# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_dks-172
_database_code_depnum_ccdc_archive 'CCDC 995671'
_audit_update_record             
;
2014-04-05 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_date             2014-01-29T22:33:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
N-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline
;
_chemical_name_common            'Compound 172'
_chemical_formula_sum            'C18 H22 N4 O2'
_chemical_formula_moiety         'C18 H22 N4 O2'
_chemical_formula_weight         326.39

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.8320(4)
_cell_length_b                   4.8941(2)
_cell_length_c                   23.9340(7)
_cell_angle_alpha                90.000
_cell_angle_beta                 108.015(2)
_cell_angle_gamma                90.000
_cell_volume                     1652.15(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4493
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      28.7

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             696


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        DENZO-SMN; Otwinowski & Minor, 1997
;
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.996

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.0150412
_diffrn_orient_matrix_ub_12      0.1265995
_diffrn_orient_matrix_ub_13      -0.0344553
_diffrn_orient_matrix_ub_21      0.0181049
_diffrn_orient_matrix_ub_22      0.1597043
_diffrn_orient_matrix_ub_23      0.0272518
_diffrn_orient_matrix_ub_31      0.0669035
_diffrn_orient_matrix_ub_32      -0.0147275
_diffrn_orient_matrix_ub_33      -0.0006677
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_number            10299
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         28.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_number_total             4234
_reflns_number_gt                3068
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0564P)²+0.4300P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4234
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.04386(7) 0.2526(2) 0.01672(4) 0.0233(2) Uani 1 d . .
O2 O -0.12087(7) 0.5929(2) 0.03823(4) 0.0254(2) Uani 1 d . .
N2 N 0.11651(8) 0.0838(2) 0.09251(5) 0.0185(3) Uani 1 d . .
C11 C 0.19853(9) -0.0951(3) 0.11084(6) 0.0191(3) Uani 1 d . .
H11A H 0.1944 -0.2291 0.0792 0.023 Uiso 1 calc . .
H11B H 0.1964 -0.1981 0.146 0.023 Uiso 1 calc . .
C2 C 0.09242(9) 0.2619(3) 0.12866(6) 0.0160(3) Uani 1 d . .
N1 N -0.05408(7) 0.4277(2) 0.05213(5) 0.0187(3) Uani 1 d . .
C5 C 0.04941(9) 0.6412(3) 0.20668(6) 0.0183(3) Uani 1 d . .
H5 H 0.035 0.7699 0.2324 0.022 Uiso 1 calc . .
N4 N 0.32672(8) 0.6521(2) 0.39174(5) 0.0207(3) Uani 1 d . .
C12 C 0.29322(9) 0.0517(3) 0.12512(6) 0.0179(3) Uani 1 d . .
N3 N 0.18672(7) 0.4770(2) 0.28592(5) 0.0175(2) Uani 1 d . .
C1 C 0.01147(9) 0.4360(3) 0.11019(5) 0.0163(3) Uani 1 d . .
C4 C 0.12934(9) 0.4663(3) 0.22735(5) 0.0163(3) Uani 1 d . .
C6 C -0.00668(9) 0.6227(3) 0.14939(6) 0.0185(3) Uani 1 d . .
H6 H -0.0598 0.741 0.1359 0.022 Uiso 1 calc . .
C3 C 0.14907(9) 0.2843(3) 0.18797(5) 0.0167(3) Uani 1 d . .
H3 H 0.2032 0.1698 0.2016 0.02 Uiso 1 calc . .
C8 C 0.34005(10) 0.3990(3) 0.36339(6) 0.0217(3) Uani 1 d . .
H8A H 0.3162 0.2434 0.3812 0.026 Uiso 1 calc . .
H8B H 0.4085 0.3696 0.3695 0.026 Uiso 1 calc . .
C9 C 0.16825(9) 0.7007(3) 0.32170(6) 0.0202(3) Uani 1 d . .
H9A H 0.1001 0.7017 0.3184 0.024 Uiso 1 calc . .
H9B H 0.1831 0.8769 0.3062 0.024 Uiso 1 calc . .
C13 C 0.30835(10) 0.2569(3) 0.08876(6) 0.0209(3) Uani 1 d . .
H13 H 0.2585 0.3097 0.0548 0.025 Uiso 1 calc . .
C10 C 0.22630(10) 0.6755(3) 0.38574(6) 0.0233(3) Uani 1 d . .
H10A H 0.2158 0.8381 0.4075 0.028 Uiso 1 calc . .
H10B H 0.2056 0.5122 0.4029 0.028 Uiso 1 calc . .
C15 C 0.46975(10) 0.3087(3) 0.15141(6) 0.0251(3) Uani 1 d . .
H15 H 0.5297 0.3962 0.1603 0.03 Uiso 1 calc . .
C7 C 0.28748(9) 0.4106(3) 0.29812(6) 0.0208(3) Uani 1 d . .
H7A H 0.3174 0.5501 0.2796 0.025 Uiso 1 calc . .
H7B H 0.2932 0.2316 0.2802 0.025 Uiso 1 calc . .
C17 C 0.36737(9) -0.0225(3) 0.17465(6) 0.0209(3) Uani 1 d . .
H17 H 0.3578 -0.1618 0.1999 0.025 Uiso 1 calc . .
C16 C 0.45506(10) 0.1048(3) 0.18760(6) 0.0245(3) Uani 1 d . .
H16 H 0.5051 0.0516 0.2214 0.029 Uiso 1 calc . .
C14 C 0.39614(10) 0.3849(3) 0.10198(7) 0.0261(3) Uani 1 d . .
H14 H 0.4059 0.5254 0.0771 0.031 Uiso 1 calc . .
C41 C 0.38434(11) 0.6559(4) 0.45341(6) 0.0306(4) Uani 1 d . .
H41A H 0.374 0.8281 0.4714 0.046 Uiso 1 calc . .
H41B H 0.4515 0.6397 0.4562 0.046 Uiso 1 calc . .
H41C H 0.3663 0.5024 0.474 0.046 Uiso 1 calc . .
H2 H 0.0770(11) 0.076(4) 0.0564(8) 0.030(5) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.2470(15) . ?
O2 N1 1.2418(14) . ?
N2 C2 1.3517(17) . ?
N2 C11 1.4520(17) . ?
N2 H2 0.882(17) . ?
C11 C12 1.5195(18) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C2 C3 1.4127(17) . ?
C2 C1 1.4265(18) . ?
N1 C1 1.4290(16) . ?
C5 C6 1.3693(18) . ?
C5 C4 1.4212(18) . ?
C5 H5 0.95 . ?
N4 C8 1.4549(18) . ?
N4 C10 1.4560(17) . ?
N4 C41 1.4592(17) . ?
C12 C13 1.392(2) . ?
C12 C17 1.3930(18) . ?
N3 C4 1.3979(16) . ?
N3 C9 1.4671(17) . ?
N3 C7 1.4679(16) . ?
C1 C6 1.3941(19) . ?
C4 C3 1.3920(18) . ?
C6 H6 0.95 . ?
C3 H3 0.95 . ?
C8 C7 1.5160(18) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.5132(18) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C13 C14 1.390(2) . ?
C13 H13 0.95 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C15 C16 1.382(2) . ?
C15 C14 1.390(2) . ?
C15 H15 0.95 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C17 C16 1.3880(19) . ?
C17 H17 0.95 . ?
C16 H16 0.95 . ?
C14 H14 0.95 . ?
C41 H41A 0.98 . ?
C41 H41B 0.98 . ?
C41 H41C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C11 123.91(11) . . ?
C2 N2 H2 115.4(11) . . ?
C11 N2 H2 120.6(11) . . ?
N2 C11 C12 114.38(12) . . ?
N2 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
N2 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N2 C2 C3 120.04(12) . . ?
N2 C2 C1 123.41(12) . . ?
C3 C2 C1 116.55(12) . . ?
O2 N1 O1 121.32(11) . . ?
O2 N1 C1 119.23(11) . . ?
O1 N1 C1 119.43(11) . . ?
C6 C5 C4 119.46(12) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C8 N4 C10 107.66(11) . . ?
C8 N4 C41 111.16(12) . . ?
C10 N4 C41 111.10(11) . . ?
C13 C12 C17 118.87(12) . . ?
C13 C12 C11 121.14(12) . . ?
C17 C12 C11 119.98(12) . . ?
C4 N3 C9 116.59(11) . . ?
C4 N3 C7 117.25(10) . . ?
C9 N3 C7 114.30(10) . . ?
C6 C1 C2 120.14(12) . . ?
C6 C1 N1 117.27(11) . . ?
C2 C1 N1 122.59(12) . . ?
C3 C4 N3 120.84(12) . . ?
C3 C4 C5 118.49(12) . . ?
N3 C4 C5 120.67(12) . . ?
C5 C6 C1 122.23(12) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C4 C3 C2 123.08(12) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N4 C8 C7 110.36(11) . . ?
N4 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
N4 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 C10 112.32(11) . . ?
N3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C14 C13 C12 120.24(13) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N4 C10 C9 110.53(11) . . ?
N4 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C16 C15 C14 119.51(13) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N3 C7 C8 112.38(11) . . ?
N3 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N3 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C16 C17 C12 120.77(13) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C15 C16 C17 120.17(13) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C15 C14 C13 120.44(14) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N4 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 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
C2 N2 C11 C12 -69.06(16) . . . . ?
C11 N2 C2 C3 0.80(19) . . . . ?
C11 N2 C2 C1 -179.79(12) . . . . ?
N2 C11 C12 C13 -44.58(17) . . . . ?
N2 C11 C12 C17 136.80(13) . . . . ?
N2 C2 C1 C6 -177.33(12) . . . . ?
C3 C2 C1 C6 2.09(18) . . . . ?
N2 C2 C1 N1 3.1(2) . . . . ?
C3 C2 C1 N1 -177.51(12) . . . . ?
O2 N1 C1 C6 3.40(18) . . . . ?
O1 N1 C1 C6 -175.64(11) . . . . ?
O2 N1 C1 C2 -176.99(12) . . . . ?
O1 N1 C1 C2 3.96(19) . . . . ?
C9 N3 C4 C3 171.59(12) . . . . ?
C7 N3 C4 C3 30.75(18) . . . . ?
C9 N3 C4 C5 -8.45(18) . . . . ?
C7 N3 C4 C5 -149.29(12) . . . . ?
C6 C5 C4 C3 1.26(19) . . . . ?
C6 C5 C4 N3 -178.70(12) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 C5 -2.1(2) . . . . ?
N1 C1 C6 C5 177.56(12) . . . . ?
N3 C4 C3 C2 178.81(12) . . . . ?
C5 C4 C3 C2 -1.2(2) . . . . ?
N2 C2 C3 C4 178.93(12) . . . . ?
C1 C2 C3 C4 -0.51(19) . . . . ?
C10 N4 C8 C7 63.79(14) . . . . ?
C41 N4 C8 C7 -174.32(11) . . . . ?
C4 N3 C9 C10 173.52(11) . . . . ?
C7 N3 C9 C10 -44.50(15) . . . . ?
C17 C12 C13 C14 -0.1(2) . . . . ?
C11 C12 C13 C14 -178.71(13) . . . . ?
C8 N4 C10 C9 -63.91(15) . . . . ?
C41 N4 C10 C9 174.15(12) . . . . ?
N3 C9 C10 N4 54.40(16) . . . . ?
C4 N3 C7 C8 -173.77(12) . . . . ?
C9 N3 C7 C8 44.52(16) . . . . ?
N4 C8 C7 N3 -54.37(16) . . . . ?
C13 C12 C17 C16 -0.2(2) . . . . ?
C11 C12 C17 C16 178.42(13) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C12 C17 C16 C15 0.3(2) . . . . ?
C16 C15 C14 C13 -0.2(2) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.882(17) 1.953(17) 2.6385(15) 133.5(15) .
N2 H2 O1 0.882(17) 2.314(18) 2.9938(15) 133.9(14) 3
C10 H10A O2 0.99 2.52 3.4192(18) 150.8 2
C10 H10A O2 0.99 2.52 3.4192(18) 150.8 2
N2 H2 O1 0.882(17) 1.953(17) 2.6385(15) 133.5(15) .
N2 H2 O1 0.882(17) 2.314(18) 2.9938(15) 133.9(14) 3

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 995672'
_audit_update_record             
;
2014-04-05 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_date             2014-02-04T22:15:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]-2,3-dihydro-1H-isoindole
;
_chemical_name_common            'Compound 180'
_chemical_formula_sum            'C19 H22 N4 O2'
_chemical_formula_moiety         'C19 H22 N4 O2'
_chemical_formula_weight         338.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2516(3)
_cell_length_b                   18.4177(5)
_cell_length_c                   12.6426(3)
_cell_angle_alpha                90
_cell_angle_beta                 128.998(2)
_cell_angle_gamma                90
_cell_volume                     1674.18(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4143
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             720


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        DENZO-SMN; Otwinowski & Minor, 1997
;
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.982

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.0880136
_diffrn_orient_matrix_ub_12      0.0005177
_diffrn_orient_matrix_ub_13      -0.07028
_diffrn_orient_matrix_ub_21      0.0374164
_diffrn_orient_matrix_ub_22      -0.0437593
_diffrn_orient_matrix_ub_23      -0.0441117
_diffrn_orient_matrix_ub_31      -0.0523455
_diffrn_orient_matrix_ub_32      -0.0321382
_diffrn_orient_matrix_ub_33      0.0589294
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_number            9948
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_number_total             3819
_reflns_number_gt                3355
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0470P)²+0.6953P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3819
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.76415(11) 0.57053(4) 0.34491(9) 0.02030(19) Uani 1 d . .
O2 O 0.77599(12) 0.68826(4) 0.34494(9) 0.02124(19) Uani 1 d . .
N1 N 0.72049(13) 0.63095(5) 0.36002(10) 0.0162(2) Uani 1 d . .
N4 N 0.16305(14) 0.66356(5) 0.69297(10) 0.0181(2) Uani 1 d . .
N3 N 0.36698(13) 0.64753(5) 0.59267(10) 0.0153(2) Uani 1 d . .
N2 N 0.39228(13) 0.53471(5) 0.25874(9) 0.0147(2) Uani 1 d . .
C6 C 0.66428(16) 0.68795(6) 0.50099(12) 0.0177(2) Uani 1 d . .
H6 H 0.7595 0.721 0.5252 0.021 Uiso 1 calc . .
C1 C 0.60818(15) 0.63508(6) 0.40271(11) 0.0154(2) Uani 1 d . .
C12 C 0.27133(15) 0.48007(6) 0.05267(11) 0.0156(2) Uani 1 d . .
C18 C 0.24812(15) 0.48336(6) 0.22858(11) 0.0144(2) Uani 1 d . .
H18A H 0.1378 0.5093 0.2055 0.017 Uiso 1 calc . .
H18B H 0.2968 0.4504 0.3063 0.017 Uiso 1 calc . .
C2 C 0.46212(15) 0.58604(6) 0.35983(11) 0.0140(2) Uani 1 d . .
C14 C 0.10612(16) 0.37804(6) 0.05096(12) 0.0178(2) Uani 1 d . .
H14 H 0.06 0.3524 0.0894 0.021 Uiso 1 calc . .
C17 C 0.24541(16) 0.45342(7) -0.06120(12) 0.0186(2) Uani 1 d . .
H17 H 0.2933 0.4789 -0.0985 0.022 Uiso 1 calc . .
C4 C 0.44241(15) 0.64498(6) 0.52671(11) 0.0143(2) Uani 1 d . .
C11 C 0.37314(16) 0.54692(6) 0.13511(11) 0.0171(2) Uani 1 d . .
H11A H 0.4962 0.5508 0.1571 0.02 Uiso 1 calc . .
H11B H 0.3003 0.5914 0.0866 0.02 Uiso 1 calc . .
C15 C 0.07806(16) 0.35156(6) -0.06423(12) 0.0196(2) Uani 1 d . .
H15 H 0.0107 0.3077 -0.1053 0.024 Uiso 1 calc . .
C7 C 0.21829(16) 0.59671(6) 0.55232(12) 0.0171(2) Uani 1 d . .
H7B H 0.248 0.548 0.5376 0.02 Uiso 1 calc . .
H7A H 0.1 0.613 0.4655 0.02 Uiso 1 calc . .
C13 C 0.20286(15) 0.44267(6) 0.10802(11) 0.0148(2) Uani 1 d . .
C9 C 0.34692(18) 0.71812(6) 0.63593(13) 0.0206(2) Uani 1 d . .
H9A H 0.2371 0.7437 0.5564 0.025 Uiso 1 calc . .
H9B H 0.4582 0.7482 0.6727 0.025 Uiso 1 calc . .
C5 C 0.58632(16) 0.69365(6) 0.56379(11) 0.0169(2) Uani 1 d . .
H5 H 0.6282 0.7297 0.6312 0.02 Uiso 1 calc . .
C3 C 0.38314(15) 0.59341(6) 0.42499(11) 0.0143(2) Uani 1 d . .
H3 H 0.2844 0.5617 0.3986 0.017 Uiso 1 calc . .
C10 C 0.32421(16) 0.70888(6) 0.74375(12) 0.0194(2) Uani 1 d . .
H10A H 0.4375 0.6862 0.8257 0.023 Uiso 1 calc . .
H10B H 0.3083 0.7571 0.77 0.023 Uiso 1 calc . .
C16 C 0.14761(16) 0.38859(7) -0.11950(12) 0.0203(2) Uani 1 d . .
H16 H 0.1285 0.3697 -0.1974 0.024 Uiso 1 calc . .
C8 C 0.19545(17) 0.59218(6) 0.66104(12) 0.0191(2) Uani 1 d . .
H8A H 0.0894 0.5599 0.6291 0.023 Uiso 1 calc . .
H8B H 0.3089 0.5706 0.7446 0.023 Uiso 1 calc . .
C41 C 0.1373(2) 0.65729(7) 0.79500(13) 0.0266(3) Uani 1 d . .
H41A H 0.0286 0.6268 0.7596 0.04 Uiso 1 calc . .
H41B H 0.1177 0.7056 0.8164 0.04 Uiso 1 calc . .
H41C H 0.2481 0.6352 0.8777 0.04 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.2391(12) . ?
O2 N1 1.2398(12) . ?
N1 C1 1.4430(14) . ?
N4 C41 1.4565(15) . ?
N4 C10 1.4585(15) . ?
N4 C8 1.4606(15) . ?
N3 C4 1.3847(14) . ?
N3 C7 1.4647(14) . ?
N3 C9 1.4669(14) . ?
N2 C2 1.3803(14) . ?
N2 C11 1.4753(13) . ?
N2 C18 1.4759(14) . ?
C6 C5 1.3720(16) . ?
C6 C1 1.3963(16) . ?
C6 H6 0.95 . ?
C1 C2 1.4190(15) . ?
C12 C13 1.3868(15) . ?
C12 C17 1.3916(15) . ?
C12 C11 1.5013(16) . ?
C18 C13 1.5023(15) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C2 C3 1.4102(15) . ?
C14 C13 1.3877(16) . ?
C14 C15 1.3966(16) . ?
C14 H14 0.95 . ?
C17 C16 1.3958(17) . ?
C17 H17 0.95 . ?
C4 C3 1.4032(15) . ?
C4 C5 1.4179(15) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C15 C16 1.3904(18) . ?
C15 H15 0.95 . ?
C7 C8 1.5186(15) . ?
C7 H7B 0.99 . ?
C7 H7A 0.99 . ?
C9 C10 1.5139(16) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C5 H5 0.95 . ?
C3 H3 0.95 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C16 H16 0.95 . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C41 H41A 0.98 . ?
C41 H41B 0.98 . ?
C41 H41C 0.98 . ?

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
O1 N1 O2 122.29(9) . . ?
O1 N1 C1 119.10(9) . . ?
O2 N1 C1 118.55(9) . . ?
C41 N4 C10 110.33(10) . . ?
C41 N4 C8 110.48(9) . . ?
C10 N4 C8 107.82(9) . . ?
C4 N3 C7 119.17(9) . . ?
C4 N3 C9 118.98(9) . . ?
C7 N3 C9 112.64(9) . . ?
C2 N2 C11 123.42(9) . . ?
C2 N2 C18 119.90(9) . . ?
C11 N2 C18 109.72(8) . . ?
C5 C6 C1 122.13(10) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C6 C1 C2 121.01(10) . . ?
C6 C1 N1 114.68(10) . . ?
C2 C1 N1 124.08(10) . . ?
C13 C12 C17 120.72(11) . . ?
C13 C12 C11 110.07(9) . . ?
C17 C12 C11 129.19(10) . . ?
N2 C18 C13 102.21(8) . . ?
N2 C18 H18A 111.3 . . ?
C13 C18 H18A 111.3 . . ?
N2 C18 H18B 111.3 . . ?
C13 C18 H18B 111.3 . . ?
H18A C18 H18B 109.2 . . ?
N2 C2 C3 119.61(10) . . ?
N2 C2 C1 124.61(10) . . ?
C3 C2 C1 115.76(10) . . ?
C13 C14 C15 118.53(11) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C12 C17 C16 118.71(11) . . ?
C12 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
N3 C4 C3 121.37(10) . . ?
N3 C4 C5 120.25(10) . . ?
C3 C4 C5 118.36(10) . . ?
N2 C11 C12 102.42(9) . . ?
N2 C11 H11A 111.3 . . ?
C12 C11 H11A 111.3 . . ?
N2 C11 H11B 111.3 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C16 C15 C14 120.77(11) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N3 C7 C8 110.79(9) . . ?
N3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
N3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
H7B C7 H7A 108.1 . . ?
C12 C13 C14 120.91(10) . . ?
C12 C13 C18 109.88(10) . . ?
C14 C13 C18 129.21(10) . . ?
N3 C9 C10 110.97(10) . . ?
N3 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C6 C5 C4 119.11(10) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C4 C3 C2 123.58(10) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
N4 C10 C9 110.53(9) . . ?
N4 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C15 C16 C17 120.36(11) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
N4 C8 C7 111.74(9) . . ?
N4 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N4 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N4 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 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
C5 C6 C1 C2 2.20(17) . . . . ?
C5 C6 C1 N1 -172.47(10) . . . . ?
O1 N1 C1 C6 137.55(11) . . . . ?
O2 N1 C1 C6 -39.66(14) . . . . ?
O1 N1 C1 C2 -36.93(15) . . . . ?
O2 N1 C1 C2 145.87(11) . . . . ?
C2 N2 C18 C13 175.65(9) . . . . ?
C11 N2 C18 C13 23.90(11) . . . . ?
C11 N2 C2 C3 141.93(11) . . . . ?
C18 N2 C2 C3 -5.81(15) . . . . ?
C11 N2 C2 C1 -36.18(16) . . . . ?
C18 N2 C2 C1 176.08(10) . . . . ?
C6 C1 C2 N2 176.65(10) . . . . ?
N1 C1 C2 N2 -9.21(17) . . . . ?
C6 C1 C2 C3 -1.53(16) . . . . ?
N1 C1 C2 C3 172.61(10) . . . . ?
C13 C12 C17 C16 0.56(16) . . . . ?
C11 C12 C17 C16 178.73(11) . . . . ?
C7 N3 C4 C3 -1.89(15) . . . . ?
C9 N3 C4 C3 -146.28(11) . . . . ?
C7 N3 C4 C5 179.93(10) . . . . ?
C9 N3 C4 C5 35.53(15) . . . . ?
C2 N2 C11 C12 -173.34(9) . . . . ?
C18 N2 C11 C12 -22.79(11) . . . . ?
C13 C12 C11 N2 12.45(12) . . . . ?
C17 C12 C11 N2 -165.87(11) . . . . ?
C13 C14 C15 C16 0.84(17) . . . . ?
C4 N3 C7 C8 162.89(10) . . . . ?
C9 N3 C7 C8 -50.60(13) . . . . ?
C17 C12 C13 C14 -0.33(17) . . . . ?
C11 C12 C13 C14 -178.81(10) . . . . ?
C17 C12 C13 C18 -179.46(10) . . . . ?
C11 C12 C13 C18 2.05(12) . . . . ?
C15 C14 C13 C12 -0.37(16) . . . . ?
C15 C14 C13 C18 178.58(11) . . . . ?
N2 C18 C13 C12 -15.64(11) . . . . ?
N2 C18 C13 C14 165.32(11) . . . . ?
C4 N3 C9 C10 -161.21(10) . . . . ?
C7 N3 C9 C10 52.22(13) . . . . ?
C1 C6 C5 C4 -0.84(17) . . . . ?
N3 C4 C5 C6 177.20(10) . . . . ?
C3 C4 C5 C6 -1.04(16) . . . . ?
N3 C4 C3 C2 -176.54(10) . . . . ?
C5 C4 C3 C2 1.68(16) . . . . ?
N2 C2 C3 C4 -178.66(10) . . . . ?
C1 C2 C3 C4 -0.39(16) . . . . ?
C41 N4 C10 C9 -177.67(10) . . . . ?
C8 N4 C10 C9 61.61(12) . . . . ?
N3 C9 C10 N4 -58.05(13) . . . . ?
C14 C15 C16 C17 -0.61(17) . . . . ?
C12 C17 C16 C15 -0.10(17) . . . . ?
C41 N4 C8 C7 178.63(10) . . . . ?
C10 N4 C8 C7 -60.74(12) . . . . ?
N3 C7 C8 N4 55.51(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11A O1 0.99 2.12 2.8695(14) 130.8 .
C11 H11A N1 0.99 2.52 3.0508(15) 113.1 .
C7 H7A O1 0.99 2.57 3.3008(14) 130.2 1_455
C9 H9B O2 0.99 2.59 3.5371(15) 160.5 4_576
C5 H5 O2 0.95 2.61 3.5488(14) 170.6 4_576

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 995673'
_audit_update_record             
;
2014-04-05 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_date             2014-02-04T22:50:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]-1,2,3,4-tetrahydroisoquinoline
;
_chemical_formula_sum            'C20 H24 N4 O2'
_chemical_formula_moiety         'C20 H24 N4 O2'
_chemical_formula_weight         352.43

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6428(3)
_cell_length_b                   7.56690(10)
_cell_length_c                   16.1976(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.828(2)
_cell_angle_gamma                90
_cell_volume                     1762.75(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    8743
_cell_measurement_theta_min      3.0701
_cell_measurement_theta_max      71.0969

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             752
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.25738
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3756
_diffrn_orient_matrix_ub_11      -0.0657472
_diffrn_orient_matrix_ub_12      -0.1573153
_diffrn_orient_matrix_ub_13      -0.0265129
_diffrn_orient_matrix_ub_21      -0.0844911
_diffrn_orient_matrix_ub_22      0.1240914
_diffrn_orient_matrix_ub_23      -0.0065819
_diffrn_orient_matrix_ub_31      0.0037463
_diffrn_orient_matrix_ub_32      0.0361355
_diffrn_orient_matrix_ub_33      -0.0928963
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_number            23634
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         71.236
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_number_total             3397
_reflns_number_gt                2901
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0517P)²+0.6023P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3397
_refine_ls_number_parameters     235
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.763
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25397(7) 0.03838(14) 0.58501(6) 0.0311(2) Uani 1 d . .
N2 N 0.24337(7) 0.29203(14) 0.45361(7) 0.0205(2) Uani 1 d . .
N3 N -0.08373(7) 0.35051(15) 0.33044(7) 0.0228(3) Uani 1 d . .
N1 N 0.18341(8) 0.11209(15) 0.60006(7) 0.0251(3) Uani 1 d . .
C4 C -0.01580(9) 0.31397(17) 0.39890(8) 0.0213(3) Uani 1 d . .
C3 C 0.07999(9) 0.32656(17) 0.39585(8) 0.0204(3) Uani 1 d . .
H3 H 0.0968 0.3733 0.3464 0.025 Uiso 1 calc . .
C2 C 0.15090(9) 0.27460(16) 0.46102(8) 0.0199(3) Uani 1 d . .
C12 C 0.36515(9) 0.30521(17) 0.36814(8) 0.0215(3) Uani 1 d . .
N4 N -0.22814(7) 0.42453(15) 0.18861(7) 0.0226(3) Uani 1 d . .
C8 C -0.13597(9) 0.37004(18) 0.17738(8) 0.0243(3) Uani 1 d . .
H8A H -0.1218 0.4255 0.1259 0.029 Uiso 1 calc . .
H8B H -0.1349 0.2402 0.1701 0.029 Uiso 1 calc . .
C1 C 0.12304(9) 0.20606(18) 0.53420(8) 0.0228(3) Uani 1 d . .
C41 C -0.29860(10) 0.37980(19) 0.11542(9) 0.0274(3) Uani 1 d . .
H41A H -0.2832 0.4366 0.0654 0.041 Uiso 1 calc . .
H41B H -0.3595 0.4214 0.124 0.041 Uiso 1 calc . .
H41C H -0.3005 0.2513 0.1076 0.041 Uiso 1 calc . .
C13 C 0.43127(9) 0.27222(17) 0.44034(8) 0.0222(3) Uani 1 d . .
C10 C -0.24931(9) 0.3420(2) 0.26388(9) 0.0267(3) Uani 1 d . .
H10A H -0.2488 0.2119 0.2577 0.032 Uiso 1 calc . .
H10B H -0.3122 0.378 0.2714 0.032 Uiso 1 calc . .
C11 C 0.26387(9) 0.33861(17) 0.37139(8) 0.0205(3) Uani 1 d . .
H11A H 0.2493 0.465 0.3598 0.025 Uiso 1 calc . .
H11B H 0.2241 0.2677 0.3273 0.025 Uiso 1 calc . .
C6 C 0.02955(10) 0.2087(2) 0.54084(9) 0.0275(3) Uani 1 d . .
H6 H 0.013 0.1729 0.5923 0.033 Uiso 1 calc . .
C18 C 0.40556(9) 0.28160(19) 0.52630(8) 0.0251(3) Uani 1 d . .
H18A H 0.4535 0.3497 0.5646 0.03 Uiso 1 calc . .
H18B H 0.404 0.1607 0.5494 0.03 Uiso 1 calc . .
C19 C 0.31148(9) 0.36869(18) 0.52235(8) 0.0228(3) Uani 1 d . .
H19A H 0.2903 0.3511 0.5763 0.027 Uiso 1 calc . .
H19B H 0.3168 0.4973 0.5132 0.027 Uiso 1 calc . .
C14 C 0.52131(9) 0.22470(19) 0.43170(9) 0.0271(3) Uani 1 d . .
H14 H 0.5666 0.2004 0.4806 0.032 Uiso 1 calc . .
C7 C -0.06252(9) 0.42262(19) 0.25209(8) 0.0242(3) Uani 1 d . .
H7A H -0.0012 0.3784 0.2441 0.029 Uiso 1 calc . .
H7B H -0.0591 0.5531 0.256 0.029 Uiso 1 calc . .
C16 C 0.48063(10) 0.2526(2) 0.28206(10) 0.0345(4) Uani 1 d . .
H16 H 0.4975 0.2484 0.2283 0.041 Uiso 1 calc . .
C15 C 0.54574(10) 0.2124(2) 0.35386(10) 0.0324(3) Uani 1 d . .
H15 H 0.6068 0.1767 0.3492 0.039 Uiso 1 calc . .
C17 C 0.39097(10) 0.2988(2) 0.28965(9) 0.0285(3) Uani 1 d . .
H17 H 0.3465 0.3265 0.2407 0.034 Uiso 1 calc . .
C9 C -0.17905(9) 0.3958(2) 0.33975(9) 0.0293(3) Uani 1 d . .
H9A H -0.1833 0.5249 0.3483 0.035 Uiso 1 calc . .
H9B H -0.1934 0.3359 0.3901 0.035 Uiso 1 calc . .
O2 O 0.16095(7) 0.10165(15) 0.67015(6) 0.0334(3) Uani 1 d . .
C5 C -0.03855(9) 0.2603(2) 0.47685(9) 0.0271(3) Uani 1 d . .
H5 H -0.1015 0.2607 0.484 0.033 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.2379(15) . ?
N2 C2 1.3878(16) . ?
N2 C11 1.4623(16) . ?
N2 C19 1.4676(16) . ?
N3 C4 1.3715(17) . ?
N3 C7 1.4672(17) . ?
N3 C9 1.4722(16) . ?
N1 O2 1.2424(15) . ?
N1 C1 1.4391(17) . ?
C4 C3 1.4160(18) . ?
C4 C5 1.4242(19) . ?
C3 C2 1.3911(18) . ?
C3 H3 0.95 . ?
C2 C1 1.4221(18) . ?
C12 C17 1.3935(19) . ?
C12 C13 1.3936(18) . ?
C12 C11 1.5149(17) . ?
N4 C10 1.4541(17) . ?
N4 C8 1.4548(16) . ?
N4 C41 1.4577(17) . ?
C8 C7 1.5135(18) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C1 C6 1.3933(19) . ?
C41 H41A 0.98 . ?
C41 H41B 0.98 . ?
C41 H41C 0.98 . ?
C13 C14 1.3988(19) . ?
C13 C18 1.5107(18) . ?
C10 C9 1.5031(19) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C6 C5 1.3537(19) . ?
C6 H6 0.95 . ?
C18 C19 1.5175(18) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C14 C15 1.377(2) . ?
C14 H14 0.95 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C16 C17 1.386(2) . ?
C16 C15 1.392(2) . ?
C16 H16 0.95 . ?
C15 H15 0.95 . ?
C17 H17 0.95 . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C5 H5 0.95 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N2 C11 118.18(10) . . ?
C2 N2 C19 120.46(10) . . ?
C11 N2 C19 111.66(10) . . ?
C4 N3 C7 122.35(11) . . ?
C4 N3 C9 121.44(11) . . ?
C7 N3 C9 111.15(10) . . ?
O1 N1 O2 121.68(11) . . ?
O1 N1 C1 119.73(11) . . ?
O2 N1 C1 118.53(11) . . ?
N3 C4 C3 122.07(12) . . ?
N3 C4 C5 121.30(12) . . ?
C3 C4 C5 116.63(12) . . ?
C2 C3 C4 123.90(12) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
N2 C2 C3 120.59(11) . . ?
N2 C2 C1 122.96(11) . . ?
C3 C2 C1 116.45(11) . . ?
C17 C12 C13 119.64(12) . . ?
C17 C12 C11 118.20(11) . . ?
C13 C12 C11 122.07(12) . . ?
C10 N4 C8 109.39(10) . . ?
C10 N4 C41 110.63(11) . . ?
C8 N4 C41 111.35(11) . . ?
N4 C8 C7 111.23(11) . . ?
N4 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N4 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
C6 C1 C2 119.94(12) . . ?
C6 C1 N1 115.19(12) . . ?
C2 C1 N1 124.44(12) . . ?
N4 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C12 C13 C14 118.77(13) . . ?
C12 C13 C18 120.72(12) . . ?
C14 C13 C18 120.47(12) . . ?
N4 C10 C9 110.37(11) . . ?
N4 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N4 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 C12 111.18(10) . . ?
N2 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108 . . ?
C5 C6 C1 122.56(13) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
C13 C18 C19 111.28(11) . . ?
C13 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C13 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108 . . ?
N2 C19 C18 110.03(11) . . ?
N2 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
N2 C19 H19B 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C15 C14 C13 121.39(13) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
N3 C7 C8 111.08(11) . . ?
N3 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108 . . ?
C17 C16 C15 119.50(14) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C14 C15 C16 119.70(13) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C16 C17 C12 120.89(13) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
N3 C9 C10 111.69(11) . . ?
N3 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C6 C5 C4 119.98(12) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_dks-182
_database_code_depnum_ccdc_archive 'CCDC 995674'
_audit_update_record             
;
2014-04-05 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_date             2014-02-04T23:04:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
2-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]-2,3,4,5-tetrahydro-1H-2-benzazepine
;
_chemical_name_common            'Compound 182'
_chemical_formula_sum            'C21 H26 N4 O2'
_chemical_formula_moiety         'C21 H26 N4 O2'
_chemical_formula_weight         366.46

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5413(2)
_cell_length_b                   10.1771(2)
_cell_length_c                   11.0759(2)
_cell_angle_alpha                105.049(2)
_cell_angle_beta                 92.969(2)
_cell_angle_gamma                114.7100(10)
_cell_volume                     927.62(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3942
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             392
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        DENZO-SMN; Otwinowski & Minor, 1997
;
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.0757067
_diffrn_orient_matrix_ub_12      0.0763788
_diffrn_orient_matrix_ub_13      -0.0355495
_diffrn_orient_matrix_ub_21      0.0875016
_diffrn_orient_matrix_ub_22      -0.0163094
_diffrn_orient_matrix_ub_23      0.0360787
_diffrn_orient_matrix_ub_31      -0.0195535
_diffrn_orient_matrix_ub_32      -0.0827285
_diffrn_orient_matrix_ub_33      -0.0804825
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_number            7289
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.788
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_number_total             4191
_reflns_number_gt                3928
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0550P)²+0.3576P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4191
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.098
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39876(9) 0.50733(9) 0.69416(7) 0.02042(17) Uani 1 d . .
N3 N 0.79848(9) 0.28261(9) 0.97078(7) 0.01336(17) Uani 1 d . .
O2 O 0.21547(9) 0.36624(9) 0.77650(7) 0.02130(17) Uani 1 d . .
N1 N 0.34831(10) 0.41033(9) 0.74951(7) 0.01389(17) Uani 1 d . .
N2 N 0.56832(9) 0.33752(10) 0.59753(7) 0.01348(17) Uani 1 d . .
N4 N 1.00564(10) 0.19636(10) 1.09138(8) 0.01651(18) Uani 1 d . .
C2 C 0.56593(11) 0.33319(10) 0.72093(8) 0.01137(18) Uani 1 d . .
C12 C 0.76459(11) 0.26521(11) 0.48725(9) 0.01292(19) Uani 1 d . .
C3 C 0.67803(11) 0.30666(10) 0.78392(9) 0.01226(18) Uani 1 d . .
H3 H 0.7569 0.294 0.7404 0.015 Uiso 1 calc . .
C11 C 0.71598(11) 0.38759(10) 0.54979(9) 0.01268(19) Uani 1 d . .
H11A H 0.8008 0.464 0.6217 0.015 Uiso 1 calc . .
H11B H 0.7084 0.4395 0.4873 0.015 Uiso 1 calc . .
C19 C 0.39612(11) 0.12140(11) 0.40411(9) 0.01465(19) Uani 1 d . .
H19A H 0.2914 0.0785 0.3505 0.018 Uiso 1 calc . .
H19B H 0.3938 0.0481 0.4487 0.018 Uiso 1 calc . .
C5 C 0.55327(11) 0.30404(11) 0.96888(9) 0.01327(19) Uani 1 d . .
H5 H 0.5458 0.29 1.0502 0.016 Uiso 1 calc . .
C20 C 0.42433(11) 0.27023(11) 0.50368(9) 0.01440(19) Uani 1 d . .
H20A H 0.4285 0.3445 0.4596 0.017 Uiso 1 calc . .
H20B H 0.3341 0.2508 0.5486 0.017 Uiso 1 calc . .
C6 C 0.44205(11) 0.33039(10) 0.90912(9) 0.01280(19) Uani 1 d . .
H6 H 0.3579 0.334 0.9498 0.015 Uiso 1 calc . .
C10 C 0.94597(11) 0.29580(11) 1.16520(9) 0.0155(2) Uani 1 d . .
H10A H 1.0211 0.4032 1.1787 0.019 Uiso 1 calc . .
H10B H 0.9359 0.2802 1.2495 0.019 Uiso 1 calc . .
C13 C 0.67027(11) 0.14661(11) 0.37680(9) 0.01296(19) Uani 1 d . .
C9 C 0.78731(11) 0.26338(11) 1.09716(9) 0.01496(19) Uani 1 d . .
H9A H 0.7104 0.158 1.0886 0.018 Uiso 1 calc . .
H9B H 0.7499 0.3336 1.1479 0.018 Uiso 1 calc . .
C4 C 0.67901(11) 0.29791(10) 0.90882(9) 0.01174(18) Uani 1 d . .
C17 C 0.90656(12) 0.27342(12) 0.53665(9) 0.0172(2) Uani 1 d . .
H17 H 0.9716 0.355 0.6101 0.021 Uiso 1 calc . .
C8 C 1.03034(12) 0.23134(12) 0.97247(9) 0.0179(2) Uani 1 d . .
H8A H 1.0743 0.1675 0.9215 0.021 Uiso 1 calc . .
H8B H 1.1073 0.3393 0.9911 0.021 Uiso 1 calc . .
C14 C 0.72024(12) 0.03816(11) 0.32043(9) 0.0163(2) Uani 1 d . .
H14 H 0.6571 -0.0423 0.2457 0.02 Uiso 1 calc . .
C18 C 0.51807(11) 0.13550(11) 0.31700(9) 0.01386(19) Uani 1 d . .
H18A H 0.4717 0.046 0.2395 0.017 Uiso 1 calc . .
H18B H 0.5415 0.227 0.2904 0.017 Uiso 1 calc . .
C1 C 0.45067(11) 0.35185(10) 0.78980(9) 0.01197(19) Uani 1 d . .
C16 C 0.95438(12) 0.16356(13) 0.47966(10) 0.0208(2) Uani 1 d . .
H16 H 1.0507 0.1697 0.5148 0.025 Uiso 1 calc . .
C15 C 0.86089(13) 0.04549(12) 0.37161(10) 0.0197(2) Uani 1 d . .
H15 H 0.8924 -0.03 0.3326 0.024 Uiso 1 calc . .
C41 C 1.15265(12) 0.21836(14) 1.16019(10) 0.0222(2) Uani 1 d . .
H41A H 1.1896 0.1496 1.1085 0.033 Uiso 1 calc . .
H41B H 1.1352 0.1963 1.2407 0.033 Uiso 1 calc . .
H41C H 1.2317 0.3239 1.1776 0.033 Uiso 1 calc . .
C7 C 0.87816(12) 0.20298(13) 0.89627(9) 0.0200(2) Uani 1 d . .
H7A H 0.9007 0.2372 0.8205 0.024 Uiso 1 calc . .
H7B H 0.8075 0.0924 0.8664 0.024 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 N1 1.2368(11) . ?
N3 C4 1.3847(12) . ?
N3 C7 1.4658(12) . ?
N3 C9 1.4661(12) . ?
O2 N1 1.2371(11) . ?
N1 C1 1.4443(11) . ?
N2 C2 1.3799(11) . ?
N2 C20 1.4604(12) . ?
N2 C11 1.4632(11) . ?
N4 C10 1.4549(13) . ?
N4 C8 1.4569(12) . ?
N4 C41 1.4616(12) . ?
C2 C3 1.4021(12) . ?
C2 C1 1.4190(12) . ?
C12 C17 1.3951(13) . ?
C12 C13 1.4050(13) . ?
C12 C11 1.5214(13) . ?
C3 C4 1.4089(12) . ?
C3 H3 0.95 . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C19 C20 1.5310(13) . ?
C19 C18 1.5342(13) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C5 C6 1.3760(13) . ?
C5 C4 1.4175(13) . ?
C5 H5 0.95 . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
C6 C1 1.3954(13) . ?
C6 H6 0.95 . ?
C10 C9 1.5178(13) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C13 C14 1.3958(13) . ?
C13 C18 1.5115(13) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C17 C16 1.3952(14) . ?
C17 H17 0.95 . ?
C8 C7 1.5165(13) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C14 C15 1.3940(14) . ?
C14 H14 0.95 . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C16 C15 1.3850(16) . ?
C16 H16 0.95 . ?
C15 H15 0.95 . ?
C41 H41A 0.98 . ?
C41 H41B 0.98 . ?
C41 H41C 0.98 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N3 C7 119.35(8) . . ?
C4 N3 C9 118.50(7) . . ?
C7 N3 C9 113.55(8) . . ?
O1 N1 O2 122.35(8) . . ?
O1 N1 C1 118.91(8) . . ?
O2 N1 C1 118.67(8) . . ?
C2 N2 C20 121.87(8) . . ?
C2 N2 C11 120.80(7) . . ?
C20 N2 C11 116.61(7) . . ?
C10 N4 C8 107.69(8) . . ?
C10 N4 C41 111.33(8) . . ?
C8 N4 C41 110.10(8) . . ?
N2 C2 C3 120.68(8) . . ?
N2 C2 C1 122.81(8) . . ?
C3 C2 C1 116.50(8) . . ?
C17 C12 C13 119.49(9) . . ?
C17 C12 C11 120.02(9) . . ?
C13 C12 C11 120.44(8) . . ?
C2 C3 C4 123.01(8) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
N2 C11 C12 116.80(8) . . ?
N2 C11 H11A 108.1 . . ?
C12 C11 H11A 108.1 . . ?
N2 C11 H11B 108.1 . . ?
C12 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
C20 C19 C18 115.22(8) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C6 C5 C4 119.88(8) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N2 C20 C19 113.98(8) . . ?
N2 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
N2 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C5 C6 C1 121.16(8) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
N4 C10 C9 110.78(8) . . ?
N4 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C14 C13 C12 118.87(9) . . ?
C14 C13 C18 119.54(9) . . ?
C12 C13 C18 121.57(8) . . ?
N3 C9 C10 110.53(8) . . ?
N3 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N3 C4 C3 121.06(8) . . ?
N3 C4 C5 120.95(8) . . ?
C3 C4 C5 117.99(8) . . ?
C12 C17 C16 120.92(10) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
N4 C8 C7 111.28(8) . . ?
N4 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N4 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
C15 C14 C13 121.33(9) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C13 C18 C19 114.49(8) . . ?
C13 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
C13 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C6 C1 C2 121.00(8) . . ?
C6 C1 N1 115.66(8) . . ?
C2 C1 N1 122.96(8) . . ?
C15 C16 C17 119.75(9) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C15 C14 119.60(9) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N4 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
N4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N3 C7 C8 112.25(8) . . ?
N3 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N3 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?

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
C20 N2 C2 C3 140.18(9) . . . . ?
C11 N2 C2 C3 -29.70(13) . . . . ?
C20 N2 C2 C1 -38.55(13) . . . . ?
C11 N2 C2 C1 151.56(9) . . . . ?
N2 C2 C3 C4 -178.63(8) . . . . ?
C1 C2 C3 C4 0.18(13) . . . . ?
C2 N2 C11 C12 90.74(10) . . . . ?
C20 N2 C11 C12 -79.66(10) . . . . ?
C17 C12 C11 N2 -120.46(9) . . . . ?
C13 C12 C11 N2 62.02(11) . . . . ?
C2 N2 C20 C19 -106.22(10) . . . . ?
C11 N2 C20 C19 64.07(11) . . . . ?
C18 C19 C20 N2 -64.23(11) . . . . ?
C4 C5 C6 C1 -0.19(14) . . . . ?
C8 N4 C10 C9 63.55(10) . . . . ?
C41 N4 C10 C9 -175.67(8) . . . . ?
C17 C12 C13 C14 1.08(13) . . . . ?
C11 C12 C13 C14 178.62(8) . . . . ?
C17 C12 C13 C18 -177.96(8) . . . . ?
C11 C12 C13 C18 -0.42(13) . . . . ?
C4 N3 C9 C10 -163.03(8) . . . . ?
C7 N3 C9 C10 49.30(11) . . . . ?
N4 C10 C9 N3 -57.97(10) . . . . ?
C7 N3 C4 C3 -30.00(13) . . . . ?
C9 N3 C4 C3 -175.77(8) . . . . ?
C7 N3 C4 C5 149.49(9) . . . . ?
C9 N3 C4 C5 3.72(13) . . . . ?
C2 C3 C4 N3 -175.24(8) . . . . ?
C2 C3 C4 C5 5.26(14) . . . . ?
C6 C5 C4 N3 175.27(9) . . . . ?
C6 C5 C4 C3 -5.22(14) . . . . ?
C13 C12 C17 C16 -1.52(14) . . . . ?
C11 C12 C17 C16 -179.07(9) . . . . ?
C10 N4 C8 C7 -60.89(11) . . . . ?
C41 N4 C8 C7 177.55(9) . . . . ?
C12 C13 C14 C15 0.07(14) . . . . ?
C18 C13 C14 C15 179.13(8) . . . . ?
C14 C13 C18 C19 121.17(9) . . . . ?
C12 C13 C18 C19 -59.80(12) . . . . ?
C20 C19 C18 C13 78.37(10) . . . . ?
C5 C6 C1 C2 5.93(14) . . . . ?
C5 C6 C1 N1 -167.21(9) . . . . ?
N2 C2 C1 C6 172.98(9) . . . . ?
C3 C2 C1 C6 -5.80(13) . . . . ?
N2 C2 C1 N1 -14.38(14) . . . . ?
C3 C2 C1 N1 166.83(8) . . . . ?
O1 N1 C1 C6 139.49(9) . . . . ?
O2 N1 C1 C6 -37.46(12) . . . . ?
O1 N1 C1 C2 -33.51(13) . . . . ?
O2 N1 C1 C2 149.54(9) . . . . ?
C12 C17 C16 C15 0.79(15) . . . . ?
C17 C16 C15 C14 0.38(15) . . . . ?
C13 C14 C15 C16 -0.81(15) . . . . ?
C4 N3 C7 C8 165.18(8) . . . . ?
C9 N3 C7 C8 -47.45(12) . . . . ?
N4 C8 C7 N3 53.37(12) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
