# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1059035'
_audit_update_record             
;
2015-04-12 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
_audit_creation_date             2015-04-06
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
'dimethyl 4-((2-bromophenyl)amino)quinoline-2,3-dicarboxylate'
_chemical_formula_moiety         'C19 H16 Br N2 O4'
_chemical_formula_sum            'C19 H16 Br N2 O4'
_chemical_formula_weight         416.25
_chemical_melting_point          148-150
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4200(12)
_cell_length_b                   10.1497(7)
_cell_length_c                   11.2030(17)
_cell_angle_alpha                66.531(11)
_cell_angle_beta                 88.054(12)
_cell_angle_gamma                88.057(10)
_cell_volume                     877.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    2.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6815
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.974
_diffrn_reflns_theta_min         3.095
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2835
_reflns_number_total             3972
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    ?
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3972
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.0402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.51593(4) 0.15467(4) 0.23392(4) 0.06303(16) Uani 1 1 d . . . . .
O4 O 0.2715(3) 0.1072(2) 0.8661(2) 0.0507(5) Uani 1 1 d . . . . .
O2 O 0.0541(3) 0.0510(2) 0.7038(2) 0.0526(6) Uani 1 1 d . . . . .
O1 O 0.2213(3) 0.0371(2) 0.5498(2) 0.0623(7) Uani 1 1 d . . . . .
O3 O 0.0451(3) 0.2137(2) 0.8973(2) 0.0617(7) Uani 1 1 d . . . . .
N2 N 0.1880(3) 0.4382(3) 0.6707(2) 0.0498(7) Uani 1 1 d . . . . .
H13 H 0.1560 0.4672 0.7264 0.060 Uiso 1 1 d R U . . .
N1 N 0.2995(3) 0.2988(3) 0.3709(2) 0.0481(6) Uani 1 1 d . . . . .
H14 H 0.3193 0.1999 0.4034 0.058 Uiso 1 1 d R U . . .
C19 C 0.0101(5) -0.0972(4) 0.7368(4) 0.0662(10) Uani 1 1 d . . . . .
H1A H -0.0463 -0.1030 0.6661 0.099 Uiso 1 1 calc R U . . .
H1B H -0.0568 -0.1292 0.8138 0.099 Uiso 1 1 calc R U . . .
H1C H 0.1043 -0.1572 0.7524 0.099 Uiso 1 1 calc R U . . .
C18 C 0.1655(4) 0.1045(3) 0.6098(3) 0.0421(7) Uani 1 1 d . . . . .
C2 C 0.3738(3) 0.3127(3) 0.1557(3) 0.0401(7) Uani 1 1 d . . . . .
C15 C 0.1512(4) 0.2033(3) 0.8285(3) 0.0440(7) Uani 1 1 d . . . . .
C12 C 0.2555(5) 0.6796(4) 0.5360(4) 0.0614(10) Uani 1 1 d . . . . .
H18 H 0.2161 0.7083 0.6006 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1791(3) 0.3046(3) 0.6877(3) 0.0400(7) Uani 1 1 d . . . . .
C1 C 0.2856(4) 0.3672(3) 0.2351(3) 0.0400(7) Uani 1 1 d . . . . .
C7 C 0.2634(3) 0.3486(3) 0.4659(3) 0.0398(7) Uani 1 1 d . . . . .
C8 C 0.2897(3) 0.4941(3) 0.4488(3) 0.0396(7) Uani 1 1 d . . . . .
C11 C 0.3278(5) 0.7772(4) 0.4274(4) 0.0623(10) Uani 1 1 d . . . . .
H27 H 0.3369 0.8718 0.4182 0.075 Uiso 1 1 calc R U . . .
C17 C 0.2041(3) 0.2530(3) 0.5871(3) 0.0386(6) Uani 1 1 d . . . . .
C6 C 0.1813(4) 0.4817(3) 0.1737(3) 0.0478(7) Uani 1 1 d . . . . .
H30 H 0.1182 0.5179 0.2239 0.057 Uiso 1 1 calc R U . . .
C16 C 0.2630(5) 0.0008(4) 0.9988(3) 0.0635(10) Uani 1 1 d . . . . .
H33A H 0.1673 -0.0524 1.0118 0.095 Uiso 1 1 calc R U . . .
H33B H 0.2628 0.0481 1.0580 0.095 Uiso 1 1 calc R U . . .
H33C H 0.3534 -0.0637 1.0146 0.095 Uiso 1 1 calc R U . . .
C3 C 0.3586(4) 0.3710(4) 0.0216(3) 0.0519(8) Uani 1 1 d . . . . .
H34 H 0.4158 0.3313 -0.0289 0.062 Uiso 1 1 calc R U . . .
C4 C 0.2585(5) 0.4876(4) -0.0363(3) 0.0608(10) Uani 1 1 d . . . . .
H34C H 0.2505 0.5297 -0.1263 0.073 Uiso 1 1 calc R U . . .
C9 C 0.3701(4) 0.5969(3) 0.3398(3) 0.0484(8) Uani 1 1 d . . . . .
H35 H 0.4113 0.5707 0.2740 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1691(4) 0.5423(4) 0.0414(3) 0.0547(8) Uani 1 1 d . . . . .
H40 H 0.1007 0.6208 0.0028 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2398(4) 0.5353(3) 0.5515(3) 0.0460(7) Uani 1 1 d . . . . .
C10 C 0.3878(4) 0.7352(3) 0.3306(3) 0.0548(8) Uani 1 1 d . . . . .
H44 H 0.4407 0.8013 0.2585 0.066 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 C2 1.896(3) . ?
O4 C15 1.337(4) . ?
O4 C16 1.450(4) . ?
O2 C19 1.457(4) . ?
O2 C18 1.340(4) . ?
O1 C18 1.210(3) . ?
O3 C15 1.189(3) . ?
N2 H13 0.8230 . ?
N2 C14 1.297(4) . ?
N2 C13 1.373(4) . ?
N1 H14 0.9322 . ?
N1 C1 1.405(4) . ?
N1 C7 1.371(4) . ?
C19 H1A 0.9600 . ?
C19 H1B 0.9600 . ?
C19 H1C 0.9600 . ?
C18 C17 1.471(4) . ?
C2 C1 1.403(4) . ?
C2 C3 1.387(4) . ?
C15 C14 1.516(4) . ?
C12 H18 0.9300 . ?
C12 C11 1.364(5) . ?
C12 C13 1.415(4) . ?
C14 C17 1.427(4) . ?
C1 C6 1.389(4) . ?
C7 C8 1.436(4) . ?
C7 C17 1.404(4) . ?
C8 C9 1.419(4) . ?
C8 C13 1.420(4) . ?
C11 H27 0.9300 . ?
C11 C10 1.390(5) . ?
C6 H30 0.9300 . ?
C6 C5 1.366(4) . ?
C16 H33A 0.9600 . ?
C16 H33B 0.9600 . ?
C16 H33C 0.9600 . ?
C3 H34 0.9300 . ?
C3 C4 1.375(5) . ?
C4 H34C 0.9300 . ?
C4 C5 1.394(5) . ?
C9 H35 0.9300 . ?
C9 C10 1.379(4) . ?
C5 H40 0.9300 . ?
C10 H44 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
C15 O4 C16 116.4(3) . . ?
C18 O2 C19 116.6(2) . . ?
C14 N2 H13 122.0 . . ?
C14 N2 C13 118.3(2) . . ?
C13 N2 H13 119.4 . . ?
C1 N1 H14 115.5 . . ?
C7 N1 H14 113.4 . . ?
C7 N1 C1 130.2(3) . . ?
O2 C19 H1A 109.5 . . ?
O2 C19 H1B 109.5 . . ?
O2 C19 H1C 109.5 . . ?
H1A C19 H1B 109.5 . . ?
H1A C19 H1C 109.5 . . ?
H1B C19 H1C 109.5 . . ?
O2 C18 C17 112.0(2) . . ?
O1 C18 O2 122.4(3) . . ?
O1 C18 C17 125.6(3) . . ?
C1 C2 Br1 119.1(2) . . ?
C3 C2 Br1 119.3(2) . . ?
C3 C2 C1 121.6(3) . . ?
O4 C15 C14 109.2(3) . . ?
O3 C15 O4 125.3(3) . . ?
O3 C15 C14 125.4(3) . . ?
C11 C12 H18 119.6 . . ?
C11 C12 C13 120.9(3) . . ?
C13 C12 H18 119.6 . . ?
N2 C14 C15 113.7(2) . . ?
N2 C14 C17 124.4(3) . . ?
C17 C14 C15 121.8(3) . . ?
C2 C1 N1 119.0(3) . . ?
C6 C1 N1 123.8(3) . . ?
C6 C1 C2 117.1(3) . . ?
N1 C7 C8 122.6(3) . . ?
N1 C7 C17 119.2(3) . . ?
C17 C7 C8 118.1(2) . . ?
C9 C8 C7 124.5(3) . . ?
C9 C8 C13 117.8(3) . . ?
C13 C8 C7 117.5(3) . . ?
C12 C11 H27 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C10 C11 H27 120.0 . . ?
C14 C17 C18 120.5(3) . . ?
C7 C17 C18 121.3(2) . . ?
C7 C17 C14 118.1(3) . . ?
C1 C6 H30 119.2 . . ?
C5 C6 C1 121.6(3) . . ?
C5 C6 H30 119.2 . . ?
O4 C16 H33A 109.5 . . ?
O4 C16 H33B 109.5 . . ?
O4 C16 H33C 109.5 . . ?
H33A C16 H33B 109.5 . . ?
H33A C16 H33C 109.5 . . ?
H33B C16 H33C 109.5 . . ?
C2 C3 H34 120.2 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H34 120.2 . . ?
C3 C4 H34C 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H34C 120.3 . . ?
C8 C9 H35 119.7 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H35 119.7 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H40 119.7 . . ?
C4 C5 H40 119.7 . . ?
N2 C13 C12 117.7(3) . . ?
N2 C13 C8 122.6(3) . . ?
C12 C13 C8 119.4(3) . . ?
C11 C10 H44 119.5 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H44 119.5 . . ?

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
Br1 C2 C1 N1 -3.0(4) . . . . ?
Br1 C2 C1 C6 -179.1(2) . . . . ?
Br1 C2 C3 C4 -178.5(2) . . . . ?
O4 C15 C14 N2 -120.4(3) . . . . ?
O4 C15 C14 C17 55.4(4) . . . . ?
O2 C18 C17 C14 25.0(4) . . . . ?
O2 C18 C17 C7 -153.9(3) . . . . ?
O1 C18 C17 C14 -157.3(3) . . . . ?
O1 C18 C17 C7 23.9(5) . . . . ?
O3 C15 C14 N2 54.9(4) . . . . ?
O3 C15 C14 C17 -129.3(3) . . . . ?
N2 C14 C17 C18 -169.6(3) . . . . ?
N2 C14 C17 C7 9.2(5) . . . . ?
N1 C1 C6 C5 -178.3(3) . . . . ?
N1 C7 C8 C9 -7.1(5) . . . . ?
N1 C7 C8 C13 176.7(3) . . . . ?
N1 C7 C17 C18 -6.0(5) . . . . ?
N1 C7 C17 C14 175.2(3) . . . . ?
C19 O2 C18 O1 3.8(5) . . . . ?
C19 O2 C18 C17 -178.3(3) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
C15 C14 C17 C18 15.0(4) . . . . ?
C15 C14 C17 C7 -166.1(3) . . . . ?
C12 C11 C10 C9 2.6(6) . . . . ?
C14 N2 C13 C12 -177.4(3) . . . . ?
C14 N2 C13 C8 -2.6(5) . . . . ?
C1 N1 C7 C8 -37.1(5) . . . . ?
C1 N1 C7 C17 145.4(3) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
C1 C6 C5 C4 2.0(5) . . . . ?
C7 N1 C1 C2 160.4(3) . . . . ?
C7 N1 C1 C6 -23.8(5) . . . . ?
C7 C8 C9 C10 179.0(3) . . . . ?
C7 C8 C13 N2 8.7(5) . . . . ?
C7 C8 C13 C12 -176.6(3) . . . . ?
C8 C7 C17 C18 176.5(3) . . . . ?
C8 C7 C17 C14 -2.4(4) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
C11 C12 C13 N2 170.4(4) . . . . ?
C11 C12 C13 C8 -4.5(6) . . . . ?
C17 C7 C8 C9 170.4(3) . . . . ?
C17 C7 C8 C13 -5.8(4) . . . . ?
C16 O4 C15 O3 5.2(4) . . . . ?
C16 O4 C15 C14 -179.6(2) . . . . ?
C3 C2 C1 N1 176.5(3) . . . . ?
C3 C2 C1 C6 0.5(4) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C9 C8 C13 N2 -167.7(3) . . . . ?
C9 C8 C13 C12 7.0(5) . . . . ?
C13 N2 C14 C15 169.0(3) . . . . ?
C13 N2 C14 C17 -6.6(5) . . . . ?
C13 C12 C11 C10 -0.3(6) . . . . ?
C13 C8 C9 C10 -4.8(5) . . . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_exp_2959_216
_database_code_depnum_ccdc_archive 'CCDC 1059037'
_audit_update_record             
;
2015-04-12 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
_audit_creation_date             2013-12-31
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            4-aminoquinoline
_chemical_name_systematic        
'dimethyl 4-(benzylamino)quinoline-2,3-dicarboxylate'
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_chemical_melting_point          '80-82 degree celcius'
_chemical_oxdiff_formula         'C20 H18 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.3579(11)
_cell_length_b                   10.6509(6)
_cell_length_c                   16.8297(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.958(7)
_cell_angle_gamma                90.00
_cell_volume                     3456.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      70.5803
_cell_measurement_theta_min      4.5815
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6934
_diffrn_reflns_theta_full        70.67
_diffrn_reflns_theta_max         70.67
_diffrn_reflns_theta_min         4.59
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   12.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -77.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  111.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -63.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   12.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -16.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  6 omega   67.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   86.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  160.0000  -41.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   46.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
  9 omega  100.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega   88.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   89.00  167.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 13 omega   80.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 14 omega   60.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   44.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 16 omega   79.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 55
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0098092000
_diffrn_orient_matrix_UB_12      0.0777992000
_diffrn_orient_matrix_UB_13      0.0754225000
_diffrn_orient_matrix_UB_21      0.0191828000
_diffrn_orient_matrix_UB_22      0.1201429000
_diffrn_orient_matrix_UB_23      -0.0440123000
_diffrn_orient_matrix_UB_31      -0.0769290000
_diffrn_orient_matrix_UB_32      0.0201805000
_diffrn_orient_matrix_UB_33      -0.0287784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2067
_reflns_number_total             3258
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1702
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.10199(9) 0.87131(15) 0.24448(10) 0.0637(5) Uani 1 1 d . . .
O2 O 0.20610(8) 0.75149(17) 0.17074(10) 0.0650(5) Uani 1 1 d . . .
N1 N 0.10721(10) 0.50373(18) 0.18894(13) 0.0607(5) Uani 1 1 d . . .
O1 O 0.21152(10) 0.63878(17) 0.28349(11) 0.0762(6) Uani 1 1 d . . .
O3 O 0.02952(10) 0.92544(15) 0.14002(12) 0.0711(5) Uani 1 1 d . . .
C4 C -0.00914(12) 0.5203(2) 0.11830(14) 0.0544(6) Uani 1 1 d . . .
C3 C -0.00511(12) 0.6562(2) 0.12294(14) 0.0531(6) Uani 1 1 d . . .
C1 C 0.10967(12) 0.6268(2) 0.19182(13) 0.0517(6) Uani 1 1 d . . .
N2 N -0.05436(11) 0.7348(2) 0.09127(14) 0.0677(6) Uani 1 1 d . . .
H2 H -0.0429 0.8127 0.0948 0.081 Uiso 1 1 calc R . .
C12 C 0.06034(12) 0.8442(2) 0.17920(14) 0.0530(6) Uani 1 1 d . . .
C20 C -0.22175(13) 0.8577(2) 0.07431(15) 0.0607(6) Uani 1 1 d . . .
H20 H -0.2399 0.7949 0.1048 0.073 Uiso 1 1 calc R . .
C9 C 0.04734(13) 0.4509(2) 0.15407(15) 0.0584(6) Uani 1 1 d . . .
C10 C 0.18036(13) 0.6737(2) 0.22263(15) 0.0569(6) Uani 1 1 d . . .
C14 C -0.12320(12) 0.7135(2) 0.05225(16) 0.0613(6) Uani 1 1 d . . .
H14a H -0.1491 0.6587 0.0848 0.074 Uiso 1 1 calc R . .
H14b H -0.1196 0.6730 0.0012 0.074 Uiso 1 1 calc R . .
C15 C -0.16046(12) 0.8369(2) 0.04005(14) 0.0545(6) Uani 1 1 d . . .
C8 C 0.04524(16) 0.3185(2) 0.15185(19) 0.0755(8) Uani 1 1 d . . .
H8 H 0.0823 0.2733 0.1762 0.091 Uiso 1 1 calc R . .
C7 C -0.00955(16) 0.2555(3) 0.1151(2) 0.0789(9) Uani 1 1 d . . .
H7 H -0.0102 0.1682 0.1147 0.095 Uiso 1 1 calc R . .
C2 C 0.05544(12) 0.7083(2) 0.16407(13) 0.0493(5) Uani 1 1 d . . .
C6 C -0.06413(17) 0.3225(3) 0.0786(2) 0.0835(9) Uani 1 1 d . . .
H6 H -0.1015 0.2797 0.0528 0.100 Uiso 1 1 calc R . .
C18 C -0.23028(18) 1.0627(3) 0.01879(19) 0.0809(9) Uani 1 1 d . . .
H18 H -0.2536 1.1388 0.0118 0.097 Uiso 1 1 calc R . .
C19 C -0.25639(15) 0.9707(3) 0.06387(17) 0.0703(7) Uani 1 1 d . . .
H19 H -0.2974 0.9839 0.0876 0.084 Uiso 1 1 calc R . .
C16 C -0.13418(15) 0.9310(3) -0.00553(16) 0.0697(7) Uani 1 1 d . . .
H16 H -0.0929 0.9186 -0.0288 0.084 Uiso 1 1 calc R . .
C5 C -0.06457(16) 0.4512(3) 0.0794(2) 0.0803(9) Uani 1 1 d . . .
H5 H -0.1021 0.4939 0.0539 0.096 Uiso 1 1 calc R . .
C13 C 0.11613(16) 1.0031(2) 0.25907(18) 0.0766(8) Uani 1 1 d . . .
H13a H 0.1386 1.0377 0.2153 0.115 Uiso 1 1 calc R . .
H13b H 0.1458 1.0123 0.3074 0.115 Uiso 1 1 calc R . .
H13c H 0.0734 1.0468 0.2642 0.115 Uiso 1 1 calc R . .
C17 C -0.16969(18) 1.0438(3) -0.01631(19) 0.0807(9) Uani 1 1 d . . .
H17 H -0.1524 1.1067 -0.0474 0.097 Uiso 1 1 calc R . .
C11 C 0.27270(15) 0.8073(3) 0.19538(19) 0.0839(9) Uani 1 1 d . . .
H11a H 0.2815 0.8753 0.1602 0.126 Uiso 1 1 calc R . .
H11b H 0.3084 0.7451 0.1935 0.126 Uiso 1 1 calc R . .
H11c H 0.2724 0.8385 0.2489 0.126 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C12 1.337(3) . ?
O4 C13 1.447(3) . ?
O2 C10 1.331(3) . ?
O2 C11 1.447(3) . ?
N1 C1 1.312(3) . ?
N1 C9 1.374(3) . ?
O1 C10 1.202(3) . ?
O3 C12 1.213(3) . ?
C4 C3 1.451(3) . ?
C4 C9 1.411(3) . ?
C4 C5 1.415(4) . ?
C3 N2 1.344(3) . ?
C3 C2 1.421(3) . ?
C1 C10 1.506(3) . ?
C1 C2 1.410(3) . ?
N2 C14 1.452(3) . ?
C12 C2 1.472(3) . ?
C20 C15 1.381(3) . ?
C20 C19 1.381(4) . ?
C9 C8 1.410(3) . ?
C14 C15 1.505(3) . ?
C15 C16 1.385(4) . ?
C8 C7 1.358(4) . ?
C7 C6 1.375(4) . ?
C6 C5 1.370(4) . ?
C18 C19 1.363(4) . ?
C18 C17 1.373(4) . ?
C16 C17 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O4 C13 116.14(19) . . ?
C10 O2 C11 116.2(2) . . ?
C1 N1 C9 116.9(2) . . ?
C9 C4 C3 117.6(2) . . ?
C9 C4 C5 116.9(2) . . ?
C5 C4 C3 125.4(2) . . ?
N2 C3 C4 124.5(2) . . ?
N2 C3 C2 118.5(2) . . ?
C2 C3 C4 117.0(2) . . ?
N1 C1 C10 111.9(2) . . ?
N1 C1 C2 125.4(2) . . ?
C2 C1 C10 122.5(2) . . ?
C3 N2 C14 132.4(2) . . ?
O4 C12 C2 112.3(2) . . ?
O3 C12 O4 121.7(2) . . ?
O3 C12 C2 125.9(2) . . ?
C15 C20 C19 120.8(3) . . ?
N1 C9 C4 124.1(2) . . ?
N1 C9 C8 116.2(2) . . ?
C8 C9 C4 119.5(2) . . ?
O2 C10 C1 111.2(2) . . ?
O1 C10 O2 124.3(2) . . ?
O1 C10 C1 124.4(2) . . ?
N2 C14 C15 109.6(2) . . ?
C20 C15 C14 120.1(2) . . ?
C20 C15 C16 119.0(2) . . ?
C16 C15 C14 120.8(2) . . ?
C7 C8 C9 121.7(3) . . ?
C8 C7 C6 119.1(3) . . ?
C3 C2 C12 120.4(2) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 C12 120.9(2) . . ?
C5 C6 C7 121.3(3) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C20 119.9(3) . . ?
C15 C16 C17 119.8(3) . . ?
C6 C5 C4 121.4(3) . . ?
C18 C17 C16 120.2(3) . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
