# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1511753'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H24 Cl2 Co N4 O4'
_chemical_formula_sum            'C36 H24 Cl2 Co N4 O4'
_chemical_formula_weight         706.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3935(4)
_cell_length_b                   9.1136(6)
_cell_length_c                   12.1362(7)
_cell_angle_alpha                90.411(2)
_cell_angle_beta                 104.798(2)
_cell_angle_gamma                111.102(2)
_cell_volume                     733.14(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.93
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0481 before and 0.0391 after correction.
The Ratio of minimum to maximum transmission is 0.8683.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             361
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5391
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.746
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2365
_reflns_number_total             3362
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.5300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.0000 0.5000 1.0000 0.01504(16) Uani 1 2 d S T P . .
Cl1 Cl 1.10806(11) 0.42595(9) 0.84578(6) 0.01987(19) Uani 1 1 d . . . . .
O1 O 0.6892(3) 0.3899(2) 0.88722(17) 0.0179(5) Uani 1 1 d . . . . .
O2 O 0.4652(3) 0.7528(3) 0.70762(18) 0.0219(5) Uani 1 1 d . . . . .
N1 N 1.0302(4) 0.7253(3) 0.9310(2) 0.0167(5) Uani 1 1 d . . . . .
N2 N 0.5736(4) 0.5691(3) 0.7971(2) 0.0150(5) Uani 1 1 d . . . . .
C1 C 1.2162(5) 0.8141(4) 0.9253(2) 0.0184(6) Uani 1 1 d . . . . .
H1 H 1.3187 0.7717 0.9466 0.022 Uiso 1 1 calc R . . . .
C2 C 1.2667(5) 0.9643(4) 0.8900(3) 0.0209(7) Uani 1 1 d . . . . .
H2 H 1.4009 1.0234 0.8880 0.025 Uiso 1 1 calc R . . . .
C3 C 1.1186(5) 1.0270(4) 0.8578(2) 0.0204(7) Uani 1 1 d . . . . .
H3 H 1.1486 1.1297 0.8334 0.025 Uiso 1 1 calc R . . . .
C4 C 0.9259(5) 0.9361(4) 0.8621(2) 0.0193(7) Uani 1 1 d . . . . .
H4 H 0.8209 0.9757 0.8398 0.023 Uiso 1 1 calc R . . . .
C5 C 0.8859(4) 0.7864(4) 0.8993(2) 0.0157(6) Uani 1 1 d . . . . .
C6 C 0.6756(4) 0.6833(4) 0.9010(2) 0.0170(6) Uani 1 1 d . . . . .
H6A H 0.6819 0.6255 0.9698 0.020 Uiso 1 1 calc R . . . .
H6B H 0.5974 0.7503 0.9055 0.020 Uiso 1 1 calc R . . . .
C7 C 0.5875(4) 0.4224(4) 0.7998(2) 0.0160(6) Uani 1 1 d . . . . .
C8 C 0.4771(4) 0.3084(4) 0.6977(2) 0.0158(6) Uani 1 1 d . . . . .
C9 C 0.4947(5) 0.1629(4) 0.6936(3) 0.0197(7) Uani 1 1 d . . . . .
H9 H 0.5816 0.1382 0.7565 0.024 Uiso 1 1 calc R . . . .
C10 C 0.3848(5) 0.0506(4) 0.5968(3) 0.0238(7) Uani 1 1 d . . . . .
H10 H 0.3961 -0.0499 0.5952 0.029 Uiso 1 1 calc R . . . .
C11 C 0.2615(5) 0.0861(4) 0.5048(3) 0.0227(7) Uani 1 1 d . . . . .
H11 H 0.1854 0.0087 0.4407 0.027 Uiso 1 1 calc R . . . .
C12 C 0.2459(5) 0.2364(4) 0.5040(3) 0.0186(7) Uani 1 1 d . . . . .
C13 C 0.1293(5) 0.2813(4) 0.4077(3) 0.0211(7) Uani 1 1 d . . . . .
H13 H 0.0508 0.2060 0.3426 0.025 Uiso 1 1 calc R . . . .
C14 C 0.1285(5) 0.4310(4) 0.4072(3) 0.0211(7) Uani 1 1 d . . . . .
H14 H 0.0523 0.4597 0.3414 0.025 Uiso 1 1 calc R . . . .
C15 C 0.2399(4) 0.5423(4) 0.5036(2) 0.0186(7) Uani 1 1 d . . . . .
H15 H 0.2405 0.6466 0.5025 0.022 Uiso 1 1 calc R . . . .
C16 C 0.3487(4) 0.5010(4) 0.6004(2) 0.0163(6) Uani 1 1 d . . . . .
C17 C 0.4622(4) 0.6187(4) 0.7018(2) 0.0172(6) Uani 1 1 d . . . . .
C18 C 0.3556(4) 0.3487(4) 0.6013(2) 0.0162(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 Cl1 2.3940(7) . ?
Co1 Cl1 2.3940(7) 2_767 ?
Co1 O1 2.208(2) 2_767 ?
Co1 O1 2.208(2) . ?
Co1 N1 2.181(2) . ?
Co1 N1 2.181(2) 2_767 ?
O1 C7 1.239(3) . ?
O2 C17 1.215(4) . ?
N1 C1 1.341(4) . ?
N1 C5 1.348(4) . ?
N2 C6 1.474(4) . ?
N2 C7 1.378(4) . ?
N2 C17 1.418(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(4) . ?
C5 C6 1.505(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.462(4) . ?
C8 C9 1.380(4) . ?
C8 C18 1.421(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.408(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.371(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.415(4) . ?
C12 C13 1.422(4) . ?
C12 C18 1.413(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.367(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.402(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(4) . ?
C16 C17 1.475(4) . ?
C16 C18 1.407(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Co1 Cl1 180.00(3) . 2_767 ?
O1 Co1 Cl1 86.81(6) 2_767 2_767 ?
O1 Co1 Cl1 93.19(6) . 2_767 ?
O1 Co1 Cl1 93.19(6) 2_767 . ?
O1 Co1 Cl1 86.81(6) . . ?
O1 Co1 O1 180.00(11) 2_767 . ?
N1 Co1 Cl1 88.64(7) . . ?
N1 Co1 Cl1 91.36(7) 2_767 . ?
N1 Co1 Cl1 88.64(7) 2_767 2_767 ?
N1 Co1 Cl1 91.36(7) . 2_767 ?
N1 Co1 O1 89.42(8) 2_767 . ?
N1 Co1 O1 89.42(8) . 2_767 ?
N1 Co1 O1 90.58(8) . . ?
N1 Co1 O1 90.58(8) 2_767 2_767 ?
N1 Co1 N1 180.0 . 2_767 ?
C7 O1 Co1 135.9(2) . . ?
C1 N1 Co1 115.27(19) . . ?
C1 N1 C5 117.6(3) . . ?
C5 N1 Co1 127.1(2) . . ?
C7 N2 C6 118.7(2) . . ?
C7 N2 C17 124.8(3) . . ?
C17 N2 C6 116.5(2) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.4(3) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 122.0(3) . . ?
N1 C5 C6 117.2(3) . . ?
C4 C5 C6 120.8(3) . . ?
N2 C6 C5 110.6(2) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O1 C7 N2 120.2(3) . . ?
O1 C7 C8 122.1(3) . . ?
N2 C7 C8 117.7(2) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 C18 119.8(3) . . ?
C18 C8 C7 120.1(3) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.5(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 122.7(3) . . ?
C18 C12 C11 118.8(3) . . ?
C18 C12 C13 118.4(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 C18 120.2(3) . . ?
C18 C16 C17 120.1(3) . . ?
O2 C17 N2 119.3(3) . . ?
O2 C17 C16 124.1(3) . . ?
N2 C17 C16 116.6(3) . . ?
C12 C18 C8 119.6(3) . . ?
C16 C18 C8 120.6(3) . . ?
C16 C18 C12 119.8(3) . . ?

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
Co1 O1 C7 N2 -51.8(4) . . . . ?
Co1 O1 C7 C8 129.0(3) . . . . ?
Co1 N1 C1 C2 -176.2(2) . . . . ?
Co1 N1 C5 C4 176.4(2) . . . . ?
Co1 N1 C5 C6 -6.0(4) . . . . ?
O1 C7 C8 C9 -4.4(5) . . . . ?
O1 C7 C8 C18 177.3(3) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
N1 C5 C6 N2 -80.5(3) . . . . ?
N2 C7 C8 C9 176.5(3) . . . . ?
N2 C7 C8 C18 -1.9(4) . . . . ?
C1 N1 C5 C4 -0.2(4) . . . . ?
C1 N1 C5 C6 177.4(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 N1 -0.5(4) . . . . ?
C3 C4 C5 C6 -178.0(3) . . . . ?
C4 C5 C6 N2 97.2(3) . . . . ?
C5 N1 C1 C2 0.8(4) . . . . ?
C6 N2 C7 O1 -2.1(4) . . . . ?
C6 N2 C7 C8 177.1(2) . . . . ?
C6 N2 C17 O2 4.1(4) . . . . ?
C6 N2 C17 C16 -176.0(2) . . . . ?
C7 N2 C6 C5 91.5(3) . . . . ?
C7 N2 C17 O2 -177.8(3) . . . . ?
C7 N2 C17 C16 2.1(4) . . . . ?
C7 C8 C9 C10 178.3(3) . . . . ?
C7 C8 C18 C12 -178.6(3) . . . . ?
C7 C8 C18 C16 3.5(4) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C9 C8 C18 C12 3.1(4) . . . . ?
C9 C8 C18 C16 -174.9(3) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C10 C11 C12 C13 176.1(3) . . . . ?
C10 C11 C12 C18 -1.8(5) . . . . ?
C11 C12 C13 C14 -175.6(3) . . . . ?
C11 C12 C18 C8 -0.6(4) . . . . ?
C11 C12 C18 C16 177.4(3) . . . . ?
C12 C13 C14 C15 -1.5(5) . . . . ?
C13 C12 C18 C8 -178.5(3) . . . . ?
C13 C12 C18 C16 -0.5(4) . . . . ?
C13 C14 C15 C16 -1.0(5) . . . . ?
C14 C15 C16 C17 -179.0(3) . . . . ?
C14 C15 C16 C18 2.7(4) . . . . ?
C15 C16 C17 O2 1.2(5) . . . . ?
C15 C16 C17 N2 -178.8(3) . . . . ?
C15 C16 C18 C8 176.1(3) . . . . ?
C15 C16 C18 C12 -1.9(4) . . . . ?
C17 N2 C6 C5 -90.3(3) . . . . ?
C17 N2 C7 O1 179.8(3) . . . . ?
C17 N2 C7 C8 -1.0(4) . . . . ?
C17 C16 C18 C8 -2.3(4) . . . . ?
C17 C16 C18 C12 179.8(3) . . . . ?
C18 C8 C9 C10 -3.3(5) . . . . ?
C18 C12 C13 C14 2.3(4) . . . . ?
C18 C16 C17 O2 179.5(3) . . . . ?
C18 C16 C17 N2 -0.4(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1511755'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H22 Cl2 Co N6 O8'
_chemical_formula_sum            'C36 H22 Cl2 Co N6 O8'
_chemical_formula_weight         796.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1182(4)
_cell_length_b                   23.7237(13)
_cell_length_c                   7.2314(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.296(4)
_cell_angle_gamma                90
_cell_volume                     1522.35(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2286
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.829
_cell_measurement_theta_min      4.984
_shelx_estimated_absorpt_T_max   0.777
_shelx_estimated_absorpt_T_min   0.653
_exptl_absorpt_coefficient_mu    6.648
_exptl_absorpt_correction_T_max  0.3825
_exptl_absorpt_correction_T_min  0.2517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0857 before and 0.0697 after correction.
The Ratio of minimum to maximum transmission is 0.6580.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             810
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13787
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.259
_diffrn_reflns_theta_min         3.726
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2277
_reflns_number_total             2785
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0792
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1380P)²+3.3170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2224
_refine_ls_wR_factor_ref         0.2319
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.5000 0.5000 0.5000 0.0334(4) Uani 1 2 d S T P . .
Cl1 Cl 0.64366(15) 0.46022(6) 0.7806(2) 0.0405(4) Uani 1 1 d . . . . .
O1 O 0.5174(4) 0.41451(16) 0.3766(6) 0.0329(9) Uani 1 1 d . . . . .
O2 O 0.1011(4) 0.30601(19) 0.3261(7) 0.0481(11) Uani 1 1 d . . . . .
O3 O 0.8102(5) 0.1323(2) 0.6188(7) 0.0493(11) Uani 1 1 d . . . . .
O4 O 0.9307(6) 0.1672(2) 0.4183(8) 0.0581(13) Uani 1 1 d . . . . .
N1 N 0.2917(5) 0.47337(19) 0.5802(7) 0.0303(10) Uani 1 1 d . . . . .
N2 N 0.3089(4) 0.35944(18) 0.3480(6) 0.0262(9) Uani 1 1 d . . . . .
N3 N 0.8309(6) 0.1694(2) 0.5075(8) 0.0445(13) Uani 1 1 d . . . . .
C1 C 0.2681(6) 0.4960(2) 0.7398(9) 0.0336(12) Uani 1 1 d . . . . .
H1 H 0.3421 0.5208 0.8105 0.040 Uiso 1 1 calc R . . . .
C2 C 0.1397(6) 0.4850(2) 0.8073(9) 0.0335(12) Uani 1 1 d . . . . .
H2 H 0.1265 0.5019 0.9215 0.040 Uiso 1 1 calc R . . . .
C3 C 0.0337(6) 0.4495(3) 0.7065(9) 0.0397(14) Uani 1 1 d . . . . .
H3 H -0.0558 0.4419 0.7481 0.048 Uiso 1 1 calc R . . . .
C4 C 0.0575(6) 0.4247(3) 0.5433(9) 0.0353(12) Uani 1 1 d . . . . .
H4 H -0.0143 0.3991 0.4734 0.042 Uiso 1 1 calc R . . . .
C5 C 0.1869(5) 0.4376(2) 0.4824(8) 0.0280(11) Uani 1 1 d . . . . .
C6 C 0.2135(5) 0.4110(2) 0.3053(8) 0.0300(11) Uani 1 1 d . . . . .
H6A H 0.1154 0.4008 0.2208 0.036 Uiso 1 1 calc R . . . .
H6B H 0.2635 0.4385 0.2373 0.036 Uiso 1 1 calc R . . . .
C7 C 0.2370(6) 0.3080(2) 0.3502(8) 0.0335(12) Uani 1 1 d . . . . .
C8 C 0.3328(6) 0.2568(2) 0.3786(8) 0.0330(12) Uani 1 1 d . . . . .
C9 C 0.2627(7) 0.2051(3) 0.3676(9) 0.0383(13) Uani 1 1 d . . . . .
H9 H 0.1560 0.2027 0.3434 0.046 Uiso 1 1 calc R . . . .
C10 C 0.3498(8) 0.1565(3) 0.3922(9) 0.0452(15) Uani 1 1 d . . . . .
H10 H 0.3015 0.1208 0.3815 0.054 Uiso 1 1 calc R . . . .
C11 C 0.5019(7) 0.1590(2) 0.4313(8) 0.0385(13) Uani 1 1 d . . . . .
H11 H 0.5590 0.1251 0.4498 0.046 Uiso 1 1 calc R . . . .
C12 C 0.5778(7) 0.2122(3) 0.4449(8) 0.0359(12) Uani 1 1 d . . . . .
C13 C 0.7355(7) 0.2202(3) 0.4811(8) 0.0357(12) Uani 1 1 d . . . . .
C14 C 0.8032(6) 0.2713(3) 0.4921(8) 0.0391(13) Uani 1 1 d . . . . .
H14 H 0.9098 0.2742 0.5171 0.047 Uiso 1 1 calc R . . . .
C15 C 0.7115(6) 0.3211(3) 0.4654(8) 0.0358(13) Uani 1 1 d . . . . .
H15 H 0.7570 0.3573 0.4761 0.043 Uiso 1 1 calc R . . . .
C16 C 0.5582(6) 0.3159(2) 0.4246(7) 0.0309(12) Uani 1 1 d . . . . .
C17 C 0.4644(6) 0.3677(2) 0.3837(7) 0.0285(11) Uani 1 1 d . . . . .
C18 C 0.4902(6) 0.2623(2) 0.4157(7) 0.0313(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 Cl1 2.3455(14) . ?
Co1 Cl1 2.3455(14) 3_666 ?
Co1 O1 2.236(4) . ?
Co1 O1 2.236(4) 3_666 ?
Co1 N1 2.202(4) . ?
Co1 N1 2.202(4) 3_666 ?
O1 C17 1.217(7) . ?
O2 C7 1.211(7) . ?
O3 N3 1.237(7) . ?
O4 N3 1.232(7) . ?
N1 C1 1.335(7) . ?
N1 C5 1.349(7) . ?
N2 C6 1.491(6) . ?
N2 C7 1.388(7) . ?
N2 C17 1.395(6) . ?
N3 C13 1.471(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.392(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.359(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(7) . ?
C5 C6 1.497(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.482(8) . ?
C8 C9 1.376(8) . ?
C8 C18 1.404(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.352(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.432(9) . ?
C12 C13 1.414(9) . ?
C12 C18 1.421(8) . ?
C13 C14 1.355(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.434(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.366(8) . ?
C16 C17 1.486(7) . ?
C16 C18 1.410(8) . ?

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
Cl1 Co1 Cl1 180.0 . 3_666 ?
O1 Co1 Cl1 95.53(11) . 3_666 ?
O1 Co1 Cl1 95.53(11) 3_666 . ?
O1 Co1 Cl1 84.47(11) 3_666 3_666 ?
O1 Co1 Cl1 84.47(11) . . ?
O1 Co1 O1 180.00(18) 3_666 . ?
N1 Co1 Cl1 90.04(13) . . ?
N1 Co1 Cl1 89.96(13) . 3_666 ?
N1 Co1 Cl1 89.96(13) 3_666 . ?
N1 Co1 Cl1 90.04(13) 3_666 3_666 ?
N1 Co1 O1 89.40(14) . . ?
N1 Co1 O1 90.60(14) 3_666 . ?
N1 Co1 O1 90.60(14) . 3_666 ?
N1 Co1 O1 89.40(14) 3_666 3_666 ?
N1 Co1 N1 180.0 3_666 . ?
C17 O1 Co1 138.2(3) . . ?
C1 N1 Co1 115.6(3) . . ?
C1 N1 C5 118.1(4) . . ?
C5 N1 Co1 126.3(4) . . ?
C7 N2 C6 117.9(4) . . ?
C7 N2 C17 125.7(4) . . ?
C17 N2 C6 116.3(4) . . ?
O3 N3 C13 119.5(5) . . ?
O4 N3 O3 123.5(5) . . ?
O4 N3 C13 116.9(5) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.9(5) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.7(6) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.6(5) . . ?
N1 C5 C6 118.7(4) . . ?
C4 C5 C6 119.7(5) . . ?
N2 C6 C5 111.8(4) . . ?
N2 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
O2 C7 N2 120.2(5) . . ?
O2 C7 C8 122.6(5) . . ?
N2 C7 C8 117.2(5) . . ?
C9 C8 C7 118.1(5) . . ?
C9 C8 C18 122.3(5) . . ?
C18 C8 C7 119.6(5) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(6) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.3(6) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.6(6) . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 125.8(6) . . ?
C13 C12 C18 115.4(6) . . ?
C18 C12 C11 118.7(5) . . ?
C12 C13 N3 117.4(6) . . ?
C14 C13 N3 118.5(5) . . ?
C14 C13 C12 124.1(5) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(6) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 118.9(5) . . ?
C15 C16 C18 120.5(5) . . ?
C18 C16 C17 120.6(5) . . ?
O1 C17 N2 121.1(5) . . ?
O1 C17 C16 123.1(5) . . ?
N2 C17 C16 115.8(5) . . ?
C8 C18 C12 117.7(5) . . ?
C8 C18 C16 120.8(5) . . ?
C16 C18 C12 121.4(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
Co1 O1 C17 N2 52.6(8) . . . . ?
Co1 O1 C17 C16 -129.2(5) . . . . ?
Co1 N1 C1 C2 178.0(4) . . . . ?
Co1 N1 C5 C4 -178.3(4) . . . . ?
Co1 N1 C5 C6 2.4(7) . . . . ?
O2 C7 C8 C9 3.3(9) . . . . ?
O2 C7 C8 C18 -176.6(5) . . . . ?
O3 N3 C13 C12 -49.4(8) . . . . ?
O3 N3 C13 C14 130.9(6) . . . . ?
O4 N3 C13 C12 132.2(6) . . . . ?
O4 N3 C13 C14 -47.6(8) . . . . ?
N1 C1 C2 C3 0.1(9) . . . . ?
N1 C5 C6 N2 84.4(6) . . . . ?
N2 C7 C8 C9 -175.4(5) . . . . ?
N2 C7 C8 C18 4.7(8) . . . . ?
N3 C13 C14 C15 179.6(5) . . . . ?
C1 N1 C5 C4 0.5(8) . . . . ?
C1 N1 C5 C6 -178.7(5) . . . . ?
C1 C2 C3 C4 1.3(9) . . . . ?
C2 C3 C4 C5 -1.8(9) . . . . ?
C3 C4 C5 N1 0.8(9) . . . . ?
C3 C4 C5 C6 -179.9(5) . . . . ?
C4 C5 C6 N2 -94.9(6) . . . . ?
C5 N1 C1 C2 -1.0(8) . . . . ?
C6 N2 C7 O2 -3.2(8) . . . . ?
C6 N2 C7 C8 175.6(5) . . . . ?
C6 N2 C17 O1 -1.2(7) . . . . ?
C6 N2 C17 C16 -179.5(4) . . . . ?
C7 N2 C6 C5 91.3(5) . . . . ?
C7 N2 C17 O1 179.2(5) . . . . ?
C7 N2 C17 C16 0.9(7) . . . . ?
C7 C8 C9 C10 179.5(5) . . . . ?
C7 C8 C18 C12 179.1(5) . . . . ?
C7 C8 C18 C16 -0.6(8) . . . . ?
C8 C9 C10 C11 1.6(10) . . . . ?
C9 C8 C18 C12 -0.8(8) . . . . ?
C9 C8 C18 C16 179.5(5) . . . . ?
C9 C10 C11 C12 -1.1(10) . . . . ?
C10 C11 C12 C13 -178.7(6) . . . . ?
C10 C11 C12 C18 -0.3(9) . . . . ?
C11 C12 C13 N3 -0.1(8) . . . . ?
C11 C12 C13 C14 179.7(6) . . . . ?
C11 C12 C18 C8 1.3(8) . . . . ?
C11 C12 C18 C16 -179.1(5) . . . . ?
C12 C13 C14 C15 -0.1(9) . . . . ?
C13 C12 C18 C8 179.8(5) . . . . ?
C13 C12 C18 C16 -0.5(7) . . . . ?
C13 C14 C15 C16 -1.8(8) . . . . ?
C14 C15 C16 C17 -175.7(5) . . . . ?
C14 C15 C16 C18 2.4(8) . . . . ?
C15 C16 C17 O1 3.3(8) . . . . ?
C15 C16 C17 N2 -178.4(5) . . . . ?
C15 C16 C18 C8 178.4(5) . . . . ?
C15 C16 C18 C12 -1.3(8) . . . . ?
C17 N2 C6 C5 -88.3(5) . . . . ?
C17 N2 C7 O2 176.4(5) . . . . ?
C17 N2 C7 C8 -4.9(8) . . . . ?
C17 C16 C18 C8 -3.6(7) . . . . ?
C17 C16 C18 C12 176.8(5) . . . . ?
C18 C8 C9 C10 -0.6(9) . . . . ?
C18 C12 C13 N3 -178.5(5) . . . . ?
C18 C12 C13 C14 1.2(8) . . . . ?
C18 C16 C17 O1 -174.8(5) . . . . ?
C18 C16 C17 N2 3.5(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L4
_database_code_depnum_ccdc_archive 'CCDC 1511751'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 N3 O4'
_chemical_formula_sum            'C18 H11 N3 O4'
_chemical_formula_weight         333.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.9920(4)
_cell_length_b                   18.0217(14)
_cell_length_c                   22.5014(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2835.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1505
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.048
_cell_measurement_theta_min      3.929
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.8747.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23779
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.445
_diffrn_reflns_theta_min         3.929
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1672
_reflns_number_total             2607
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1580P)²+0.9820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2255
_refine_ls_wR_factor_ref         0.2698
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C1, C2, C3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0698(5) 0.34622(17) 0.30815(16) 0.0671(9) Uani 1 1 d . . . . .
O2 O 0.0755(5) 0.55169(19) 0.42424(15) 0.0682(9) Uani 1 1 d . . . . .
O3 O 0.2894(4) 0.75916(17) 0.17276(16) 0.0701(9) Uani 1 1 d . . . . .
O4 O 0.0585(5) 0.70179(17) 0.12709(14) 0.0640(8) Uani 1 1 d . . . . .
N1 N 0.4855(8) 0.4044(3) 0.5128(3) 0.0983(17) Uani 1 1 d . . . . .
N2 N 0.0656(5) 0.44867(19) 0.36684(16) 0.0549(8) Uani 1 1 d . . . . .
N3 N 0.1667(5) 0.7103(2) 0.16936(17) 0.0590(9) Uani 1 1 d . . . . .
C1 C 0.5695(9) 0.3448(4) 0.4954(3) 0.0896(16) Uani 1 1 d . U . . .
H1 H 0.6904 0.3336 0.5125 0.107 Uiso 1 1 calc R . . . .
C2 C 0.4986(10) 0.2966(4) 0.4544(3) 0.0932(16) Uani 1 1 d . U . . .
H2 H 0.5680 0.2536 0.4430 0.112 Uiso 1 1 calc R . . . .
C3 C 0.3147(10) 0.3131(3) 0.4290(2) 0.0832(15) Uani 1 1 d . U . . .
H3 H 0.2559 0.2802 0.4015 0.100 Uiso 1 1 calc R . . . .
C4 C 0.2280(6) 0.3773(2) 0.44575(18) 0.0536(9) Uani 1 1 d . . . . .
C5 C 0.3220(9) 0.4197(3) 0.4876(2) 0.0769(14) Uani 1 1 d . . . . .
H5 H 0.2617 0.4646 0.4992 0.092 Uiso 1 1 calc R . . . .
C6 C 0.0411(6) 0.4017(3) 0.4202(2) 0.0629(11) Uani 1 1 d . . . . .
H6A H -0.0354 0.3574 0.4096 0.075 Uiso 1 1 calc R . . . .
H6B H -0.0306 0.4299 0.4507 0.075 Uiso 1 1 calc R . . . .
C7 C 0.0828(5) 0.5255(3) 0.3750(2) 0.0570(10) Uani 1 1 d . . . . .
C8 C 0.1101(5) 0.5712(2) 0.3211(2) 0.0527(10) Uani 1 1 d . . . . .
C9 C 0.1419(6) 0.6458(2) 0.3266(2) 0.0573(10) Uani 1 1 d . . . . .
H9 H 0.1484 0.6677 0.3649 0.069 Uiso 1 1 calc R . . . .
C10 C 0.1651(5) 0.6907(2) 0.2753(2) 0.0571(10) Uani 1 1 d . . . . .
H10 H 0.1917 0.7421 0.2793 0.069 Uiso 1 1 calc R . . . .
C11 C 0.1493(5) 0.6598(2) 0.2207(2) 0.0547(10) Uani 1 1 d . . . . .
C12 C 0.1171(5) 0.5830(2) 0.2113(2) 0.0531(10) Uani 1 1 d . . . . .
C13 C 0.1057(5) 0.5466(2) 0.15471(19) 0.0538(10) Uani 1 1 d . . . . .
H13 H 0.1126 0.5752 0.1193 0.065 Uiso 1 1 calc R . . . .
C14 C 0.0853(5) 0.4724(2) 0.1513(2) 0.0560(10) Uani 1 1 d . . . . .
H14 H 0.0791 0.4493 0.1134 0.067 Uiso 1 1 calc R . . . .
C15 C 0.0730(5) 0.4288(3) 0.2025(2) 0.0575(10) Uani 1 1 d . . . . .
H15 H 0.0587 0.3766 0.1991 0.069 Uiso 1 1 calc R . . . .
C16 C 0.0815(5) 0.4611(2) 0.2579(2) 0.0541(10) Uani 1 1 d . . . . .
C17 C 0.0718(5) 0.4131(2) 0.3114(2) 0.0554(10) Uani 1 1 d . . . . .
C18 C 0.1018(5) 0.5388(2) 0.26338(19) 0.0507(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.208(5) . ?
O2 C7 1.204(5) . ?
O3 N3 1.231(5) . ?
O4 N3 1.225(5) . ?
N1 C1 1.284(9) . ?
N1 C5 1.306(7) . ?
N2 C6 1.480(5) . ?
N2 C7 1.402(6) . ?
N2 C17 1.403(6) . ?
N3 C11 1.476(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.361(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.438(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.360(7) . ?
C4 C5 1.379(7) . ?
C4 C6 1.494(6) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.480(6) . ?
C8 C9 1.368(6) . ?
C8 C18 1.425(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.418(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.353(6) . ?
C11 C12 1.419(6) . ?
C12 C13 1.435(6) . ?
C12 C18 1.421(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.347(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(6) . ?
C16 C17 1.483(6) . ?
C16 C18 1.412(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.4(6) . . ?
C7 N2 C6 117.9(4) . . ?
C7 N2 C17 124.4(4) . . ?
C17 N2 C6 117.7(4) . . ?
O3 N3 C11 116.7(4) . . ?
O4 N3 O3 124.7(4) . . ?
O4 N3 C11 118.6(4) . . ?
N1 C1 H1 117.5 . . ?
N1 C1 C2 125.0(6) . . ?
C2 C1 H1 117.5 . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.6(6) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 C5 116.6(5) . . ?
C3 C4 C6 122.3(4) . . ?
C5 C4 C6 121.1(4) . . ?
N1 C5 C4 126.6(5) . . ?
N1 C5 H5 116.7 . . ?
C4 C5 H5 116.7 . . ?
N2 C6 C4 112.3(3) . . ?
N2 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C4 C6 H6A 109.1 . . ?
C4 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O2 C7 N2 120.3(4) . . ?
O2 C7 C8 122.8(4) . . ?
N2 C7 C8 116.9(4) . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 C18 119.5(4) . . ?
C18 C8 C7 120.9(4) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 N3 116.8(4) . . ?
C10 C11 C12 123.3(4) . . ?
C12 C11 N3 119.9(4) . . ?
C11 C12 C13 125.9(4) . . ?
C11 C12 C18 115.9(4) . . ?
C18 C12 C13 118.1(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(4) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.1(4) . . ?
C15 C16 C18 120.2(4) . . ?
C18 C16 C17 120.8(4) . . ?
O1 C17 N2 120.6(4) . . ?
O1 C17 C16 122.2(4) . . ?
N2 C17 C16 117.2(4) . . ?
C12 C18 C8 121.2(4) . . ?
C16 C18 C8 119.4(4) . . ?
C16 C18 C12 119.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 C9 4.7(6) . . . . ?
O2 C7 C8 C18 -174.7(4) . . . . ?
O3 N3 C11 C10 40.1(5) . . . . ?
O3 N3 C11 C12 -140.0(4) . . . . ?
O4 N3 C11 C10 -139.0(4) . . . . ?
O4 N3 C11 C12 40.9(5) . . . . ?
N1 C1 C2 C3 -0.6(10) . . . . ?
N2 C7 C8 C9 -175.2(3) . . . . ?
N2 C7 C8 C18 5.4(5) . . . . ?
N3 C11 C12 C13 2.4(5) . . . . ?
N3 C11 C12 C18 -179.9(3) . . . . ?
C1 N1 C5 C4 2.3(10) . . . . ?
C1 C2 C3 C4 2.7(9) . . . . ?
C2 C3 C4 C5 -2.3(8) . . . . ?
C2 C3 C4 C6 177.2(5) . . . . ?
C3 C4 C5 N1 -0.2(9) . . . . ?
C3 C4 C6 N2 -90.5(6) . . . . ?
C5 N1 C1 C2 -1.8(10) . . . . ?
C5 C4 C6 N2 89.0(5) . . . . ?
C6 N2 C7 O2 -0.8(5) . . . . ?
C6 N2 C7 C8 179.1(3) . . . . ?
C6 N2 C17 O1 -4.7(5) . . . . ?
C6 N2 C17 C16 175.5(3) . . . . ?
C6 C4 C5 N1 -179.7(5) . . . . ?
C7 N2 C6 C4 -89.1(4) . . . . ?
C7 N2 C17 O1 174.6(3) . . . . ?
C7 N2 C17 C16 -5.2(5) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C7 C8 C18 C12 176.4(3) . . . . ?
C7 C8 C18 C16 -4.8(5) . . . . ?
C8 C9 C10 C11 2.3(6) . . . . ?
C9 C8 C18 C12 -2.9(5) . . . . ?
C9 C8 C18 C16 175.9(3) . . . . ?
C9 C10 C11 N3 177.4(3) . . . . ?
C9 C10 C11 C12 -2.5(6) . . . . ?
C10 C11 C12 C13 -177.7(4) . . . . ?
C10 C11 C12 C18 0.0(5) . . . . ?
C11 C12 C13 C14 176.2(4) . . . . ?
C11 C12 C18 C8 2.7(5) . . . . ?
C11 C12 C18 C16 -176.2(3) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C13 C12 C18 C8 -179.4(3) . . . . ?
C13 C12 C18 C16 1.7(5) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C14 C15 C16 C17 -178.8(3) . . . . ?
C14 C15 C16 C18 0.3(5) . . . . ?
C15 C16 C17 O1 5.1(5) . . . . ?
C15 C16 C17 N2 -175.1(3) . . . . ?
C15 C16 C18 C8 179.9(3) . . . . ?
C15 C16 C18 C12 -1.2(5) . . . . ?
C17 N2 C6 C4 90.3(4) . . . . ?
C17 N2 C7 O2 179.8(4) . . . . ?
C17 N2 C7 C8 -0.3(5) . . . . ?
C17 C16 C18 C8 -1.0(5) . . . . ?
C17 C16 C18 C12 177.9(3) . . . . ?
C18 C8 C9 C10 0.4(5) . . . . ?
C18 C12 C13 C14 -1.4(5) . . . . ?
C18 C16 C17 O1 -174.0(3) . . . . ?
C18 C16 C17 N2 5.8(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1511756'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 Cl2 N2 O2 Zn'
_chemical_formula_sum            'C18 H12 Cl2 N2 O2 Zn'
_chemical_formula_weight         424.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3139(2)
_cell_length_b                   8.5996(3)
_cell_length_c                   14.4546(5)
_cell_angle_alpha                94.9430(10)
_cell_angle_beta                 102.0330(10)
_cell_angle_gamma                113.9780(10)
_cell_volume                     797.44(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4082
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.328
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0487 before and 0.0216 after correction.
The Ratio of minimum to maximum transmission is 0.8212.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6138
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3633
_reflns_number_total             3975
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²+0.4650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0530
_refine_ls_wR_factor_ref         0.0546
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.50892(3) 0.11531(2) 0.15807(2) 0.01219(5) Uani 1 1 d . . . . .
Cl1 Cl 0.75176(6) 0.09071(5) 0.09935(3) 0.01828(8) Uani 1 1 d . . . . .
Cl2 Cl 0.21795(5) -0.09858(4) 0.16652(2) 0.01493(8) Uani 1 1 d . . . . .
O1 O 0.66326(17) 0.22424(13) 0.30368(7) 0.0150(2) Uani 1 1 d . . . . .
O2 O 0.81476(17) 0.79793(14) 0.35238(8) 0.0178(2) Uani 1 1 d . . . . .
N1 N 0.44017(19) 0.31608(16) 0.12398(9) 0.0119(2) Uani 1 1 d . . . . .
N2 N 0.75646(18) 0.51471(15) 0.33018(8) 0.0113(2) Uani 1 1 d . . . . .
C1 C 0.2566(2) 0.27737(19) 0.06124(10) 0.0141(3) Uani 1 1 d . . . . .
H1 H 0.1620 0.1590 0.0372 0.017 Uiso 1 1 calc R . . . .
C2 C 0.2007(2) 0.4044(2) 0.03044(11) 0.0159(3) Uani 1 1 d . . . . .
H2 H 0.0698 0.3733 -0.0137 0.019 Uiso 1 1 calc R . . . .
C3 C 0.3389(2) 0.5774(2) 0.06518(11) 0.0156(3) Uani 1 1 d . . . . .
H3 H 0.3056 0.6666 0.0439 0.019 Uiso 1 1 calc R . . . .
C4 C 0.5271(2) 0.61842(19) 0.13163(10) 0.0139(3) Uani 1 1 d . . . . .
H4 H 0.6228 0.7360 0.1575 0.017 Uiso 1 1 calc R . . . .
C5 C 0.5730(2) 0.48513(18) 0.15954(10) 0.0115(3) Uani 1 1 d . . . . .
C6 C 0.7764(2) 0.52370(18) 0.23056(10) 0.0122(3) Uani 1 1 d . . . . .
H6A H 0.8277 0.4395 0.2105 0.015 Uiso 1 1 calc R . . . .
H6B H 0.8802 0.6411 0.2295 0.015 Uiso 1 1 calc R . . . .
C7 C 0.7096(2) 0.35860(18) 0.36063(10) 0.0118(3) Uani 1 1 d . . . . .
C8 C 0.7181(2) 0.35752(18) 0.46304(10) 0.0113(3) Uani 1 1 d . . . . .
C9 C 0.6939(2) 0.20833(19) 0.49871(11) 0.0139(3) Uani 1 1 d . . . . .
H9 H 0.6748 0.1078 0.4574 0.017 Uiso 1 1 calc R . . . .
C10 C 0.6974(2) 0.20518(19) 0.59626(11) 0.0158(3) Uani 1 1 d . . . . .
H10 H 0.6800 0.1023 0.6205 0.019 Uiso 1 1 calc R . . . .
C11 C 0.7260(2) 0.3507(2) 0.65665(11) 0.0154(3) Uani 1 1 d . . . . .
H11 H 0.7243 0.3461 0.7219 0.018 Uiso 1 1 calc R . . . .
C12 C 0.7577(2) 0.50696(19) 0.62317(10) 0.0132(3) Uani 1 1 d . . . . .
C13 C 0.8009(2) 0.6629(2) 0.68441(11) 0.0165(3) Uani 1 1 d . . . . .
H13 H 0.8062 0.6636 0.7507 0.020 Uiso 1 1 calc R . . . .
C14 C 0.8352(2) 0.8128(2) 0.64922(11) 0.0173(3) Uani 1 1 d . . . . .
H14 H 0.8657 0.9164 0.6913 0.021 Uiso 1 1 calc R . . . .
C15 C 0.8253(2) 0.81332(19) 0.55091(11) 0.0154(3) Uani 1 1 d . . . . .
H15 H 0.8465 0.9169 0.5268 0.018 Uiso 1 1 calc R . . . .
C16 C 0.7852(2) 0.66474(18) 0.48929(10) 0.0119(3) Uani 1 1 d . . . . .
C17 C 0.7865(2) 0.66993(18) 0.38761(10) 0.0124(3) Uani 1 1 d . . . . .
C18 C 0.7526(2) 0.50965(18) 0.52432(10) 0.0114(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.1960(4) . ?
Zn1 Cl2 2.2119(4) . ?
Zn1 O1 2.0957(11) . ?
Zn1 N1 2.0557(12) . ?
O1 C7 1.2365(17) . ?
O2 C17 1.2121(18) . ?
N1 C1 1.3464(19) . ?
N1 C5 1.3551(18) . ?
N2 C6 1.4826(17) . ?
N2 C7 1.3799(18) . ?
N2 C17 1.4191(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3875(19) . ?
C5 C6 1.5103(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.4697(19) . ?
C8 C9 1.3822(19) . ?
C8 C18 1.4137(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.408(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.414(2) . ?
C12 C13 1.420(2) . ?
C12 C18 1.424(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.408(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(2) . ?
C16 C17 1.476(2) . ?
C16 C18 1.4142(19) . ?

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
Cl1 Zn1 Cl2 126.712(15) . . ?
O1 Zn1 Cl1 102.95(3) . . ?
O1 Zn1 Cl2 102.27(3) . . ?
N1 Zn1 Cl1 115.15(3) . . ?
N1 Zn1 Cl2 107.28(4) . . ?
N1 Zn1 O1 97.00(4) . . ?
C7 O1 Zn1 137.81(10) . . ?
C1 N1 Zn1 118.23(10) . . ?
C1 N1 C5 118.61(12) . . ?
C5 N1 Zn1 123.14(10) . . ?
C7 N2 C6 118.71(12) . . ?
C7 N2 C17 124.58(12) . . ?
C17 N2 C6 116.70(11) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.34(14) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.95(14) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.00(13) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.06(13) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.00(13) . . ?
N1 C5 C6 117.17(12) . . ?
C4 C5 C6 120.83(13) . . ?
N2 C6 C5 112.37(11) . . ?
N2 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 N2 121.05(13) . . ?
O1 C7 C8 121.11(13) . . ?
N2 C7 C8 117.84(12) . . ?
C9 C8 C7 119.75(13) . . ?
C9 C8 C18 120.62(13) . . ?
C18 C8 C7 119.62(13) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.08(14) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.22(14) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.10(14) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 122.90(14) . . ?
C11 C12 C18 118.61(13) . . ?
C13 C12 C18 118.47(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.95(14) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.18(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.57(14) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 119.84(13) . . ?
C15 C16 C18 120.17(13) . . ?
C18 C16 C17 119.93(13) . . ?
O2 C17 N2 119.57(13) . . ?
O2 C17 C16 123.88(13) . . ?
N2 C17 C16 116.54(12) . . ?
C8 C18 C12 119.32(13) . . ?
C8 C18 C16 121.04(13) . . ?
C16 C18 C12 119.63(13) . . ?

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
Zn1 O1 C7 N2 -33.5(2) . . . . ?
Zn1 O1 C7 C8 147.01(11) . . . . ?
Zn1 N1 C1 C2 -176.94(11) . . . . ?
Zn1 N1 C5 C4 176.69(10) . . . . ?
Zn1 N1 C5 C6 -2.54(17) . . . . ?
O1 C7 C8 C9 6.3(2) . . . . ?
O1 C7 C8 C18 -174.15(13) . . . . ?
N1 C1 C2 C3 0.2(2) . . . . ?
N1 C5 C6 N2 -83.08(15) . . . . ?
N2 C7 C8 C9 -173.21(13) . . . . ?
N2 C7 C8 C18 6.31(19) . . . . ?
C1 N1 C5 C4 -1.4(2) . . . . ?
C1 N1 C5 C6 179.34(12) . . . . ?
C1 C2 C3 C4 -1.6(2) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C3 C4 C5 N1 0.1(2) . . . . ?
C3 C4 C5 C6 179.28(13) . . . . ?
C4 C5 C6 N2 97.68(15) . . . . ?
C5 N1 C1 C2 1.3(2) . . . . ?
C6 N2 C7 O1 -7.6(2) . . . . ?
C6 N2 C7 C8 171.94(12) . . . . ?
C6 N2 C17 O2 4.08(19) . . . . ?
C6 N2 C17 C16 -174.68(12) . . . . ?
C7 N2 C6 C5 90.55(15) . . . . ?
C7 N2 C17 O2 -175.54(13) . . . . ?
C7 N2 C17 C16 5.70(19) . . . . ?
C7 C8 C9 C10 -178.64(13) . . . . ?
C7 C8 C18 C12 179.12(12) . . . . ?
C7 C8 C18 C16 -1.9(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C8 C18 C12 -1.4(2) . . . . ?
C9 C8 C18 C16 177.63(13) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
C10 C11 C12 C13 -175.87(14) . . . . ?
C10 C11 C12 C18 2.1(2) . . . . ?
C11 C12 C13 C14 178.56(14) . . . . ?
C11 C12 C18 C8 -0.6(2) . . . . ?
C11 C12 C18 C16 -179.60(13) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C12 C18 C8 177.48(13) . . . . ?
C13 C12 C18 C16 -1.5(2) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C14 C15 C16 C17 -176.75(13) . . . . ?
C14 C15 C16 C18 0.3(2) . . . . ?
C15 C16 C17 O2 -2.4(2) . . . . ?
C15 C16 C17 N2 176.27(13) . . . . ?
C15 C16 C18 C8 -177.89(13) . . . . ?
C15 C16 C18 C12 1.1(2) . . . . ?
C17 N2 C6 C5 -89.10(14) . . . . ?
C17 N2 C7 O1 172.02(13) . . . . ?
C17 N2 C7 C8 -8.4(2) . . . . ?
C17 C16 C18 C8 -0.8(2) . . . . ?
C17 C16 C18 C12 178.15(12) . . . . ?
C18 C8 C9 C10 1.8(2) . . . . ?
C18 C12 C13 C14 0.6(2) . . . . ?
C18 C16 C17 O2 -179.48(14) . . . . ?
C18 C16 C17 N2 -0.78(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1511754'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C36 H28 Co N4 O6, 2(C18 H12 Cl3 Co N2 O2), 4(C2 H3 N)'
_chemical_formula_sum            'C80 H64 Cl6 Co3 N12 O10'
_chemical_formula_weight         1742.92
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.4021(5)
_cell_length_b                   13.3749(4)
_cell_length_c                   17.2099(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.7917(10)
_cell_angle_gamma                90
_cell_volume                     3771.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6133
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.029
_cell_measurement_theta_min      2.264
_shelx_estimated_absorpt_T_max   0.896
_shelx_estimated_absorpt_T_min   0.786
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0498 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.8998.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1782
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32344
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.176
_diffrn_reflns_theta_min         1.675
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6873
_reflns_number_total             10179
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.813
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         10179
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+1.8060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0824
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1B = O1-H1A
 0.95 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C24(H24A,H24B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28),
  C29(H29), C31(H31), C32(H32), C33(H33)
3.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C40(H40A,H40B,H40C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37896(13) 0.65753(17) 0.54138(12) 0.0166(5) Uani 1 1 d . . . . .
H1 H 0.4286 0.6880 0.5598 0.020 Uiso 1 1 calc R . . . .
C2 C 0.30662(13) 0.70986(17) 0.54868(13) 0.0183(5) Uani 1 1 d . . . . .
H2 H 0.3067 0.7739 0.5725 0.022 Uiso 1 1 calc R . . . .
C3 C 0.23456(13) 0.66686(17) 0.52060(13) 0.0184(5) Uani 1 1 d . . . . .
H3 H 0.1841 0.7011 0.5241 0.022 Uiso 1 1 calc R . . . .
C4 C 0.23723(13) 0.57316(17) 0.48738(12) 0.0163(5) Uani 1 1 d . . . . .
H4 H 0.1885 0.5427 0.4668 0.020 Uiso 1 1 calc R . . . .
C5 C 0.31106(12) 0.52356(16) 0.48403(11) 0.0125(4) Uani 1 1 d . . . . .
C6 C 0.31377(12) 0.41872(16) 0.45214(11) 0.0133(4) Uani 1 1 d . . . . .
H6A H 0.3586 0.3814 0.4797 0.016 Uiso 1 1 calc R . . . .
H6B H 0.2619 0.3843 0.4620 0.016 Uiso 1 1 calc R . . . .
C7 C 0.25666(13) 0.41053(16) 0.31664(12) 0.0140(4) Uani 1 1 d . . . . .
C8 C 0.27103(13) 0.40814(15) 0.23334(12) 0.0130(4) Uani 1 1 d . . . . .
C9 C 0.20583(14) 0.40238(16) 0.17995(13) 0.0173(5) Uani 1 1 d . . . . .
H9 H 0.1517 0.4015 0.1973 0.021 Uiso 1 1 calc R . . . .
C10 C 0.21881(14) 0.39784(17) 0.10015(13) 0.0210(5) Uani 1 1 d . . . . .
H10 H 0.1735 0.3946 0.0636 0.025 Uiso 1 1 calc R . . . .
C11 C 0.29692(14) 0.39808(17) 0.07458(13) 0.0203(5) Uani 1 1 d . . . . .
H11 H 0.3049 0.3950 0.0203 0.024 Uiso 1 1 calc R . . . .
C12 C 0.36545(14) 0.40273(16) 0.12736(12) 0.0171(5) Uani 1 1 d . . . . .
C13 C 0.44690(14) 0.40185(17) 0.10325(13) 0.0200(5) Uani 1 1 d . . . . .
H13 H 0.4567 0.3983 0.0494 0.024 Uiso 1 1 calc R . . . .
C14 C 0.51195(14) 0.40603(17) 0.15679(13) 0.0202(5) Uani 1 1 d . . . . .
H14 H 0.5661 0.4045 0.1396 0.024 Uiso 1 1 calc R . . . .
C15 C 0.49876(13) 0.41250(16) 0.23661(13) 0.0157(5) Uani 1 1 d . . . . .
H15 H 0.5440 0.4157 0.2732 0.019 Uiso 1 1 calc R . . . .
C16 C 0.41990(12) 0.41422(15) 0.26212(12) 0.0127(4) Uani 1 1 d . . . . .
C17 C 0.40608(12) 0.42096(15) 0.34502(12) 0.0124(4) Uani 1 1 d . . . . .
C18 C 0.35220(13) 0.40868(15) 0.20819(12) 0.0131(4) Uani 1 1 d . . . . .
Co1 Co 0.5000 0.5000 0.5000 0.01201(9) Uani 1 2 d S T P . .
N1 N 0.38223(10) 0.56579(13) 0.50956(10) 0.0132(4) Uani 1 1 d . . . . .
N2 N 0.32649(10) 0.41784(13) 0.36798(10) 0.0115(4) Uani 1 1 d . . . . .
O1 O 0.52798(9) 0.62553(12) 0.43300(9) 0.0171(3) Uani 1 1 d D . . . .
H1A H 0.5719(12) 0.6155(18) 0.4050(13) 0.026 Uiso 1 1 d DR . . . .
H1B H 0.4902(13) 0.6502(17) 0.3986(12) 0.026 Uiso 1 1 d DR . . . .
O2 O 0.46315(8) 0.42786(11) 0.39476(8) 0.0156(3) Uani 1 1 d . . . . .
O3 O 0.18928(9) 0.40680(12) 0.34358(9) 0.0187(3) Uani 1 1 d . . . . .
C19 C 0.66750(14) 0.87244(17) 0.22044(13) 0.0196(5) Uani 1 1 d . . . . .
H19 H 0.7246 0.8797 0.2307 0.024 Uiso 1 1 calc R . . . .
C20 C 0.62047(14) 0.95745(18) 0.21106(14) 0.0231(5) Uani 1 1 d . . . . .
H20 H 0.6448 1.0218 0.2149 0.028 Uiso 1 1 calc R . . . .
C21 C 0.53776(14) 0.94755(17) 0.19609(14) 0.0213(5) Uani 1 1 d . . . . .
H21 H 0.5041 1.0050 0.1895 0.026 Uiso 1 1 calc R . . . .
C22 C 0.50408(13) 0.85254(17) 0.19074(13) 0.0187(5) Uani 1 1 d . . . . .
H22 H 0.4471 0.8444 0.1803 0.022 Uiso 1 1 calc R . . . .
C23 C 0.55412(13) 0.76962(16) 0.20072(12) 0.0148(4) Uani 1 1 d . . . . .
C24 C 0.52228(12) 0.66384(17) 0.19550(13) 0.0177(5) Uani 1 1 d . . . . .
H24A H 0.5492 0.6286 0.1531 0.021 Uiso 1 1 calc R . . . .
H24B H 0.5371 0.6287 0.2448 0.021 Uiso 1 1 calc R . . . .
C25 C 0.38417(13) 0.65949(16) 0.24448(13) 0.0150(4) Uani 1 1 d . . . . .
C26 C 0.29522(13) 0.65769(16) 0.22771(13) 0.0150(4) Uani 1 1 d . . . . .
C27 C 0.24354(13) 0.65850(16) 0.28899(14) 0.0192(5) Uani 1 1 d . . . . .
H27 H 0.2656 0.6593 0.3411 0.023 Uiso 1 1 calc R . . . .
C28 C 0.15852(14) 0.65808(18) 0.27438(15) 0.0255(6) Uani 1 1 d . . . . .
H28 H 0.1233 0.6580 0.3166 0.031 Uiso 1 1 calc R . . . .
C29 C 0.12643(14) 0.65778(18) 0.19966(16) 0.0269(6) Uani 1 1 d . . . . .
H29 H 0.0688 0.6584 0.1907 0.032 Uiso 1 1 calc R . . . .
C30 C 0.17706(13) 0.65662(17) 0.13507(14) 0.0208(5) Uani 1 1 d . . . . .
C31 C 0.14659(15) 0.65615(18) 0.05658(15) 0.0269(6) Uani 1 1 d . . . . .
H31 H 0.0893 0.6578 0.0454 0.032 Uiso 1 1 calc R . . . .
C32 C 0.19839(15) 0.65333(18) -0.00321(15) 0.0270(6) Uani 1 1 d . . . . .
H32 H 0.1767 0.6526 -0.0554 0.032 Uiso 1 1 calc R . . . .
C33 C 0.28328(15) 0.65150(17) 0.01169(14) 0.0224(5) Uani 1 1 d . . . . .
H33 H 0.3187 0.6482 -0.0303 0.027 Uiso 1 1 calc R . . . .
C34 C 0.31549(13) 0.65452(16) 0.08749(13) 0.0164(5) Uani 1 1 d . . . . .
C35 C 0.40460(13) 0.65737(17) 0.10229(13) 0.0167(5) Uani 1 1 d . . . . .
C36 C 0.26326(12) 0.65611(16) 0.15017(13) 0.0157(4) Uani 1 1 d . . . . .
Cl1 Cl 0.68436(3) 0.58485(5) 0.34563(3) 0.02831(15) Uani 1 1 d . . . . .
Cl2 Cl 0.70628(3) 0.55503(4) 0.13355(3) 0.02011(12) Uani 1 1 d . . . . .
Cl3 Cl 0.84342(3) 0.72796(4) 0.25048(3) 0.02200(13) Uani 1 1 d . . . . .
Co2 Co 0.71648(2) 0.66257(2) 0.23447(2) 0.01400(7) Uani 1 1 d . . . . .
N3 N 0.63577(10) 0.77921(13) 0.21565(10) 0.0153(4) Uani 1 1 d . . . . .
N4 N 0.43365(10) 0.65869(14) 0.18081(10) 0.0147(4) Uani 1 1 d . . . . .
O4 O 0.45278(9) 0.66057(13) 0.05089(9) 0.0242(4) Uani 1 1 d . . . . .
O5 O 0.41461(9) 0.66232(12) 0.31058(9) 0.0220(4) Uani 1 1 d . . . . .
C37 C 0.01854(15) 0.3687(2) 0.54947(15) 0.0275(6) Uani 1 1 d . . . . .
C38 C 0.10626(15) 0.3658(2) 0.54695(16) 0.0325(6) Uani 1 1 d . . . . .
H38A H 0.1281 0.3155 0.5838 0.049 Uiso 1 1 calc GR . . . .
H38B H 0.1288 0.4315 0.5611 0.049 Uiso 1 1 calc GR . . . .
H38C H 0.1215 0.3483 0.4943 0.049 Uiso 1 1 calc GR . . . .
N5 N -0.04979(15) 0.3711(2) 0.55327(16) 0.0578(8) Uani 1 1 d . . . . .
C39 C 0.52717(15) -0.0309(2) 0.40483(14) 0.0277(6) Uani 1 1 d . . . . .
C40 C 0.57910(15) 0.0573(2) 0.39983(15) 0.0304(6) Uani 1 1 d . . . . .
H40A H 0.5687 0.1028 0.4429 0.046 Uiso 1 1 calc GR . . . .
H40B H 0.5669 0.0915 0.3502 0.046 Uiso 1 1 calc GR . . . .
H40C H 0.6365 0.0369 0.4031 0.046 Uiso 1 1 calc GR . . . .
N6 N 0.48672(14) -0.09960(19) 0.41072(14) 0.0395(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C1 N1 1.346(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 C6 1.507(3) . ?
C5 N1 1.351(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N2 1.473(2) . ?
C7 C8 1.465(3) . ?
C7 N2 1.415(3) . ?
C7 O3 1.220(2) . ?
C8 C9 1.378(3) . ?
C8 C18 1.420(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.401(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.412(3) . ?
C12 C13 1.418(3) . ?
C12 C18 1.421(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.404(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 C17 1.458(3) . ?
C16 C18 1.414(3) . ?
C17 N2 1.383(2) . ?
C17 O2 1.241(2) . ?
Co1 N1 2.1362(17) . ?
Co1 N1 2.1362(17) 3_666 ?
Co1 O1 2.1001(15) . ?
Co1 O1 2.1001(15) 3_666 ?
Co1 O2 2.1142(14) . ?
Co1 O2 2.1142(14) 3_666 ?
O1 H1A 0.896(16) . ?
O1 H1B 0.900(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(3) . ?
C19 N3 1.352(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.375(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(3) . ?
C23 C24 1.509(3) . ?
C23 N3 1.358(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 N4 1.465(3) . ?
C25 C26 1.474(3) . ?
C25 N4 1.395(3) . ?
C25 O5 1.220(3) . ?
C26 C27 1.385(3) . ?
C26 C36 1.410(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.405(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.366(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.420(3) . ?
C30 C31 1.417(3) . ?
C30 C36 1.425(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.366(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.404(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.384(3) . ?
C34 C35 1.472(3) . ?
C34 C36 1.410(3) . ?
C35 N4 1.411(3) . ?
C35 O4 1.215(2) . ?
Cl1 Co2 2.2619(6) . ?
Cl2 Co2 2.2551(6) . ?
Cl3 Co2 2.2627(6) . ?
Co2 N3 2.0613(18) . ?
C37 C38 1.442(3) . ?
C37 N5 1.126(3) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 C40 1.460(4) . ?
C39 N6 1.141(3) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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 C1 H1 118.4 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.2(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.15(19) . . ?
N1 C5 C4 122.0(2) . . ?
N1 C5 C6 117.84(18) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C6 C5 111.93(17) . . ?
N2 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
N2 C7 C8 116.66(18) . . ?
O3 C7 C8 124.26(19) . . ?
O3 C7 N2 119.08(19) . . ?
C9 C8 C7 119.83(19) . . ?
C9 C8 C18 120.4(2) . . ?
C18 C8 C7 119.75(18) . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.3(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 122.9(2) . . ?
C11 C12 C18 118.5(2) . . ?
C13 C12 C18 118.6(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.18(19) . . ?
C15 C16 C18 120.42(19) . . ?
C18 C16 C17 119.40(18) . . ?
N2 C17 C16 118.14(18) . . ?
O2 C17 C16 122.12(18) . . ?
O2 C17 N2 119.74(18) . . ?
C8 C18 C12 119.25(19) . . ?
C16 C18 C8 121.22(19) . . ?
C16 C18 C12 119.53(19) . . ?
N1 Co1 N1 180.0 3_666 . ?
O1 Co1 N1 86.31(6) . . ?
O1 Co1 N1 86.30(6) 3_666 3_666 ?
O1 Co1 N1 93.70(6) 3_666 . ?
O1 Co1 N1 93.69(6) . 3_666 ?
O1 Co1 O1 180.0 . 3_666 ?
O1 Co1 O2 92.55(6) . 3_666 ?
O1 Co1 O2 87.45(6) . . ?
O1 Co1 O2 92.55(6) 3_666 . ?
O1 Co1 O2 87.45(6) 3_666 3_666 ?
O2 Co1 N1 91.84(6) . . ?
O2 Co1 N1 88.16(6) . 3_666 ?
O2 Co1 N1 91.84(6) 3_666 3_666 ?
O2 Co1 N1 88.16(6) 3_666 . ?
O2 Co1 O2 180.0 . 3_666 ?
C1 N1 C5 117.55(18) . . ?
C1 N1 Co1 117.45(14) . . ?
C5 N1 Co1 124.97(14) . . ?
C7 N2 C6 117.72(16) . . ?
C17 N2 C6 117.49(16) . . ?
C17 N2 C7 124.76(17) . . ?
Co1 O1 H1A 112.2(16) . . ?
Co1 O1 H1B 119.6(16) . . ?
H1A O1 H1B 104(2) . . ?
C17 O2 Co1 143.09(14) . . ?
C20 C19 H19 118.6 . . ?
N3 C19 H19 118.6 . . ?
N3 C19 C20 122.8(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 118.9(2) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.1(2) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C24 122.81(19) . . ?
N3 C23 C22 121.4(2) . . ?
N3 C23 C24 115.79(18) . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
N4 C24 C23 113.07(18) . . ?
N4 C24 H24A 109.0 . . ?
N4 C24 H24B 109.0 . . ?
N4 C25 C26 117.02(19) . . ?
O5 C25 C26 122.6(2) . . ?
O5 C25 N4 120.35(19) . . ?
C27 C26 C25 119.2(2) . . ?
C27 C26 C36 120.5(2) . . ?
C36 C26 C25 120.31(19) . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.1(2) . . ?
C29 C28 H28 119.9 . . ?
C28 C29 H29 119.2 . . ?
C28 C29 C30 121.6(2) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 C36 118.0(2) . . ?
C31 C30 C29 123.6(2) . . ?
C31 C30 C36 118.3(2) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.0(2) . . ?
C32 C31 H31 119.5 . . ?
C31 C32 H32 119.6 . . ?
C31 C32 C33 120.7(2) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.1(2) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 119.6(2) . . ?
C33 C34 C36 120.2(2) . . ?
C36 C34 C35 120.2(2) . . ?
N4 C35 C34 116.89(18) . . ?
O4 C35 C34 123.4(2) . . ?
O4 C35 N4 119.7(2) . . ?
C26 C36 C30 119.5(2) . . ?
C34 C36 C26 120.83(19) . . ?
C34 C36 C30 119.7(2) . . ?
Cl1 Co2 Cl3 109.00(2) . . ?
Cl2 Co2 Cl1 110.28(3) . . ?
Cl2 Co2 Cl3 111.94(2) . . ?
N3 Co2 Cl1 107.85(5) . . ?
N3 Co2 Cl2 109.79(5) . . ?
N3 Co2 Cl3 107.86(5) . . ?
C19 N3 C23 118.15(19) . . ?
C19 N3 Co2 116.49(14) . . ?
C23 N3 Co2 125.34(15) . . ?
C25 N4 C24 118.32(18) . . ?
C25 N4 C35 124.77(17) . . ?
C35 N4 C24 116.86(17) . . ?
N5 C37 C38 178.4(3) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N6 C39 C40 178.3(3) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

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
O1 H1A Cl1 0.896(16) 2.191(16) 3.0842(16) 175(2) .
O1 H1B O5 0.900(16) 1.916(17) 2.785(2) 162(2) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C1 N1 C5 -0.2(3) . . . . ?
C2 C1 N1 Co1 177.87(16) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 176.37(19) . . . . ?
C3 C4 C5 N1 -2.8(3) . . . . ?
C4 C5 C6 N2 91.7(2) . . . . ?
C4 C5 N1 C1 2.3(3) . . . . ?
C4 C5 N1 Co1 -175.61(15) . . . . ?
C5 C6 N2 C7 -95.6(2) . . . . ?
C5 C6 N2 C17 86.4(2) . . . . ?
C6 C5 N1 C1 -176.89(18) . . . . ?
C6 C5 N1 Co1 5.2(2) . . . . ?
C7 C8 C9 C10 -178.6(2) . . . . ?
C7 C8 C18 C12 177.8(2) . . . . ?
C7 C8 C18 C16 -1.7(3) . . . . ?
C8 C7 N2 C6 -179.02(18) . . . . ?
C8 C7 N2 C17 -1.2(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C8 C18 C12 -0.3(3) . . . . ?
C9 C8 C18 C16 -179.8(2) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 179.2(2) . . . . ?
C10 C11 C12 C18 -0.9(3) . . . . ?
C11 C12 C13 C14 -179.7(2) . . . . ?
C11 C12 C18 C8 1.0(3) . . . . ?
C11 C12 C18 C16 -179.5(2) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C12 C18 C8 -179.1(2) . . . . ?
C13 C12 C18 C16 0.4(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C17 -180.0(2) . . . . ?
C14 C15 C16 C18 0.5(3) . . . . ?
C15 C16 C17 N2 -177.09(19) . . . . ?
C15 C16 C17 O2 1.9(3) . . . . ?
C15 C16 C18 C8 178.6(2) . . . . ?
C15 C16 C18 C12 -0.9(3) . . . . ?
C16 C17 N2 C6 176.47(18) . . . . ?
C16 C17 N2 C7 -1.3(3) . . . . ?
C16 C17 O2 Co1 140.00(19) . . . . ?
C17 C16 C18 C8 -0.9(3) . . . . ?
C17 C16 C18 C12 179.62(19) . . . . ?
C18 C8 C9 C10 -0.5(3) . . . . ?
C18 C12 C13 C14 0.4(3) . . . . ?
C18 C16 C17 N2 2.4(3) . . . . ?
C18 C16 C17 O2 -178.6(2) . . . . ?
N1 C1 C2 C3 -1.3(3) . . . . ?
N1 C5 C6 N2 -89.1(2) . . . . ?
N2 C7 C8 C9 -179.18(19) . . . . ?
N2 C7 C8 C18 2.7(3) . . . . ?
N2 C17 O2 Co1 -41.1(3) . . . . ?
O2 C17 N2 C6 -2.5(3) . . . . ?
O2 C17 N2 C7 179.70(19) . . . . ?
O3 C7 C8 C9 0.7(3) . . . . ?
O3 C7 C8 C18 -177.4(2) . . . . ?
O3 C7 N2 C6 1.1(3) . . . . ?
O3 C7 N2 C17 178.88(19) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C19 N3 C23 0.2(3) . . . . ?
C20 C19 N3 Co2 -178.40(18) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C24 -179.8(2) . . . . ?
C21 C22 C23 N3 0.0(3) . . . . ?
C22 C23 C24 N4 -1.4(3) . . . . ?
C22 C23 N3 C19 -0.1(3) . . . . ?
C22 C23 N3 Co2 178.32(16) . . . . ?
C23 C24 N4 C25 -88.1(2) . . . . ?
C23 C24 N4 C35 89.4(2) . . . . ?
C24 C23 N3 C19 179.61(19) . . . . ?
C24 C23 N3 Co2 -1.9(3) . . . . ?
C25 C26 C27 C28 179.2(2) . . . . ?
C25 C26 C36 C30 -178.6(2) . . . . ?
C25 C26 C36 C34 1.1(3) . . . . ?
C26 C25 N4 C24 177.98(18) . . . . ?
C26 C25 N4 C35 0.7(3) . . . . ?
C26 C27 C28 C29 -0.6(4) . . . . ?
C27 C26 C36 C30 0.8(3) . . . . ?
C27 C26 C36 C34 -179.5(2) . . . . ?
C27 C28 C29 C30 0.8(4) . . . . ?
C28 C29 C30 C31 179.9(2) . . . . ?
C28 C29 C30 C36 -0.2(3) . . . . ?
C29 C30 C31 C32 -178.9(2) . . . . ?
C29 C30 C36 C26 -0.6(3) . . . . ?
C29 C30 C36 C34 179.7(2) . . . . ?
C30 C31 C32 C33 -0.4(4) . . . . ?
C31 C30 C36 C26 179.3(2) . . . . ?
C31 C30 C36 C34 -0.4(3) . . . . ?
C31 C32 C33 C34 -1.3(4) . . . . ?
C32 C33 C34 C35 -177.1(2) . . . . ?
C32 C33 C34 C36 2.1(3) . . . . ?
C33 C34 C35 N4 -179.0(2) . . . . ?
C33 C34 C35 O4 2.5(4) . . . . ?
C33 C34 C36 C26 179.0(2) . . . . ?
C33 C34 C36 C30 -1.3(3) . . . . ?
C34 C35 N4 C24 -178.64(18) . . . . ?
C34 C35 N4 C25 -1.3(3) . . . . ?
C35 C34 C36 C26 -1.7(3) . . . . ?
C35 C34 C36 C30 178.0(2) . . . . ?
C36 C26 C27 C28 -0.2(3) . . . . ?
C36 C30 C31 C32 1.3(4) . . . . ?
C36 C34 C35 N4 1.8(3) . . . . ?
C36 C34 C35 O4 -176.7(2) . . . . ?
N3 C19 C20 C21 -0.1(4) . . . . ?
N3 C23 C24 N4 178.88(18) . . . . ?
N4 C25 C26 C27 -179.93(19) . . . . ?
N4 C25 C26 C36 -0.5(3) . . . . ?
O4 C35 N4 C24 -0.1(3) . . . . ?
O4 C35 N4 C25 177.2(2) . . . . ?
O5 C25 C26 C27 -0.5(3) . . . . ?
O5 C25 C26 C36 178.9(2) . . . . ?
O5 C25 N4 C24 -1.5(3) . . . . ?
O5 C25 N4 C35 -178.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1511752'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H24 Cl2 Mn N4 O4, 2(H2 O)'
_chemical_formula_sum            'C36 H28 Cl2 Mn N4 O6'
_chemical_formula_weight         738.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.8451(4)
_cell_length_b                   9.5894(4)
_cell_length_c                   10.3016(4)
_cell_angle_alpha                77.4960(10)
_cell_angle_beta                 80.6640(10)
_cell_angle_gamma                64.1630(10)
_cell_volume                     765.48(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0336 before and 0.0262 after correction.
The Ratio of minimum to maximum transmission is 0.9265.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             379
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5680
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.031
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2940
_reflns_number_total             3524
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.5460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0760
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O3-H3A = O3-H3B
 0.95 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C14(H14), C15(H15), C2(H2), C11(H11), C13(H13), C3(H3),
 C4(H4), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.5000 0.5000 0.0000 0.01026(9) Uani 1 2 d S T P . .
Cl1 Cl 0.79275(5) 0.29174(5) -0.01000(4) 0.01764(10) Uani 1 1 d . . . . .
O1 O 0.50726(15) 0.50302(13) 0.21438(11) 0.0134(2) Uani 1 1 d . . . . .
O2 O 0.32972(16) 0.14778(14) 0.47617(12) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.42525(17) 0.32329(15) 0.35071(13) 0.0107(3) Uani 1 1 d . . . . .
O3 O -0.0513(2) 0.96038(17) 0.19441(15) 0.0298(3) Uani 1 1 d D . . . .
H3A H 0.039(3) 0.889(3) 0.140(2) 0.045 Uiso 1 1 d DR . . . .
H3B H -0.093(3) 1.055(2) 0.128(2) 0.045 Uiso 1 1 d DR . . . .
N1 N 0.39805(17) 0.30941(16) 0.06103(14) 0.0121(3) Uani 1 1 d . . . . .
C6 C 0.5375(2) 0.20158(18) 0.26963(16) 0.0120(3) Uani 1 1 d . . . . .
H6A H 0.5850 0.0986 0.3284 0.014 Uiso 1 1 calc R . . . .
H6B H 0.6321 0.2275 0.2252 0.014 Uiso 1 1 calc R . . . .
C5 C 0.4419(2) 0.19102(19) 0.16541(16) 0.0112(3) Uani 1 1 d . . . . .
C16 C 0.2204(2) 0.39782(19) 0.54338(16) 0.0118(3) Uani 1 1 d . . . . .
C12 C 0.1292(2) 0.65928(19) 0.60109(16) 0.0131(3) Uani 1 1 d . . . . .
C17 C 0.3248(2) 0.27954(19) 0.45831(16) 0.0121(3) Uani 1 1 d . . . . .
C1 C 0.3044(2) 0.3049(2) -0.02763(17) 0.0154(3) Uani 1 1 d . . . . .
H1 H 0.2704 0.3886 -0.1006 0.018 Uiso 1 1 calc R . . . .
C8 C 0.3263(2) 0.58529(19) 0.40552(16) 0.0112(3) Uani 1 1 d . . . . .
C7 C 0.4249(2) 0.47130(19) 0.31610(16) 0.0110(3) Uani 1 1 d . . . . .
C18 C 0.2267(2) 0.54674(19) 0.51641(16) 0.0112(3) Uani 1 1 d . . . . .
C9 C 0.3305(2) 0.73147(19) 0.37959(17) 0.0135(3) Uani 1 1 d . . . . .
H9 H 0.3961 0.7574 0.3038 0.016 Uiso 1 1 calc R . . . .
C14 C 0.0177(2) 0.4766(2) 0.73082(17) 0.0161(3) Uani 1 1 d . . . . .
H14 H -0.0549 0.4533 0.8021 0.019 Uiso 1 1 calc R . . . .
C15 C 0.1166(2) 0.3639(2) 0.64801(17) 0.0144(3) Uani 1 1 d . . . . .
H15 H 0.1115 0.2646 0.6645 0.017 Uiso 1 1 calc R . . . .
C2 C 0.2552(2) 0.1839(2) -0.01733(18) 0.0165(3) Uani 1 1 d . . . . .
H2 H 0.1883 0.1856 -0.0816 0.020 Uiso 1 1 calc R . . . .
C11 C 0.1396(2) 0.8066(2) 0.57313(17) 0.0150(3) Uani 1 1 d . . . . .
H11 H 0.0777 0.8821 0.6301 0.018 Uiso 1 1 calc R . . . .
C13 C 0.0258(2) 0.6201(2) 0.70883(17) 0.0154(3) Uani 1 1 d . . . . .
H13 H -0.0389 0.6938 0.7668 0.019 Uiso 1 1 calc R . . . .
C3 C 0.3050(2) 0.0605(2) 0.08779(18) 0.0159(3) Uani 1 1 d . . . . .
H3 H 0.2758 -0.0255 0.0959 0.019 Uiso 1 1 calc R . . . .
C4 C 0.3986(2) 0.06532(19) 0.18111(17) 0.0143(3) Uani 1 1 d . . . . .
H4 H 0.4327 -0.0169 0.2553 0.017 Uiso 1 1 calc R . . . .
C10 C 0.2379(2) 0.8415(2) 0.46497(18) 0.0162(3) Uani 1 1 d . . . . .
H10 H 0.2434 0.9407 0.4478 0.019 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 Cl1 2.4898(4) 2_665 ?
Mn1 Cl1 2.4898(4) . ?
Mn1 O1 2.2266(11) 2_665 ?
Mn1 O1 2.2266(11) . ?
Mn1 N1 2.3030(13) . ?
Mn1 N1 2.3030(13) 2_665 ?
O1 C7 1.236(2) . ?
O2 C17 1.219(2) . ?
N2 C6 1.479(2) . ?
N2 C17 1.413(2) . ?
N2 C7 1.385(2) . ?
O3 H3A 0.979(17) . ?
O3 H3B 0.977(17) . ?
N1 C5 1.349(2) . ?
N1 C1 1.348(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.514(2) . ?
C5 C4 1.387(2) . ?
C16 C17 1.470(2) . ?
C16 C18 1.419(2) . ?
C16 C15 1.378(2) . ?
C12 C18 1.422(2) . ?
C12 C11 1.420(2) . ?
C12 C13 1.414(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C8 C7 1.466(2) . ?
C8 C18 1.411(2) . ?
C8 C9 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.405(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.412(2) . ?
C14 C13 1.377(2) . ?
C15 H15 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.374(2) . ?
C13 H13 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C10 H10 0.9500 . ?

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
Cl1 Mn1 Cl1 180.0 2_665 . ?
O1 Mn1 Cl1 88.23(3) 2_665 . ?
O1 Mn1 Cl1 91.77(3) . . ?
O1 Mn1 Cl1 91.77(3) 2_665 2_665 ?
O1 Mn1 Cl1 88.23(3) . 2_665 ?
O1 Mn1 O1 180.0 2_665 . ?
O1 Mn1 N1 90.32(4) 2_665 . ?
O1 Mn1 N1 90.32(4) . 2_665 ?
O1 Mn1 N1 89.68(4) 2_665 2_665 ?
O1 Mn1 N1 89.68(4) . . ?
N1 Mn1 Cl1 89.79(4) . . ?
N1 Mn1 Cl1 89.79(4) 2_665 2_665 ?
N1 Mn1 Cl1 90.21(4) . 2_665 ?
N1 Mn1 Cl1 90.21(4) 2_665 . ?
N1 Mn1 N1 180.0 . 2_665 ?
C7 O1 Mn1 132.29(11) . . ?
C17 N2 C6 117.11(13) . . ?
C7 N2 C6 118.24(13) . . ?
C7 N2 C17 124.65(13) . . ?
H3A O3 H3B 100(2) . . ?
C5 N1 Mn1 126.33(11) . . ?
C1 N1 Mn1 115.47(11) . . ?
C1 N1 C5 117.50(14) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 C5 110.74(13) . . ?
H6A C6 H6B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
N1 C5 C6 117.45(14) . . ?
N1 C5 C4 122.39(15) . . ?
C4 C5 C6 120.13(15) . . ?
C18 C16 C17 119.58(14) . . ?
C15 C16 C17 119.96(15) . . ?
C15 C16 C18 120.46(15) . . ?
C11 C12 C18 118.37(15) . . ?
C13 C12 C18 118.73(15) . . ?
C13 C12 C11 122.90(15) . . ?
O2 C17 N2 119.10(15) . . ?
O2 C17 C16 123.82(15) . . ?
N2 C17 C16 117.08(14) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.12(16) . . ?
C2 C1 H1 118.4 . . ?
C18 C8 C7 120.21(14) . . ?
C9 C8 C7 119.45(15) . . ?
C9 C8 C18 120.33(15) . . ?
O1 C7 N2 120.39(14) . . ?
O1 C7 C8 122.26(14) . . ?
N2 C7 C8 117.35(14) . . ?
C16 C18 C12 119.46(15) . . ?
C8 C18 C16 120.83(15) . . ?
C8 C18 C12 119.70(15) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.19(16) . . ?
C10 C9 H9 119.9 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.39(16) . . ?
C16 C15 C14 120.06(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.03(16) . . ?
C3 C2 H2 120.5 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 120.99(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.85(15) . . ?
C14 C13 H13 119.6 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.41(15) . . ?
C4 C3 H3 120.8 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.51(16) . . ?
C3 C4 H4 120.2 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.38(15) . . ?
C11 C10 H10 119.8 . . ?

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
O3 H3A Cl1 0.979(17) 2.266(17) 3.2317(15) 169(2) 2_665
O3 H3B Cl1 0.977(17) 2.291(17) 3.2647(16) 174(2) 1_465

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
Mn1 O1 C7 N2 59.0(2) . . . . ?
Mn1 O1 C7 C8 -122.03(14) . . . . ?
Mn1 N1 C5 C6 14.0(2) . . . . ?
Mn1 N1 C5 C4 -167.88(12) . . . . ?
Mn1 N1 C1 C2 169.66(13) . . . . ?
N2 C6 C5 N1 72.29(18) . . . . ?
N2 C6 C5 C4 -105.91(17) . . . . ?
N1 C5 C4 C3 -0.8(2) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
C6 N2 C17 O2 -2.9(2) . . . . ?
C6 N2 C17 C16 176.68(14) . . . . ?
C6 N2 C7 O1 5.2(2) . . . . ?
C6 N2 C7 C8 -173.87(14) . . . . ?
C6 C5 C4 C3 177.31(15) . . . . ?
C5 N1 C1 C2 -1.3(2) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C17 N2 C6 C5 82.96(17) . . . . ?
C17 N2 C7 O1 -174.48(15) . . . . ?
C17 N2 C7 C8 6.5(2) . . . . ?
C17 C16 C18 C12 -178.22(14) . . . . ?
C17 C16 C18 C8 2.8(2) . . . . ?
C17 C16 C15 C14 179.24(15) . . . . ?
C1 N1 C5 C6 -176.14(14) . . . . ?
C1 N1 C5 C4 2.0(2) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . . ?
C7 N2 C6 C5 -96.73(16) . . . . ?
C7 N2 C17 O2 176.78(15) . . . . ?
C7 N2 C17 C16 -3.7(2) . . . . ?
C7 C8 C18 C16 0.1(2) . . . . ?
C7 C8 C18 C12 -178.89(14) . . . . ?
C7 C8 C9 C10 -179.40(15) . . . . ?
C18 C16 C17 O2 178.36(16) . . . . ?
C18 C16 C17 N2 -1.2(2) . . . . ?
C18 C16 C15 C14 -1.1(2) . . . . ?
C18 C12 C11 C10 1.7(2) . . . . ?
C18 C12 C13 C14 -0.8(2) . . . . ?
C18 C8 C7 O1 176.41(15) . . . . ?
C18 C8 C7 N2 -4.6(2) . . . . ?
C18 C8 C9 C10 1.2(2) . . . . ?
C9 C8 C7 O1 -3.0(2) . . . . ?
C9 C8 C7 N2 176.02(14) . . . . ?
C9 C8 C18 C16 179.51(15) . . . . ?
C9 C8 C18 C12 0.5(2) . . . . ?
C15 C16 C17 O2 -2.0(3) . . . . ?
C15 C16 C17 N2 178.46(15) . . . . ?
C15 C16 C18 C12 2.1(2) . . . . ?
C15 C16 C18 C8 -176.84(15) . . . . ?
C15 C14 C13 C12 1.8(3) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C11 C12 C18 C16 179.08(15) . . . . ?
C11 C12 C18 C8 -1.9(2) . . . . ?
C11 C12 C13 C14 178.94(16) . . . . ?
C13 C12 C18 C16 -1.2(2) . . . . ?
C13 C12 C18 C8 177.80(15) . . . . ?
C13 C12 C11 C10 -178.03(16) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L1
_database_code_depnum_ccdc_archive 'CCDC 1511748'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 N2 O2'
_chemical_formula_sum            'C18 H12 N2 O2'
_chemical_formula_weight         288.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1815(6)
_cell_length_b                   14.4232(8)
_cell_length_c                   10.1911(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.965(2)
_cell_angle_gamma                90
_cell_volume                     1346.34(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      2.451
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0395 before and 0.0359 after correction.
The Ratio of minimum to maximum transmission is 0.8865.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10516
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_min         2.223
_diffrn_ambient_temperature      99.96
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2281
_reflns_number_total             3089
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.4510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.95026(17) 0.17318(10) 0.43851(14) 0.0238(3) Uani 1 1 d . . . . .
H1 H 0.9771 0.1777 0.3504 0.029 Uiso 1 1 calc R . . . .
C2 C 1.02608(17) 0.11210(10) 0.52136(15) 0.0238(3) Uani 1 1 d . . . . .
H2 H 1.1042 0.0765 0.4913 0.029 Uiso 1 1 calc R . . . .
C3 C 0.98629(18) 0.10337(10) 0.64994(15) 0.0243(3) Uani 1 1 d . . . . .
H3 H 1.0352 0.0610 0.7091 0.029 Uiso 1 1 calc R . . . .
C4 C 0.87315(17) 0.15828(10) 0.68955(14) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.8432 0.1541 0.7767 0.025 Uiso 1 1 calc R . . . .
C5 C 0.80431(16) 0.21939(9) 0.59989(14) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.68103(16) 0.28080(9) 0.64099(14) 0.0189(3) Uani 1 1 d . . . . .
H6A H 0.5906 0.2436 0.6430 0.023 Uiso 1 1 calc R . . . .
H6B H 0.7057 0.3048 0.7308 0.023 Uiso 1 1 calc R . . . .
C7 C 0.75720(16) 0.43106(9) 0.56067(13) 0.0170(3) Uani 1 1 d . . . . .
C8 C 0.74236(15) 0.50507(9) 0.46009(13) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.83812(16) 0.57867(10) 0.46584(14) 0.0202(3) Uani 1 1 d . . . . .
H9 H 0.9130 0.5818 0.5348 0.024 Uiso 1 1 calc R . . . .
C10 C 0.82593(17) 0.64931(10) 0.37026(15) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.8927 0.6997 0.3750 0.027 Uiso 1 1 calc R . . . .
C11 C 0.71807(17) 0.64567(10) 0.27030(14) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.7109 0.6937 0.2064 0.025 Uiso 1 1 calc R . . . .
C12 C 0.61729(16) 0.57120(10) 0.26113(14) 0.0182(3) Uani 1 1 d . . . . .
C13 C 0.50324(17) 0.56532(10) 0.16075(14) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.4926 0.6126 0.0959 0.025 Uiso 1 1 calc R . . . .
C14 C 0.40784(17) 0.49197(10) 0.15608(14) 0.0234(3) Uani 1 1 d . . . . .
H14 H 0.3314 0.4892 0.0884 0.028 Uiso 1 1 calc R . . . .
C15 C 0.42212(17) 0.42081(10) 0.25058(14) 0.0210(3) Uani 1 1 d . . . . .
H15 H 0.3560 0.3701 0.2458 0.025 Uiso 1 1 calc R . . . .
C16 C 0.53181(16) 0.42450(9) 0.35010(13) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.54595(16) 0.34919(9) 0.44892(13) 0.0177(3) Uani 1 1 d . . . . .
C18 C 0.63059(15) 0.49970(9) 0.35756(13) 0.0162(3) Uani 1 1 d . . . . .
N1 N 0.84023(14) 0.22687(8) 0.47517(12) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.65561(13) 0.35885(8) 0.54994(11) 0.0170(3) Uani 1 1 d . . . . .
O1 O 0.85321(11) 0.43072(7) 0.64960(10) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.46590(12) 0.28135(7) 0.44435(10) 0.0240(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.376(2) . ?
C1 N1 1.3462(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 C6 1.519(2) . ?
C5 N1 1.3394(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 N2 1.4672(17) . ?
C7 C8 1.4797(19) . ?
C7 N2 1.3974(18) . ?
C7 O1 1.2198(18) . ?
C8 C9 1.377(2) . ?
C8 C18 1.415(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.409(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.372(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.416(2) . ?
C12 C13 1.415(2) . ?
C12 C18 1.4239(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.372(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.407(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(2) . ?
C16 C17 1.4809(19) . ?
C16 C18 1.4126(19) . ?
C17 N2 1.3963(18) . ?
C17 O2 1.2227(17) . ?

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 C1 H1 118.1 . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.76(13) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.80(14) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.24(14) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.08(13) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 120.15(12) . . ?
N1 C5 C4 122.98(13) . . ?
N1 C5 C6 116.86(12) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N2 C6 C5 111.22(11) . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
N2 C7 C8 117.03(12) . . ?
O1 C7 C8 123.01(13) . . ?
O1 C7 N2 119.96(12) . . ?
C9 C8 C7 119.92(13) . . ?
C9 C8 C18 120.12(13) . . ?
C18 C8 C7 119.96(12) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.54(14) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.30(14) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.85(13) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C18 118.63(14) . . ?
C13 C12 C11 122.72(13) . . ?
C13 C12 C18 118.65(13) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.66(13) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.63(14) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.23(14) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.78(13) . . ?
C15 C16 C18 120.16(13) . . ?
C18 C16 C17 120.06(13) . . ?
N2 C17 C16 116.94(12) . . ?
O2 C17 C16 122.47(14) . . ?
O2 C17 N2 120.59(13) . . ?
C8 C18 C12 119.55(13) . . ?
C16 C18 C8 120.79(12) . . ?
C16 C18 C12 119.66(13) . . ?
C5 N1 C1 117.11(13) . . ?
C7 N2 C6 116.50(12) . . ?
C17 N2 C6 117.69(11) . . ?
C17 N2 C7 125.14(11) . . ?

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
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C1 N1 C5 0.1(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -179.52(14) . . . . ?
C3 C4 C5 N1 1.2(2) . . . . ?
C4 C5 C6 N2 161.81(13) . . . . ?
C4 C5 N1 C1 -1.3(2) . . . . ?
C5 C6 N2 C7 -75.32(15) . . . . ?
C5 C6 N2 C17 95.80(14) . . . . ?
C6 C5 N1 C1 179.45(13) . . . . ?
C7 C8 C9 C10 179.57(12) . . . . ?
C7 C8 C18 C12 -179.93(12) . . . . ?
C7 C8 C18 C16 0.34(19) . . . . ?
C8 C7 N2 C6 173.36(11) . . . . ?
C8 C7 N2 C17 2.99(18) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C8 C18 C12 -0.46(19) . . . . ?
C9 C8 C18 C16 179.80(12) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 179.13(13) . . . . ?
C10 C11 C12 C18 -0.3(2) . . . . ?
C11 C12 C13 C14 -179.78(13) . . . . ?
C11 C12 C18 C8 0.57(19) . . . . ?
C11 C12 C18 C16 -179.69(12) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C12 C18 C8 -178.92(12) . . . . ?
C13 C12 C18 C16 0.82(19) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C17 -179.92(13) . . . . ?
C14 C15 C16 C18 -0.1(2) . . . . ?
C15 C16 C17 N2 -177.59(12) . . . . ?
C15 C16 C17 O2 2.1(2) . . . . ?
C15 C16 C18 C8 179.12(12) . . . . ?
C15 C16 C18 C12 -0.62(19) . . . . ?
C16 C17 N2 C6 -173.95(11) . . . . ?
C16 C17 N2 C7 -3.68(18) . . . . ?
C17 C16 C18 C8 -1.06(19) . . . . ?
C17 C16 C18 C12 179.20(12) . . . . ?
C18 C8 C9 C10 0.1(2) . . . . ?
C18 C12 C13 C14 -0.31(19) . . . . ?
C18 C16 C17 N2 2.59(18) . . . . ?
C18 C16 C17 O2 -177.77(12) . . . . ?
N1 C1 C2 C3 1.2(2) . . . . ?
N1 C5 C6 N2 -18.91(18) . . . . ?
N2 C7 C8 C9 179.37(12) . . . . ?
N2 C7 C8 C18 -1.17(18) . . . . ?
O1 C7 C8 C9 -1.2(2) . . . . ?
O1 C7 C8 C18 178.29(12) . . . . ?
O1 C7 N2 C6 -6.12(18) . . . . ?
O1 C7 N2 C17 -176.49(12) . . . . ?
O2 C17 N2 C6 6.41(18) . . . . ?
O2 C17 N2 C7 176.68(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L2
_database_code_depnum_ccdc_archive 'CCDC 1511749'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H11 N3 O4'
_chemical_formula_sum            'C18 H11 N3 O4'
_chemical_formula_weight         333.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.4265(6)
_cell_length_b                   11.5416(5)
_cell_length_c                   17.5201(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2917.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.542
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0690 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.8931.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24473
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.914
_diffrn_reflns_theta_min         2.325
_diffrn_ambient_temperature      100.03
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2356
_reflns_number_total             3485
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+2.7100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C21-C16
 1.375 with sigma of 0.01
 C21-C20
 1.375 with sigma of 0.01
 C15-C14
 1.375 with sigma of 0.01
 C15-C16
 1.375 with sigma of 0.01
 C21-O1
 2.8 with sigma of 0.02
 C20-C19
 1.375 with sigma of 0.01
 C19-C12
 1.375 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) = Uanis(C20)
Uanis(C15) = Uanis(C21)
Uanis(C13) = Uanis(C19)
4. Rigid body (RIGU) restrains
 C12, C13, C14, N4, O6, O5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O4(0.8) O3(0.8) H11(0.2) C15(0.8) H15(0.8) N3(0.8) C13(0.8)
 H13(0.8) C14(0.8) H14(0.8) O5(0.2) O6(0.2) N4(0.2) C19(0.2) C20(0.2) H20(0.2)
 C21(0.2) H21(0.2)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3), C1(H1), C9(H9), C11(H11), C10(H10), C15(H15),
 C13(H13), C14(H14), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.50614(12) 0.64003(16) 0.31144(11) 0.0339(4) Uani 1 1 d . . . . .
O1 O 0.68766(13) 0.6157(2) 0.52179(11) 0.0461(6) Uani 1 1 d D . . . .
N2 N 0.59392(13) 0.62916(18) 0.41847(11) 0.0255(5) Uani 1 1 d . . . . .
N1 N 0.73896(13) 0.68056(17) 0.32519(12) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.83300(15) 0.8089(2) 0.24989(13) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.8810 0.8183 0.2133 0.027 Uiso 1 1 calc R . . . .
C8 C 0.51459(14) 0.4561(2) 0.37081(13) 0.0206(5) Uani 1 1 d . . . . .
C18 C 0.55828(14) 0.3885(2) 0.42754(13) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.53655(15) 0.5809(2) 0.36310(14) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.71805(15) 0.8859(2) 0.33323(13) 0.0223(5) Uani 1 1 d . . . . .
H4 H 0.6863 0.9498 0.3554 0.027 Uiso 1 1 calc R . . . .
C3 C 0.78748(15) 0.9038(2) 0.28006(14) 0.0232(5) Uani 1 1 d . . . . .
H3 H 0.8036 0.9801 0.2645 0.028 Uiso 1 1 calc R . . . .
C5 C 0.69541(15) 0.7728(2) 0.35377(13) 0.0220(5) Uani 1 1 d . . . . .
C16 C 0.61933(14) 0.4412(2) 0.47994(13) 0.0251(5) Uani 1 1 d D . . . .
C12 C 0.54142(16) 0.2664(2) 0.43183(15) 0.0285(5) Uani 1 1 d D U . . .
C1 C 0.80688(15) 0.6999(2) 0.27441(14) 0.0253(5) Uani 1 1 d . . . . .
H1 H 0.8389 0.6349 0.2541 0.030 Uiso 1 1 calc R . . . .
O4 O 0.51596(17) 0.0271(2) 0.38105(17) 0.0472(7) Uani 0.8 1 d . . P A 1
O3 O 0.37088(17) 0.0701(2) 0.36384(16) 0.0472(7) Uani 0.8 1 d . . P A 1
C9 C 0.45198(15) 0.4066(2) 0.32138(14) 0.0276(5) Uani 1 1 d . . . . .
H9 H 0.4228 0.4530 0.2836 0.033 Uiso 1 1 calc R . . . .
C11 C 0.47596(17) 0.2219(2) 0.37817(17) 0.0337(6) Uani 1 1 d . . . . .
H11 H 0.4632 0.1411 0.3788 0.040 Uiso 0.2 1 calc R . P B 2
C17 C 0.63790(15) 0.5669(2) 0.47646(14) 0.0279(6) Uani 1 1 d . . . . .
C10 C 0.43096(17) 0.2890(2) 0.32620(16) 0.0332(6) Uani 1 1 d . . . . .
H10 H 0.3856 0.2559 0.2935 0.040 Uiso 1 1 calc R . . . .
C6 C 0.61779(17) 0.7522(2) 0.41030(16) 0.0330(6) Uani 1 1 d . . . . .
H6A H 0.6365 0.7831 0.4607 0.040 Uiso 1 1 calc R . . . .
H6B H 0.5621 0.7954 0.3934 0.040 Uiso 1 1 calc R . . . .
C15 C 0.6603(17) 0.3729(7) 0.5352(12) 0.0357(12) Uani 0.8 1 d D . P C 1
H15 H 0.7010 0.4071 0.5714 0.043 Uiso 0.8 1 calc R . P C 1
N3 N 0.45224(19) 0.0974(2) 0.37423(17) 0.0350(7) Uani 0.8 1 d . . P A 1
C13 C 0.5848(9) 0.2006(8) 0.4878(6) 0.0371(12) Uani 0.8 1 d . U P C 1
H13 H 0.5741 0.1195 0.4907 0.045 Uiso 0.8 1 calc R . P C 1
C14 C 0.6424(8) 0.2529(6) 0.5384(6) 0.0387(10) Uani 0.8 1 d D U P C 1
H14 H 0.6715 0.2075 0.5768 0.046 Uiso 0.8 1 calc R . P C 1
O5 O 0.5980(7) 0.0281(8) 0.4684(6) 0.040(2) Uani 0.2 1 d . U P C 2
O6 O 0.6002(7) 0.0643(9) 0.5866(6) 0.045(2) Uani 0.2 1 d . U P C 2
N4 N 0.5991(8) 0.0951(10) 0.5181(7) 0.036(2) Uani 0.2 1 d . U P C 2
C19 C 0.593(4) 0.214(3) 0.494(3) 0.0371(12) Uani 0.2 1 d D . P C 2
C20 C 0.653(3) 0.268(2) 0.545(3) 0.0387(10) Uani 0.2 1 d D . P C 2
H20 H 0.6825 0.2260 0.5840 0.046 Uiso 0.2 1 calc R . P C 2
C21 C 0.668(7) 0.384(2) 0.536(5) 0.0357(12) Uani 0.2 1 d D . P C 2
H21 H 0.7101 0.4239 0.5684 0.043 Uiso 0.2 1 calc R . P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C7 1.215(3) . ?
O1 C17 1.210(3) . ?
N2 C7 1.391(3) . ?
N2 C17 1.397(3) . ?
N2 C6 1.468(3) . ?
N1 C5 1.334(3) . ?
N1 C1 1.342(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C2 C1 1.381(3) . ?
C8 C18 1.412(3) . ?
C8 C7 1.482(3) . ?
C8 C9 1.375(3) . ?
C18 C16 1.410(3) . ?
C18 C12 1.432(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(3) . ?
C4 C5 1.393(3) . ?
C3 H3 0.9500 . ?
C5 C6 1.514(3) . ?
C16 C17 1.477(4) . ?
C16 C15 1.382(5) . ?
C16 C21 1.379(10) . ?
C12 C11 1.428(4) . ?
C12 C13 1.389(6) . ?
C12 C19 1.458(19) . ?
C1 H1 0.9500 . ?
O4 N3 1.232(4) . ?
O3 N3 1.229(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.360(4) . ?
C11 N3 1.478(4) . ?
C10 H10 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C14 1.410(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.357(6) . ?
C14 H14 0.9500 . ?
O5 N4 1.164(14) . ?
O6 N4 1.252(15) . ?
N4 C19 1.43(4) . ?
C19 C20 1.383(10) . ?
C20 H20 0.9500 . ?
C20 C21 1.359(10) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 C17 124.9(2) . . ?
C7 N2 C6 117.3(2) . . ?
C17 N2 C6 117.5(2) . . ?
C5 N1 C1 117.4(2) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(2) . . ?
C18 C8 C7 120.4(2) . . ?
C9 C8 C18 120.5(2) . . ?
C9 C8 C7 119.1(2) . . ?
C8 C18 C12 120.3(2) . . ?
C16 C18 C8 119.9(2) . . ?
C16 C18 C12 119.8(2) . . ?
O2 C7 N2 120.6(2) . . ?
O2 C7 C8 122.5(2) . . ?
N2 C7 C8 116.9(2) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.9(2) . . ?
C5 C4 H4 120.5 . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N1 C5 C4 122.7(2) . . ?
N1 C5 C6 117.9(2) . . ?
C4 C5 C6 119.3(2) . . ?
C18 C16 C17 120.7(2) . . ?
C15 C16 C18 118.5(3) . . ?
C15 C16 C17 120.8(3) . . ?
C21 C16 C18 125.1(10) . . ?
C21 C16 C17 114.1(10) . . ?
C18 C12 C19 111.4(16) . . ?
C11 C12 C18 115.6(2) . . ?
C11 C12 C19 133.0(16) . . ?
C13 C12 C18 119.9(4) . . ?
C13 C12 C11 124.5(4) . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C12 C11 H11 118.3 . . ?
C12 C11 N3 122.2(3) . . ?
C10 C11 C12 123.5(2) . . ?
C10 C11 H11 118.3 . . ?
C10 C11 N3 114.3(3) . . ?
O1 C17 N2 120.5(3) . . ?
O1 C17 C16 122.5(2) . . ?
N2 C17 C16 116.9(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
N2 C6 C5 112.9(2) . . ?
N2 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.7(6) . . ?
C14 C15 H15 119.7 . . ?
O4 N3 C11 117.6(3) . . ?
O3 N3 O4 124.0(3) . . ?
O3 N3 C11 118.5(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(8) . . ?
C14 C13 H13 120.2 . . ?
C15 C14 H14 119.2 . . ?
C13 C14 C15 121.5(8) . . ?
C13 C14 H14 119.2 . . ?
O5 N4 O6 121.9(12) . . ?
O5 N4 C19 115(2) . . ?
O6 N4 C19 123(2) . . ?
N4 C19 C12 130(3) . . ?
C20 C19 C12 127(3) . . ?
C20 C19 N4 102.4(15) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 119(3) . . ?
C21 C20 H20 120.6 . . ?
C16 C21 H21 121.1 . . ?
C20 C21 C16 118(2) . . ?
C20 C21 H21 121.1 . . ?

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
N1 C5 C6 N2 -7.1(3) . . . . ?
C8 C18 C16 C17 0.3(3) . . . . ?
C8 C18 C16 C15 179.4(16) . . . . ?
C8 C18 C16 C21 -178(7) . . . . ?
C8 C18 C12 C11 -2.7(3) . . . . ?
C8 C18 C12 C13 180.0(8) . . . . ?
C8 C18 C12 C19 -180(3) . . . . ?
C8 C9 C10 C11 -2.9(4) . . . . ?
C18 C8 C7 O2 174.1(2) . . . . ?
C18 C8 C7 N2 -6.3(3) . . . . ?
C18 C8 C9 C10 -0.3(3) . . . . ?
C18 C16 C17 O1 177.8(2) . . . . ?
C18 C16 C17 N2 -1.3(3) . . . . ?
C18 C16 C15 C14 1(3) . . . . ?
C18 C16 C21 C20 -3(14) . . . . ?
C18 C12 C11 C10 -0.5(3) . . . . ?
C18 C12 C11 N3 178.8(2) . . . . ?
C18 C12 C13 C14 0.4(12) . . . . ?
C18 C12 C19 N4 -178(5) . . . . ?
C18 C12 C19 C20 -1(5) . . . . ?
C7 N2 C17 O1 179.1(2) . . . . ?
C7 N2 C17 C16 -1.9(3) . . . . ?
C7 N2 C6 C5 -80.7(3) . . . . ?
C7 C8 C18 C16 3.5(3) . . . . ?
C7 C8 C18 C12 -176.0(2) . . . . ?
C7 C8 C9 C10 178.9(2) . . . . ?
C4 C5 C6 N2 172.4(2) . . . . ?
C3 C2 C1 N1 0.9(4) . . . . ?
C3 C4 C5 N1 1.1(3) . . . . ?
C3 C4 C5 C6 -178.4(2) . . . . ?
C5 N1 C1 C2 -0.7(4) . . . . ?
C5 C4 C3 C2 -0.9(3) . . . . ?
C16 C18 C12 C11 177.8(2) . . . . ?
C16 C18 C12 C13 0.4(8) . . . . ?
C16 C18 C12 C19 0(3) . . . . ?
C16 C15 C14 C13 0(3) . . . . ?
C12 C18 C16 C17 179.9(2) . . . . ?
C12 C18 C16 C15 -1.0(16) . . . . ?
C12 C18 C16 C21 1(7) . . . . ?
C12 C11 C10 C9 3.3(4) . . . . ?
C12 C11 N3 O4 -40.9(4) . . . . ?
C12 C11 N3 O3 139.7(3) . . . . ?
C12 C13 C14 C15 -0.6(19) . . . . ?
C12 C19 C20 C21 -1(8) . . . . ?
C1 N1 C5 C4 -0.3(3) . . . . ?
C1 N1 C5 C6 179.2(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C9 C8 C18 C16 -177.3(2) . . . . ?
C9 C8 C18 C12 3.1(3) . . . . ?
C9 C8 C7 O2 -5.1(3) . . . . ?
C9 C8 C7 N2 174.5(2) . . . . ?
C11 C12 C13 C14 -176.7(6) . . . . ?
C11 C12 C19 N4 5(8) . . . . ?
C11 C12 C19 C20 -177(2) . . . . ?
C17 N2 C7 O2 -174.8(2) . . . . ?
C17 N2 C7 C8 5.5(3) . . . . ?
C17 N2 C6 C5 92.9(3) . . . . ?
C17 C16 C15 C14 180.0(17) . . . . ?
C17 C16 C21 C20 178(8) . . . . ?
C10 C11 N3 O4 138.5(3) . . . . ?
C10 C11 N3 O3 -40.9(4) . . . . ?
C6 N2 C7 O2 -1.8(3) . . . . ?
C6 N2 C7 C8 178.62(19) . . . . ?
C6 N2 C17 O1 6.0(3) . . . . ?
C6 N2 C17 C16 -174.96(19) . . . . ?
C15 C16 C17 O1 -1.3(16) . . . . ?
C15 C16 C17 N2 179.7(16) . . . . ?
N3 C11 C10 C9 -176.1(2) . . . . ?
C13 C12 C11 C10 176.7(8) . . . . ?
C13 C12 C11 N3 -3.9(9) . . . . ?
O5 N4 C19 C12 36(7) . . . . ?
O5 N4 C19 C20 -142(2) . . . . ?
O6 N4 C19 C12 -140(4) . . . . ?
O6 N4 C19 C20 42(4) . . . . ?
N4 C19 C20 C21 177(8) . . . . ?
C19 C12 C11 C10 176(4) . . . . ?
C19 C20 C21 C16 3(13) . . . . ?
C21 C16 C17 O1 -4(6) . . . . ?
C21 C16 C17 N2 177(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_L3
_database_code_depnum_ccdc_archive 'CCDC 1511750'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.23 svn.r3337 for OlexSys, GUI svn.r5217)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 N2 O2'
_chemical_formula_sum            'C18 H12 N2 O2'
_chemical_formula_weight         288.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

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

_cell_length_a                   8.2040(3)
_cell_length_b                   9.0699(3)
_cell_length_c                   9.5149(4)
_cell_angle_alpha                80.777(2)
_cell_angle_beta                 79.653(2)
_cell_angle_gamma                71.835(2)
_cell_volume                     657.64(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3055
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.159
_cell_measurement_theta_min      4.754
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.8344.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7989
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.352
_diffrn_reflns_theta_min         4.754
_diffrn_ambient_temperature      99.97
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1956
_reflns_number_total             2390
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.35A (2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1350
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.98655(14) 0.25391(12) 0.47905(11) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.76606(15) 0.51723(12) 0.87136(11) 0.0318(3) Uani 1 1 d . . . . .
N1 N 0.72394(17) 0.03880(15) 1.02102(13) 0.0282(3) Uani 1 1 d . . . . .
N2 N 0.87587(15) 0.38631(14) 0.67458(12) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.74480(19) -0.08270(17) 0.94876(15) 0.0272(3) Uani 1 1 d . . . . .
H1 H 0.6865 -0.1581 0.9905 0.033 Uiso 1 1 calc R . . . .
C2 C 0.84664(19) -0.10415(16) 0.81683(16) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.8585 -0.1927 0.7701 0.031 Uiso 1 1 calc R . . . .
C3 C 0.93091(18) 0.00543(16) 0.75407(14) 0.0245(3) Uani 1 1 d . . . . .
H3 H 1.0016 -0.0068 0.6635 0.029 Uiso 1 1 calc R . . . .
C4 C 0.91079(17) 0.13397(16) 0.82537(14) 0.0233(3) Uani 1 1 d . . . . .
C5 C 0.80706(19) 0.14293(16) 0.95890(15) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.7947 0.2291 1.0091 0.031 Uiso 1 1 calc R . . . .
C6 C 0.99275(19) 0.26186(16) 0.76077(15) 0.0255(3) Uani 1 1 d . . . . .
H6A H 1.0201 0.3068 0.8387 0.031 Uiso 1 1 calc R . . . .
H6B H 1.1026 0.2171 0.6990 0.031 Uiso 1 1 calc R . . . .
C7 C 0.88245(18) 0.36736(16) 0.53015(15) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.75943(18) 0.48897(16) 0.44658(15) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.75824(19) 0.47631(17) 0.30411(15) 0.0258(3) Uani 1 1 d . . . . .
H9 H 0.8370 0.3895 0.2603 0.031 Uiso 1 1 calc R . . . .
C10 C 0.6414(2) 0.59083(17) 0.22333(15) 0.0279(3) Uani 1 1 d . . . . .
H10 H 0.6420 0.5813 0.1252 0.034 Uiso 1 1 calc R . . . .
C11 C 0.5263(2) 0.71661(17) 0.28575(16) 0.0271(3) Uani 1 1 d . . . . .
H11 H 0.4488 0.7940 0.2299 0.033 Uiso 1 1 calc R . . . .
C12 C 0.52158(19) 0.73244(16) 0.43252(15) 0.0244(3) Uani 1 1 d . . . . .
C13 C 0.40154(19) 0.85806(17) 0.50239(16) 0.0268(3) Uani 1 1 d . . . . .
H13 H 0.3206 0.9362 0.4502 0.032 Uiso 1 1 calc R . . . .
C14 C 0.40186(19) 0.86718(17) 0.64491(16) 0.0269(3) Uani 1 1 d . . . . .
H14 H 0.3206 0.9514 0.6906 0.032 Uiso 1 1 calc R . . . .
C15 C 0.52077(19) 0.75352(16) 0.72372(15) 0.0252(3) Uani 1 1 d . . . . .
H15 H 0.5196 0.7615 0.8223 0.030 Uiso 1 1 calc R . . . .
C16 C 0.63885(18) 0.63078(16) 0.65955(15) 0.0233(3) Uani 1 1 d . . . . .
C17 C 0.76132(19) 0.51140(16) 0.74474(15) 0.0238(3) Uani 1 1 d . . . . .
C18 C 0.64109(18) 0.61713(16) 0.51284(15) 0.0223(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2198(17) . ?
O2 C17 1.2225(18) . ?
N1 C1 1.3415(19) . ?
N1 C5 1.3358(19) . ?
N2 C6 1.4755(19) . ?
N2 C7 1.4015(18) . ?
N2 C17 1.4031(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(2) . ?
C4 C5 1.395(2) . ?
C4 C6 1.5116(19) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.477(2) . ?
C8 C9 1.381(2) . ?
C8 C18 1.4151(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.419(2) . ?
C12 C13 1.421(2) . ?
C12 C18 1.419(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.372(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.402(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.372(2) . ?
C16 C17 1.474(2) . ?
C16 C18 1.4175(19) . ?

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
C5 N1 C1 116.65(12) . . ?
C7 N2 C6 117.48(11) . . ?
C7 N2 C17 124.84(13) . . ?
C17 N2 C6 117.61(11) . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.53(13) . . ?
C2 C1 H1 118.2 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.90(13) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.15(13) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 117.21(13) . . ?
C3 C4 C6 122.16(12) . . ?
C5 C4 C6 120.61(12) . . ?
N1 C5 C4 124.56(13) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
N2 C6 C4 111.06(11) . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C4 C6 H6A 109.4 . . ?
C4 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O1 C7 N2 119.92(14) . . ?
O1 C7 C8 123.02(13) . . ?
N2 C7 C8 117.06(12) . . ?
C9 C8 C7 119.89(13) . . ?
C9 C8 C18 119.98(14) . . ?
C18 C8 C7 120.13(13) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.54(13) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.24(13) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.89(14) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 122.76(14) . . ?
C18 C12 C11 118.47(13) . . ?
C18 C12 C13 118.76(13) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.37(14) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.71(14) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.47(13) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 119.65(13) . . ?
C15 C16 C18 120.26(14) . . ?
C18 C16 C17 120.08(13) . . ?
O2 C17 N2 119.79(14) . . ?
O2 C17 C16 123.05(13) . . ?
N2 C17 C16 117.16(12) . . ?
C8 C18 C12 119.86(13) . . ?
C8 C18 C16 120.72(14) . . ?
C16 C18 C12 119.41(13) . . ?

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
O1 C7 C8 C9 0.5(2) . . . . ?
O1 C7 C8 C18 179.53(12) . . . . ?
N1 C1 C2 C3 -0.7(2) . . . . ?
N2 C7 C8 C9 -179.38(11) . . . . ?
N2 C7 C8 C18 -0.33(19) . . . . ?
C1 N1 C5 C4 0.7(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C2 C3 C4 C6 -177.42(13) . . . . ?
C3 C4 C5 N1 -1.3(2) . . . . ?
C3 C4 C6 N2 89.82(15) . . . . ?
C5 N1 C1 C2 0.4(2) . . . . ?
C5 C4 C6 N2 -88.46(15) . . . . ?
C6 N2 C7 O1 -2.58(19) . . . . ?
C6 N2 C7 C8 177.29(11) . . . . ?
C6 N2 C17 O2 2.94(19) . . . . ?
C6 N2 C17 C16 -176.85(11) . . . . ?
C6 C4 C5 N1 177.06(14) . . . . ?
C7 N2 C6 C4 -86.83(14) . . . . ?
C7 N2 C17 O2 -179.95(12) . . . . ?
C7 N2 C17 C16 0.3(2) . . . . ?
C7 C8 C9 C10 179.73(12) . . . . ?
C7 C8 C18 C12 -179.12(11) . . . . ?
C7 C8 C18 C16 0.0(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C8 C18 C12 -0.1(2) . . . . ?
C9 C8 C18 C16 179.09(11) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C10 C11 C12 C13 -178.15(12) . . . . ?
C10 C11 C12 C18 1.4(2) . . . . ?
C11 C12 C13 C14 179.56(12) . . . . ?
C11 C12 C18 C8 -0.93(19) . . . . ?
C11 C12 C18 C16 179.90(12) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C13 C12 C18 C8 178.60(11) . . . . ?
C13 C12 C18 C16 -0.57(19) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 C17 -179.22(12) . . . . ?
C14 C15 C16 C18 -0.4(2) . . . . ?
C15 C16 C17 O2 -1.5(2) . . . . ?
C15 C16 C17 N2 178.28(11) . . . . ?
C15 C16 C18 C8 -178.42(11) . . . . ?
C15 C16 C18 C12 0.7(2) . . . . ?
C17 N2 C6 C4 90.50(14) . . . . ?
C17 N2 C7 O1 -179.70(11) . . . . ?
C17 N2 C7 C8 0.2(2) . . . . ?
C17 C16 C18 C8 0.4(2) . . . . ?
C17 C16 C18 C12 179.57(11) . . . . ?
C18 C8 C9 C10 0.7(2) . . . . ?
C18 C12 C13 C14 0.1(2) . . . . ?
C18 C16 C17 O2 179.67(12) . . . . ?
C18 C16 C17 N2 -0.55(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1511758'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H24 Cl2 N4 O4 Zn, 0.67(C2 H3 N)'
_chemical_formula_sum            'C37.33 H26 Cl2 N4.67 O4 Zn'
_chemical_formula_weight         740.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.4255(8)
_cell_length_b                   11.0223(8)
_cell_length_c                   28.403(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.650(8)
_cell_angle_gamma                90
_cell_volume                     3253.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1993
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.94
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.971
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.8453.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1515
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16379
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.133
_diffrn_reflns_theta_min         3.122
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1806
_reflns_number_total             3074
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3074
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0773
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1220P)²+7.3730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2085
_refine_ls_wR_factor_ref         0.2469
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 N3, C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: N3(0.33333) C19(0.33333) C20(0.33333) H20A(0.33333) H20B(0.33333)
 H20C(0.33333)
5.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
5.b Me refined with riding coordinates:
 C20(H20A,H20B,H20C)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.5000 0.78402(10) 0.7500 0.0620(5) Uani 1 2 d S T P . .
Cl1 Cl 0.68506(17) 0.87782(19) 0.74805(13) 0.1296(13) Uani 1 1 d . . . . .
O1 O 0.1161(6) 0.7174(4) 0.6107(2) 0.0892(18) Uani 1 1 d . . . . .
O2 O 0.2520(5) 0.3572(4) 0.5573(2) 0.0705(14) Uani 1 1 d . . . . .
N1 N 0.4746(6) 0.6549(5) 0.6976(2) 0.0715(17) Uani 1 1 d . . . . .
N2 N 0.1751(5) 0.5347(5) 0.5835(3) 0.0700(18) Uani 1 1 d . . . . .
C1 C 0.5745(9) 0.5833(8) 0.6892(3) 0.090(3) Uani 1 1 d . . . . .
H1 H 0.6585 0.6049 0.7020 0.108 Uiso 1 1 calc R . . . .
C2 C 0.5574(9) 0.4780(9) 0.6624(3) 0.101(3) Uani 1 1 d . . . . .
H2 H 0.6296 0.4296 0.6562 0.121 Uiso 1 1 calc R . . . .
C3 C 0.4359(9) 0.4441(8) 0.6448(3) 0.090(3) Uani 1 1 d . . . . .
H3 H 0.4229 0.3703 0.6278 0.108 Uiso 1 1 calc R . . . .
C4 C 0.3316(8) 0.5201(7) 0.6523(3) 0.081(2) Uani 1 1 d . . . . .
C5 C 0.3565(7) 0.6218(7) 0.6794(3) 0.074(2) Uani 1 1 d . . . . .
H5 H 0.2858 0.6719 0.6858 0.088 Uiso 1 1 calc R . . . .
C6 C 0.1975(7) 0.4908(7) 0.6323(3) 0.079(2) Uani 1 1 d . . . . .
H6A H 0.1842 0.4019 0.6330 0.095 Uiso 1 1 calc R . . . .
H6B H 0.1347 0.5290 0.6521 0.095 Uiso 1 1 calc R . . . .
C7 C 0.1297(6) 0.6547(6) 0.5767(4) 0.072(2) Uani 1 1 d . . . . .
C8 C 0.1026(6) 0.6942(5) 0.5277(3) 0.070(2) Uani 1 1 d . . . . .
C9 C 0.0508(6) 0.8072(6) 0.5181(4) 0.076(3) Uani 1 1 d . . . . .
H9 H 0.0332 0.8591 0.5435 0.091 Uiso 1 1 calc R . . . .
C10 C 0.0233(6) 0.8470(6) 0.4715(4) 0.077(3) Uani 1 1 d . . . . .
H10 H -0.0114 0.9258 0.4658 0.092 Uiso 1 1 calc R . . . .
C11 C 0.0458(6) 0.7737(6) 0.4336(3) 0.071(2) Uani 1 1 d . . . . .
H11 H 0.0261 0.8011 0.4022 0.085 Uiso 1 1 calc R . . . .
C12 C 0.0992(6) 0.6565(6) 0.4426(4) 0.072(2) Uani 1 1 d . . . . .
C13 C 0.1252(6) 0.5766(7) 0.4047(3) 0.077(2) Uani 1 1 d . . . . .
H13 H 0.1086 0.6022 0.3728 0.092 Uiso 1 1 calc R . . . .
C14 C 0.1746(6) 0.4617(7) 0.4146(4) 0.077(3) Uani 1 1 d . . . . .
H14 H 0.1915 0.4088 0.3894 0.093 Uiso 1 1 calc R . . . .
C15 C 0.2001(5) 0.4225(6) 0.4618(3) 0.063(2) Uani 1 1 d . . . . .
H15 H 0.2324 0.3431 0.4682 0.075 Uiso 1 1 calc R . . . .
C16 C 0.1781(5) 0.4988(5) 0.4984(3) 0.061(2) Uani 1 1 d . . . . .
C17 C 0.2051(6) 0.4559(5) 0.5475(3) 0.063(2) Uani 1 1 d . . . . .
C18 C 0.1273(5) 0.6154(5) 0.4903(3) 0.063(2) Uani 1 1 d . . . . .
N3 N -0.0803(15) 0.6245(18) 0.6925(7) 0.067(4) Uani 0.3333 1 d . U . A -1
C19 C -0.040(3) 0.659(3) 0.7260(11) 0.045(5) Uani 0.3333 1 d . U . A -1
C20 C 0.013(3) 0.687(3) 0.7707(10) 0.050(6) Uani 0.3333 1 d . U . A -1
H20A H 0.0160 0.7751 0.7747 0.076 Uiso 0.3333 1 calc R . . A -1
H20B H -0.0390 0.6509 0.7943 0.076 Uiso 0.3333 1 calc R . . A -1
H20C H 0.1008 0.6540 0.7748 0.076 Uiso 0.3333 1 calc R . . A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 Cl1 2.1936(18) . ?
Zn1 Cl1 2.1936(18) 2_656 ?
Zn1 N1 2.062(6) . ?
Zn1 N1 2.062(6) 2_656 ?
O1 C7 1.207(9) . ?
O2 C17 1.216(8) . ?
N1 C1 1.342(9) . ?
N1 C5 1.347(10) . ?
N2 C6 1.469(11) . ?
N2 C7 1.413(9) . ?
N2 C17 1.398(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(10) . ?
C4 C5 1.373(11) . ?
C4 C6 1.500(11) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.462(12) . ?
C8 C9 1.376(10) . ?
C8 C18 1.413(10) . ?
C9 H9 0.9500 . ?
C9 C10 1.403(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.422(9) . ?
C12 C13 1.434(10) . ?
C12 C18 1.436(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.413(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.371(9) . ?
C16 C17 1.476(11) . ?
C16 C18 1.402(8) . ?
N3 C19 1.07(3) . ?
C19 C20 1.38(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
Cl1 Zn1 Cl1 123.76(12) . 2_656 ?
N1 Zn1 Cl1 106.39(17) 2_656 . ?
N1 Zn1 Cl1 106.39(17) . 2_656 ?
N1 Zn1 Cl1 111.63(19) . . ?
N1 Zn1 Cl1 111.63(19) 2_656 2_656 ?
N1 Zn1 N1 92.7(4) . 2_656 ?
C1 N1 Zn1 118.5(6) . . ?
C1 N1 C5 118.1(7) . . ?
C5 N1 Zn1 121.5(4) . . ?
C7 N2 C6 117.6(6) . . ?
C17 N2 C6 117.3(6) . . ?
C17 N2 C7 125.0(8) . . ?
N1 C1 H1 119.3 . . ?
N1 C1 C2 121.3(9) . . ?
C2 C1 H1 119.3 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(7) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(8) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C6 121.7(8) . . ?
C5 C4 C3 117.3(8) . . ?
C5 C4 C6 121.0(6) . . ?
N1 C5 C4 124.1(6) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N2 C6 C4 111.0(6) . . ?
N2 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C4 C6 H6A 109.4 . . ?
C4 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O1 C7 N2 119.1(9) . . ?
O1 C7 C8 124.4(7) . . ?
N2 C7 C8 116.5(7) . . ?
C9 C8 C7 120.0(7) . . ?
C9 C8 C18 119.9(9) . . ?
C18 C8 C7 120.0(6) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(8) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(7) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.8(8) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C13 121.3(9) . . ?
C11 C12 C18 120.1(7) . . ?
C13 C12 C18 118.6(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(9) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.7(7) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(7) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.2(6) . . ?
C15 C16 C18 121.4(8) . . ?
C18 C16 C17 119.4(6) . . ?
O2 C17 N2 119.9(8) . . ?
O2 C17 C16 123.0(6) . . ?
N2 C17 C16 117.1(6) . . ?
C8 C18 C12 118.8(6) . . ?
C16 C18 C8 121.9(8) . . ?
C16 C18 C12 119.3(7) . . ?
N3 C19 C20 172(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Zn1 N1 C1 C2 165.4(8) . . . . ?
Zn1 N1 C5 C4 -165.5(7) . . . . ?
O1 C7 C8 C9 -4.1(10) . . . . ?
O1 C7 C8 C18 177.1(6) . . . . ?
N1 C1 C2 C3 -1.6(16) . . . . ?
N2 C7 C8 C9 176.1(5) . . . . ?
N2 C7 C8 C18 -2.7(8) . . . . ?
C1 N1 C5 C4 -1.0(13) . . . . ?
C1 C2 C3 C4 3.2(16) . . . . ?
C2 C3 C4 C5 -3.6(14) . . . . ?
C2 C3 C4 C6 177.5(9) . . . . ?
C3 C4 C5 N1 2.6(14) . . . . ?
C3 C4 C6 N2 -85.1(10) . . . . ?
C5 N1 C1 C2 0.5(14) . . . . ?
C5 C4 C6 N2 96.1(9) . . . . ?
C6 N2 C7 O1 2.9(9) . . . . ?
C6 N2 C7 C8 -177.3(5) . . . . ?
C6 N2 C17 O2 -2.5(9) . . . . ?
C6 N2 C17 C16 178.0(5) . . . . ?
C6 C4 C5 N1 -178.5(8) . . . . ?
C7 N2 C6 C4 -88.3(7) . . . . ?
C7 N2 C17 O2 174.9(6) . . . . ?
C7 N2 C17 C16 -4.6(9) . . . . ?
C7 C8 C9 C10 -179.7(6) . . . . ?
C7 C8 C18 C12 179.7(5) . . . . ?
C7 C8 C18 C16 -0.2(8) . . . . ?
C8 C9 C10 C11 0.8(10) . . . . ?
C9 C8 C18 C12 0.9(8) . . . . ?
C9 C8 C18 C16 -179.0(5) . . . . ?
C9 C10 C11 C12 -0.7(9) . . . . ?
C10 C11 C12 C13 -179.7(6) . . . . ?
C10 C11 C12 C18 0.7(9) . . . . ?
C11 C12 C13 C14 -178.6(6) . . . . ?
C11 C12 C18 C8 -0.8(8) . . . . ?
C11 C12 C18 C16 179.1(5) . . . . ?
C12 C13 C14 C15 -0.2(10) . . . . ?
C13 C12 C18 C8 179.6(5) . . . . ?
C13 C12 C18 C16 -0.5(8) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
C14 C15 C16 C17 179.8(5) . . . . ?
C14 C15 C16 C18 1.7(8) . . . . ?
C15 C16 C17 O2 3.6(9) . . . . ?
C15 C16 C17 N2 -176.9(5) . . . . ?
C15 C16 C18 C8 179.1(5) . . . . ?
C15 C16 C18 C12 -0.8(8) . . . . ?
C17 N2 C6 C4 89.3(7) . . . . ?
C17 N2 C7 O1 -174.5(6) . . . . ?
C17 N2 C7 C8 5.3(9) . . . . ?
C17 C16 C18 C8 0.9(8) . . . . ?
C17 C16 C18 C12 -179.0(5) . . . . ?
C18 C8 C9 C10 -0.9(9) . . . . ?
C18 C12 C13 C14 1.0(9) . . . . ?
C18 C16 C17 O2 -178.1(5) . . . . ?
C18 C16 C17 N2 1.4(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1511757'
_audit_update_record             
;
2016-10-26 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H28 Cl2 Mn N4 O5'
_chemical_formula_sum            'C37 H28 Cl2 Mn N4 O5'
_chemical_formula_weight         734.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.4298(13)
_cell_length_b                   4.6669(2)
_cell_length_c                   27.8832(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.266(3)
_cell_angle_gamma                90
_cell_volume                     3123.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3539
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.69
_cell_measurement_theta_min      3.36
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.515
_exptl_absorpt_coefficient_mu    5.460
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0788 before and 0.0543 after correction.
The Ratio of minimum to maximum transmission is 0.7516.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1508
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9538
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.477
_diffrn_reflns_theta_max         67.477
_diffrn_reflns_theta_min         3.358
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2461
_reflns_number_total             2815
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+1.9490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.87 with sigma of 0.01
 C19-H1
 1.906419 with sigma of 0.02
 Mn1-H1
 2.667561 with sigma of 0.02
3. Others
 Fixed Sof: Cl1(0.5) Cl2(0.5) O1(0.5) H1(0.5) C19(0.5) H19A(0.5) H19B(0.5)
 H19C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15)
4.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.5000 0.93196(10) 0.7500 0.03531(18) Uani 1 2 d DS T P . .
Cl1 Cl 0.39513(4) 1.10987(19) 0.72933(3) 0.0225(2) Uani 0.5 1 d . . . A 1
Cl2 Cl 0.46184(4) 1.41258(18) 0.74423(3) 0.0214(2) Uani 0.5 1 d . . . A 3
O1 O 0.42316(11) 0.7497(6) 0.74206(10) 0.0235(6) Uani 0.5 1 d D . . A 2
H1 H 0.4197(8) 0.562(2) 0.7402(17) 0.035 Uiso 0.5 1 d DR . . B 2
O2 O 0.31529(6) 0.9171(3) 0.53013(6) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.41608(6) 0.2933(3) 0.47089(5) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.48482(7) 0.9119(4) 0.66476(6) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.36426(7) 0.5997(3) 0.50001(6) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.51780(8) 1.0505(5) 0.64414(8) 0.0245(4) Uani 1 1 d . . . . .
H1A H 0.5456 1.1747 0.6650 0.029 Uiso 1 1 calc R . . . .
C2 C 0.51320(9) 1.0210(6) 0.59388(8) 0.0318(5) Uani 1 1 d . . . . .
H2 H 0.5375 1.1235 0.5805 0.038 Uiso 1 1 calc R . . . .
C3 C 0.47297(8) 0.8413(5) 0.56287(7) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.4701 0.8143 0.5283 0.030 Uiso 1 1 calc R . . . .
C4 C 0.43705(8) 0.7016(4) 0.58292(7) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.44519(10) 0.7438(5) 0.63411(8) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.4210 0.6469 0.6484 0.035 Uiso 1 1 calc R . . . .
C6 C 0.39182(9) 0.5012(4) 0.55247(7) 0.0237(4) Uani 1 1 d . . . . .
H6A H 0.4082 0.3095 0.5516 0.028 Uiso 1 1 calc R . . . .
H6B H 0.3636 0.4816 0.5696 0.028 Uiso 1 1 calc R . . . .
C7 C 0.32423(8) 0.8154(4) 0.49339(8) 0.0238(4) Uani 1 1 d . . . . .
C8 C 0.29450(8) 0.9082(4) 0.44054(8) 0.0259(4) Uani 1 1 d . . . . .
C9 C 0.25287(9) 1.1087(5) 0.43129(9) 0.0305(5) Uani 1 1 d . . . . .
H9 H 0.2433 1.1866 0.4588 0.037 Uiso 1 1 calc R . . . .
C10 C 0.22417(9) 1.2002(6) 0.38126(9) 0.0378(6) Uani 1 1 d . . . . .
H10 H 0.1952 1.3377 0.3751 0.045 Uiso 1 1 calc R . . . .
C11 C 0.23808(10) 1.0909(6) 0.34159(9) 0.0376(6) Uani 1 1 d . . . . .
H11 H 0.2185 1.1539 0.3080 0.045 Uiso 1 1 calc R . . . .
C12 C 0.28103(9) 0.8860(5) 0.34955(8) 0.0308(5) Uani 1 1 d . . . . .
C13 C 0.29771(10) 0.7708(5) 0.30988(8) 0.0357(5) Uani 1 1 d . . . . .
H13 H 0.2796 0.8332 0.2760 0.043 Uiso 1 1 calc R . . . .
C14 C 0.33926(10) 0.5720(5) 0.31933(8) 0.0349(5) Uani 1 1 d . . . . .
H14 H 0.3500 0.4989 0.2921 0.042 Uiso 1 1 calc R . . . .
C15 C 0.36645(10) 0.4745(5) 0.36939(8) 0.0305(5) Uani 1 1 d . . . . .
H15 H 0.3949 0.3338 0.3757 0.037 Uiso 1 1 calc R . . . .
C16 C 0.35166(9) 0.5832(4) 0.40897(8) 0.0257(4) Uani 1 1 d . . . . .
C17 C 0.38026(9) 0.4775(5) 0.46125(8) 0.0254(4) Uani 1 1 d . . . . .
C18 C 0.30942(8) 0.7914(4) 0.40015(8) 0.0252(4) Uani 1 1 d . . . . .
C19 C 0.36989(17) 0.8707(10) 0.71537(18) 0.0302(9) Uani 0.5 1 d D . . A 2
H19A H 0.3537 0.7718 0.6828 0.045 Uiso 0.5 1 calc GR . . A 2
H19B H 0.3742 1.0748 0.7092 0.045 Uiso 0.5 1 calc GR . . A 2
H19C H 0.3453 0.8487 0.7358 0.045 Uiso 0.5 1 calc GR . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 Cl1 2.6681(9) . ?
Mn1 Cl1 2.6680(9) 2_656 ?
Mn1 Cl2 2.4281(10) 2_656 ?
Mn1 Cl2 2.5961(10) 1_545 ?
Mn1 Cl2 2.5961(10) 2_646 ?
Mn1 Cl2 2.4281(10) . ?
Mn1 O1 2.075(3) 2_656 ?
Mn1 O1 2.075(3) . ?
Mn1 N1 2.2806(16) . ?
Mn1 N1 2.2806(16) 2_656 ?
Cl2 Mn1 2.5961(10) 1_565 ?
O1 H1 0.879(10) . ?
O1 C19 1.429(5) . ?
O2 C7 1.216(3) . ?
O3 C17 1.216(3) . ?
N1 C1 1.331(3) . ?
N1 C5 1.339(3) . ?
N2 C6 1.472(2) . ?
N2 C7 1.400(3) . ?
N2 C17 1.396(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.374(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 C5 1.387(3) . ?
C4 C6 1.508(3) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.482(3) . ?
C8 C9 1.372(3) . ?
C8 C18 1.411(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.410(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.366(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.413(4) . ?
C12 C13 1.415(3) . ?
C12 C18 1.426(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.365(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.413(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(3) . ?
C16 C17 1.482(3) . ?
C16 C18 1.409(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
Cl1 Mn1 Cl1 143.74(4) 2_656 . ?
Cl2 Mn1 Cl2 136.50(4) . 1_545 ?
Cl2 Mn1 Cl2 178.473(17) 2_656 1_545 ?
Cl2 Mn1 Cl2 41.98(4) 1_545 2_646 ?
Cl2 Mn1 Cl2 136.50(4) 2_656 2_646 ?
Cl2 Mn1 Cl2 178.473(18) . 2_646 ?
Cl2 Mn1 Cl2 45.03(4) 2_656 . ?
O1 Mn1 O1 131.59(16) . 2_656 ?
O1 Mn1 N1 92.42(9) 2_656 2_656 ?
O1 Mn1 N1 85.64(9) . 2_656 ?
O1 Mn1 N1 85.64(9) 2_656 . ?
O1 Mn1 N1 92.43(9) . . ?
N1 Mn1 Cl1 88.52(5) 2_656 2_656 ?
N1 Mn1 Cl1 88.52(5) . . ?
N1 Mn1 Cl1 92.94(5) . 2_656 ?
N1 Mn1 Cl1 92.95(5) 2_656 . ?
N1 Mn1 Cl2 91.92(5) 2_656 . ?
N1 Mn1 Cl2 92.42(5) . . ?
N1 Mn1 Cl2 88.04(5) . 1_545 ?
N1 Mn1 Cl2 87.57(5) 2_656 1_545 ?
N1 Mn1 Cl2 88.04(5) 2_656 2_646 ?
N1 Mn1 Cl2 91.92(5) . 2_656 ?
N1 Mn1 Cl2 87.57(5) . 2_646 ?
N1 Mn1 Cl2 92.42(5) 2_656 2_656 ?
N1 Mn1 N1 175.30(9) . 2_656 ?
Mn1 Cl2 Mn1 136.50(4) . 1_565 ?
Mn1 O1 H1 119.1(15) . . ?
C19 O1 Mn1 126.2(3) . . ?
C19 O1 H1 107.6(15) . . ?
C1 N1 Mn1 121.08(13) . . ?
C1 N1 C5 117.25(17) . . ?
C5 N1 Mn1 121.48(13) . . ?
C7 N2 C6 116.28(17) . . ?
C17 N2 C6 118.48(17) . . ?
C17 N2 C7 125.23(17) . . ?
N1 C1 H1A 118.7 . . ?
N1 C1 C2 122.56(19) . . ?
C2 C1 H1A 118.7 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.97(18) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 117.09(18) . . ?
C3 C4 C6 123.23(17) . . ?
C5 C4 C6 119.64(18) . . ?
N1 C5 C4 124.43(19) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
N2 C6 C4 112.97(16) . . ?
N2 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
C4 C6 H6A 109.0 . . ?
C4 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
O2 C7 N2 119.96(18) . . ?
O2 C7 C8 123.2(2) . . ?
N2 C7 C8 116.84(18) . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 C18 120.5(2) . . ?
C18 C8 C7 119.83(19) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 123.3(2) . . ?
C11 C12 C18 118.5(2) . . ?
C13 C12 C18 118.1(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 119.4(2) . . ?
C15 C16 C18 120.6(2) . . ?
C18 C16 C17 119.99(19) . . ?
O3 C17 N2 120.39(18) . . ?
O3 C17 C16 122.77(19) . . ?
N2 C17 C16 116.83(19) . . ?
C8 C18 C12 119.2(2) . . ?
C16 C18 C8 121.16(19) . . ?
C16 C18 C12 119.6(2) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Mn1 N1 C1 C2 173.54(17) . . . . ?
Mn1 N1 C5 C4 -173.91(16) . . . . ?
O2 C7 C8 C9 -3.2(3) . . . . ?
O2 C7 C8 C18 176.43(19) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
N2 C7 C8 C9 176.82(18) . . . . ?
N2 C7 C8 C18 -3.6(3) . . . . ?
C1 N1 C5 C4 1.1(3) . . . . ?
C1 C2 C3 C4 2.0(3) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C2 C3 C4 C6 -179.9(2) . . . . ?
C3 C4 C5 N1 0.8(3) . . . . ?
C3 C4 C6 N2 -38.6(3) . . . . ?
C5 N1 C1 C2 -1.5(3) . . . . ?
C5 C4 C6 N2 143.8(2) . . . . ?
C6 N2 C7 O2 2.4(3) . . . . ?
C6 N2 C7 C8 -177.55(17) . . . . ?
C6 N2 C17 O3 0.2(3) . . . . ?
C6 N2 C17 C16 -179.80(17) . . . . ?
C6 C4 C5 N1 178.5(2) . . . . ?
C7 N2 C6 C4 -78.9(2) . . . . ?
C7 N2 C17 O3 179.02(19) . . . . ?
C7 N2 C17 C16 -1.0(3) . . . . ?
C7 C8 C9 C10 179.9(2) . . . . ?
C7 C8 C18 C12 -179.04(18) . . . . ?
C7 C8 C18 C16 1.1(3) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C8 C18 C12 0.5(3) . . . . ?
C9 C8 C18 C16 -179.33(19) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 -178.7(2) . . . . ?
C10 C11 C12 C18 0.8(3) . . . . ?
C11 C12 C13 C14 -179.7(2) . . . . ?
C11 C12 C18 C8 -1.1(3) . . . . ?
C11 C12 C18 C16 178.79(19) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C12 C18 C8 178.45(19) . . . . ?
C13 C12 C18 C16 -1.7(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C17 179.58(19) . . . . ?
C14 C15 C16 C18 0.1(3) . . . . ?
C15 C16 C17 O3 -1.2(3) . . . . ?
C15 C16 C17 N2 178.77(19) . . . . ?
C15 C16 C18 C8 -178.91(19) . . . . ?
C15 C16 C18 C12 1.2(3) . . . . ?
C17 N2 C6 C4 100.0(2) . . . . ?
C17 N2 C7 O2 -176.43(18) . . . . ?
C17 N2 C7 C8 3.6(3) . . . . ?
C17 C16 C18 C8 1.6(3) . . . . ?
C17 C16 C18 C12 -178.23(19) . . . . ?
C18 C8 C9 C10 0.3(3) . . . . ?
C18 C12 C13 C14 0.8(3) . . . . ?
C18 C16 C17 O3 178.2(2) . . . . ?
C18 C16 C17 N2 -1.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
