# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_dan8113
_database_code_depnum_ccdc_archive 'CCDC 1470319'
_audit_update_record             
;
2017-01-31 deposited with the CCDC.
2017-02-07 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         367.44

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   8.5010(4)
_cell_length_b                   8.6149(4)
_cell_length_c                   13.9713(6)
_cell_angle_alpha                91.269(2)
_cell_angle_beta                 94.756(2)
_cell_angle_gamma                114.531(2)
_cell_volume                     925.82(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7830
_cell_measurement_theta_min      2.8318
_cell_measurement_theta_max      27.5791
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.181
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            16565
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             4057
_reflns_number_gt                3425
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1095
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         4057
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.3840P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.307
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.39629(13) 0.70184(13) 0.48484(7) 0.0123(2) Uani d . . . 1 . .
N N2 0.57258(13) 0.77591(14) 0.50369(7) 0.0128(2) Uani d . . . 1 . .
N N3 0.39960(14) 0.52757(14) 0.78128(7) 0.0137(2) Uani d . . . 1 . .
H H1 0.404(2) 0.634(2) 0.7852(12) 0.022(4) Uiso d . . . 1 . .
O O1 0.36998(14) 0.77580(13) 0.88310(7) 0.0220(2) Uani d . . . 1 . .
C C1 0.60536(16) 0.70197(16) 0.58168(8) 0.0120(3) Uani d . . . 1 . .
C C2 0.44870(16) 0.57883(16) 0.61273(9) 0.0123(3) Uani d . . . 1 . .
C C3 0.31987(16) 0.58416(16) 0.54915(9) 0.0133(3) Uani d . . . 1 . .
H H3 0.1986 0.5175 0.5498 0.016 Uiso calc U . R 1 . .
C C4 0.42098(17) 0.45529(16) 0.69026(9) 0.0139(3) Uani d . . . 1 . .
H H4A 0.3162 0.3489 0.6705 0.017 Uiso calc U . R 1 . .
H H4B 0.5218 0.4257 0.6992 0.017 Uiso calc U . R 1 . .
C C11 0.31318(16) 0.74567(16) 0.40392(9) 0.0124(3) Uani d . . . 1 . .
C C12 0.14353(17) 0.63630(17) 0.36921(9) 0.0166(3) Uani d . . . 1 . .
H H12 0.0844 0.5318 0.3983 0.02 Uiso calc U . R 1 . .
C C13 0.06157(17) 0.68144(18) 0.29170(10) 0.0187(3) Uani d . . . 1 . .
H H13 -0.0548 0.6081 0.2684 0.022 Uiso calc U . R 1 . .
C C14 0.14793(18) 0.83271(18) 0.24786(9) 0.0182(3) Uani d . . . 1 . .
H H14 0.0904 0.864 0.1957 0.022 Uiso calc U . R 1 . .
C C15 0.31909(18) 0.93784(17) 0.28094(9) 0.0181(3) Uani d . . . 1 . .
H H15 0.38 1.0393 0.2496 0.022 Uiso calc U . R 1 . .
C C16 0.40242(17) 0.89603(17) 0.35949(9) 0.0155(3) Uani d . . . 1 . .
H H16 0.519 0.9693 0.3825 0.019 Uiso calc U . R 1 . .
C C21 0.78580(16) 0.74896(16) 0.62157(9) 0.0128(3) Uani d . . . 1 . .
C C22 0.92130(17) 0.81461(16) 0.56241(9) 0.0147(3) Uani d . . . 1 . .
H H22 0.8956 0.8285 0.4965 0.018 Uiso calc U . R 1 . .
C C23 1.09197(17) 0.85941(17) 0.59885(10) 0.0171(3) Uani d . . . 1 . .
H H23 1.1826 0.9051 0.5581 0.021 Uiso calc U . R 1 . .
C C24 1.13143(17) 0.83759(17) 0.69529(10) 0.0176(3) Uani d . . . 1 . .
H H24 1.2483 0.8668 0.7201 0.021 Uiso calc U . R 1 . .
C C25 0.99814(17) 0.77278(17) 0.75467(9) 0.0170(3) Uani d . . . 1 . .
H H25 1.0242 0.7576 0.8203 0.02 Uiso calc U . R 1 . .
C C26 0.82738(17) 0.73018(17) 0.71862(9) 0.0153(3) Uani d . . . 1 . .
H H26 0.7376 0.6878 0.7601 0.018 Uiso calc U . R 1 . .
C C31 0.34081(15) 0.43079(16) 0.85761(9) 0.0128(3) Uani d . . . 1 . .
C C32 0.30048(16) 0.50025(17) 0.94129(9) 0.0145(3) Uani d . . . 1 . .
C C33 0.23795(18) 0.39232(18) 1.01673(9) 0.0194(3) Uani d . . . 1 . .
H H33 0.2108 0.4373 1.0726 0.023 Uiso calc U . R 1 . .
C C34 0.21454(19) 0.22399(19) 1.01273(10) 0.0239(3) Uani d . . . 1 . .
H H34 0.1716 0.1542 1.0647 0.029 Uiso calc U . R 1 . .
C C35 0.25506(19) 0.15807(18) 0.93098(10) 0.0223(3) Uani d . . . 1 . .
H H35 0.2396 0.0423 0.9274 0.027 Uiso calc U . R 1 . .
C C36 0.31729(17) 0.25862(17) 0.85517(9) 0.0174(3) Uani d . . . 1 . .
H H36 0.3448 0.2111 0.8004 0.021 Uiso calc U . R 1 . .
C C37 0.32146(17) 0.67875(18) 0.94909(9) 0.0177(3) Uani d . . . 1 . .
C C38 0.2798(2) 0.7469(2) 1.03982(10) 0.0267(3) Uani d . . . 1 . .
H H38A 0.326 0.8718 1.0404 0.04 Uiso calc U . R 1 . .
H H38B 0.333 0.7142 1.0962 0.04 Uiso calc U . R 1 . .
H H38C 0.1536 0.6989 1.0416 0.04 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 . 1.3592(16) ?
N1 N2 . 1.3622(14) ?
N1 C11 . 1.4240(16) ?
N2 C1 . 1.3411(16) ?
N3 C31 . 1.3653(16) ?
N3 C4 . 1.4612(15) ?
N3 H1 . 0.899(18) ?
O1 C37 . 1.2370(16) ?
C1 C2 . 1.4249(17) ?
C1 C21 . 1.4697(17) ?
C2 C3 . 1.3685(18) ?
C2 C4 . 1.4989(17) ?
C3 H3 . 0.95 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C11 C16 . 1.3916(18) ?
C11 C12 . 1.3922(18) ?
C12 C13 . 1.3884(19) ?
C12 H12 . 0.95 ?
C13 C14 . 1.389(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.3881(19) ?
C14 H14 . 0.95 ?
C15 C16 . 1.3915(18) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C21 C26 . 1.4026(17) ?
C21 C22 . 1.4027(17) ?
C22 C23 . 1.3846(18) ?
C22 H22 . 0.95 ?
C23 C24 . 1.3972(18) ?
C23 H23 . 0.95 ?
C24 C25 . 1.3910(19) ?
C24 H24 . 0.95 ?
C25 C26 . 1.3871(18) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?
C31 C36 . 1.4113(18) ?
C31 C32 . 1.4312(18) ?
C32 C33 . 1.4085(18) ?
C32 C37 . 1.4731(19) ?
C33 C34 . 1.379(2) ?
C33 H33 . 0.95 ?
C34 C35 . 1.394(2) ?
C34 H34 . 0.95 ?
C35 C36 . 1.3802(19) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?
C37 C38 . 1.5135(18) ?
C38 H38A . 0.98 ?
C38 H38B . 0.98 ?
C38 H38C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 N1 N2 . . 111.72(10) ?
C3 N1 C11 . . 127.43(11) ?
N2 N1 C11 . . 120.82(10) ?
C1 N2 N1 . . 104.83(10) ?
C31 N3 C4 . . 122.49(11) ?
C31 N3 H1 . . 116.1(10) ?
C4 N3 H1 . . 120.2(11) ?
N2 C1 C2 . . 111.16(11) ?
N2 C1 C21 . . 119.90(11) ?
C2 C1 C21 . . 128.92(11) ?
C3 C2 C1 . . 104.48(11) ?
C3 C2 C4 . . 124.89(11) ?
C1 C2 C4 . . 130.40(11) ?
N1 C3 C2 . . 107.81(11) ?
N1 C3 H3 . . 126.1 ?
C2 C3 H3 . . 126.1 ?
N3 C4 C2 . . 111.27(10) ?
N3 C4 H4A . . 109.4 ?
C2 C4 H4A . . 109.4 ?
N3 C4 H4B . . 109.4 ?
C2 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C16 C11 C12 . . 120.52(12) ?
C16 C11 N1 . . 119.92(11) ?
C12 C11 N1 . . 119.56(11) ?
C13 C12 C11 . . 119.37(12) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.69(12) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C15 C14 C13 . . 119.42(12) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 120.66(12) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 119.28(12) ?
C15 C16 H16 . . 120.4 ?
C11 C16 H16 . . 120.4 ?
C26 C21 C22 . . 118.41(12) ?
C26 C21 C1 . . 121.50(11) ?
C22 C21 C1 . . 120.09(11) ?
C23 C22 C21 . . 120.81(12) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C22 C23 C24 . . 120.23(12) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?
C25 C24 C23 . . 119.45(12) ?
C25 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
C26 C25 C24 . . 120.38(12) ?
C26 C25 H25 . . 119.8 ?
C24 C25 H25 . . 119.8 ?
C25 C26 C21 . . 120.69(12) ?
C25 C26 H26 . . 119.7 ?
C21 C26 H26 . . 119.7 ?
N3 C31 C36 . . 120.37(11) ?
N3 C31 C32 . . 121.16(12) ?
C36 C31 C32 . . 118.47(11) ?
C33 C32 C31 . . 118.10(12) ?
C33 C32 C37 . . 120.27(12) ?
C31 C32 C37 . . 121.63(11) ?
C34 C33 C32 . . 122.59(13) ?
C34 C33 H33 . . 118.7 ?
C32 C33 H33 . . 118.7 ?
C33 C34 C35 . . 118.75(12) ?
C33 C34 H34 . . 120.6 ?
C35 C34 H34 . . 120.6 ?
C36 C35 C34 . . 120.95(13) ?
C36 C35 H35 . . 119.5 ?
C34 C35 H35 . . 119.5 ?
C35 C36 C31 . . 121.13(12) ?
C35 C36 H36 . . 119.4 ?
C31 C36 H36 . . 119.4 ?
O1 C37 C32 . . 122.27(12) ?
O1 C37 C38 . . 118.15(13) ?
C32 C37 C38 . . 119.57(12) ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 N2 C1 . . . . -0.07(13) ?
C11 N1 N2 C1 . . . . -178.04(10) ?
N1 N2 C1 C2 . . . . 0.31(13) ?
N1 N2 C1 C21 . . . . 178.58(10) ?
N2 C1 C2 C3 . . . . -0.43(14) ?
C21 C1 C2 C3 . . . . -178.51(12) ?
N2 C1 C2 C4 . . . . 174.22(12) ?
C21 C1 C2 C4 . . . . -3.9(2) ?
N2 N1 C3 C2 . . . . -0.20(14) ?
C11 N1 C3 C2 . . . . 177.60(11) ?
C1 C2 C3 N1 . . . . 0.37(14) ?
C4 C2 C3 N1 . . . . -174.66(11) ?
C31 N3 C4 C2 . . . . 167.44(11) ?
C3 C2 C4 N3 . . . . -93.27(14) ?
C1 C2 C4 N3 . . . . 93.05(15) ?
C3 N1 C11 C16 . . . . 164.00(12) ?
N2 N1 C11 C16 . . . . -18.37(17) ?
C3 N1 C11 C12 . . . . -16.74(19) ?
N2 N1 C11 C12 . . . . 160.88(11) ?
C16 C11 C12 C13 . . . . -2.24(19) ?
N1 C11 C12 C13 . . . . 178.50(11) ?
C11 C12 C13 C14 . . . . 1.0(2) ?
C12 C13 C14 C15 . . . . 1.3(2) ?
C13 C14 C15 C16 . . . . -2.3(2) ?
C14 C15 C16 C11 . . . . 1.0(2) ?
C12 C11 C16 C15 . . . . 1.24(19) ?
N1 C11 C16 C15 . . . . -179.51(11) ?
N2 C1 C21 C26 . . . . 155.09(12) ?
C2 C1 C21 C26 . . . . -27.0(2) ?
N2 C1 C21 C22 . . . . -24.78(18) ?
C2 C1 C21 C22 . . . . 153.16(13) ?
C26 C21 C22 C23 . . . . 0.16(19) ?
C1 C21 C22 C23 . . . . -179.97(12) ?
C21 C22 C23 C24 . . . . 0.8(2) ?
C22 C23 C24 C25 . . . . -0.9(2) ?
C23 C24 C25 C26 . . . . -0.1(2) ?
C24 C25 C26 C21 . . . . 1.1(2) ?
C22 C21 C26 C25 . . . . -1.11(19) ?
C1 C21 C26 C25 . . . . 179.02(12) ?
C4 N3 C31 C36 . . . . 7.48(18) ?
C4 N3 C31 C32 . . . . -172.06(11) ?
N3 C31 C32 C33 . . . . 179.06(11) ?
C36 C31 C32 C33 . . . . -0.48(18) ?
N3 C31 C32 C37 . . . . -0.38(18) ?
C36 C31 C32 C37 . . . . -179.93(11) ?
C31 C32 C33 C34 . . . . 0.0(2) ?
C37 C32 C33 C34 . . . . 179.44(13) ?
C32 C33 C34 C35 . . . . 0.3(2) ?
C33 C34 C35 C36 . . . . -0.1(2) ?
C34 C35 C36 C31 . . . . -0.4(2) ?
N3 C31 C36 C35 . . . . -178.84(12) ?
C32 C31 C36 C35 . . . . 0.71(19) ?
C33 C32 C37 O1 . . . . -177.34(13) ?
C31 C32 C37 O1 . . . . 2.1(2) ?
C33 C32 C37 C38 . . . . 1.59(19) ?
C31 C32 C37 C38 . . . . -178.99(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H1 O1 . 0.899(18) 1.934(17) 2.6518(15) 135.6(14) ?

####################################################################### 
# 
# 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_dan8187
_database_code_depnum_ccdc_archive 'CCDC 1470320'
_audit_update_record             
;
2017-01-31 deposited with the CCDC.
2017-02-07 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Cl N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         260.71

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.5288(10)
_cell_length_b                   5.2501(4)
_cell_length_c                   17.6225(12)
_cell_angle_alpha                90
_cell_angle_beta                 113.257(4)
_cell_angle_gamma                90
_cell_volume                     1234.98(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3649
_cell_measurement_theta_min      5.0585
_cell_measurement_theta_max      66.9295
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.032
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

_exptl_absorpt_coefficient_mu    2.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            9359
_diffrn_reflns_av_R_equivalents  0.1326
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         64.37
_diffrn_reflns_theta_full        64.37
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_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_number_total             2017
_reflns_number_gt                1686
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2002
_refine_ls_R_factor_gt           0.1800
_refine_ls_wR_factor_gt          0.3342
_refine_ls_wR_factor_ref         0.3428
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_restrained_S_all      1.327
_refine_ls_number_reflns         2017
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+30.4509P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.545
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)

;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.8078(2) 1.2408(6) 0.52668(18) 0.0238(7) Uani d . . . 1 . .
N N1 0.5614(8) 0.3197(18) 0.2971(6) 0.020(2) Uani d . . D 1 . .
H H1 0.537(9) 0.30(3) 0.334(6) 0.03 Uiso d U . D 1 . .
N N2 0.5852(7) 0.600(2) 0.4288(6) 0.019(2) Uani d . . . 1 . .
O O1 0.4208(6) 0.0808(16) 0.3293(5) 0.022(2) Uani d . . . 1 . .
C C1 0.5420(9) 0.152(2) 0.2360(7) 0.021(3) Uani d . . . 1 . .
C C2 0.4683(8) -0.043(3) 0.2190(7) 0.021(3) Uani d . . . 1 . .
C C3 0.4490(9) -0.210(2) 0.1552(8) 0.025(3) Uani d . . . 1 . .
H H3 0.3994 -0.3381 0.1458 0.03 Uiso calc U . R 1 . .
C C4 0.5009(9) -0.196(2) 0.1037(7) 0.020(3) Uani d . . . 1 . .
H H4 0.4863 -0.3111 0.0589 0.024 Uiso calc U . R 1 . .
C C5 0.5734(9) -0.014(3) 0.1184(8) 0.024(3) Uani d . . . 1 . .
H H5 0.6096 -0.0055 0.0839 0.029 Uiso calc U . R 1 . .
C C6 0.5947(9) 0.157(3) 0.1816(8) 0.027(3) Uani d . . . 1 . .
H H6 0.6452 0.2813 0.1899 0.032 Uiso calc U . R 1 . .
C C7 0.6419(9) 0.504(3) 0.3192(7) 0.020(3) Uani d . . . 1 . .
H H7A 0.6307 0.618 0.2715 0.024 Uiso calc U . R 1 . .
H H7B 0.7062 0.4143 0.3322 0.024 Uiso calc U . R 1 . .
C C8 0.6485(8) 0.664(2) 0.3931(7) 0.015(2) Uani d . . . 1 . .
C C9 0.7159(9) 0.859(2) 0.4198(7) 0.018(3) Uani d . . . 1 . .
H H9 0.7584 0.8973 0.3919 0.022 Uiso calc U . R 1 . .
C C10 0.7214(8) 0.998(2) 0.4867(7) 0.019(3) Uani d . . . 1 . .
C C11 0.6541(10) 0.939(2) 0.5249(8) 0.025(3) Uani d . . . 1 . .
H H11 0.6535 1.0367 0.5701 0.03 Uiso calc U . R 1 . .
C C12 0.5896(9) 0.736(3) 0.4939(7) 0.027(3) Uani d . . . 1 . .
H H12 0.5462 0.6913 0.5204 0.033 Uiso calc U . R 1 . .
C C13 0.4109(9) -0.071(2) 0.2748(8) 0.026(3) Uani d . . . 1 . .
C C14 0.3374(9) -0.283(3) 0.2575(7) 0.030(3) Uani d . . . 1 . .
H H14A 0.3059 -0.2785 0.2974 0.045 Uiso calc U . R 1 . .
H H14B 0.372 -0.4465 0.262 0.045 Uiso calc U . R 1 . .
H H14C 0.2858 -0.2648 0.2015 0.045 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C10 . 1.733(12) ?
N1 C1 . 1.333(15) ?
N1 C7 . 1.450(15) ?
N1 H1 . 0.86(2) ?
N2 C12 . 1.332(16) ?
N2 C8 . 1.346(14) ?
O1 C13 . 1.213(15) ?
C1 C2 . 1.425(17) ?
C1 C6 . 1.445(17) ?
C2 C3 . 1.364(18) ?
C2 C13 . 1.527(18) ?
C3 C4 . 1.392(16) ?
C3 H3 . 0.95 ?
C4 C5 . 1.370(17) ?
C4 H4 . 0.95 ?
C5 C6 . 1.364(18) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C8 . 1.518(16) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.366(16) ?
C9 C10 . 1.361(17) ?
C9 H9 . 0.95 ?
C10 C11 . 1.422(17) ?
C11 C12 . 1.382(18) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 C14 . 1.490(18) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C7 . . 123.4(10) ?
C1 N1 H1 . . 121.(10) ?
C7 N1 H1 . . 114.(9) ?
C12 N2 C8 . . 117.3(11) ?
N1 C1 C2 . . 123.2(11) ?
N1 C1 C6 . . 121.7(12) ?
C2 C1 C6 . . 115.1(11) ?
C3 C2 C1 . . 121.9(12) ?
C3 C2 C13 . . 118.9(11) ?
C1 C2 C13 . . 119.2(11) ?
C2 C3 C4 . . 120.9(12) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C5 C4 C3 . . 119.3(11) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C6 C5 C4 . . 121.5(12) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C1 . . 121.3(12) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
N1 C7 C8 . . 111.7(9) ?
N1 C7 H7A . . 109.3 ?
C8 C7 H7A . . 109.3 ?
N1 C7 H7B . . 109.3 ?
C8 C7 H7B . . 109.3 ?
H7A C7 H7B . . 107.9 ?
N2 C8 C9 . . 123.7(11) ?
N2 C8 C7 . . 116.1(10) ?
C9 C8 C7 . . 120.1(10) ?
C10 C9 C8 . . 119.3(11) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C9 C10 C11 . . 118.6(11) ?
C9 C10 Cl1 . . 122.2(10) ?
C11 C10 Cl1 . . 119.2(9) ?
C12 C11 C10 . . 117.7(11) ?
C12 C11 H11 . . 121.2 ?
C10 C11 H11 . . 121.2 ?
N2 C12 C11 . . 123.4(11) ?
N2 C12 H12 . . 118.3 ?
C11 C12 H12 . . 118.3 ?
O1 C13 C14 . . 120.3(12) ?
O1 C13 C2 . . 121.6(12) ?
C14 C13 C2 . . 118.0(11) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . 174.5(12) ?
C7 N1 C1 C6 . . . . -5.9(18) ?
N1 C1 C2 C3 . . . . 179.0(12) ?
C6 C1 C2 C3 . . . . -0.6(18) ?
N1 C1 C2 C13 . . . . -2.6(18) ?
C6 C1 C2 C13 . . . . 177.9(11) ?
C1 C2 C3 C4 . . . . -0.1(19) ?
C13 C2 C3 C4 . . . . -178.6(11) ?
C2 C3 C4 C5 . . . . 1.0(19) ?
C3 C4 C5 C6 . . . . -1.(2) ?
C4 C5 C6 C1 . . . . 0.(2) ?
N1 C1 C6 C5 . . . . -179.0(12) ?
C2 C1 C6 C5 . . . . 0.6(18) ?
C1 N1 C7 C8 . . . . -177.8(10) ?
C12 N2 C8 C9 . . . . -0.2(18) ?
C12 N2 C8 C7 . . . . 179.8(11) ?
N1 C7 C8 N2 . . . . 4.1(15) ?
N1 C7 C8 C9 . . . . -175.9(10) ?
N2 C8 C9 C10 . . . . 0.7(18) ?
C7 C8 C9 C10 . . . . -179.3(11) ?
C8 C9 C10 C11 . . . . -2.1(17) ?
C8 C9 C10 Cl1 . . . . 177.7(9) ?
C9 C10 C11 C12 . . . . 2.9(18) ?
Cl1 C10 C11 C12 . . . . -176.9(10) ?
C8 N2 C12 C11 . . . . 1.1(19) ?
C10 C11 C12 N2 . . . . -2.(2) ?
C3 C2 C13 O1 . . . . -175.6(12) ?
C1 C2 C13 O1 . . . . 5.9(18) ?
C3 C2 C13 C14 . . . . 1.0(17) ?
C1 C2 C13 C14 . . . . -177.6(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . 0.86(2) 2.20(13) 2.652(13) 113.(11) ?
N1 H1 O1 . 0.86(2) 2.02(11) 2.642(13) 129.(12) ?
C11 H11 O1 3_666 0.95 2.49 3.163(15) 127.9 ?

