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

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

data_OMePh-NH_NMe-Me
_database_code_depnum_ccdc_archive 'CCDC 1959997'
loop_
_audit_author_name
_audit_author_address
'JUGAL KISHORE RAI DEKA'
;Shiv Nadar University
India
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_audit_creation_date             2019-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 N2 O3, H2 O'
_chemical_formula_sum            'C11 H16 N2 O4'
_chemical_formula_weight         240.26
_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                   6.8265(12)
_cell_length_b                   7.2475(13)
_cell_length_c                   13.022(2)
_cell_angle_alpha                87.473(5)
_cell_angle_beta                 79.192(6)
_cell_angle_gamma                79.227(5)
_cell_volume                     621.66(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5616
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.151
_exptl_transmission_factor_max   0.983
_exptl_transmission_factor_min   0.978
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13404
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.090
_diffrn_ambient_temperature      299.09
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   X-ray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1696
_reflns_number_total             2179
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      1.073
_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)+(0.0974P)²+0.2375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.1923
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C10A-O3A
 1.25 with sigma of 0.025
3. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
4. Others
 Sof(O3A)=1-FVAR(1)
 Sof(O3)=FVAR(1)
 Sof(N1A)=1-FVAR(2)
 Sof(N1)=FVAR(2)
 Fixed Sof: H1A(0.35) H9AA(0.65) H9AB(0.65) H9AC(0.65) H9BD(0.35) H9BE(0.35)
 H9BF(0.35) N2A(0.65) C10A(0.35) C10B(0.65) N2B(0.35) H1(0.65)
5.a Free rotating group:
 O4(H4A,H4B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C5(H5), C6(H6), C3(H3), C2(H2)
5.c Idealised Me refined as rotating group:
 C9(H9AA,H9AB,H9AC), C9(H9BD,H9BE,H9BF), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8474(3) 0.8140(3) 0.30379(13) 0.0732(6) Uani 1 1 d . . . . .
O2 O 0.1903(3) 0.6972(3) 0.69851(15) 0.0809(7) Uani 1 1 d . . . . .
O4 O -0.1659(3) 0.6641(4) 0.83492(17) 0.0950(9) Uani 1 1 d . . . . .
H4A H -0.156583 0.574683 0.879259 0.143 Uiso 1 1 d G . . . .
H4B H -0.047977 0.675289 0.803066 0.143 Uiso 1 1 d G . . . .
O3 O 0.172(3) 0.678(4) 1.0292(11) 0.062(3) Uani 0.55(10) 1 d . . P A 1
N1 N 0.4580(12) 0.659(4) 0.7796(6) 0.062(4) Uani 0.88(6) 1 d . U P A 1
H1A H 0.579962 0.598641 0.775793 0.075 Uiso 0.35 1 calc R . P A 2
C1 C 0.7461(4) 0.7798(3) 0.40108(17) 0.0521(6) Uani 1 1 d . . . . .
C4 C 0.5091(3) 0.7202(3) 0.59408(17) 0.0484(6) Uani 1 1 d . . . . .
C5 C 0.4241(4) 0.7577(4) 0.50520(19) 0.0574(7) Uani 1 1 d . . . . .
H5 H 0.285596 0.762608 0.509959 0.069 Uiso 1 1 calc R . . . .
C6 C 0.5402(4) 0.7876(4) 0.41055(19) 0.0605(7) Uani 1 1 d . . . . .
H6 H 0.479663 0.813406 0.351954 0.073 Uiso 1 1 calc R . . . .
C3 C 0.7158(4) 0.7103(4) 0.58351(19) 0.0586(7) Uani 1 1 d . . . . .
H3 H 0.776575 0.684287 0.642025 0.070 Uiso 1 1 calc R . . . .
C11 C 0.3718(4) 0.6938(4) 0.6939(2) 0.0590(7) Uani 1 1 d . . . . .
C2 C 0.8337(4) 0.7381(4) 0.4883(2) 0.0617(7) Uani 1 1 d . . . . .
H2 H 0.973024 0.728844 0.482821 0.074 Uiso 1 1 calc R . . . .
C9 C 0.3394(5) 0.3959(4) 0.8880(2) 0.0688(8) Uani 1 1 d . . . . .
H9AA H 0.301939 0.348459 0.828172 0.103 Uiso 0.65 1 calc GR . P B 1
H9AB H 0.241240 0.379110 0.949229 0.103 Uiso 0.65 1 calc GR . P B 1
H9AC H 0.470576 0.328938 0.896795 0.103 Uiso 0.65 1 calc GR . P B 1
H9BD H 0.314356 0.297661 0.937880 0.103 Uiso 0.35 1 calc GR . P C 2
H9BE H 0.480755 0.375585 0.856983 0.103 Uiso 0.35 1 calc GR . P C 2
H9BF H 0.260041 0.395434 0.834477 0.103 Uiso 0.35 1 calc GR . P C 2
C7 C 1.0568(4) 0.8220(6) 0.2917(2) 0.0845(10) Uani 1 1 d . . . . .
H7A H 1.109322 0.845691 0.219569 0.127 Uiso 1 1 calc GR . . . .
H7B H 1.128866 0.704575 0.313428 0.127 Uiso 1 1 calc GR . . . .
H7C H 1.073805 0.921318 0.333766 0.127 Uiso 1 1 calc GR . . . .
N2A N 0.3462(5) 0.5930(7) 0.8726(3) 0.0544(8) Uani 0.65 1 d . . P A 1
C10A C 0.2828(12) 0.5786(15) 0.9411(8) 0.0543(17) Uani 0.35 1 d D . P A 2
C10B C 0.2645(7) 0.7218(8) 0.9475(4) 0.0546(9) Uani 0.65 1 d . . P A .
N2B N 0.3317(10) 0.7319(12) 0.8817(7) 0.0560(16) Uani 0.35 1 d . . P A .
H1 H 0.594(6) 0.692(5) 0.782(3) 0.049(9) Uiso 0.65 1 d . . P . .
O3A O 0.185(4) 0.613(9) 1.0333(14) 0.084(6) Uani 0.45(10) 1 d D . P A 2
N1A N 0.448(7) 0.740(13) 0.787(3) 0.058(9) Uani 0.12(6) 1 d . . P A 2
C8 C 0.2856(7) 0.9208(5) 0.9236(3) 0.0778(9) Uani 1 1 d . . . . .
H8A H 0.429(7) 0.931(5) 0.906(3) 0.114(13) Uiso 1 1 d . . . . .
H8B H 0.229(7) 0.976(6) 0.992(4) 0.123(14) Uiso 1 1 d . . . . .
H8C H 0.204(7) 0.966(6) 0.883(4) 0.125(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.361(3) . ?
O1 C7 1.420(3) . ?
O2 C11 1.225(3) . ?
O3 C10B 1.193(17) . ?
N1 C11 1.349(5) . ?
N1 N2A 1.422(7) . ?
N1 N2B 1.500(18) . ?
C1 C6 1.378(3) . ?
C1 C2 1.377(3) . ?
C4 C5 1.384(3) . ?
C4 C3 1.380(3) . ?
C4 C11 1.481(3) . ?
C5 C6 1.367(3) . ?
C3 C2 1.375(3) . ?
C11 N1A 1.47(6) . ?
C9 N2A 1.442(6) . ?
C9 C10A 1.473(12) . ?
N2A C10B 1.347(7) . ?
N2A N2B 1.003(7) . ?
C10A C10B 1.027(9) . ?
C10A N2B 1.382(11) . ?
C10A O3A 1.27(2) . ?
C10B N2B 0.900(7) . ?
C10B O3A 1.42(4) . ?
C10B C8 1.489(7) . ?
N2B N1A 1.34(5) . ?
N2B C8 1.453(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 118.2(2) . . ?
C11 N1 N2A 119.4(4) . . ?
C11 N1 N2B 117.1(11) . . ?
N2A N1 N2B 40.1(4) . . ?
O1 C1 C6 116.1(2) . . ?
O1 C1 C2 125.1(2) . . ?
C2 C1 C6 118.9(2) . . ?
C5 C4 C11 117.6(2) . . ?
C3 C4 C5 117.7(2) . . ?
C3 C4 C11 124.6(2) . . ?
C6 C5 C4 121.1(2) . . ?
C5 C6 C1 120.7(2) . . ?
C2 C3 C4 121.4(2) . . ?
O2 C11 N1 121.3(3) . . ?
O2 C11 C4 122.1(2) . . ?
O2 C11 N1A 120.2(18) . . ?
N1 C11 C4 116.5(3) . . ?
N1A C11 C4 113(3) . . ?
C3 C2 C1 120.2(2) . . ?
N1 N2A C9 121.0(11) . . ?
C10B N2A N1 115.9(12) . . ?
C10B N2A C9 122.9(5) . . ?
N2B N2A N1 74.2(13) . . ?
N2B N2A C9 164.8(7) . . ?
N2B N2A C10B 41.9(4) . . ?
C10B C10A C9 156.6(10) . . ?
C10B C10A N2B 40.6(5) . . ?
C10B C10A O3A 76(3) . . ?
N2B C10A C9 116.2(10) . . ?
O3A C10A C9 127(3) . . ?
O3A C10A N2B 116(3) . . ?
O3 C10B N2A 120.5(13) . . ?
O3 C10B C8 121.3(12) . . ?
N2A C10B C8 118.1(6) . . ?
C10A C10B O3A 60(2) . . ?
C10A C10B C8 161.1(9) . . ?
N2B C10B O3 168.3(14) . . ?
N2B C10B N2A 48.1(6) . . ?
N2B C10B C10A 91.4(8) . . ?
N2B C10B O3A 151(2) . . ?
N2B C10B C8 70.0(8) . . ?
O3A C10B C8 139(2) . . ?
N2A N2B N1 65.8(11) . . ?
N2A N2B C8 164.4(9) . . ?
C10A N2B C8 122.3(10) . . ?
C10B N2B N1 155.3(13) . . ?
C10B N2B N2A 90.0(8) . . ?
C10B N2B C10A 48.0(6) . . ?
C10B N2B N1A 175(2) . . ?
C10B N2B C8 74.4(9) . . ?
N1A N2B C10A 130(4) . . ?
N1A N2B C8 107(4) . . ?
C8 N2B N1 129.7(10) . . ?
C10A O3A C10B 44.4(10) . . ?
N2B N1A C11 119(5) . . ?
N2B C8 C10B 35.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ph-NH_NMe-Me
_database_code_depnum_ccdc_archive 'CCDC 1978593'
loop_
_audit_author_name
_audit_author_address
'JUGAL KISHORE RAI DEKA'
;Shiv Nadar University
India
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-03-30 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         'C10 H12 N2 O2'
_chemical_formula_sum            'C10 H12 N2 O2'
_chemical_formula_weight         192.22

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   8.8720(4)
_cell_length_b                   12.3858(7)
_cell_length_c                   9.6316(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1058.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4247
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   0.980
_exptl_transmission_factor_max   0.990
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.155
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14257
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.824
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             2021
_reflns_number_gt                1699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.937
_reflns_Friedel_fraction_full    0.944

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0563P)²+0.2322P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 643 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2021
_refine_ls_number_parameters     133
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.6241(2) 0.18918(19) 0.4287(3) 0.0618(6) Uani 1 1 d . . . . .
O2 O 0.6392(4) 0.4458(3) 0.1554(3) 0.0907(9) Uani 1 1 d . . . . .
N1 N 0.4394(3) 0.3106(3) 0.4125(3) 0.0704(9) Uani 1 1 d . . . . .
C7 C 0.5107(3) 0.2295(2) 0.4768(3) 0.0494(7) Uani 1 1 d . . . . .
C1 C 0.4406(3) 0.1911(2) 0.6086(3) 0.0477(7) Uani 1 1 d . . . . .
N2 N 0.4871(3) 0.3433(3) 0.2799(4) 0.0742(9) Uani 1 1 d . . . . .
C6 C 0.3427(4) 0.2525(3) 0.6862(3) 0.0584(8) Uani 1 1 d . . . . .
H6 H 0.3200 0.3226 0.6585 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2780(4) 0.2111(4) 0.8046(4) 0.0752(10) Uani 1 1 d . . . . .
H5 H 0.2114 0.2528 0.8565 0.090 Uiso 1 1 calc R U . . .
C2 C 0.4776(4) 0.0882(3) 0.6528(4) 0.0696(10) Uani 1 1 d . . . . .
H2 H 0.5466 0.0469 0.6031 0.084 Uiso 1 1 calc R U . . .
C9 C 0.5899(4) 0.4205(3) 0.2694(4) 0.0693(10) Uani 1 1 d . . . . .
C4 C 0.3123(5) 0.1076(4) 0.8458(5) 0.0872(13) Uani 1 1 d . . . . .
H4 H 0.2678 0.0788 0.9250 0.105 Uiso 1 1 calc R U . . .
C8 C 0.4359(6) 0.2806(4) 0.1632(5) 0.1026(16) Uani 1 1 d . . . . .
H8A H 0.4526 0.3204 0.0791 0.154 Uiso 1 1 calc R U . . .
H8B H 0.3302 0.2658 0.1732 0.154 Uiso 1 1 calc R U . . .
H8C H 0.4906 0.2138 0.1596 0.154 Uiso 1 1 calc R U . . .
C3 C 0.4113(6) 0.0474(3) 0.7710(5) 0.0911(13) Uani 1 1 d . . . . .
H3 H 0.4346 -0.0222 0.8000 0.109 Uiso 1 1 calc R U . . .
C10 C 0.6407(5) 0.4749(4) 0.4016(5) 0.0866(13) Uani 1 1 d . . . . .
H10A H 0.7223 0.5234 0.3814 0.130 Uiso 1 1 calc R U . . .
H10B H 0.6740 0.4212 0.4667 0.130 Uiso 1 1 calc R U . . .
H10C H 0.5582 0.5148 0.4408 0.130 Uiso 1 1 calc R U . . .
H50 H 0.334(4) 0.326(3) 0.430(5) 0.074(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.215(3) . ?
O2 C9 1.222(5) . ?
N1 C7 1.339(4) . ?
N1 N2 1.405(4) . ?
N1 H50 0.97(4) . ?
C7 C1 1.491(4) . ?
C1 C6 1.375(4) . ?
C1 C2 1.384(4) . ?
N2 C9 1.326(5) . ?
N2 C8 1.439(6) . ?
C6 C5 1.376(5) . ?
C6 H6 0.9300 . ?
C5 C4 1.376(6) . ?
C5 H5 0.9300 . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C9 C10 1.509(6) . ?
C4 C3 1.359(6) . ?
C4 H4 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C3 H3 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C7 N1 N2 119.6(3) . . ?
C7 N1 H50 122(2) . . ?
N2 N1 H50 113(3) . . ?
O1 C7 N1 121.5(3) . . ?
O1 C7 C1 122.6(3) . . ?
N1 C7 C1 115.8(2) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 C7 123.4(3) . . ?
C2 C1 C7 117.1(3) . . ?
C9 N2 N1 119.0(4) . . ?
C9 N2 C8 123.2(4) . . ?
N1 N2 C8 117.3(3) . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
O2 C9 N2 119.9(4) . . ?
O2 C9 C10 122.4(4) . . ?
N2 C9 C10 117.6(3) . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.028

####################################################################### 
# 
# 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_NMe2Ph-NH_NMe-Me
_database_code_depnum_ccdc_archive 'CCDC 1961775'
loop_
_audit_author_name
_audit_author_address
'JUGAL KISHORE RAI DEKA'
;Shiv Nadar University
India
;
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_audit_creation_date             2019-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 N3 O2'
_chemical_formula_sum            'C12 H10 N3 O2'
_chemical_formula_weight         235.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   9.9477(5)
_cell_length_b                   7.5082(5)
_cell_length_c                   16.9603(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1266.75(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2094
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.90
_cell_measurement_theta_min      3.16
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.155
_exptl_transmission_factor_max   0.985
_exptl_transmission_factor_min   0.979
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8791
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.402
_diffrn_ambient_temperature      297.05
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   X-ray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                884
_reflns_number_total             1199
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.087
_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)+(0.0643P)²+0.3818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1534
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H8A(0.5) H8B(0.5) H8C(0.5) H7C(0.5) H7B(0.5) H7A(0.5) N0AA(0.5)
 C1AA(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2A), C6(H6)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7C,H7B,H7A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.5681(3) 0.250000 0.02928(12) 0.1053(10) Uani 1 2 d S T P . .
N2 N 0.4985(2) 0.250000 0.22910(13) 0.0873(11) Uani 1 2 d S T P . .
N1 N 0.4841(3) 0.250000 0.60834(14) 0.0785(9) Uani 1 2 d S T P . .
O1 O 0.7161(2) 0.250000 0.25808(13) 0.1358(15) Uani 1 2 d S T P . .
C1 C 0.5103(3) 0.250000 0.52893(15) 0.0587(8) Uani 1 2 d S T P . .
C4 C 0.5644(3) 0.250000 0.36583(15) 0.0577(7) Uani 1 2 d S T P . .
C3 C 0.4347(3) 0.250000 0.39408(15) 0.0654(8) Uani 1 2 d S T P . .
H3 H 0.363513 0.250000 0.358516 0.079 Uiso 1 2 calc RS T P . .
C5 C 0.6670(3) 0.250000 0.42095(16) 0.0726(10) Uani 1 2 d S T P . .
H5 H 0.755685 0.250000 0.403614 0.087 Uiso 1 2 calc RS T P . .
C2 C 0.4078(3) 0.250000 0.47363(15) 0.0664(9) Uani 1 2 d S T P . .
H2A H 0.318893 0.250000 0.490650 0.080 Uiso 1 2 calc RS T P . .
C6 C 0.6416(3) 0.250000 0.50039(16) 0.0723(9) Uani 1 2 d S T P . .
H6 H 0.713013 0.250000 0.535748 0.087 Uiso 1 2 calc RS T P . .
C9 C 0.6002(3) 0.250000 0.28186(16) 0.0820(11) Uani 1 2 d S T P . .
C8 C 0.3479(4) 0.250000 0.63757(19) 0.0951(12) Uani 1 2 d S T P . .
H8A H 0.292961 0.176306 0.604397 0.143 Uiso 0.5 1 calc GR . . A -1
H8B H 0.313530 0.369465 0.637354 0.143 Uiso 0.5 1 calc GR . . A -1
H8C H 0.346647 0.204230 0.690417 0.143 Uiso 0.5 1 calc GR . . A -1
C7 C 0.5906(4) 0.250000 0.66514(18) 0.1070(15) Uani 1 2 d S T P . .
H7C H 0.660211 0.169989 0.648291 0.160 Uiso 0.5 1 calc GR . . B -1
H7B H 0.556388 0.211918 0.715305 0.160 Uiso 0.5 1 calc GR . . B -1
H7A H 0.626731 0.368092 0.669901 0.160 Uiso 0.5 1 calc GR . . B -1
N0AA N 0.5229(3) 0.1790(5) 0.15055(19) 0.0625(11) Uani 0.5 1 d . . . . .
C1AA C 0.5433(4) 0.1884(6) 0.0980(2) 0.0664(17) Uani 0.5 1 d . . . . .
C0AA C 0.5326(5) -0.0034(5) 0.1281(2) 0.0993(10) Uani 1 1 d . . . . .
H2 H 0.409(4) 0.250000 0.245(2) 0.098(11) Uiso 1 2 d S T P . .
H0AA H 0.544(4) -0.047(6) 0.076(2) 0.177(16) Uiso 1 1 d . . . . .
H0AB H 0.611(4) -0.027(7) 0.160(2) 0.194(18) Uiso 1 1 d . . . . .
H0AC H 0.464(5) -0.031(10) 0.151(3) 0.24(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1AA 1.279(5) 7_565 ?
O2 C1AA 1.279(5) . ?
N2 C9 1.351(4) . ?
N2 N0AA 1.455(4) 7_565 ?
N2 N0AA 1.455(4) . ?
N1 C1 1.372(3) . ?
N1 C8 1.442(5) . ?
N1 C7 1.433(4) . ?
O1 C9 1.222(3) . ?
C1 C2 1.385(4) . ?
C1 C6 1.393(4) . ?
C4 C3 1.377(4) . ?
C4 C5 1.384(4) . ?
C4 C9 1.468(4) . ?
C3 C2 1.376(4) . ?
C5 C6 1.371(4) . ?
N0AA N0AA 1.066(7) 7_565 ?
N0AA C1AA 1.351(5) 7_565 ?
N0AA C1AA 0.916(4) . ?
N0AA C0AA 1.425(5) . ?
C1AA C1AA 0.926(9) 7_565 ?
C1AA C0AA 1.531(6) . ?

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
C1AA O2 C1AA 42.4(4) 7_565 . ?
C9 N2 N0AA 118.8(2) . . ?
C9 N2 N0AA 118.8(2) . 7_565 ?
N0AA N2 N0AA 43.0(3) 7_565 . ?
C1 N1 C8 121.1(3) . . ?
C1 N1 C7 121.3(3) . . ?
C7 N1 C8 117.6(3) . . ?
N1 C1 C2 121.7(3) . . ?
N1 C1 C6 121.3(3) . . ?
C2 C1 C6 117.1(2) . . ?
C3 C4 C5 117.1(2) . . ?
C3 C4 C9 124.4(2) . . ?
C5 C4 C9 118.5(2) . . ?
C2 C3 C4 121.6(3) . . ?
C6 C5 C4 121.9(3) . . ?
C3 C2 C1 121.4(3) . . ?
C5 C6 C1 121.0(3) . . ?
N2 C9 C4 117.5(2) . . ?
O1 C9 N2 119.2(3) . . ?
O1 C9 C4 123.3(3) . . ?
N0AA N0AA N2 68.52(15) 7_565 . ?
N0AA N0AA C1AA 42.5(2) 7_565 7_565 ?
N0AA N0AA C0AA 164.0(2) 7_565 . ?
C1AA N0AA N2 111.0(3) 7_565 . ?
C1AA N0AA N2 154.0(5) . . ?
C1AA N0AA N0AA 85.6(4) . 7_565 ?
C1AA N0AA C1AA 43.1(4) . 7_565 ?
C1AA N0AA C0AA 121.5(3) 7_565 . ?
C1AA N0AA C0AA 78.4(4) . . ?
C0AA N0AA N2 127.5(3) . . ?
O2 C1AA N0AA 111.3(4) . 7_565 ?
O2 C1AA C0AA 131.1(4) . . ?
N0AA C1AA O2 163.1(5) . . ?
N0AA C1AA N0AA 51.9(4) . 7_565 ?
N0AA C1AA C1AA 94.4(4) . 7_565 ?
N0AA C1AA C0AA 65.8(4) . . ?
N0AA C1AA C0AA 117.6(3) 7_565 . ?
C1AA C1AA O2 68.8(2) 7_565 . ?
C1AA C1AA N0AA 42.5(2) 7_565 7_565 ?
C1AA C1AA C0AA 160.1(2) 7_565 . ?
N0AA C0AA C1AA 35.88(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_NO2Ph-NH_NMe-Me
_database_code_depnum_ccdc_archive 'CCDC 1961776'
loop_
_audit_author_name
_audit_author_address
'JUGAL KISHORE RAI DEKA'
;Shiv Nadar University
India
;
_audit_update_record             
;
2019-10-28 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_audit_creation_date             2019-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N3 O4, H2 O'
_chemical_formula_sum            'C10 H13 N3 O5'
_chemical_formula_weight         255.23
_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                   6.7495(7)
_cell_length_b                   7.1820(7)
_cell_length_c                   14.8256(13)
_cell_angle_alpha                76.262(3)
_cell_angle_beta                 80.534(3)
_cell_angle_gamma                62.981(3)
_cell_volume                     620.58(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7008
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.186
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16668
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.835
_diffrn_ambient_temperature      297.93
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   X-ray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1864
_reflns_number_total             2438
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.071
_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)+(0.0536P)²+0.3300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(O1A) = Uanis(O1B)
Uanis(N1B) = Uanis(C1B)
2. Others
 Fixed Sof: O1B(0.5) N1B(0.5) C1A(0.5) C1B(0.5) N1A(0.5) O1A(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.1260(3) 0.8613(3) 0.37104(13) 0.0812(6) Uani 1 1 d . . . . .
O1 O 0.9346(3) 0.5906(4) 0.70066(12) 0.0866(7) Uani 1 1 d . . . . .
N2 N 0.3139(4) 0.8485(3) 0.36716(14) 0.0617(6) Uani 1 1 d . . . . .
O2 O 0.4195(4) 0.8802(4) 0.29514(13) 0.0999(8) Uani 1 1 d . . . . .
C8 C 0.3000(4) 0.7724(3) 0.53705(15) 0.0476(5) Uani 1 1 d . . . . .
C9 C 0.4016(4) 0.7129(4) 0.61964(15) 0.0486(5) Uani 1 1 d . . . . .
C4 C 0.6241(3) 0.6697(3) 0.61847(14) 0.0432(5) Uani 1 1 d . . . . .
C5 C 0.7423(4) 0.6906(3) 0.53372(15) 0.0469(5) Uani 1 1 d . . . . .
C7 C 0.4233(3) 0.7878(3) 0.45472(13) 0.0448(5) Uani 1 1 d . . . . .
C6 C 0.6427(4) 0.7496(3) 0.45118(15) 0.0495(5) Uani 1 1 d . . . . .
C3 C 0.7499(4) 0.5969(4) 0.70419(15) 0.0574(6) Uani 1 1 d . . . . .
O1B O 0.877(7) 0.337(7) 0.993(2) 0.086(4) Uani 0.5 1 d . . P . .
C2 C 0.6241(7) 0.7294(6) 0.9166(3) 0.0794(9) Uani 1 1 d . . . . .
C1 C 0.9134(9) 0.1693(6) 0.8645(3) 0.0979(13) Uani 1 1 d . . . . .
N1B N 0.7825(7) 0.3988(8) 0.8578(3) 0.0551(9) Uani 0.5 1 d . . P . .
C1A C 0.7498(9) 0.5037(10) 0.9307(4) 0.0566(14) Uani 0.5 1 d . . P . .
O4 O 0.2455(4) 0.5127(6) 0.83042(16) 0.1126(11) Uani 1 1 d . . . . .
C1B C 0.7073(8) 0.5501(9) 0.8695(3) 0.0551(9) Uani 0.5 1 d . . P . .
N1A N 0.8224(11) 0.3675(13) 0.9143(5) 0.0931(18) Uani 0.5 1 d . . P . .
O1A O 0.855(7) 0.378(7) 1.007(2) 0.086(4) Uani 0.5 1 d . . P . .
N1 N 0.6477(4) 0.5380(4) 0.78295(13) 0.0768(8) Uani 1 1 d . . . . .
H4A H 0.175(7) 0.582(7) 0.879(3) 0.144(17) Uiso 1 1 d . . . . .
H4B H 0.144(8) 0.519(7) 0.807(3) 0.151(17) Uiso 1 1 d . . . . .
H5 H 0.892(4) 0.665(4) 0.5339(16) 0.058(6) Uiso 1 1 d . . . . .
H6 H 0.723(4) 0.766(4) 0.3954(18) 0.065(7) Uiso 1 1 d . . . . .
H9 H 0.311(4) 0.704(4) 0.6753(17) 0.056(6) Uiso 1 1 d . . . . .
H8 H 0.144(4) 0.801(4) 0.5391(17) 0.064(7) Uiso 1 1 d . . . . .
H1 H 0.521(5) 0.530(5) 0.787(2) 0.098(10) Uiso 1 1 d . . . . .
H2A H 0.658(7) 0.827(7) 0.864(3) 0.150(16) Uiso 1 1 d . . . . .
H2B H 0.486(8) 0.768(7) 0.922(3) 0.152(19) Uiso 1 1 d . . . . .
H1A H 0.986(10) 0.163(9) 0.810(4) 0.20(3) Uiso 1 1 d . . . . .
H1B H 0.983(7) 0.069(7) 0.912(3) 0.146(16) Uiso 1 1 d . . . . .
H1C H 0.769(10) 0.159(9) 0.863(4) 0.21(3) Uiso 1 1 d . . . . .
H2C H 0.667(9) 0.719(9) 0.970(4) 0.20(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N2 1.222(3) . ?
O1 C3 1.219(3) . ?
N2 O2 1.217(3) . ?
N2 C7 1.474(3) . ?
C8 C9 1.383(3) . ?
C8 C7 1.371(3) . ?
C9 C4 1.387(3) . ?
C4 C5 1.388(3) . ?
C4 C3 1.498(3) . ?
C5 C6 1.376(3) . ?
C7 C6 1.373(3) . ?
C3 N1 1.336(3) . ?
O1B C1A 1.35(4) . ?
O1B N1A 1.22(3) . ?
C2 C1A 1.428(7) . ?
C2 C1B 1.451(7) . ?
C1 N1B 1.461(6) . ?
C1 N1A 1.582(9) . ?
N1B C1A 1.393(7) . ?
N1B C1B 1.013(6) . ?
N1B N1A 0.869(6) . ?
N1B N1 1.428(4) . ?
C1A C1B 0.933(7) . ?
C1A N1A 0.946(8) . ?
C1A O1A 1.34(4) . ?
C1B N1A 1.263(9) . ?
C1B N1 1.439(5) . ?
N1A O1A 1.45(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
O3 N2 C7 118.6(2) . . ?
O2 N2 O3 124.2(2) . . ?
O2 N2 C7 117.2(2) . . ?
C7 C8 C9 118.8(2) . . ?
C8 C9 C4 120.2(2) . . ?
C9 C4 C5 119.32(19) . . ?
C9 C4 C3 123.90(18) . . ?
C5 C4 C3 116.77(18) . . ?
C6 C5 C4 120.9(2) . . ?
C8 C7 N2 118.23(19) . . ?
C8 C7 C6 122.47(19) . . ?
C6 C7 N2 119.29(19) . . ?
C7 C6 C5 118.3(2) . . ?
O1 C3 C4 121.3(2) . . ?
O1 C3 N1 123.1(2) . . ?
N1 C3 C4 115.64(18) . . ?
N1A O1B C1A 42.9(14) . . ?
C1A C2 C1B 37.8(3) . . ?
N1B C1 N1A 32.9(2) . . ?
C1A N1B C1 123.2(4) . . ?
C1A N1B N1 111.2(4) . . ?
C1B N1B C1 165.1(5) . . ?
C1B N1B C1A 42.1(4) . . ?
C1B N1B N1 69.9(4) . . ?
N1A N1B C1 81.3(7) . . ?
N1A N1B C1A 41.9(6) . . ?
N1A N1B C1B 83.9(7) . . ?
N1A N1B N1 152.6(8) . . ?
N1 N1B C1 125.0(4) . . ?
O1B C1A C2 141.8(12) . . ?
O1B C1A N1B 98.9(11) . . ?
N1B C1A C2 119.1(5) . . ?
C1B C1A O1B 145.1(13) . . ?
C1B C1A C2 72.4(6) . . ?
C1B C1A N1B 46.7(4) . . ?
C1B C1A N1A 84.5(8) . . ?
C1B C1A O1A 160.6(14) . . ?
N1A C1A O1B 61.0(12) . . ?
N1A C1A C2 156.8(8) . . ?
N1A C1A N1B 37.9(5) . . ?
N1A C1A O1A 76.5(14) . . ?
O1A C1A O1B 16(2) . . ?
O1A C1A C2 126.4(13) . . ?
O1A C1A N1B 114.4(13) . . ?
N1B C1B C2 161.0(6) . . ?
N1B C1B N1A 43.1(4) . . ?
N1B C1B N1 68.7(4) . . ?
C1A C1B C2 69.8(6) . . ?
C1A C1B N1B 91.3(6) . . ?
C1A C1B N1A 48.2(5) . . ?
C1A C1B N1 157.3(7) . . ?
N1A C1B C2 117.9(6) . . ?
N1A C1B N1 111.5(6) . . ?
N1 C1B C2 129.6(4) . . ?
O1B N1A C1 118(2) . . ?
O1B N1A C1B 123(2) . . ?
O1B N1A O1A 12(3) . . ?
N1B N1A O1B 176(2) . . ?
N1B N1A C1 65.9(6) . . ?
N1B N1A C1A 100.2(10) . . ?
N1B N1A C1B 52.9(5) . . ?
N1B N1A O1A 164.2(19) . . ?
C1A N1A O1B 76.1(19) . . ?
C1A N1A C1 166.0(9) . . ?
C1A N1A C1B 47.3(6) . . ?
C1A N1A O1A 64.1(18) . . ?
C1B N1A C1 118.8(6) . . ?
C1B N1A O1A 111.3(18) . . ?
O1A N1A C1 129.9(17) . . ?
C1A O1A N1A 39.4(9) . . ?
C3 N1 N1B 117.8(2) . . ?
C3 N1 C1B 118.1(3) . . ?
N1B N1 C1B 41.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ph-NH_NMe-C2H5
_database_code_depnum_ccdc_archive 'CCDC 1960842'
loop_
_audit_author_name
_audit_author_address
'JUGAL KISHORE RAI DEKA'
;Shiv Nadar University
India
;
_audit_update_record             
;
2019-10-22 deposited with the CCDC.	2020-03-30 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         'C11 H14 N2 O2'
_chemical_formula_sum            'C11 H14 N2 O2'
_chemical_formula_weight         206.24

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   8.7406(12)
_cell_length_b                   13.897(2)
_cell_length_c                   9.5194(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1156.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2070
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      22.90

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   0.989
_exptl_transmission_factor_max   0.992
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17248
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2277
_reflns_number_gt                1348
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0633P)²+0.0585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2277
_refine_ls_number_parameters     143
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.3694(3) 0.1692(2) 0.4396(4) 0.0725(9) Uani 1 1 d . . . . .
N1 N 0.5688(5) 0.2670(3) 0.4021(4) 0.0722(12) Uani 1 1 d . . . . .
C7 C 0.4933(5) 0.2011(3) 0.4768(5) 0.0588(10) Uani 1 1 d . . . . .
O2 O 0.3619(5) 0.4131(3) 0.1730(5) 0.1197(16) Uani 1 1 d . . . . .
N2 N 0.5063(5) 0.3021(3) 0.2765(4) 0.0775(12) Uani 1 1 d . . . . .
C4 C 0.5699(5) 0.1692(3) 0.6084(5) 0.0589(11) Uani 1 1 d . . . . .
C5 C 0.6682(5) 0.2285(4) 0.6825(5) 0.0697(13) Uani 1 1 d . . . . .
H5 H 0.6878 0.2905 0.6505 0.084 Uiso 1 1 calc R U . . .
C9 C 0.4255(6) 0.3847(4) 0.2806(6) 0.0823(15) Uani 1 1 d . . . . .
C6 C 0.7365(6) 0.1962(5) 0.8028(6) 0.0867(15) Uani 1 1 d . . . . .
H6 H 0.8036 0.2356 0.8521 0.104 Uiso 1 1 calc R U . . .
C3 C 0.5375(6) 0.0792(4) 0.6581(6) 0.0841(15) Uani 1 1 d . . . . .
H3 H 0.4686 0.0399 0.6108 0.101 Uiso 1 1 calc R U . . .
C1 C 0.7052(7) 0.1054(6) 0.8498(6) 0.104(2) Uani 1 1 d . . . . .
H1 H 0.7516 0.0833 0.9317 0.124 Uiso 1 1 calc R U . . .
C10 C 0.4206(6) 0.4390(3) 0.4153(6) 0.0878(16) Uani 1 1 d . . . . .
H10A H 0.5245 0.4503 0.4470 0.105 Uiso 1 1 calc R U . . .
H10B H 0.3698 0.3999 0.4856 0.105 Uiso 1 1 calc R U . . .
C2 C 0.6082(8) 0.0472(5) 0.7795(7) 0.110(2) Uani 1 1 d . . . . .
H2 H 0.5888 -0.0146 0.8127 0.132 Uiso 1 1 calc R U . . .
C8 C 0.5155(8) 0.2399(5) 0.1536(6) 0.113(2) Uani 1 1 d . . . . .
H8A H 0.4268 0.1993 0.1500 0.169 Uiso 1 1 calc R U . . .
H8B H 0.6059 0.2009 0.1596 0.169 Uiso 1 1 calc R U . . .
H8C H 0.5200 0.2787 0.0702 0.169 Uiso 1 1 calc R U . . .
C11 C 0.3389(8) 0.5342(5) 0.4043(10) 0.138(3) Uani 1 1 d . . . . .
H11A H 0.3858 0.5725 0.3323 0.207 Uiso 1 1 calc R U . . .
H11B H 0.3453 0.5674 0.4926 0.207 Uiso 1 1 calc R U . . .
H11C H 0.2334 0.5234 0.3811 0.207 Uiso 1 1 calc R U . . .
H50 H 0.659(6) 0.287(3) 0.418(6) 0.084(17) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.223(5) . ?
N1 C7 1.335(6) . ?
N1 N2 1.402(5) . ?
N1 H50 0.85(5) . ?
C7 C4 1.487(6) . ?
O2 C9 1.231(6) . ?
N2 C9 1.348(6) . ?
N2 C8 1.457(8) . ?
C4 C3 1.366(6) . ?
C4 C5 1.385(6) . ?
C5 C6 1.367(7) . ?
C5 H5 0.9300 . ?
C9 C10 1.488(8) . ?
C6 C1 1.367(8) . ?
C6 H6 0.9300 . ?
C3 C2 1.384(8) . ?
C3 H3 0.9300 . ?
C1 C2 1.350(9) . ?
C1 H1 0.9300 . ?
C10 C11 1.508(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C2 H2 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C7 N1 N2 120.1(4) . . ?
C7 N1 H50 126(4) . . ?
N2 N1 H50 113(4) . . ?
O1 C7 N1 122.1(4) . . ?
O1 C7 C4 122.3(4) . . ?
N1 C7 C4 115.5(4) . . ?
C9 N2 N1 118.4(4) . . ?
C9 N2 C8 123.9(4) . . ?
N1 N2 C8 117.2(4) . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 C7 118.1(4) . . ?
C5 C4 C7 122.1(4) . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O2 C9 N2 119.1(5) . . ?
O2 C9 C10 122.7(5) . . ?
N2 C9 C10 118.2(4) . . ?
C1 C6 C5 119.4(5) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C4 C3 C2 119.5(6) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C1 C6 121.1(6) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C9 C10 C11 113.6(5) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C1 C2 C3 120.1(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.120
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.029

####################################################################### 
# 
# 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_CF3Ph-NH_NMe-Me
_database_code_depnum_ccdc_archive 'CCDC 1959998'
loop_
_audit_author_name
_audit_author_address
'JUGAL KISHORE RAI DEKA'
;Shiv Nadar University
India
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_audit_creation_date             2019-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 F3 N2 O2, H2 O'
_chemical_formula_sum            'C11 H13 F3 N2 O3'
_chemical_formula_weight         278.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.405(3)
_cell_length_b                   6.5909(10)
_cell_length_c                   14.669(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.691(5)
_cell_angle_gamma                90
_cell_volume                     1340.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2458
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.145
_exptl_transmission_factor_max   0.977
_exptl_transmission_factor_min   0.969
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.320
_diffrn_ambient_temperature      299.13
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   X-ray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1275
_reflns_number_total             2364
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2364
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.1387
_refine_ls_R_factor_gt           0.0782
_refine_ls_restrained_S_all      1.068
_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)+(0.1225P)²+1.1649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2132
_refine_ls_wR_factor_ref         0.2673
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1A-H1A
 0.9 with sigma of 0.05
 O1-H1C
 0.95 with sigma of 0.05
3. Uiso/Uaniso restraints and constraints
Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F3)
\\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1) \\sim Ueq: with sigma of 0.05 and
sigma for terminal atoms of 0.1
Uanis(F2) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1A)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.9 and
sigma for terminal atoms of 1.8
Uanis(O2B) \\sim Ueq, Uanis(O2A) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(N1B) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.01
Uanis(F2B) \\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(F1B) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(F1A) = Uanis(F1) = Uanis(F2A) = Uanis(F2) = Uanis(F3A) = Uanis(F3)
Uanis(O2B) = Uanis(O2A)
Uanis(N1B) = Uanis(N1A)
Uanis(C1B) = Uanis(C1A)
4. Others
 Fixed Sof: O2A(0.5) N1A(0.5) N2A(0.5) F3(0.4) F1(0.4) F2(0.4) F2A(0.4)
 F3A(0.4) F1A(0.4) N2B(0.5) C1A(0.5) C1B(0.5) O2B(0.5) N1B(0.5) F2B(0.2)
 F3B(0.2) F1B(0.2)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9)
5.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2A O 0.4701(5) 0.2267(17) 1.0082(8) 0.0745(17) Uani 0.5 1 d . U P . .
N1A N 0.4065(9) 0.414(4) 0.7774(17) 0.058(3) Uani 0.5 1 d D U P . .
C5 C 0.3940(3) 0.4351(6) 0.6136(3) 0.0569(10) Uani 1 1 d . . . . .
C10 C 0.4330(3) 0.6267(6) 0.6138(3) 0.0674(12) Uani 1 1 d . . . . .
H10 H 0.472972 0.678909 0.669555 0.095(15) Uiso 1 1 calc R . . . .
C8 C 0.3542(3) 0.6633(6) 0.4498(3) 0.0623(11) Uani 1 1 d . . . . .
C9 C 0.4134(3) 0.7406(6) 0.5326(3) 0.0687(12) Uani 1 1 d . . . . .
H9 H 0.439836 0.869446 0.533343 0.069(12) Uiso 1 1 calc R . . . .
C6 C 0.3377(3) 0.3565(7) 0.5299(3) 0.0696(12) Uani 1 1 d . . . . .
C7 C 0.3174(4) 0.4707(7) 0.4481(3) 0.0729(13) Uani 1 1 d . . . . .
C11 C 0.3257(5) 0.7910(9) 0.3628(4) 0.0931(17) Uani 1 1 d . . . . .
N2A N 0.3990(7) 0.3206(11) 0.8623(6) 0.0622(19) Uani 0.5 1 d . . P . .
F3 F 0.3634(7) 0.6854(16) 0.2931(7) 0.0963(12) Uani 0.4 1 d . U P . .
F1 F 0.3588(8) 0.9784(13) 0.3715(5) 0.0963(12) Uani 0.4 1 d . U P . .
F2 F 0.2283(7) 0.7805(18) 0.3201(7) 0.0963(12) Uani 0.4 1 d . U P . .
F2A F 0.2842(8) 0.9615(14) 0.3752(5) 0.0963(12) Uani 0.4 1 d . U P . .
F3A F 0.3182(9) 0.7135(15) 0.2861(7) 0.0963(12) Uani 0.4 1 d . U P . .
F1A F 0.4059(6) 0.9266(16) 0.3641(6) 0.0963(12) Uani 0.4 1 d . U P . .
N2B N 0.4722(7) 0.3119(10) 0.8701(6) 0.0601(18) Uani 0.5 1 d . . P . .
C1A C 0.4061(9) 0.2835(15) 0.9191(8) 0.067(2) Uani 0.5 1 d . . P . .
C1B C 0.4773(8) 0.2802(14) 0.9324(8) 0.067(2) Uani 0.5 1 d . . P . .
O2B O 0.4294(5) 0.2117(17) 1.0010(8) 0.0745(17) Uani 0.5 1 d . U P . .
N1B N 0.4459(9) 0.414(4) 0.7849(17) 0.058(3) Uani 0.5 1 d . U P . .
H6 H 0.312(4) 0.228(8) 0.533(3) 0.096(16) Uiso 1 1 d . . . . .
C3 C 0.5728(3) 0.2849(9) 0.9110(4) 0.0928(16) Uani 1 1 d . . . . .
H3A H 0.597762 0.192064 0.873011 0.139 Uiso 1 1 calc GR . . . .
H3B H 0.583644 0.231294 0.973822 0.139 Uiso 1 1 calc GR . . . .
H3C H 0.605031 0.413210 0.913686 0.139 Uiso 1 1 calc GR . . . .
C2 C 0.3028(4) 0.3178(9) 0.8729(4) 0.0956(17) Uani 1 1 d . . . . .
H2A H 0.284968 0.248138 0.813231 0.143 Uiso 1 1 calc GR . . . .
H2B H 0.291174 0.460493 0.862663 0.143 Uiso 1 1 calc GR . . . .
H2C H 0.265101 0.267037 0.912821 0.143 Uiso 1 1 calc GR . . . .
C1 C 0.4085(3) 0.3087(6) 0.7002(3) 0.0703(12) Uani 1 1 d . . . . .
H1A H 0.421(4) 0.546(6) 0.786(4) 0.106(18) Uiso 1 1 d D . . . .
F2B F 0.2408(10) 0.886(2) 0.3546(10) 0.067(3) Uani 0.2 1 d . U P . .
F3B F 0.2572(13) 0.714(2) 0.2901(9) 0.074(4) Uani 0.2 1 d . U P . .
F1B F 0.3914(13) 0.810(3) 0.3162(13) 0.096(4) Uani 0.2 1 d . U P . .
O1 O 0.4061(4) -0.1873(5) 0.8267(3) 0.1201(17) Uani 1 1 d D . . . .
H1B H 0.465(5) -0.174(12) 0.871(5) 0.16(3) Uiso 1 1 d . . . . .
H1C H 0.419(6) -0.072(10) 0.790(5) 0.20(3) Uiso 1 1 d D . . . .
O0AA O 0.4031(3) 0.1239(5) 0.6969(2) 0.0949(12) Uani 1 1 d . . . . .
H7 H 0.274(4) 0.417(8) 0.396(4) 0.106(18) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2A C1A 1.430(16) . ?
O2A C1B 1.198(14) . ?
O2A O2B 0.576(12) . ?
N1A N2A 1.42(3) . ?
N1A N2B 1.58(2) . ?
N1A N1B 0.55(2) . ?
N1A C1 1.33(3) . ?
C5 C10 1.382(5) . ?
C5 C6 1.376(5) . ?
C5 C1 1.487(5) . ?
C10 C9 1.371(5) . ?
C8 C9 1.378(6) . ?
C8 C7 1.373(6) . ?
C8 C11 1.491(6) . ?
C6 C7 1.380(6) . ?
C11 F3 1.457(11) . ?
C11 F1 1.318(10) . ?
C11 F2 1.375(10) . ?
C11 F2A 1.309(10) . ?
C11 F3A 1.214(10) . ?
C11 F1A 1.457(10) . ?
C11 F2B 1.349(14) . ?
C11 F3B 1.341(15) . ?
C11 F1B 1.314(15) . ?
N2A N2B 1.032(9) . ?
N2A C1A 0.848(10) . ?
N2A C1B 1.331(16) . ?
N2A N1B 1.59(3) . ?
F3 F3A 0.659(12) . ?
F3 F3B 1.530(19) . ?
F3 F1B 0.93(2) . ?
F1 F2A 1.096(10) . ?
F1 F1A 0.793(10) . ?
F1 F2B 1.759(16) . ?
F1 F1B 1.52(2) . ?
F2 F2A 1.540(13) . ?
F2 F3A 1.572(14) . ?
F2 F2B 0.848(14) . ?
F2 F3B 0.811(14) . ?
F2A F2B 0.793(13) . ?
F3A F3B 0.896(14) . ?
F3A F1B 1.21(2) . ?
F1A F1B 1.03(2) . ?
N2B C1A 1.352(16) . ?
N2B C1B 0.921(10) . ?
N2B N1B 1.38(2) . ?
N2B C3 1.422(11) . ?
C1A C1B 0.990(12) . ?
C1A O2B 1.250(14) . ?
C1A C2 1.477(13) . ?
C1B O2B 1.439(16) . ?
N1B C1 1.40(2) . ?
C1 O0AA 1.221(5) . ?
F2B F3B 1.53(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
C1B O2A C1A 43.1(7) . . ?
O2B O2A C1A 60.4(19) . . ?
O2B O2A C1B 103(2) . . ?
N2A N1A N2B 39.8(7) . . ?
N1B N1A N2A 98(5) . . ?
N1B N1A N2B 59(5) . . ?
N1B N1A C1 85(5) . . ?
C1 N1A N2A 122.9(18) . . ?
C1 N1A N2B 111.3(15) . . ?
C10 C5 C1 123.2(4) . . ?
C6 C5 C10 119.1(4) . . ?
C6 C5 C1 117.7(4) . . ?
C9 C10 C5 120.7(4) . . ?
C9 C8 C11 120.5(4) . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 C11 119.3(4) . . ?
C10 C9 C8 119.7(4) . . ?
C5 C6 C7 120.4(4) . . ?
C8 C7 C6 119.9(4) . . ?
F3 C11 C8 105.2(5) . . ?
F1 C11 C8 116.0(5) . . ?
F1 C11 F3 108.8(7) . . ?
F1 C11 F2 112.9(8) . . ?
F1 C11 F1A 32.7(4) . . ?
F1 C11 F2B 82.5(8) . . ?
F1 C11 F3B 126.9(8) . . ?
F2 C11 C8 111.9(5) . . ?
F2 C11 F3 100.7(7) . . ?
F2 C11 F1A 138.1(7) . . ?
F2A C11 C8 113.3(5) . . ?
F2A C11 F3 141.1(6) . . ?
F2A C11 F1 49.3(5) . . ?
F2A C11 F2 70.0(7) . . ?
F2A C11 F1A 82.1(6) . . ?
F2A C11 F2B 34.7(6) . . ?
F2A C11 F3B 99.8(9) . . ?
F2A C11 F1B 114.4(10) . . ?
F3A C11 C8 119.4(6) . . ?
F3A C11 F3 26.6(6) . . ?
F3A C11 F1 115.0(8) . . ?
F3A C11 F2 74.5(7) . . ?
F3A C11 F2A 124.1(8) . . ?
F3A C11 F1A 98.2(7) . . ?
F3A C11 F2B 105.1(9) . . ?
F3A C11 F3B 40.7(6) . . ?
F3A C11 F1B 56.9(10) . . ?
F1A C11 C8 107.5(5) . . ?
F1A C11 F3 81.8(6) . . ?
F2B C11 C8 111.8(7) . . ?
F2B C11 F3 131.3(9) . . ?
F2B C11 F2 36.3(6) . . ?
F2B C11 F1A 114.4(8) . . ?
F3B C11 C8 116.2(7) . . ?
F3B C11 F3 66.2(8) . . ?
F3B C11 F2 34.7(6) . . ?
F3B C11 F1A 130.7(8) . . ?
F3B C11 F2B 69.5(9) . . ?
F1B C11 C8 115.3(8) . . ?
F1B C11 F3 39.0(9) . . ?
F1B C11 F1 70.8(11) . . ?
F1B C11 F2 123.9(10) . . ?
F1B C11 F1A 43.1(10) . . ?
F1B C11 F2B 132.3(10) . . ?
F1B C11 F3B 95.7(11) . . ?
N1A N2A N1B 19.9(9) . . ?
N2B N2A N1A 78.6(9) . . ?
N2B N2A C1B 43.6(7) . . ?
N2B N2A N1B 58.8(8) . . ?
C1A N2A N1A 165.9(16) . . ?
C1A N2A N2B 91.5(14) . . ?
C1A N2A C1B 48.0(11) . . ?
C1A N2A N1B 148.1(16) . . ?
C1B N2A N1A 120.9(11) . . ?
C1B N2A N1B 101.1(11) . . ?
C11 F3 F3B 53.3(6) . . ?
F3A F3 C11 55.6(14) . . ?
F3A F3 F3B 11.8(14) . . ?
F3A F3 F1B 97.0(19) . . ?
F1B F3 C11 62.2(11) . . ?
F1B F3 F3B 103.4(14) . . ?
C11 F1 F2B 49.5(6) . . ?
C11 F1 F1B 54.5(8) . . ?
F2A F1 C11 64.9(7) . . ?
F2A F1 F2B 18.0(7) . . ?
F2A F1 F1B 113.6(12) . . ?
F1A F1 C11 83.3(11) . . ?
F1A F1 F2A 148.2(16) . . ?
F1A F1 F2B 131.4(14) . . ?
F1A F1 F1B 38.2(10) . . ?
F1B F1 F2B 95.5(10) . . ?
C11 F2 F2A 53.0(5) . . ?
C11 F2 F3A 48.1(5) . . ?
F2A F2 F3A 91.5(7) . . ?
F2B F2 C11 70.2(11) . . ?
F2B F2 F2A 19.6(11) . . ?
F2B F2 F3A 111.0(14) . . ?
F3B F2 C11 70.3(13) . . ?
F3B F2 F2A 115.5(16) . . ?
F3B F2 F3A 24.2(13) . . ?
F3B F2 F2B 135(2) . . ?
C11 F2A F2 57.0(6) . . ?
F1 F2A C11 65.7(7) . . ?
F1 F2A F2 115.6(9) . . ?
F2B F2A C11 75.4(13) . . ?
F2B F2A F1 136.6(17) . . ?
F2B F2A F2 21.0(13) . . ?
C11 F3A F2 57.4(6) . . ?
F3 F3A C11 97.8(16) . . ?
F3 F3A F2 153.5(17) . . ?
F3 F3A F3B 160(2) . . ?
F3 F3A F1B 50.2(14) . . ?
F3B F3A C11 77.3(12) . . ?
F3B F3A F2 21.8(11) . . ?
F3B F3A F1B 138.4(19) . . ?
F1B F3A C11 65.8(10) . . ?
F1B F3A F2 116.7(14) . . ?
F1 F1A C11 64.0(10) . . ?
F1 F1A F1B 113.2(16) . . ?
F1B F1A C11 61.0(10) . . ?
N2A N2B N1A 61.7(9) . . ?
N2A N2B C1A 38.8(7) . . ?
N2A N2B N1B 81.4(10) . . ?
N2A N2B C3 161.6(9) . . ?
C1A N2B N1A 100.0(11) . . ?
C1A N2B N1B 119.3(12) . . ?
C1A N2B C3 122.8(9) . . ?
C1B N2B N1A 144.9(15) . . ?
C1B N2B N2A 85.8(12) . . ?
C1B N2B C1A 47.1(9) . . ?
C1B N2B N1B 159.7(15) . . ?
C1B N2B C3 75.8(11) . . ?
N1B N2B N1A 19.9(11) . . ?
N1B N2B C3 116.2(8) . . ?
C3 N2B N1A 136.1(9) . . ?
O2A C1A C2 141.2(10) . . ?
N2A C1A O2A 148.3(17) . . ?
N2A C1A N2B 49.7(10) . . ?
N2A C1A C1B 92.5(17) . . ?
N2A C1A O2B 169.8(17) . . ?
N2A C1A C2 70.4(13) . . ?
N2B C1A O2A 98.6(10) . . ?
N2B C1A C2 120.1(10) . . ?
C1B C1A O2A 55.8(10) . . ?
C1B C1A N2B 42.9(9) . . ?
C1B C1A O2B 79.0(12) . . ?
C1B C1A C2 162.7(15) . . ?
O2B C1A O2A 23.6(6) . . ?
O2B C1A N2B 121.3(12) . . ?
O2B C1A C2 118.3(10) . . ?
O2A C1B N2A 120.6(12) . . ?
O2A C1B O2B 23.0(6) . . ?
N2A C1B O2B 97.9(10) . . ?
N2B C1B O2A 170.0(16) . . ?
N2B C1B N2A 50.6(8) . . ?
N2B C1B C1A 90.0(15) . . ?
N2B C1B O2B 147.3(14) . . ?
C1A C1B O2A 81.1(13) . . ?
C1A C1B N2A 39.5(9) . . ?
C1A C1B O2B 58.5(11) . . ?
O2A O2B C1A 96(2) . . ?
O2A O2B C1B 54.3(18) . . ?
C1A O2B C1B 42.5(7) . . ?
N1A N1B N2A 62(5) . . ?
N1A N1B N2B 101(5) . . ?
N1A N1B C1 72(5) . . ?
N2B N1B N2A 39.8(8) . . ?
N2B N1B C1 120.4(17) . . ?
C1 N1B N2A 107.6(12) . . ?
N1A C1 C5 113.8(11) . . ?
N1A C1 N1B 23.0(10) . . ?
N1B C1 C5 114.3(10) . . ?
O0AA C1 N1A 122.5(11) . . ?
O0AA C1 C5 122.1(4) . . ?
O0AA C1 N1B 122.6(10) . . ?
C11 F2B F1 48.0(5) . . ?
C11 F2B F3B 55.0(8) . . ?
F2 F2B C11 73.5(12) . . ?
F2 F2B F1 114.1(15) . . ?
F2 F2B F3B 22.0(11) . . ?
F2A F2B C11 69.9(12) . . ?
F2A F2B F1 25.4(10) . . ?
F2A F2B F2 139(2) . . ?
F2A F2B F3B 117.6(17) . . ?
F3B F2B F1 92.2(10) . . ?
C11 F3B F3 60.6(8) . . ?
C11 F3B F2B 55.5(7) . . ?
F3 F3B F2B 113.2(11) . . ?
F2 F3B C11 74.9(13) . . ?
F2 F3B F3 135.0(17) . . ?
F2 F3B F3A 134(2) . . ?
F2 F3B F2B 23.0(11) . . ?
F3A F3B C11 62.0(12) . . ?
F3A F3B F3 8.6(10) . . ?
F3A F3B F2B 111.2(16) . . ?
C11 F1B F1 54.7(7) . . ?
F3 F1B C11 78.9(13) . . ?
F3 F1B F1 131.9(16) . . ?
F3 F1B F3A 32.8(10) . . ?
F3 F1B F1A 153.5(19) . . ?
F3A F1B C11 57.4(8) . . ?
F3A F1B F1 102.3(13) . . ?
F1A F1B C11 75.9(12) . . ?
F1A F1B F1 28.6(8) . . ?
F1A F1B F3A 129.9(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CNPh-NH_NMe-Me
_database_code_depnum_ccdc_archive 'CCDC 1959999'
loop_
_audit_author_name
_audit_author_address
'JUGAL KISHORE RAI DEKA'
;Shiv Nadar University
India
;
_audit_update_record             
;
2019-10-17 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_audit_creation_date             2019-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_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                   9.8467(5)
_cell_length_b                   11.5760(5)
_cell_length_c                   9.6970(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.927(2)
_cell_angle_gamma                90
_cell_volume                     1105.17(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3220
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      23.69
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   0.996
_exptl_transmission_factor_min   0.980
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13906
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      296.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   X-ray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1441
_reflns_number_total             1946
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         1946
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.089
_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)+(0.0538P)²+0.2383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N3A) \\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(N3A) = Uanis(N3)
3. Others
 Sof(C10A)=1-FVAR(1)
 Sof(C10)=FVAR(1)
 Sof(N3A)=1-FVAR(2)
 Sof(N3)=FVAR(2)
 Sof(O2A)=1-FVAR(3)
 Sof(O2)=FVAR(3)
 Sof(N2A)=1-FVAR(4)
 Sof(N2)=FVAR(4)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2A), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25849(18) 0.74808(13) 0.20207(13) 0.0735(5) Uani 1 1 d . . . . .
N2 N 0.3234(16) 0.7889(7) 0.4197(5) 0.054(2) Uani 0.85(4) 1 d . U P A 1
O2 O 0.4864(12) 1.0320(14) 0.281(3) 0.076(4) Uani 0.56(10) 1 d . . P A 1
C4 C 0.22788(19) 0.60162(15) 0.37058(17) 0.0482(5) Uani 1 1 d . . . . .
C1 C 0.1361(2) 0.38735(15) 0.4533(2) 0.0520(5) Uani 1 1 d . . . . .
N3 N 0.3509(3) 0.9038(2) 0.3878(2) 0.0588(7) Uani 0.821(5) 1 d . . P A 1
C5 C 0.2893(2) 0.54603(16) 0.4819(2) 0.0536(5) Uani 1 1 d . . . . .
H5 H 0.361360 0.581034 0.528862 0.064 Uiso 1 1 calc R . . . .
C3 C 0.1219(2) 0.54802(17) 0.29974(19) 0.0536(5) Uani 1 1 d . . . . .
H3 H 0.081854 0.584284 0.223800 0.064 Uiso 1 1 calc R . . . .
C2 C 0.0758(2) 0.44156(16) 0.3410(2) 0.0555(5) Uani 1 1 d . . . . .
H2A H 0.004194 0.406187 0.293610 0.067 Uiso 1 1 calc R . . . .
C6 C 0.2438(2) 0.43908(16) 0.5231(2) 0.0561(5) Uani 1 1 d . . . . .
H6 H 0.285268 0.401760 0.597523 0.067 Uiso 1 1 calc R . . . .
C8 C 0.2719(2) 0.71747(17) 0.32180(19) 0.0566(5) Uani 1 1 d . . . . .
N1 N 0.0432(2) 0.19016(17) 0.5322(3) 0.0855(7) Uani 1 1 d . . . . .
C7 C 0.0851(2) 0.27703(18) 0.4976(2) 0.0620(6) Uani 1 1 d . . . . .
C9 C 0.2456(3) 0.9872(2) 0.4119(3) 0.0751(7) Uani 1 1 d . . . . .
C10 C 0.4693(4) 0.9310(6) 0.3274(4) 0.059(2) Uani 0.779(19) 1 d . . P A 1
C11 C 0.5716(3) 0.8377(3) 0.3083(4) 0.0856(8) Uani 1 1 d . . . . .
C10A C 0.4506(11) 0.8609(18) 0.3667(13) 0.046(5) Uani 0.221(19) 1 d . . P A 2
N3A N 0.3954(15) 0.9666(13) 0.3566(11) 0.0588(7) Uani 0.179(5) 1 d . U P A 2
H2 H 0.321(2) 0.770(2) 0.505(3) 0.074(7) Uiso 1 1 d . . . . .
H11A H 0.538(3) 0.770(3) 0.251(4) 0.127(11) Uiso 1 1 d . . . . .
H11B H 0.649(4) 0.878(3) 0.283(4) 0.140(13) Uiso 1 1 d . . . . .
H9A H 0.283(4) 1.065(3) 0.397(4) 0.152(14) Uiso 1 1 d . . . . .
H11C H 0.594(3) 0.799(3) 0.395(4) 0.124(12) Uiso 1 1 d . . . . .
H9B H 0.220(4) 0.980(3) 0.512(5) 0.157(14) Uiso 1 1 d . . . . .
H9C H 0.164(4) 0.957(3) 0.370(4) 0.170(16) Uiso 1 1 d . . . . .
O2A O 0.474(3) 1.0393(19) 0.316(5) 0.102(6) Uani 0.44(10) 1 d . . P A 2
N2A N 0.384(7) 0.763(3) 0.4088(19) 0.050(8) Uani 0.15(4) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.219(2) . ?
N2 N3 1.392(5) . ?
N2 C8 1.351(4) . ?
O2 C10 1.264(17) . ?
C4 C5 1.387(3) . ?
C4 C3 1.386(3) . ?
C4 C8 1.489(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.385(3) . ?
C1 C7 1.440(3) . ?
N3 C9 1.439(4) . ?
N3 C10 1.350(6) . ?
C5 C6 1.378(3) . ?
C3 C2 1.375(3) . ?
C8 N2A 1.48(4) . ?
N1 C7 1.140(3) . ?
C9 N3A 1.595(16) . ?
C10 C11 1.491(6) . ?
C11 C10A 1.354(11) . ?
C10A N3A 1.34(2) . ?
C10A N2A 1.37(3) . ?
N3A O2A 1.22(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
C8 N2 N3 120.1(3) . . ?
C5 C4 C8 122.66(18) . . ?
C3 C4 C5 119.54(18) . . ?
C3 C4 C8 117.79(17) . . ?
C2 C1 C6 120.31(17) . . ?
C2 C1 C7 119.31(19) . . ?
C6 C1 C7 120.37(18) . . ?
N2 N3 C9 117.5(8) . . ?
C10 N3 N2 119.4(8) . . ?
C10 N3 C9 122.9(4) . . ?
C6 C5 C4 120.18(19) . . ?
C2 C3 C4 120.43(18) . . ?
C3 C2 C1 119.72(19) . . ?
C5 C6 C1 119.78(18) . . ?
O1 C8 N2 121.6(2) . . ?
O1 C8 C4 122.46(18) . . ?
O1 C8 N2A 120.4(8) . . ?
N2 C8 C4 115.9(2) . . ?
N2A C8 C4 111.2(11) . . ?
N1 C7 C1 179.2(3) . . ?
O2 C10 N3 119.4(10) . . ?
O2 C10 C11 122.1(10) . . ?
N3 C10 C11 118.3(6) . . ?
C11 C10A N2A 113(3) . . ?
N3A C10A C11 120.5(18) . . ?
N3A C10A N2A 125(4) . . ?
C10A N3A C9 119.2(13) . . ?
O2A N3A C9 127(2) . . ?
O2A N3A C10A 113(2) . . ?
C10A N2A C8 119(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
