# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_sp014_0m
_database_code_depnum_ccdc_archive 'CCDC 1879457'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2018-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 methyl (2-aminophenyl)carbamate
;
_chemical_formula_moiety         'C8 H8 N2 O2'
_chemical_formula_sum            'C8 H8 N2 O2'
_chemical_formula_weight         164.16
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6784(3)
_cell_length_b                   10.7811(4)
_cell_length_c                   9.5685(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.899(2)
_cell_angle_gamma                90
_cell_volume                     784.58(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5682
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      34.76
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.45
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16283
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.441
_diffrn_reflns_theta_min         2.862
_diffrn_ambient_temperature      169.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2733
_reflns_number_total             3666
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker Saint'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²+0.0864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Sof(H1D)=Sof(H1E)=Sof(H1F)=1-FVAR(1)
 Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
3.a Disordered Me refined as rotating group:
 C1(H1A,H1B,H1C,H1D,H1E,H1F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 O 0.15140(10) 0.71293(6) 0.30035(6) 0.03159(16) Uani 1 1 d . . . . .
N1 N 0.20864(9) 0.66163(6) 0.53338(6) 0.02059(13) Uani 1 1 d . . . . .
O2 O 0.51878(11) 0.50366(8) 0.84501(7) 0.04071(19) Uani 1 1 d . . . . .
N2 N 0.42663(10) 0.55581(8) 0.74766(7) 0.02791(16) Uani 1 1 d . . . . .
C3 C 0.25021(9) 0.53602(7) 0.52079(7) 0.01896(13) Uani 1 1 d . . . . .
C2 C 0.16014(10) 0.74207(7) 0.42504(7) 0.02136(15) Uani 1 1 d . . . . .
C4 C 0.35818(10) 0.47760(7) 0.63265(8) 0.02113(14) Uani 1 1 d . . . . .
C8 C 0.18384(11) 0.46434(8) 0.40375(8) 0.02464(16) Uani 1 1 d . . . . .
C5 C 0.39976(11) 0.35147(8) 0.62709(10) 0.02752(17) Uani 1 1 d . . . . .
C1 C 0.11756(13) 0.87085(8) 0.47011(9) 0.02849(17) Uani 1 1 d . . . . .
H1A H 0.2069 0.9288 0.4455 0.034 Uiso 0.498(14) 1 calc GR . P . .
H1B H 0.1162 0.8723 0.5724 0.034 Uiso 0.498(14) 1 calc GR . P . .
H1C H 0.0018 0.8954 0.4218 0.034 Uiso 0.498(14) 1 calc GR . P . .
H1D H 0.0098 0.8689 0.5143 0.034 Uiso 0.502(14) 1 calc GR . P . .
H1E H 0.1004 0.9254 0.3875 0.034 Uiso 0.502(14) 1 calc GR . P . .
H1F H 0.2148 0.9022 0.5380 0.034 Uiso 0.502(14) 1 calc GR . P . .
C7 C 0.22653(12) 0.33967(8) 0.39984(10) 0.02977(18) Uani 1 1 d . . . . .
C6 C 0.33496(12) 0.28243(8) 0.51048(11) 0.03144(19) Uani 1 1 d . . . . .
H1 H 0.2154(16) 0.6915(12) 0.6201(13) 0.032(3) Uiso 1 1 d . . . . .
H8 H 0.1045(17) 0.5032(12) 0.3269(13) 0.036(3) Uiso 1 1 d . . . . .
H7 H 0.1779(19) 0.2919(14) 0.3173(15) 0.045(4) Uiso 1 1 d . . . . .
H6 H 0.3603(19) 0.1993(15) 0.5024(15) 0.043(4) Uiso 1 1 d . . . . .
H5 H 0.4817(17) 0.3179(13) 0.7066(13) 0.037(3) Uiso 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 C2 1.2266(9) . ?
N1 C3 1.4004(10) . ?
N1 C2 1.3635(9) . ?
N1 H1 0.885(13) . ?
O2 N2 1.2261(9) . ?
N2 C4 1.4280(10) . ?
C3 C4 1.4091(10) . ?
C3 C8 1.3979(10) . ?
C2 C1 1.5031(11) . ?
C4 C5 1.3995(11) . ?
C8 C7 1.3852(12) . ?
C8 H8 0.982(13) . ?
C5 C6 1.3763(13) . ?
C5 H5 0.987(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C1 H1F 0.9800 . ?
C7 C6 1.3973(14) . ?
C7 H7 0.974(15) . ?
C6 H6 0.922(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
C3 N1 H1 116.6(8) . . ?
C2 N1 C3 126.25(6) . . ?
C2 N1 H1 117.1(8) . . ?
O2 N2 C4 115.32(8) . . ?
N1 C3 C4 118.96(6) . . ?
C8 C3 N1 122.76(6) . . ?
C8 C3 C4 118.24(7) . . ?
O1 C2 N1 123.32(7) . . ?
O1 C2 C1 122.05(7) . . ?
N1 C2 C1 114.63(6) . . ?
C3 C4 N2 115.93(7) . . ?
C5 C4 N2 122.77(7) . . ?
C5 C4 C3 121.26(7) . . ?
C3 C8 H8 119.0(8) . . ?
C7 C8 C3 119.76(7) . . ?
C7 C8 H8 121.2(8) . . ?
C4 C5 H5 116.9(8) . . ?
C6 C5 C4 119.82(8) . . ?
C6 C5 H5 123.2(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
C2 C1 H1E 109.5 . . ?
C2 C1 H1F 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1A C1 H1D 141.1 . . ?
H1A C1 H1E 56.3 . . ?
H1A C1 H1F 56.3 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1D 56.3 . . ?
H1B C1 H1E 141.1 . . ?
H1B C1 H1F 56.3 . . ?
H1C C1 H1D 56.3 . . ?
H1C C1 H1E 56.3 . . ?
H1C C1 H1F 141.1 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
C8 C7 C6 121.78(8) . . ?
C8 C7 H7 118.0(9) . . ?
C6 C7 H7 120.2(9) . . ?
C5 C6 C7 119.13(8) . . ?
C5 C6 H6 122.4(9) . . ?
C7 C6 H6 118.4(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B O1 0.98 2.35 3.2623(10) 154.9 4_576
C1 H1F O2 0.98 2.45 3.4086(12) 165.7 2_656
N1 H1 O1 0.885(13) 2.124(13) 2.9760(9) 161.4(11) 4_576
C8 H8 O1 0.982(13) 2.309(13) 2.8558(11) 114.2(10) .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sp159_0m
_database_code_depnum_ccdc_archive 'CCDC 2003805'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2019-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        1-(hydroxyimino)naphthalen-2(1H)-one
_chemical_formula_moiety         'C10 H7 N O2'
_chemical_formula_sum            'C10 H7 N O2'
_chemical_formula_weight         173.17
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.4498(9)
_cell_length_b                   9.1487(16)
_cell_length_c                   15.499(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.193(3)
_cell_angle_gamma                90
_cell_volume                     764.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3327
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.22
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14400
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.486
_diffrn_reflns_theta_min         2.655
_diffrn_ambient_temperature      150.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2502
_reflns_number_total             3666
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0828P)²+0.1045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1497
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O2 O 0.28680(15) 0.90859(9) 0.43925(5) 0.02823(18) Uani 1 1 d . . . . .
O1 O 0.64263(17) 0.79591(10) 0.37838(5) 0.0305(2) Uani 1 1 d . . . . .
N1 N 0.69440(17) 0.71278(10) 0.45157(6) 0.02398(18) Uani 1 1 d . . . . .
C6 C 0.60733(16) 0.63481(10) 0.58957(5) 0.01637(16) Uani 1 1 d . . . . .
C2 C 0.34041(17) 0.83117(10) 0.50574(6) 0.01930(17) Uani 1 1 d . . . . .
C4 C 0.26515(17) 0.75673(11) 0.65001(6) 0.01923(17) Uani 1 1 d . . . . .
C10 C 0.51988(18) 0.56667(11) 0.73361(6) 0.02036(18) Uani 1 1 d . . . . .
C1 C 0.55014(16) 0.72692(10) 0.51181(6) 0.01786(17) Uani 1 1 d . . . . .
C5 C 0.46545(15) 0.65126(10) 0.65791(6) 0.01610(16) Uani 1 1 d . . . . .
C7 C 0.79827(17) 0.53137(11) 0.59825(6) 0.02156(19) Uani 1 1 d . . . . .
C9 C 0.71053(18) 0.46574(11) 0.74131(6) 0.02257(19) Uani 1 1 d . . . . .
C3 C 0.20459(17) 0.84197(11) 0.57916(6) 0.02070(18) Uani 1 1 d . . . . .
C8 C 0.84896(18) 0.44758(12) 0.67299(7) 0.0236(2) Uani 1 1 d . . . . .
H4 H 0.173(2) 0.7626(16) 0.7014(9) 0.023(3) Uiso 1 1 d . . . . .
H10 H 0.423(3) 0.5813(15) 0.7828(9) 0.027(3) Uiso 1 1 d . . . . .
H9 H 0.746(3) 0.4054(17) 0.7931(10) 0.030(4) Uiso 1 1 d . . . . .
H8 H 0.983(3) 0.3760(17) 0.6776(9) 0.031(4) Uiso 1 1 d . . . . .
H7 H 0.898(3) 0.5159(17) 0.5498(10) 0.034(4) Uiso 1 1 d . . . . .
H3 H 0.070(3) 0.9133(17) 0.5757(10) 0.034(4) Uiso 1 1 d . . . . .
H1 H 0.507(4) 0.848(2) 0.3860(13) 0.060(6) Uiso 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
O2 C2 1.2502(12) . ?
O1 N1 1.3614(12) . ?
O1 H1 0.90(2) . ?
N1 C1 1.3099(12) . ?
C6 C1 1.4672(13) . ?
C6 C5 1.4056(12) . ?
C6 C7 1.3988(13) . ?
C2 C1 1.4814(14) . ?
C2 C3 1.4467(13) . ?
C4 C5 1.4490(13) . ?
C4 C3 1.3489(14) . ?
C4 H4 1.001(13) . ?
C10 C5 1.4016(13) . ?
C10 C9 1.3824(14) . ?
C10 H10 0.994(14) . ?
C7 C8 1.3837(14) . ?
C7 H7 1.000(15) . ?
C9 C8 1.3948(14) . ?
C9 H9 0.971(15) . ?
C3 H3 0.976(16) . ?
C8 H8 0.976(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
N1 O1 H1 105.1(13) . . ?
C1 N1 O1 117.68(9) . . ?
C5 C6 C1 118.83(8) . . ?
C7 C6 C1 122.39(8) . . ?
C7 C6 C5 118.79(8) . . ?
O2 C2 C1 120.31(8) . . ?
O2 C2 C3 121.60(9) . . ?
C3 C2 C1 118.08(8) . . ?
C5 C4 H4 115.1(8) . . ?
C3 C4 C5 123.21(8) . . ?
C3 C4 H4 121.7(8) . . ?
C5 C10 H10 119.7(8) . . ?
C9 C10 C5 120.52(8) . . ?
C9 C10 H10 119.8(8) . . ?
N1 C1 C6 116.74(8) . . ?
N1 C1 C2 123.67(9) . . ?
C6 C1 C2 119.58(8) . . ?
C6 C5 C4 119.76(8) . . ?
C10 C5 C6 119.88(8) . . ?
C10 C5 C4 120.36(8) . . ?
C6 C7 H7 120.1(9) . . ?
C8 C7 C6 120.82(8) . . ?
C8 C7 H7 119.1(9) . . ?
C10 C9 C8 119.68(9) . . ?
C10 C9 H9 120.5(9) . . ?
C8 C9 H9 119.8(9) . . ?
C2 C3 H3 117.8(9) . . ?
C4 C3 C2 120.50(9) . . ?
C4 C3 H3 121.7(9) . . ?
C7 C8 C9 120.30(9) . . ?
C7 C8 H8 119.4(9) . . ?
C9 C8 H8 120.3(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.90(2) 1.65(2) 2.4970(12) 156.2(19) .

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_sp101a_0m
_database_code_depnum_ccdc_archive 'CCDC 2003802'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2019-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            trans-o,o'-azodioxytoluene
_chemical_name_systematic        '1, 2-bis(2mehtylphenyl)diazene 1,2-dioxide'
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.1552(6)
_cell_length_b                   10.3206(8)
_cell_length_c                   14.3800(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1210.32(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1488
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8241
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.387
_diffrn_reflns_theta_min         2.833
_diffrn_ambient_temperature      104.71
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1240
_reflns_number_total             1907
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+0.2615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 O 0.68825(13) 0.52221(11) 0.54964(8) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.54384(15) 0.48086(11) 0.53601(8) 0.0151(3) Uani 1 1 d . . . . .
C1 C 0.46730(16) 0.39346(13) 0.60227(9) 0.0145(3) Uani 1 1 d . . . . .
C6 C 0.41967(18) 0.44656(14) 0.68639(10) 0.0176(3) Uani 1 1 d . . . . .
C3 C 0.38796(19) 0.18413(15) 0.65072(10) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.45378(16) 0.26251(13) 0.58122(9) 0.0149(3) Uani 1 1 d . . . . .
C5 C 0.35226(18) 0.36616(16) 0.75334(10) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.33714(18) 0.23494(15) 0.73519(11) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.5050(2) 0.20877(16) 0.48853(11) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.287(2) 0.1785(18) 0.7807(13) 0.029(5) Uiso 1 1 d . . . . .
H6 H 0.431(2) 0.5354(16) 0.6968(11) 0.017(4) Uiso 1 1 d . . . . .
H3 H 0.378(2) 0.0926(17) 0.6384(11) 0.021(4) Uiso 1 1 d . . . . .
H5 H 0.318(2) 0.4008(19) 0.8113(14) 0.034(5) Uiso 1 1 d . . . . .
H7A H 0.474(3) 0.117(3) 0.4828(16) 0.070(8) Uiso 1 1 d . . . . .
H7B H 0.454(3) 0.248(2) 0.4377(18) 0.066(8) Uiso 1 1 d . . . . .
H7C H 0.620(4) 0.215(2) 0.4782(18) 0.072(8) Uiso 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 N1 1.2679(16) . ?
N1 N1 1.319(2) 5_666 ?
N1 C1 1.4529(17) . ?
C1 C6 1.3837(19) . ?
C1 C2 1.3893(19) . ?
C6 C5 1.385(2) . ?
C6 H6 0.933(17) . ?
C3 C2 1.393(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.965(17) . ?
C2 C7 1.503(2) . ?
C5 C4 1.385(2) . ?
C5 H5 0.950(19) . ?
C4 H4 0.967(18) . ?
C7 H7A 0.98(3) . ?
C7 H7B 0.93(3) . ?
C7 H7C 0.95(3) . ?

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
O1 N1 N1 121.61(15) . 5_666 ?
O1 N1 C1 120.44(11) . . ?
N1 N1 C1 117.90(14) 5_666 . ?
C6 C1 N1 116.61(12) . . ?
C6 C1 C2 123.60(13) . . ?
C2 C1 N1 119.68(12) . . ?
C1 C6 C5 118.81(14) . . ?
C1 C6 H6 120.0(10) . . ?
C5 C6 H6 121.2(10) . . ?
C2 C3 H3 118.0(10) . . ?
C4 C3 C2 121.60(14) . . ?
C4 C3 H3 120.4(10) . . ?
C1 C2 C3 116.05(13) . . ?
C1 C2 C7 122.01(13) . . ?
C3 C2 C7 121.94(13) . . ?
C6 C5 H5 120.2(12) . . ?
C4 C5 C6 119.36(14) . . ?
C4 C5 H5 120.5(12) . . ?
C3 C4 H4 119.4(11) . . ?
C5 C4 C3 120.56(14) . . ?
C5 C4 H4 120.0(11) . . ?
C2 C7 H7A 110.9(14) . . ?
C2 C7 H7B 114.2(15) . . ?
C2 C7 H7C 112.8(15) . . ?
H7A C7 H7B 104(2) . . ?
H7A C7 H7C 108.0(19) . . ?
H7B C7 H7C 107(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_sp101e_pl
_database_code_depnum_ccdc_archive 'CCDC 2003804'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2019-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            cis-o,o'-azodioxytoluene
_chemical_name_systematic        'Z-1, 2-bis(2-methylphenyl)diazene 1,2-dioxide'
_chemical_formula_moiety         'C14 H14 N2 O2'
_chemical_formula_sum            'C14 H14 N2 O2'
_chemical_formula_weight         242.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.1760(13)
_cell_length_b                   10.4211(6)
_cell_length_c                   15.5264(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.000(7)
_cell_angle_gamma                90
_cell_volume                     2455.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3012
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.91
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.45
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_av_unetI/netI     0.1671
_diffrn_reflns_Laue_measured_fraction_full 0.821
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15757
_diffrn_reflns_point_group_measured_fraction_full 0.821
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.603
_diffrn_reflns_theta_min         2.624
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.821
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1655
_reflns_number_total             3330
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      0.826
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1121
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C10(H10), C13(H13), C5(H5), C6(H6), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C7(H7a,H7b,H7c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 O -0.09590(9) -0.21513(12) -0.34684(8) 0.0217(3) Uani 1 1 d . . . . .
O2 O -0.00324(8) -0.22961(12) -0.20941(8) 0.0222(3) Uani 1 1 d . . . . .
N2 N -0.06604(10) -0.14964(14) -0.21288(9) 0.0153(3) Uani 1 1 d . . . . .
N1 N -0.11461(9) -0.14293(14) -0.28358(9) 0.0150(3) Uani 1 1 d . . . . .
C9 C -0.12000(11) -0.13133(17) -0.06582(11) 0.0149(4) Uani 1 1 d . . . . .
C8 C -0.08560(11) -0.06939(16) -0.13848(11) 0.0138(4) Uani 1 1 d . . . . .
C1 C -0.18717(11) -0.05328(16) -0.28979(11) 0.0153(4) Uani 1 1 d . . . . .
C11 C -0.11195(12) 0.07526(17) 0.00599(12) 0.0195(4) Uani 1 1 d . . . . .
H11 H -0.121547 0.125563 0.056151 0.023 Uiso 1 1 calc R . . . .
C12 C -0.07636(12) 0.13162(18) -0.06720(12) 0.0184(4) Uani 1 1 d . . . . .
H12 H -0.060917 0.219962 -0.066875 0.022 Uiso 1 1 calc R . . . .
C10 C -0.13356(12) -0.05401(17) 0.00628(12) 0.0178(4) Uani 1 1 d . . . . .
H10 H -0.158202 -0.090802 0.056815 0.021 Uiso 1 1 calc R . . . .
C2 C -0.18139(12) 0.04501(17) -0.35070(11) 0.0188(4) Uani 1 1 d . . . . .
C13 C -0.06345(11) 0.05880(17) -0.14054(11) 0.0156(4) Uani 1 1 d . . . . .
H13 H -0.039814 0.096349 -0.191280 0.019 Uiso 1 1 calc R . . . .
C5 C -0.33111(12) 0.01093(19) -0.24521(12) 0.0211(4) Uani 1 1 d . . . . .
H5 H -0.381989 -0.000980 -0.210475 0.025 Uiso 1 1 calc R . . . .
C6 C -0.26049(12) -0.07167(18) -0.23808(11) 0.0171(4) Uani 1 1 d . . . . .
H6 H -0.262098 -0.140577 -0.198054 0.021 Uiso 1 1 calc R . . . .
C14 C -0.14151(13) -0.27136(17) -0.06380(12) 0.0217(4) Uani 1 1 d . . . . .
H14A H -0.194118 -0.287468 -0.098778 0.032 Uiso 1 1 calc GR . . . .
H14B H -0.152695 -0.297939 -0.004252 0.032 Uiso 1 1 calc GR . . . .
H14C H -0.091824 -0.320424 -0.087054 0.032 Uiso 1 1 calc GR . . . .
C3 C -0.25394(14) 0.12711(19) -0.35563(13) 0.0257(4) Uani 1 1 d . . . . .
H3 H -0.253018 0.195705 -0.395917 0.031 Uiso 1 1 calc R . . . .
C4 C -0.32718(13) 0.1115(2) -0.30351(13) 0.0264(5) Uani 1 1 d . . . . .
H4 H -0.374995 0.169946 -0.307741 0.032 Uiso 1 1 calc R . . . .
C7 C -0.10223(13) 0.06432(18) -0.40738(12) 0.0237(4) Uani 1 1 d . . . . .
H7A H -0.048450 0.051863 -0.373461 0.035 Uiso 1 1 calc GR . . . .
H7B H -0.103000 0.151564 -0.430932 0.035 Uiso 1 1 calc GR . . . .
H7C H -0.103630 0.002141 -0.454708 0.035 Uiso 1 1 calc GR . . . .


_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 N1 1.2695(18) . ?
O2 N2 1.2671(18) . ?
N2 N1 1.3241(19) . ?
N2 C8 1.457(2) . ?
N1 C1 1.447(2) . ?
C9 C8 1.401(2) . ?
C9 C10 1.395(3) . ?
C9 C14 1.496(2) . ?
C8 C13 1.378(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.385(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C11 C10 1.387(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C10 H10 0.9500 . ?
C2 C3 1.397(3) . ?
C2 C7 1.503(3) . ?
C13 H13 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.379(3) . ?
C5 C4 1.386(3) . ?
C6 H6 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
O2 N2 N1 119.26(14) . . ?
O2 N2 C8 119.81(14) . . ?
N1 N2 C8 120.91(14) . . ?
O1 N1 N2 119.05(14) . . ?
O1 N1 C1 120.08(14) . . ?
N2 N1 C1 120.86(14) . . ?
C8 C9 C14 123.22(16) . . ?
C10 C9 C8 115.80(16) . . ?
C10 C9 C14 120.98(16) . . ?
C9 C8 N2 116.75(15) . . ?
C13 C8 N2 119.25(16) . . ?
C13 C8 C9 123.80(17) . . ?
C2 C1 N1 118.08(15) . . ?
C6 C1 N1 118.89(15) . . ?
C6 C1 C2 122.97(16) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.37(17) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.81(17) . . ?
C13 C12 H12 120.1 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.59(18) . . ?
C11 C10 H10 119.2 . . ?
C1 C2 C7 123.02(16) . . ?
C3 C2 C1 115.90(16) . . ?
C3 C2 C7 121.07(16) . . ?
C8 C13 C12 118.59(17) . . ?
C8 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.39(17) . . ?
C4 C5 H5 120.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.43(17) . . ?
C5 C6 H6 120.3 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.92(18) . . ?
C4 C3 H3 119.0 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.36(18) . . ?
C3 C4 H4 119.8 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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 N1 C1 C2 -63.6(2) . . . . ?
O1 N1 C1 C6 113.65(18) . . . . ?
O2 N2 N1 O1 -1.4(2) . . . . ?
O2 N2 N1 C1 179.68(15) . . . . ?
O2 N2 C8 C9 -68.8(2) . . . . ?
O2 N2 C8 C13 106.28(19) . . . . ?
N2 N1 C1 C2 115.29(18) . . . . ?
N2 N1 C1 C6 -67.4(2) . . . . ?
N2 C8 C13 C12 -175.23(16) . . . . ?
N1 N2 C8 C9 109.31(18) . . . . ?
N1 N2 C8 C13 -75.6(2) . . . . ?
N1 C1 C2 C3 178.51(16) . . . . ?
N1 C1 C2 C7 -2.3(3) . . . . ?
N1 C1 C6 C5 -178.12(16) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C8 N2 N1 O1 -179.47(15) . . . . ?
C8 N2 N1 C1 1.6(2) . . . . ?
C8 C9 C10 C11 -1.6(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C11 C12 C13 C8 -0.8(3) . . . . ?
C12 C11 C10 C9 0.4(3) . . . . ?
C10 C9 C8 N2 176.51(15) . . . . ?
C10 C9 C8 C13 1.7(2) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C1 C2 C7 -179.43(17) . . . . ?
C6 C5 C4 C3 1.5(3) . . . . ?
C14 C9 C8 N2 -3.5(2) . . . . ?
C14 C9 C8 C13 -178.32(16) . . . . ?
C14 C9 C10 C11 178.43(17) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C7 C2 C3 C4 -179.51(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sp157_0m
_database_code_depnum_ccdc_archive 'CCDC 2003803'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2019-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F4 N2 O2'
_chemical_formula_sum            'C12 H6 F4 N2 O2'
_chemical_formula_weight         286.19
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0409(7)
_cell_length_b                   7.1841(8)
_cell_length_c                   7.1860(9)
_cell_angle_alpha                61.943(7)
_cell_angle_beta                 65.010(7)
_cell_angle_gamma                64.427(7)
_cell_volume                     278.14(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1974
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.73
_cell_measurement_theta_min      3.34
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             144
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5012
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.959
_diffrn_reflns_theta_min         3.337
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1236
_reflns_number_total             1615
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0656
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1531P)²+0.0293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1965
_refine_ls_wR_factor_ref         0.2120
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1 F 0.6236(2) 0.36391(19) 0.6636(2) 0.0253(4) Uani 1 1 d . . . . .
F2 F 0.8503(2) 0.8757(2) 0.6839(2) 0.0299(4) Uani 1 1 d . . . . .
O1 O 1.0800(2) 0.3915(2) 0.7336(2) 0.0242(4) Uani 1 1 d . . . . .
N1 N 0.9628(3) 0.4982(3) 0.6021(3) 0.0174(4) Uani 1 1 d . . . . .
C1 C 0.7369(3) 0.6217(3) 0.6698(3) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.5685(3) 0.5498(3) 0.7017(3) 0.0175(4) Uani 1 1 d . . . . .
C6 C 0.6855(3) 0.8079(3) 0.7144(3) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.4709(3) 0.9244(3) 0.7853(3) 0.0215(5) Uani 1 1 d . . . . .
C3 C 0.3515(3) 0.6600(3) 0.7728(3) 0.0210(4) Uani 1 1 d . . . . .
C4 C 0.3059(3) 0.8486(3) 0.8126(3) 0.0226(5) Uani 1 1 d . . . . .
H5 H 0.440(4) 1.053(5) 0.819(4) 0.029(7) Uiso 1 1 d . . . . .
H4 H 0.147(5) 0.921(5) 0.855(5) 0.042(8) Uiso 1 1 d . . . . .
H3 H 0.229(5) 0.609(5) 0.794(5) 0.034(7) Uiso 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
F1 C2 1.348(2) . ?
F2 C6 1.343(2) . ?
O1 N1 1.262(2) . ?
N1 N1 1.325(3) 2_766 ?
N1 C1 1.444(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.383(3) . ?
C2 C3 1.378(3) . ?
C6 C5 1.379(3) . ?
C5 C4 1.392(3) . ?
C5 H5 0.97(3) . ?
C3 C4 1.390(3) . ?
C3 H3 1.01(3) . ?
C4 H4 0.98(3) . ?

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
O1 N1 N1 122.6(2) . 2_766 ?
O1 N1 C1 120.93(16) . . ?
N1 N1 C1 116.48(19) 2_766 . ?
C2 C1 N1 120.69(16) . . ?
C6 C1 N1 120.44(15) . . ?
C6 C1 C2 118.79(18) . . ?
F1 C2 C1 117.52(17) . . ?
F1 C2 C3 120.35(16) . . ?
C3 C2 C1 122.12(18) . . ?
F2 C6 C1 118.31(18) . . ?
F2 C6 C5 120.36(17) . . ?
C5 C6 C1 121.32(17) . . ?
C6 C5 C4 118.19(18) . . ?
C6 C5 H5 119.5(16) . . ?
C4 C5 H5 122.3(16) . . ?
C2 C3 C4 117.46(17) . . ?
C2 C3 H3 122.2(17) . . ?
C4 C3 H3 120.4(17) . . ?
C5 C4 H4 125.9(18) . . ?
C3 C4 C5 122.10(19) . . ?
C3 C4 H4 112.0(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sp081b_0m
_database_code_depnum_ccdc_archive 'CCDC 2003806'
loop_
_audit_author_name
_audit_author_address
'Colin Seaton'
;University of Bradford
United Kingdom
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
N-(2-nitrosophenyl)pivalamide
;
_chemical_formula_moiety         'C11 H14 N2 O3'
_chemical_formula_sum            'C11 H14 N2 O3'
_chemical_formula_weight         222.24
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6472(8)
_cell_length_b                   14.1772(19)
_cell_length_c                   14.2690(18)
_cell_angle_alpha                93.043(8)
_cell_angle_beta                 92.475(8)
_cell_angle_gamma                93.340(8)
_cell_volume                     1137.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.66
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0700 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.692
_diffrn_reflns_theta_min         1.973
_diffrn_ambient_temperature      100.11
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3643
_reflns_number_total             6932
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.0968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1386
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(N3)=Sof(O4)=1-FVAR(1)
 Sof(N2)=Sof(O3)=FVAR(1)
 Sof(N3A)=Sof(O3A)=1-FVAR(2)
 Sof(N2A)=Sof(O4A)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1(H1), C5A(H5A), C3(H3), C2A(H2A), C4A(H4A), C6(H6), C3A(H3A),
 C5(H5), C4(H4)
3.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C11A(H11A,H11B,H11C), C10(H10D,H10E,H10F), C9A(H9AA,
 H9AB,H9AC), C11(H11D,H11E,H11F), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1A O -0.1488(2) 0.17059(9) 0.82913(8) 0.0256(3) Uani 1 1 d . . . . .
O2A O -0.3055(2) 0.29741(9) 0.76272(8) 0.0315(3) Uani 1 1 d . . . . .
O1 O 0.7778(2) 0.39427(9) 0.18565(9) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.5950(2) 0.31578(9) 0.30006(8) 0.0302(3) Uani 1 1 d . . . . .
N1A N -0.0085(3) 0.21613(10) 0.69685(9) 0.0238(3) Uani 1 1 d . . . . .
H1A H 0.083765 0.169592 0.707584 0.029 Uiso 1 1 calc R . . . .
N1 N 0.9125(3) 0.25905(10) 0.22344(10) 0.0256(3) Uani 1 1 d . . . . .
H1 H 1.000806 0.270826 0.175605 0.031 Uiso 1 1 calc R . . . .
C7A C -0.1709(3) 0.23456(13) 0.76358(12) 0.0238(4) Uani 1 1 d . . . . .
C6A C 0.0274(3) 0.26208(12) 0.61453(11) 0.0223(4) Uani 1 1 d . . . . .
C1A C 0.2222(3) 0.23896(12) 0.56140(12) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.7439(3) 0.32277(12) 0.24267(12) 0.0230(4) Uani 1 1 d . . . . .
C5A C -0.1209(3) 0.33000(13) 0.58124(12) 0.0254(4) Uani 1 1 d . . . . .
H5A H -0.256405 0.345830 0.614563 0.031 Uiso 1 1 calc R . . . .
C1 C 1.1594(3) 0.12897(12) 0.24497(12) 0.0251(4) Uani 1 1 d . . . . .
C2 C 0.9600(3) 0.17861(12) 0.27026(11) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.8239(3) 0.14423(13) 0.34180(12) 0.0274(4) Uani 1 1 d . . . . .
H3 H 0.686369 0.175183 0.359275 0.033 Uiso 1 1 calc R . . . .
C8A C -0.2907(3) 0.17593(13) 0.91418(12) 0.0260(4) Uani 1 1 d . . . . .
C2A C 0.2717(3) 0.28522(14) 0.47963(12) 0.0293(4) Uani 1 1 d . . . . .
H2A H 0.405019 0.269291 0.444967 0.035 Uiso 1 1 calc R . . . .
C4A C -0.0693(3) 0.37382(13) 0.49986(12) 0.0291(4) Uani 1 1 d . . . . .
H4A H -0.171871 0.419333 0.477521 0.035 Uiso 1 1 calc R . . . .
C6 C 1.2220(3) 0.04970(13) 0.29300(13) 0.0307(4) Uani 1 1 d . . . . .
H6 H 1.358262 0.017590 0.276083 0.037 Uiso 1 1 calc R . . . .
C3A C 0.1295(3) 0.35308(14) 0.44946(12) 0.0314(4) Uani 1 1 d . . . . .
H3A H 0.165142 0.385784 0.394900 0.038 Uiso 1 1 calc R . . . .
C8 C 0.6321(3) 0.47847(13) 0.19341(14) 0.0300(4) Uani 1 1 d . . . . .
C5 C 1.0881(4) 0.01816(13) 0.36424(13) 0.0328(5) Uani 1 1 d . . . . .
H5 H 1.131159 -0.035135 0.397337 0.039 Uiso 1 1 calc R . . . .
C10A C -0.2262(4) 0.26860(14) 0.96973(13) 0.0339(5) Uani 1 1 d . . . . .
H10A H -0.053725 0.275736 0.981784 0.051 Uiso 1 1 calc GR . . . .
H10B H -0.304826 0.268777 1.029631 0.051 Uiso 1 1 calc GR . . . .
H10C H -0.278253 0.321225 0.933721 0.051 Uiso 1 1 calc GR . . . .
C4 C 0.8881(4) 0.06565(13) 0.38711(12) 0.0317(4) Uani 1 1 d . . . . .
H4 H 0.792837 0.043181 0.435477 0.038 Uiso 1 1 calc R . . . .
C11A C -0.2088(4) 0.09254(14) 0.96746(13) 0.0359(5) Uani 1 1 d . . . . .
H11A H -0.246164 0.033722 0.929113 0.054 Uiso 1 1 calc GR . . . .
H11B H -0.290547 0.089688 1.026538 0.054 Uiso 1 1 calc GR . . . .
H11C H -0.036982 0.100540 0.981027 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.3759(3) 0.44966(15) 0.16795(14) 0.0369(5) Uani 1 1 d . . . . .
H10D H 0.363587 0.415504 0.106229 0.055 Uiso 1 1 calc GR . . . .
H10E H 0.284392 0.506214 0.165841 0.055 Uiso 1 1 calc GR . . . .
H10F H 0.312804 0.408483 0.215191 0.055 Uiso 1 1 calc GR . . . .
C9A C -0.5531(3) 0.16255(15) 0.88649(14) 0.0362(5) Uani 1 1 d . . . . .
H9AA H -0.600935 0.215893 0.850577 0.054 Uiso 1 1 calc GR . . . .
H9AB H -0.644609 0.159589 0.943177 0.054 Uiso 1 1 calc GR . . . .
H9AC H -0.583409 0.103528 0.847800 0.054 Uiso 1 1 calc GR . . . .
C11 C 0.6682(4) 0.52436(15) 0.29182(16) 0.0518(7) Uani 1 1 d . . . . .
H11D H 0.587499 0.484537 0.336201 0.078 Uiso 1 1 calc GR . . . .
H11E H 0.602106 0.586789 0.293636 0.078 Uiso 1 1 calc GR . . . .
H11F H 0.838356 0.531399 0.309220 0.078 Uiso 1 1 calc GR . . . .
C9 C 0.7393(4) 0.54102(16) 0.12170(18) 0.0540(7) Uani 1 1 d . . . . .
H9A H 0.903344 0.561096 0.141993 0.081 Uiso 1 1 calc GR . . . .
H9B H 0.646342 0.596843 0.115886 0.081 Uiso 1 1 calc GR . . . .
H9C H 0.737672 0.505660 0.060741 0.081 Uiso 1 1 calc GR . . . .
N2A N 0.3526(5) 0.1654(3) 0.5977(3) 0.0277(8) Uani 0.766(5) 1 d . . P A 1
O4A O 0.5191(4) 0.14161(14) 0.54887(13) 0.0338(6) Uani 0.766(5) 1 d . . P A 1
N2 N 1.283(3) 0.1649(14) 0.1742(10) 0.056(4) Uani 0.564(7) 1 d . . P B 1
O3 O 1.2863(5) 0.2142(2) 0.1240(2) 0.0292(9) Uani 0.564(7) 1 d . . P B 1
N3 N 1.325(3) 0.1469(10) 0.1696(9) 0.025(2) Uani 0.436(7) 1 d . . P B 2
O4 O 1.4520(10) 0.1286(3) 0.1478(3) 0.0426(13) Uani 0.436(7) 1 d . . P B 2
N3A N 0.412(2) 0.1738(10) 0.5760(8) 0.028(3) Uiso 0.234(5) 1 d . . P A 2
O3A O 0.3860(11) 0.1290(5) 0.6491(5) 0.035(2) Uani 0.234(5) 1 d . . P A 2


_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
O1A C7A 1.344(2) . ?
O1A C8A 1.484(2) . ?
O2A C7A 1.205(2) . ?
O1 C7 1.343(2) . ?
O1 C8 1.491(2) . ?
O2 C7 1.202(2) . ?
N1A C7A 1.376(2) . ?
N1A C6A 1.390(2) . ?
N1 C7 1.376(2) . ?
N1 C2 1.386(2) . ?
C6A C1A 1.407(2) . ?
C6A C5A 1.401(2) . ?
C1A C2A 1.399(2) . ?
C1A N2A 1.419(4) . ?
C1A N3A 1.470(15) . ?
C5A C4A 1.380(2) . ?
C1 C2 1.412(2) . ?
C1 C6 1.402(2) . ?
C1 N2 1.356(14) . ?
C1 N3 1.477(13) . ?
C2 C3 1.396(2) . ?
C3 C4 1.376(2) . ?
C8A C10A 1.515(3) . ?
C8A C11A 1.523(3) . ?
C8A C9A 1.516(3) . ?
C2A C3A 1.364(3) . ?
C4A C3A 1.396(3) . ?
C6 C5 1.371(3) . ?
C8 C10 1.504(3) . ?
C8 C11 1.516(3) . ?
C8 C9 1.512(3) . ?
C5 C4 1.390(3) . ?
N2A O4A 1.245(3) . ?
N2 O3 1.028(17) . ?
N3 O4 0.845(14) . ?
N3A O3A 1.259(12) . ?

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
C7A O1A C8A 120.25(13) . . ?
C7 O1 C8 120.41(14) . . ?
C7A N1A C6A 127.88(15) . . ?
C7 N1 C2 127.89(15) . . ?
O1A C7A N1A 107.44(14) . . ?
O2A C7A O1A 127.03(16) . . ?
O2A C7A N1A 125.53(16) . . ?
N1A C6A C1A 118.41(15) . . ?
N1A C6A C5A 123.48(16) . . ?
C5A C6A C1A 118.11(16) . . ?
C6A C1A N2A 113.8(2) . . ?
C6A C1A N3A 132.4(5) . . ?
C2A C1A C6A 120.90(17) . . ?
C2A C1A N2A 125.2(2) . . ?
C2A C1A N3A 106.6(5) . . ?
O1 C7 N1 107.14(14) . . ?
O2 C7 O1 126.54(17) . . ?
O2 C7 N1 126.31(16) . . ?
C4A C5A C6A 119.76(17) . . ?
C2 C1 N3 129.0(5) . . ?
C6 C1 C2 120.56(17) . . ?
C6 C1 N3 110.4(5) . . ?
N2 C1 C2 115.3(9) . . ?
N2 C1 C6 124.1(9) . . ?
N1 C2 C1 118.20(15) . . ?
N1 C2 C3 123.85(16) . . ?
C3 C2 C1 117.95(16) . . ?
C4 C3 C2 120.23(17) . . ?
O1A C8A C10A 109.48(14) . . ?
O1A C8A C11A 102.29(14) . . ?
O1A C8A C9A 109.99(14) . . ?
C10A C8A C11A 110.91(15) . . ?
C10A C8A C9A 112.87(16) . . ?
C9A C8A C11A 110.79(16) . . ?
C3A C2A C1A 120.31(17) . . ?
C5A C4A C3A 121.77(17) . . ?
C5 C6 C1 120.48(18) . . ?
C2A C3A C4A 119.08(17) . . ?
O1 C8 C10 109.89(15) . . ?
O1 C8 C11 109.04(14) . . ?
O1 C8 C9 101.99(15) . . ?
C10 C8 C11 112.62(18) . . ?
C10 C8 C9 111.58(16) . . ?
C9 C8 C11 111.18(19) . . ?
C6 C5 C4 118.75(18) . . ?
C3 C4 C5 121.99(18) . . ?
O4A N2A C1A 114.3(4) . . ?
O3 N2 C1 145.1(17) . . ?
O4 N3 C1 141.6(12) . . ?
O3A N3A C1A 111.9(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O3A 0.88 2.03 2.705(6) 132.5 . yes
N1 H1 O3 0.88 1.99 2.682(3) 134.1 . yes
C5A H5A O2A 0.95 2.28 2.883(2) 120.6 . yes
C3 H3 O2 0.95 2.28 2.897(2) 121.7 . yes

_olex2_submission_special_instructions 'No special instructions were received'

