# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

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

data_2-4-Nitrophenylquinoxaline
_database_code_depnum_ccdc_archive 'CCDC 1506177'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_publcif_datablock.id            {434d6885-0acc-4fdb-8c31-148438362a6b}

_audit_creation_date             2016-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 N3 O2'
_chemical_formula_sum            'C14 H9 N3 O2'
_chemical_formula_weight         251.24
_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      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                   6.3758(4)
_cell_length_b                   12.4522(7)
_cell_length_c                   14.7628(10)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 79.702(6)
_cell_angle_gamma                90.000(5)
_cell_volume                     1153.18(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.9400
_cell_measurement_theta_min      3.5550
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.998
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15229
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.272
_diffrn_reflns_theta_min         3.247
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1405
_reflns_number_total             2853
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0055(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2853
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1536
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.045
_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)+(0.0438P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.0814(3) 0.23752(18) -0.10178(14) 0.0882(7) Uani 1 1 d . . . . .
O2 O 0.9951(3) 0.07137(19) -0.08890(16) 0.1110(9) Uani 1 1 d . . . . .
N1 N 0.9568(3) 0.1661(2) -0.07416(14) 0.0670(7) Uani 1 1 d . . . . .
N2 N 0.0644(3) 0.37378(15) 0.11122(12) 0.0490(5) Uani 1 1 d . . . . .
N3 N -0.1811(3) 0.22869(16) 0.23247(14) 0.0631(6) Uani 1 1 d . . . . .
C1 C 0.7464(3) 0.1950(2) -0.02172(16) 0.0517(6) Uani 1 1 d . . . . .
C2 C 0.6741(4) 0.2975(2) -0.02602(16) 0.0574(7) Uani 1 1 d . . . . .
H2 H 0.757823 0.349301 -0.060662 0.069 Uiso 1 1 calc R . . . .
C3 C 0.4748(3) 0.32283(19) 0.02182(16) 0.0548(7) Uani 1 1 d . . . . .
H3 H 0.423301 0.392342 0.018763 0.066 Uiso 1 1 calc R . . . .
C4 C 0.3496(3) 0.24653(18) 0.07450(14) 0.0445(6) Uani 1 1 d . . . . .
C5 C 0.4294(4) 0.1442(2) 0.07787(17) 0.0659(8) Uani 1 1 d . . . . .
H5 H 0.347974 0.092199 0.113261 0.079 Uiso 1 1 calc R . . . .
C6 C 0.6284(4) 0.1177(2) 0.02953(18) 0.0694(8) Uani 1 1 d . . . . .
H6 H 0.681089 0.048298 0.031856 0.083 Uiso 1 1 calc R . . . .
C7 C 0.1346(3) 0.27703(18) 0.12528(15) 0.0452(6) Uani 1 1 d . . . . .
C8 C 0.0083(4) 0.2056(2) 0.18667(17) 0.0608(7) Uani 1 1 d . . . . .
H8 H 0.063569 0.137977 0.194986 0.073 Uiso 1 1 calc R . . . .
C9 C -0.1323(3) 0.40106(17) 0.15796(15) 0.0463(6) Uani 1 1 d . . . . .
C10 C -0.2160(4) 0.50295(19) 0.14410(18) 0.0650(8) Uani 1 1 d . . . . .
H10 H -0.136418 0.551419 0.103963 0.078 Uiso 1 1 calc R . . . .
C11 C -0.4137(4) 0.5307(2) 0.18942(18) 0.0676(8) Uani 1 1 d . . . . .
H11 H -0.468069 0.598305 0.180091 0.081 Uiso 1 1 calc R . . . .
C12 C -0.5358(4) 0.4589(2) 0.24971(17) 0.0612(7) Uani 1 1 d . . . . .
H12 H -0.670631 0.478996 0.279974 0.073 Uiso 1 1 calc R . . . .
C13 C -0.4597(3) 0.3602(2) 0.26455(16) 0.0565(7) Uani 1 1 d . . . . .
H13 H -0.541838 0.313207 0.305273 0.068 Uiso 1 1 calc R . . . .
C14 C -0.2561(3) 0.32851(19) 0.21834(15) 0.0458(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.213(3) . ?
O2 N1 1.216(3) . ?
N1 C1 1.469(3) . ?
N2 C7 1.315(3) . ?
N2 C9 1.362(3) . ?
N3 C8 1.307(3) . ?
N3 C14 1.361(3) . ?
C1 C2 1.362(3) . ?
C1 C6 1.364(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 C5 1.376(3) . ?
C4 C7 1.489(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.413(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.406(3) . ?
C9 C14 1.407(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.362(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.353(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.411(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 O2 123.5(2) . . ?
O1 N1 C1 118.6(2) . . ?
O2 N1 C1 117.9(2) . . ?
C7 N2 C9 117.26(19) . . ?
C8 N3 C14 116.06(19) . . ?
C2 C1 N1 119.4(2) . . ?
C2 C1 C6 121.9(2) . . ?
C6 C1 N1 118.6(2) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 119.6(2) . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C7 122.1(2) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N2 C7 C4 117.62(19) . . ?
N2 C7 C8 120.4(2) . . ?
C8 C7 C4 122.0(2) . . ?
N3 C8 C7 124.1(2) . . ?
N3 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N2 C9 C10 119.4(2) . . ?
N2 C9 C14 121.4(2) . . ?
C10 C9 C14 119.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
N3 C14 C9 120.69(19) . . ?
N3 C14 C13 120.0(2) . . ?
C9 C14 C13 119.3(2) . . ?

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 17.5(4) . . . . ?
O1 N1 C1 C6 -163.0(3) . . . . ?
O2 N1 C1 C2 -161.3(3) . . . . ?
O2 N1 C1 C6 18.3(4) . . . . ?
N1 C1 C2 C3 178.6(2) . . . . ?
N1 C1 C6 C5 -179.1(2) . . . . ?
N2 C7 C8 N3 0.2(4) . . . . ?
N2 C9 C10 C11 179.1(2) . . . . ?
N2 C9 C14 N3 0.7(4) . . . . ?
N2 C9 C14 C13 -179.4(2) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 C7 -180.0(2) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C3 C4 C7 N2 6.0(3) . . . . ?
C3 C4 C7 C8 -174.0(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C7 C8 N3 -179.8(2) . . . . ?
C5 C4 C7 N2 -173.9(2) . . . . ?
C5 C4 C7 C8 6.1(4) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 N2 C9 C10 -178.9(2) . . . . ?
C7 N2 C9 C14 -0.4(3) . . . . ?
C7 C4 C5 C6 179.4(2) . . . . ?
C8 N3 C14 C9 -0.4(4) . . . . ?
C8 N3 C14 C13 179.7(2) . . . . ?
C9 N2 C7 C4 -179.96(19) . . . . ?
C9 N2 C7 C8 0.0(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C10 C9 C14 N3 179.1(2) . . . . ?
C10 C9 C14 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 N3 -179.1(2) . . . . ?
C12 C13 C14 C9 0.9(4) . . . . ?
C14 N3 C8 C7 0.0(4) . . . . ?
C14 C9 C10 C11 0.6(4) . . . . ?


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_6Chloro2phenylquinoxaline
_database_code_depnum_ccdc_archive 'CCDC 1506178'

_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_iucr_compatibility_tag          ?
_publcif_datablock.id            {39397030-960b-41f4-8b02-6294d4687151}

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2016-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68
_chemical_absolute_configuration ?
_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'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.5475(13)
_cell_length_b                   4.7592(5)
_cell_length_c                   12.4973(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.477(13)
_cell_angle_gamma                90
_cell_volume                     552.23(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5690
_cell_measurement_theta_min      4.3090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7467
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.382
_diffrn_reflns_theta_min         3.056
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                2104
_reflns_number_total             2654
_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         0.169
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 691 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.010
_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)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C1(H1), C5(H5), C8(H8), C13(H13), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.90425(8) 1.2900(3) 0.39245(7) 0.0566(3) Uani 1 1 d . . . . .
N1 N 0.4472(2) 0.4382(5) 0.30673(18) 0.0322(6) Uani 1 1 d . . . . .
N2 N 0.5816(3) 0.5969(6) 0.13779(19) 0.0412(7) Uani 1 1 d . . . . .
C9 C 0.6216(3) 0.7162(6) 0.2402(2) 0.0323(7) Uani 1 1 d . . . . .
C14 C 0.5536(3) 0.6352(7) 0.3242(2) 0.0315(6) Uani 1 1 d . . . . .
C7 C 0.4092(3) 0.3247(7) 0.2086(2) 0.0320(7) Uani 1 1 d . . . . .
C10 C 0.7307(3) 0.9213(7) 0.2614(2) 0.0388(7) Uani 1 1 d . . . . .
H10 H 0.7756 0.9766 0.2063 0.047 Uiso 1 1 calc R . . . .
C6 C 0.2934(3) 0.1111(6) 0.1878(2) 0.0338(6) Uani 1 1 d . . . . .
C11 C 0.7697(3) 1.0378(6) 0.3632(3) 0.0375(7) Uani 1 1 d . . . . .
C12 C 0.7030(3) 0.9595(7) 0.4477(2) 0.0409(7) Uani 1 1 d . . . . .
H12 H 0.7313 1.0420 0.5168 0.049 Uiso 1 1 calc R . . . .
C1 C 0.2243(3) 0.0441(7) 0.2715(3) 0.0427(8) Uani 1 1 d . . . . .
H1 H 0.2516 0.1345 0.3392 0.051 Uiso 1 1 calc R . . . .
C5 C 0.2483(3) -0.0263(7) 0.0878(2) 0.0435(8) Uani 1 1 d . . . . .
H5 H 0.2921 0.0153 0.0305 0.052 Uiso 1 1 calc R . . . .
C8 C 0.4791(3) 0.4098(7) 0.1241(2) 0.0405(8) Uani 1 1 d . . . . .
H8 H 0.4495 0.3265 0.0552 0.049 Uiso 1 1 calc R . . . .
C13 C 0.5976(3) 0.7639(8) 0.4282(2) 0.0392(8) Uani 1 1 d . . . . .
H13 H 0.5534 0.7133 0.4842 0.047 Uiso 1 1 calc R . . . .
C2 C 0.1165(3) -0.1537(8) 0.2552(3) 0.0494(9) Uani 1 1 d . . . . .
H2 H 0.0723 -0.1968 0.3121 0.059 Uiso 1 1 calc R . . . .
C4 C 0.1398(3) -0.2233(10) 0.0719(3) 0.0510(8) Uani 1 1 d . . . . .
H4 H 0.1111 -0.3131 0.0042 0.061 Uiso 1 1 calc R . . . .
C3 C 0.0734(3) -0.2883(7) 0.1557(3) 0.0507(10) Uani 1 1 d . . . . .
H3 H 0.0003 -0.4218 0.1449 0.061 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
Cl1 C11 1.734(3) . ?
N1 C14 1.363(4) . ?
N1 C7 1.311(3) . ?
N2 C9 1.370(3) . ?
N2 C8 1.305(4) . ?
C9 C14 1.411(4) . ?
C9 C10 1.407(4) . ?
C14 C13 1.409(4) . ?
C7 C6 1.479(4) . ?
C7 C8 1.433(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.358(4) . ?
C6 C1 1.398(4) . ?
C6 C5 1.387(4) . ?
C11 C12 1.404(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.350(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.374(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(5) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.375(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.379(5) . ?
C3 H3 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
C7 N1 C14 117.8(2) . . ?
C8 N2 C9 116.3(2) . . ?
N2 C9 C14 120.3(3) . . ?
N2 C9 C10 119.8(2) . . ?
C10 C9 C14 119.9(3) . . ?
N1 C14 C9 121.6(3) . . ?
N1 C14 C13 119.8(2) . . ?
C13 C14 C9 118.5(3) . . ?
N1 C7 C6 118.7(2) . . ?
N1 C7 C8 119.9(3) . . ?
C8 C7 C6 121.4(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.4 . . ?
C1 C6 C7 119.3(3) . . ?
C5 C6 C7 123.0(3) . . ?
C5 C6 C1 117.7(3) . . ?
C10 C11 Cl1 120.5(2) . . ?
C10 C11 C12 121.5(3) . . ?
C12 C11 Cl1 118.0(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
N2 C8 C7 124.0(3) . . ?
N2 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?

####################################################################### 
# 
# 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_7-Chloro-2-phenylquinoxaline
_database_code_depnum_ccdc_archive 'CCDC 1533362'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_publcif_datablock.id            {83910ecc-f963-4059-a6f8-8cdd7ddc4c39}

_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68
_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'
Cl Cl 0.1484 0.1585 '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                   3.8983(5)
_cell_length_b                   26.209(3)
_cell_length_c                   11.0333(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.286(11)
_cell_angle_gamma                90
_cell_volume                     1120.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    527
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.4990
_cell_measurement_theta_min      3.1010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1467
_diffrn_reflns_av_unetI/netI     0.1847
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14444
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.378
_diffrn_reflns_theta_min         2.981
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1275
_reflns_number_total             2831
_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         0.801
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2615
_refine_ls_R_factor_gt           0.1109
_refine_ls_restrained_S_all      0.967
_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)+(0.1336P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2407
_refine_ls_wR_factor_ref         0.3247
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C10(H10), C8(H8), C1(H1), C5(H5), C4(H4), C3(H3), C2(H2)
;
_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
Cl1 Cl 0.6472(4) 0.11093(5) 0.75867(16) 0.0694(7) Uani 1 1 d . . . . .
N1 N 0.6135(11) 0.30352(16) 0.7128(4) 0.0468(12) Uani 1 1 d . . . . .
N2 N 0.1940(13) 0.29525(17) 0.4867(4) 0.0544(13) Uani 1 1 d . . . . .
C7 C 0.5118(13) 0.3438(2) 0.6469(5) 0.0454(14) Uani 1 1 d . . . . .
C14 C 0.5050(13) 0.25719(18) 0.6647(5) 0.0403(13) Uani 1 1 d . . . . .
C6 C 0.6254(14) 0.39476(19) 0.6957(6) 0.0470(14) Uani 1 1 d . . . . .
C9 C 0.3014(14) 0.25327(19) 0.5527(5) 0.0448(14) Uani 1 1 d . . . . .
C13 C 0.6116(13) 0.21239(19) 0.7305(5) 0.0435(13) Uani 1 1 d . . . . .
H13 H 0.747605 0.214438 0.805041 0.052 Uiso 1 1 calc R . . . .
C12 C 0.5109(14) 0.16653(19) 0.6823(5) 0.0512(15) Uani 1 1 d . . . . .
C11 C 0.3087(15) 0.1622(2) 0.5692(6) 0.0557(16) Uani 1 1 d . . . . .
H11 H 0.246289 0.130079 0.538487 0.067 Uiso 1 1 calc R . . . .
C10 C 0.2032(15) 0.2047(2) 0.5042(6) 0.0567(16) Uani 1 1 d . . . . .
H10 H 0.069204 0.201858 0.429434 0.068 Uiso 1 1 calc R . . . .
C8 C 0.3003(15) 0.3394(2) 0.5344(5) 0.0532(15) Uani 1 1 d . . . . .
H8 H 0.233248 0.369085 0.492230 0.064 Uiso 1 1 calc R . . . .
C1 C 0.6886(14) 0.4024(2) 0.8194(6) 0.0552(16) Uani 1 1 d . . . . .
H1 H 0.657779 0.375597 0.872316 0.066 Uiso 1 1 calc R . . . .
C5 C 0.6793(16) 0.4354(2) 0.6185(6) 0.0692(19) Uani 1 1 d . . . . .
H5 H 0.643034 0.430852 0.534478 0.083 Uiso 1 1 calc R . . . .
C4 C 0.7865(17) 0.4826(2) 0.6657(8) 0.075(2) Uani 1 1 d . . . . .
H4 H 0.819419 0.509677 0.613823 0.090 Uiso 1 1 calc R . . . .
C3 C 0.8428(19) 0.4888(2) 0.7884(8) 0.080(2) Uani 1 1 d . . . . .
H3 H 0.913718 0.520376 0.820161 0.096 Uiso 1 1 calc R . . . .
C2 C 0.7971(18) 0.4493(2) 0.8663(7) 0.079(2) Uani 1 1 d . . . . .
H2 H 0.838856 0.453982 0.950174 0.094 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
Cl1 C12 1.737(5) . ?
N1 C7 1.317(6) . ?
N1 C14 1.373(6) . ?
N2 C9 1.360(6) . ?
N2 C8 1.319(6) . ?
C7 C6 1.490(7) . ?
C7 C8 1.417(8) . ?
C14 C9 1.398(7) . ?
C14 C13 1.418(6) . ?
C6 C1 1.374(8) . ?
C6 C5 1.394(7) . ?
C9 C10 1.417(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.355(7) . ?
C12 C11 1.405(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.364(7) . ?
C10 H10 0.9300 . ?
C8 H8 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.381(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.357(10) . ?
C3 H3 0.9300 . ?
C3 C2 1.369(9) . ?
C2 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
C7 N1 C14 115.7(5) . . ?
C8 N2 C9 115.5(5) . . ?
N1 C7 C6 117.3(5) . . ?
N1 C7 C8 122.0(5) . . ?
C8 C7 C6 120.7(5) . . ?
N1 C14 C9 121.8(5) . . ?
N1 C14 C13 118.3(5) . . ?
C9 C14 C13 119.9(5) . . ?
C1 C6 C7 120.2(5) . . ?
C1 C6 C5 118.2(5) . . ?
C5 C6 C7 121.5(6) . . ?
N2 C9 C14 121.7(5) . . ?
N2 C9 C10 118.0(5) . . ?
C14 C9 C10 120.2(5) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 C14 118.5(5) . . ?
C12 C13 H13 120.7 . . ?
C13 C12 Cl1 119.6(4) . . ?
C13 C12 C11 122.0(5) . . ?
C11 C12 Cl1 118.4(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11 119.7 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.8(6) . . ?
C11 C10 H10 120.6 . . ?
N2 C8 C7 123.2(5) . . ?
N2 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
C6 C1 H1 119.5 . . ?
C6 C1 C2 121.1(6) . . ?
C2 C1 H1 119.5 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.7 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.3(6) . . ?
C3 C4 H4 120.3 . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.2(6) . . ?
C2 C3 H3 119.4 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(7) . . ?
C3 C2 H2 120.3 . . ?

####################################################################### 
# 
# 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_6-Methoxy-2-phenylquinoxaline
_database_code_depnum_ccdc_archive 'CCDC 1533363'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_publcif_datablock.id            {bb3d3b9b-ad22-49d1-b39c-3390cb9dbe3d}

_audit_creation_date             2016-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_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           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                   16.0372(12)
_cell_length_b                   3.9616(3)
_cell_length_c                   18.8895(14)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 101.354(6)
_cell_angle_gamma                90.000(5)
_cell_volume                     1176.62(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1924
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2020
_cell_measurement_theta_min      3.7030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14785
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.429
_diffrn_reflns_theta_min         3.299
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1602
_reflns_number_total             2969
_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         0.159
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0092(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.030
_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)+(0.0490P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1419
_refine_special_details          
;
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:
 C8(H8), C14(H14), C11(H11), C12(H12), C5(H5), C4(H4), C1(H1), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
O1 O 0.09584(8) 0.3965(4) 0.47929(7) 0.0672(4) Uani 1 1 d . . . . .
N2 N 0.36051(8) 0.5373(3) 0.33436(7) 0.0450(4) Uani 1 1 d . . . . .
N1 N 0.38978(8) 0.2058(4) 0.46885(7) 0.0511(4) Uani 1 1 d . . . . .
C10 C 0.29704(10) 0.4967(4) 0.37215(8) 0.0413(4) Uani 1 1 d . . . . .
C7 C 0.43630(10) 0.4165(4) 0.36356(8) 0.0417(4) Uani 1 1 d . . . . .
C9 C 0.31158(10) 0.3345(4) 0.43990(8) 0.0412(4) Uani 1 1 d . . . . .
C8 C 0.44891(11) 0.2481(4) 0.43078(9) 0.0498(4) Uani 1 1 d . . . . .
H8 H 0.502732 0.161659 0.449153 0.060 Uiso 1 1 calc R . . . .
C14 C 0.24499(10) 0.2998(4) 0.47805(9) 0.0480(4) Uani 1 1 d . . . . .
H14 H 0.254670 0.195880 0.523073 0.058 Uiso 1 1 calc R . . . .
C6 C 0.50660(11) 0.4627(4) 0.32417(9) 0.0458(4) Uani 1 1 d . . . . .
C11 C 0.21473(10) 0.6200(4) 0.34360(9) 0.0509(5) Uani 1 1 d . . . . .
H11 H 0.203893 0.726811 0.298885 0.061 Uiso 1 1 calc R . . . .
C13 C 0.16648(11) 0.4195(4) 0.44856(9) 0.0496(4) Uani 1 1 d . . . . .
C12 C 0.15147(11) 0.5834(5) 0.38110(9) 0.0538(5) Uani 1 1 d . . . . .
H12 H 0.097562 0.667334 0.362094 0.065 Uiso 1 1 calc R . . . .
C5 C 0.49038(12) 0.6037(5) 0.25572(10) 0.0569(5) Uani 1 1 d . . . . .
H5 H 0.435399 0.671124 0.235168 0.068 Uiso 1 1 calc R . . . .
C15 C 0.10466(13) 0.2331(6) 0.54753(10) 0.0738(6) Uani 1 1 d . . . . .
H15A H 0.122961 0.004483 0.543432 0.111 Uiso 1 1 calc GR . . . .
H15B H 0.050917 0.233718 0.562670 0.111 Uiso 1 1 calc GR . . . .
H15C H 0.146034 0.350992 0.582480 0.111 Uiso 1 1 calc GR . . . .
C4 C 0.55471(14) 0.6451(5) 0.21771(11) 0.0717(6) Uani 1 1 d . . . . .
H4 H 0.542702 0.739049 0.171705 0.086 Uiso 1 1 calc R . . . .
C1 C 0.58977(11) 0.3700(5) 0.35378(10) 0.0641(6) Uani 1 1 d . . . . .
H1 H 0.602369 0.277543 0.399904 0.077 Uiso 1 1 calc R . . . .
C3 C 0.63605(14) 0.5492(6) 0.24708(13) 0.0793(7) Uani 1 1 d . . . . .
H3 H 0.679160 0.575257 0.221018 0.095 Uiso 1 1 calc R . . . .
C2 C 0.65367(13) 0.4139(6) 0.31543(12) 0.0798(7) Uani 1 1 d . . . . .
H2 H 0.709078 0.351612 0.335903 0.096 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 C13 1.3739(19) . ?
O1 C15 1.424(2) . ?
N2 C10 1.3629(18) . ?
N2 C7 1.3218(19) . ?
N1 C9 1.3646(19) . ?
N1 C8 1.309(2) . ?
C10 C9 1.410(2) . ?
C10 C11 1.411(2) . ?
C7 C8 1.413(2) . ?
C7 C6 1.479(2) . ?
C9 C14 1.408(2) . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.358(2) . ?
C6 C5 1.385(2) . ?
C6 C1 1.390(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(2) . ?
C13 C12 1.408(2) . ?
C12 H12 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.378(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.367(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.375(3) . ?
C2 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
C13 O1 C15 117.98(14) . . ?
C7 N2 C10 117.32(14) . . ?
C8 N1 C9 116.11(14) . . ?
N2 C10 C9 121.48(14) . . ?
N2 C10 C11 119.85(15) . . ?
C9 C10 C11 118.67(15) . . ?
N2 C7 C8 120.21(15) . . ?
N2 C7 C6 118.33(15) . . ?
C8 C7 C6 121.46(15) . . ?
N1 C9 C10 120.59(15) . . ?
N1 C9 C14 119.24(15) . . ?
C14 C9 C10 120.17(15) . . ?
N1 C8 C7 124.27(15) . . ?
N1 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.44(16) . . ?
C13 C14 H14 120.3 . . ?
C5 C6 C7 119.84(16) . . ?
C5 C6 C1 118.10(17) . . ?
C1 C6 C7 122.06(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.23(16) . . ?
C12 C11 H11 119.9 . . ?
O1 C13 C12 113.86(15) . . ?
C14 C13 O1 125.35(16) . . ?
C14 C13 C12 120.79(16) . . ?
C11 C12 C13 120.69(16) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.80(19) . . ?
C4 C5 H5 119.6 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.61(19) . . ?
C2 C1 H1 119.7 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?

####################################################################### 
# 
# 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_6-Nitro-2-phenylquinoxaline
_database_code_depnum_ccdc_archive 'CCDC 1533364'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_publcif_datablock.id            {dd483c66-0c6d-4134-a69b-bc00623d9949}

_audit_creation_date             2016-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 N3 O2'
_chemical_formula_sum            'C14 H9 N3 O2'
_chemical_formula_weight         251.24
_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                   3.9286(4)
_cell_length_b                   11.3555(15)
_cell_length_c                   13.3245(15)
_cell_angle_alpha                78.536(11)
_cell_angle_beta                 83.012(9)
_cell_angle_gamma                81.083(10)
_cell_volume                     572.98(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    903
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.1260
_cell_measurement_theta_min      3.3150
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7787
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.263
_diffrn_reflns_theta_min         3.333
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1298
_reflns_number_total             2701
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0664
_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1694
_refine_special_details          
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C8(H8), C12(H12), C1(H1), C5(H5), C2(H2), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N2 N 0.3003(4) 0.18694(17) 0.89329(15) 0.0397(5) Uani 1 1 d . . . . .
C13 C -0.2696(5) 0.2358(2) 1.16717(18) 0.0390(6) Uani 1 1 d . . . . .
C14 C -0.2824(6) 0.3319(2) 1.08739(18) 0.0406(6) Uani 1 1 d . . . . .
H14 H -0.414983 0.405484 1.094779 0.049 Uiso 1 1 calc R . . . .
C10 C 0.1103(5) 0.2039(2) 0.98359(18) 0.0351(6) Uani 1 1 d . . . . .
C9 C -0.0899(5) 0.3168(2) 0.99359(18) 0.0369(6) Uani 1 1 d . . . . .
C6 C 0.4895(6) 0.2634(2) 0.71679(18) 0.0384(6) Uani 1 1 d . . . . .
C11 C 0.1137(5) 0.1077(2) 1.06884(18) 0.0410(6) Uani 1 1 d . . . . .
H11 H 0.245027 0.033350 1.063254 0.049 Uiso 1 1 calc R . . . .
N1 N -0.0995(5) 0.41237(18) 0.91231(15) 0.0452(6) Uani 1 1 d . . . . .
N3 N -0.4767(5) 0.2493(2) 1.26509(17) 0.0512(6) Uani 1 1 d . . . . .
C7 C 0.2914(5) 0.2802(2) 0.81594(18) 0.0376(6) Uani 1 1 d . . . . .
C8 C 0.0855(6) 0.3927(2) 0.82771(19) 0.0453(6) Uani 1 1 d . . . . .
H8 H 0.083261 0.456026 0.771401 0.054 Uiso 1 1 calc R . . . .
O2 O -0.5074(5) 0.15801(19) 1.32927(15) 0.0789(7) Uani 1 1 d . . . . .
C12 C -0.0748(6) 0.1231(2) 1.15951(19) 0.0437(6) Uani 1 1 d . . . . .
H12 H -0.073932 0.059514 1.215562 0.052 Uiso 1 1 calc R . . . .
C1 C 0.5821(6) 0.3612(2) 0.64290(19) 0.0514(7) Uani 1 1 d . . . . .
H1 H 0.519276 0.439850 0.655202 0.062 Uiso 1 1 calc R . . . .
C5 C 0.5842(6) 0.1478(2) 0.6948(2) 0.0496(7) Uani 1 1 d . . . . .
H5 H 0.523028 0.081376 0.742974 0.059 Uiso 1 1 calc R . . . .
O1 O -0.6126(5) 0.35031(19) 1.27717(15) 0.0833(7) Uani 1 1 d . . . . .
C2 C 0.7679(6) 0.3416(3) 0.5510(2) 0.0592(8) Uani 1 1 d . . . . .
H2 H 0.829920 0.407332 0.502159 0.071 Uiso 1 1 calc R . . . .
C4 C 0.7672(7) 0.1294(3) 0.6029(2) 0.0603(8) Uani 1 1 d . . . . .
H4 H 0.827158 0.051150 0.589372 0.072 Uiso 1 1 calc R . . . .
C3 C 0.8610(7) 0.2267(3) 0.5311(2) 0.0614(8) Uani 1 1 d . . . . .
H3 H 0.987035 0.214536 0.469438 0.074 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
N2 C10 1.368(3) . ?
N2 C7 1.322(3) . ?
C13 C14 1.363(3) . ?
C13 N3 1.473(3) . ?
C13 C12 1.401(3) . ?
C14 C9 1.406(3) . ?
C10 C9 1.417(3) . ?
C10 C11 1.411(3) . ?
C9 N1 1.372(3) . ?
C6 C7 1.480(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.387(3) . ?
C11 C12 1.366(3) . ?
N1 C8 1.303(3) . ?
N3 O2 1.218(3) . ?
N3 O1 1.220(3) . ?
C7 C8 1.429(3) . ?
C1 C2 1.387(3) . ?
C5 C4 1.379(3) . ?
C2 C3 1.367(4) . ?
C4 C3 1.376(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 C10 117.4(2) . . ?
C14 C13 N3 118.9(2) . . ?
C14 C13 C12 122.9(2) . . ?
C12 C13 N3 118.2(2) . . ?
C13 C14 C9 118.3(2) . . ?
N2 C10 C9 121.3(2) . . ?
N2 C10 C11 119.6(2) . . ?
C11 C10 C9 119.1(2) . . ?
C14 C9 C10 120.1(2) . . ?
N1 C9 C14 119.2(2) . . ?
N1 C9 C10 120.7(2) . . ?
C1 C6 C7 121.9(2) . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 C1 118.1(2) . . ?
C12 C11 C10 120.3(2) . . ?
C8 N1 C9 116.2(2) . . ?
O2 N3 C13 117.8(2) . . ?
O2 N3 O1 123.5(2) . . ?
O1 N3 C13 118.8(2) . . ?
N2 C7 C6 118.4(2) . . ?
N2 C7 C8 120.3(2) . . ?
C8 C7 C6 121.3(2) . . ?
N1 C8 C7 124.2(2) . . ?
C11 C12 C13 119.3(2) . . ?
C2 C1 C6 120.1(3) . . ?
C4 C5 C6 121.3(2) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C4 C5 120.0(3) . . ?
C2 C3 C4 119.7(3) . . ?

