# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_IIa
_database_code_depnum_ccdc_archive 'CCDC 1832638'
loop_
_audit_author_name
_audit_author_address
'Ali Samie'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 Phenyl pyrazine-2-carboxylate (IIa)
;
_chemical_name_common            IIa
_chemical_melting_point          364.6
_chemical_formula_moiety         'C11 H8 N2 O2'
_chemical_formula_sum            'C11 H8 N2 O2'
_chemical_formula_weight         200.19

# start Validation Reply Form
_vrf_RINTA01_IIa                 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: This is due to the poor quality of crystal.
;
# end Validation Reply Form

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.767(5)
_cell_length_b                   10.249(9)
_cell_length_c                   16.039(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     948.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    138(2)
_cell_measurement_reflns_used    3898
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      33.8

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   Multi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      138(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            9710
_diffrn_reflns_av_unetI/netI     0.1150
_diffrn_reflns_av_R_equivalents  0.2091
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.358
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2066
_reflns_number_gt                2013
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_cell_refinement       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_reduction        
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.0156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.089(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 797 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2066
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.4702(3) 0.2286(2) 0.24710(12) 0.0288(5) Uani 1 1 d . . . . .
C6 C 0.3003(4) 0.3031(3) 0.28465(15) 0.0374(6) Uani 1 1 d . . . . .
H6 H 0.1654 0.3283 0.2547 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3312(4) 0.3406(3) 0.36759(15) 0.0406(6) Uani 1 1 d . . . . .
H5 H 0.2166 0.3918 0.3948 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5292(4) 0.3029(3) 0.41002(13) 0.0386(5) Uani 1 1 d . . . . .
H4 H 0.5482 0.3268 0.4668 0.046 Uiso 1 1 calc R U . . .
C3 C 0.6993(4) 0.2309(3) 0.37060(13) 0.0368(5) Uani 1 1 d . . . . .
H3 H 0.8363 0.2076 0.3999 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6705(3) 0.1922(2) 0.28771(13) 0.0327(5) Uani 1 1 d . . . . .
H2 H 0.7860 0.1421 0.2601 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2736(3) 0.1215(2) 0.13629(12) 0.0271(5) Uani 1 1 d . . . . .
C8 C 0.2872(3) 0.1008(2) 0.04363(12) 0.0251(4) Uani 1 1 d . . . . .
C9 C 0.4950(3) 0.1133(2) 0.00000(13) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.6311 0.1390 0.0291 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3093(4) 0.0563(3) -0.11946(13) 0.0338(5) Uani 1 1 d . . . . .
H10 H 0.3101 0.0387 -0.1776 0.041 Uiso 1 1 calc R U . . .
C11 C 0.1010(3) 0.0463(3) -0.07594(14) 0.0328(5) Uani 1 1 d . . . . .
H11 H -0.0362 0.0245 -0.1056 0.039 Uiso 1 1 calc R U . . .
N2 N 0.0884(3) 0.0664(2) 0.00628(11) 0.0298(4) Uani 1 1 d . . . . .
N1 N 0.5073(3) 0.0896(2) -0.08242(11) 0.0347(5) Uani 1 1 d . . . . .
O1 O 0.1256(3) 0.07744(19) 0.18053(9) 0.0381(5) Uani 1 1 d . . . . .
O2 O 0.4544(2) 0.19464(18) 0.16184(8) 0.0324(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(3) . ?
C1 C6 1.380(3) . ?
C1 O2 1.414(3) . ?
C6 C5 1.396(3) . ?
C5 C4 1.384(4) . ?
C4 C3 1.381(3) . ?
C3 C2 1.397(3) . ?
C7 O1 1.198(2) . ?
C7 O2 1.348(3) . ?
C7 C8 1.503(3) . ?
C8 N2 1.341(3) . ?
C8 C9 1.394(3) . ?
C9 N1 1.346(3) . ?
C10 N1 1.332(3) . ?
C10 C11 1.393(3) . ?
C11 N2 1.337(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
C2 C1 C6 122.6(2) . . ?
C2 C1 O2 116.39(18) . . ?
C6 C1 O2 120.83(18) . . ?
C1 C6 C5 118.5(2) . . ?
C4 C5 C6 119.8(2) . . ?
C5 C4 C3 120.7(2) . . ?
C4 C3 C2 120.2(2) . . ?
C1 C2 C3 118.2(2) . . ?
O1 C7 O2 125.47(18) . . ?
O1 C7 C8 124.75(18) . . ?
O2 C7 C8 109.77(15) . . ?
N2 C8 C9 122.35(17) . . ?
N2 C8 C7 115.71(15) . . ?
C9 C8 C7 121.92(16) . . ?
N1 C9 C8 121.48(18) . . ?
N1 C10 C11 122.32(19) . . ?
N2 C11 C10 122.01(18) . . ?
C11 N2 C8 115.77(16) . . ?
C10 N1 C9 116.04(16) . . ?
C7 O2 C1 118.73(15) . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
####################################################################### 
# 
# 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_IIb
_database_code_depnum_ccdc_archive 'CCDC 1832639'
loop_
_audit_author_name
_audit_author_address
'Ali Samie'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2019-05-09 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 Phenyl pyrazine-2-carboxylate (IIb)
;
_chemical_name_common            IIb
_chemical_melting_point          362.3
_chemical_formula_moiety         'C11 H8 N2 O2'
_chemical_formula_sum            'C11 H8 N2 O2'
_chemical_formula_weight         200.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   12.657(15)
_cell_length_b                   5.606(7)
_cell_length_c                   13.836(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.939(12)
_cell_angle_gamma                90
_cell_volume                     979(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1987
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   Multi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            9834
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.951
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2234
_reflns_number_gt                1804
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_collection       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_reduction        
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)²+0.1632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.076(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2234
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.29254(11) 0.2522(3) 0.72847(10) 0.0441(4) Uani 1 1 d . . . . .
C2 C 0.36100(12) 0.4421(3) 0.73765(13) 0.0538(4) Uani 1 1 d . . . . .
H2 H 0.3607 0.5621 0.6892 0.065 Uiso 1 1 calc R U . . .
C3 C 0.43056(12) 0.4545(3) 0.81931(14) 0.0611(5) Uani 1 1 d . . . . .
H3 H 0.4791 0.5835 0.8267 0.073 Uiso 1 1 calc R U . . .
C4 C 0.42982(12) 0.2814(3) 0.88985(12) 0.0573(4) Uani 1 1 d . . . . .
H4 H 0.4777 0.2911 0.9457 0.069 Uiso 1 1 calc R U . . .
C5 C 0.35952(13) 0.0940(3) 0.87935(12) 0.0576(4) Uani 1 1 d . . . . .
H5 H 0.3588 -0.0246 0.9283 0.069 Uiso 1 1 calc R U . . .
C6 C 0.28980(12) 0.0772(3) 0.79794(11) 0.0524(4) Uani 1 1 d . . . . .
H6 H 0.2413 -0.0520 0.7903 0.063 Uiso 1 1 calc R U . . .
C7 C 0.23725(11) 0.0799(3) 0.57865(10) 0.0453(4) Uani 1 1 d . . . . .
C8 C 0.15943(10) 0.0948(2) 0.49262(10) 0.0411(3) Uani 1 1 d . . . . .
C9 C 0.16078(13) -0.0846(3) 0.42430(12) 0.0557(4) Uani 1 1 d . . . . .
H9 H 0.2097 -0.2120 0.4347 0.067 Uiso 1 1 calc R U . . .
C10 C 0.02958(12) 0.0980(3) 0.33525(11) 0.0530(4) Uani 1 1 d . . . . .
H10 H -0.0181 0.1067 0.2793 0.064 Uiso 1 1 calc R U . . .
C11 C 0.02696(12) 0.2765(3) 0.40382(12) 0.0541(4) Uani 1 1 d . . . . .
H11 H -0.0227 0.4026 0.3937 0.065 Uiso 1 1 calc R U . . .
N1 N 0.09590(11) -0.0852(3) 0.34427(10) 0.0596(4) Uani 1 1 d . . . . .
N2 N 0.09201(10) 0.2773(2) 0.48386(9) 0.0492(4) Uani 1 1 d . . . . .
O1 O 0.30699(10) -0.0643(2) 0.58545(9) 0.0706(4) Uani 1 1 d . . . . .
O2 O 0.21988(8) 0.24637(19) 0.64591(7) 0.0520(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(2) . ?
C1 C6 1.376(2) . ?
C1 O2 1.417(2) . ?
C2 C3 1.386(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.386(2) . ?
C7 O1 1.196(2) . ?
C7 O2 1.346(2) . ?
C7 C8 1.494(2) . ?
C8 N2 1.332(2) . ?
C8 C9 1.381(2) . ?
C9 N1 1.332(2) . ?
C10 N1 1.327(2) . ?
C10 C11 1.381(3) . ?
C11 N2 1.334(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.31(15) . . ?
C2 C1 O2 117.57(14) . . ?
C6 C1 O2 120.06(14) . . ?
C1 C2 C3 118.43(15) . . ?
C4 C3 C2 120.50(16) . . ?
C3 C4 C5 119.90(16) . . ?
C4 C5 C6 120.55(16) . . ?
C1 C6 C5 118.31(15) . . ?
O1 C7 O2 124.67(14) . . ?
O1 C7 C8 122.88(14) . . ?
O2 C7 C8 112.45(13) . . ?
N2 C8 C9 122.32(14) . . ?
N2 C8 C7 119.90(13) . . ?
C9 C8 C7 117.78(13) . . ?
N1 C9 C8 122.34(15) . . ?
N1 C10 C11 122.76(15) . . ?
N2 C11 C10 122.03(15) . . ?
C10 N1 C9 115.20(14) . . ?
C8 N2 C11 115.34(13) . . ?
C7 O2 C1 116.44(12) . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane and Ethyl Acetate'
####################################################################### 
# 
# 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_Ib
_database_code_depnum_ccdc_archive 'CCDC 1832641'
loop_
_audit_author_name
_audit_author_address
'Ali Samie'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2019-05-02 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_Ib                  
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The investigated single crystal was a small-sized, brittle 
and poorly diffracting plate. A lot of attempts was made to obtain better 
quality data for this structure, however, due to poor crystal quality 
and very weak diffraction, the Rint value is high. Numerous datasets 
were collected on single crystals from different batches, 
whereof the one of the highest quality is reported herein.
;
_vrf_PLAT020_Ib                  
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.249 Report
RESPONSE: The investigated single crystal was a small-sized, brittle 
and poorly diffracting plate. A lot of attempts was made to obtain better 
quality data for this structure, however, due to poor crystal quality 
and very weak diffraction, the Rint value is high. Numerous datasets 
were collected on single crystals from different batches, 
whereof the one of the highest quality is reported herein.
;
_vrf_PLAT084_Ib                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report
RESPONSE: The investigated single crystal was a small-sized, brittle 
and poorly diffracting plate. A lot of attempts was made to obtain better 
quality data for this structure, however, due to poor crystal quality
the R2 value is high. Numerous datasets were collected on single 
crystals from different batches, whereof the one of the highest quality is 
reported herein.
;
_vrf_PLAT230_Ib                  
;
PROBLEM: Hirshfeld Test Diff for    O2       --C1       .        9.7 s.u.  
RESPONSE: Quality of the data is not enough to get good anisotropic
displacement parameters.
;
_vrf_PLAT082_Ib                  
;
PROBLEM: High R1 Value ..................................       0.13 Report
RESPONSE: A lot of attempts was made to obtain better 
quality data for this structure, however, due to poor crystal quality
the R1 value is high. 
;
_vrf_PLAT148_Ib                  
;
PROBLEM: s.u. on the      a    - Axis is (Too) Large ....      0.015 Ang.  
RESPONSE: ...
;
_vrf_PLAT340_Ib                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00709 Ang.  
RESPONSE: The low bond precision on the C-C bonds may derived from the low 
quality of data.
;
_vrf_PLAT369_Ib                  
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C7       - C8       .       1.55 Ang.  
RESPONSE: Quality of the data is not enough to get good bond length
parameters.
;
_vrf_PLAT911_Ib                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        124 Report
RESPONSE: A full set of data was collected, however the high angle
data was dominated by noise and was omitted.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 Phenyl pyridine-2-carboxylate (Ib)
;
_chemical_name_common            Ib
_chemical_melting_point          341.8
_chemical_formula_moiety         'C12 H9 N O2'
_chemical_formula_sum            'C12 H9 N O2'
_chemical_formula_weight         199.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.994(15)
_cell_length_b                   6.095(12)
_cell_length_c                   20.94(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.20(2)
_cell_angle_gamma                90
_cell_volume                     1018(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1933
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   Multi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_reflns_number            8636
_diffrn_reflns_av_unetI/netI     0.1477
_diffrn_reflns_av_R_equivalents  0.2487
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.667
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             2205
_reflns_number_gt                1212
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_collection       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_reduction        
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.10(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2205
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1675
_refine_ls_R_factor_gt           0.1266
_refine_ls_wR_factor_ref         0.3771
_refine_ls_wR_factor_gt          0.3342
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.2047(5) 0.7130(7) 0.83431(18) 0.0635(10) Uani 1 1 d . . . . .
C2 C 0.1325(6) 0.9016(7) 0.8518(2) 0.0736(12) Uani 1 1 d . . . . .
H2 H 0.1804 0.9850 0.8868 0.088 Uiso 1 1 calc R U . . .
C3 C -0.0122(7) 0.9713(8) 0.8178(2) 0.0852(14) Uani 1 1 d . . . . .
H3 H -0.0671 1.1006 0.8306 0.102 Uiso 1 1 calc R U . . .
C4 C -0.0777(6) 0.8533(9) 0.7650(2) 0.0841(14) Uani 1 1 d . . . . .
H4 H -0.1746 0.9047 0.7406 0.101 Uiso 1 1 calc R U . . .
C5 C -0.0036(5) 0.6671(8) 0.7489(2) 0.0747(12) Uani 1 1 d . . . . .
H5 H -0.0506 0.5855 0.7134 0.090 Uiso 1 1 calc R U . . .
C6 C 0.1375(6) 0.5907(7) 0.7821(2) 0.0712(11) Uani 1 1 d . . . . .
H6 H 0.1889 0.4579 0.7701 0.085 Uiso 1 1 calc R U . . .
C7 C 0.3661(5) 0.4823(7) 0.8984(2) 0.0726(12) Uani 1 1 d . . . . .
C8 C 0.5511(5) 0.4233(7) 0.91886(17) 0.0662(11) Uani 1 1 d . . . . .
C9 C 0.5684(6) 0.2291(8) 0.9535(2) 0.0814(13) Uani 1 1 d . . . . .
H9 H 0.4714 0.1509 0.9640 0.098 Uiso 1 1 calc R U . . .
C10 C 0.8515(7) 0.2676(10) 0.9583(3) 0.0897(15) Uani 1 1 d . . . . .
H10 H 0.9605 0.2149 0.9713 0.108 Uiso 1 1 calc R U . . .
C11 C 0.8390(6) 0.4598(10) 0.9262(2) 0.0930(16) Uani 1 1 d . . . . .
H11 H 0.9372 0.5392 0.9177 0.112 Uiso 1 1 calc R U . . .
C12 C 0.6893(6) 0.5367(9) 0.9066(2) 0.0777(13) Uani 1 1 d . . . . .
H12 H 0.6795 0.6717 0.8840 0.093 Uiso 1 1 calc R U . . .
N1 N 0.7234(7) 0.1503(7) 0.9725(2) 0.0969(14) Uani 1 1 d . . . . .
O1 O 0.2489(4) 0.3824(6) 0.91343(18) 0.0888(11) Uani 1 1 d . . . . .
O2 O 0.3642(4) 0.6602(5) 0.86356(15) 0.0820(11) 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
C1 C2 1.349(6) . ?
C1 C6 1.397(6) . ?
C1 O2 1.411(5) . ?
C2 C3 1.380(7) . ?
C3 C4 1.389(8) . ?
C4 C5 1.335(7) . ?
C5 C6 1.363(7) . ?
C7 O1 1.179(5) . ?
C7 O2 1.307(6) . ?
C7 C8 1.551(7) . ?
C8 C12 1.344(6) . ?
C8 C9 1.389(7) . ?
C9 N1 1.361(7) . ?
C10 N1 1.301(7) . ?
C10 C11 1.351(8) . ?
C11 C12 1.322(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.3(4) . . ?
C2 C1 O2 117.9(4) . . ?
C6 C1 O2 120.1(4) . . ?
C1 C2 C3 118.8(4) . . ?
C2 C3 C4 120.3(4) . . ?
C5 C4 C3 119.5(4) . . ?
C4 C5 C6 121.9(4) . . ?
C5 C6 C1 118.2(4) . . ?
O1 C7 O2 126.9(5) . . ?
O1 C7 C8 124.5(5) . . ?
O2 C7 C8 108.6(3) . . ?
C12 C8 C9 119.0(4) . . ?
C12 C8 C7 127.5(4) . . ?
C9 C8 C7 113.4(4) . . ?
N1 C9 C8 120.5(4) . . ?
N1 C10 C11 124.0(5) . . ?
C12 C11 C10 119.6(5) . . ?
C11 C12 C8 119.8(5) . . ?
C10 N1 C9 117.0(5) . . ?
C7 O2 C1 113.9(3) . . ?

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane and Ethyl Acetate'
####################################################################### 
# 
# 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_Ia
_database_code_depnum_ccdc_archive 'CCDC 1832640'
loop_
_audit_author_name
_audit_author_address
'Ali Samie'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-06-03 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_shelxl_version_number           2013-4
_chemical_name_common            Ia
_chemical_name_systematic        
;
 Phenyl pyridine-2-carboxylate (Ia)
;
_chemical_formula_moiety         'C12 H9 N O2'
_chemical_formula_sum            'C12 H9 N O2'
_chemical_formula_weight         199.20
_chemical_melting_point          344.8

# start Validation Reply Form
_vrf_RINTA01_Ia                  
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: This is due to the poor quality of crystal.
;
_vrf_PLAT020_Ia                  
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.189 Report
RESPONSE: This is due to the poor quality of crystal.
;
# end Validation Reply Form

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

_cell_length_a                   14.759(3)
_cell_length_b                   6.9112(19)
_cell_length_c                   20.003(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2040.4(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.4
_cell_measurement_theta_min      1.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   Multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1893
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19262
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_min         2.760
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1007
_reflns_number_total             2221
_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       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_collection       
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_data_reduction        
'CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2079
_refine_ls_R_factor_gt           0.0913
_refine_ls_restrained_S_all      1.095
_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)+(0.0588P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1894
_refine_special_details          
;
 ?
;
_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
C1 C 0.9991(2) 0.5360(6) 0.86490(16) 0.0569(10) Uani 1 1 d . . . . .
C6 C 1.0412(3) 0.3625(7) 0.8608(2) 0.0760(12) Uani 1 1 d . . . . .
H6 H 1.0192 0.2559 0.8841 0.091 Uiso 1 1 calc R U . . .
C5 C 1.1173(3) 0.3476(8) 0.8216(2) 0.0972(15) Uani 1 1 d . . . . .
H5 H 1.1473 0.2297 0.8181 0.117 Uiso 1 1 calc R U . . .
C4 C 1.1488(3) 0.5034(9) 0.7882(2) 0.0969(19) Uani 1 1 d . . . . .
H4 H 1.2006 0.4915 0.7620 0.116 Uiso 1 1 calc R U . . .
C3 C 1.1057(3) 0.6790(9) 0.7920(2) 0.0982(16) Uani 1 1 d . . . . .
H3 H 1.1277 0.7851 0.7685 0.118 Uiso 1 1 calc R U . . .
C2 C 1.0283(3) 0.6960(7) 0.8318(2) 0.0790(12) Uani 1 1 d . . . . .
H2 H 0.9977 0.8131 0.8355 0.095 Uiso 1 1 calc R U . . .
C7 C 0.8413(2) 0.5458(5) 0.88114(19) 0.0567(9) Uani 1 1 d . . . . .
C8 C 0.7678(2) 0.5547(5) 0.93167(16) 0.0481(8) Uani 1 1 d . . . . .
C9 C 0.6790(2) 0.5478(5) 0.90977(18) 0.0592(10) Uani 1 1 d . . . . .
H9 H 0.6693 0.5396 0.8639 0.071 Uiso 1 1 calc R U . . .
C10 C 0.6231(3) 0.5654(5) 1.0137(2) 0.0705(11) Uani 1 1 d . . . . .
H10 H 0.5735 0.5684 1.0424 0.085 Uiso 1 1 calc R U . . .
C11 C 0.7078(3) 0.5751(5) 1.04139(19) 0.0702(11) Uani 1 1 d . . . . .
H11 H 0.7151 0.5859 1.0874 0.084 Uiso 1 1 calc R U . . .
C12 C 0.7821(2) 0.5685(5) 0.99938(17) 0.0585(10) Uani 1 1 d . . . . .
H12 H 0.8406 0.5734 1.0166 0.070 Uiso 1 1 calc R U . . .
N1 N 0.60700(19) 0.5520(4) 0.94875(16) 0.0663(9) Uani 1 1 d . . . . .
O1 O 0.82925(16) 0.5314(4) 0.82236(13) 0.0879(10) Uani 1 1 d . . . . .
O2 O 0.92340(15) 0.5533(3) 0.90900(11) 0.0640(7) 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
C1 C6 1.353(5) . ?
C1 C2 1.359(5) . ?
C1 O2 1.428(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.374(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.350(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.372(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.397(5) . ?
C2 H2 0.9300 . ?
C7 C8 1.484(5) . ?
C7 O1 1.193(4) . ?
C7 O2 1.334(4) . ?
C8 C9 1.383(4) . ?
C8 C12 1.374(4) . ?
C9 H9 0.9300 . ?
C9 N1 1.318(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(5) . ?
C10 N1 1.324(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(5) . ?
C12 H12 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
C6 C1 C2 123.1(4) . . ?
C6 C1 O2 118.1(4) . . ?
C2 C1 O2 118.8(4) . . ?
C1 C6 H6 120.8 . . ?
C1 C6 C5 118.5(4) . . ?
C5 C6 H6 120.8 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5 119.8 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.2(5) . . ?
C3 C4 H4 119.4 . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 119.1(5) . . ?
C2 C3 H3 120.5 . . ?
C1 C2 C3 117.9(4) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
O1 C7 C8 124.4(3) . . ?
O1 C7 O2 123.4(3) . . ?
O2 C7 C8 112.2(3) . . ?
C9 C8 C7 118.4(3) . . ?
C12 C8 C7 124.2(3) . . ?
C12 C8 C9 117.4(3) . . ?
C8 C9 H9 117.4 . . ?
N1 C9 C8 125.2(3) . . ?
N1 C9 H9 117.4 . . ?
C11 C10 H10 117.8 . . ?
N1 C10 H10 117.8 . . ?
N1 C10 C11 124.3(3) . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.5(4) . . ?
C12 C11 H11 120.7 . . ?
C8 C12 C11 118.7(3) . . ?
C8 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C9 N1 C10 115.9(3) . . ?
C7 O2 C1 116.7(3) . . ?

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
C1 C6 C5 C4 0.0(6) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
C6 C1 O2 C7 -100.7(4) . . . . ?
C6 C5 C4 C3 -0.4(7) . . . . ?
C5 C4 C3 C2 0.4(7) . . . . ?
C4 C3 C2 C1 -0.1(6) . . . . ?
C2 C1 C6 C5 0.3(6) . . . . ?
C2 C1 O2 C7 82.7(4) . . . . ?
C7 C8 C9 N1 179.2(3) . . . . ?
C7 C8 C12 C11 -179.8(3) . . . . ?
C8 C7 O2 C1 177.0(3) . . . . ?
C8 C9 N1 C10 0.5(5) . . . . ?
C9 C8 C12 C11 -0.1(5) . . . . ?
C10 C11 C12 C8 0.7(6) . . . . ?
C11 C10 N1 C9 0.1(6) . . . . ?
C12 C8 C9 N1 -0.5(5) . . . . ?
N1 C10 C11 C12 -0.7(6) . . . . ?
O1 C7 C8 C9 -0.6(6) . . . . ?
O1 C7 C8 C12 179.1(4) . . . . ?
O1 C7 O2 C1 -2.3(5) . . . . ?
O2 C1 C6 C5 -176.2(3) . . . . ?
O2 C1 C2 C3 176.2(3) . . . . ?
O2 C7 C8 C9 -179.8(3) . . . . ?
O2 C7 C8 C12 -0.2(5) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane and ethyl acetate'
