# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1906539'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 N2 O5 V'
_chemical_formula_weight         360.28

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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.6403(3)
_cell_length_b                   11.0311(3)
_cell_length_c                   13.4694(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.8870(10)
_cell_angle_gamma                90
_cell_volume                     1578.95(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      33.077

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.655
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_process_details   SADABS
_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  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30489
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         33.077
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5993
_reflns_number_gt                4439
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
;
 SHELXL-2014/7 (Sheldrick, 2015) and WinGX (Farrugia, 2012)
;
_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)+(0.0569P)²+0.2849P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.044(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5282
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_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
V1 V 0.37284(2) 0.29655(2) 0.53339(2) 0.02501(8) Uani 1 1 d . . . . .
O3 O 0.49970(8) 0.35527(10) 0.58598(7) 0.0369(2) Uani 1 1 d . . . . .
O1 O 0.25145(8) 0.38268(9) 0.60649(6) 0.03164(19) Uani 1 1 d . . . . .
O4 O 0.12847(9) 0.43648(11) 0.76721(7) 0.0423(2) Uani 1 1 d . . . . .
O2 O 0.35902(11) 0.15801(10) 0.56906(7) 0.0428(2) Uani 1 1 d . . . . .
N1 N 0.24097(10) 0.32831(10) 0.41168(7) 0.0304(2) Uani 1 1 d . . . . .
N2 N 0.48016(9) 0.25535(9) 0.40139(7) 0.02504(19) Uani 1 1 d . . . . .
O5 O 0.72966(11) 0.22875(13) 0.32525(10) 0.0572(3) Uani 1 1 d . . . . .
C3 C 0.12766(11) 0.37504(11) 0.59976(9) 0.0282(2) Uani 1 1 d . . . . .
C2 C 0.05883(12) 0.34538(12) 0.51118(10) 0.0321(3) Uani 1 1 d . . . . .
C1 C 0.12132(12) 0.33173(12) 0.42018(9) 0.0327(3) Uani 1 1 d . . . . .
H1 H 0.070819 0.324711 0.362069 0.039 Uiso 1 1 calc R U . . .
C10 C 0.28737(14) 0.31849(15) 0.31161(9) 0.0391(3) Uani 1 1 d . . . . .
H10B H 0.319932 0.395898 0.290387 0.047 Uiso 1 1 calc R U . . .
H10A H 0.220059 0.293718 0.264720 0.047 Uiso 1 1 calc R U . . .
C11 C 0.39011(13) 0.22495(13) 0.31678(9) 0.0328(3) Uani 1 1 d . . . . .
H11A H 0.354504 0.145135 0.326520 0.039 Uiso 1 1 calc R U . . .
H11B H 0.433440 0.224302 0.255127 0.039 Uiso 1 1 calc R U . . .
C12 C 0.56248(14) 0.35960(13) 0.37700(10) 0.0367(3) Uani 1 1 d . . . . .
H12B H 0.610209 0.384723 0.436738 0.044 Uiso 1 1 calc R U . . .
H12A H 0.510072 0.427236 0.354711 0.044 Uiso 1 1 calc R U . . .
C13 C 0.65326(17) 0.32919(17) 0.29700(12) 0.0518(4) Uani 1 1 d . . . . .
H13A H 0.606035 0.310838 0.235355 0.062 Uiso 1 1 calc R U . . .
H13B H 0.706222 0.398869 0.285569 0.062 Uiso 1 1 calc R U . . .
C14 C 0.65389(15) 0.12606(16) 0.34221(12) 0.0466(4) Uani 1 1 d . . . . .
H14B H 0.707395 0.057619 0.360542 0.056 Uiso 1 1 calc R U . . .
H14A H 0.605864 0.105376 0.281446 0.056 Uiso 1 1 calc R U . . .
C15 C 0.56449(13) 0.15003(13) 0.42416(10) 0.0362(3) Uani 1 1 d . . . . .
H15A H 0.513609 0.078377 0.433588 0.043 Uiso 1 1 calc R U . . .
H15B H 0.612930 0.165449 0.485804 0.043 Uiso 1 1 calc R U . . .
C9 C -0.07344(13) 0.33908(15) 0.50809(12) 0.0419(3) Uani 1 1 d . . . . .
H9 H -0.117375 0.320709 0.448552 0.050 Uiso 1 1 calc R U . . .
C8 C -0.13765(13) 0.35957(16) 0.59120(13) 0.0472(4) Uani 1 1 d . . . . .
H8 H -0.224785 0.352000 0.589341 0.057 Uiso 1 1 calc R U . . .
C7 C -0.07142(13) 0.39214(15) 0.67956(12) 0.0423(3) Uani 1 1 d . . . . .
H7 H -0.115465 0.407416 0.736141 0.051 Uiso 1 1 calc R U . . .
C4 C 0.05815(12) 0.40204(12) 0.68432(10) 0.0330(3) Uani 1 1 d . . . . .
C5 C 0.06358(16) 0.48882(18) 0.84644(12) 0.0523(4) Uani 1 1 d . . . . .
H5A H 0.006182 0.430153 0.872906 0.063 Uiso 1 1 calc R U . . .
H5B H 0.015177 0.558433 0.822653 0.063 Uiso 1 1 calc R U . . .
C6 C 0.15859(19) 0.5267(2) 0.92517(12) 0.0590(5) Uani 1 1 d . . . . .
H6B H 0.199969 0.456322 0.953064 0.088 Uiso 1 1 calc R U . . .
H6C H 0.117502 0.569574 0.976432 0.088 Uiso 1 1 calc R U . . .
H6A H 0.219602 0.578759 0.896823 0.088 Uiso 1 1 calc R U . . .


_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
V1 O2 1.6109(11) . ?
V1 O3 1.6269(9) . ?
V1 O1 1.9154(8) . ?
V1 N1 2.1325(11) . ?
V1 N2 2.2082(9) . ?
O1 C3 1.3185(14) . ?
O4 C4 1.3662(17) . ?
O4 C5 1.4223(16) . ?
N1 C1 1.2846(17) . ?
N1 C10 1.4627(16) . ?
N2 C11 1.4896(16) . ?
N2 C15 1.4904(16) . ?
N2 C12 1.4922(16) . ?
O5 C13 1.415(3) . ?
O5 C14 1.416(2) . ?
C3 C2 1.4068(18) . ?
C3 C4 1.4205(16) . ?
C2 C9 1.4076(18) . ?
C2 C1 1.4315(18) . ?
C1 H1 0.9300 . ?
C10 C11 1.502(2) . ?
C10 H10B 0.9700 . ?
C10 H10A 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.520(2) . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.5162(18) . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C9 C8 1.359(2) . ?
C9 H9 0.9300 . ?
C8 C7 1.399(2) . ?
C8 H8 0.9300 . ?
C7 C4 1.3812(18) . ?
C7 H7 0.9300 . ?
C5 C6 1.488(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C6 H6A 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
O2 V1 O3 109.52(6) . . ?
O2 V1 O1 104.08(5) . . ?
O3 V1 O1 98.33(4) . . ?
O2 V1 N1 108.59(5) . . ?
O3 V1 N1 140.23(5) . . ?
O1 V1 N1 83.05(4) . . ?
O2 V1 N2 95.94(5) . . ?
O3 V1 N2 88.92(4) . . ?
O1 V1 N2 154.88(4) . . ?
N1 V1 N2 76.22(4) . . ?
C3 O1 V1 129.06(8) . . ?
C4 O4 C5 117.35(11) . . ?
C1 N1 C10 117.80(11) . . ?
C1 N1 V1 123.58(9) . . ?
C10 N1 V1 117.18(8) . . ?
C11 N2 C15 109.84(10) . . ?
C11 N2 C12 111.54(10) . . ?
C15 N2 C12 106.98(11) . . ?
C11 N2 V1 108.88(7) . . ?
C15 N2 V1 108.97(7) . . ?
C12 N2 V1 110.59(7) . . ?
C13 O5 C14 110.23(12) . . ?
O1 C3 C2 123.29(11) . . ?
O1 C3 C4 119.35(11) . . ?
C2 C3 C4 117.32(11) . . ?
C3 C2 C9 120.90(12) . . ?
C3 C2 C1 120.41(11) . . ?
C9 C2 C1 118.45(12) . . ?
N1 C1 C2 125.77(11) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
N1 C10 C11 106.66(10) . . ?
N1 C10 H10B 110.4 . . ?
C11 C10 H10B 110.4 . . ?
N1 C10 H10A 110.4 . . ?
C11 C10 H10A 110.4 . . ?
H10B C10 H10A 108.6 . . ?
N2 C11 C10 108.63(10) . . ?
N2 C11 H11A 110.0 . . ?
C10 C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
N2 C12 C13 112.76(11) . . ?
N2 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
N2 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
H12B C12 H12A 107.8 . . ?
O5 C13 C12 111.05(13) . . ?
O5 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
O5 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O5 C14 C15 111.17(12) . . ?
O5 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
O5 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
H14B C14 H14A 108.0 . . ?
N2 C15 C14 112.30(11) . . ?
N2 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
N2 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C8 C9 C2 120.71(14) . . ?
C8 C9 H9 119.6 . . ?
C2 C9 H9 119.6 . . ?
C9 C8 C7 119.39(13) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C4 C7 C8 121.24(13) . . ?
C4 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
O4 C4 C7 124.35(12) . . ?
O4 C4 C3 115.33(11) . . ?
C7 C4 C3 120.33(13) . . ?
O4 C5 C6 108.11(13) . . ?
O4 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
O4 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
V1 O1 C3 C2 -30.11(18) . . . . ?
V1 O1 C3 C4 152.28(10) . . . . ?
O1 C3 C2 C9 -179.68(13) . . . . ?
C4 C3 C2 C9 -2.02(19) . . . . ?
O1 C3 C2 C1 -5.4(2) . . . . ?
C4 C3 C2 C1 172.30(12) . . . . ?
C10 N1 C1 C2 -177.69(13) . . . . ?
V1 N1 C1 C2 16.5(2) . . . . ?
C3 C2 C1 N1 9.8(2) . . . . ?
C9 C2 C1 N1 -175.76(14) . . . . ?
C1 N1 C10 C11 -135.50(13) . . . . ?
V1 N1 C10 C11 31.25(15) . . . . ?
C15 N2 C11 C10 166.22(11) . . . . ?
C12 N2 C11 C10 -75.35(13) . . . . ?
V1 N2 C11 C10 46.97(12) . . . . ?
N1 C10 C11 N2 -50.35(15) . . . . ?
C11 N2 C12 C13 -67.60(16) . . . . ?
C15 N2 C12 C13 52.53(16) . . . . ?
V1 N2 C12 C13 171.07(11) . . . . ?
C14 O5 C13 C12 59.13(17) . . . . ?
N2 C12 C13 O5 -57.23(17) . . . . ?
C13 O5 C14 C15 -59.91(17) . . . . ?
C11 N2 C15 C14 68.29(15) . . . . ?
C12 N2 C15 C14 -52.93(15) . . . . ?
V1 N2 C15 C14 -172.52(10) . . . . ?
O5 C14 C15 N2 58.39(17) . . . . ?
C3 C2 C9 C8 -1.1(2) . . . . ?
C1 C2 C9 C8 -175.54(14) . . . . ?
C2 C9 C8 C7 2.7(2) . . . . ?
C9 C8 C7 C4 -1.0(2) . . . . ?
C5 O4 C4 C7 -13.4(2) . . . . ?
C5 O4 C4 C3 166.97(14) . . . . ?
C8 C7 C4 O4 178.19(14) . . . . ?
C8 C7 C4 C3 -2.2(2) . . . . ?
O1 C3 C4 O4 1.03(18) . . . . ?
C2 C3 C4 O4 -176.73(12) . . . . ?
O1 C3 C4 C7 -178.62(13) . . . . ?
C2 C3 C4 C7 3.63(19) . . . . ?
C4 O4 C5 C6 -176.20(14) . . . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.050

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1906540'
loop_
_audit_author_name
_audit_author_address
'Shouvik Chattopadhyay'
;Jadavpur University, kolkata
India
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2019-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 Br N2 O3 V'
_chemical_formula_weight         353.08

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'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.7006(3)
_cell_length_b                   11.7699(6)
_cell_length_c                   16.5401(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.969(3)
_cell_angle_gamma                90
_cell_volume                     1288.49(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    900
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      33.153

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    3.872
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.326
_exptl_absorpt_correction_T_max  0.461
_exptl_absorpt_process_details   SADABS
_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  'BRUKER SMART APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24886
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         33.153
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4915
_reflns_number_gt                2687
_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       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
;
 SHELXL-2014/7 (Sheldrick, 2015) and WinGX (Farrugia, 2012)
;
_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)+(0.0609P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0092(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4490
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.75287(5) 0.22527(3) 0.61189(2) 0.05544(14) Uani 1 1 d . . . . .
V1 V 0.15558(6) 0.76009(3) 0.62484(2) 0.02779(13) Uani 1 1 d . . . . .
O3 O -0.0332(3) 0.81132(16) 0.56179(11) 0.0396(4) Uani 1 1 d . . . . .
O1 O 0.1663(2) 0.61338(14) 0.57790(11) 0.0420(5) Uani 1 1 d . . . . .
O2 O 0.0844(3) 0.73649(17) 0.71211(13) 0.0480(5) Uani 1 1 d . . . . .
N1 N 0.4804(3) 0.74943(16) 0.63914(13) 0.0319(5) Uani 1 1 d . . . . .
N2 N 0.2591(3) 0.93227(16) 0.65153(12) 0.0309(4) Uani 1 1 d . . . . .
C8 C 0.5687(4) 0.3497(2) 0.60061(15) 0.0347(6) Uani 1 1 d . . . . .
C9 C 0.3648(4) 0.3301(2) 0.57439(16) 0.0395(6) Uani 1 1 d . . . . .
H9 H 0.318431 0.256767 0.561897 0.047 Uiso 1 1 calc R U . . .
C10 C 0.2319(4) 0.4193(2) 0.56697(16) 0.0376(6) Uani 1 1 d . . . . .
H10 H 0.095490 0.405948 0.548846 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2983(4) 0.5302(2) 0.58626(14) 0.0302(5) Uani 1 1 d . . . . .
C6 C 0.5054(3) 0.54882(19) 0.61173(14) 0.0283(5) Uani 1 1 d . . . . .
C5 C 0.5857(3) 0.6593(2) 0.63401(15) 0.0330(5) Uani 1 1 d . . . . .
H5 H 0.725527 0.666272 0.645713 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5961(4) 0.8527(2) 0.6666(2) 0.0450(7) Uani 1 1 d . . . . .
H4A H 0.639739 0.891137 0.620514 0.054 Uiso 1 1 calc R U . . .
H4B H 0.714356 0.833583 0.705935 0.054 Uiso 1 1 calc R U . . .
C3 C 0.4541(4) 0.9277(2) 0.70574(17) 0.0400(6) Uani 1 1 d . . . . .
H3A H 0.436208 0.896956 0.758560 0.048 Uiso 1 1 calc R U . . .
H3B H 0.510130 1.003531 0.714063 0.048 Uiso 1 1 calc R U . . .
C1 C 0.1121(5) 0.9957(3) 0.6929(2) 0.0630(10) Uani 1 1 d . . . . .
H1A H -0.015885 0.998861 0.657542 0.094 Uiso 1 1 calc R U . . .
H1B H 0.096108 0.957685 0.742822 0.094 Uiso 1 1 calc R U . . .
H1C H 0.160908 1.071412 0.704943 0.094 Uiso 1 1 calc R U . . .
C2 C 0.2814(5) 0.9924(3) 0.5746(2) 0.0601(9) Uani 1 1 d . . . . .
H2A H 0.153121 0.995036 0.539486 0.090 Uiso 1 1 calc R U . . .
H2B H 0.328429 1.068428 0.587090 0.090 Uiso 1 1 calc R U . . .
H2C H 0.377190 0.952757 0.547421 0.090 Uiso 1 1 calc R U . . .
C7 C 0.6408(4) 0.4566(2) 0.61781(14) 0.0321(5) Uani 1 1 d . . . . .
H7 H 0.778578 0.468644 0.633465 0.038 Uiso 1 1 calc R U . . .


_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
Br1 C8 1.905(2) . ?
V1 O2 1.613(2) . ?
V1 O3 1.6247(16) . ?
V1 O1 1.8992(17) . ?
V1 N1 2.156(2) . ?
V1 N2 2.165(2) . ?
O1 C11 1.312(3) . ?
N1 C5 1.284(3) . ?
N1 C4 1.475(3) . ?
N2 C3 1.466(3) . ?
N2 C2 1.484(4) . ?
N2 C1 1.485(3) . ?
C8 C7 1.362(3) . ?
C8 C9 1.387(4) . ?
C9 C10 1.369(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.400(3) . ?
C10 H10 0.9300 . ?
C11 C6 1.403(3) . ?
C6 C7 1.408(3) . ?
C6 C5 1.433(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.515(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 V1 O3 109.22(10) . . ?
O2 V1 O1 104.15(10) . . ?
O3 V1 O1 98.64(8) . . ?
O2 V1 N1 109.02(9) . . ?
O3 V1 N1 139.78(9) . . ?
O1 V1 N1 83.69(7) . . ?
O2 V1 N2 96.24(9) . . ?
O3 V1 N2 88.63(8) . . ?
O1 V1 N2 154.57(8) . . ?
N1 V1 N2 75.30(7) . . ?
C11 O1 V1 134.67(15) . . ?
C5 N1 C4 115.7(2) . . ?
C5 N1 V1 126.63(16) . . ?
C4 N1 V1 117.33(15) . . ?
C3 N2 C2 110.0(2) . . ?
C3 N2 C1 109.2(2) . . ?
C2 N2 C1 108.5(3) . . ?
C3 N2 V1 108.48(15) . . ?
C2 N2 V1 110.10(17) . . ?
C1 N2 V1 110.47(17) . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 Br1 119.12(19) . . ?
C9 C8 Br1 119.65(19) . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
O1 C11 C10 119.1(2) . . ?
O1 C11 C6 122.3(2) . . ?
C10 C11 C6 118.5(2) . . ?
C11 C6 C7 119.8(2) . . ?
C11 C6 C5 122.2(2) . . ?
C7 C6 C5 118.0(2) . . ?
N1 C5 C6 125.3(2) . . ?
N1 C5 H5 117.3 . . ?
C6 C5 H5 117.3 . . ?
N1 C4 C3 106.1(2) . . ?
N1 C4 H4A 110.5 . . ?
C3 C4 H4A 110.5 . . ?
N1 C4 H4B 110.5 . . ?
C3 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N2 C3 C4 108.6(2) . . ?
N2 C3 H3A 110.0 . . ?
C4 C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 V1 O1 C11 -81.2(3) . . . . ?
O3 V1 O1 C11 166.4(2) . . . . ?
N1 V1 O1 C11 26.9(2) . . . . ?
N2 V1 O1 C11 61.1(3) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
Br1 C8 C9 C10 179.4(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
V1 O1 C11 C10 156.1(2) . . . . ?
V1 O1 C11 C6 -25.7(4) . . . . ?
C9 C10 C11 O1 179.6(2) . . . . ?
C9 C10 C11 C6 1.4(4) . . . . ?
O1 C11 C6 C7 -178.5(2) . . . . ?
C10 C11 C6 C7 -0.4(4) . . . . ?
O1 C11 C6 C5 3.0(4) . . . . ?
C10 C11 C6 C5 -178.9(2) . . . . ?
C4 N1 C5 C6 177.5(2) . . . . ?
V1 N1 C5 C6 4.8(4) . . . . ?
C11 C6 C5 N1 5.4(4) . . . . ?
C7 C6 C5 N1 -173.1(2) . . . . ?
C5 N1 C4 C3 -153.9(2) . . . . ?
V1 N1 C4 C3 19.5(3) . . . . ?
C2 N2 C3 C4 -66.7(3) . . . . ?
C1 N2 C3 C4 174.2(2) . . . . ?
V1 N2 C3 C4 53.8(2) . . . . ?
N1 C4 C3 N2 -46.9(3) . . . . ?
C9 C8 C7 C6 2.3(4) . . . . ?
Br1 C8 C7 C6 -178.35(18) . . . . ?
C11 C6 C7 C8 -1.5(4) . . . . ?
C5 C6 C7 C8 177.1(2) . . . . ?

_refine_diff_density_max         0.700
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.102

