# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_3jula_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1903353'
loop_
_audit_author_name
_audit_author_address
'Dr. Meenu Teotia'
;Ch. Charan Singh University Meerut UP India
India
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N2 O2'
_chemical_formula_weight         248.32

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.0286(19)
_cell_length_b                   7.660(3)
_cell_length_c                   9.751(4)
_cell_angle_alpha                105.952(9)
_cell_angle_beta                 95.479(9)
_cell_angle_gamma                106.190(9)
_cell_volume                     340.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             134
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3419
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1205
_reflns_number_gt                757
_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_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1205
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1922
_refine_ls_wR_factor_gt          0.1600
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_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
O1 O 0.2833(4) 0.7078(4) 0.3387(2) 0.0593(8) Uani 1 1 d . . . . .
N1 N 0.7220(5) 0.7046(4) 0.4014(3) 0.0419(8) Uani 1 1 d . . . . .
H1A H 0.8664 0.6769 0.3731 0.050 Uiso 1 1 calc R U . . .
C3 C 0.5052(6) 0.5834(4) 0.1476(3) 0.0342(8) Uani 1 1 d . . . . .
C4 C 0.4939(6) 0.6693(5) 0.3027(3) 0.0388(8) Uani 1 1 d . . . . .
C1 C 0.3435(6) 0.5409(5) -0.1035(3) 0.0423(9) Uani 1 1 d . . . . .
H1 H 0.2377 0.5697 -0.1727 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3480(6) 0.6228(5) 0.0422(3) 0.0413(9) Uani 1 1 d . . . . .
H2 H 0.2440 0.7055 0.0699 0.050 Uiso 1 1 calc R U . . .
C5 C 0.7310(7) 0.7891(5) 0.5560(3) 0.0487(9) Uani 1 1 d . . . . .
H5A H 0.5750 0.7094 0.5852 0.058 Uiso 1 1 calc R U . . .
H5B H 0.7073 0.9142 0.5728 0.058 Uiso 1 1 calc R U . . .
C6 C 0.9994(8) 0.8098(6) 0.6472(4) 0.0545(10) Uani 1 1 d . . . . .
H6A H 1.1562 0.8860 0.6161 0.065 Uiso 1 1 calc R U . . .
H6B H 1.0202 0.6842 0.6332 0.065 Uiso 1 1 calc R U . . .
C7 C 1.0098(9) 0.9039(6) 0.8071(4) 0.0663(12) Uani 1 1 d . . . . .
H7A H 0.9834 1.0266 0.8210 0.099 Uiso 1 1 calc R U . . .
H7B H 1.1896 0.9206 0.8615 0.099 Uiso 1 1 calc R U . . .
H7C H 0.8631 0.8243 0.8400 0.099 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0310(12) 0.098(2) 0.0448(15) 0.0029(13) 0.0105(10) 0.0331(13)
N1 0.0286(13) 0.0647(19) 0.0318(15) 0.0069(12) 0.0075(11) 0.0216(13)
C3 0.0213(15) 0.0419(19) 0.0376(18) 0.0103(14) 0.0057(12) 0.0093(14)
C4 0.0275(16) 0.049(2) 0.0371(19) 0.0085(15) 0.0093(14) 0.0124(15)
C1 0.0373(18) 0.057(2) 0.0368(19) 0.0132(15) 0.0036(13) 0.0241(16)
C2 0.0369(17) 0.049(2) 0.041(2) 0.0081(15) 0.0069(14) 0.0244(16)
C5 0.0413(19) 0.069(2) 0.0343(19) 0.0071(16) 0.0105(14) 0.0239(17)
C6 0.057(2) 0.071(3) 0.040(2) 0.0150(18) 0.0084(16) 0.029(2)
C7 0.077(3) 0.078(3) 0.035(2) 0.0084(19) 0.0050(19) 0.022(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.233(3) . ?
N1 C4 1.337(4) . ?
N1 C5 1.459(4) . ?
N1 H1A 0.8600 . ?
C3 C1 1.382(4) 2_665 ?
C3 C2 1.386(4) . ?
C3 C4 1.488(4) . ?
C1 C2 1.382(4) . ?
C1 C3 1.382(4) 2_665 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C5 C6 1.488(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.516(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C5 121.3(2) . . ?
C4 N1 H1A 119.3 . . ?
C5 N1 H1A 119.3 . . ?
C1 C3 C2 118.4(3) 2_665 . ?
C1 C3 C4 122.8(3) 2_665 . ?
C2 C3 C4 118.8(3) . . ?
O1 C4 N1 121.3(3) . . ?
O1 C4 C3 121.3(3) . . ?
N1 C4 C3 117.4(2) . . ?
C2 C1 C3 120.7(3) . 2_665 ?
C2 C1 H1 119.7 . . ?
C3 C1 H1 119.7 2_665 . ?
C1 C2 C3 120.9(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
N1 C5 C6 112.7(3) . . ?
N1 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 112.1(3) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.051

_shelx_res_file                  
;

    3jula_0m_a.res created by SHELXL-2014/7

TITL 3jula_0m_a.res in P-1
CELL  0.71073   5.0286   7.6603   9.7509  105.952   95.479  106.190
ZERR    1.000   0.0019   0.0029   0.0038    0.009    0.009    0.009
LATT 1
SFAC C  H  N  O
UNIT 14  20  2  2
OMIT -2 50.1
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 20
TEMP 23.000
WGHT    0.100000    0.281800
FVAR       1.53355
O1    4    0.283263    0.707778    0.338704    11.00000    0.03099    0.09824 =
         0.04482    0.00286    0.01049    0.03308
N1    3    0.722006    0.704578    0.401376    11.00000    0.02857    0.06473 =
         0.03177    0.00690    0.00747    0.02164
AFIX  43
H1A   2    0.866358    0.676913    0.373123    11.00000   -1.20000
AFIX   0
C3    1    0.505229    0.583383    0.147614    11.00000    0.02133    0.04186 =
         0.03760    0.01029    0.00568    0.00929
C4    1    0.493949    0.669256    0.302730    11.00000    0.02745    0.04938 =
         0.03707    0.00854    0.00934    0.01244
C1    1    0.343531    0.540882   -0.103548    11.00000    0.03732    0.05696 =
         0.03679    0.01322    0.00360    0.02407
AFIX  43
H1    2    0.237709    0.569668   -0.172684    11.00000   -1.20000
AFIX   0
C2    1    0.347953    0.622788    0.042194    11.00000    0.03686    0.04921 =
         0.04077    0.00815    0.00689    0.02435
AFIX  43
H2    2    0.244007    0.705464    0.069925    11.00000   -1.20000
AFIX   0
C5    1    0.731000    0.789098    0.555979    11.00000    0.04129    0.06941 =
         0.03435    0.00707    0.01049    0.02395
AFIX  23
H5A   2    0.574969    0.709370    0.585197    11.00000   -1.20000
H5B   2    0.707331    0.914236    0.572799    11.00000   -1.20000
AFIX   0
C6    1    0.999447    0.809765    0.647206    11.00000    0.05725    0.07075 =
         0.03957    0.01503    0.00838    0.02917
AFIX  23
H6A   2    1.156178    0.886032    0.616087    11.00000   -1.20000
H6B   2    1.020166    0.684219    0.633235    11.00000   -1.20000
AFIX   0
C7    1    1.009814    0.903946    0.807094    11.00000    0.07657    0.07826 =
         0.03533    0.00837    0.00498    0.02246
AFIX 137
H7A   2    0.983381    1.026582    0.821015    11.00000   -1.50000
H7B   2    1.189562    0.920572    0.861480    11.00000   -1.50000
H7C   2    0.863061    0.824312    0.840015    11.00000   -1.50000
AFIX   0
HKLF 4

REM  3jula_0m_a.res in P-1
REM R1 =  0.0673 for     757 Fo > 4sig(Fo)  and  0.1157 for all    1205 data
REM     83 parameters refined using      0 restraints

END

WGHT      0.0555      0.1597

REM Highest difference peak  0.181,  deepest hole -0.293,  1-sigma level  0.051
Q1    1   1.2329  0.9663  0.6159  11.00000  0.05    0.18
Q2    1   0.8949  0.7977  0.3783  11.00000  0.05    0.17
Q3    1   1.3627  1.1037  0.7142  11.00000  0.05    0.16
Q4    1   0.5893  0.5648  0.5775  11.00000  0.05    0.15
Q5    1   0.7907  0.7206  0.6509  11.00000  0.05    0.14
Q6    1   0.4853  1.0040  0.6392  11.00000  0.05    0.14
Q7    1   0.4627  0.6190  0.6413  11.00000  0.05    0.14
Q8    1   0.6316  0.7979  0.1232  11.00000  0.05    0.14
Q9    1   1.1611  0.7782  0.6026  11.00000  0.05    0.13
Q10   1   1.1704  1.0697  0.8025  11.00000  0.05    0.13
Q11   1   1.1031  1.0270  0.6185  11.00000  0.05    0.13
Q12   1   0.0644  0.7762  0.1690  11.00000  0.05    0.13
Q13   1   0.6947  0.5975  0.6173  11.00000  0.05    0.13
Q14   1   1.3283  1.0730  0.7994  11.00000  0.05    0.12
Q15   1   1.1522  1.2814  0.8832  11.00000  0.05    0.12
Q16   1   0.6081  0.5548  0.4063  11.00000  0.05    0.12
Q17   1   0.6207  0.6427  0.7161  11.00000  0.05    0.12
Q18   1   0.6737  1.0029  0.4738  11.00000  0.05    0.12
Q19   1   0.3173  0.5015  0.0927  11.00000  0.05    0.12
Q20   1   0.4683  0.9086  0.3803  11.00000  0.05    0.12
;
_shelx_res_checksum              54400
####################################################################### 
# 
# 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_27juna_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1903354'
loop_
_audit_author_name
_audit_author_address
'Dr. Meenu Teotia'
;Ch. Charan Singh University Meerut UP India
India
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.0619(16)
_cell_length_b                   5.1565(17)
_cell_length_c                   13.593(4)
_cell_angle_alpha                100.634(8)
_cell_angle_beta                 96.239(8)
_cell_angle_gamma                95.839(8)
_cell_volume                     343.93(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_F_000             132
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3501
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.076
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_full        25.048
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1191
_reflns_number_gt                723
_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_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1191
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1488
_refine_ls_goodness_of_fit_ref   1.307
_refine_ls_restrained_S_all      1.307
_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
O1 O 0.2303(4) 0.4434(4) 0.69638(15) 0.0558(8) Uani 1 1 d . . . . .
N1 N 0.6763(4) 0.5541(5) 0.72144(17) 0.0467(7) Uani 1 1 d . . . . .
H1A H 0.8276 0.5228 0.7015 0.056 Uiso 1 1 calc R U . . .
C2 C 0.4841(5) 0.1976(6) 0.5832(2) 0.0355(8) Uani 1 1 d . . . . .
C4 C 0.4541(6) 0.4069(6) 0.6717(2) 0.0405(8) Uani 1 1 d . . . . .
C1 C 0.3036(5) -0.0307(6) 0.5601(2) 0.0427(8) Uani 1 1 d . . . . .
H1 H 0.1692 -0.0525 0.6005 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6801(5) 0.2258(6) 0.5216(2) 0.0427(8) Uani 1 1 d . . . . .
H3 H 0.8027 0.3791 0.5357 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6734(6) 0.7655(6) 0.8080(2) 0.0525(9) Uani 1 1 d . . . . .
H5 H 0.5205 0.8610 0.7935 0.063 Uiso 1 1 calc R U . . .
C6 C 0.9223(7) 0.9594(7) 0.8239(3) 0.0906(14) Uani 1 1 d . . . . .
H6A H 1.0754 0.8711 0.8390 0.136 Uiso 1 1 calc R U . . .
H6B H 0.9126 1.1026 0.8791 0.136 Uiso 1 1 calc R U . . .
H6C H 0.9387 1.0289 0.7637 0.136 Uiso 1 1 calc R U . . .
C7 C 0.6365(10) 0.6560(8) 0.9017(3) 0.1044(15) Uani 1 1 d . . . . .
H7A H 0.4835 0.5225 0.8879 0.157 Uiso 1 1 calc R U . . .
H7B H 0.6093 0.7972 0.9550 0.157 Uiso 1 1 calc R U . . .
H7C H 0.7933 0.5786 0.9218 0.157 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0293(12) 0.0667(15) 0.0677(16) -0.0040(12) 0.0139(10) 0.0112(11)
N1 0.0314(15) 0.0544(16) 0.0496(16) -0.0072(14) 0.0082(12) 0.0122(12)
C2 0.0285(16) 0.0429(18) 0.0369(17) 0.0088(15) 0.0027(13) 0.0122(15)
C4 0.0314(17) 0.0456(19) 0.0457(19) 0.0103(16) 0.0043(14) 0.0095(15)
C1 0.0318(17) 0.055(2) 0.0433(19) 0.0072(17) 0.0148(13) 0.0079(16)
C3 0.0366(17) 0.0440(19) 0.047(2) 0.0048(17) 0.0114(14) 0.0034(14)
C5 0.0410(19) 0.058(2) 0.054(2) -0.0038(19) 0.0074(15) 0.0123(17)
C6 0.071(3) 0.073(3) 0.113(3) -0.020(3) 0.020(2) 0.004(2)
C7 0.149(4) 0.098(3) 0.064(3) 0.004(3) 0.021(3) 0.017(3)

_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 C4 1.239(3) . ?
N1 C4 1.331(3) . ?
N1 C5 1.451(3) . ?
N1 H1A 0.8600 . ?
C2 C1 1.379(3) . ?
C2 C3 1.380(4) . ?
C2 C4 1.492(4) . ?
C1 C3 1.370(4) 2_656 ?
C1 H1 0.9300 . ?
C3 C1 1.370(4) 2_656 ?
C3 H3 0.9300 . ?
C5 C6 1.496(4) . ?
C5 C7 1.507(5) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C5 122.6(2) . . ?
C4 N1 H1A 118.7 . . ?
C5 N1 H1A 118.7 . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 C4 118.8(2) . . ?
C3 C2 C4 122.8(3) . . ?
O1 C4 N1 121.7(3) . . ?
O1 C4 C2 121.0(3) . . ?
N1 C4 C2 117.3(2) . . ?
C3 C1 C2 120.8(3) 2_656 . ?
C3 C1 H1 119.6 2_656 . ?
C2 C1 H1 119.6 . . ?
C1 C3 C2 120.8(3) 2_656 . ?
C1 C3 H3 119.6 2_656 . ?
C2 C3 H3 119.6 . . ?
N1 C5 C6 110.6(3) . . ?
N1 C5 C7 111.4(3) . . ?
C6 C5 C7 111.2(3) . . ?
N1 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C7 C5 H5 107.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.050

_shelx_res_file                  
;

    27juna_0m_a.res created by SHELXL-2014/7

TITL 27juna_0m_a.res in P-1
CELL  0.71073   5.0619   5.1565  13.5927  100.634   96.239   95.839
ZERR    1.000   0.0016   0.0017   0.0044    0.008    0.008    0.008
LATT 1
SFAC C  H  N  O
UNIT 14  18  2  2
OMIT -2 50.1
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 5
TEMP 23.000
WGHT    0.065300
FVAR       1.87848
O1    4    0.230326    0.443445    0.696376    11.00000    0.02927    0.06671 =
         0.06770   -0.00395    0.01394    0.01120
N1    3    0.676325    0.554130    0.721443    11.00000    0.03142    0.05442 =
         0.04957   -0.00723    0.00824    0.01224
AFIX  43
H1A   2    0.827594    0.522815    0.701543    11.00000   -1.20000
AFIX   0
C2    1    0.484124    0.197584    0.583240    11.00000    0.02853    0.04286 =
         0.03689    0.00884    0.00268    0.01220
C4    1    0.454100    0.406862    0.671663    11.00000    0.03143    0.04561 =
         0.04568    0.01029    0.00434    0.00954
C1    1    0.303642   -0.030739    0.560092    11.00000    0.03184    0.05460 =
         0.04331    0.00717    0.01478    0.00794
AFIX  43
H1    2    0.169233   -0.052539    0.600456    11.00000   -1.20000
AFIX   0
C3    1    0.680140    0.225812    0.521609    11.00000    0.03663    0.04402 =
         0.04670    0.00479    0.01141    0.00340
AFIX  43
H3    2    0.802701    0.379105    0.535705    11.00000   -1.20000
AFIX   0
C5    1    0.673397    0.765498    0.807992    11.00000    0.04100    0.05827 =
         0.05397   -0.00383    0.00742    0.01235
AFIX  13
H5    2    0.520453    0.860956    0.793543    11.00000   -1.20000
AFIX   0
C6    1    0.922312    0.959404    0.823861    11.00000    0.07137    0.07318 =
         0.11300   -0.01964    0.01982    0.00363
AFIX 137
H6A   2    1.075376    0.871130    0.839013    11.00000   -1.50000
H6B   2    0.912576    1.102562    0.879075    11.00000   -1.50000
H6C   2    0.938686    1.028930    0.763675    11.00000   -1.50000
AFIX   0
C7    1    0.636505    0.656021    0.901673    11.00000    0.14881    0.09801 =
         0.06361    0.00380    0.02071    0.01700
AFIX 137
H7A   2    0.483453    0.522506    0.887855    11.00000   -1.50000
H7B   2    0.609279    0.797162    0.955005    11.00000   -1.50000
H7C   2    0.793279    0.578648    0.921843    11.00000   -1.50000
AFIX   0
HKLF 4

REM  27juna_0m_a.res in P-1
REM R1 =  0.0741 for     723 Fo > 4sig(Fo)  and  0.1386 for all    1191 data
REM     84 parameters refined using      0 restraints

END

WGHT      0.0428      0.3585

REM Highest difference peak  0.186,  deepest hole -0.229,  1-sigma level  0.050
Q1    1   1.0000  1.0000  1.0000  10.50000  0.05    0.19
Q2    1   0.1751  0.4128  0.7959  11.00000  0.05    0.17
Q3    1   0.5880  0.6793  0.8878  11.00000  0.05    0.16
Q4    1   0.9424  0.9930  0.9454  11.00000  0.05    0.15
Q5    1   0.0271  0.2377  0.6620  11.00000  0.05    0.15
;
_shelx_res_checksum              67582
