0604(6) Uani 1 1 d . . .
H16 H 0.2158 1.0455 0.4223 0.073 Uiso 1 1 calc R . .
C13 C 0.2640(3) 0.8127(3) 0.47636(17) 0.0565(6) Uani 1 1 d . . .
C14 C 0.3136(4) 0.8343(3) 0.5849(2) 0.0797(7) Uani 1 1 d . . .
H15 H 0.3273 0.9459 0.5877 0.119 Uiso 1 1 calc R . .
H14 H 0.4363 0.7744 0.5948 0.119 Uiso 1 1 calc R . .
H13 H 0.2089 0.7964 0.6413 0.119 Uiso 1 1 calc R . .
C9 C -0.2135(3) 0.6236(3) 0.25735(19) 0.0671(6) Uani 1 1 d . . .
H6 H -0.3453 0.6717 0.2550 0.101 Uiso 1 1 calc R . .
H7 H -0.1684 0.6487 0.3205 0.101 Uiso 1 1 calc R . .
H5 H -0.2150 0.5094 0.2602 0.101 Uiso 1 1 calc R . .
C5 C 0.2155(3) 0.82984(19) 0.07416(15) 0.0446(5) Uani 1 1 d . . .
H8 H 0.3256 0.8824 0.0815 0.054 Uiso 1 1 calc R . .
C6 C 0.1756(3) 0.82540(19) -0.02822(16) 0.0449(5) Uani 1 1 d . . .
C7 C 0.3095(4) 0.8960(2) -0.12826(17) 0.0607(6) Uani 1 1 d . . .
H9 H 0.4108 0.9514 -0.1075 0.091 Uiso 1 1 calc R . .
H11 H 0.2324 0.9700 -0.1717 0.091 Uiso 1 1 calc R . .
H10 H 0.3705 0.8117 -0.1693 0.091 Uiso 1 1 calc R . .
C12 C 0.2601(3) 0.6612(2) 0.44576(17) 0.0531(5) Uani 1 1 d . . .
H12 H 0.2904 0.5709 0.4924 0.064 Uiso 1 1 calc R . .
C11 C 0.2118(3) 0.6432(2) 0.34721(16) 0.0461(5) Uani 1 1 d . . .
C8 C -0.3027(3) 0.6071(2) 0.03800(19) 0.0605(6) Uani 1 1 d . . .
H2 H -0.3806 0.6839 -0.0032 0.091 Uiso 1 1 calc R . .
H4 H -0.3803 0.5740 0.1073 0.091 Uiso 1 1 calc R . .
H3 H -0.2637 0.5155 -0.0002 0.091 Uiso 1 1 calc R . .


_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 C1 1.377(2) . ?
O1 H1 0.85(3) . ?
O3 N1 1.220(2) . ?
O2 N1 1.219(2) . ?
N1 C11 1.470(2) . ?
C1 C6 1.391(3) . ?
C1 C2 1.393(3) . ?
C2 C3 1.397(3) . ?
C2 C8 1.511(3) . ?
C3 C4 1.407(3) . ?
C3 C9 1.512(3) . ?
C4 C5 1.393(2) . ?
C4 C10 1.487(3) . ?
C10 C16 1.392(3) . ?
C10 C11 1.399(3) . ?
C16 C15 1.380(3) . ?
C16 H17 0.9300 . ?
C15 C13 1.383(3) . ?
C15 H16 0.9300 . ?
C13 C12 1.388(3) . ?
C13 C14 1.508(3) . ?
C14 H15 0.9600 . ?
C14 H14 0.9600 . ?
C14 H13 0.9600 . ?
C9 H6 0.9600 . ?
C9 H7 0.9600 . ?
C9 H5 0.9600 . ?
C5 C6 1.375(3) . ?
C5 H8 0.9300 . ?
C6 C7 1.508(3) . ?
C7 H9 0.9600 . ?
C7 H11 0.9600 . ?
C7 H10 0.9600 . ?
C12 C11 1.374(3) . ?
C12 H12 0.9300 . ?
C8 H2 0.9600 . ?
C8 H4 0.9600 . ?
C8 H3 0.9600 . ?

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
C1 O1 H1 111.7(18) . . ?
O2 N1 O3 123.03(18) . . ?
O2 N1 C11 119.25(16) . . ?
O3 N1 C11 117.7(2) . . ?
O1 C1 C6 115.72(17) . . ?
O1 C1 C2 122.02(16) . . ?
C6 C1 C2 122.27(18) . . ?
C1 C2 C3 119.20(16) . . ?
C1 C2 C8 118.94(18) . . ?
C3 C2 C8 121.86(17) . . ?
C2 C3 C4 119.57(16) . . ?
C2 C3 C9 120.63(17) . . ?
C4 C3 C9 119.77(19) . . ?
C5 C4 C3 118.57(18) . . ?
C5 C4 C10 117.78(16) . . ?
C3 C4 C10 123.56(16) . . ?
C16 C10 C11 114.46(18) . . ?
C16 C10 C4 119.65(16) . . ?
C11 C10 C4 125.89(16) . . ?
C15 C16 C10 122.68(18) . . ?
C15 C16 H17 118.7 . . ?
C10 C16 H17 118.7 . . ?
C13 C15 C16 121.55(19) . . ?
C13 C15 H16 119.2 . . ?
C16 C15 H16 119.2 . . ?
C15 C13 C12 117.0(2) . . ?
C15 C13 C14 121.6(2) . . ?
C12 C13 C14 121.3(2) . . ?
C13 C14 H15 109.5 . . ?
C13 C14 H14 109.5 . . ?
H15 C14 H14 109.5 . . ?
C13 C14 H13 109.5 . . ?
H15 C14 H13 109.5 . . ?
H14 C14 H13 109.5 . . ?
C3 C9 H6 109.5 . . ?
C3 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
C3 C9 H5 109.5 . . ?
H6 C9 H5 109.5 . . ?
H7 C9 H5 109.5 . . ?
C6 C5 C4 123.04(17) . . ?
C6 C5 H8 118.5 . . ?
C4 C5 H8 118.5 . . ?
C5 C6 C1 117.23(17) . . ?
C5 C6 C7 122.06(17) . . ?
C1 C6 C7 120.70(18) . . ?
C6 C7 H9 109.5 . . ?
C6 C7 H11 109.5 . . ?
H9 C7 H11 109.5 . . ?
C6 C7 H10 109.5 . . ?
H9 C7 H10 109.5 . . ?
H11 C7 H10 109.5 . . ?
C11 C12 C13 120.69(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C11 C10 123.55(17) . . ?
C12 C11 N1 116.45(16) . . ?
C10 C11 N1 119.98(18) . . ?
C2 C8 H2 109.5 . . ?
C2 C8 H4 109.5 . . ?
H2 C8 H4 109.5 . . ?
C2 C8 H3 109.5 . . ?
H2 C8 H3 109.5 . . ?
H4 C8 H3 109.5 . . ?

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 C1 C2 C3 178.10(15) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
O1 C1 C2 C8 -2.4(3) . . . . ?
C6 C1 C2 C8 177.67(16) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C8 C2 C3 C4 179.73(16) . . . . ?
C1 C2 C3 C9 177.42(17) . . . . ?
C8 C2 C3 C9 -2.1(3) . . . . ?
C2 C3 C4 C5 3.5(3) . . . . ?
C9 C3 C4 C5 -174.73(17) . . . . ?
C2 C3 C4 C10 179.79(15) . . . . ?
C9 C3 C4 C10 1.6(3) . . . . ?
C5 C4 C10 C16 61.5(2) . . . . ?
C3 C4 C10 C16 -114.9(2) . . . . ?
C5 C4 C10 C11 -118.9(2) . . . . ?
C3 C4 C10 C11 64.8(3) . . . . ?
C11 C10 C16 C15 -1.0(3) . . . . ?
C4 C10 C16 C15 178.77(19) . . . . ?
C10 C16 C15 C13 0.1(3) . . . . ?
C16 C15 C13 C12 -0.1(3) . . . . ?
C16 C15 C13 C14 -178.2(2) . . . . ?
C3 C4 C5 C6 -3.8(3) . . . . ?
C10 C4 C5 C6 179.64(16) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -177.15(17) . . . . ?
O1 C1 C6 C5 -178.35(15) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
O1 C1 C6 C7 0.1(3) . . . . ?
C2 C1 C6 C7 -179.93(16) . . . . ?
C15 C13 C12 C11 0.9(3) . . . . ?
C14 C13 C12 C11 179.1(2) . . . . ?
C13 C12 C11 C10 -1.9(3) . . . . ?
C13 C12 C11 N1 176.67(18) . . . . ?
C16 C10 C11 C12 1.8(3) . . . . ?
C4 C10 C11 C12 -177.87(18) . . . . ?
C16 C10 C11 N1 -176.66(17) . . . . ?
C4 C10 C11 N1 3.6(3) . . . . ?
O2 N1 C11 C12 -141.8(2) . . . . ?
O3 N1 C11 C12 36.8(3) . . . . ?
O2 N1 C11 C10 36.8(3) . . . . ?
O3 N1 C11 C10 -144.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.740
_diffrn_reflns_theta_full        26.63
_diffrn_measured_fraction_theta_full 0.740
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 986893'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3-methyl-2'-nitro-[1,1'-biphenyl]-4-ol

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'

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

_cell_length_a                   14.4397(11)
_cell_length_b                   10.6268(9)
_cell_length_c                   7.2172(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1107.46(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2244
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.83
_reflns_number_total             2244
_reflns_number_gt                1867
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.5041P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0126(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(18)
_refine_ls_number_reflns         2244
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05101(13) 1.24127(16) 0.8821(3) 0.0421(5) Uani 1 1 d . . .
H1 H 0.032(2) 1.254(3) 0.778(6) 0.063 Uiso 1 1 d . . .
O2 O -0.00855(12) 0.69790(18) 1.0075(3) 0.0447(5) Uani 1 1 d . . .
O3 O -0.00244(13) 0.56489(19) 0.7819(4) 0.0528(6) Uani 1 1 d . . .
N1 N 0.03513(13) 0.63173(19) 0.8986(4) 0.0356(5) Uani 1 1 d . . .
C1 C 0.08197(15) 1.1190(2) 0.8884(4) 0.0293(5) Uani 1 1 d . . .
C2 C 0.14585(15) 1.0887(2) 1.0258(3) 0.0277(5) Uani 1 1 d . . .
C3 C 0.17699(15) 0.9651(2) 1.0329(3) 0.0278(5) Uani 1 1 d . . .
H8 H 0.2204 0.9433 1.1226 0.033 Uiso 1 1 calc R . .
C4 C 0.14580(14) 0.8723(2) 0.9108(4) 0.0263(5) Uani 1 1 d . . .
C7 C 0.18607(15) 0.7437(2) 0.9179(3) 0.0269(5) Uani 1 1 d . . .
C12 C 0.28227(15) 0.7306(2) 0.9288(4) 0.0316(5) Uani 1 1 d . . .
H7 H 0.3187 0.8026 0.9362 0.038 Uiso 1 1 calc R . .
C11 C 0.32507(17) 0.6142(2) 0.9291(4) 0.0366(6) Uani 1 1 d . . .
H6 H 0.3892 0.6090 0.9392 0.044 Uiso 1 1 calc R . .
C10 C 0.27299(18) 0.5060(2) 0.9144(4) 0.0409(6) Uani 1 1 d . . .
H5 H 0.3019 0.4278 0.9125 0.049 Uiso 1 1 calc R . .
C9 C 0.17778(17) 0.5140(2) 0.9025(4) 0.0369(6) Uani 1 1 d . . .
H4 H 0.1419 0.4416 0.8925 0.044 Uiso 1 1 calc R . .
C8 C 0.13666(15) 0.6317(2) 0.9057(4) 0.0291(5) Uani 1 1 d . . .
C5 C 0.08176(15) 0.9067(2) 0.7756(4) 0.0293(5) Uani 1 1 d . . .
H3 H 0.0598 0.8465 0.6930 0.035 Uiso 1 1 calc R . .
C6 C 0.05055(16) 1.0290(2) 0.7629(4) 0.0305(5) Uani 1 1 d . . .
H2 H 0.0086 1.0514 0.6709 0.037 Uiso 1 1 calc R . .
C13 C 0.1793(2) 1.1851(3) 1.1612(4) 0.0419(7) Uani 1 1 d . . .
H11 H 0.2151 1.2476 1.0973 0.063 Uiso 1 1 calc R . .
H9 H 0.2171 1.1452 1.2535 0.063 Uiso 1 1 calc R . .
H10 H 0.1271 1.2245 1.2199 0.063 Uiso 1 1 calc R . .


_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 C1 1.375(3) . ?
O1 H1 0.81(4) . ?
O2 N1 1.229(3) . ?
O3 N1 1.228(3) . ?
N1 C8 1.467(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.393(4) . ?
C2 C3 1.389(3) . ?
C2 C13 1.496(3) . ?
C3 C4 1.398(3) . ?
C3 H8 0.9300 . ?
C4 C5 1.393(3) . ?
C4 C7 1.486(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.398(3) . ?
C12 C11 1.382(3) . ?
C12 H7 0.9300 . ?
C11 C10 1.378(4) . ?
C11 H6 0.9300 . ?
C10 C9 1.380(4) . ?
C10 H5 0.9300 . ?
C9 C8 1.385(3) . ?
C9 H4 0.9300 . ?
C5 C6 1.379(3) . ?
C5 H3 0.9300 . ?
C6 H2 0.9300 . ?
C13 H11 0.9600 . ?
C13 H9 0.9600 . ?
C13 H10 0.9600 . ?

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
C1 O1 H1 107(2) . . ?
O3 N1 O2 122.9(2) . . ?
O3 N1 C8 117.7(2) . . ?
O2 N1 C8 119.4(2) . . ?
O1 C1 C2 117.2(2) . . ?
O1 C1 C6 121.4(2) . . ?
C2 C1 C6 121.3(2) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 C13 121.3(2) . . ?
C1 C2 C13 121.4(2) . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H8 118.7 . . ?
C4 C3 H8 118.7 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 C7 121.7(2) . . ?
C3 C4 C7 120.1(2) . . ?
C8 C7 C12 115.3(2) . . ?
C8 C7 C4 125.74(19) . . ?
C12 C7 C4 118.85(19) . . ?
C11 C12 C7 122.2(2) . . ?
C11 C12 H7 118.9 . . ?
C7 C12 H7 118.9 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H6 119.9 . . ?
C12 C11 H6 119.9 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H5 120.1 . . ?
C9 C10 H5 120.1 . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H4 120.6 . . ?
C8 C9 H4 120.6 . . ?
C9 C8 C7 123.7(2) . . ?
C9 C8 N1 115.3(2) . . ?
C7 C8 N1 121.00(19) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H3 119.7 . . ?
C4 C5 H3 119.7 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H2 120.1 . . ?
C1 C6 H2 120.1 . . ?
C2 C13 H11 109.5 . . ?
C2 C13 H9 109.5 . . ?
H11 C13 H9 109.5 . . ?
C2 C13 H10 109.5 . . ?
H11 C13 H10 109.5 . . ?
H9 C13 H10 109.5 . . ?

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 C1 C2 C3 179.8(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
O1 C1 C2 C13 0.1(4) . . . . ?
C6 C1 C2 C13 -179.7(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C13 C2 C3 C4 178.7(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C2 C3 C4 C7 176.2(2) . . . . ?
C5 C4 C7 C8 -47.5(4) . . . . ?
C3 C4 C7 C8 137.4(3) . . . . ?
C5 C4 C7 C12 129.3(2) . . . . ?
C3 C4 C7 C12 -45.9(3) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
C4 C7 C12 C11 -177.6(2) . . . . ?
C7 C12 C11 C10 1.3(4) . . . . ?
C12 C11 C10 C9 -1.1(5) . . . . ?
C11 C10 C9 C8 0.0(5) . . . . ?
C10 C9 C8 C7 0.9(5) . . . . ?
C10 C9 C8 N1 -178.1(3) . . . . ?
C12 C7 C8 C9 -0.6(4) . . . . ?
C4 C7 C8 C9 176.2(3) . . . . ?
C12 C7 C8 N1 178.3(2) . . . . ?
C4 C7 C8 N1 -4.9(4) . . . . ?
O3 N1 C8 C9 -47.2(4) . . . . ?
O2 N1 C8 C9 133.1(3) . . . . ?
O3 N1 C8 C7 133.8(3) . . . . ?
O2 N1 C8 C7 -45.9(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C7 C4 C5 C6 -175.1(2) . . . . ?
C4 C5 C6 C1 -1.1(4) . . . . ?
O1 C1 C6 C5 -178.8(2) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.83
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 986891'
