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

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

data_b359
_audit_block_doi                 10.5517/ccr9hm4
_database_code_depnum_ccdc_archive 'CCDC 694326'
_audit_update_record             
;
2008-07-08 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_audit_creation_method           'Created with Diamond v2.0'
_audit_creation_date             08-07-08
_chemical_formula_sum            'C14 H9 N5 O'
_chemical_formula_structural     C14H9N5O
_chemical_formula_analytical     C14H9N5O
_chemical_name_common            
;
2-benzoyl-1,1,3,3-tetracyanopropenide ammonium
;
_chemical_name_systematic        
;
2-benzoyl-1,1,3,3-tetracyanopropenide ammonium
;
_chemical_name_structure_type    
;
NO5P9Q14
;
_chemical_formula_weight         263.260
_chemical_formula_weight_meas    263.260
_chemical_melting_point          454.000
_refine_ls_R_factor_all          0.043
_cell_length_a                   8.1856(11)
_cell_length_b                   9.5361(12)
_cell_length_c                   10.1685(11)
_cell_angle_alpha                115.957(13)
_cell_angle_beta                 102.087(12)
_cell_angle_gamma                103.220(12)
_cell_volume                     649.9(1)
_cell_formula_units_Z            2
_exptl_crystal_density_meas      1.345
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
N ? 1.200
O ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 0.3317(2) 0.9165(1) 0.3444(1) 1.000 2 i ? d Uani 0.0452(3)
N1 N 0.6572(2) 1.3967(2) -0.1271(2) 1.000 2 i ? d Uani 0.0447(3)
N2 N -0.0091(2) 0.6880(2) -0.0120(2) 1.000 2 i ? d Uani 0.0639(4)
N3 N 0.2952(3) 0.9874(2) -0.1573(2) 1.000 2 i ? d Uani 0.0664(5)
N4 N 0.6553(2) 1.4119(2) 0.5830(2) 1.000 2 i ? d Uani 0.0547(4)
N5 N 0.5481(2) 1.3676(2) 0.1267(2) 1.000 2 i ? d Uani 0.0564(4)
C1 C 0.3349(2) 1.0831(2) 0.2280(2) 1.000 2 i ? d Uani 0.0337(3)
C2 C 0.2984(2) 1.0350(2) 0.3463(1) 1.000 2 i ? d Uani 0.0333(3)
C3 C 0.2243(2) 1.1343(2) 0.4584(2) 1.000 2 i ? d Uani 0.0336(3)
C4 C 0.1375(2) 1.2324(2) 0.4298(2) 1.000 2 i ? d Uani 0.0431(3)
C5 C 0.0572(2) 1.3141(2) 0.5314(2) 1.000 2 i ? d Uani 0.0541(4)
C6 C 0.0694(2) 1.3023(2) 0.6635(2) 1.000 2 i ? d Uani 0.0538(4)
C7 C 0.1580(2) 1.2076(2) 0.6936(2) 1.000 2 i ? d Uani 0.0471(4)
C8 C 0.2336(2) 1.1206(2) 0.5910(2) 1.000 2 i ? d Uani 0.0382(3)
C9 C 0.2347(2) 0.9642(2) 0.0713(2) 1.000 2 i ? d Uani 0.0385(3)
C10 C 0.4677(2) 1.2380(2) 0.2894(2) 1.000 2 i ? d Uani 0.0361(3)
C11 C 0.5719(2) 1.3351(2) 0.4521(2) 1.000 2 i ? d Uani 0.0393(3)
C12 C 0.5125(2) 1.3074(2) 0.1978(2) 1.000 2 i ? d Uani 0.0418(3)
C13 C 0.0987(2) 0.8126(2) 0.0264(2) 1.000 2 i ? d Uani 0.0450(4)
C14 C 0.2676(2) 0.9792(2) -0.0546(2) 1.000 2 i ? d Uani 0.0440(3)
H4 H 0.130(2) 1.244(2) 0.338(2) 1.000 2 i ? d Uiso 0.055(5)
H5 H -0.012(3) 1.374(2) 0.506(2) 1.000 2 i ? d Uiso 0.064(6)
H6 H 0.013(3) 1.361(3) 0.730(3) 1.000 2 i ? d Uiso 0.077(6)
H7 H 0.164(3) 1.200(3) 0.788(3) 1.000 2 i ? d Uiso 0.068(6)
H8 H 0.296(2) 1.051(2) 0.6093(19) 1.000 2 i ? d Uiso 0.044(4)
H10 H 0.576(3) 1.431(3) -0.162(3) 1.000 2 i ? d Uiso 0.078(7)
H11 H 0.772(4) 1.476(3) -0.095(3) 1.000 2 i ? d Uiso 0.097(8)
H12 H 0.660(3) 1.295(3) -0.195(3) 1.000 2 i ? d Uiso 0.076(6)
H13 H 0.633(3) 1.385(3) -0.042(3) 1.000 2 i ? d Uiso 0.087(7)


####################################################################### 
# 
# 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_yak402
_database_code_depnum_ccdc_archive 'CCDC 1575021'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 N4 O2 Rb'
_chemical_formula_sum            'C15 H7 N4 O2 Rb'
_chemical_formula_weight         360.72

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'
Rb Rb -0.4688 1.6079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2743(3)
_cell_length_b                   9.8536(4)
_cell_length_c                   18.8581(8)
_cell_angle_alpha                87.273(3)
_cell_angle_beta                 78.288(3)
_cell_angle_gamma                89.663(3)
_cell_volume                     1503.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2004
_cell_measurement_theta_min      3
_cell_measurement_theta_max      55

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .15
_exptl_absorpt_coefficient_mu    4.642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            12037
_diffrn_reflns_av_unetI/netI     0.1004
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.492
_diffrn_reflns_theta_max         72.951
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5552
_reflns_number_gt                2990
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5552
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Rb1 Rb 0.51844(6) 0.37518(5) 0.89876(3) 0.05196(16) Uani 1 1 d . . . . .
Rb2 Rb 0.01475(6) 1.14467(5) 0.89933(3) 0.05271(16) Uani 1 1 d . . . . .
O1A O 1.1376(4) 0.6122(3) 0.18013(19) 0.0570(9) Uani 1 1 d . . . . .
O2A O 0.6005(5) 0.6857(4) 0.46798(19) 0.0704(11) Uani 1 1 d . . . . .
N1A N 1.2222(6) 0.3261(5) 0.3435(3) 0.0723(14) Uani 1 1 d . . . . .
N2A N 1.0607(6) 0.0304(4) 0.2131(2) 0.0622(12) Uani 1 1 d . . . . .
N3A N 0.9707(7) 0.1583(4) 0.0621(3) 0.0784(15) Uani 1 1 d . . . . .
N4A N 0.8532(5) 0.5826(4) 0.0714(2) 0.0592(11) Uani 1 1 d . . . . .
C1A C 1.0414(6) 0.5330(4) 0.2182(3) 0.0416(11) Uani 1 1 d . . . . .
C2A C 0.9262(5) 0.5714(4) 0.2844(2) 0.0384(10) Uani 1 1 d . . . . .
C3A C 0.9252(6) 0.7062(4) 0.3036(3) 0.0461(12) Uani 1 1 d . . . . .
H3A H 0.9983 0.7683 0.2754 0.055 Uiso 1 1 calc R U . . .
C4A C 0.8168(6) 0.7485(5) 0.3640(3) 0.0525(13) Uani 1 1 d . . . . .
H4A H 0.8159 0.8389 0.3761 0.063 Uiso 1 1 calc R U . . .
C5A C 0.7092(6) 0.6558(5) 0.4066(3) 0.0498(12) Uani 1 1 d . . . . .
C6A C 0.7095(6) 0.5217(5) 0.3877(3) 0.0507(12) Uani 1 1 d . . . . .
H6A H 0.6378 0.4593 0.4164 0.061 Uiso 1 1 calc R U . . .
C7A C 0.8149(6) 0.4807(4) 0.3271(3) 0.0448(11) Uani 1 1 d . . . . .
H7A H 0.8122 0.3910 0.3141 0.054 Uiso 1 1 calc R U . . .
C8A C 1.0355(5) 0.3882(4) 0.1936(2) 0.0396(11) Uani 1 1 d . . . . .
C9A C 1.0919(5) 0.2827(4) 0.2346(3) 0.0433(11) Uani 1 1 d . . . . .
C10A C 1.1620(6) 0.3094(5) 0.2957(3) 0.0514(13) Uani 1 1 d . . . . .
C11A C 1.0762(6) 0.1439(5) 0.2216(3) 0.0451(12) Uani 1 1 d . . . . .
C12A C 0.9758(6) 0.3761(4) 0.1297(3) 0.0452(12) Uani 1 1 d . . . . .
C13A C 0.9737(6) 0.2537(5) 0.0933(3) 0.0515(13) Uani 1 1 d . . . . .
C14A C 0.9088(6) 0.4901(5) 0.0978(3) 0.0467(12) Uani 1 1 d . . . . .
C15A C 0.5931(10) 0.8224(6) 0.4900(4) 0.108(3) Uani 1 1 d . . . . .
H15A H 0.6939 0.8448 0.5046 0.161 Uiso 1 1 calc R U . . .
H15B H 0.5019 0.8319 0.5299 0.161 Uiso 1 1 calc R U . . .
H15C H 0.5786 0.8825 0.4502 0.161 Uiso 1 1 calc R U . . .
O1 O 0.3569(4) 1.1464(3) 0.82461(19) 0.0576(9) Uani 1 1 d . . . . .
O2 O 0.8763(7) 1.2885(5) 0.5353(2) 0.1051(17) Uani 1 1 d . . . . .
N1 N 0.2874(6) 0.8953(4) 0.6541(3) 0.0663(12) Uani 1 1 d . . . . .
N2 N 0.4380(6) 0.5731(4) 0.7881(2) 0.0602(12) Uani 1 1 d . . . . .
N3 N 0.5301(7) 0.6690(5) 0.9390(3) 0.0815(16) Uani 1 1 d . . . . .
N4 N 0.6446(5) 1.0951(4) 0.9293(2) 0.0565(11) Uani 1 1 d . . . . .
C1 C 0.4558(6) 1.0758(4) 0.7843(3) 0.0433(12) Uani 1 1 d . . . . .
C2 C 0.5653(5) 1.1275(4) 0.7198(3) 0.0418(11) Uani 1 1 d . . . . .
C3 C 0.5674(6) 1.2674(5) 0.7015(3) 0.0495(12) Uani 1 1 d . . . . .
H3 H 0.4966 1.3247 0.7310 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6717(7) 1.3208(5) 0.6412(3) 0.0608(14) Uani 1 1 d . . . . .
H4 H 0.6726 1.4139 0.6305 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7760(7) 1.2371(5) 0.5959(3) 0.0597(14) Uani 1 1 d . . . . .
C6 C 0.7771(6) 1.0988(5) 0.6130(3) 0.0582(14) Uani 1 1 d . . . . .
H6 H 0.8473 1.0419 0.5830 0.070 Uiso 1 1 calc R U . . .
C7 C 0.6744(6) 1.0462(5) 0.6742(3) 0.0468(12) Uani 1 1 d . . . . .
H7 H 0.6777 0.9535 0.6857 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4628(5) 0.9254(4) 0.8081(2) 0.0388(11) Uani 1 1 d . . . . .
C9 C 0.4079(6) 0.8298(4) 0.7660(3) 0.0435(11) Uani 1 1 d . . . . .
C10 C 0.3418(6) 0.8690(5) 0.7044(3) 0.0468(12) Uani 1 1 d . . . . .
C11 C 0.4236(6) 0.6872(5) 0.7794(3) 0.0447(12) Uani 1 1 d . . . . .
C12 C 0.5224(6) 0.9016(4) 0.8717(3) 0.0429(11) Uani 1 1 d . . . . .
C13 C 0.5265(7) 0.7703(5) 0.9077(3) 0.0511(13) Uani 1 1 d . . . . .
C14 C 0.5891(5) 1.0088(4) 0.9041(3) 0.0420(11) Uani 1 1 d . . . . .
C15 C 0.9429(18) 1.2213(14) 0.4817(7) 0.091(4) Uani 0.5 1 d . . P . .
H151 H 0.9838 1.2825 0.4409 0.136 Uiso 0.5 1 calc R U P . .
H152 H 0.8628 1.1611 0.4696 0.136 Uiso 0.5 1 calc R U P . .
H153 H 1.0328 1.1692 0.4938 0.136 Uiso 0.5 1 calc R U P . .
C151 C 0.9254(16) 1.4157(12) 0.5209(6) 0.077(3) Uani 0.5 1 d . . P . .
H15D H 1.0230 1.4191 0.4833 0.115 Uiso 0.5 1 calc R U P . .
H15E H 0.9492 1.4529 0.5638 0.115 Uiso 0.5 1 calc R U P . .
H15F H 0.8397 1.4678 0.5051 0.115 Uiso 0.5 1 calc R U P . .


_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
Rb1 O1A 2.932(3) 2_766 ?
Rb1 N2 2.961(4) . ?
Rb1 N3 3.015(5) 2_667 ?
Rb1 N4 3.016(4) 1_545 ?
Rb1 N3 3.035(4) . ?
Rb1 N4A 3.042(4) 2_666 ?
Rb1 O1 3.149(3) 1_545 ?
Rb1 C14 3.654(4) 1_545 ?
Rb1 Rb1 4.5974(10) 2_667 ?
Rb1 Rb2 4.6830(7) 1_645 ?
Rb1 Rb2 4.7560(8) 1_545 ?
Rb2 O1 2.895(3) . ?
Rb2 N2A 2.959(4) 2_666 ?
Rb2 N4A 3.023(4) 2_676 ?
Rb2 N3A 3.025(5) 1_466 ?
Rb2 N4 3.038(4) 1_455 ?
Rb2 N3A 3.047(4) 2_666 ?
Rb2 O1A 3.157(4) 2_676 ?
Rb2 C14A 3.662(5) 2_676 ?
Rb2 Rb2 4.6050(11) 2_577 ?
Rb2 Rb1 4.6829(7) 1_465 ?
Rb2 Rb1 4.7560(8) 1_565 ?
O1A C1A 1.217(5) . ?
O1A Rb1 2.932(3) 2_766 ?
O1A Rb2 3.157(4) 2_676 ?
O2A C5A 1.357(6) . ?
O2A C15A 1.425(7) . ?
N1A C10A 1.134(6) . ?
N2A C11A 1.149(6) . ?
N2A Rb2 2.959(4) 2_666 ?
N3A C13A 1.136(6) . ?
N3A Rb2 3.025(5) 1_644 ?
N3A Rb2 3.047(4) 2_666 ?
N4A C14A 1.156(6) . ?
N4A Rb2 3.023(4) 2_676 ?
N4A Rb1 3.042(4) 2_666 ?
C1A C2A 1.472(6) . ?
C1A C8A 1.526(6) . ?
C2A C7A 1.391(6) . ?
C2A C3A 1.393(6) . ?
C3A C4A 1.379(7) . ?
C4A C5A 1.386(7) . ?
C5A C6A 1.385(6) . ?
C6A C7A 1.366(7) . ?
C8A C9A 1.399(6) . ?
C8A C12A 1.403(7) . ?
C9A C11A 1.413(6) . ?
C9A C10A 1.426(8) . ?
C12A C14A 1.413(7) . ?
C12A C13A 1.418(7) . ?
C14A Rb2 3.662(5) 2_676 ?
O1 C1 1.234(5) . ?
O1 Rb1 3.149(3) 1_565 ?
O2 C15 1.264(13) . ?
O2 C151 1.319(12) . ?
O2 C5 1.349(7) . ?
N1 C10 1.148(6) . ?
N2 C11 1.137(5) . ?
N3 C13 1.138(6) . ?
N3 Rb1 3.015(5) 2_667 ?
N4 C14 1.136(5) . ?
N4 Rb1 3.016(4) 1_565 ?
N4 Rb2 3.038(4) 1_655 ?
C1 C2 1.436(7) . ?
C1 C8 1.533(6) . ?
C2 C7 1.392(6) . ?
C2 C3 1.404(6) . ?
C3 C4 1.366(7) . ?
C4 C5 1.383(8) . ?
C5 C6 1.386(7) . ?
C6 C7 1.368(7) . ?
C8 C9 1.394(6) . ?
C8 C12 1.395(6) . ?
C9 C10 1.418(7) . ?
C9 C11 1.426(6) . ?
C12 C14 1.415(7) . ?
C12 C13 1.436(7) . ?
C14 Rb1 3.654(4) 1_565 ?

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
O1A Rb1 N2 87.81(12) 2_766 . ?
O1A Rb1 N3 115.61(14) 2_766 2_667 ?
N2 Rb1 N3 140.51(13) . 2_667 ?
O1A Rb1 N4 77.31(10) 2_766 1_545 ?
N2 Rb1 N4 146.52(12) . 1_545 ?
N3 Rb1 N4 72.49(12) 2_667 1_545 ?
O1A Rb1 N3 91.52(13) 2_766 . ?
N2 Rb1 N3 66.18(12) . . ?
N3 Rb1 N3 81.09(14) 2_667 . ?
N4 Rb1 N3 142.75(13) 1_545 . ?
O1A Rb1 N4A 158.66(12) 2_766 2_666 ?
N2 Rb1 N4A 71.34(13) . 2_666 ?
N3 Rb1 N4A 84.50(14) 2_667 2_666 ?
N4 Rb1 N4A 117.83(12) 1_545 2_666 ?
N3 Rb1 N4A 84.34(14) . 2_666 ?
O1A Rb1 O1 104.39(9) 2_766 1_545 ?
N2 Rb1 O1 88.43(10) . 1_545 ?
N3 Rb1 O1 113.37(11) 2_667 1_545 ?
N4 Rb1 O1 67.09(10) 1_545 1_545 ?
N3 Rb1 O1 149.65(12) . 1_545 ?
N4A Rb1 O1 71.40(10) 2_666 1_545 ?
O1A Rb1 C14 83.87(9) 2_766 1_545 ?
N2 Rb1 C14 134.00(11) . 1_545 ?
N3 Rb1 C14 82.27(11) 2_667 1_545 ?
N4 Rb1 C14 16.27(10) 1_545 1_545 ?
N3 Rb1 C14 158.77(13) . 1_545 ?
N4A Rb1 C14 107.09(11) 2_666 1_545 ?
O1 Rb1 C14 50.82(10) 1_545 1_545 ?
O1A Rb1 Rb1 107.52(7) 2_766 2_667 ?
N2 Rb1 Rb1 103.86(8) . 2_667 ?
N3 Rb1 Rb1 40.70(9) 2_667 2_667 ?
N4 Rb1 Rb1 109.16(9) 1_545 2_667 ?
N3 Rb1 Rb1 40.39(9) . 2_667 ?
N4A Rb1 Rb1 82.64(8) 2_666 2_667 ?
O1 Rb1 Rb1 146.08(6) 1_545 2_667 ?
C14 Rb1 Rb1 121.80(8) 1_545 2_667 ?
O1A Rb1 Rb2 41.51(7) 2_766 1_645 ?
N2 Rb1 Rb2 128.57(9) . 1_645 ?
N3 Rb1 Rb2 83.55(11) 2_667 1_645 ?
N4 Rb1 Rb2 39.49(8) 1_545 1_645 ?
N3 Rb1 Rb2 112.99(11) . 1_645 ?
N4A Rb1 Rb2 157.02(9) 2_666 1_645 ?
O1 Rb1 Rb2 95.60(6) 1_545 1_645 ?
C14 Rb1 Rb2 51.80(7) 1_545 1_645 ?
Rb1 Rb1 Rb2 100.612(17) 2_667 1_645 ?
O1A Rb1 Rb2 140.59(7) 2_766 1_545 ?
N2 Rb1 Rb2 88.89(9) . 1_545 ?
N3 Rb1 Rb2 90.83(11) 2_667 1_545 ?
N4 Rb1 Rb2 84.28(8) 1_545 1_545 ?
N3 Rb1 Rb2 122.55(11) . 1_545 ?
N4A Rb1 Rb2 38.22(8) 2_666 1_545 ?
O1 Rb1 Rb2 36.25(6) 1_545 1_545 ?
C14 Rb1 Rb2 70.69(7) 1_545 1_545 ?
Rb1 Rb1 Rb2 111.386(18) 2_667 1_545 ?
Rb2 Rb1 Rb2 122.471(14) 1_645 1_545 ?
O1 Rb2 N2A 88.43(11) . 2_666 ?
O1 Rb2 N4A 75.24(10) . 2_676 ?
N2A Rb2 N4A 145.43(13) 2_666 2_676 ?
O1 Rb2 N3A 113.49(13) . 1_466 ?
N2A Rb2 N3A 141.47(13) 2_666 1_466 ?
N4A Rb2 N3A 72.89(12) 2_676 1_466 ?
O1 Rb2 N4 159.76(11) . 1_455 ?
N2A Rb2 N4 71.59(12) 2_666 1_455 ?
N4A Rb2 N4 119.74(11) 2_676 1_455 ?
N3A Rb2 N4 85.22(14) 1_466 1_455 ?
O1 Rb2 N3A 91.32(12) . 2_666 ?
N2A Rb2 N3A 66.19(12) 2_666 2_666 ?
N4A Rb2 N3A 142.58(13) 2_676 2_666 ?
N3A Rb2 N3A 81.35(12) 1_466 2_666 ?
N4 Rb2 N3A 83.68(13) 1_455 2_666 ?
O1 Rb2 O1A 102.89(9) . 2_676 ?
N2A Rb2 O1A 87.25(10) 2_666 2_676 ?
N4A Rb2 O1A 67.68(11) 2_676 2_676 ?
N3A Rb2 O1A 115.81(10) 1_466 2_676 ?
N4 Rb2 O1A 73.69(10) 1_455 2_676 ?
N3A Rb2 O1A 149.64(11) 2_666 2_676 ?
O1 Rb2 C14A 82.17(10) . 2_676 ?
N2A Rb2 C14A 132.96(12) 2_666 2_676 ?
N4A Rb2 C14A 16.64(11) 2_676 2_676 ?
N3A Rb2 C14A 83.11(11) 1_466 2_676 ?
N4 Rb2 C14A 108.86(11) 1_455 2_676 ?
N3A Rb2 C14A 159.11(13) 2_666 2_676 ?
O1A Rb2 C14A 51.05(10) 2_676 2_676 ?
O1 Rb2 Rb2 106.08(7) . 2_577 ?
N2A Rb2 Rb2 104.29(9) 2_666 2_577 ?
N4A Rb2 Rb2 109.41(9) 2_676 2_577 ?
N3A Rb2 Rb2 40.85(8) 1_466 2_577 ?
N4 Rb2 Rb2 82.68(8) 1_455 2_577 ?
N3A Rb2 Rb2 40.50(9) 2_666 2_577 ?
O1A Rb2 Rb2 148.97(6) 2_676 2_577 ?
C14A Rb2 Rb2 122.63(8) 2_676 2_577 ?
O1 Rb2 Rb1 140.89(7) . 1_465 ?
N2A Rb2 Rb1 89.01(9) 2_666 1_465 ?
N4A Rb2 Rb1 85.31(9) 2_676 1_465 ?
N3A Rb2 Rb1 91.88(10) 1_466 1_465 ?
N4 Rb2 Rb1 39.16(8) 1_455 1_465 ?
N3A Rb2 Rb1 122.84(11) 2_666 1_465 ?
O1A Rb2 Rb1 37.99(6) 2_676 1_465 ?
C14A Rb2 Rb1 71.45(8) 2_676 1_465 ?
Rb2 Rb2 Rb1 112.353(18) 2_577 1_465 ?
O1 Rb2 Rb1 40.03(7) . 1_565 ?
N2A Rb2 Rb1 127.50(9) 2_666 1_565 ?
N4A Rb2 Rb1 38.49(8) 2_676 1_565 ?
N3A Rb2 Rb1 83.29(10) 1_466 1_565 ?
N4 Rb2 Rb1 157.92(8) 1_455 1_565 ?
N3A Rb2 Rb1 113.01(10) 2_666 1_565 ?
O1A Rb2 Rb1 94.52(6) 2_676 1_565 ?
C14A Rb2 Rb1 51.03(8) 2_676 1_565 ?
Rb2 Rb2 Rb1 100.478(17) 2_577 1_565 ?
Rb1 Rb2 Rb1 122.472(14) 1_465 1_565 ?
C1A O1A Rb1 139.9(3) . 2_766 ?
C1A O1A Rb2 117.1(3) . 2_676 ?
Rb1 O1A Rb2 100.49(10) 2_766 2_676 ?
C5A O2A C15A 118.2(5) . . ?
C11A N2A Rb2 138.8(4) . 2_666 ?
C13A N3A Rb2 126.4(4) . 1_644 ?
C13A N3A Rb2 134.0(4) . 2_666 ?
Rb2 N3A Rb2 98.65(12) 1_644 2_666 ?
C14A N4A Rb2 114.9(4) . 2_676 ?
C14A N4A Rb1 120.2(4) . 2_666 ?
Rb2 N4A Rb1 103.29(12) 2_676 2_666 ?
O1A C1A C2A 123.5(4) . . ?
O1A C1A C8A 117.7(4) . . ?
C2A C1A C8A 118.8(4) . . ?
C7A C2A C3A 118.6(4) . . ?
C7A C2A C1A 123.1(4) . . ?
C3A C2A C1A 118.2(4) . . ?
C4A C3A C2A 120.6(4) . . ?
C3A C4A C5A 119.8(4) . . ?
O2A C5A C6A 115.5(5) . . ?
O2A C5A C4A 124.7(4) . . ?
C6A C5A C4A 119.8(4) . . ?
C7A C6A C5A 120.2(5) . . ?
C6A C7A C2A 120.9(4) . . ?
C9A C8A C12A 126.7(4) . . ?
C9A C8A C1A 118.5(4) . . ?
C12A C8A C1A 114.8(4) . . ?
C8A C9A C11A 123.3(4) . . ?
C8A C9A C10A 121.3(4) . . ?
C11A C9A C10A 115.2(4) . . ?
N1A C10A C9A 177.1(5) . . ?
N2A C11A C9A 178.0(5) . . ?
C8A C12A C14A 120.3(4) . . ?
C8A C12A C13A 124.6(4) . . ?
C14A C12A C13A 115.1(5) . . ?
N3A C13A C12A 177.5(6) . . ?
N4A C14A C12A 179.4(5) . . ?
N4A C14A Rb2 48.5(3) . 2_676 ?
C12A C14A Rb2 132.1(3) . 2_676 ?
C1 O1 Rb2 140.1(3) . . ?
C1 O1 Rb1 114.9(3) . 1_565 ?
Rb2 O1 Rb1 103.72(9) . 1_565 ?
C15 O2 C151 107.3(9) . . ?
C15 O2 C5 125.5(7) . . ?
C151 O2 C5 127.2(7) . . ?
C11 N2 Rb1 139.3(4) . . ?
C13 N3 Rb1 126.5(4) . 2_667 ?
C13 N3 Rb1 133.5(4) . . ?
Rb1 N3 Rb1 98.91(14) 2_667 . ?
C14 N4 Rb1 115.7(3) . 1_565 ?
C14 N4 Rb2 121.4(3) . 1_655 ?
Rb1 N4 Rb2 101.35(13) 1_565 1_655 ?
O1 C1 C2 124.0(4) . . ?
O1 C1 C8 116.2(4) . . ?
C2 C1 C8 119.7(4) . . ?
C7 C2 C3 117.3(4) . . ?
C7 C2 C1 123.3(4) . . ?
C3 C2 C1 119.4(4) . . ?
C4 C3 C2 121.1(5) . . ?
C3 C4 C5 120.4(5) . . ?
O2 C5 C4 120.8(5) . . ?
O2 C5 C6 119.6(5) . . ?
C4 C5 C6 119.6(5) . . ?
C7 C6 C5 119.7(5) . . ?
C6 C7 C2 121.8(4) . . ?
C9 C8 C12 127.7(4) . . ?
C9 C8 C1 118.0(4) . . ?
C12 C8 C1 114.3(4) . . ?
C8 C9 C10 121.8(4) . . ?
C8 C9 C11 122.4(4) . . ?
C10 C9 C11 115.8(4) . . ?
N1 C10 C9 177.2(5) . . ?
N2 C11 C9 178.1(5) . . ?
C8 C12 C14 120.8(4) . . ?
C8 C12 C13 124.2(4) . . ?
C14 C12 C13 115.0(4) . . ?
N3 C13 C12 177.1(5) . . ?
N4 C14 C12 178.9(5) . . ?
N4 C14 Rb1 48.1(3) . 1_565 ?
C12 C14 Rb1 131.9(3) . 1_565 ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_yak401
_database_code_depnum_ccdc_archive 'CCDC 1575020'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 K N4 O'
_chemical_formula_sum            'C15 H7 K N4 O'
_chemical_formula_weight         298.35

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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.6593(8)
_cell_length_b                   9.7349(3)
_cell_length_c                   8.2353(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.419(4)
_cell_angle_gamma                90
_cell_volume                     1415.71(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1695
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    3.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  0.608

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10611
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.009
_diffrn_reflns_theta_max         72.922
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2789
_reflns_number_gt                1752
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.3291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.10088(4) 0.36690(6) 0.03414(8) 0.0533(2) Uani 1 1 d . . . . .
O1 O 0.17822(11) 0.12364(19) 0.2388(3) 0.0596(5) Uani 1 1 d . . . . .
N1 N 0.35461(16) -0.1479(3) 0.3809(4) 0.0676(7) Uani 1 1 d . . . . .
N2 N 0.21339(14) -0.4550(2) 0.1543(3) 0.0612(7) Uani 1 1 d . . . . .
N3 N 0.06089(15) -0.3387(3) -0.0132(4) 0.0720(8) Uani 1 1 d . . . . .
N4 N 0.07414(14) 0.0971(2) -0.1127(3) 0.0573(6) Uani 1 1 d . . . . .
C1 C 0.21985(14) 0.0525(2) 0.1566(3) 0.0411(6) Uani 1 1 d . . . . .
C2 C 0.28864(14) 0.1058(2) 0.0791(3) 0.0390(6) Uani 1 1 d . . . . .
C3 C 0.30446(16) 0.2459(3) 0.0936(4) 0.0473(7) Uani 1 1 d . . . . .
C4 C 0.36707(18) 0.3004(3) 0.0205(4) 0.0555(8) Uani 1 1 d . . . . .
C5 C 0.41660(17) 0.2197(3) -0.0664(3) 0.0563(8) Uani 1 1 d . . . . .
C6 C 0.40139(17) 0.0798(4) -0.0798(4) 0.0555(8) Uani 1 1 d . . . . .
C7 C 0.33767(15) 0.0239(3) -0.0103(3) 0.0464(6) Uani 1 1 d . . . . .
C8 C 0.19617(14) -0.0965(2) 0.1287(3) 0.0394(6) Uani 1 1 d . . . . .
C9 C 0.23880(14) -0.1987(3) 0.2016(3) 0.0419(6) Uani 1 1 d . . . . .
C10 C 0.30290(17) -0.1684(3) 0.3006(4) 0.0476(7) Uani 1 1 d . . . . .
C11 C 0.22453(15) -0.3413(3) 0.1760(3) 0.0450(6) Uani 1 1 d . . . . .
C12 C 0.13081(15) -0.1119(2) 0.0340(3) 0.0426(6) Uani 1 1 d . . . . .
C13 C 0.09299(15) -0.2382(3) 0.0082(4) 0.0492(7) Uani 1 1 d . . . . .
C14 C 0.09861(15) 0.0031(3) -0.0465(3) 0.0451(6) Uani 1 1 d . . . . .
C15 C 0.4863(2) 0.2815(5) -0.1425(5) 0.0865(12) Uani 1 1 d . . . . .
H15A H 0.4724 0.3631 -0.2011 0.130 Uiso 1 1 calc R U . . .
H15B H 0.5084 0.2164 -0.2157 0.130 Uiso 1 1 calc R U . . .
H15C H 0.5223 0.3044 -0.0589 0.130 Uiso 1 1 calc R U . . .
H1 H 0.2714(18) 0.302(3) 0.159(4) 0.063(9) Uiso 1 1 d . . . . .
H2 H 0.3271(17) -0.072(3) -0.020(4) 0.058(8) Uiso 1 1 d . . . . .
H3 H 0.4348(18) 0.020(3) -0.142(4) 0.066(9) Uiso 1 1 d . . . . .
H4 H 0.3777(18) 0.395(4) 0.032(4) 0.068(9) Uiso 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
K1 O1 2.800(2) 4_565 ?
K1 N2 2.811(3) 1_565 ?
K1 N3 2.874(3) 3 ?
K1 N4 2.928(2) . ?
K1 N4 2.970(3) 4_566 ?
K1 N3 2.977(3) 1_565 ?
K1 O1 3.206(2) . ?
K1 K1 4.4383(13) 3_565 ?
K1 K1 4.7048(6) 4_565 ?
K1 K1 4.7048(6) 4_566 ?
O1 C1 1.219(3) . ?
O1 K1 2.800(2) 4_566 ?
N1 C10 1.141(4) . ?
N2 C11 1.139(3) . ?
N2 K1 2.811(3) 1_545 ?
N3 C13 1.143(3) . ?
N3 K1 2.874(3) 3 ?
N3 K1 2.977(3) 1_545 ?
N4 C14 1.149(3) . ?
N4 K1 2.970(3) 4_565 ?
C1 C2 1.471(3) . ?
C1 C8 1.526(3) . ?
C2 C7 1.391(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.370(4) . ?
C3 H1 0.97(3) . ?
C4 C5 1.380(5) . ?
C4 H4 0.95(3) . ?
C5 C6 1.392(5) . ?
C5 C15 1.510(4) . ?
C6 C7 1.378(4) . ?
C6 H3 0.97(3) . ?
C7 H2 0.95(3) . ?
C8 C9 1.382(4) . ?
C8 C12 1.397(4) . ?
C9 C10 1.421(4) . ?
C9 C11 1.426(4) . ?
C12 C13 1.414(4) . ?
C12 C14 1.418(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 N2 86.42(7) 4_565 1_565 ?
O1 K1 N3 116.23(8) 4_565 3 ?
N2 K1 N3 141.24(8) 1_565 3 ?
O1 K1 N4 75.46(7) 4_565 . ?
N2 K1 N4 144.08(7) 1_565 . ?
N3 K1 N4 74.47(7) 3 . ?
O1 K1 N4 158.24(7) 4_565 4_566 ?
N2 K1 N4 72.52(8) 1_565 4_566 ?
N3 K1 N4 84.55(8) 3 4_566 ?
N4 K1 N4 118.94(7) . 4_566 ?
O1 K1 N3 88.36(8) 4_565 1_565 ?
N2 K1 N3 67.59(7) 1_565 1_565 ?
N3 K1 N3 81.34(8) 3 1_565 ?
N4 K1 N3 140.54(8) . 1_565 ?
N4 K1 N3 88.59(8) 4_566 1_565 ?
O1 K1 O1 105.81(6) 4_565 . ?
N2 K1 O1 88.46(6) 1_565 . ?
N3 K1 O1 112.36(7) 3 . ?
N4 K1 O1 67.76(6) . . ?
N4 K1 O1 69.06(6) 4_566 . ?
N3 K1 O1 151.60(7) 1_565 . ?
O1 K1 K1 105.49(5) 4_565 3_565 ?
N2 K1 K1 104.43(5) 1_565 3_565 ?
N3 K1 K1 41.53(5) 3 3_565 ?
N4 K1 K1 110.15(5) . 3_565 ?
N4 K1 K1 85.52(5) 4_566 3_565 ?
N3 K1 K1 39.80(5) 1_565 3_565 ?
O1 K1 K1 146.75(4) . 3_565 ?
O1 K1 K1 41.62(4) 4_565 4_565 ?
N2 K1 K1 127.01(6) 1_565 4_565 ?
N3 K1 K1 84.70(7) 3 4_565 ?
N4 K1 K1 37.41(5) . 4_565 ?
N4 K1 K1 156.19(5) 4_566 4_565 ?
N3 K1 K1 110.65(7) 1_565 4_565 ?
O1 K1 K1 95.74(4) . 4_565 ?
K1 K1 K1 100.178(16) 3_565 4_565 ?
O1 K1 K1 141.20(4) 4_565 4_566 ?
N2 K1 K1 89.69(6) 1_565 4_566 ?
N3 K1 K1 90.00(7) 3 4_566 ?
N4 K1 K1 85.79(6) . 4_566 ?
N4 K1 K1 36.79(5) 4_566 4_566 ?
N3 K1 K1 125.37(7) 1_565 4_566 ?
O1 K1 K1 35.45(4) . 4_566 ?
K1 K1 K1 112.843(16) 3_565 4_566 ?
K1 K1 K1 122.14(3) 4_565 4_566 ?
C1 O1 K1 143.24(18) . 4_566 ?
C1 O1 K1 112.59(17) . . ?
K1 O1 K1 102.93(6) 4_566 . ?
C11 N2 K1 140.9(2) . 1_545 ?
C13 N3 K1 125.6(2) . 3 ?
C13 N3 K1 133.4(2) . 1_545 ?
K1 N3 K1 98.66(8) 3 1_545 ?
C14 N4 K1 117.4(2) . . ?
C14 N4 K1 119.8(2) . 4_565 ?
K1 N4 K1 105.81(8) . 4_565 ?
O1 C1 C2 122.9(2) . . ?
O1 C1 C8 117.3(2) . . ?
C2 C1 C8 119.8(2) . . ?
C7 C2 C3 118.6(2) . . ?
C7 C2 C1 123.1(2) . . ?
C3 C2 C1 118.2(2) . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H1 121.1(18) . . ?
C2 C3 H1 118.7(18) . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119(2) . . ?
C5 C4 H4 119(2) . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 C15 120.6(3) . . ?
C6 C5 C15 121.0(3) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H3 118.9(18) . . ?
C5 C6 H3 120.4(18) . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 H2 120.8(18) . . ?
C2 C7 H2 118.7(18) . . ?
C9 C8 C12 127.6(2) . . ?
C9 C8 C1 118.1(2) . . ?
C12 C8 C1 114.3(2) . . ?
C8 C9 C10 121.9(2) . . ?
C8 C9 C11 122.8(2) . . ?
C10 C9 C11 115.2(2) . . ?
N1 C10 C9 178.1(3) . . ?
N2 C11 C9 179.5(3) . . ?
C8 C12 C13 124.4(2) . . ?
C8 C12 C14 120.2(2) . . ?
C13 C12 C14 115.4(2) . . ?
N3 C13 C12 178.4(3) . . ?
N4 C14 C12 178.5(3) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
K1 O1 C1 C2 -132.5(2) 4_566 . . . ?
K1 O1 C1 C2 63.3(3) . . . . ?
K1 O1 C1 C8 50.3(4) 4_566 . . . ?
K1 O1 C1 C8 -113.8(2) . . . . ?
O1 C1 C2 C7 177.8(3) . . . . ?
C8 C1 C2 C7 -5.1(4) . . . . ?
O1 C1 C2 C3 -3.5(4) . . . . ?
C8 C1 C2 C3 173.6(2) . . . . ?
C7 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 C4 -178.7(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C3 C4 C5 C15 -178.5(3) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C15 C5 C6 C7 -179.9(3) . . . . ?
C5 C6 C7 C2 -2.1(4) . . . . ?
C3 C2 C7 C6 1.5(4) . . . . ?
C1 C2 C7 C6 -179.9(3) . . . . ?
O1 C1 C8 C9 -111.0(3) . . . . ?
C2 C1 C8 C9 71.7(3) . . . . ?
O1 C1 C8 C12 67.0(3) . . . . ?
C2 C1 C8 C12 -110.2(3) . . . . ?
C12 C8 C9 C10 -177.5(3) . . . . ?
C1 C8 C9 C10 0.2(4) . . . . ?
C12 C8 C9 C11 6.1(4) . . . . ?
C1 C8 C9 C11 -176.1(2) . . . . ?
C9 C8 C12 C13 5.8(4) . . . . ?
C1 C8 C12 C13 -172.0(2) . . . . ?
C9 C8 C12 C14 -173.1(3) . . . . ?
C1 C8 C12 C14 9.1(4) . . . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_yak400
_database_code_depnum_ccdc_archive 'CCDC 1575016'
_audit_update_record             
;
2017-10-17 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 N4 Na O3'
_chemical_formula_sum            'C15 H9 N4 Na O3'
_chemical_formula_weight         316.25

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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.1923(3)
_cell_length_b                   18.4186(6)
_cell_length_c                   6.8235(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.312(2)
_cell_angle_gamma                90
_cell_volume                     1531.07(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    856
_cell_measurement_theta_min      4
_cell_measurement_theta_max      65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    1.071
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_T_max  0.739

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            11464
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.628
_diffrn_reflns_theta_max         68.948
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             2728
_reflns_number_gt                1578
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.51406(7) 0.20037(5) 0.34398(13) 0.0507(3) Uani 1 1 d . . . . .
O1 O 0.36577(13) 0.17638(8) 0.1362(3) 0.0664(5) Uani 1 1 d . . . . .
O2 O -0.12005(12) 0.26716(9) -0.1155(3) 0.0646(5) Uani 1 1 d . . . . .
O3 O 0.63281(15) 0.24814(11) 0.0968(3) 0.0512(4) Uani 1 1 d . . . . .
N1 N 0.42724(18) 0.15038(12) -0.3653(4) 0.0745(7) Uani 1 1 d . . . . .
N2 N 0.40795(17) -0.07968(12) -0.2793(3) 0.0619(6) Uani 1 1 d . . . . .
N3 N 0.30077(17) -0.12554(12) 0.1524(3) 0.0649(6) Uani 1 1 d . . . . .
N4 N 0.1701(2) 0.04957(13) 0.4661(4) 0.0883(8) Uani 1 1 d . . . . .
C1 C 0.28960(17) 0.14138(11) 0.0639(3) 0.0418(5) Uani 1 1 d . . . . .
C2 C 0.18317(16) 0.17353(10) 0.0098(3) 0.0370(5) Uani 1 1 d . . . . .
C3 C 0.09095(17) 0.13191(13) -0.0452(3) 0.0446(6) Uani 1 1 d . . . . .
C4 C -0.00874(19) 0.16492(13) -0.0827(4) 0.0495(6) Uani 1 1 d . . . . .
C5 C -0.01802(17) 0.23980(12) -0.0730(3) 0.0457(6) Uani 1 1 d . . . . .
C6 C 0.07293(18) 0.28197(13) -0.0248(3) 0.0439(6) Uani 1 1 d . . . . .
C7 C 0.17221(18) 0.24875(11) 0.0174(3) 0.0402(5) Uani 1 1 d . . . . .
C8 C 0.30973(16) 0.06119(10) 0.0245(3) 0.0392(5) Uani 1 1 d . . . . .
C9 C 0.36464(16) 0.04679(11) -0.1458(3) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.39881(18) 0.10452(13) -0.2664(4) 0.0508(6) Uani 1 1 d . . . . .
C11 C 0.38847(17) -0.02370(13) -0.2167(4) 0.0450(6) Uani 1 1 d . . . . .
C12 C 0.27398(17) 0.01182(11) 0.1623(3) 0.0438(6) Uani 1 1 d . . . . .
C13 C 0.29075(17) -0.06401(13) 0.1518(4) 0.0446(6) Uani 1 1 d . . . . .
C14 C 0.2169(2) 0.03422(12) 0.3301(4) 0.0569(7) Uani 1 1 d . . . . .
C15 C -0.1341(2) 0.34432(14) -0.1105(5) 0.0694(8) Uani 1 1 d . . . . .
H15A H -0.1151 0.3620 0.0188 0.104 Uiso 1 1 calc R U . . .
H15B H -0.2092 0.3561 -0.1437 0.104 Uiso 1 1 calc R U . . .
H15C H -0.0874 0.3666 -0.2032 0.104 Uiso 1 1 calc R U . . .
H1 H 0.0713(17) 0.3333(13) -0.016(3) 0.050(6) Uiso 1 1 d . . . . .
H2 H 0.2343(18) 0.2783(12) 0.054(3) 0.046(6) Uiso 1 1 d . . . . .
H3 H 0.0967(18) 0.0790(15) -0.057(4) 0.061(7) Uiso 1 1 d . . . . .
H4 H -0.074(2) 0.1371(13) -0.112(4) 0.064(7) Uiso 1 1 d . . . . .
H8 H 0.678(3) 0.219(2) 0.052(6) 0.112(13) Uiso 1 1 d . . . . .
H9 H 0.670(3) 0.280(2) 0.158(6) 0.121(15) Uiso 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
Na1 O1 2.2952(19) . ?
Na1 O3 2.4019(19) 4_566 ?
Na1 O3 2.4316(18) . ?
Na1 N1 2.464(2) 1_556 ?
Na1 N2 2.465(2) 3_655 ?
Na1 Na1 3.8706(8) 4_565 ?
Na1 Na1 3.8706(8) 4_566 ?
O1 C1 1.218(3) . ?
O2 C5 1.362(3) . ?
O2 C15 1.432(3) . ?
O3 Na1 2.4020(19) 4_565 ?
O3 H8 0.84(4) . ?
O3 H9 0.84(4) . ?
N1 C10 1.144(3) . ?
N1 Na1 2.464(2) 1_554 ?
N2 C11 1.144(3) . ?
N2 Na1 2.465(2) 3_655 ?
N3 C13 1.140(3) . ?
N4 C14 1.144(3) . ?
C1 C2 1.460(3) . ?
C1 C8 1.523(3) . ?
C2 C7 1.393(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.98(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.96(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.376(3) . ?
C6 H1 0.95(2) . ?
C7 H2 0.96(2) . ?
C8 C9 1.390(3) . ?
C8 C12 1.390(3) . ?
C9 C10 1.417(3) . ?
C9 C11 1.420(3) . ?
C12 C13 1.414(3) . ?
C12 C14 1.425(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na1 O3 163.07(7) . 4_566 ?
O1 Na1 O3 96.74(7) . . ?
O3 Na1 O3 89.82(6) 4_566 . ?
O1 Na1 N1 94.13(8) . 1_556 ?
O3 Na1 N1 80.53(8) 4_566 1_556 ?
O3 Na1 N1 168.74(8) . 1_556 ?
O1 Na1 N2 90.90(7) . 3_655 ?
O3 Na1 N2 105.01(8) 4_566 3_655 ?
O3 Na1 N2 87.56(7) . 3_655 ?
N1 Na1 N2 89.34(8) 1_556 3_655 ?
O1 Na1 Na1 64.81(5) . 4_565 ?
O3 Na1 Na1 115.16(6) 4_566 4_565 ?
O3 Na1 Na1 36.53(5) . 4_565 ?
N1 Na1 Na1 154.32(6) 1_556 4_565 ?
N2 Na1 Na1 104.74(6) 3_655 4_565 ?
O1 Na1 Na1 127.41(5) . 4_566 ?
O3 Na1 Na1 37.06(4) 4_566 4_566 ?
O3 Na1 Na1 117.50(6) . 4_566 ?
N1 Na1 Na1 56.75(6) 1_556 4_566 ?
N2 Na1 Na1 126.69(6) 3_655 4_566 ?
Na1 Na1 Na1 123.63(4) 4_565 4_566 ?
C1 O1 Na1 157.02(16) . . ?
C5 O2 C15 118.10(19) . . ?
Na1 O3 Na1 106.41(8) 4_565 . ?
Na1 O3 H8 112(3) 4_565 . ?
Na1 O3 H8 116(2) . . ?
Na1 O3 H9 113(3) 4_565 . ?
Na1 O3 H9 103(3) . . ?
H8 O3 H9 106(3) . . ?
C10 N1 Na1 154.3(2) . 1_554 ?
C11 N2 Na1 165.2(2) . 3_655 ?
O1 C1 C2 122.87(19) . . ?
O1 C1 C8 117.32(18) . . ?
C2 C1 C8 119.78(18) . . ?
C7 C2 C3 118.5(2) . . ?
C7 C2 C1 118.66(19) . . ?
C3 C2 C1 122.81(19) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.4(14) . . ?
C2 C3 H3 120.4(14) . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 121.4(15) . . ?
C5 C4 H4 118.2(14) . . ?
O2 C5 C6 124.0(2) . . ?
O2 C5 C4 115.7(2) . . ?
C6 C5 C4 120.3(2) . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 H1 116.8(13) . . ?
C5 C6 H1 123.9(13) . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 H2 118.8(13) . . ?
C2 C7 H2 119.9(13) . . ?
C9 C8 C12 127.96(19) . . ?
C9 C8 C1 114.78(17) . . ?
C12 C8 C1 117.25(19) . . ?
C8 C9 C10 120.33(19) . . ?
C8 C9 C11 124.87(18) . . ?
C10 C9 C11 114.78(19) . . ?
N1 C10 C9 179.0(3) . . ?
N2 C11 C9 178.0(2) . . ?
C8 C12 C13 124.2(2) . . ?
C8 C12 C14 122.05(19) . . ?
C13 C12 C14 113.76(19) . . ?
N3 C13 C12 176.2(2) . . ?
N4 C14 C12 177.5(3) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Na1 O1 C1 C2 139.2(3) . . . . ?
Na1 O1 C1 C8 -42.6(5) . . . . ?
O1 C1 C2 C7 8.5(3) . . . . ?
C8 C1 C2 C7 -169.68(19) . . . . ?
O1 C1 C2 C3 -170.1(2) . . . . ?
C8 C1 C2 C3 11.7(3) . . . . ?
C7 C2 C3 C4 -2.7(3) . . . . ?
C1 C2 C3 C4 175.9(2) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C15 O2 C5 C6 0.2(3) . . . . ?
C15 O2 C5 C4 -179.1(2) . . . . ?
C3 C4 C5 O2 179.1(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
O2 C5 C6 C7 179.4(2) . . . . ?
C4 C5 C6 C7 -1.3(3) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C3 C2 C7 C6 1.1(3) . . . . ?
C1 C2 C7 C6 -177.6(2) . . . . ?
O1 C1 C8 C9 -80.2(3) . . . . ?
C2 C1 C8 C9 98.1(2) . . . . ?
O1 C1 C8 C12 98.5(2) . . . . ?
C2 C1 C8 C12 -83.2(3) . . . . ?
C12 C8 C9 C10 -177.6(2) . . . . ?
C1 C8 C9 C10 0.9(3) . . . . ?
C12 C8 C9 C11 4.2(4) . . . . ?
C1 C8 C9 C11 -177.3(2) . . . . ?
C9 C8 C12 C13 1.4(4) . . . . ?
C1 C8 C12 C13 -177.1(2) . . . . ?
C9 C8 C12 C14 -179.1(2) . . . . ?
C1 C8 C12 C14 2.4(3) . . . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_yak426
_database_code_depnum_ccdc_archive 'CCDC 1575041'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H4 Br K N4 O'
_chemical_formula_sum            'C14 H4 Br K N4 O'
_chemical_formula_weight         363.22

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'
Br Br -0.6763 1.2805 '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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   18.4561(9)
_cell_length_b                   9.6685(4)
_cell_length_c                   8.1421(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.306(3)
_cell_angle_gamma                90
_cell_volume                     1419.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1563
_cell_measurement_theta_min      4
_cell_measurement_theta_max      65

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    6.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            9012
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.905
_diffrn_reflns_theta_max         66.566
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2456
_reflns_number_gt                1755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2455
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1452
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.09925(6) 0.86779(11) 0.07366(14) 0.0535(3) Uani 1 1 d . . . . .
Br1 Br 0.50170(3) 0.77791(7) 0.07042(7) 0.0702(3) Uani 1 1 d . . . . .
O1 O 0.17743(19) 0.6321(3) 0.3111(5) 0.0587(9) Uani 1 1 d . . . . .
N1 N 0.0721(3) 0.5986(5) -0.0851(6) 0.0586(11) Uani 1 1 d . . . . .
N2 N 0.0593(3) 0.1605(5) 0.0167(7) 0.0730(14) Uani 1 1 d . . . . .
N3 N 0.2097(2) 0.0447(4) 0.2509(6) 0.0593(11) Uani 1 1 d . . . . .
N4 N 0.3481(3) 0.3568(5) 0.5478(7) 0.0639(12) Uani 1 1 d . . . . .
C1 C 0.2182(2) 0.5558(4) 0.2509(6) 0.0447(11) Uani 1 1 d . . . . .
C2 C 0.1935(2) 0.4063(4) 0.2156(6) 0.0391(10) Uani 1 1 d . . . . .
C3 C 0.1284(3) 0.3888(4) 0.0927(6) 0.0445(11) Uani 1 1 d . . . . .
C4 C 0.2355(2) 0.3039(4) 0.3112(6) 0.0425(10) Uani 1 1 d . . . . .
C5 C 0.0961(3) 0.5056(5) -0.0058(6) 0.0447(10) Uani 1 1 d . . . . .
C6 C 0.0908(3) 0.2630(5) 0.0495(7) 0.0530(12) Uani 1 1 d . . . . .
C7 C 0.2207(3) 0.1596(5) 0.2791(6) 0.0457(11) Uani 1 1 d . . . . .
C8 C 0.2975(3) 0.3347(5) 0.4417(7) 0.0461(11) Uani 1 1 d . . . . .
C9 C 0.2865(2) 0.6051(4) 0.2055(6) 0.0400(10) Uani 1 1 d . . . . .
C10 C 0.3041(3) 0.7455(5) 0.2249(6) 0.0465(11) Uani 1 1 d . . . . .
C11 C 0.3671(3) 0.7981(5) 0.1821(7) 0.0521(12) Uani 1 1 d . . . . .
C12 C 0.4131(3) 0.7081(5) 0.1233(6) 0.0507(12) Uani 1 1 d . . . . .
C13 C 0.3985(3) 0.5693(5) 0.1030(7) 0.0527(12) Uani 1 1 d . . . . .
C14 C 0.3341(3) 0.5184(5) 0.1416(6) 0.0477(11) Uani 1 1 d . . . . .
H1 H 0.272(3) 0.802(5) 0.271(6) 0.045(12) Uiso 1 1 d . . . . .
H4 H 0.323(2) 0.418(5) 0.137(5) 0.035(11) Uiso 1 1 d . . . . .
H5 H 0.434(3) 0.511(6) 0.074(6) 0.055(14) Uiso 1 1 d . . . . .
H9 H 0.375(3) 0.895(7) 0.200(7) 0.068(16) Uiso 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
K1 N3 2.813(4) 1_565 ?
K1 O1 2.823(3) 4_575 ?
K1 N2 2.873(5) 3_565 ?
K1 N1 2.901(5) . ?
K1 N2 2.937(5) 1_565 ?
K1 N1 2.945(5) 4_576 ?
K1 O1 3.134(4) . ?
K1 K1 4.419(2) 3_575 ?
K1 K1 4.6649(10) 4_575 ?
K1 K1 4.6649(10) 4_576 ?
Br1 C12 1.901(5) . ?
O1 C1 1.228(5) . ?
O1 K1 2.823(3) 4_576 ?
N1 C5 1.140(6) . ?
N1 K1 2.945(5) 4_575 ?
N2 C6 1.152(7) . ?
N2 K1 2.873(5) 3_565 ?
N2 K1 2.936(5) 1_545 ?
N3 C7 1.144(6) . ?
N3 K1 2.813(4) 1_545 ?
N4 C8 1.149(7) . ?
C1 C9 1.467(6) . ?
C1 C2 1.524(6) . ?
C2 C4 1.389(6) . ?
C2 C3 1.400(6) . ?
C3 C6 1.407(7) . ?
C3 C5 1.439(7) . ?
C4 C8 1.418(7) . ?
C4 C7 1.434(7) . ?
C9 C14 1.393(6) . ?
C9 C10 1.396(6) . ?
C10 C11 1.380(7) . ?
C11 C12 1.372(8) . ?
C12 C13 1.372(7) . ?
C13 C14 1.382(7) . ?

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
N3 K1 O1 87.53(12) 1_565 4_575 ?
N3 K1 N2 140.91(14) 1_565 3_565 ?
O1 K1 N2 117.59(14) 4_575 3_565 ?
N3 K1 N1 144.26(13) 1_565 . ?
O1 K1 N1 74.38(11) 4_575 . ?
N2 K1 N1 74.38(14) 3_565 . ?
N3 K1 N2 67.99(13) 1_565 1_565 ?
O1 K1 N2 91.82(13) 4_575 1_565 ?
N2 K1 N2 80.99(15) 3_565 1_565 ?
N1 K1 N2 141.29(14) . 1_565 ?
N3 K1 N1 72.49(13) 1_565 4_576 ?
O1 K1 N1 158.74(13) 4_575 4_576 ?
N2 K1 N1 83.29(15) 3_565 4_576 ?
N1 K1 N1 118.11(11) . 4_576 ?
N2 K1 N1 87.43(15) 1_565 4_576 ?
N3 K1 O1 86.43(11) 1_565 . ?
O1 K1 O1 103.01(9) 4_575 . ?
N2 K1 O1 113.48(12) 3_565 . ?
N1 K1 O1 68.63(11) . . ?
N2 K1 O1 149.93(13) 1_565 . ?
N1 K1 O1 69.31(11) 4_576 . ?
N3 K1 K1 104.81(9) 1_565 3_575 ?
O1 K1 K1 108.80(8) 4_575 3_575 ?
N2 K1 K1 41.02(10) 3_565 3_575 ?
N1 K1 K1 110.09(10) . 3_575 ?
N2 K1 K1 39.96(9) 1_565 3_575 ?
N1 K1 K1 83.93(9) 4_576 3_575 ?
O1 K1 K1 146.53(7) . 3_575 ?
N3 K1 K1 127.59(9) 1_565 4_575 ?
O1 K1 K1 40.90(7) 4_575 4_575 ?
N2 K1 K1 85.38(12) 3_565 4_575 ?
N1 K1 K1 37.39(9) . 4_575 ?
N2 K1 K1 112.30(12) 1_565 4_575 ?
N1 K1 K1 155.37(10) 4_576 4_575 ?
O1 K1 K1 95.60(7) . 4_575 ?
K1 K1 K1 101.53(3) 3_575 4_575 ?
N3 K1 K1 89.08(9) 1_565 4_576 ?
O1 K1 K1 139.14(8) 4_575 4_576 ?
N2 K1 K1 89.29(11) 3_565 4_576 ?
N1 K1 K1 85.33(10) . 4_576 ?
N2 K1 K1 124.17(12) 1_565 4_576 ?
N1 K1 K1 36.75(9) 4_576 4_576 ?
O1 K1 K1 36.13(6) . 4_576 ?
K1 K1 K1 111.42(3) 3_575 4_576 ?
K1 K1 K1 121.55(4) 4_575 4_576 ?
C1 O1 K1 139.3(3) . 4_576 ?
C1 O1 K1 115.6(3) . . ?
K1 O1 K1 102.96(10) 4_576 . ?
C5 N1 K1 116.5(4) . . ?
C5 N1 K1 119.9(3) . 4_575 ?
K1 N1 K1 105.87(14) . 4_575 ?
C6 N2 K1 125.3(4) . 3_565 ?
C6 N2 K1 134.0(4) . 1_545 ?
K1 N2 K1 99.02(15) 3_565 1_545 ?
C7 N3 K1 140.5(4) . 1_545 ?
O1 C1 C9 122.5(4) . . ?
O1 C1 C2 117.4(4) . . ?
C9 C1 C2 120.0(4) . . ?
C4 C2 C3 127.2(4) . . ?
C4 C2 C1 117.5(4) . . ?
C3 C2 C1 115.2(4) . . ?
C2 C3 C6 125.8(4) . . ?
C2 C3 C5 119.6(4) . . ?
C6 C3 C5 114.5(4) . . ?
C2 C4 C8 122.4(4) . . ?
C2 C4 C7 122.0(4) . . ?
C8 C4 C7 115.6(4) . . ?
N1 C5 C3 178.2(5) . . ?
N2 C6 C3 178.6(6) . . ?
N3 C7 C4 178.6(5) . . ?
N4 C8 C4 178.6(5) . . ?
C14 C9 C10 118.6(4) . . ?
C14 C9 C1 122.8(4) . . ?
C10 C9 C1 118.6(4) . . ?
C11 C10 C9 121.1(5) . . ?
C12 C11 C10 118.2(4) . . ?
C11 C12 C13 122.8(5) . . ?
C11 C12 Br1 118.7(4) . . ?
C13 C12 Br1 118.5(4) . . ?
C12 C13 C14 118.5(5) . . ?
C13 C14 C9 120.7(4) . . ?

_refine_diff_density_max         0.664
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_yak425
_database_code_depnum_ccdc_archive 'CCDC 1575040'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 Br N4 Na O2'
_chemical_formula_sum            'C14 H6 Br N4 Na O2'
_chemical_formula_weight         365.13

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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4244(3)
_cell_length_b                   27.3787(10)
_cell_length_c                   6.0595(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.960(2)
_cell_angle_gamma                90
_cell_volume                     1503.25(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2568
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    4.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'

_diffrn_reflns_number            9569
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.881
_diffrn_reflns_theta_max         72.955
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2790
_reflns_number_gt                2341
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²+0.3884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0049(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2790
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.73395(5) 0.01031(2) 0.18223(9) 0.0816(2) Uani 1 1 d . . . . .
Na1 Na 0.88725(12) 0.20998(4) -0.54773(18) 0.0471(3) Uani 1 1 d . . . . .
O1 O 1.1131(2) 0.16015(9) -0.3584(4) 0.0560(5) Uani 1 1 d . . . . .
O2 O 0.7818(3) 0.21507(10) -0.2331(4) 0.0544(5) Uani 1 1 d . . . . .
N1 N 1.4151(3) 0.08219(12) -0.3970(5) 0.0692(8) Uani 1 1 d . . . . .
N2 N 1.6896(3) 0.15949(10) 0.1880(5) 0.0577(7) Uani 1 1 d . . . . .
N3 N 1.4983(3) 0.21888(14) 0.4973(6) 0.0790(10) Uani 1 1 d . . . . .
N4 N 1.0368(3) 0.22032(10) 0.1808(4) 0.0503(6) Uani 1 1 d . . . . .
C1 C 1.1517(3) 0.14056(9) -0.1714(4) 0.0400(6) Uani 1 1 d . . . . .
C2 C 1.2998(3) 0.15549(9) -0.0065(4) 0.0377(5) Uani 1 1 d . . . . .
C3 C 1.4260(3) 0.13705(9) -0.0480(5) 0.0408(6) Uani 1 1 d . . . . .
C4 C 1.2877(3) 0.18737(10) 0.1672(5) 0.0415(6) Uani 1 1 d . . . . .
C5 C 1.4197(3) 0.10617(11) -0.2408(5) 0.0475(6) Uani 1 1 d . . . . .
C6 C 1.5712(3) 0.14951(10) 0.0866(5) 0.0439(6) Uani 1 1 d . . . . .
C7 C 1.4065(3) 0.20433(12) 0.3473(5) 0.0506(7) Uani 1 1 d . . . . .
C8 C 1.1486(3) 0.20501(9) 0.1754(4) 0.0408(6) Uani 1 1 d . . . . .
C9 C 1.0580(3) 0.10563(9) -0.0892(5) 0.0410(6) Uani 1 1 d . . . . .
C10 C 0.9180(3) 0.09432(10) -0.2326(5) 0.0469(6) Uani 1 1 d . . . . .
H10 H 0.8892 0.1065 -0.3816 0.056 Uiso 1 1 calc R U . . .
C11 C 0.8225(3) 0.06524(11) -0.1543(6) 0.0567(8) Uani 1 1 d . . . . .
H11 H 0.7295 0.0577 -0.2493 0.068 Uiso 1 1 calc R U . . .
C12 C 0.8676(4) 0.04743(11) 0.0685(6) 0.0546(7) Uani 1 1 d . . . . .
C13 C 1.0067(4) 0.05614(11) 0.2090(6) 0.0558(7) Uani 1 1 d . . . . .
H13 H 1.0363 0.0426 0.3552 0.067 Uiso 1 1 calc R U . . .
C14 C 1.1023(3) 0.08533(10) 0.1302(5) 0.0487(7) Uani 1 1 d . . . . .
H14 H 1.1967 0.0915 0.2242 0.058 Uiso 1 1 calc R U . . .
H21 H 0.794(5) 0.1979(19) -0.144(9) 0.083(17) Uiso 1 1 d . . . . .
H22 H 0.702(5) 0.2183(14) -0.280(7) 0.060(12) Uiso 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
Br1 C12 1.890(3) . ?
Na1 O2 2.384(3) . ?
Na1 O2 2.418(3) 4_565 ?
Na1 N4 2.459(3) 1_554 ?
Na1 N2 2.511(3) 1_454 ?
Na1 O1 2.523(2) . ?
Na1 N4 2.544(3) 4_565 ?
Na1 Na1 3.7393(13) 4_565 ?
Na1 Na1 3.7393(13) 4_566 ?
O1 C1 1.216(3) . ?
O2 Na1 2.418(3) 4_566 ?
O2 H21 0.70(5) . ?
O2 H22 0.73(4) . ?
N1 C5 1.143(4) . ?
N2 C6 1.149(4) . ?
N2 Na1 2.511(3) 1_656 ?
N3 C7 1.141(4) . ?
N4 C8 1.143(4) . ?
N4 Na1 2.459(3) 1_556 ?
N4 Na1 2.544(3) 4_566 ?
C1 C9 1.478(4) . ?
C1 C2 1.532(3) . ?
C2 C3 1.377(4) . ?
C2 C4 1.396(4) . ?
C3 C6 1.428(4) . ?
C3 C5 1.430(4) . ?
C4 C7 1.410(4) . ?
C4 C8 1.410(4) . ?
C9 C14 1.395(4) . ?
C9 C10 1.401(3) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(5) . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Na1 O2 96.52(9) . 4_565 ?
O2 Na1 N4 165.88(9) . 1_554 ?
O2 Na1 N4 80.17(9) 4_565 1_554 ?
O2 Na1 N2 98.22(10) . 1_454 ?
O2 Na1 N2 91.89(10) 4_565 1_454 ?
N4 Na1 N2 95.61(10) 1_554 1_454 ?
O2 Na1 O1 98.81(9) . . ?
O2 Na1 O1 149.05(9) 4_565 . ?
N4 Na1 O1 78.43(8) 1_554 . ?
N2 Na1 O1 112.18(9) 1_454 . ?
O2 Na1 N4 79.11(9) . 4_565 ?
O2 Na1 N4 73.24(9) 4_565 4_565 ?
N4 Na1 N4 86.81(9) 1_554 4_565 ?
N2 Na1 N4 164.34(10) 1_454 4_565 ?
O1 Na1 N4 83.47(9) . 4_565 ?
O2 Na1 Na1 134.96(8) . 4_565 ?
O2 Na1 Na1 38.53(7) 4_565 4_565 ?
N4 Na1 Na1 42.51(6) 1_554 4_565 ?
N2 Na1 Na1 88.35(7) 1_454 4_565 ?
O1 Na1 Na1 119.82(6) . 4_565 ?
N4 Na1 Na1 83.00(7) 4_565 4_565 ?
O2 Na1 Na1 39.19(6) . 4_566 ?
O2 Na1 Na1 77.73(8) 4_565 4_566 ?
N4 Na1 Na1 127.03(7) 1_554 4_566 ?
N2 Na1 Na1 132.39(7) 1_454 4_566 ?
O1 Na1 Na1 97.84(6) . 4_566 ?
N4 Na1 Na1 40.77(6) 4_565 4_566 ?
Na1 Na1 Na1 108.24(5) 4_565 4_566 ?
C1 O1 Na1 131.4(2) . . ?
Na1 O2 Na1 102.29(9) . 4_566 ?
Na1 O2 H21 124(4) . . ?
Na1 O2 H21 105(4) 4_566 . ?
Na1 O2 H22 108(3) . . ?
Na1 O2 H22 109(3) 4_566 . ?
H21 O2 H22 108(5) . . ?
C6 N2 Na1 155.9(2) . 1_656 ?
C8 N4 Na1 132.8(2) . 1_556 ?
C8 N4 Na1 129.5(2) . 4_566 ?
Na1 N4 Na1 96.73(9) 1_556 4_566 ?
O1 C1 C9 123.1(2) . . ?
O1 C1 C2 118.4(2) . . ?
C9 C1 C2 118.3(2) . . ?
C3 C2 C4 128.4(2) . . ?
C3 C2 C1 117.4(2) . . ?
C4 C2 C1 114.2(2) . . ?
C2 C3 C6 123.2(2) . . ?
C2 C3 C5 121.4(2) . . ?
C6 C3 C5 115.2(2) . . ?
C2 C4 C7 125.2(2) . . ?
C2 C4 C8 120.7(2) . . ?
C7 C4 C8 114.1(2) . . ?
N1 C5 C3 178.8(4) . . ?
N2 C6 C3 177.6(3) . . ?
N3 C7 C4 177.1(3) . . ?
N4 C8 C4 178.5(3) . . ?
C14 C9 C10 119.2(3) . . ?
C14 C9 C1 121.9(2) . . ?
C10 C9 C1 118.8(2) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 118.9(3) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 Br1 119.1(3) . . ?
C11 C12 Br1 119.2(2) . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?

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
Na1 O1 C1 C9 54.4(4) . . . . ?
Na1 O1 C1 C2 -121.2(2) . . . . ?
O1 C1 C2 C3 -77.0(3) . . . . ?
C9 C1 C2 C3 107.2(3) . . . . ?
O1 C1 C2 C4 102.0(3) . . . . ?
C9 C1 C2 C4 -73.8(3) . . . . ?
C4 C2 C3 C6 -1.4(5) . . . . ?
C1 C2 C3 C6 177.5(2) . . . . ?
C4 C2 C3 C5 -177.2(3) . . . . ?
C1 C2 C3 C5 1.6(4) . . . . ?
C3 C2 C4 C7 -4.8(5) . . . . ?
C1 C2 C4 C7 176.3(3) . . . . ?
C3 C2 C4 C8 176.0(3) . . . . ?
C1 C2 C4 C8 -2.9(4) . . . . ?
O1 C1 C9 C14 -177.1(3) . . . . ?
C2 C1 C9 C14 -1.5(4) . . . . ?
O1 C1 C9 C10 0.1(4) . . . . ?
C2 C1 C9 C10 175.6(2) . . . . ?
C14 C9 C10 C11 2.9(4) . . . . ?
C1 C9 C10 C11 -174.3(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C10 C11 C12 C13 -3.0(5) . . . . ?
C10 C11 C12 Br1 176.8(2) . . . . ?
C11 C12 C13 C14 3.1(5) . . . . ?
Br1 C12 C13 C14 -176.8(2) . . . . ?
C12 C13 C14 C9 -0.1(5) . . . . ?
C10 C9 C14 C13 -2.9(4) . . . . ?
C1 C9 C14 C13 174.3(3) . . . . ?

_refine_diff_density_max         0.740
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-4

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

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1kqyrz
_database_code_depnum_ccdc_archive 'CCDC 1452032'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.6b01040 2016
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'Potassium 2-benzoyl-1,1,3,3-tetracyanopropenide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 K N4 O2'
_chemical_formula_sum            'C14 H7 K N4 O2'
_chemical_formula_weight         302.34

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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.2144(2)
_cell_length_b                   10.5903(4)
_cell_length_c                   17.2090(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.5490(10)
_cell_angle_gamma                90
_cell_volume                     1495.58(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_absorpt_coefficient_mu    3.200
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10136
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.905
_diffrn_reflns_theta_max         72.926
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10136
_reflns_number_gt                7054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10136
_refine_ls_number_parameters     198
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1586
_refine_ls_R_factor_gt           0.1413
_refine_ls_wR_factor_ref         0.2161
_refine_ls_wR_factor_gt          0.2092
_refine_ls_goodness_of_fit_ref   1.356
_refine_ls_restrained_S_all      1.356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.5160(2) 0.33665(14) 0.55720(7) 0.0640(6) Uani 1 1 d . . . . .
O1 O 0.5608(6) 0.1758(6) 0.4377(2) 0.0734(15) Uani 1 1 d . . . . .
O2 O 0.2636(8) 0.4888(6) 0.5012(3) 0.0786(16) Uani 1 1 d D . . . .
N1 N 0.6639(10) -0.1699(7) 0.3512(4) 0.082(2) Uani 1 1 d . . . . .
N2 N 0.4869(12) -0.0242(8) 0.1273(4) 0.099(3) Uani 1 1 d . . . . .
N3 N 0.2915(9) 0.2511(7) 0.1527(3) 0.0778(19) Uani 1 1 d . . . . .
N4 N 0.5283(11) 0.4621(7) 0.3396(4) 0.092(2) Uani 1 1 d . . . . .
C1 C 0.6470(8) 0.1562(6) 0.3828(3) 0.0490(13) Uani 1 1 d . . . . .
C2 C 0.8251(7) 0.1509(6) 0.3913(3) 0.0488(13) Uani 1 1 d . . . . .
C3 C 0.9195(9) 0.1338(7) 0.3276(4) 0.0626(17) Uani 1 1 d . . . . .
H3 H 0.8708 0.1275 0.2779 0.075 Uiso 1 1 calc . U . . .
C4 C 1.0871(10) 0.1261(11) 0.3385(5) 0.089(3) Uani 1 1 d . . . . .
H4 H 1.1519 0.1121 0.2964 0.106 Uiso 1 1 calc . U . . .
C5 C 1.1561(10) 0.1390(12) 0.4114(7) 0.099(3) Uani 1 1 d . . . . .
H5 H 1.2689 0.1352 0.4185 0.119 Uiso 1 1 calc . U . . .
C6 C 1.0647(11) 0.1572(10) 0.4736(5) 0.086(3) Uani 1 1 d . . . . .
H6 H 1.1148 0.1663 0.5229 0.104 Uiso 1 1 calc . U . . .
C7 C 0.8982(10) 0.1625(7) 0.4646(4) 0.0647(17) Uani 1 1 d . . . . .
H7 H 0.8351 0.1737 0.5076 0.078 Uiso 1 1 calc . U . . .
C8 C 0.5632(7) 0.1416(6) 0.3028(3) 0.0488(14) Uani 1 1 d . . . . .
C9 C 0.5616(8) 0.0200(6) 0.2710(3) 0.0536(15) Uani 1 1 d . . . . .
C10 C 0.5167(10) -0.0041(7) 0.1917(4) 0.0656(19) Uani 1 1 d . . . . .
C11 C 0.6177(9) -0.0846(7) 0.3143(3) 0.0597(16) Uani 1 1 d . . . . .
C12 C 0.4922(8) 0.2492(6) 0.2714(3) 0.0529(14) Uani 1 1 d . . . . .
C13 C 0.3848(9) 0.2502(6) 0.2039(3) 0.0579(16) Uani 1 1 d . . . . .
C14 C 0.5119(10) 0.3666(7) 0.3091(4) 0.0637(17) Uani 1 1 d . . . . .
H2 H 0.180(13) 0.479(9) 0.463(6) 0.096 Uiso 1 1 d . U . . .
H21 H 0.170(7) 0.520(9) 0.527(5) 0.096 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O1 2.708(5) . ?
K1 O2 2.765(6) . ?
K1 O2 2.805(7) 3_666 ?
K1 N4 2.808(7) 3_666 ?
K1 N1 2.828(7) 3_656 ?
K1 N3 2.891(7) 4_666 ?
K1 K1 3.984(3) 3_666 ?
O1 C1 1.223(7) . ?
O2 K1 2.805(6) 3_666 ?
N1 C11 1.158(9) . ?
N1 K1 2.828(7) 3_656 ?
N2 C10 1.144(9) . ?
N3 C13 1.142(8) . ?
N3 K1 2.891(7) 4_565 ?
N4 C14 1.146(10) . ?
N4 K1 2.807(7) 3_666 ?
C1 C2 1.466(8) . ?
C1 C8 1.520(7) . ?
C2 C7 1.378(8) . ?
C2 C3 1.383(8) . ?
C3 C4 1.384(10) . ?
C4 C5 1.361(14) . ?
C5 C6 1.349(15) . ?
C6 C7 1.371(11) . ?
C8 C12 1.379(9) . ?
C8 C9 1.400(9) . ?
C9 C11 1.401(10) . ?
C9 C10 1.421(8) . ?
C12 C14 1.408(9) . ?
C12 C13 1.427(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
O1 K1 O2 103.12(17) . . ?
O1 K1 O2 91.78(18) . 3_666 ?
O2 K1 O2 88.68(19) . 3_666 ?
O1 K1 N4 169.6(2) . 3_666 ?
O2 K1 N4 70.2(2) . 3_666 ?
O2 K1 N4 80.2(2) 3_666 3_666 ?
O1 K1 N1 97.0(2) . 3_656 ?
O2 K1 N1 99.0(2) . 3_656 ?
O2 K1 N1 166.67(19) 3_666 3_656 ?
N4 K1 N1 92.0(2) 3_666 3_656 ?
O1 K1 N3 95.75(18) . 4_666 ?
O2 K1 N3 160.3(2) . 4_666 ?
O2 K1 N3 85.1(2) 3_666 4_666 ?
N4 K1 N3 90.3(2) 3_666 4_666 ?
N1 K1 N3 84.1(2) 3_656 4_666 ?
O1 K1 K1 100.34(13) . 3_666 ?
O2 K1 K1 44.74(14) . 3_666 ?
O2 K1 K1 43.94(13) 3_666 3_666 ?
N4 K1 K1 69.25(16) 3_666 3_666 ?
N1 K1 K1 142.50(18) 3_656 3_666 ?
N3 K1 K1 126.38(16) 4_666 3_666 ?
C1 O1 K1 142.7(5) . . ?
K1 O2 K1 91.32(19) . 3_666 ?
C11 N1 K1 128.8(6) . 3_656 ?
C13 N3 K1 156.6(6) . 4_565 ?
C14 N4 K1 160.9(8) . 3_666 ?
O1 C1 C2 122.6(5) . . ?
O1 C1 C8 117.6(5) . . ?
C2 C1 C8 119.8(4) . . ?
C7 C2 C3 120.1(6) . . ?
C7 C2 C1 118.7(5) . . ?
C3 C2 C1 121.2(5) . . ?
C2 C3 C4 119.3(6) . . ?
C5 C4 C3 119.4(7) . . ?
C6 C5 C4 121.5(8) . . ?
C5 C6 C7 120.3(7) . . ?
C6 C7 C2 119.4(7) . . ?
C12 C8 C9 127.7(5) . . ?
C12 C8 C1 116.0(5) . . ?
C9 C8 C1 116.3(5) . . ?
C8 C9 C11 121.5(5) . . ?
C8 C9 C10 122.5(6) . . ?
C11 C9 C10 115.7(6) . . ?
N2 C10 C9 177.3(9) . . ?
N1 C11 C9 178.9(7) . . ?
C8 C12 C14 120.7(5) . . ?
C8 C12 C13 124.1(5) . . ?
C14 C12 C13 115.0(6) . . ?
N3 C13 C12 176.0(7) . . ?
N4 C14 C12 179.8(10) . . ?

_refine_diff_density_max         0.957
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.132

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# 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_yak397
_database_code_depnum_ccdc_archive 'CCDC 1575015'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 N4 Na O2'
_chemical_formula_sum            'C15 H9 N4 Na O2'
_chemical_formula_weight         300.25

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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.5036(19)
_cell_length_b                   27.0995(12)
_cell_length_c                   6.0260(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.992(2)
_cell_angle_gamma                90
_cell_volume                     1491.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    689
_cell_measurement_theta_min      3.5
_cell_measurement_theta_max      65

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            8935
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         4.841
_diffrn_reflns_theta_max         72.439
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2644
_reflns_number_gt                1949
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2644
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.32014(6) 0.70922(2) 0.31682(10) 0.04684(18) Uani 1 1 d . . . . .
O1 O 0.54729(12) 0.66012(4) 0.51110(18) 0.0541(3) Uani 1 1 d . . . . .
O2 O 0.21515(14) 0.71459(5) 0.6327(2) 0.0542(3) Uani 1 1 d . . . . .
N1 N 0.47081(14) 0.72103(5) 0.0477(2) 0.0477(3) Uani 1 1 d . . . . .
N2 N 0.93007(18) 0.71668(7) 1.3736(3) 0.0830(6) Uani 1 1 d . . . . .
N3 N 0.11776(16) 0.65861(5) 0.0534(3) 0.0585(4) Uani 1 1 d . . . . .
N4 N 0.84106(19) 0.57472(7) 0.4908(3) 0.0844(6) Uani 1 1 d . . . . .
C1 C 0.73081(15) 0.65460(5) 0.8645(2) 0.0350(3) Uani 1 1 d . . . . .
C2 C 0.58469(15) 0.64001(5) 0.6983(2) 0.0376(3) Uani 1 1 d . . . . .
C3 C 0.72027(15) 0.68745(5) 1.0369(2) 0.0384(3) Uani 1 1 d . . . . .
C4 C 0.85652(15) 0.63487(5) 0.8248(2) 0.0400(3) Uani 1 1 d . . . . .
C5 C 0.84734(17) 0.60138(6) 0.6393(3) 0.0506(4) Uani 1 1 d . . . . .
C6 C 1.00066(17) 0.64812(5) 0.9546(3) 0.0431(3) Uani 1 1 d . . . . .
C7 C 0.83883(17) 0.70360(6) 1.2204(3) 0.0496(4) Uani 1 1 d . . . . .
C8 C 0.58266(16) 0.70595(5) 1.0432(2) 0.0378(3) Uani 1 1 d . . . . .
C9 C 0.49137(15) 0.60450(5) 0.7771(2) 0.0393(3) Uani 1 1 d . . . . .
C10 C 0.35546(17) 0.59197(6) 0.6286(3) 0.0518(4) Uani 1 1 d . . . . .
H10 H 0.3279 0.6041 0.4786 0.062 Uiso 1 1 calc R U . . .
C11 C 0.2623(2) 0.56164(6) 0.7041(4) 0.0632(5) Uani 1 1 d . . . . .
H11 H 0.1722 0.5535 0.6035 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2995(2) 0.54310(6) 0.9252(4) 0.0626(5) Uani 1 1 d . . . . .
C13 C 0.4364(2) 0.55447(6) 1.0710(3) 0.0592(5) Uani 1 1 d . . . . .
H13 H 0.4643 0.5414 1.2195 0.071 Uiso 1 1 calc R U . . .
C14 C 0.53156(17) 0.58485(6) 0.9983(3) 0.0476(4) Uani 1 1 d . . . . .
H14 H 0.6228 0.5922 1.0979 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1943(3) 0.51134(8) 1.0094(5) 0.0947(8) Uani 1 1 d . . . . .
H15A H 0.1201 0.5318 1.0424 0.142 Uiso 1 1 calc R U . . .
H15B H 0.2464 0.4942 1.1470 0.142 Uiso 1 1 calc R U . . .
H15C H 0.1494 0.4878 0.8922 0.142 Uiso 1 1 calc R U . . .
H21 H 0.230(3) 0.6956(10) 0.744(5) 0.104(9) Uiso 1 1 d . . . . .
H22 H 0.121(3) 0.7163(9) 0.559(4) 0.097(8) Uiso 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
Na1 O2 2.3849(13) . ?
Na1 O2 2.4249(13) 4_575 ?
Na1 N1 2.4623(14) . ?
Na1 O1 2.5314(12) . ?
Na1 N3 2.5334(15) . ?
Na1 N1 2.5419(13) 4_576 ?
Na1 Na1 3.7367(7) 4_576 ?
Na1 Na1 3.7368(7) 4_575 ?
O1 C2 1.2146(17) . ?
O2 Na1 2.4248(13) 4_576 ?
N1 C8 1.1460(18) 1_554 ?
N1 Na1 2.5418(13) 4_575 ?
N2 C7 1.135(2) . ?
N3 C6 1.1440(19) 1_454 ?
N4 C5 1.139(2) . ?
C1 C4 1.389(2) . ?
C1 C3 1.3926(19) . ?
C1 C2 1.5235(19) . ?
C2 C9 1.473(2) . ?
C3 C8 1.411(2) . ?
C3 C7 1.413(2) . ?
C4 C5 1.424(2) . ?
C4 C6 1.424(2) . ?
C6 N3 1.1440(19) 1_656 ?
C8 N1 1.1460(18) 1_556 ?
C9 C14 1.388(2) . ?
C9 C10 1.396(2) . ?
C10 C11 1.374(2) . ?
C11 C12 1.376(3) . ?
C12 C13 1.389(3) . ?
C12 C15 1.509(2) . ?
C13 C14 1.380(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Na1 O2 95.93(5) . 4_575 ?
O2 Na1 N1 164.80(5) . . ?
O2 Na1 N1 80.14(5) 4_575 . ?
O2 Na1 O1 98.85(5) . . ?
O2 Na1 O1 148.22(5) 4_575 . ?
N1 Na1 O1 78.25(4) . . ?
O2 Na1 N3 96.94(5) . . ?
O2 Na1 N3 91.64(5) 4_575 . ?
N1 Na1 N3 97.84(5) . . ?
O1 Na1 N3 114.13(5) . . ?
O2 Na1 N1 79.30(4) . 4_576 ?
O2 Na1 N1 73.49(5) 4_575 4_576 ?
N1 Na1 N1 85.51(4) . 4_576 ?
O1 Na1 N1 81.82(4) . 4_576 ?
N3 Na1 N1 164.05(5) . 4_576 ?
O2 Na1 Na1 39.41(3) . 4_576 ?
O2 Na1 Na1 76.92(4) 4_575 4_576 ?
N1 Na1 Na1 125.69(4) . 4_576 ?
O1 Na1 Na1 97.32(3) . 4_576 ?
N3 Na1 Na1 131.06(4) . 4_576 ?
N1 Na1 Na1 40.89(3) 4_576 4_576 ?
O2 Na1 Na1 134.47(4) . 4_575 ?
O2 Na1 Na1 38.64(3) 4_575 4_575 ?
N1 Na1 Na1 42.51(3) . 4_575 ?
O1 Na1 Na1 119.63(3) . 4_575 ?
N3 Na1 Na1 89.06(4) . 4_575 ?
N1 Na1 Na1 82.89(3) 4_576 4_575 ?
Na1 Na1 Na1 107.47(3) 4_576 4_575 ?
C2 O1 Na1 131.26(10) . . ?
Na1 O2 Na1 101.96(5) . 4_576 ?
C8 N1 Na1 132.88(11) 1_554 . ?
C8 N1 Na1 129.69(11) 1_554 4_575 ?
Na1 N1 Na1 96.60(5) . 4_575 ?
C6 N3 Na1 157.29(12) 1_454 . ?
C4 C1 C3 128.09(13) . . ?
C4 C1 C2 117.28(12) . . ?
C3 C1 C2 114.61(12) . . ?
O1 C2 C9 122.98(13) . . ?
O1 C2 C1 118.33(12) . . ?
C9 C2 C1 118.58(12) . . ?
C1 C3 C8 120.32(12) . . ?
C1 C3 C7 125.17(13) . . ?
C8 C3 C7 114.47(12) . . ?
C1 C4 C5 120.75(13) . . ?
C1 C4 C6 123.47(13) . . ?
C5 C4 C6 115.70(13) . . ?
N4 C5 C4 179.4(2) . . ?
N3 C6 C4 178.08(17) 1_656 . ?
N2 C7 C3 177.05(19) . . ?
N1 C8 C3 179.80(17) 1_556 . ?
C14 C9 C10 118.92(13) . . ?
C14 C9 C2 121.97(13) . . ?
C10 C9 C2 119.04(14) . . ?
C11 C10 C9 120.02(16) . . ?
C10 C11 C12 121.48(17) . . ?
C11 C12 C13 118.51(15) . . ?
C11 C12 C15 121.10(19) . . ?
C13 C12 C15 120.4(2) . . ?
C14 C13 C12 120.86(17) . . ?
C13 C14 C9 120.18(15) . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_yak438
_database_code_depnum_ccdc_archive 'CCDC 1575056'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 Li N4 O2'
_chemical_formula_sum            'C15 H9 Li N4 O2'
_chemical_formula_weight         284.20

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'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.1025(5)
_cell_length_b                   14.6322(6)
_cell_length_c                   10.1353(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.709(4)
_cell_angle_gamma                90
_cell_volume                     1427.22(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    687
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .15
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10382
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.595
_diffrn_reflns_theta_max         72.781
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2792
_reflns_number_gt                1640
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2792
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   0.811
_refine_ls_restrained_S_all      0.811
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25976(10) 0.29030(8) 0.67839(11) 0.0461(3) Uani 1 1 d . . . . .
O2 O 0.11618(15) 0.09884(12) 0.55646(16) 0.0665(4) Uani 1 1 d . . . . .
N1 N 0.36759(15) 0.37637(11) 0.36843(14) 0.0557(4) Uani 1 1 d . . . . .
N2 N 0.77911(17) 0.35767(15) 0.63729(17) 0.0813(6) Uani 1 1 d . . . . .
N3 N 0.80955(15) 0.39318(13) 0.97100(15) 0.0679(5) Uani 1 1 d . . . . .
N4 N 0.41537(14) 0.36533(11) 1.05468(14) 0.0546(4) Uani 1 1 d . . . . .
C1 C 0.31465(14) 0.36591(12) 0.70016(13) 0.0351(4) Uani 1 1 d . . . . .
C2 C 0.47161(14) 0.37033(10) 0.73322(14) 0.0342(3) Uani 1 1 d . . . . .
C3 C 0.52323(14) 0.37061(11) 0.62125(14) 0.0387(4) Uani 1 1 d . . . . .
C4 C 0.54633(14) 0.37248(12) 0.87444(14) 0.0385(4) Uani 1 1 d . . . . .
C5 C 0.47510(15) 0.36887(12) 0.97483(15) 0.0414(4) Uani 1 1 d . . . . .
C6 C 0.69225(16) 0.38291(13) 0.92664(15) 0.0454(4) Uani 1 1 d . . . . .
C7 C 0.66619(17) 0.36431(13) 0.63254(16) 0.0488(4) Uani 1 1 d . . . . .
C8 C 0.43386(15) 0.37389(12) 0.48233(15) 0.0420(4) Uani 1 1 d . . . . .
C9 C 0.23788(14) 0.45039(11) 0.69653(14) 0.0356(4) Uani 1 1 d . . . . .
C10 C 0.09714(16) 0.44660(12) 0.68398(16) 0.0439(4) Uani 1 1 d . . . . .
H10 H 0.0536 0.3904 0.6819 0.053 Uiso 1 1 calc R U . . .
C11 C 0.02255(17) 0.52607(13) 0.67464(17) 0.0493(4) Uani 1 1 d . . . . .
H11 H -0.0713 0.5229 0.6675 0.059 Uiso 1 1 calc R U . . .
C12 C 0.08381(17) 0.61067(12) 0.67563(16) 0.0464(4) Uani 1 1 d . . . . .
C13 C 0.22433(18) 0.61417(12) 0.69048(17) 0.0481(4) Uani 1 1 d . . . . .
H13 H 0.2676 0.6705 0.6932 0.058 Uiso 1 1 calc R U . . .
C14 C 0.30083(16) 0.53524(12) 0.70130(16) 0.0433(4) Uani 1 1 d . . . . .
H14 H 0.3954 0.5387 0.7119 0.052 Uiso 1 1 calc R U . . .
C15 C 0.0006(2) 0.69690(14) 0.6606(2) 0.0715(6) Uani 1 1 d . . . . .
H15A H 0.0138 0.7236 0.7502 0.107 Uiso 1 1 calc R U . . .
H15B H -0.0961 0.6832 0.6187 0.107 Uiso 1 1 calc R U . . .
H15C H 0.0306 0.7392 0.6031 0.107 Uiso 1 1 calc R U . . .
Li1 Li 0.2790(3) 0.1593(2) 0.6633(3) 0.0450(7) Uani 1 1 d . . . . .
H21 H 0.029(3) 0.1089(18) 0.542(3) 0.107(9) Uiso 1 1 d . . . . .
H22 H 0.130(3) 0.046(2) 0.530(3) 0.128(12) Uiso 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 C1 1.2270(18) . ?
O1 Li1 1.938(3) . ?
O2 Li1 1.891(3) . ?
O2 H21 0.86(3) . ?
O2 H22 0.84(3) . ?
N1 C8 1.1455(19) . ?
N1 Li1 2.065(3) 4_565 ?
N2 C7 1.131(2) . ?
N3 C6 1.142(2) . ?
N4 C5 1.148(2) . ?
N4 Li1 2.040(3) 4_566 ?
C1 C9 1.454(2) . ?
C1 C2 1.519(2) . ?
C2 C3 1.386(2) . ?
C2 C4 1.4007(18) . ?
C3 C7 1.417(2) . ?
C3 C8 1.424(2) . ?
C4 C5 1.415(2) . ?
C4 C6 1.415(2) . ?
C9 C14 1.389(2) . ?
C9 C10 1.389(2) . ?
C10 C11 1.373(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(2) . ?
C12 C15 1.498(3) . ?
C13 C14 1.375(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
Li1 N4 2.040(3) 4_565 ?
Li1 N1 2.065(3) 4_566 ?

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 O1 Li1 148.82(13) . . ?
Li1 O2 H21 133.3(18) . . ?
Li1 O2 H22 114(2) . . ?
H21 O2 H22 111(3) . . ?
C8 N1 Li1 161.49(17) . 4_565 ?
C5 N4 Li1 166.91(15) . 4_566 ?
O1 C1 C9 123.62(13) . . ?
O1 C1 C2 117.54(14) . . ?
C9 C1 C2 118.84(14) . . ?
C3 C2 C4 128.08(13) . . ?
C3 C2 C1 116.56(12) . . ?
C4 C2 C1 115.36(12) . . ?
C2 C3 C7 124.20(13) . . ?
C2 C3 C8 121.78(12) . . ?
C7 C3 C8 113.98(13) . . ?
C2 C4 C5 120.01(12) . . ?
C2 C4 C6 124.12(13) . . ?
C5 C4 C6 115.79(13) . . ?
N4 C5 C4 178.85(16) . . ?
N3 C6 C4 178.2(2) . . ?
N2 C7 C3 177.6(2) . . ?
N1 C8 C3 176.66(16) . . ?
C14 C9 C10 118.94(15) . . ?
C14 C9 C1 121.60(14) . . ?
C10 C9 C1 119.44(15) . . ?
C11 C10 C9 119.82(16) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.51(15) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 118.46(16) . . ?
C13 C12 C15 120.39(17) . . ?
C11 C12 C15 121.15(17) . . ?
C14 C13 C12 120.74(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 120.50(15) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 Li1 O1 114.66(15) . . ?
O2 Li1 N4 102.78(14) . 4_565 ?
O1 Li1 N4 108.52(14) . 4_565 ?
O2 Li1 N1 119.57(16) . 4_566 ?
O1 Li1 N1 101.15(13) . 4_566 ?
N4 Li1 N1 109.98(13) 4_565 4_566 ?

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
O2 H21 N3 0.86(3) 2.12(3) 2.954(2) 166(2) 4_465
O2 H22 N3 0.84(3) 2.32(4) 3.134(3) 163(3) 2_646

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_YAK393
_database_code_depnum_ccdc_archive 'CCDC 1575014'
_audit_update_record             
;
2017-10-20 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H16 N8 Na2 O3'
_chemical_formula_sum            'C30 H16 N8 Na2 O3'
_chemical_formula_weight         582.49

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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -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                   29.668(3)
_cell_length_b                   9.5151(7)
_cell_length_c                   10.3581(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.061(7)
_cell_angle_gamma                90
_cell_volume                     2848.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    286
_cell_measurement_theta_min      3
_cell_measurement_theta_max      48

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.210
_exptl_absorpt_correction_T_max  0.309
_exptl_absorpt_special_details   ?
_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10169
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.893
_diffrn_reflns_theta_max         72.690
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2749
_reflns_number_gt                1187
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1018P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2749
_refine_ls_number_parameters     207
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1992
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.46554(7) 0.14921(14) 0.56299(13) 0.1065(6) Uani 1 1 d . . . . .
O1 O 0.41159(10) 0.1469(3) 0.3616(2) 0.0957(8) Uani 1 1 d . . . . .
N1 N 0.3293(2) 0.4145(6) 0.4364(5) 0.162(2) Uani 1 1 d . . . . .
C3 C 0.38709(16) 0.4613(4) 0.2924(4) 0.0948(13) Uani 1 1 d . . . . .
C6 C 0.3996(2) 0.6043(6) 0.2863(4) 0.1248(19) Uani 1 1 d . . . . .
N2 N 0.4095(2) 0.7186(5) 0.2848(5) 0.196(3) Uani 1 1 d . . . . .
N3 N 0.46738(13) 0.5958(4) 0.0807(3) 0.1041(11) Uani 1 1 d . . . . .
N4 N 0.46963(11) 0.1337(3) 0.0760(3) 0.0815(9) Uani 1 1 d . . . . .
C1 C 0.40698(13) 0.3536(3) 0.2354(3) 0.0715(9) Uani 1 1 d . . . . .
C2 C 0.39175(12) 0.2065(3) 0.2599(3) 0.0708(9) Uani 1 1 d . . . . .
C4 C 0.43899(12) 0.3621(3) 0.1554(3) 0.0674(9) Uani 1 1 d . . . . .
C5 C 0.3551(2) 0.4332(6) 0.3721(5) 0.1183(18) Uani 1 1 d . . . . .
C7 C 0.45549(13) 0.4913(4) 0.1150(3) 0.0789(10) Uani 1 1 d . . . . .
C8 C 0.45620(12) 0.2377(3) 0.1101(3) 0.0656(8) Uani 1 1 d . . . . .
C9 C 0.35542(12) 0.1402(4) 0.1594(3) 0.0689(9) Uani 1 1 d . . . . .
C10 C 0.33090(13) 0.2144(4) 0.0522(3) 0.0836(10) Uani 1 1 d . . . . .
H10 H 0.3363 0.3100 0.0446 0.100 Uiso 1 1 calc R U . . .
C11 C 0.29816(14) 0.1466(5) -0.0445(4) 0.0940(12) Uani 1 1 d . . . . .
H11 H 0.2816 0.1979 -0.1160 0.113 Uiso 1 1 calc R U . . .
C12 C 0.28969(14) 0.0052(5) -0.0367(4) 0.0921(12) Uani 1 1 d . . . . .
C13 C 0.31397(15) -0.0670(5) 0.0715(4) 0.0968(12) Uani 1 1 d . . . . .
H13 H 0.3085 -0.1625 0.0790 0.116 Uiso 1 1 calc R U . . .
C14 C 0.34630(14) -0.0014(4) 0.1692(4) 0.0843(10) Uani 1 1 d . . . . .
H14 H 0.3621 -0.0525 0.2420 0.101 Uiso 1 1 calc R U . . .
C15 C 0.25434(17) -0.0679(6) -0.1440(5) 0.1269(17) Uani 1 1 d . . . . .
H15A H 0.2247 -0.0656 -0.1216 0.190 Uiso 1 1 calc R U . . .
H15B H 0.2635 -0.1637 -0.1515 0.190 Uiso 1 1 calc R U . . .
H15C H 0.2524 -0.0206 -0.2270 0.190 Uiso 1 1 calc R U . . .
O2 O 0.47087(17) 0.1079(4) 0.7730(4) 0.0734(12) Uani 0.5 1 d D . P . .
H2 H 0.4626(9) 0.171(4) 0.819(4) 0.110 Uiso 0.5 1 d D U P . .
H21 H 0.4608(16) 0.028(3) 0.798(7) 0.110 Uiso 0.5 1 d D U P . .


_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
Na1 O2 2.181(4) . ?
Na1 O2 2.270(5) 2_656 ?
Na1 O1 2.325(3) . ?
Na1 N3 2.433(4) 6_566 ?
Na1 N4 2.654(4) 2_655 ?
Na1 N4 2.696(3) 6_556 ?
Na1 N2 3.369(8) 6_566 ?
Na1 Na1 3.893(3) 5_656 ?
Na1 Na1 3.951(3) 2_656 ?
O1 C2 1.223(4) . ?
N1 C5 1.136(7) . ?
C3 C1 1.380(5) . ?
C3 C5 1.417(8) . ?
C3 C6 1.415(7) . ?
C6 N2 1.127(7) . ?
N2 Na1 3.369(8) 6_565 ?
N3 C7 1.139(5) . ?
N3 Na1 2.433(4) 6_565 ?
N4 C8 1.152(4) . ?
N4 Na1 2.655(4) 2_655 ?
N4 Na1 2.696(3) 6 ?
C1 C4 1.397(5) . ?
C1 C2 1.510(5) . ?
C2 C9 1.462(5) . ?
C4 C8 1.410(5) . ?
C4 C7 1.421(5) . ?
C9 C10 1.377(5) . ?
C9 C14 1.382(5) . ?
C10 C11 1.386(5) . ?
C11 C12 1.375(6) . ?
C12 C13 1.372(6) . ?
C12 C15 1.514(6) . ?
C13 C14 1.377(6) . ?
O2 Na1 2.270(5) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Na1 O2 50.3(2) . 2_656 ?
O2 Na1 O1 140.66(18) . . ?
O2 Na1 O1 163.18(14) 2_656 . ?
O2 Na1 N3 96.28(14) . 6_566 ?
O2 Na1 N3 96.64(14) 2_656 6_566 ?
O1 Na1 N3 94.37(11) . 6_566 ?
O2 Na1 N4 129.27(17) . 2_655 ?
O2 Na1 N4 79.32(14) 2_656 2_655 ?
O1 Na1 N4 87.08(11) . 2_655 ?
N3 Na1 N4 95.14(13) 6_566 2_655 ?
O2 Na1 N4 77.17(13) . 6_556 ?
O2 Na1 N4 76.66(12) 2_656 6_556 ?
O1 Na1 N4 92.83(10) . 6_556 ?
N3 Na1 N4 172.65(12) 6_566 6_556 ?
N4 Na1 N4 86.65(11) 2_655 6_556 ?
O2 Na1 N2 47.37(15) . 6_566 ?
O2 Na1 N2 90.52(15) 2_656 6_566 ?
O1 Na1 N2 105.65(13) . 6_566 ?
N3 Na1 N2 65.32(12) 6_566 6_566 ?
N4 Na1 N2 156.98(12) 2_655 6_566 ?
N4 Na1 N2 111.24(11) 6_556 6_566 ?
O2 Na1 Na1 106.13(13) . 5_656 ?
O2 Na1 Na1 73.37(11) 2_656 5_656 ?
O1 Na1 Na1 89.97(8) . 5_656 ?
N3 Na1 Na1 138.42(13) 6_566 5_656 ?
N4 Na1 Na1 43.74(7) 2_655 5_656 ?
N4 Na1 Na1 42.90(7) 6_556 5_656 ?
N2 Na1 Na1 151.46(10) 6_566 5_656 ?
O2 Na1 Na1 28.01(13) . 2_656 ?
O2 Na1 Na1 26.82(11) 2_656 2_656 ?
O1 Na1 Na1 168.15(12) . 2_656 ?
N3 Na1 Na1 85.89(9) 6_566 2_656 ?
N4 Na1 Na1 104.71(10) 2_655 2_656 ?
N4 Na1 Na1 86.76(7) 6_556 2_656 ?
N2 Na1 Na1 63.71(10) 6_566 2_656 ?
Na1 Na1 Na1 97.70(6) 5_656 2_656 ?
C2 O1 Na1 150.2(3) . . ?
C1 C3 C5 121.1(4) . . ?
C1 C3 C6 123.6(5) . . ?
C5 C3 C6 115.1(4) . . ?
N2 C6 C3 178.3(6) . . ?
C6 N2 Na1 122.7(5) . 6_565 ?
C7 N3 Na1 153.0(3) . 6_565 ?
C8 N4 Na1 117.5(2) . 2_655 ?
C8 N4 Na1 149.1(3) . 6 ?
Na1 N4 Na1 93.35(11) 2_655 6 ?
C3 C1 C4 128.6(4) . . ?
C3 C1 C2 116.3(4) . . ?
C4 C1 C2 115.0(3) . . ?
O1 C2 C9 123.2(3) . . ?
O1 C2 C1 118.1(3) . . ?
C9 C2 C1 118.7(3) . . ?
C1 C4 C8 119.7(3) . . ?
C1 C4 C7 123.4(3) . . ?
C8 C4 C7 116.9(3) . . ?
N1 C5 C3 178.1(6) . . ?
N3 C7 C4 177.9(4) . . ?
N4 C8 C4 177.7(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C2 121.6(3) . . ?
C14 C9 C2 119.5(3) . . ?
C9 C10 C11 120.0(4) . . ?
C12 C11 C10 121.4(4) . . ?
C13 C12 C11 118.0(4) . . ?
C13 C12 C15 121.2(4) . . ?
C11 C12 C15 120.8(4) . . ?
C12 C13 C14 121.6(4) . . ?
C13 C14 C9 120.2(4) . . ?
Na1 O2 Na1 125.2(2) . 2_656 ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_yak437
_database_code_depnum_ccdc_archive 'CCDC 1575055'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 Li N4 O3'
_chemical_formula_sum            'C15 H9 Li N4 O3'
_chemical_formula_weight         300.20

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'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.982(2)
_cell_length_b                   15.469(2)
_cell_length_c                   10.057(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.520(10)
_cell_angle_gamma                90
_cell_volume                     1496.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    865
_cell_measurement_theta_min      4
_cell_measurement_theta_max      55

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10804
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.597
_diffrn_reflns_theta_max         72.373
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2942
_reflns_number_gt                2197
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1245P)²+0.0443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2942
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1722
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26212(14) 0.28652(9) 0.70061(15) 0.0498(4) Uani 1 1 d . . . . .
O2 O -0.0393(2) 0.64529(12) 0.6471(2) 0.0831(6) Uani 1 1 d . . . . .
N1 N 0.4163(2) 0.36016(14) 1.06855(19) 0.0615(5) Uani 1 1 d . . . . .
N2 N 0.8062(2) 0.40261(17) 0.9653(2) 0.0728(6) Uani 1 1 d . . . . .
N3 N 0.7742(2) 0.3337(2) 0.6286(3) 0.0966(9) Uani 1 1 d . . . . .
N4 N 0.3688(2) 0.37588(17) 0.37948(19) 0.0665(6) Uani 1 1 d . . . . .
C1 C 0.31227(19) 0.35892(12) 0.71387(17) 0.0399(4) Uani 1 1 d . . . . .
C2 C 0.46975(18) 0.36630(13) 0.74203(18) 0.0413(4) Uani 1 1 d . . . . .
C3 C 0.52183(19) 0.36499(15) 0.6271(2) 0.0485(5) Uani 1 1 d . . . . .
C4 C 0.54480(19) 0.37054(14) 0.88009(19) 0.0453(5) Uani 1 1 d . . . . .
C5 C 0.4335(2) 0.37097(16) 0.4915(2) 0.0521(5) Uani 1 1 d . . . . .
C6 C 0.6631(2) 0.34992(19) 0.6324(2) 0.0635(7) Uani 1 1 d . . . . .
C7 C 0.6899(2) 0.38690(15) 0.9257(2) 0.0516(5) Uani 1 1 d . . . . .
C8 C 0.4747(2) 0.36487(14) 0.98544(19) 0.0475(5) Uani 1 1 d . . . . .
C9 C 0.22931(19) 0.43697(13) 0.70377(18) 0.0439(5) Uani 1 1 d . . . . .
C10 C 0.2826(2) 0.51892(14) 0.7020(2) 0.0529(5) Uani 1 1 d . . . . .
H10 H 0.3775 0.5262 0.7136 0.063 Uiso 1 1 calc R U . . .
C11 C 0.1954(3) 0.59154(14) 0.6829(2) 0.0588(6) Uani 1 1 d . . . . .
H11 H 0.2311 0.6468 0.6796 0.071 Uiso 1 1 calc R U . . .
C12 C 0.0553(2) 0.57916(16) 0.6690(2) 0.0578(6) Uani 1 1 d . . . . .
C13 C 0.0004(2) 0.49884(16) 0.6751(2) 0.0602(6) Uani 1 1 d . . . . .
H13 H -0.0937 0.4923 0.6686 0.072 Uiso 1 1 calc R U . . .
C14 C 0.0853(2) 0.42820(15) 0.6910(2) 0.0520(5) Uani 1 1 d . . . . .
H14 H 0.0479 0.3734 0.6935 0.062 Uiso 1 1 calc R U . . .
C15 C -0.0021(4) 0.72728(18) 0.6148(3) 0.0854(8) Uani 1 1 d . . . . .
H15A H 0.0595 0.7529 0.6950 0.128 Uiso 1 1 calc R U . . .
H15B H -0.0840 0.7623 0.5844 0.128 Uiso 1 1 calc R U . . .
H15C H 0.0439 0.7234 0.5425 0.128 Uiso 1 1 calc R U . . .
O3 O 0.12053(19) 0.09639(13) 0.57048(19) 0.0620(5) Uani 1 1 d . . . . .
Li1 Li 0.2735(4) 0.1606(2) 0.6830(3) 0.0491(8) Uani 1 1 d . . . . .
H31 H 0.040(5) 0.106(3) 0.554(4) 0.113(13) Uiso 1 1 d . . . . .
H32 H 0.141(4) 0.041(3) 0.553(4) 0.118(13) Uiso 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 C1 1.219(2) . ?
O1 Li1 1.962(4) . ?
O2 C12 1.369(3) . ?
O2 C15 1.384(4) . ?
N1 C8 1.142(3) . ?
N1 Li1 2.083(4) 4_566 ?
N2 C7 1.148(3) . ?
N3 C6 1.147(3) . ?
N4 C5 1.141(3) . ?
N4 Li1 2.031(4) 4_565 ?
C1 C9 1.452(3) . ?
C1 C2 1.525(2) . ?
C2 C3 1.388(3) . ?
C2 C4 1.392(3) . ?
C3 C5 1.415(3) . ?
C3 C6 1.416(3) . ?
C4 C8 1.420(3) . ?
C4 C7 1.420(3) . ?
C9 C10 1.377(3) . ?
C9 C14 1.415(3) . ?
C10 C11 1.402(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(3) . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O3 Li1 1.916(4) . ?
O3 H31 0.79(4) . ?
O3 H32 0.91(5) . ?
Li1 N4 2.031(4) 4_566 ?
Li1 N1 2.083(4) 4_565 ?

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 O1 Li1 152.85(16) . . ?
C12 O2 C15 120.4(2) . . ?
C8 N1 Li1 166.7(2) . 4_566 ?
C5 N4 Li1 159.4(2) . 4_565 ?
O1 C1 C9 123.11(17) . . ?
O1 C1 C2 117.49(17) . . ?
C9 C1 C2 119.40(16) . . ?
C3 C2 C4 127.57(17) . . ?
C3 C2 C1 116.18(16) . . ?
C4 C2 C1 116.21(15) . . ?
C2 C3 C5 121.73(17) . . ?
C2 C3 C6 124.20(18) . . ?
C5 C3 C6 113.83(17) . . ?
C2 C4 C8 120.02(16) . . ?
C2 C4 C7 124.12(16) . . ?
C8 C4 C7 115.69(16) . . ?
N4 C5 C3 176.2(2) . . ?
N3 C6 C3 175.0(3) . . ?
N2 C7 C4 177.5(3) . . ?
N1 C8 C4 178.9(2) . . ?
C10 C9 C14 118.26(19) . . ?
C10 C9 C1 123.48(18) . . ?
C14 C9 C1 118.23(18) . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 118.5(2) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C13 C12 O2 114.8(2) . . ?
C13 C12 C11 121.9(2) . . ?
O2 C12 C11 123.3(2) . . ?
C14 C13 C12 119.3(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 121.2(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Li1 O3 H31 130(3) . . ?
Li1 O3 H32 115(2) . . ?
H31 O3 H32 114(4) . . ?
O3 Li1 O1 120.79(19) . . ?
O3 Li1 N4 121.5(2) . 4_566 ?
O1 Li1 N4 102.20(17) . 4_566 ?
O3 Li1 N1 98.56(16) . 4_565 ?
O1 Li1 N1 105.52(18) . 4_565 ?
N4 Li1 N1 106.45(17) 4_566 4_565 ?

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
C15 H15A N3 0.96 2.43 3.377(4) 170.6 2_656
C15 H15B O3 0.96 2.65 3.336(4) 128.6 3_566
O3 H31 N2 0.79(4) 2.27(4) 3.031(3) 163(4) 4_465
O3 H32 N2 0.91(5) 2.22(5) 3.129(3) 174(3) 2_646

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_yak439
_database_code_depnum_ccdc_archive 'CCDC 1575057'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 Br Li N4 O2'
_chemical_formula_sum            'C14 H6 Br Li N4 O2'
_chemical_formula_weight         349.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Li Li 0.0008 0.0003 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.1420(3)
_cell_length_b                   14.7088(4)
_cell_length_c                   10.0556(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.5590(10)
_cell_angle_gamma                90
_cell_volume                     1437.85(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    743
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .20
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .14
_exptl_absorpt_coefficient_mu    3.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10580
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.548
_diffrn_reflns_theta_max         72.847
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2752
_reflns_number_gt                2049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.0056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2752
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0921
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.02582(3) 0.21000(2) 0.86134(4) 0.06929(17) Uani 1 1 d . . . . .
O1 O -0.26837(16) -0.20994(11) 0.8018(2) 0.0438(4) Uani 1 1 d . . . . .
O2 O -0.1192(2) -0.40090(19) 0.9315(3) 0.0627(6) Uani 1 1 d . . . . .
N1 N -0.3754(2) -0.12005(18) 1.1199(3) 0.0546(6) Uani 1 1 d . . . . .
N2 N -0.7837(3) -0.1380(3) 0.8568(3) 0.0816(9) Uani 1 1 d . . . . .
N3 N -0.8087(2) -0.0976(2) 0.5212(3) 0.0619(7) Uani 1 1 d . . . . .
N4 N -0.4165(2) -0.13666(18) 0.4336(2) 0.0537(6) Uani 1 1 d . . . . .
C1 C -0.3207(2) -0.13462(16) 0.7871(2) 0.0344(5) Uani 1 1 d . . . . .
C2 C -0.4769(2) -0.12844(15) 0.7556(2) 0.0340(5) Uani 1 1 d . . . . .
C3 C -0.5287(2) -0.12698(17) 0.8688(3) 0.0386(5) Uani 1 1 d . . . . .
C4 C -0.5489(2) -0.12588(17) 0.6152(2) 0.0371(5) Uani 1 1 d . . . . .
C5 C -0.4766(2) -0.13193(18) 0.5141(3) 0.0418(6) Uani 1 1 d . . . . .
C6 C -0.6937(2) -0.11158(18) 0.5640(3) 0.0433(6) Uani 1 1 d . . . . .
C7 C -0.6711(3) -0.1320(2) 0.8588(3) 0.0494(6) Uani 1 1 d . . . . .
C8 C -0.4408(2) -0.12336(18) 1.0064(3) 0.0419(6) Uani 1 1 d . . . . .
C9 C -0.2408(2) -0.05093(16) 0.7988(3) 0.0358(5) Uani 1 1 d . . . . .
C10 C -0.0998(2) -0.05633(17) 0.8133(3) 0.0415(6) Uani 1 1 d . . . . .
H10 H -0.058606 -0.112720 0.812279 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0220(3) 0.02137(18) 0.8291(3) 0.0465(6) Uani 1 1 d . . . . .
H11 H 0.071723 0.018120 0.837871 0.056 Uiso 1 1 calc R U . . .
C12 C -0.0844(3) 0.10420(18) 0.8317(3) 0.0451(6) Uani 1 1 d . . . . .
C13 C -0.2232(3) 0.11173(18) 0.8157(3) 0.0473(6) Uani 1 1 d . . . . .
H13 H -0.263395 0.168500 0.816352 0.057 Uiso 1 1 calc R U . . .
C14 C -0.3017(2) 0.03415(17) 0.7988(3) 0.0425(6) Uani 1 1 d . . . . .
H14 H -0.395750 0.038355 0.787221 0.051 Uiso 1 1 calc R U . . .
Li1 Li -0.2787(4) -0.3412(3) 0.8205(5) 0.0435(9) Uani 1 1 d . . . . .
H21 H -0.124(4) -0.452(4) 0.953(5) 0.096(16) Uiso 1 1 d . . . . .
H22 H -0.051(5) -0.387(3) 0.938(5) 0.080(14) Uiso 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
Br1 C12 1.889(3) . ?
O1 C1 1.219(3) . ?
O1 Li1 1.945(5) . ?
O2 Li1 1.898(5) . ?
O2 H21 0.78(5) . ?
O2 H22 0.71(4) . ?
N1 C8 1.146(3) . ?
N1 Li1 2.057(5) 4_556 ?
N2 C7 1.140(4) . ?
N3 C6 1.141(3) . ?
N4 C5 1.146(3) . ?
N4 Li1 2.063(5) 4 ?
C1 C9 1.460(3) . ?
C1 C2 1.527(3) . ?
C2 C3 1.383(3) . ?
C2 C4 1.393(3) . ?
C3 C8 1.418(4) . ?
C3 C7 1.420(3) . ?
C4 C5 1.416(4) . ?
C4 C6 1.427(3) . ?
C9 C14 1.395(3) . ?
C9 C10 1.398(3) . ?
C10 C11 1.372(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(4) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 Li1 151.66(19) . . ?
Li1 O2 H21 119(3) . . ?
Li1 O2 H22 124(3) . . ?
H21 O2 H22 113(4) . . ?
C8 N1 Li1 160.7(3) . 4_556 ?
C5 N4 Li1 168.3(2) . 4 ?
O1 C1 C9 123.0(2) . . ?
O1 C1 C2 118.0(2) . . ?
C9 C1 C2 119.04(19) . . ?
C3 C2 C4 128.4(2) . . ?
C3 C2 C1 116.5(2) . . ?
C4 C2 C1 115.14(19) . . ?
C2 C3 C8 121.5(2) . . ?
C2 C3 C7 123.9(2) . . ?
C8 C3 C7 114.5(2) . . ?
C2 C4 C5 119.8(2) . . ?
C2 C4 C6 123.9(2) . . ?
C5 C4 C6 116.2(2) . . ?
N4 C5 C4 179.1(3) . . ?
N3 C6 C4 177.8(3) . . ?
N2 C7 C3 176.7(4) . . ?
N1 C8 C3 176.6(3) . . ?
C14 C9 C10 119.3(2) . . ?
C14 C9 C1 121.4(2) . . ?
C10 C9 C1 119.2(2) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 122.0(2) . . ?
C13 C12 Br1 119.5(2) . . ?
C11 C12 Br1 118.53(19) . . ?
C14 C13 C12 119.0(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
O2 Li1 O1 117.1(2) . . ?
O2 Li1 N1 122.5(2) . 4 ?
O1 Li1 N1 101.8(2) . 4 ?
O2 Li1 N4 101.5(2) . 4_556 ?
O1 Li1 N4 105.9(2) . 4_556 ?
N1 Li1 N4 106.8(2) 4 4_556 ?

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
Li1 O1 C1 C9 171.5(4) . . . . ?
Li1 O1 C1 C2 -8.2(6) . . . . ?
O1 C1 C2 C3 87.0(3) . . . . ?
C9 C1 C2 C3 -92.7(3) . . . . ?
O1 C1 C2 C4 -92.4(3) . . . . ?
C9 C1 C2 C4 87.9(3) . . . . ?
C4 C2 C3 C8 -175.3(2) . . . . ?
C1 C2 C3 C8 5.3(3) . . . . ?
C4 C2 C3 C7 6.9(4) . . . . ?
C1 C2 C3 C7 -172.5(2) . . . . ?
C3 C2 C4 C5 -177.3(2) . . . . ?
C1 C2 C4 C5 2.0(3) . . . . ?
C3 C2 C4 C6 6.8(4) . . . . ?
C1 C2 C4 C6 -173.9(2) . . . . ?
O1 C1 C9 C14 -171.8(2) . . . . ?
C2 C1 C9 C14 7.9(3) . . . . ?
O1 C1 C9 C10 6.9(4) . . . . ?
C2 C1 C9 C10 -173.5(2) . . . . ?
C14 C9 C10 C11 0.8(4) . . . . ?
C1 C9 C10 C11 -177.9(2) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -1.6(4) . . . . ?
C10 C11 C12 Br1 177.4(2) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
Br1 C12 C13 C14 -177.9(2) . . . . ?
C12 C13 C14 C9 0.4(4) . . . . ?
C10 C9 C14 C13 -1.3(4) . . . . ?
C1 C9 C14 C13 177.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H21 N3 0.78(5) 2.29(5) 3.054(4) 166(4) 2_446
O2 H22 N3 0.71(4) 2.37(4) 3.019(3) 153(4) 4_656

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_yak388
_database_code_depnum_ccdc_archive 'CCDC 1575001'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 N4 O Rb'
_chemical_formula_sum            'C15 H7 N4 O Rb'
_chemical_formula_weight         344.72

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'
Rb Rb -0.4688 1.6079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   16.9587(6)
_cell_length_b                   9.9439(3)
_cell_length_c                   8.5740(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.445(3)
_cell_angle_gamma                90
_cell_volume                     1433.69(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1456
_cell_measurement_theta_min      3
_cell_measurement_theta_max      60

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    4.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.386
_exptl_absorpt_correction_T_max  0.409
_exptl_absorpt_special_details   ?

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10687
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.168
_diffrn_reflns_theta_max         72.891
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2855
_reflns_number_gt                1867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0315P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2855
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Rb1 Rb 0.41677(2) 0.86809(3) 0.13713(4) 0.05665(12) Uani 1 1 d . . . . .
O1 O 0.32357(13) 0.8962(2) -0.1668(3) 0.0636(6) Uani 1 1 d . . . . .
N1 N 0.42195(17) 0.9046(3) -0.5022(3) 0.0630(7) Uani 1 1 d . . . . .
N2 N 0.44446(17) 1.3315(3) -0.4241(4) 0.0716(9) Uani 1 1 d . . . . .
N3 N 0.28738(17) 1.4538(3) -0.2784(4) 0.0645(8) Uani 1 1 d . . . . .
N4 N 0.14309(19) 1.1536(3) -0.0842(4) 0.0738(9) Uani 1 1 d . . . . .
C1 C 0.30258(15) 1.1026(3) -0.2973(3) 0.0385(6) Uani 1 1 d . . . . .
C2 C 0.27995(17) 0.9571(3) -0.2673(3) 0.0423(7) Uani 1 1 d . . . . .
C3 C 0.36806(16) 1.1153(3) -0.3803(3) 0.0417(6) Uani 1 1 d . . . . .
C4 C 0.25946(16) 1.2038(3) -0.2375(3) 0.0425(6) Uani 1 1 d . . . . .
C5 C 0.19503(19) 1.1744(3) -0.1521(4) 0.0486(7) Uani 1 1 d . . . . .
C6 C 0.27478(17) 1.3425(3) -0.2600(3) 0.0462(7) Uani 1 1 d . . . . .
C7 C 0.40843(17) 1.2372(3) -0.4048(4) 0.0486(8) Uani 1 1 d . . . . .
C8 C 0.39859(18) 0.9995(3) -0.4477(4) 0.0473(7) Uani 1 1 d . . . . .
C9 C 0.21175(15) 0.8961(3) -0.3632(3) 0.0387(6) Uani 1 1 d . . . . .
C10 C 0.15928(17) 0.9684(3) -0.4691(3) 0.0472(7) Uani 1 1 d . . . . .
H10 H 0.1662 1.0605 -0.4800 0.057 Uiso 1 1 calc R U . . .
C11 C 0.09691(19) 0.9041(3) -0.5580(4) 0.0563(8) Uani 1 1 d . . . . .
H11 H 0.0615 0.9541 -0.6269 0.068 Uiso 1 1 calc R U . . .
C12 C 0.08585(19) 0.7661(4) -0.5468(4) 0.0549(8) Uani 1 1 d . . . . .
C13 C 0.13885(19) 0.6950(3) -0.4414(4) 0.0550(8) Uani 1 1 d . . . . .
H13 H 0.1328 0.6024 -0.4326 0.066 Uiso 1 1 calc R U . . .
C14 C 0.20014(17) 0.7580(3) -0.3495(4) 0.0481(7) Uani 1 1 d . . . . .
H14 H 0.2342 0.7083 -0.2776 0.058 Uiso 1 1 calc R U . . .
C15 C 0.0187(2) 0.6954(4) -0.6451(4) 0.0814(12) Uani 1 1 d . . . . .
H15A H 0.0380 0.6139 -0.6867 0.122 Uiso 1 1 calc R U . . .
H15B H -0.0028 0.7528 -0.7302 0.122 Uiso 1 1 calc R U . . .
H15C H -0.0222 0.6743 -0.5812 0.122 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Rb1 O1 2.881(2) . ?
Rb1 N3 2.981(3) 4_586 ?
Rb1 N1 2.969(3) 4_576 ?
Rb1 N2 3.080(3) 4_586 ?
Rb1 N1 3.104(3) 1_556 ?
Rb1 N2 3.181(3) 2_644 ?
Rb1 O1 3.594(2) 4_576 ?
Rb1 C7 3.659(3) 3_675 ?
Rb1 C8 3.732(3) 4_576 ?
Rb1 Rb1 4.7012(7) 3_675 ?
Rb1 Rb1 4.8881(3) 4_576 ?
Rb1 Rb1 4.8881(3) 4_575 ?
O1 C2 1.221(3) . ?
O1 Rb1 3.594(2) 4_575 ?
N1 C8 1.146(4) . ?
N1 Rb1 2.969(3) 4_575 ?
N1 Rb1 3.104(3) 1_554 ?
N2 C7 1.143(4) . ?
N2 Rb1 3.080(3) 4_585 ?
N2 Rb1 3.181(3) 2_654 ?
N3 C6 1.142(4) . ?
N3 Rb1 2.981(3) 4_585 ?
N4 C5 1.136(4) . ?
C1 C4 1.381(4) . ?
C1 C3 1.400(4) . ?
C1 C2 1.527(4) . ?
C2 C9 1.462(4) . ?
C3 C8 1.416(4) . ?
C3 C7 1.422(4) . ?
C4 C5 1.422(4) . ?
C4 C6 1.422(4) . ?
C7 Rb1 3.659(3) 3_675 ?
C8 Rb1 3.732(3) 4_575 ?
C9 C10 1.387(4) . ?
C9 C14 1.394(4) . ?
C10 C11 1.378(4) . ?
C11 C12 1.389(5) . ?
C12 C13 1.384(5) . ?
C12 C15 1.501(5) . ?
C13 C14 1.372(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
O1 Rb1 N3 80.05(8) . 4_586 ?
O1 Rb1 N1 76.46(7) . 4_576 ?
N3 Rb1 N1 134.53(8) 4_586 4_576 ?
O1 Rb1 N2 80.19(8) . 4_586 ?
N3 Rb1 N2 66.33(7) 4_586 4_586 ?
N1 Rb1 N2 143.54(8) 4_576 4_586 ?
O1 Rb1 N1 146.23(7) . 1_556 ?
N3 Rb1 N1 67.37(8) 4_586 1_556 ?
N1 Rb1 N1 120.62(6) 4_576 1_556 ?
N2 Rb1 N1 94.08(8) 4_586 1_556 ?
O1 Rb1 N2 81.47(8) . 2_644 ?
N3 Rb1 N2 146.09(8) 4_586 2_644 ?
N1 Rb1 N2 66.54(7) 4_576 2_644 ?
N2 Rb1 N2 82.68(8) 4_586 2_644 ?
N1 Rb1 N2 131.15(8) 1_556 2_644 ?
O1 Rb1 O1 105.72(6) . 4_576 ?
N3 Rb1 O1 86.48(6) 4_586 4_576 ?
N1 Rb1 O1 63.78(6) 4_576 4_576 ?
N2 Rb1 O1 151.04(6) 4_586 4_576 ?
N1 Rb1 O1 64.97(6) 1_556 4_576 ?
N2 Rb1 O1 126.00(6) 2_644 4_576 ?
O1 Rb1 C7 154.16(7) . 3_675 ?
N3 Rb1 C7 125.43(8) 4_586 3_675 ?
N1 Rb1 C7 85.83(8) 4_576 3_675 ?
N2 Rb1 C7 104.80(8) 4_586 3_675 ?
N1 Rb1 C7 59.50(7) 1_556 3_675 ?
N2 Rb1 C7 74.22(8) 2_644 3_675 ?
O1 Rb1 C7 82.36(6) 4_576 3_675 ?
O1 Rb1 C8 84.08(6) . 4_576 ?
N3 Rb1 C8 125.75(7) 4_586 4_576 ?
N1 Rb1 C8 14.77(7) 4_576 4_576 ?
N2 Rb1 C8 158.04(8) 4_586 4_576 ?
N1 Rb1 C8 107.44(6) 1_556 4_576 ?
N2 Rb1 C8 79.90(7) 2_644 4_576 ?
O1 Rb1 C8 49.06(6) 4_576 4_576 ?
C7 Rb1 C8 83.20(7) 3_675 4_576 ?
O1 Rb1 Rb1 77.76(4) . 3_675 ?
N3 Rb1 Rb1 107.37(5) 4_586 3_675 ?
N1 Rb1 Rb1 104.92(5) 4_576 3_675 ?
N2 Rb1 Rb1 42.16(5) 4_586 3_675 ?
N1 Rb1 Rb1 119.46(5) 1_556 3_675 ?
N2 Rb1 Rb1 40.52(5) 2_644 3_675 ?
O1 Rb1 Rb1 166.14(4) 4_576 3_675 ?
C7 Rb1 Rb1 89.04(5) 3_675 3_675 ?
C8 Rb1 Rb1 119.27(5) 4_576 3_675 ?
O1 Rb1 Rb1 141.04(4) . 4_576 ?
N3 Rb1 Rb1 89.36(6) 4_586 4_576 ?
N1 Rb1 Rb1 85.26(6) 4_576 4_576 ?
N2 Rb1 Rb1 129.26(6) 4_586 4_576 ?
N1 Rb1 Rb1 35.47(5) 1_556 4_576 ?
N2 Rb1 Rb1 122.19(6) 2_644 4_576 ?
O1 Rb1 Rb1 35.76(3) 4_576 4_576 ?
C7 Rb1 Rb1 53.45(5) 3_675 4_576 ?
C8 Rb1 Rb1 72.00(5) 4_576 4_576 ?
Rb1 Rb1 Rb1 140.808(8) 3_675 4_576 ?
O1 Rb1 Rb1 46.81(5) . 4_575 ?
N3 Rb1 Rb1 125.59(6) 4_586 4_575 ?
N1 Rb1 Rb1 37.34(6) 4_576 4_575 ?
N2 Rb1 Rb1 107.41(6) 4_586 4_575 ?
N1 Rb1 Rb1 157.95(5) 1_556 4_575 ?
N2 Rb1 Rb1 50.02(6) 2_644 4_575 ?
O1 Rb1 Rb1 96.25(4) 4_576 4_575 ?
C7 Rb1 Rb1 108.70(5) 3_675 4_575 ?
C8 Rb1 Rb1 50.79(5) 4_576 4_575 ?
Rb1 Rb1 Rb1 76.184(6) 3_675 4_575 ?
Rb1 Rb1 Rb1 122.570(13) 4_576 4_575 ?
C2 O1 Rb1 153.8(2) . . ?
C2 O1 Rb1 107.21(19) . 4_575 ?
Rb1 O1 Rb1 97.42(6) . 4_575 ?
C8 N1 Rb1 123.9(2) . 4_575 ?
C8 N1 Rb1 122.4(2) . 1_554 ?
Rb1 N1 Rb1 107.19(9) 4_575 1_554 ?
C7 N2 Rb1 132.4(2) . 4_585 ?
C7 N2 Rb1 128.8(2) . 2_654 ?
Rb1 N2 Rb1 97.32(8) 4_585 2_654 ?
C6 N3 Rb1 140.0(2) . 4_585 ?
C4 C1 C3 128.0(2) . . ?
C4 C1 C2 118.1(2) . . ?
C3 C1 C2 113.9(2) . . ?
O1 C2 C9 123.6(3) . . ?
O1 C2 C1 116.5(3) . . ?
C9 C2 C1 119.8(2) . . ?
C1 C3 C8 119.3(2) . . ?
C1 C3 C7 125.5(3) . . ?
C8 C3 C7 115.1(2) . . ?
C1 C4 C5 121.4(3) . . ?
C1 C4 C6 122.8(3) . . ?
C5 C4 C6 115.8(2) . . ?
N4 C5 C4 178.6(3) . . ?
N3 C6 C4 179.7(3) . . ?
N2 C7 C3 176.4(3) . . ?
N2 C7 Rb1 85.4(2) . 3_675 ?
C3 C7 Rb1 91.69(17) . 3_675 ?
N1 C8 C3 178.7(3) . . ?
N1 C8 Rb1 41.33(18) . 4_575 ?
C3 C8 Rb1 137.92(19) . 4_575 ?
C10 C9 C14 118.7(3) . . ?
C10 C9 C2 123.1(3) . . ?
C14 C9 C2 118.2(2) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 C12 121.4(3) . . ?
C13 C12 C11 117.9(3) . . ?
C13 C12 C15 120.6(3) . . ?
C11 C12 C15 121.5(3) . . ?
C14 C13 C12 121.4(3) . . ?
C13 C14 C9 120.4(3) . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_yak389
_database_code_depnum_ccdc_archive 'CCDC 1575088'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 K N4 O2'
_chemical_formula_sum            'C15 H7 K N4 O2'
_chemical_formula_weight         314.35

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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.1407(5)
_cell_length_b                   15.8712(4)
_cell_length_c                   7.1612(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.971(3)
_cell_angle_gamma                90
_cell_volume                     1487.91(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3287
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      65.5

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    3.240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_T_max  0.519

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            11368
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.378
_diffrn_reflns_theta_max         73.116
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2932
_reflns_number_gt                2147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.99008(3) 0.26980(2) 0.92941(5) 0.04410(15) Uani 1 1 d . . . . .
O1 O 0.83865(10) 0.32393(8) 0.6677(2) 0.0595(4) Uani 1 1 d . . . . .
O2 O 0.38472(12) 0.27277(12) 0.3061(3) 0.0773(5) Uani 1 1 d . . . . .
N1 N 0.66917(19) 0.46877(15) 0.9833(3) 0.0820(6) Uani 1 1 d . . . . .
N2 N 0.86127(15) 0.66332(12) 0.7835(3) 0.0668(5) Uani 1 1 d . . . . .
N3 N 0.91964(14) 0.63060(10) 0.3414(3) 0.0555(4) Uani 1 1 d . . . . .
N4 N 0.89865(15) 0.37029(11) 0.1926(3) 0.0589(5) Uani 1 1 d . . . . .
C1 C 0.80461(12) 0.46427(11) 0.5833(2) 0.0376(4) Uani 1 1 d . . . . .
C2 C 0.77377(14) 0.37170(10) 0.5955(3) 0.0394(4) Uani 1 1 d . . . . .
C3 C 0.78280(14) 0.51624(11) 0.7297(3) 0.0427(4) Uani 1 1 d . . . . .
C4 C 0.85639(13) 0.48418(11) 0.4274(2) 0.0394(4) Uani 1 1 d . . . . .
C5 C 0.87859(14) 0.42101(12) 0.2972(3) 0.0438(4) Uani 1 1 d . . . . .
C6 C 0.89089(13) 0.56594(11) 0.3840(2) 0.0401(4) Uani 1 1 d . . . . .
C7 C 0.82440(14) 0.59858(13) 0.7563(3) 0.0474(4) Uani 1 1 d . . . . .
C8 C 0.72050(17) 0.48882(13) 0.8704(3) 0.0520(5) Uani 1 1 d . . . . .
C9 C 0.67327(13) 0.34524(11) 0.5181(2) 0.0388(4) Uani 1 1 d . . . . .
C10 C 0.64677(15) 0.26008(12) 0.5218(3) 0.0436(4) Uani 1 1 d . . . . .
H10 H 0.6942 0.2210 0.5723 0.052 Uiso 1 1 calc R U . . .
C11 C 0.55156(16) 0.23323(13) 0.4519(3) 0.0510(5) Uani 1 1 d . . . . .
H11 H 0.5348 0.1763 0.4539 0.061 Uiso 1 1 calc R U . . .
C12 C 0.48068(15) 0.29172(15) 0.3784(3) 0.0535(5) Uani 1 1 d . . . . .
C13 C 0.50653(16) 0.37657(14) 0.3713(3) 0.0565(5) Uani 1 1 d . . . . .
H13 H 0.4590 0.4155 0.3203 0.068 Uiso 1 1 calc R U . . .
C14 C 0.60168(14) 0.40292(12) 0.4391(3) 0.0482(5) Uani 1 1 d . . . . .
H14 H 0.6189 0.4596 0.4327 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3512(2) 0.1872(2) 0.3135(5) 0.0926(9) Uani 1 1 d . . . . .
H15A H 0.3948 0.1521 0.2460 0.139 Uiso 1 1 calc R U . . .
H15B H 0.2823 0.1830 0.2577 0.139 Uiso 1 1 calc R U . . .
H15C H 0.3539 0.1691 0.4417 0.139 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O1 2.7502(14) . ?
K1 N4 2.8164(18) 1_556 ?
K1 N3 2.8398(18) 3_766 ?
K1 N2 2.911(2) 3_767 ?
K1 N3 2.9403(18) 2_746 ?
K1 N4 2.9850(19) 4_566 ?
K1 N2 3.084(2) 2_746 ?
K1 O1 3.1103(16) 4_566 ?
K1 C5 3.4604(19) 4_566 ?
K1 K1 3.63535(16) 4_566 ?
K1 K1 3.63539(16) 4_565 ?
O1 C2 1.222(2) . ?
O1 K1 3.1103(16) 4_565 ?
O2 C12 1.355(3) . ?
O2 C15 1.430(3) . ?
N1 C8 1.142(3) . ?
N2 C7 1.146(3) . ?
N2 K1 2.911(2) 3_767 ?
N2 K1 3.084(2) 2_756 ?
N3 C6 1.144(2) . ?
N3 K1 2.8398(18) 3_766 ?
N3 K1 2.9404(18) 2_756 ?
N4 C5 1.146(2) . ?
N4 K1 2.8163(18) 1_554 ?
N4 K1 2.9851(19) 4_565 ?
C1 C3 1.383(2) . ?
C1 C4 1.393(2) . ?
C1 C2 1.529(2) . ?
C2 C9 1.449(3) . ?
C3 C8 1.421(3) . ?
C3 C7 1.423(3) . ?
C4 C5 1.417(3) . ?
C4 C6 1.418(2) . ?
C5 K1 3.4604(19) 4_565 ?
C9 C14 1.396(3) . ?
C9 C10 1.397(2) . ?
C10 C11 1.374(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(3) . ?
C13 C14 1.367(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 K1 N4 87.35(5) . 1_556 ?
O1 K1 N3 71.41(5) . 3_766 ?
N4 K1 N3 111.68(5) 1_556 3_766 ?
O1 K1 N2 140.27(5) . 3_767 ?
N4 K1 N2 67.67(6) 1_556 3_767 ?
N3 K1 N2 89.13(6) 3_766 3_767 ?
O1 K1 N3 148.02(5) . 2_746 ?
N4 K1 N3 103.11(5) 1_556 2_746 ?
N3 K1 N3 128.85(7) 3_766 2_746 ?
N2 K1 N3 70.49(5) 3_767 2_746 ?
O1 K1 N4 67.28(5) . 4_566 ?
N4 K1 N4 128.90(7) 1_556 4_566 ?
N3 K1 N4 101.42(5) 3_766 4_566 ?
N2 K1 N4 152.29(6) 3_767 4_566 ?
N3 K1 N4 83.14(5) 2_746 4_566 ?
O1 K1 N2 106.62(5) . 2_746 ?
N4 K1 N2 165.09(6) 1_556 2_746 ?
N3 K1 N2 69.36(5) 3_766 2_746 ?
N2 K1 N2 97.70(7) 3_767 2_746 ?
N3 K1 N2 67.80(5) 2_746 2_746 ?
N4 K1 N2 63.38(5) 4_566 2_746 ?
O1 K1 O1 93.66(5) . 4_566 ?
N4 K1 O1 64.75(5) 1_556 4_566 ?
N3 K1 O1 164.99(5) 3_766 4_566 ?
N2 K1 O1 102.06(5) 3_767 4_566 ?
N3 K1 O1 65.21(4) 2_746 4_566 ?
N4 K1 O1 73.16(4) 4_566 4_566 ?
N2 K1 O1 118.16(5) 2_746 4_566 ?
O1 K1 C5 79.79(4) . 4_566 ?
N4 K1 C5 118.93(5) 1_556 4_566 ?
N3 K1 C5 119.49(5) 3_766 4_566 ?
N2 K1 C5 139.00(5) 3_767 4_566 ?
N3 K1 C5 68.65(5) 2_746 4_566 ?
N4 K1 C5 18.66(4) 4_566 4_566 ?
N2 K1 C5 69.90(5) 2_746 4_566 ?
O1 K1 C5 57.03(4) 4_566 4_566 ?
O1 K1 K1 131.56(4) . 4_566 ?
N4 K1 K1 53.30(4) 1_556 4_566 ?
N3 K1 K1 143.56(4) 3_766 4_566 ?
N2 K1 K1 54.88(4) 3_767 4_566 ?
N3 K1 K1 49.81(4) 2_746 4_566 ?
N4 K1 K1 113.35(4) 4_566 4_566 ?
N2 K1 K1 116.50(4) 2_746 4_566 ?
O1 K1 K1 47.33(3) 4_566 4_566 ?
C5 K1 K1 94.71(3) 4_566 4_566 ?
O1 K1 K1 56.26(4) . 4_565 ?
N4 K1 K1 142.51(4) 1_556 4_565 ?
N3 K1 K1 52.27(4) 3_766 4_565 ?
N2 K1 K1 134.54(4) 3_767 4_565 ?
N3 K1 K1 112.67(4) 2_746 4_565 ?
N4 K1 K1 49.15(4) 4_566 4_565 ?
N2 K1 K1 50.52(4) 2_746 4_565 ?
O1 K1 K1 120.82(3) 4_566 4_565 ?
C5 K1 K1 67.37(3) 4_566 4_565 ?
K1 K1 K1 160.08(2) 4_566 4_565 ?
C2 O1 K1 156.85(13) . . ?
C2 O1 K1 121.37(13) . 4_565 ?
K1 O1 K1 76.40(3) . 4_565 ?
C12 O2 C15 118.5(2) . . ?
C7 N2 K1 134.06(18) . 3_767 ?
C7 N2 K1 133.16(16) . 2_756 ?
K1 N2 K1 74.60(5) 3_767 2_756 ?
C6 N3 K1 148.05(15) . 3_766 ?
C6 N3 K1 130.67(15) . 2_756 ?
K1 N3 K1 77.92(4) 3_766 2_756 ?
C5 N4 K1 166.17(16) . 1_554 ?
C5 N4 K1 104.84(14) . 4_565 ?
K1 N4 K1 77.54(4) 1_554 4_565 ?
C3 C1 C4 128.30(16) . . ?
C3 C1 C2 117.16(16) . . ?
C4 C1 C2 114.45(15) . . ?
O1 C2 C9 124.16(15) . . ?
O1 C2 C1 116.22(15) . . ?
C9 C2 C1 119.60(15) . . ?
C1 C3 C8 121.66(16) . . ?
C1 C3 C7 123.13(17) . . ?
C8 C3 C7 115.14(17) . . ?
C1 C4 C5 120.66(16) . . ?
C1 C4 C6 124.83(16) . . ?
C5 C4 C6 114.52(16) . . ?
N4 C5 C4 178.6(2) . . ?
N4 C5 K1 56.50(12) . 4_565 ?
C4 C5 K1 123.06(12) . 4_565 ?
N3 C6 C4 177.0(2) . . ?
N2 C7 C3 176.8(2) . . ?
N1 C8 C3 178.2(2) . . ?
C14 C9 C10 118.81(17) . . ?
C14 C9 C2 121.63(16) . . ?
C10 C9 C2 119.56(16) . . ?
C11 C10 C9 120.90(19) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.43(19) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
O2 C12 C11 124.7(2) . . ?
O2 C12 C13 115.0(2) . . ?
C11 C12 C13 120.27(18) . . ?
C14 C13 C12 120.13(19) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.43(18) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_az218
_audit_block_doi                 10.5517/ccdc.csd.cc1kqyqy
_database_code_depnum_ccdc_archive 'CCDC 1452031'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.6b01040 2016
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Caesium 2-benzoyl-1,1,3,3-tetracyanopropenide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H5 Cs N4 O'
_chemical_formula_weight         378.13

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'
Cs Cs -0.7457 7.9052 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   ' P21/c'

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

_cell_length_a                   9.6659(4)
_cell_length_b                   18.4180(5)
_cell_length_c                   8.3669(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.607(3)
_cell_angle_gamma                90.00
_cell_volume                     1419.75(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    20.358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.0740
_exptl_absorpt_correction_T_max  0.5220


_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5718
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.80
_diffrn_reflns_theta_max         71.96
_reflns_number_total             2644
_reflns_number_gt                1895
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0959P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2644
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs 0.21695(6) 0.16223(2) 0.35502(7) 0.0779(2) Uani 1 1 d . . .
O1 O 0.4966(6) 0.0926(3) 0.5744(6) 0.0736(13) Uani 1 1 d . . .
N1 N 0.8558(10) 0.3250(3) 0.7219(11) 0.092(2) Uani 1 1 d . . .
N2 N 0.4770(11) 0.2390(4) 0.8255(13) 0.105(3) Uani 1 1 d . . .
N3 N 0.8421(9) -0.0090(3) 0.5238(10) 0.0832(19) Uani 1 1 d . . .
N4 N 1.0678(9) 0.1964(4) 0.6460(10) 0.0856(19) Uani 1 1 d . . .
C1 C 0.7273(7) 0.1444(3) 0.6872(7) 0.0532(13) Uani 1 1 d . . .
C2 C 0.6115(7) 0.0875(3) 0.6829(8) 0.0551(14) Uani 1 1 d . . .
C3 C 0.6430(8) 0.0295(3) 0.8111(8) 0.0567(14) Uani 1 1 d . . .
C4 C 0.5426(8) -0.0261(4) 0.7962(8) 0.0646(16) Uani 1 1 d . . .
H4 H 0.4587 -0.0265 0.7051 0.077 Uiso 1 1 calc . . .
C5 C 0.5654(10) -0.0808(4) 0.9139(10) 0.074(2) Uani 1 1 d . . .
H5 H 0.4984 -0.1181 0.9028 0.089 Uiso 1 1 calc . . .
C6 C 0.6903(12) -0.0787(5) 1.0487(11) 0.089(3) Uani 1 1 d . . .
H6 H 0.7073 -0.1152 1.1291 0.107 Uiso 1 1 calc . . .
C7 C 0.7880(12) -0.0248(6) 1.0662(12) 0.098(3) Uani 1 1 d . . .
H7 H 0.8706 -0.0244 1.1589 0.118 Uiso 1 1 calc . . .
C8 C 0.7666(9) 0.0304(4) 0.9468(9) 0.0723(19) Uani 1 1 d . . .
H8 H 0.8349 0.0672 0.9588 0.087 Uiso 1 1 calc . . .
C9 C 0.7014(8) 0.2136(3) 0.7361(8) 0.0595(15) Uani 1 1 d . . .
C10 C 0.7890(9) 0.2750(4) 0.7298(9) 0.0673(17) Uani 1 1 d . . .
C11 C 0.5746(10) 0.2280(4) 0.7850(10) 0.0715(19) Uani 1 1 d . . .
C12 C 0.8426(8) 0.1209(3) 0.6352(8) 0.0569(14) Uani 1 1 d . . .
C13 C 0.9663(8) 0.1638(3) 0.6394(9) 0.0629(15) Uani 1 1 d . . .
C14 C 0.8433(8) 0.0491(4) 0.5731(9) 0.0635(16) 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
Cs1 O1 3.052(5) . ?
Cs1 N3 3.110(7) 3_656 ?
Cs1 N2 3.173(8) 4_565 ?
Cs1 N4 3.224(6) 4_465 ?
Cs1 N4 3.244(8) 1_455 ?
Cs1 N1 3.336(9) 4_465 ?
Cs1 C5 3.821(8) 3_656 ?
Cs1 C13 3.875(7) 1_455 ?
Cs1 C4 3.881(7) 3_656 ?
Cs1 Cs1 5.2872(6) 4_566 ?
Cs1 Cs1 5.2872(6) 4_565 ?
O1 C2 1.207(8) . ?
N1 C10 1.137(10) . ?
N1 Cs1 3.336(9) 4_666 ?
N2 C11 1.113(11) . ?
N2 Cs1 3.173(8) 4_566 ?
N3 C14 1.145(9) . ?
N3 Cs1 3.110(7) 3_656 ?
N4 C13 1.136(10) . ?
N4 Cs1 3.224(6) 4_666 ?
N4 Cs1 3.244(7) 1_655 ?
C1 C12 1.383(10) . ?
C1 C9 1.385(9) . ?
C1 C2 1.525(9) . ?
C2 C3 1.478(8) . ?
C3 C8 1.377(11) . ?
C3 C4 1.391(10) . ?
C4 C5 1.379(10) . ?
C4 Cs1 3.881(7) 3_656 ?
C5 C6 1.381(14) . ?
C5 Cs1 3.821(8) 3_656 ?
C6 C7 1.346(15) . ?
C7 C8 1.397(11) . ?
C9 C10 1.424(10) . ?
C9 C11 1.429(12) . ?
C12 C14 1.423(9) . ?
C12 C13 1.425(10) . ?
C13 Cs1 3.875(7) 1_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cs1 N3 68.85(19) . 3_656 ?
O1 Cs1 N2 73.1(2) . 4_565 ?
N3 Cs1 N2 140.7(2) 3_656 4_565 ?
O1 Cs1 N4 146.60(18) . 4_465 ?
N3 Cs1 N4 144.5(2) 3_656 4_465 ?
N2 Cs1 N4 74.3(2) 4_565 4_465 ?
O1 Cs1 N4 98.28(19) . 1_455 ?
N3 Cs1 N4 76.35(18) 3_656 1_455 ?
N2 Cs1 N4 119.3(2) 4_565 1_455 ?
N4 Cs1 N4 91.33(16) 4_465 1_455 ?
O1 Cs1 N1 151.32(17) . 4_465 ?
N3 Cs1 N1 84.05(19) 3_656 4_465 ?
N2 Cs1 N1 135.0(2) 4_565 4_465 ?
N4 Cs1 N1 60.70(19) 4_465 4_465 ?
N4 Cs1 N1 65.1(2) 1_455 4_465 ?
O1 Cs1 C5 69.15(17) . 3_656 ?
N3 Cs1 C5 91.38(16) 3_656 3_656 ?
N2 Cs1 C5 65.7(2) 4_565 3_656 ?
N4 Cs1 C5 103.48(18) 4_465 3_656 ?
N4 Cs1 C5 165.19(19) 1_455 3_656 ?
N1 Cs1 C5 122.5(2) 4_465 3_656 ?
O1 Cs1 C13 103.79(15) . 1_455 ?
N3 Cs1 C13 66.18(16) 3_656 1_455 ?
N2 Cs1 C13 134.5(2) 4_565 1_455 ?
N4 Cs1 C13 93.83(17) 4_465 1_455 ?
N4 Cs1 C13 15.32(15) 1_455 1_455 ?
N1 Cs1 C13 54.49(20) 4_465 1_455 ?
C5 Cs1 C13 157.27(14) 3_656 1_455 ?
O1 Cs1 C4 54.27(15) . 3_656 ?
N3 Cs1 C4 72.98(16) 3_656 3_656 ?
N2 Cs1 C4 77.2(2) 4_565 3_656 ?
N4 Cs1 C4 123.95(17) 4_465 3_656 ?
N4 Cs1 C4 144.65(18) 1_455 3_656 ?
N1 Cs1 C4 127.31(17) 4_465 3_656 ?
C5 Cs1 C4 20.61(15) 3_656 3_656 ?
C13 Cs1 C4 138.78(14) 1_455 3_656 ?
O1 Cs1 Cs1 89.60(10) . 4_566 ?
N3 Cs1 Cs1 104.65(13) 3_656 4_566 ?
N2 Cs1 Cs1 84.29(18) 4_565 4_566 ?
N4 Cs1 Cs1 80.11(15) 4_465 4_566 ?
N4 Cs1 Cs1 35.05(12) 1_455 4_566 ?
N1 Cs1 Cs1 88.31(14) 4_465 4_566 ?
C5 Cs1 Cs1 146.89(13) 3_656 4_566 ?
C13 Cs1 Cs1 50.20(10) 1_455 4_566 ?
C4 Cs1 Cs1 142.76(11) 3_656 4_566 ?
O1 Cs1 Cs1 121.38(11) . 4_565 ?
N3 Cs1 Cs1 148.98(14) 3_656 4_565 ?
N2 Cs1 Cs1 53.00(19) 4_565 4_565 ?
N4 Cs1 Cs1 35.30(14) 4_465 4_565 ?
N4 Cs1 Cs1 125.56(14) 1_455 4_565 ?
N1 Cs1 Cs1 86.73(15) 4_465 4_565 ?
C5 Cs1 Cs1 69.04(11) 3_656 4_565 ?
C13 Cs1 Cs1 129.10(11) 1_455 4_565 ?
C4 Cs1 Cs1 89.64(10) 3_656 4_565 ?
Cs1 Cs1 Cs1 104.602(16) 4_566 4_565 ?
C2 O1 Cs1 158.6(5) . . ?
C10 N1 Cs1 126.4(6) . 4_666 ?
C11 N2 Cs1 153.2(7) . 4_566 ?
C14 N3 Cs1 135.4(6) . 3_656 ?
C13 N4 Cs1 133.6(6) . 4_666 ?
C13 N4 Cs1 115.7(5) . 1_655 ?
Cs1 N4 Cs1 109.7(2) 4_666 1_655 ?
C12 C1 C9 128.0(6) . . ?
C12 C1 C2 115.7(5) . . ?
C9 C1 C2 116.3(6) . . ?
O1 C2 C3 122.9(6) . . ?
O1 C2 C1 117.8(6) . . ?
C3 C2 C1 119.3(5) . . ?
C8 C3 C4 119.3(6) . . ?
C8 C3 C2 121.8(6) . . ?
C4 C3 C2 118.8(6) . . ?
C5 C4 C3 121.2(7) . . ?
C5 C4 Cs1 77.3(4) . 3_656 ?
C3 C4 Cs1 92.0(4) . 3_656 ?
C4 C5 C6 118.3(7) . . ?
C4 C5 Cs1 82.1(4) . 3_656 ?
C6 C5 Cs1 89.5(5) . 3_656 ?
C7 C6 C5 121.4(7) . . ?
C6 C7 C8 120.8(9) . . ?
C3 C8 C7 119.0(8) . . ?
C1 C9 C10 123.9(7) . . ?
C1 C9 C11 120.2(6) . . ?
C10 C9 C11 115.7(6) . . ?
N1 C10 C9 178.2(9) . . ?
N2 C11 C9 178.9(10) . . ?
C1 C12 C14 119.9(6) . . ?
C1 C12 C13 124.7(6) . . ?
C14 C12 C13 115.4(6) . . ?
N4 C13 C12 177.7(8) . . ?
N4 C13 Cs1 48.9(5) . 1_655 ?
C12 C13 Cs1 131.0(4) . 1_655 ?
N3 C14 C12 179.0(8) . . ?

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        71.96
_diffrn_measured_fraction_theta_full 0.949
_refine_diff_density_max         1.819
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.181
_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1574998'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H5 K N4 O'
_chemical_formula_sum            'C14 H5 K N4 O'
_chemical_formula_weight         284.32

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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.4796(4)
_cell_length_b                   16.2292(10)
_cell_length_c                   7.1308(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.058(4)
_cell_angle_gamma                90
_cell_volume                     1315.39(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2654
_cell_measurement_theta_min      4.2
_cell_measurement_theta_max      64.2

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .16
_exptl_crystal_size_mid          .09
_exptl_crystal_size_min          .05
_exptl_absorpt_coefficient_mu    3.545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.77
_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            8998
_diffrn_reflns_av_unetI/netI     0.1891
_diffrn_reflns_av_R_equivalents  0.1337
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.889
_diffrn_reflns_theta_max         66.844
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2316
_reflns_number_gt                946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00108(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2316
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1430
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   0.688
_refine_ls_restrained_S_all      0.688
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.50057(9) 0.26885(5) 1.07084(14) 0.0459(3) Uani 1 1 d . . . . .
O1 O 0.3271(3) 0.17790(16) 0.7831(4) 0.0547(9) Uani 1 1 d . . . . .
N1 N 0.3962(3) -0.1295(2) 1.1221(5) 0.0523(10) Uani 1 1 d . . . . .
N2 N 0.3960(3) 0.1286(2) 1.2701(6) 0.0564(11) Uani 1 1 d . . . . .
N3 N 0.1317(4) 0.0453(2) 0.3755(6) 0.0711(12) Uani 1 1 d . . . . .
N4 N 0.3303(3) -0.1570(2) 0.6542(6) 0.0625(12) Uani 1 1 d . . . . .
C1 C 0.2812(3) 0.0394(2) 0.8381(6) 0.0337(10) Uani 1 1 d . . . . .
C2 C 0.2495(4) 0.1312(2) 0.8166(5) 0.0349(10) Uani 1 1 d . . . . .
C3 C 0.1310(4) 0.1578(2) 0.8433(6) 0.0361(10) Uani 1 1 d . . . . .
C4 C 0.1067(4) 0.2425(2) 0.8437(5) 0.0443(11) Uani 1 1 d . . . . .
H4 H 0.1645 0.2810 0.8281 0.053 Uiso 1 1 calc R U . . .
C5 C -0.0053(4) 0.2671(3) 0.8679(6) 0.0558(13) Uani 1 1 d . . . . .
H5 H -0.0223 0.3231 0.8716 0.067 Uiso 1 1 calc R U . . .
C6 C -0.0916(4) 0.2113(3) 0.8866(7) 0.0615(13) Uani 1 1 d . . . . .
H6 H -0.1670 0.2293 0.8993 0.074 Uiso 1 1 calc R U . . .
C7 C -0.0671(4) 0.1283(3) 0.8868(7) 0.0588(14) Uani 1 1 d . . . . .
H7 H -0.1259 0.0901 0.9001 0.071 Uiso 1 1 calc R U . . .
C8 C 0.0444(4) 0.1016(3) 0.8671(6) 0.0478(12) Uani 1 1 d . . . . .
H8 H 0.0613 0.0456 0.8699 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2539(3) -0.0093(2) 0.6803(7) 0.0386(11) Uani 1 1 d . . . . .
C10 C 0.3405(3) 0.0179(2) 1.0170(6) 0.0350(10) Uani 1 1 d . . . . .
C11 C 0.3700(4) 0.0790(3) 1.1572(7) 0.0381(10) Uani 1 1 d . . . . .
C12 C 0.3719(4) -0.0633(3) 1.0731(6) 0.0363(10) Uani 1 1 d . . . . .
C13 C 0.1863(4) 0.0211(3) 0.5109(8) 0.0461(12) Uani 1 1 d . . . . .
C14 C 0.2945(4) -0.0920(3) 0.6686(6) 0.0439(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
K1 O1 2.802(3) 4_566 ?
K1 N2 2.844(4) 4_565 ?
K1 N1 2.862(4) 2_657 ?
K1 N4 2.944(4) 2_656 ?
K1 N1 2.978(4) 3_657 ?
K1 N2 3.019(4) . ?
K1 O1 3.035(3) . ?
K1 N4 3.137(4) 3_657 ?
K1 C11 3.517(4) . ?
K1 K1 3.6175(3) 4_566 ?
K1 K1 3.6175(3) 4_565 ?
O1 C2 1.218(4) . ?
O1 K1 2.802(3) 4_565 ?
N1 C12 1.152(4) . ?
N1 K1 2.862(4) 2_647 ?
N1 K1 2.978(4) 3_657 ?
N2 C11 1.148(5) . ?
N2 K1 2.844(4) 4_566 ?
N3 C13 1.144(5) . ?
N4 C14 1.142(5) . ?
N4 K1 2.944(4) 2_646 ?
N4 K1 3.137(4) 3_657 ?
C1 C9 1.375(6) . ?
C1 C10 1.404(6) . ?
C1 C2 1.536(5) . ?
C2 C3 1.464(5) . ?
C3 C8 1.377(5) . ?
C3 C4 1.403(5) . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(5) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C14 1.426(6) . ?
C9 C13 1.429(7) . ?
C10 C12 1.410(5) . ?
C10 C11 1.415(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
O1 K1 N2 88.29(10) 4_566 4_565 ?
O1 K1 N1 70.03(10) 4_566 2_657 ?
N2 K1 N1 109.00(10) 4_565 2_657 ?
O1 K1 N4 137.84(10) 4_566 2_656 ?
N2 K1 N4 65.81(11) 4_565 2_656 ?
N1 K1 N4 86.98(12) 2_657 2_656 ?
O1 K1 N1 147.45(9) 4_566 3_657 ?
N2 K1 N1 104.43(11) 4_565 3_657 ?
N1 K1 N1 129.94(14) 2_657 3_657 ?
N4 K1 N1 73.93(11) 2_656 3_657 ?
O1 K1 N2 67.59(9) 4_566 . ?
N2 K1 N2 129.98(15) 4_565 . ?
N1 K1 N2 102.92(12) 2_657 . ?
N4 K1 N2 154.26(11) 2_656 . ?
N1 K1 N2 81.67(9) 3_657 . ?
O1 K1 O1 93.81(9) 4_566 . ?
N2 K1 O1 66.87(9) 4_565 . ?
N1 K1 O1 163.67(10) 2_657 . ?
N4 K1 O1 104.52(11) 2_656 . ?
N1 K1 O1 65.44(9) 3_657 . ?
N2 K1 O1 71.64(10) . . ?
O1 K1 N4 105.39(10) 4_566 3_657 ?
N2 K1 N4 165.63(11) 4_565 3_657 ?
N1 K1 N4 72.65(10) 2_657 3_657 ?
N4 K1 N4 100.37(13) 2_656 3_657 ?
N1 K1 N4 66.28(10) 3_657 3_657 ?
N2 K1 N4 61.41(10) . 3_657 ?
O1 K1 N4 115.52(9) . 3_657 ?
O1 K1 C11 79.81(9) 4_566 . ?
N2 K1 C11 119.96(11) 4_565 . ?
N1 K1 C11 120.77(11) 2_657 . ?
N4 K1 C11 141.56(11) 2_656 . ?
N1 K1 C11 67.84(10) 3_657 . ?
N2 K1 C11 18.26(9) . . ?
O1 K1 C11 55.74(10) . . ?
N4 K1 C11 67.99(10) 3_657 . ?
O1 K1 K1 54.66(7) 4_566 4_566 ?
N2 K1 K1 141.63(8) 4_565 4_566 ?
N1 K1 K1 53.17(8) 2_657 4_566 ?
N4 K1 K1 134.23(9) 2_656 4_566 ?
N1 K1 K1 112.45(8) 3_657 4_566 ?
N2 K1 K1 49.75(8) . 4_566 ?
O1 K1 K1 119.57(6) . 4_566 ?
N4 K1 K1 51.07(7) 3_657 4_566 ?
C11 K1 K1 67.70(8) . 4_566 ?
O1 K1 K1 133.07(7) 4_566 4_565 ?
N2 K1 K1 54.13(8) 4_565 4_565 ?
N1 K1 K1 142.59(8) 2_657 4_565 ?
N4 K1 K1 56.00(9) 2_656 4_565 ?
N1 K1 K1 50.30(7) 3_657 4_565 ?
N2 K1 K1 113.03(9) . 4_565 ?
O1 K1 K1 48.85(6) . 4_565 ?
N4 K1 K1 115.63(8) 3_657 4_565 ?
C11 K1 K1 94.77(8) . 4_565 ?
K1 K1 K1 160.52(5) 4_566 4_565 ?
C2 O1 K1 153.2(3) . 4_565 ?
C2 O1 K1 126.7(3) . . ?
K1 O1 K1 76.49(7) 4_565 . ?
C12 N1 K1 145.7(3) . 2_647 ?
C12 N1 K1 131.5(3) . 3_657 ?
K1 N1 K1 76.52(9) 2_647 3_657 ?
C11 N2 K1 168.5(3) . 4_566 ?
C11 N2 K1 106.2(3) . . ?
K1 N2 K1 76.13(9) 4_566 . ?
C14 N4 K1 134.5(3) . 2_646 ?
C14 N4 K1 132.6(4) . 3_657 ?
K1 N4 K1 72.93(9) 2_646 3_657 ?
C9 C1 C10 128.8(4) . . ?
C9 C1 C2 116.9(4) . . ?
C10 C1 C2 114.2(4) . . ?
O1 C2 C3 124.0(3) . . ?
O1 C2 C1 117.0(3) . . ?
C3 C2 C1 118.9(3) . . ?
C8 C3 C4 120.0(4) . . ?
C8 C3 C2 121.4(4) . . ?
C4 C3 C2 118.6(3) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C3 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C1 C9 C14 123.4(4) . . ?
C1 C9 C13 121.9(3) . . ?
C14 C9 C13 114.7(4) . . ?
C1 C10 C12 124.2(4) . . ?
C1 C10 C11 120.4(3) . . ?
C12 C10 C11 115.4(4) . . ?
N2 C11 C10 178.8(5) . . ?
N2 C11 K1 55.5(3) . . ?
C10 C11 K1 123.8(3) . . ?
N1 C12 C10 178.5(4) . . ?
N3 C13 C9 179.7(6) . . ?
N4 C14 C9 177.0(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
K1 O1 C2 C3 -126.6(5) 4_565 . . . ?
K1 O1 C2 C3 87.2(4) . . . . ?
K1 O1 C2 C1 55.4(8) 4_565 . . . ?
K1 O1 C2 C1 -90.7(4) . . . . ?
C9 C1 C2 O1 -95.8(5) . . . . ?
C10 C1 C2 O1 81.0(5) . . . . ?
C9 C1 C2 C3 86.2(5) . . . . ?
C10 C1 C2 C3 -97.1(4) . . . . ?
O1 C2 C3 C8 175.2(4) . . . . ?
C1 C2 C3 C8 -6.9(6) . . . . ?
O1 C2 C3 C4 -4.7(6) . . . . ?
C1 C2 C3 C4 173.2(4) . . . . ?
C8 C3 C4 C5 -0.2(6) . . . . ?
C2 C3 C4 C5 179.7(4) . . . . ?
C3 C4 C5 C6 -1.5(6) . . . . ?
C4 C5 C6 C7 1.8(7) . . . . ?
C5 C6 C7 C8 -0.3(7) . . . . ?
C6 C7 C8 C3 -1.4(7) . . . . ?
C4 C3 C8 C7 1.6(6) . . . . ?
C2 C3 C8 C7 -178.2(4) . . . . ?
C10 C1 C9 C14 -6.8(7) . . . . ?
C2 C1 C9 C14 169.5(4) . . . . ?
C10 C1 C9 C13 176.1(4) . . . . ?
C2 C1 C9 C13 -7.7(6) . . . . ?
C9 C1 C10 C12 -7.7(7) . . . . ?
C2 C1 C10 C12 176.0(4) . . . . ?
C9 C1 C10 C11 174.0(4) . . . . ?
C2 C1 C10 C11 -2.3(5) . . . . ?
K1 N2 C11 K1 -100.4(18) 4_566 . . . ?
C1 C10 C11 K1 -46.5(5) . . . . ?
C12 C10 C11 K1 135.1(3) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_az284
_audit_block_doi                 10.5517/ccdc.csd.cc1kqys0
_database_code_depnum_ccdc_archive 'CCDC 1452033'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.6b01040 2016
_audit_update_record             
;
2017-10-24 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 Li N4 O2'
_chemical_formula_sum            'C14 H7 Li N4 O2'
_chemical_formula_weight         270.18

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'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7665(3)
_cell_length_b                   9.4171(3)
_cell_length_c                   9.9290(3)
_cell_angle_alpha                63.474(3)
_cell_angle_beta                 76.105(3)
_cell_angle_gamma                67.301(3)
_cell_volume                     674.31(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4050
_cell_measurement_theta_min      4
_cell_measurement_theta_max      70

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .10
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.482
_exptl_absorpt_correction_T_max  0.597

_exptl_special_details           
;
 ?
;



_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            8164
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.995
_diffrn_reflns_theta_max         73.167
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2546
_reflns_number_gt                1877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1276P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2546
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1723
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Li1 Li 0.6169(4) 0.2787(4) 0.2865(4) 0.0455(8) Uani 1 1 d . . . . .
O1 O 0.45692(18) 0.2259(2) 0.2251(2) 0.0547(5) Uani 1 1 d . . . . .
O2 O 0.5047(3) 0.3651(3) 0.4326(3) 0.0855(8) Uani 1 1 d . . . . .
N1 N 0.2220(3) -0.0494(2) 0.5977(2) 0.0593(6) Uani 1 1 d . . . . .
N2 N -0.1840(3) 0.4167(3) 0.5205(3) 0.0816(8) Uani 1 1 d . . . . .
N3 N -0.1251(3) 0.7257(3) 0.2081(3) 0.0827(8) Uani 1 1 d . . . . .
N4 N 0.2706(3) 0.5844(2) -0.0944(2) 0.0567(5) Uani 1 1 d . . . . .
C1 C 0.3277(2) 0.2024(2) 0.2328(2) 0.0385(5) Uani 1 1 d . . . . .
C2 C 0.3213(3) 0.0651(2) 0.2043(2) 0.0414(5) Uani 1 1 d . . . . .
C3 C 0.1734(3) 0.0634(3) 0.1805(3) 0.0534(6) Uani 1 1 d . . . . .
H3 H 0.0752 0.1478 0.1861 0.064 Uiso 1 1 calc R U . . .
C4 C 0.1717(5) -0.0655(4) 0.1480(3) 0.0756(9) Uani 1 1 d . . . . .
H4 H 0.0732 -0.0669 0.1297 0.091 Uiso 1 1 calc R U . . .
C5 C 0.3197(5) -0.1918(4) 0.1433(3) 0.0802(10) Uani 1 1 d . . . . .
H5 H 0.3194 -0.2788 0.1227 0.096 Uiso 1 1 calc R U . . .
C6 C 0.4645(4) -0.1906(3) 0.1681(3) 0.0703(8) Uani 1 1 d . . . . .
H6 H 0.5618 -0.2770 0.1652 0.084 Uiso 1 1 calc R U . . .
C7 C 0.4689(3) -0.0619(3) 0.1979(3) 0.0537(6) Uani 1 1 d . . . . .
H7 H 0.5687 -0.0603 0.2133 0.064 Uiso 1 1 calc R U . . .
C8 C 0.1680(2) 0.3200(2) 0.2755(2) 0.0387(5) Uani 1 1 d . . . . .
C9 C 0.0912(3) 0.2543(2) 0.4181(2) 0.0438(5) Uani 1 1 d . . . . .
C10 C -0.0609(3) 0.3453(3) 0.4745(2) 0.0544(6) Uani 1 1 d . . . . .
C11 C 0.1633(3) 0.0860(2) 0.5189(2) 0.0472(5) Uani 1 1 d . . . . .
C12 C 0.1176(2) 0.4834(2) 0.1674(2) 0.0422(5) Uani 1 1 d . . . . .
C13 C -0.0200(3) 0.6148(3) 0.1919(3) 0.0530(6) Uani 1 1 d . . . . .
C14 C 0.2053(3) 0.5333(2) 0.0234(2) 0.0444(5) Uani 1 1 d . . . . .
H2 H 0.409(4) 0.435(3) 0.450(3) 0.053 Uiso 1 1 d . U . . .
H21 H 0.547(4) 0.345(3) 0.505(3) 0.053 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Li1 O2 1.867(4) . ?
Li1 O1 1.951(4) . ?
Li1 N4 2.038(4) 2_665 ?
Li1 N1 2.046(4) 2_656 ?
O1 C1 1.215(2) . ?
N1 C11 1.140(3) . ?
N1 Li1 2.046(4) 2_656 ?
N2 C10 1.141(3) . ?
N3 C13 1.141(3) . ?
N4 C14 1.147(3) . ?
N4 Li1 2.038(4) 2_665 ?
C1 C2 1.465(3) . ?
C1 C8 1.518(3) . ?
C2 C3 1.380(3) . ?
C2 C7 1.394(3) . ?
C3 C4 1.394(4) . ?
C4 C5 1.389(5) . ?
C5 C6 1.355(5) . ?
C6 C7 1.385(4) . ?
C8 C9 1.386(3) . ?
C8 C12 1.394(3) . ?
C9 C10 1.419(3) . ?
C9 C11 1.424(3) . ?
C12 C14 1.417(3) . ?
C12 C13 1.422(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Li1 O1 106.74(19) . . ?
O2 Li1 N4 120.5(2) . 2_665 ?
O1 Li1 N4 107.20(18) . 2_665 ?
O2 Li1 N1 104.83(19) . 2_656 ?
O1 Li1 N1 104.08(17) . 2_656 ?
N4 Li1 N1 112.22(18) 2_665 2_656 ?
C1 O1 Li1 156.50(19) . . ?
C11 N1 Li1 165.2(2) . 2_656 ?
C14 N4 Li1 165.3(2) . 2_665 ?
O1 C1 C2 122.57(18) . . ?
O1 C1 C8 117.95(16) . . ?
C2 C1 C8 119.47(17) . . ?
C3 C2 C7 120.61(19) . . ?
C3 C2 C1 120.90(18) . . ?
C7 C2 C1 118.5(2) . . ?
C2 C3 C4 119.7(3) . . ?
C5 C4 C3 118.9(3) . . ?
C6 C5 C4 121.2(2) . . ?
C5 C6 C7 120.7(3) . . ?
C6 C7 C2 118.8(3) . . ?
C9 C8 C12 127.49(18) . . ?
C9 C8 C1 116.65(16) . . ?
C12 C8 C1 115.85(17) . . ?
C8 C9 C10 123.96(17) . . ?
C8 C9 C11 120.70(18) . . ?
C10 C9 C11 115.33(18) . . ?
N2 C10 C9 179.1(3) . . ?
N1 C11 C9 178.9(2) . . ?
C8 C12 C14 121.82(17) . . ?
C8 C12 C13 123.98(19) . . ?
C14 C12 C13 114.16(17) . . ?
N3 C13 C12 176.3(3) . . ?
N4 C14 C12 175.5(2) . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_yak387nn
_database_code_depnum_ccdc_archive 'CCDC 1575000'
_audit_update_record             
;
2017-10-30 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 K N4 O2'
_chemical_formula_sum            'C15 H7 K N4 O2'
_chemical_formula_weight         314.35

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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0354(8)
_cell_length_b                   9.7076(10)
_cell_length_c                   18.914(2)
_cell_angle_alpha                87.341(8)
_cell_angle_beta                 78.773(7)
_cell_angle_gamma                89.785(8)
_cell_volume                     1445.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1176
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .26
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .15
_exptl_absorpt_coefficient_mu    3.335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  0.608

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            9897
_diffrn_reflns_av_unetI/netI     0.1813
_diffrn_reflns_av_R_equivalents  0.1283
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.560
_diffrn_reflns_theta_max         66.964
_diffrn_reflns_theta_full        66.964
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4769
_reflns_number_gt                1896
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4769
_refine_ls_number_parameters     408
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1867
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1807
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.888
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.47174(19) 0.62311(15) 0.09804(8) 0.0502(5) Uani 1 1 d . . . . .
K2 K 0.97504(19) -0.14138(15) 0.09771(8) 0.0502(5) Uani 1 1 d . . . . .
O1 O 0.6393(6) -0.1500(5) 0.1727(3) 0.0552(13) Uani 1 1 d . . . . .
N1 N 0.7074(8) 0.1115(6) 0.3422(4) 0.0555(16) Uani 1 1 d . . . . .
N2 N 0.5493(7) 0.4331(7) 0.2047(3) 0.0546(16) Uani 1 1 d . . . . .
N3 N 0.4631(9) 0.3330(7) 0.0560(3) 0.0680(19) Uani 1 1 d . . . . .
N4 N 0.3436(7) -0.1028(6) 0.0681(3) 0.0519(15) Uani 1 1 d . . . . .
C1 C 0.5396(8) -0.0755(6) 0.2112(4) 0.0376(15) Uani 1 1 d . . . . .
C2 C 0.5320(7) 0.0766(6) 0.1881(3) 0.0371(16) Uani 1 1 d . . . . .
C3 C 0.5878(7) 0.1737(7) 0.2297(3) 0.0391(16) Uani 1 1 d . . . . .
C4 C 0.4691(8) 0.0991(6) 0.1243(3) 0.0379(16) Uani 1 1 d . . . . .
C5 C 0.6538(8) 0.1361(7) 0.2916(4) 0.0400(16) Uani 1 1 d . . . . .
C6 C 0.5688(8) 0.3180(8) 0.2160(3) 0.0388(16) Uani 1 1 d . . . . .
C7 C 0.4665(8) 0.2294(8) 0.0875(4) 0.0432(17) Uani 1 1 d . . . . .
C8 C 0.4013(8) -0.0122(7) 0.0931(4) 0.0423(16) Uani 1 1 d . . . . .
C9 C 0.4294(7) -0.1292(6) 0.2779(3) 0.0343(15) Uani 1 1 d . . . . .
C10 C 0.4260(8) -0.2695(7) 0.2958(4) 0.0448(17) Uani 1 1 d . . . . .
H10 H 0.4953 -0.3285 0.2658 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3211(9) -0.3227(7) 0.3577(4) 0.0512(18) Uani 1 1 d . . . . .
H11 H 0.3189 -0.4170 0.3690 0.061 Uiso 1 1 calc R U . A 1
C13 C 0.2191(9) -0.0947(7) 0.3851(4) 0.0495(18) Uani 1 1 d . . . . .
H13 H 0.1504 -0.0364 0.4157 0.059 Uiso 1 1 calc R U . B 1
C14 C 0.3200(8) -0.0426(7) 0.3225(3) 0.0422(16) Uani 1 1 d . . . . .
H14 H 0.3157 0.0508 0.3097 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2205(9) -0.2355(8) 0.4022(4) 0.0518(19) Uani 0.503(3) 1 d D . P C 1
O2 O 0.092(2) -0.268(4) 0.4607(13) 0.063(5) Uani 0.503(3) 1 d D . P C 1
C15 C 0.055(2) -0.2197(17) 0.5185(8) 0.076(3) Uani 0.503(3) 1 d D . P C 1
H15A H 0.1545 -0.1795 0.5307 0.114 Uiso 0.503(3) 1 calc R U P C 1
H15B H 0.0112 -0.2910 0.5540 0.114 Uiso 0.503(3) 1 calc R U P C 1
H15C H -0.0290 -0.1499 0.5172 0.114 Uiso 0.503(3) 1 calc R U P C 1
C121 C 0.2205(9) -0.2355(8) 0.4022(4) 0.0518(19) Uani 0.497(3) 1 d D . P C 2
O21 O 0.147(2) -0.302(4) 0.4680(13) 0.063(5) Uani 0.497(3) 1 d D . P C 2
C151 C 0.078(2) -0.4136(16) 0.4814(9) 0.076(3) Uani 0.497(3) 1 d D . P C 2
H15D H 0.0426 -0.4443 0.4390 0.114 Uiso 0.497(3) 1 calc R U P C 2
H15E H -0.0201 -0.4058 0.5194 0.114 Uiso 0.497(3) 1 calc R U P C 2
H15F H 0.1551 -0.4789 0.4965 0.114 Uiso 0.497(3) 1 calc R U P C 2
O1A O 0.1354(6) 0.6170(4) 0.1759(2) 0.0518(12) Uani 1 1 d . . . . .
O2A O -0.3987(6) 0.6870(5) 0.4666(3) 0.0667(15) Uani 1 1 d . . . . .
N1A N -0.1562(8) 0.5910(7) 0.0692(3) 0.0549(16) Uani 1 1 d . . . . .
N2A N -0.0325(9) 0.1558(7) 0.0566(3) 0.0685(19) Uani 1 1 d . . . . .
N3A N 0.0470(8) 0.0267(6) 0.2061(3) 0.0549(16) Uani 1 1 d . . . . .
N4A N 0.2171(8) 0.3228(6) 0.3407(4) 0.0615(17) Uani 1 1 d . . . . .
C1A C 0.0361(8) 0.5365(6) 0.2148(3) 0.0356(15) Uani 1 1 d . . . . .
C2A C 0.0308(7) 0.3891(6) 0.1897(3) 0.0359(16) Uani 1 1 d . . . . .
C3A C -0.0285(8) 0.3799(6) 0.1252(3) 0.0404(16) Uani 1 1 d . . . . .
C4A C 0.0846(8) 0.2829(6) 0.2302(3) 0.0363(15) Uani 1 1 d . . . . .
C5A C -0.1000(9) 0.4961(8) 0.0938(4) 0.0478(18) Uani 1 1 d . . . . .
C6A C -0.0311(9) 0.2554(8) 0.0881(4) 0.0517(19) Uani 1 1 d . . . . .
C7A C 0.0661(8) 0.1418(7) 0.2164(3) 0.0405(16) Uani 1 1 d . . . . .
C8A C 0.1580(8) 0.3060(7) 0.2914(4) 0.0439(17) Uani 1 1 d . . . . .
C9A C -0.0763(7) 0.5744(6) 0.2803(3) 0.0336(14) Uani 1 1 d . . . . .
C10A C -0.0789(8) 0.7129(7) 0.3005(3) 0.0425(17) Uani 1 1 d . . . . .
H10A H -0.0064 0.7772 0.2723 0.051 Uiso 1 1 calc R U . . .
C11A C -0.1866(8) 0.7535(7) 0.3611(4) 0.0459(17) Uani 1 1 d . . . . .
H11A H -0.1881 0.8455 0.3728 0.055 Uiso 1 1 calc R U . . .
C12A C -0.2925(8) 0.6609(7) 0.4048(3) 0.0428(17) Uani 1 1 d . . . . .
C13A C -0.2947(8) 0.5210(7) 0.3858(4) 0.0477(18) Uani 1 1 d . . . . .
H13A H -0.3668 0.4572 0.4146 0.057 Uiso 1 1 calc R U . . .
C14A C -0.1894(7) 0.4823(6) 0.3247(3) 0.0387(16) Uani 1 1 d . . . . .
H14A H -0.1924 0.3912 0.3119 0.046 Uiso 1 1 calc R U . . .
C15A C -0.4090(13) 0.8269(9) 0.4889(5) 0.097(3) Uani 1 1 d . . . . .
H15G H -0.3013 0.8546 0.4985 0.145 Uiso 1 1 calc R U . . .
H15H H -0.4943 0.8330 0.5319 0.145 Uiso 1 1 calc R U . . .
H15I H -0.4383 0.8864 0.4513 0.145 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O1A 2.814(4) . ?
K1 N2 2.828(7) . ?
K1 N3 2.870(6) 2_665 ?
K1 N4 2.920(6) 1_565 ?
K1 N1A 2.951(6) 1_655 ?
K1 N3 2.967(7) . ?
K1 O1 3.117(5) 1_565 ?
K1 K1 4.453(3) 2_665 ?
K1 K2 4.593(2) 1_465 ?
K1 K2 4.652(2) 1_565 ?
K2 O1 2.792(5) . ?
K2 N3A 2.825(6) 1_655 ?
K2 N2A 2.876(6) 2_655 ?
K2 N1A 2.920(6) 1_645 ?
K2 N4 2.927(6) 1_655 ?
K2 N2A 2.956(7) 1_655 ?
K2 O1A 3.122(5) 1_645 ?
K2 K2 4.455(3) 2_755 ?
K2 K1 4.593(2) 1_645 ?
K2 K1 4.652(2) 1_545 ?
O1 C1 1.230(7) . ?
O1 K1 3.117(5) 1_545 ?
N1 C5 1.140(8) . ?
N2 C6 1.144(8) . ?
N3 C7 1.148(8) . ?
N3 K1 2.870(6) 2_665 ?
N4 C8 1.157(7) . ?
N4 K1 2.920(6) 1_545 ?
N4 K2 2.927(6) 1_455 ?
C1 C9 1.467(8) . ?
C1 C2 1.524(8) . ?
C2 C3 1.385(8) . ?
C2 C4 1.403(9) . ?
C3 C5 1.410(10) . ?
C3 C6 1.425(10) . ?
C4 C8 1.415(9) . ?
C4 C7 1.418(10) . ?
C9 C10 1.387(8) . ?
C9 C14 1.401(8) . ?
C10 C11 1.382(9) . ?
C10 H10 0.9300 . ?
C11 C121 1.369(10) . ?
C11 C12 1.369(10) . ?
C11 H11 0.9300 . ?
C13 C14 1.375(9) . ?
C13 C121 1.390(9) . ?
C13 C12 1.390(9) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C12 O2 1.383(13) . ?
O2 C15 1.19(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C121 O21 1.399(12) . ?
O21 C151 1.22(4) . ?
C151 H15D 0.9600 . ?
C151 H15E 0.9600 . ?
C151 H15F 0.9600 . ?
O1A C1A 1.229(7) . ?
O1A K2 3.122(5) 1_465 ?
O2A C12A 1.339(7) . ?
O2A C15A 1.438(9) . ?
N1A C5A 1.144(9) . ?
N1A K2 2.920(6) 1_465 ?
N1A K1 2.951(6) 1_455 ?
N2A C6A 1.160(8) . ?
N2A K2 2.876(6) 2_655 ?
N2A K2 2.956(7) 1_455 ?
N3A C7A 1.159(7) . ?
N3A K2 2.825(6) 1_455 ?
N4A C8A 1.145(8) . ?
C1A C9A 1.444(8) . ?
C1A C2A 1.532(8) . ?
C2A C4A 1.374(9) . ?
C2A C3A 1.401(9) . ?
C3A C5A 1.421(11) . ?
C3A C6A 1.427(10) . ?
C4A C7A 1.420(9) . ?
C4A C8A 1.425(10) . ?
C9A C14A 1.404(8) . ?
C9A C10A 1.414(8) . ?
C10A C11A 1.367(9) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.371(9) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.422(9) . ?
C13A C14A 1.360(8) . ?
C13A H13A 0.9300 . ?
C14A H14A 0.9300 . ?
C15A H15G 0.9600 . ?
C15A H15H 0.9600 . ?
C15A H15I 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A K1 N2 87.11(16) . . ?
O1A K1 N3 119.81(18) . 2_665 ?
N2 K1 N3 139.8(2) . 2_665 ?
O1A K1 N4 76.27(15) . 1_565 ?
N2 K1 N4 146.09(18) . 1_565 ?
N3 K1 N4 73.33(18) 2_665 1_565 ?
O1A K1 N1A 158.74(17) . 1_655 ?
N2 K1 N1A 73.00(18) . 1_655 ?
N3 K1 N1A 81.12(19) 2_665 1_655 ?
N4 K1 N1A 116.52(17) 1_565 1_655 ?
O1A K1 N3 93.98(16) . . ?
N2 K1 N3 67.42(18) . . ?
N3 K1 N3 80.6(2) 2_665 . ?
N4 K1 N3 141.93(19) 1_565 . ?
N1A K1 N3 85.40(18) 1_655 . ?
O1A K1 O1 102.67(12) . 1_565 ?
N2 K1 O1 87.35(15) . 1_565 ?
N3 K1 O1 112.02(16) 2_665 1_565 ?
N4 K1 O1 68.29(15) 1_565 1_565 ?
N1A K1 O1 69.68(15) 1_655 1_565 ?
N3 K1 O1 149.06(17) . 1_565 ?
O1A K1 K1 111.51(10) . 2_665 ?
N2 K1 K1 103.68(14) . 2_665 ?
N3 K1 K1 41.08(13) 2_665 2_665 ?
N4 K1 K1 109.86(13) 1_565 2_665 ?
N1A K1 K1 81.21(12) 1_655 2_665 ?
N3 K1 K1 39.47(13) . 2_665 ?
O1 K1 K1 144.39(10) 1_565 2_665 ?
O1A K1 K2 41.81(10) . 1_465 ?
N2 K1 K2 128.22(13) . 1_465 ?
N3 K1 K2 86.28(15) 2_665 1_465 ?
N4 K1 K2 38.29(11) 1_565 1_465 ?
N1A K1 K2 154.66(14) 1_655 1_465 ?
N3 K1 K2 114.18(14) . 1_465 ?
O1 K1 K2 95.29(9) 1_565 1_465 ?
K1 K1 K2 103.36(5) 2_665 1_465 ?
O1A K1 K2 138.33(10) . 1_565 ?
N2 K1 K2 89.70(12) . 1_565 ?
N3 K1 K2 87.78(14) 2_665 1_565 ?
N4 K1 K2 83.87(12) 1_565 1_565 ?
N1A K1 K2 37.36(12) 1_655 1_565 ?
N3 K1 K2 122.76(14) . 1_565 ?
O1 K1 K2 35.67(9) 1_565 1_565 ?
K1 K1 K2 109.60(5) 2_665 1_565 ?
K2 K1 K2 120.72(5) 1_465 1_565 ?
O1 K2 N3A 87.26(16) . 1_655 ?
O1 K2 N2A 117.53(18) . 2_655 ?
N3A K2 N2A 141.11(18) 1_655 2_655 ?
O1 K2 N1A 74.75(15) . 1_645 ?
N3A K2 N1A 144.79(19) 1_655 1_645 ?
N2A K2 N1A 73.71(18) 2_655 1_645 ?
O1 K2 N4 160.00(16) . 1_655 ?
N3A K2 N4 73.79(17) 1_655 1_655 ?
N2A K2 N4 82.02(18) 2_655 1_655 ?
N1A K2 N4 117.61(17) 1_645 1_655 ?
O1 K2 N2A 94.33(17) . 1_655 ?
N3A K2 N2A 67.54(18) 1_655 1_655 ?
N2A K2 N2A 80.4(2) 2_655 1_655 ?
N1A K2 N2A 142.4(2) 1_645 1_655 ?
N4 K2 N2A 84.45(18) 1_655 1_655 ?
O1 K2 O1A 101.51(13) . 1_645 ?
N3A K2 O1A 86.61(16) 1_655 1_645 ?
N2A K2 O1A 114.27(16) 2_655 1_645 ?
N1A K2 O1A 68.27(16) 1_645 1_645 ?
N4 K2 O1A 71.60(14) 1_655 1_645 ?
N2A K2 O1A 148.98(16) 1_655 1_645 ?
O1 K2 K2 110.39(12) . 2_755 ?
N3A K2 K2 104.41(14) 1_655 2_755 ?
N2A K2 K2 40.86(13) 2_655 2_755 ?
N1A K2 K2 110.14(14) 1_645 2_755 ?
N4 K2 K2 81.16(12) 1_655 2_755 ?
N2A K2 K2 39.52(12) 1_655 2_755 ?
O1A K2 K2 146.51(10) 1_645 2_755 ?
O1 K2 K1 138.44(11) . 1_645 ?
N3A K2 K1 90.06(13) 1_655 1_645 ?
N2A K2 K1 89.21(15) 2_655 1_645 ?
N1A K2 K1 84.29(13) 1_645 1_645 ?
N4 K2 K1 38.17(12) 1_655 1_645 ?
N2A K2 K1 122.62(14) 1_655 1_645 ?
O1A K2 K1 36.94(8) 1_645 1_645 ?
K2 K2 K1 110.42(5) 2_755 1_645 ?
O1 K2 K1 40.60(10) . 1_545 ?
N3A K2 K1 127.05(13) 1_655 1_545 ?
N2A K2 K1 85.54(14) 2_655 1_545 ?
N1A K2 K1 37.83(13) 1_645 1_545 ?
N4 K2 K1 155.23(12) 1_655 1_545 ?
N2A K2 K1 114.50(14) 1_655 1_545 ?
O1A K2 K1 94.48(8) 1_645 1_545 ?
K2 K2 K1 103.00(5) 2_755 1_545 ?
K1 K2 K1 120.72(5) 1_645 1_545 ?
C1 O1 K2 138.4(4) . . ?
C1 O1 K1 115.2(4) . 1_545 ?
K2 O1 K1 103.73(15) . 1_545 ?
C6 N2 K1 142.0(5) . . ?
C7 N3 K1 126.5(5) . 2_665 ?
C7 N3 K1 132.5(5) . . ?
K1 N3 K1 99.4(2) 2_665 . ?
C8 N4 K1 116.1(5) . 1_545 ?
C8 N4 K2 119.3(5) . 1_455 ?
K1 N4 K2 103.54(18) 1_545 1_455 ?
O1 C1 C9 121.8(6) . . ?
O1 C1 C2 118.3(5) . . ?
C9 C1 C2 119.9(5) . . ?
C3 C2 C4 128.0(6) . . ?
C3 C2 C1 118.6(6) . . ?
C4 C2 C1 113.4(5) . . ?
C2 C3 C5 122.1(6) . . ?
C2 C3 C6 121.9(6) . . ?
C5 C3 C6 115.8(5) . . ?
C2 C4 C8 120.0(6) . . ?
C2 C4 C7 124.3(5) . . ?
C8 C4 C7 115.7(6) . . ?
N1 C5 C3 177.1(7) . . ?
N2 C6 C3 178.2(7) . . ?
N3 C7 C4 177.9(7) . . ?
N4 C8 C4 179.0(7) . . ?
C10 C9 C14 118.7(6) . . ?
C10 C9 C1 119.9(6) . . ?
C14 C9 C1 121.3(6) . . ?
C11 C10 C9 120.9(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C121 C11 C10 119.5(7) . . ?
C12 C11 C10 119.5(7) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C14 C13 C121 119.4(7) . . ?
C14 C13 C12 119.4(7) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 120.4(6) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C11 C12 O2 128.7(17) . . ?
C11 C12 C13 121.0(6) . . ?
O2 C12 C13 109.6(16) . . ?
C15 O2 C12 131(3) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C121 C13 121.0(6) . . ?
C11 C121 O21 111.8(16) . . ?
C13 C121 O21 126.5(17) . . ?
C151 O21 C121 131(3) . . ?
O21 C151 H15D 109.5 . . ?
O21 C151 H15E 109.5 . . ?
H15D C151 H15E 109.5 . . ?
O21 C151 H15F 109.5 . . ?
H15D C151 H15F 109.5 . . ?
H15E C151 H15F 109.5 . . ?
C1A O1A K1 139.3(4) . . ?
C1A O1A K2 116.6(4) . 1_465 ?
K1 O1A K2 101.25(13) . 1_465 ?
C12A O2A C15A 117.6(6) . . ?
C5A N1A K2 116.5(5) . 1_465 ?
C5A N1A K1 118.5(5) . 1_455 ?
K2 N1A K1 104.8(2) 1_465 1_455 ?
C6A N2A K2 125.8(6) . 2_655 ?
C6A N2A K2 133.6(6) . 1_455 ?
K2 N2A K2 99.6(2) 2_655 1_455 ?
C7A N3A K2 140.3(5) . 1_455 ?
O1A C1A C9A 123.9(5) . . ?
O1A C1A C2A 116.6(5) . . ?
C9A C1A C2A 119.5(5) . . ?
C4A C2A C3A 127.3(5) . . ?
C4A C2A C1A 118.8(6) . . ?
C3A C2A C1A 113.9(6) . . ?
C2A C3A C5A 121.0(6) . . ?
C2A C3A C6A 124.0(6) . . ?
C5A C3A C6A 114.9(6) . . ?
C2A C4A C7A 123.1(6) . . ?
C2A C4A C8A 122.3(5) . . ?
C7A C4A C8A 114.5(6) . . ?
N1A C5A C3A 178.9(8) . . ?
N2A C6A C3A 178.6(8) . . ?
N3A C7A C4A 178.4(7) . . ?
N4A C8A C4A 179.1(7) . . ?
C14A C9A C10A 116.9(6) . . ?
C14A C9A C1A 123.9(5) . . ?
C10A C9A C1A 119.2(5) . . ?
C11A C10A C9A 120.9(6) . . ?
C11A C10A H10A 119.6 . . ?
C9A C10A H10A 119.6 . . ?
C10A C11A C12A 121.2(6) . . ?
C10A C11A H11A 119.4 . . ?
C12A C11A H11A 119.4 . . ?
O2A C12A C11A 126.7(6) . . ?
O2A C12A C13A 113.8(6) . . ?
C11A C12A C13A 119.5(6) . . ?
C14A C13A C12A 118.8(6) . . ?
C14A C13A H13A 120.6 . . ?
C12A C13A H13A 120.6 . . ?
C13A C14A C9A 122.7(6) . . ?
C13A C14A H14A 118.7 . . ?
C9A C14A H14A 118.7 . . ?
O2A C15A H15G 109.5 . . ?
O2A C15A H15H 109.5 . . ?
H15G C15A H15H 109.5 . . ?
O2A C15A H15I 109.5 . . ?
H15G C15A H15I 109.5 . . ?
H15H C15A H15I 109.5 . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_yak413
_database_code_depnum_ccdc_archive 'CCDC 1575038'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H7 Cs N4 O'
_chemical_formula_sum            'C15 H7 Cs N4 O'
_chemical_formula_weight         392.16

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'
Cs Cs -0.7457 7.9052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   16.2580(10)
_cell_length_b                   10.1991(5)
_cell_length_c                   9.0735(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.221(6)
_cell_angle_gamma                90
_cell_volume                     1485.10(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1530
_cell_measurement_theta_min      4
_cell_measurement_theta_max      50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .21
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    19.487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            9457
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.138
_diffrn_reflns_theta_max         72.057
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2793
_reflns_number_gt                2037
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1215P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2793
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.1725
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs 0.91796(3) 0.12986(5) 0.14911(5) 0.0727(2) Uani 1 1 d . . . . .
O1 O 0.8202(4) 0.4034(6) 0.3330(8) 0.0862(17) Uani 1 1 d . . . . .
N1 N 0.9178(5) 0.4096(8) 0.0049(10) 0.084(2) Uani 1 1 d . . . . .
N2 N 0.9350(5) 0.8253(8) 0.0668(11) 0.090(2) Uani 1 1 d . . . . .
N3 N 0.7771(5) 0.9430(8) 0.2314(11) 0.090(2) Uani 1 1 d . . . . .
N4 N 0.6374(6) 0.6423(9) 0.4128(13) 0.108(3) Uani 1 1 d . . . . .
C1 C 0.7748(5) 0.4578(8) 0.2326(8) 0.0633(17) Uani 1 1 d . . . . .
C2 C 0.7064(4) 0.3913(7) 0.1379(8) 0.0592(15) Uani 1 1 d . . . . .
C3 C 0.6958(5) 0.2573(8) 0.1566(9) 0.0668(18) Uani 1 1 d . . . . .
H3 H 0.7301 0.2130 0.2325 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6350(5) 0.1898(9) 0.0633(10) 0.074(2) Uani 1 1 d . . . . .
H4 H 0.6295 0.0999 0.0762 0.088 Uiso 1 1 calc R U . . .
C5 C 0.5812(5) 0.2538(9) -0.0508(9) 0.072(2) Uani 1 1 d . . . . .
C6 C 0.5902(5) 0.3883(10) -0.0630(11) 0.078(2) Uani 1 1 d . . . . .
H6 H 0.5533 0.4340 -0.1337 0.094 Uiso 1 1 calc R U . . .
C7 C 0.6523(5) 0.4562(8) 0.0266(9) 0.0679(18) Uani 1 1 d . . . . .
H7 H 0.6582 0.5458 0.0128 0.081 Uiso 1 1 calc R U . . .
C8 C 0.7951(4) 0.5996(7) 0.2004(9) 0.0606(16) Uani 1 1 d . . . . .
C9 C 0.8602(4) 0.6147(7) 0.1184(9) 0.0640(16) Uani 1 1 d . . . . .
C10 C 0.8923(5) 0.5002(8) 0.0557(10) 0.0714(19) Uani 1 1 d . . . . .
C11 C 0.8996(5) 0.7344(8) 0.0900(9) 0.0656(17) Uani 1 1 d . . . . .
C12 C 0.7516(4) 0.6963(8) 0.2612(9) 0.0631(16) Uani 1 1 d . . . . .
C13 C 0.7666(5) 0.8338(9) 0.2420(9) 0.0682(18) Uani 1 1 d . . . . .
C14 C 0.6886(6) 0.6655(9) 0.3455(10) 0.076(2) Uani 1 1 d . . . . .
C15 C 0.5162(6) 0.1796(12) -0.1498(11) 0.091(3) Uani 1 1 d . . . . .
H15A H 0.4624 0.2160 -0.1432 0.137 Uiso 1 1 calc R U . . .
H15B H 0.5176 0.0894 -0.1193 0.137 Uiso 1 1 calc R U . . .
H15C H 0.5263 0.1853 -0.2509 0.137 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cs1 O1 3.067(6) 4_565 ?
Cs1 N1 3.138(8) . ?
Cs1 N3 3.160(8) 1_545 ?
Cs1 N2 3.217(8) 1_545 ?
Cs1 N1 3.253(9) 4_566 ?
Cs1 N2 3.355(7) 3_765 ?
Cs1 C11 3.644(8) 2_745 ?
Cs1 O1 3.734(7) . ?
Cs1 N2 3.789(9) 2_745 ?
Cs1 C3 3.849(7) . ?
Cs1 C9 3.879(7) 2_745 ?
Cs1 C10 3.879(9) . ?
O1 C1 1.212(9) . ?
O1 Cs1 3.067(6) 4_566 ?
N1 C10 1.141(11) . ?
N1 Cs1 3.253(9) 4_565 ?
N2 C11 1.129(11) . ?
N2 Cs1 3.217(8) 1_565 ?
N2 Cs1 3.356(7) 3_765 ?
N2 Cs1 3.789(9) 2_755 ?
N3 C13 1.134(12) . ?
N3 Cs1 3.160(8) 1_565 ?
N4 C14 1.133(12) . ?
C1 C2 1.459(11) . ?
C1 C8 1.523(11) . ?
C2 C3 1.392(10) . ?
C2 C7 1.395(11) . ?
C3 C4 1.378(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(12) . ?
C5 C15 1.481(12) . ?
C6 C7 1.377(13) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C12 1.379(11) . ?
C8 C9 1.396(11) . ?
C9 C11 1.421(11) . ?
C9 C10 1.434(11) . ?
C9 Cs1 3.879(7) 2_755 ?
C11 Cs1 3.644(8) 2_755 ?
C12 C14 1.409(11) . ?
C12 C13 1.438(12) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cs1 N1 75.2(2) 4_565 . ?
O1 Cs1 N3 82.4(2) 4_565 1_545 ?
N1 Cs1 N3 134.0(2) . 1_545 ?
O1 Cs1 N2 74.2(2) 4_565 1_545 ?
N1 Cs1 N2 140.8(2) . 1_545 ?
N3 Cs1 N2 64.23(19) 1_545 1_545 ?
O1 Cs1 N1 146.3(2) 4_565 4_566 ?
N1 Cs1 N1 121.74(18) . 4_566 ?
N3 Cs1 N1 64.9(2) 1_545 4_566 ?
N2 Cs1 N1 97.2(2) 1_545 4_566 ?
O1 Cs1 N2 77.3(2) 4_565 3_765 ?
N1 Cs1 N2 65.52(19) . 3_765 ?
N3 Cs1 N2 146.2(2) 1_545 3_765 ?
N2 Cs1 N2 84.3(2) 1_545 3_765 ?
N1 Cs1 N2 135.2(2) 4_566 3_765 ?
O1 Cs1 C11 152.30(19) 4_565 2_745 ?
N1 Cs1 C11 87.2(2) . 2_745 ?
N3 Cs1 C11 124.6(2) 1_545 2_745 ?
N2 Cs1 C11 110.0(2) 1_545 2_745 ?
N1 Cs1 C11 61.42(18) 4_566 2_745 ?
N2 Cs1 C11 76.0(2) 3_765 2_745 ?
O1 Cs1 O1 107.86(15) 4_565 . ?
N1 Cs1 O1 62.31(17) . . ?
N3 Cs1 O1 88.20(18) 1_545 . ?
N2 Cs1 O1 152.11(16) 1_545 . ?
N1 Cs1 O1 65.22(18) 4_566 . ?
N2 Cs1 O1 123.57(18) 3_765 . ?
C11 Cs1 O1 81.46(16) 2_745 . ?
O1 Cs1 N2 150.48(19) 4_565 2_745 ?
N1 Cs1 N2 76.3(2) . 2_745 ?
N3 Cs1 N2 124.0(2) 1_545 2_745 ?
N2 Cs1 N2 126.68(15) 1_545 2_745 ?
N1 Cs1 N2 59.37(18) 4_566 2_745 ?
N2 Cs1 N2 83.96(15) 3_765 2_745 ?
C11 Cs1 N2 17.33(16) 2_745 2_745 ?
O1 Cs1 N2 64.54(14) . 2_745 ?
O1 Cs1 C3 72.96(17) 4_565 . ?
N1 Cs1 C3 76.26(18) . . ?
N3 Cs1 C3 58.78(19) 1_545 . ?
N2 Cs1 C3 116.50(18) 1_545 . ?
N1 Cs1 C3 82.78(19) 4_566 . ?
N2 Cs1 C3 136.2(2) 3_765 . ?
C11 Cs1 C3 123.91(18) 2_745 . ?
O1 Cs1 C3 43.29(15) . . ?
N2 Cs1 C3 107.56(16) 2_745 . ?
O1 Cs1 C9 143.27(17) 4_565 2_745 ?
N1 Cs1 C9 101.6(2) . 2_745 ?
N3 Cs1 C9 119.6(2) 1_545 2_745 ?
N2 Cs1 C9 88.89(19) 1_545 2_745 ?
N1 Cs1 C9 66.66(19) 4_566 2_745 ?
N2 Cs1 C9 68.6(2) 3_765 2_745 ?
C11 Cs1 C9 21.48(16) 2_745 2_745 ?
O1 Cs1 C9 102.23(15) . 2_745 ?
N2 Cs1 C9 38.80(16) 2_745 2_745 ?
C3 Cs1 C9 142.86(17) . 2_745 ?
O1 Cs1 C10 83.21(18) 4_565 . ?
N1 Cs1 C10 14.28(18) . . ?
N3 Cs1 C10 125.61(19) 1_545 . ?
N2 Cs1 C10 154.1(2) 1_545 . ?
N1 Cs1 C10 108.67(19) 4_566 . ?
N2 Cs1 C10 78.54(19) 3_765 . ?
C11 Cs1 C10 84.55(18) 2_745 . ?
O1 Cs1 C10 48.05(16) . . ?
N2 Cs1 C10 70.76(18) 2_745 . ?
C3 Cs1 C10 66.84(16) . . ?
C9 Cs1 C10 102.46(17) 2_745 . ?
C1 O1 Cs1 156.3(6) . 4_566 ?
C1 O1 Cs1 105.0(5) . . ?
Cs1 O1 Cs1 98.14(16) 4_566 . ?
C10 N1 Cs1 123.0(6) . . ?
C10 N1 Cs1 124.0(7) . 4_565 ?
Cs1 N1 Cs1 107.5(2) . 4_565 ?
C11 N2 Cs1 133.2(6) . 1_565 ?
C11 N2 Cs1 130.8(6) . 3_765 ?
Cs1 N2 Cs1 95.7(2) 1_565 3_765 ?
C11 N2 Cs1 74.1(6) . 2_755 ?
Cs1 N2 Cs1 114.7(3) 1_565 2_755 ?
Cs1 N2 Cs1 92.20(17) 3_765 2_755 ?
C13 N3 Cs1 137.5(6) . 1_565 ?
O1 C1 C2 123.1(7) . . ?
O1 C1 C8 117.0(7) . . ?
C2 C1 C8 119.8(6) . . ?
C3 C2 C7 118.6(7) . . ?
C3 C2 C1 118.8(7) . . ?
C7 C2 C1 122.6(7) . . ?
C4 C3 C2 120.4(8) . . ?
C4 C3 Cs1 113.8(5) . . ?
C2 C3 Cs1 101.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
Cs1 C3 H3 53.0 . . ?
C3 C4 C5 121.4(8) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.3(8) . . ?
C6 C5 C15 122.1(9) . . ?
C4 C5 C15 120.6(9) . . ?
C7 C6 C5 121.8(8) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C2 120.4(8) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C12 C8 C9 128.0(7) . . ?
C12 C8 C1 117.5(6) . . ?
C9 C8 C1 114.4(6) . . ?
C8 C9 C11 126.4(7) . . ?
C8 C9 C10 118.5(7) . . ?
C11 C9 C10 115.1(7) . . ?
C8 C9 Cs1 115.6(5) . 2_755 ?
C11 C9 Cs1 69.9(4) . 2_755 ?
C10 C9 Cs1 83.2(4) . 2_755 ?
N1 C10 C9 179.5(9) . . ?
N1 C10 Cs1 42.7(5) . . ?
C9 C10 Cs1 137.7(5) . . ?
N2 C11 C9 176.0(8) . . ?
N2 C11 Cs1 88.6(6) . 2_755 ?
C9 C11 Cs1 88.6(4) . 2_755 ?
C8 C12 C14 121.4(7) . . ?
C8 C12 C13 122.7(7) . . ?
C14 C12 C13 115.8(7) . . ?
N3 C13 C12 177.5(9) . . ?
N4 C14 C12 179.1(10) . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cs1 O1 C1 C2 -133.5(11) 4_566 . . . ?
Cs1 O1 C1 C2 59.4(8) . . . . ?
Cs1 O1 C1 C8 50.5(17) 4_566 . . . ?
Cs1 O1 C1 C8 -116.6(6) . . . . ?
O1 C1 C2 C3 -4.4(11) . . . . ?
C8 C1 C2 C3 171.5(6) . . . . ?
O1 C1 C2 C7 177.3(8) . . . . ?
C8 C1 C2 C7 -6.7(10) . . . . ?
C7 C2 C3 C4 2.2(11) . . . . ?
C1 C2 C3 C4 -176.1(7) . . . . ?
C7 C2 C3 Cs1 128.7(6) . . . . ?
C1 C2 C3 Cs1 -49.7(7) . . . . ?
C2 C3 C4 C5 -1.1(11) . . . . ?
Cs1 C3 C4 C5 -121.6(7) . . . . ?
C3 C4 C5 C6 -1.9(12) . . . . ?
C3 C4 C5 C15 -179.9(8) . . . . ?
C4 C5 C6 C7 3.8(13) . . . . ?
C15 C5 C6 C7 -178.1(8) . . . . ?
C5 C6 C7 C2 -2.8(13) . . . . ?
C3 C2 C7 C6 -0.3(11) . . . . ?
C1 C2 C7 C6 178.0(7) . . . . ?
O1 C1 C8 C12 -97.8(9) . . . . ?
C2 C1 C8 C12 86.0(9) . . . . ?
O1 C1 C8 C9 78.7(9) . . . . ?
C2 C1 C8 C9 -97.5(8) . . . . ?
C12 C8 C9 C11 5.2(13) . . . . ?
C1 C8 C9 C11 -170.8(7) . . . . ?
C12 C8 C9 C10 -175.2(8) . . . . ?
C1 C8 C9 C10 8.8(10) . . . . ?
C12 C8 C9 Cs1 88.4(8) . . . 2_755 ?
C1 C8 C9 Cs1 -87.6(6) . . . 2_755 ?
Cs1 N1 C10 Cs1 150.6(11) 4_565 . . . ?
C8 C9 C10 Cs1 -30.0(11) . . . . ?
C11 C9 C10 Cs1 149.7(6) . . . . ?
Cs1 C9 C10 Cs1 85.6(7) 2_755 . . . ?
Cs1 N2 C11 Cs1 -109.2(8) 1_565 . . 2_755 ?
Cs1 N2 C11 Cs1 78.8(7) 3_765 . . 2_755 ?
C8 C9 C11 Cs1 107.6(8) . . . 2_755 ?
C10 C9 C11 Cs1 -72.0(7) . . . 2_755 ?
C9 C8 C12 C14 -178.1(8) . . . . ?
C1 C8 C12 C14 -2.2(11) . . . . ?
C9 C8 C12 C13 2.5(13) . . . . ?
C1 C8 C12 C13 178.4(7) . . . . ?

_refine_diff_density_max         2.237
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.197

####################################################################### 
# 
# 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_yak411
_database_code_depnum_ccdc_archive 'CCDC 1575037'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H4 Br Cs N4 O'
_chemical_formula_sum            'C14 H4 Br Cs N4 O'
_chemical_formula_weight         457.03

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.7457 7.9052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.4897(2)
_cell_length_b                   18.0253(7)
_cell_length_c                   15.6406(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.225(3)
_cell_angle_gamma                90
_cell_volume                     1543.49(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    896
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .10
_exptl_crystal_size_min          .06
_exptl_absorpt_coefficient_mu    21.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            11059
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.1224
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.748
_diffrn_reflns_theta_max         72.275
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3005
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1875P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3005
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0862
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.2244
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cs1 Cs 0.16299(11) 0.38354(3) 1.10349(4) 0.0757(3) Uani 1 1 d . . . . .
Br1 Br 0.7372(3) 0.06152(6) 0.87558(6) 0.0905(4) Uani 1 1 d . . . . .
O1 O 0.1612(13) 0.2131(4) 1.2057(4) 0.0826(17) Uani 1 1 d . . . . .
N1 N 0.990(2) 0.2178(6) 1.4368(7) 0.102(3) Uani 1 1 d . . . . .
N2 N 0.6956(17) 0.3234(5) 1.1935(6) 0.081(2) Uani 1 1 d . . . . .
N3 N 0.0735(18) 0.0229(5) 1.2972(6) 0.087(2) Uani 1 1 d . . . . .
N4 N 0.676(2) 0.0667(6) 1.4808(7) 0.097(3) Uani 1 1 d . . . . .
C1 C 0.3427(14) 0.1765(5) 1.2056(5) 0.0604(16) Uani 1 1 d . . . . .
C2 C 0.4399(16) 0.1461(4) 1.1276(5) 0.0607(16) Uani 1 1 d . . . . .
C3 C 0.6522(19) 0.1035(5) 1.1301(6) 0.0685(19) Uani 1 1 d . . . . .
H3 H 0.7349 0.0924 1.1825 0.082 Uiso 1 1 calc R U . . .
C4 C 0.7408(19) 0.0777(5) 1.0551(6) 0.072(2) Uani 1 1 d . . . . .
H4 H 0.8829 0.0495 1.0567 0.087 Uiso 1 1 calc R U . . .
C5 C 0.6151(19) 0.0945(5) 0.9781(5) 0.072(2) Uani 1 1 d . . . . .
C6 C 0.405(2) 0.1351(6) 0.9746(6) 0.076(2) Uani 1 1 d . . . . .
H6 H 0.3220 0.1452 0.9219 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3118(17) 0.1617(5) 1.0500(6) 0.071(2) Uani 1 1 d . . . . .
H7 H 0.1680 0.1891 1.0479 0.086 Uiso 1 1 calc R U . . .
C8 C 0.4986(14) 0.1657(4) 1.2900(5) 0.0580(15) Uani 1 1 d . . . . .
C9 C 0.6798(16) 0.2201(5) 1.3052(5) 0.0629(17) Uani 1 1 d . . . . .
C10 C 0.845(2) 0.2198(5) 1.3783(6) 0.076(2) Uani 1 1 d . . . . .
C11 C 0.6947(17) 0.2775(5) 1.2460(6) 0.0664(18) Uani 1 1 d . . . . .
C12 C 0.4419(16) 0.1061(4) 1.3405(5) 0.0618(17) Uani 1 1 d . . . . .
C13 C 0.2415(17) 0.0591(5) 1.3158(5) 0.0656(19) Uani 1 1 d . . . . .
C14 C 0.5780(19) 0.0846(5) 1.4179(6) 0.071(2) 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
Cs1 N2 3.205(9) 1_455 ?
Cs1 N1 3.267(10) 4_465 ?
Cs1 N3 3.272(8) 2_557 ?
Cs1 N4 3.298(11) 4_465 ?
Cs1 N2 3.332(9) . ?
Cs1 O1 3.463(8) . ?
Cs1 N4 3.635(13) 4_565 ?
Cs1 N4 3.687(12) 2_657 ?
Cs1 C14 3.863(9) 4_565 ?
Cs1 C14 3.916(10) 2_657 ?
Cs1 Cs1 5.4897(2) 1_655 ?
Cs1 Cs1 5.4897(2) 1_455 ?
Br1 C5 1.879(9) . ?
O1 C1 1.196(10) . ?
N1 C10 1.168(14) . ?
N1 Cs1 3.267(10) 4_666 ?
N2 C11 1.165(13) . ?
N2 Cs1 3.205(9) 1_655 ?
N3 C13 1.150(13) . ?
N3 Cs1 3.272(8) 2_547 ?
N4 C14 1.133(14) . ?
N4 Cs1 3.298(11) 4_666 ?
N4 Cs1 3.635(13) 4_566 ?
N4 Cs1 3.687(12) 2_647 ?
C1 C2 1.472(11) . ?
C1 C8 1.532(11) . ?
C2 C7 1.387(12) . ?
C2 C3 1.393(14) . ?
C3 C4 1.382(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(16) . ?
C6 C7 1.402(14) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C12 1.382(11) . ?
C8 C9 1.404(12) . ?
C9 C11 1.395(12) . ?
C9 C10 1.407(14) . ?
C12 C13 1.419(13) . ?
C12 C14 1.429(13) . ?
C14 Cs1 3.863(9) 4_566 ?
C14 Cs1 3.916(10) 2_647 ?

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
N2 Cs1 N1 88.1(3) 1_455 4_465 ?
N2 Cs1 N3 72.1(3) 1_455 2_557 ?
N1 Cs1 N3 134.9(2) 4_465 2_557 ?
N2 Cs1 N4 73.0(3) 1_455 4_465 ?
N1 Cs1 N4 60.8(2) 4_465 4_465 ?
N3 Cs1 N4 74.6(2) 2_557 4_465 ?
N2 Cs1 N2 114.2(3) 1_455 . ?
N1 Cs1 N2 110.5(2) 4_465 . ?
N3 Cs1 N2 114.6(2) 2_557 . ?
N4 Cs1 N2 169.4(2) 4_465 . ?
N2 Cs1 O1 57.83(19) 1_455 . ?
N1 Cs1 O1 82.1(2) 4_465 . ?
N3 Cs1 O1 116.6(2) 2_557 . ?
N4 Cs1 O1 118.7(2) 4_465 . ?
N2 Cs1 O1 63.17(19) . . ?
N2 Cs1 N4 172.6(2) 1_455 4_565 ?
N1 Cs1 N4 84.7(3) 4_465 4_565 ?
N3 Cs1 N4 114.3(3) 2_557 4_565 ?
N4 Cs1 N4 104.6(3) 4_465 4_565 ?
N2 Cs1 N4 67.3(2) . 4_565 ?
O1 Cs1 N4 119.41(19) . 4_565 ?
N2 Cs1 N4 132.9(2) 1_455 2_657 ?
N1 Cs1 N4 106.2(3) 4_465 2_657 ?
N3 Cs1 N4 66.2(2) 2_557 2_657 ?
N4 Cs1 N4 75.8(3) 4_465 2_657 ?
N2 Cs1 N4 102.5(2) . 2_657 ?
O1 Cs1 N4 165.5(2) . 2_657 ?
N4 Cs1 N4 51.3(3) 4_565 2_657 ?
N2 Cs1 C14 156.3(2) 1_455 4_565 ?
N1 Cs1 C14 68.6(3) 4_465 4_565 ?
N3 Cs1 C14 121.3(2) 2_557 4_565 ?
N4 Cs1 C14 91.1(3) 4_465 4_565 ?
N2 Cs1 C14 79.5(2) . 4_565 ?
O1 Cs1 C14 120.04(17) . 4_565 ?
N4 Cs1 C14 17.0(2) 4_565 4_565 ?
N4 Cs1 C14 55.1(2) 2_657 4_565 ?
N2 Cs1 C14 131.1(2) 1_455 2_657 ?
N1 Cs1 C14 122.4(3) 4_465 2_657 ?
N3 Cs1 C14 59.3(2) 2_557 2_657 ?
N4 Cs1 C14 89.0(3) 4_465 2_657 ?
N2 Cs1 C14 91.4(2) . 2_657 ?
O1 Cs1 C14 150.89(19) . 2_657 ?
N4 Cs1 C14 55.0(2) 4_565 2_657 ?
N4 Cs1 C14 16.8(2) 2_657 2_657 ?
C14 Cs1 C14 63.9(2) 4_565 2_657 ?
N2 Cs1 Cs1 146.39(16) 1_455 1_655 ?
N1 Cs1 Cs1 103.4(2) 4_465 1_655 ?
N3 Cs1 Cs1 115.57(19) 2_557 1_655 ?
N4 Cs1 Cs1 140.1(2) 4_465 1_655 ?
N2 Cs1 Cs1 32.18(15) . 1_655 ?
O1 Cs1 Cs1 92.12(12) . 1_655 ?
N4 Cs1 Cs1 35.55(16) 4_565 1_655 ?
N4 Cs1 Cs1 74.57(18) 2_657 1_655 ?
C14 Cs1 Cs1 49.82(15) 4_565 1_655 ?
C14 Cs1 Cs1 68.33(14) 2_657 1_655 ?
N2 Cs1 Cs1 33.61(16) 1_455 1_455 ?
N1 Cs1 Cs1 76.6(2) 4_465 1_455 ?
N3 Cs1 Cs1 64.43(19) 2_557 1_455 ?
N4 Cs1 Cs1 39.9(2) 4_465 1_455 ?
N2 Cs1 Cs1 147.82(15) . 1_455 ?
O1 Cs1 Cs1 87.89(12) . 1_455 ?
N4 Cs1 Cs1 144.45(16) 4_565 1_455 ?
N4 Cs1 Cs1 105.43(18) 2_657 1_455 ?
C14 Cs1 Cs1 130.18(15) 4_565 1_455 ?
C14 Cs1 Cs1 111.67(14) 2_657 1_455 ?
Cs1 Cs1 Cs1 180.00(2) 1_655 1_455 ?
C1 O1 Cs1 117.3(6) . . ?
C10 N1 Cs1 141.6(8) . 4_666 ?
C11 N2 Cs1 126.5(7) . 1_655 ?
C11 N2 Cs1 118.6(7) . . ?
Cs1 N2 Cs1 114.2(3) 1_655 . ?
C13 N3 Cs1 130.9(7) . 2_547 ?
C14 N4 Cs1 137.8(7) . 4_666 ?
C14 N4 Cs1 93.0(9) . 4_566 ?
Cs1 N4 Cs1 104.6(3) 4_666 4_566 ?
C14 N4 Cs1 93.2(8) . 2_647 ?
Cs1 N4 Cs1 104.2(3) 4_666 2_647 ?
Cs1 N4 Cs1 128.7(3) 4_566 2_647 ?
O1 C1 C2 124.0(8) . . ?
O1 C1 C8 118.8(7) . . ?
C2 C1 C8 117.0(7) . . ?
C7 C2 C3 120.3(8) . . ?
C7 C2 C1 117.3(8) . . ?
C3 C2 C1 122.4(7) . . ?
C4 C3 C2 120.5(9) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 118.9(9) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 121.3(9) . . ?
C6 C5 Br1 119.3(7) . . ?
C4 C5 Br1 119.4(8) . . ?
C5 C6 C7 120.6(8) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.4(9) . . ?
C2 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C12 C8 C9 129.3(8) . . ?
C12 C8 C1 117.1(7) . . ?
C9 C8 C1 113.6(7) . . ?
C11 C9 C8 118.8(8) . . ?
C11 C9 C10 118.4(8) . . ?
C8 C9 C10 122.8(8) . . ?
N1 C10 C9 176.9(13) . . ?
N2 C11 C9 175.9(10) . . ?
C8 C12 C13 120.8(8) . . ?
C8 C12 C14 124.7(8) . . ?
C13 C12 C14 114.5(7) . . ?
N3 C13 C12 177.4(10) . . ?
N4 C14 C12 176.8(10) . . ?
N4 C14 Cs1 70.0(8) . 4_566 ?
C12 C14 Cs1 107.2(6) . 4_566 ?
N4 C14 Cs1 70.0(8) . 2_647 ?
C12 C14 Cs1 110.5(6) . 2_647 ?
Cs1 C14 Cs1 116.1(2) 4_566 2_647 ?

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
Cs1 O1 C1 C2 -64.1(10) . . . . ?
Cs1 O1 C1 C8 110.2(7) . . . . ?
O1 C1 C2 C7 0.4(13) . . . . ?
C8 C1 C2 C7 -174.0(7) . . . . ?
O1 C1 C2 C3 -180.0(9) . . . . ?
C8 C1 C2 C3 5.7(12) . . . . ?
C7 C2 C3 C4 1.4(14) . . . . ?
C1 C2 C3 C4 -178.2(8) . . . . ?
C2 C3 C4 C5 -0.3(14) . . . . ?
C3 C4 C5 C6 -0.7(15) . . . . ?
C3 C4 C5 Br1 178.7(7) . . . . ?
C4 C5 C6 C7 0.7(16) . . . . ?
Br1 C5 C6 C7 -178.7(8) . . . . ?
C3 C2 C7 C6 -1.4(14) . . . . ?
C1 C2 C7 C6 178.2(9) . . . . ?
C5 C6 C7 C2 0.4(15) . . . . ?
O1 C1 C8 C12 89.0(10) . . . . ?
C2 C1 C8 C12 -96.3(9) . . . . ?
O1 C1 C8 C9 -90.1(10) . . . . ?
C2 C1 C8 C9 84.5(9) . . . . ?
C12 C8 C9 C11 -177.0(8) . . . . ?
C1 C8 C9 C11 2.0(10) . . . . ?
C12 C8 C9 C10 2.1(14) . . . . ?
C1 C8 C9 C10 -178.9(8) . . . . ?
C9 C8 C12 C13 176.6(8) . . . . ?
C1 C8 C12 C13 -2.4(12) . . . . ?
C9 C8 C12 C14 -5.7(14) . . . . ?
C1 C8 C12 C14 175.3(8) . . . . ?
Cs1 N4 C14 Cs1 -115.6(13) 4_666 . . 4_566 ?
Cs1 N4 C14 Cs1 129.0(3) 2_647 . . 4_566 ?
Cs1 N4 C14 Cs1 115.3(13) 4_666 . . 2_647 ?
Cs1 N4 C14 Cs1 -129.0(3) 4_566 . . 2_647 ?
C8 C12 C14 Cs1 113.7(8) . . . 4_566 ?
C13 C12 C14 Cs1 -68.5(8) . . . 4_566 ?
C8 C12 C14 Cs1 -119.0(7) . . . 2_647 ?
C13 C12 C14 Cs1 58.8(8) . . . 2_647 ?

_refine_diff_density_max         2.629
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.236

####################################################################### 
# 
# 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_az275
_database_code_depnum_ccdc_archive 'CCDC 1574996'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 N4 Na O2'
_chemical_formula_sum            'C14 H7 N4 Na O2'
_chemical_formula_weight         286.23

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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.7106(6)
_cell_length_b                   17.5383(7)
_cell_length_c                   6.8408(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.036(4)
_cell_angle_gamma                90
_cell_volume                     1350.32(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    670
_cell_measurement_theta_min      4
_cell_measurement_theta_max      50

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .16
_exptl_crystal_size_mid          .13
_exptl_crystal_size_min          .05
_exptl_absorpt_coefficient_mu    1.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.970

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            5677
_diffrn_reflns_av_unetI/netI     0.1872
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.928
_diffrn_reflns_theta_max         73.012
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2655
_reflns_number_gt                876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1358P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0045(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     197
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1970
_refine_ls_R_factor_gt           0.0934
_refine_ls_wR_factor_ref         0.3238
_refine_ls_wR_factor_gt          0.2947
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.4504(3) 0.20416(17) 0.6872(6) 0.0582(11) Uani 1 1 d . . . . .
O1 O 0.2950(5) 0.1877(3) 0.8272(12) 0.078(2) Uani 1 1 d . . . . .
O2 O 0.5833(5) 0.2500(3) 1.0087(10) 0.0577(17) Uani 1 1 d D . . . .
N1 N 0.4367(7) -0.0875(4) 1.1911(14) 0.076(3) Uani 1 1 d . . . . .
N2 N 0.3785(7) 0.1393(5) 1.3566(17) 0.088(3) Uani 1 1 d . . . . .
N3 N 0.3039(7) -0.1255(4) 0.6899(15) 0.077(3) Uani 1 1 d . . . . .
N4 N 0.0950(9) 0.0621(5) 0.3760(17) 0.084(3) Uani 1 1 d . . . . .
C1 C 0.2229(7) 0.1394(4) 0.8545(15) 0.052(2) Uani 1 1 d . . . . .
C2 C 0.1012(7) 0.1579(4) 0.8598(14) 0.046(2) Uani 1 1 d . . . . .
C3 C 0.0695(8) 0.2366(4) 0.8550(13) 0.055(2) Uani 1 1 d . . . . .
H3 H 0.1246 0.2743 0.8507 0.065 Uiso 1 1 calc . U . . .
C4 C -0.0428(9) 0.2562(6) 0.8576(16) 0.070(3) Uani 1 1 d . . . . .
H4 H -0.0633 0.3074 0.8603 0.084 Uiso 1 1 calc . U . . .
C5 C -0.1280(8) 0.1964(7) 0.8587(17) 0.078(3) Uani 1 1 d . . . . .
H5 H -0.2038 0.2101 0.8641 0.094 Uiso 1 1 calc . U . . .
C6 C -0.0969(9) 0.1221(6) 0.8662(18) 0.080(3) Uani 1 1 d . . . . .
H6 H -0.1532 0.0847 0.8662 0.096 Uiso 1 1 calc . U . . .
C7 C 0.0227(7) 0.1030(5) 0.8690(15) 0.063(3) Uani 1 1 d . . . . .
H7 H 0.0438 0.0519 0.8671 0.075 Uiso 1 1 calc . U . . .
C8 C 0.2658(7) 0.0582(4) 0.8802(15) 0.048(2) Uani 1 1 d . . . . .
C9 C 0.3357(7) 0.0410(4) 1.0767(15) 0.049(2) Uani 1 1 d . . . . .
C10 C 0.3576(7) 0.0954(5) 1.2301(17) 0.060(3) Uani 1 1 d . . . . .
C11 C 0.3909(7) -0.0310(5) 1.1329(15) 0.057(2) Uani 1 1 d . . . . .
C12 C 0.2338(7) 0.0119(4) 0.7073(15) 0.053(2) Uani 1 1 d . . . . .
C13 C 0.2742(8) -0.0650(5) 0.7024(16) 0.059(2) Uani 1 1 d . . . . .
C14 C 0.1567(9) 0.0399(5) 0.5247(18) 0.064(3) Uani 1 1 d . . . . .
H2 H 0.632(7) 0.288(4) 1.046(14) 0.096 Uiso 1 1 d D U . . .
H21 H 0.595(8) 0.232(5) 0.899(10) 0.096 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O1 2.297(7) . ?
Na1 O2 2.368(7) 4_565 ?
Na1 O2 2.452(7) . ?
Na1 N1 2.453(8) 3_657 ?
Na1 N2 2.463(11) 1_554 ?
Na1 Na1 3.779(2) 4_566 ?
Na1 Na1 3.779(2) 4_565 ?
O1 C1 1.245(9) . ?
O2 Na1 2.368(7) 4_566 ?
N1 C11 1.145(10) . ?
N1 Na1 2.453(8) 3_657 ?
N2 C10 1.133(12) . ?
N2 Na1 2.463(11) 1_556 ?
N3 C13 1.127(10) . ?
N4 C14 1.141(12) . ?
C1 C2 1.472(11) . ?
C1 C8 1.504(11) . ?
C2 C7 1.344(11) . ?
C2 C3 1.428(10) . ?
C3 C4 1.365(12) . ?
C4 C5 1.449(14) . ?
C5 C6 1.351(15) . ?
C6 C7 1.436(13) . ?
C8 C12 1.398(12) . ?
C8 C9 1.400(12) . ?
C9 C10 1.389(13) . ?
C9 C11 1.422(11) . ?
C12 C14 1.412(15) . ?
C12 C13 1.434(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na1 O2 165.2(3) . 4_565 ?
O1 Na1 O2 92.7(3) . . ?
O2 Na1 O2 90.4(2) 4_565 . ?
O1 Na1 N1 99.7(3) . 3_657 ?
O2 Na1 N1 95.1(3) 4_565 3_657 ?
O2 Na1 N1 79.7(3) . 3_657 ?
O1 Na1 N2 102.4(3) . 1_554 ?
O2 Na1 N2 77.9(3) 4_565 1_554 ?
O2 Na1 N2 161.1(3) . 1_554 ?
N1 Na1 N2 86.7(3) 3_657 1_554 ?
O1 Na1 Na1 58.6(2) . 4_566 ?
O2 Na1 Na1 119.13(19) 4_565 4_566 ?
O2 Na1 Na1 37.58(15) . 4_566 ?
N1 Na1 Na1 100.5(2) 3_657 4_566 ?
N2 Na1 Na1 160.4(2) 1_554 4_566 ?
O1 Na1 Na1 129.0(2) . 4_565 ?
O2 Na1 Na1 39.16(17) 4_565 4_565 ?
O2 Na1 Na1 120.88(18) . 4_565 ?
N1 Na1 Na1 121.8(2) 3_657 4_565 ?
N2 Na1 Na1 56.7(3) 1_554 4_565 ?
Na1 Na1 Na1 129.65(16) 4_566 4_565 ?
C1 O1 Na1 142.8(6) . . ?
Na1 O2 Na1 103.3(2) 4_566 . ?
C11 N1 Na1 175.4(8) . 3_657 ?
C10 N2 Na1 164.1(9) . 1_556 ?
O1 C1 C2 123.8(7) . . ?
O1 C1 C8 116.3(7) . . ?
C2 C1 C8 120.0(6) . . ?
C7 C2 C3 121.1(7) . . ?
C7 C2 C1 121.5(6) . . ?
C3 C2 C1 117.4(7) . . ?
C4 C3 C2 119.3(8) . . ?
C3 C4 C5 119.0(8) . . ?
C6 C5 C4 121.4(8) . . ?
C5 C6 C7 118.5(9) . . ?
C2 C7 C6 120.6(8) . . ?
C12 C8 C9 129.5(7) . . ?
C12 C8 C1 116.6(8) . . ?
C9 C8 C1 113.9(7) . . ?
C10 C9 C8 120.9(7) . . ?
C10 C9 C11 115.5(9) . . ?
C8 C9 C11 123.6(8) . . ?
N2 C10 C9 178.2(9) . . ?
N1 C11 C9 175.5(11) . . ?
C8 C12 C14 120.2(7) . . ?
C8 C12 C13 123.6(8) . . ?
C14 C12 C13 116.2(8) . . ?
N3 C13 C12 177.1(12) . . ?
N4 C14 C12 179.4(12) . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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_yak409
_database_code_depnum_ccdc_archive 'CCDC 1575024'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Br N5 O'
_chemical_formula_sum            'C14 H8 Br N5 O'
_chemical_formula_weight         342.16

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8525(3)
_cell_length_b                   10.3391(3)
_cell_length_c                   15.2660(4)
_cell_angle_alpha                107.694(2)
_cell_angle_beta                 91.607(2)
_cell_angle_gamma                95.332(2)
_cell_volume                     1472.51(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2760
_cell_measurement_theta_min      3
_cell_measurement_theta_max      60

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .27
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .23
_exptl_absorpt_coefficient_mu    3.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            11909
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.515
_diffrn_reflns_theta_max         72.854
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5512
_reflns_number_gt                4658
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0725P)²+0.5813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0051(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5512
_refine_ls_number_parameters     412
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.58092(4) 0.98227(4) 0.21039(3) 0.07326(16) Uani 1 1 d . . . . .
O1 O 0.3205(2) 1.3429(2) -0.05154(15) 0.0644(6) Uani 1 1 d . . . . .
N1 N 0.0335(4) 1.0610(3) -0.1253(2) 0.0830(9) Uani 1 1 d . . . . .
N2 N -0.2166(3) 1.3508(3) 0.0424(2) 0.0648(7) Uani 1 1 d . . . . .
N3 N -0.0326(3) 1.6262(3) 0.19909(18) 0.0570(6) Uani 1 1 d . . . . .
N4 N 0.3963(3) 1.5970(3) 0.1842(2) 0.0772(9) Uani 1 1 d . . . . .
N5 N 0.9694(3) 0.9568(4) 0.3216(2) 0.0739(8) Uani 1 1 d D . . . .
C1 C 0.2751(3) 1.3107(3) 0.01246(17) 0.0438(5) Uani 1 1 d . . . . .
C2 C 0.3447(3) 1.2273(2) 0.05926(16) 0.0408(5) Uani 1 1 d . . . . .
C3 C 0.4821(3) 1.2128(3) 0.04586(19) 0.0470(6) Uani 1 1 d . . . . .
H3 H 0.5271 1.2526 0.0062 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5520(3) 1.1404(3) 0.0906(2) 0.0523(6) Uani 1 1 d . . . . .
H4 H 0.6442 1.1317 0.0821 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4832(3) 1.0808(3) 0.14848(18) 0.0499(6) Uani 1 1 d . . . . .
C6 C 0.3468(3) 1.0907(3) 0.1618(2) 0.0549(7) Uani 1 1 d . . . . .
H6 H 0.3019 1.0476 0.1998 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2774(3) 1.1657(3) 0.11774(19) 0.0502(6) Uani 1 1 d . . . . .
H7 H 0.1856 1.1752 0.1272 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1422(3) 1.3636(3) 0.04901(17) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.0232(3) 1.2838(3) 0.00491(17) 0.0451(6) Uani 1 1 d . . . . .
C10 C 0.0296(3) 1.1605(3) -0.0670(2) 0.0569(7) Uani 1 1 d . . . . .
C11 C -0.1097(3) 1.3208(3) 0.02641(18) 0.0478(6) Uani 1 1 d . . . . .
C12 C 0.1564(3) 1.4857(3) 0.12020(17) 0.0426(5) Uani 1 1 d . . . . .
C13 C 0.0484(3) 1.5605(3) 0.16231(17) 0.0432(5) Uani 1 1 d . . . . .
C14 C 0.2892(3) 1.5480(3) 0.1555(2) 0.0531(6) Uani 1 1 d . . . . .
Br1A Br 0.90841(5) 0.27264(4) 0.25947(3) 0.07894(17) Uani 1 1 d . . . . .
O1A O 1.2300(2) 0.8580(2) 0.56590(16) 0.0664(6) Uani 1 1 d . . . . .
N1A N 1.4226(3) 0.6086(4) 0.6567(2) 0.0782(8) Uani 1 1 d . . . . .
N2A N 1.7747(3) 0.7961(4) 0.5604(3) 0.0869(10) Uani 1 1 d . . . . .
N3A N 1.6945(3) 0.8138(3) 0.3500(2) 0.0678(7) Uani 1 1 d . . . . .
N4A N 1.2616(3) 0.8887(3) 0.3294(2) 0.0779(8) Uani 1 1 d . . . . .
N5A N -0.3304(3) 1.5303(3) 0.2023(2) 0.0556(6) Uani 1 1 d . . . . .
C1A C 1.2729(3) 0.7666(3) 0.50677(18) 0.0477(6) Uani 1 1 d . . . . .
C2A C 1.1860(3) 0.6465(3) 0.44760(18) 0.0466(6) Uani 1 1 d . . . . .
C3A C 1.0449(3) 0.6427(3) 0.45055(19) 0.0538(6) Uani 1 1 d . . . . .
H3A H 1.0064 0.7153 0.4903 0.065 Uiso 1 1 calc R U . . .
C4A C 0.9615(3) 0.5320(3) 0.3949(2) 0.0577(7) Uani 1 1 d . . . . .
H4A H 0.8670 0.5296 0.3963 0.069 Uiso 1 1 calc R U . . .
C5A C 1.0208(3) 0.4250(3) 0.33726(19) 0.0549(7) Uani 1 1 d . . . . .
C6A C 1.1601(3) 0.4256(3) 0.3335(2) 0.0563(7) Uani 1 1 d . . . . .
H6A H 1.1977 0.3518 0.2944 0.068 Uiso 1 1 calc R U . . .
C7A C 1.2433(3) 0.5369(3) 0.38851(19) 0.0516(6) Uani 1 1 d . . . . .
H7A H 1.3376 0.5388 0.3862 0.062 Uiso 1 1 calc R U . . .
C8A C 1.4253(3) 0.7777(3) 0.49008(18) 0.0465(6) Uani 1 1 d . . . . .
C9A C 1.5138(3) 0.7405(3) 0.5488(2) 0.0533(6) Uani 1 1 d . . . . .
C10A C 1.4618(3) 0.6694(3) 0.6096(2) 0.0598(7) Uani 1 1 d . . . . .
C11A C 1.6590(4) 0.7692(4) 0.5531(2) 0.0630(8) Uani 1 1 d . . . . .
C12A C 1.4579(3) 0.8247(3) 0.41620(19) 0.0491(6) Uani 1 1 d . . . . .
C13A C 1.5896(3) 0.8215(3) 0.3804(2) 0.0531(7) Uani 1 1 d . . . . .
C14A C 1.3519(3) 0.8623(3) 0.3667(2) 0.0568(7) Uani 1 1 d . . . . .
H51A H -0.346(4) 1.476(4) 0.243(3) 0.074(11) Uiso 1 1 d . . . . .
H52A H -0.404(5) 1.575(5) 0.196(3) 0.094(14) Uiso 1 1 d . . . . .
H53A H -0.309(4) 1.464(5) 0.152(3) 0.091(14) Uiso 1 1 d . . . . .
H54A H -0.261(5) 1.583(5) 0.219(3) 0.084(13) Uiso 1 1 d . . . . .
H51 H 0.950(5) 0.959(5) 0.271(3) 0.12(2) Uiso 1 1 d D . . . .
H52 H 0.923(6) 0.861(7) 0.325(5) 0.20(3) Uiso 1 1 d D . . . .
H53 H 1.062(5) 0.935(6) 0.331(4) 0.15(2) Uiso 1 1 d D . . . .
H54 H 0.948(9) 1.011(8) 0.374(3) 0.51(12) Uiso 1 1 d 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
Br1 C5 1.891(3) . ?
O1 C1 1.209(3) . ?
N1 C10 1.143(4) . ?
N2 C11 1.138(4) . ?
N3 C13 1.144(3) . ?
N4 C14 1.141(4) . ?
N5 H51 0.79(4) . ?
N5 H52 1.07(5) . ?
N5 H53 0.98(4) . ?
N5 H54 0.874(19) . ?
C1 C2 1.476(3) . ?
C1 C8 1.522(3) . ?
C2 C3 1.390(4) . ?
C2 C7 1.394(3) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C12 1.385(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.415(4) . ?
C9 C11 1.417(4) . ?
C12 C14 1.419(4) . ?
C12 C13 1.425(4) . ?
Br1A C5A 1.892(3) . ?
O1A C1A 1.210(3) . ?
N1A C10A 1.142(4) . ?
N2A C11A 1.142(5) . ?
N3A C13A 1.145(4) . ?
N4A C14A 1.141(4) . ?
N5A H51A 0.96(4) . ?
N5A H52A 0.91(5) . ?
N5A H53A 0.90(5) . ?
N5A H54A 0.82(5) . ?
C1A C2A 1.473(4) . ?
C1A C8A 1.529(4) . ?
C2A C3A 1.390(4) . ?
C2A C7A 1.394(4) . ?
C3A C4A 1.379(4) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.377(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.375(5) . ?
C6A C7A 1.378(4) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A C12A 1.391(4) . ?
C8A C9A 1.393(4) . ?
C9A C10A 1.427(4) . ?
C9A C11A 1.430(5) . ?
C12A C13A 1.421(4) . ?
C12A C14A 1.422(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
H51 N5 H52 106(4) . . ?
H51 N5 H53 115(4) . . ?
H52 N5 H53 94(4) . . ?
H51 N5 H54 128(5) . . ?
H52 N5 H54 100(4) . . ?
H53 N5 H54 107(4) . . ?
O1 C1 C2 123.4(2) . . ?
O1 C1 C8 118.1(2) . . ?
C2 C1 C8 118.4(2) . . ?
C3 C2 C7 119.4(2) . . ?
C3 C2 C1 118.7(2) . . ?
C7 C2 C1 121.9(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 Br1 119.5(2) . . ?
C4 C5 Br1 118.5(2) . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C12 C8 C9 129.1(2) . . ?
C12 C8 C1 115.4(2) . . ?
C9 C8 C1 115.5(2) . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 C11 123.3(2) . . ?
C10 C9 C11 115.8(2) . . ?
N1 C10 C9 179.3(4) . . ?
N2 C11 C9 179.0(3) . . ?
C8 C12 C14 119.2(2) . . ?
C8 C12 C13 126.3(2) . . ?
C14 C12 C13 114.5(2) . . ?
N3 C13 C12 176.1(3) . . ?
N4 C14 C12 179.3(4) . . ?
H51A N5A H52A 112(4) . . ?
H51A N5A H53A 98(4) . . ?
H52A N5A H53A 117(4) . . ?
H51A N5A H54A 112(4) . . ?
H52A N5A H54A 112(4) . . ?
H53A N5A H54A 106(4) . . ?
O1A C1A C2A 123.7(3) . . ?
O1A C1A C8A 118.5(3) . . ?
C2A C1A C8A 117.7(2) . . ?
C3A C2A C7A 119.6(3) . . ?
C3A C2A C1A 119.5(2) . . ?
C7A C2A C1A 120.9(3) . . ?
C4A C3A C2A 120.4(3) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C5A C4A C3A 118.8(3) . . ?
C5A C4A H4A 120.6 . . ?
C3A C4A H4A 120.6 . . ?
C6A C5A C4A 122.0(3) . . ?
C6A C5A Br1A 118.5(2) . . ?
C4A C5A Br1A 119.5(3) . . ?
C5A C6A C7A 119.2(3) . . ?
C5A C6A H6A 120.4 . . ?
C7A C6A H6A 120.4 . . ?
C6A C7A C2A 120.0(3) . . ?
C6A C7A H7A 120.0 . . ?
C2A C7A H7A 120.0 . . ?
C12A C8A C9A 127.9(3) . . ?
C12A C8A C1A 114.4(2) . . ?
C9A C8A C1A 117.6(2) . . ?
C8A C9A C10A 120.5(3) . . ?
C8A C9A C11A 123.8(3) . . ?
C10A C9A C11A 115.7(3) . . ?
N1A C10A C9A 177.5(4) . . ?
N2A C11A C9A 177.0(4) . . ?
C8A C12A C13A 122.9(3) . . ?
C8A C12A C14A 119.0(3) . . ?
C13A C12A C14A 117.6(2) . . ?
N3A C13A C12A 177.5(3) . . ?
N4A C14A C12A 176.0(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
O1 C1 C2 C3 16.5(4) . . . . ?
C8 C1 C2 C3 -161.0(2) . . . . ?
O1 C1 C2 C7 -165.0(3) . . . . ?
C8 C1 C2 C7 17.6(4) . . . . ?
C7 C2 C3 C4 -1.0(4) . . . . ?
C1 C2 C3 C4 177.6(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 Br1 -179.6(2) . . . . ?
C4 C5 C6 C7 -1.8(4) . . . . ?
Br1 C5 C6 C7 178.5(2) . . . . ?
C5 C6 C7 C2 1.5(4) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C1 C2 C7 C6 -178.7(3) . . . . ?
O1 C1 C8 C12 -91.8(3) . . . . ?
C2 C1 C8 C12 85.8(3) . . . . ?
O1 C1 C8 C9 87.0(3) . . . . ?
C2 C1 C8 C9 -95.4(3) . . . . ?
C12 C8 C9 C10 -179.7(3) . . . . ?
C1 C8 C9 C10 1.7(4) . . . . ?
C12 C8 C9 C11 2.0(4) . . . . ?
C1 C8 C9 C11 -176.6(2) . . . . ?
C9 C8 C12 C14 178.9(3) . . . . ?
C1 C8 C12 C14 -2.5(3) . . . . ?
C9 C8 C12 C13 -2.7(4) . . . . ?
C1 C8 C12 C13 175.9(2) . . . . ?
O1A C1A C2A C3A 8.1(4) . . . . ?
C8A C1A C2A C3A -170.0(2) . . . . ?
O1A C1A C2A C7A -172.1(3) . . . . ?
C8A C1A C2A C7A 9.8(4) . . . . ?
C7A C2A C3A C4A -0.6(4) . . . . ?
C1A C2A C3A C4A 179.2(3) . . . . ?
C2A C3A C4A C5A 0.7(4) . . . . ?
C3A C4A C5A C6A -0.1(4) . . . . ?
C3A C4A C5A Br1A -179.4(2) . . . . ?
C4A C5A C6A C7A -0.5(4) . . . . ?
Br1A C5A C6A C7A 178.8(2) . . . . ?
C5A C6A C7A C2A 0.6(4) . . . . ?
C3A C2A C7A C6A 0.0(4) . . . . ?
C1A C2A C7A C6A -179.8(3) . . . . ?
O1A C1A C8A C12A -98.7(3) . . . . ?
C2A C1A C8A C12A 79.5(3) . . . . ?
O1A C1A C8A C9A 81.4(3) . . . . ?
C2A C1A C8A C9A -100.4(3) . . . . ?
C12A C8A C9A C10A -167.6(3) . . . . ?
C1A C8A C9A C10A 12.3(4) . . . . ?
C12A C8A C9A C11A 12.4(5) . . . . ?
C1A C8A C9A C11A -167.7(3) . . . . ?
C9A C8A C12A C13A 10.3(4) . . . . ?
C1A C8A C12A C13A -169.6(2) . . . . ?
C9A C8A C12A C14A -177.7(3) . . . . ?
C1A C8A C12A C14A 2.4(4) . . . . ?

_refine_diff_density_max         0.981
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_yak407
_database_code_depnum_ccdc_archive 'CCDC 1575023'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N5 O2'
_chemical_formula_sum            'C15 H11 N5 O2'
_chemical_formula_weight         293.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.0933(4)
_cell_length_b                   16.1822(6)
_cell_length_c                   7.3295(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.538(3)
_cell_angle_gamma                90
_cell_volume                     1550.00(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1734
_cell_measurement_theta_min      4
_cell_measurement_theta_max      55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .18
_exptl_crystal_size_min          .16
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            11472
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.349
_diffrn_reflns_theta_max         70.814
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2944
_reflns_number_gt                2188
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0060(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2944
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16606(9) 0.17463(6) 0.83046(19) 0.0716(4) Uani 1 1 d . . . . .
O2 O 0.61531(10) 0.22628(10) 1.1823(2) 0.0913(4) Uani 1 1 d . . . . .
N1 N 0.10670(13) 0.12640(8) 1.2980(2) 0.0745(4) Uani 1 1 d . . . . .
N2 N 0.08840(12) -0.12841(8) 1.1485(2) 0.0700(4) Uani 1 1 d . . . . .
N3 N 0.14473(12) -0.15797(10) 0.7128(2) 0.0802(5) Uani 1 1 d . . . . .
N4 N 0.33525(16) 0.03528(12) 0.5113(3) 0.1019(6) Uani 1 1 d . . . . .
N5 N 0.00858(12) 0.27174(8) 1.06854(18) 0.0528(3) Uani 1 1 d . . . . .
C1 C 0.23039(10) 0.12756(8) 0.89837(19) 0.0472(3) Uani 1 1 d . . . . .
C2 C 0.33026(10) 0.15385(7) 0.97312(18) 0.0446(3) Uani 1 1 d . . . . .
C3 C 0.35683(12) 0.23752(8) 0.9680(2) 0.0516(4) Uani 1 1 d . . . . .
C4 C 0.45108(13) 0.26412(10) 1.0367(2) 0.0592(4) Uani 1 1 d . . . . .
C5 C 0.52072(12) 0.20718(11) 1.1109(2) 0.0635(4) Uani 1 1 d . . . . .
C6 C 0.49459(13) 0.12414(11) 1.1204(3) 0.0666(4) Uani 1 1 d . . . . .
C7 C 0.40089(11) 0.09766(9) 1.0527(2) 0.0557(4) Uani 1 1 d . . . . .
C8 C 0.20023(9) 0.03694(7) 0.90906(18) 0.0435(3) Uani 1 1 d . . . . .
C9 C 0.14821(10) 0.01600(7) 1.06350(18) 0.0451(3) Uani 1 1 d . . . . .
C10 C 0.12608(11) 0.07720(8) 1.1937(2) 0.0528(4) Uani 1 1 d . . . . .
C11 C 0.11526(10) -0.06444(8) 1.10674(19) 0.0493(3) Uani 1 1 d . . . . .
C12 C 0.22187(11) -0.01342(8) 0.76362(19) 0.0502(3) Uani 1 1 d . . . . .
C13 C 0.18052(11) -0.09418(9) 0.7382(2) 0.0565(4) Uani 1 1 d . . . . .
C14 C 0.28424(13) 0.01479(10) 0.6238(2) 0.0643(4) Uani 1 1 d . . . . .
C15 C 0.6489(2) 0.3104(2) 1.1737(5) 0.1081(9) Uani 1 1 d . . . . .
H1 H 0.3826(14) 0.0386(12) 1.061(2) 0.071(5) Uiso 1 1 d . . . . .
H2 H 0.4659(14) 0.3227(12) 1.033(3) 0.072(5) Uiso 1 1 d . . . . .
H3 H 0.3067(14) 0.2788(11) 0.915(3) 0.070(5) Uiso 1 1 d . . . . .
H4 H 0.5439(17) 0.0856(13) 1.176(3) 0.093(6) Uiso 1 1 d . . . . .
H5 H 0.597(2) 0.3497(19) 1.238(4) 0.131(10) Uiso 1 1 d . . . . .
H6 H 0.041(3) 0.306(2) 0.988(5) 0.147(11) Uiso 1 1 d . . . . .
H7 H 0.712(3) 0.3079(18) 1.228(4) 0.130(10) Uiso 1 1 d . . . . .
H8 H 0.644(3) 0.330(2) 1.043(6) 0.159(13) Uiso 1 1 d . . . . .
H9 H -0.028(3) 0.303(2) 1.139(5) 0.165(13) Uiso 1 1 d . . . . .
H10 H -0.023(4) 0.226(4) 1.037(8) 0.24(2) Uiso 1 1 d . . . . .
H11 H 0.056(7) 0.259(5) 1.155(11) 0.32(3) Uiso 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 C1 1.2188(17) . ?
O2 C5 1.350(2) . ?
O2 C15 1.433(3) . ?
N1 C10 1.1432(19) . ?
N2 C11 1.1411(18) . ?
N3 C13 1.1442(19) . ?
N4 C14 1.142(2) . ?
N5 H6 0.92(4) . ?
N5 H9 0.88(4) . ?
N5 H10 0.87(6) . ?
N5 H11 0.88(9) . ?
C1 C2 1.4500(19) . ?
C1 C8 1.5219(17) . ?
C2 C7 1.399(2) . ?
C2 C3 1.3990(18) . ?
C3 C4 1.373(2) . ?
C3 H3 0.998(19) . ?
C4 C5 1.384(3) . ?
C4 H2 0.969(19) . ?
C5 C6 1.389(2) . ?
C6 C7 1.364(2) . ?
C6 H4 0.97(2) . ?
C7 H1 0.989(19) . ?
C8 C12 1.3851(19) . ?
C8 C9 1.3983(19) . ?
C9 C11 1.4135(18) . ?
C9 C10 1.4173(19) . ?
C12 C13 1.422(2) . ?
C12 C14 1.424(2) . ?
C15 H5 1.07(3) . ?
C15 H7 0.90(3) . ?
C15 H8 1.01(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
C5 O2 C15 118.5(2) . . ?
H6 N5 H9 109(3) . . ?
H6 N5 H10 124(4) . . ?
H9 N5 H10 112(4) . . ?
H6 N5 H11 106(5) . . ?
H9 N5 H11 95(5) . . ?
H10 N5 H11 107(5) . . ?
O1 C1 C2 123.73(12) . . ?
O1 C1 C8 116.63(12) . . ?
C2 C1 C8 119.60(11) . . ?
C7 C2 C3 118.77(13) . . ?
C7 C2 C1 121.64(12) . . ?
C3 C2 C1 119.58(12) . . ?
C4 C3 C2 120.86(15) . . ?
C4 C3 H3 119.2(10) . . ?
C2 C3 H3 120.0(10) . . ?
C3 C4 C5 119.40(14) . . ?
C3 C4 H2 118.3(11) . . ?
C5 C4 H2 122.3(11) . . ?
O2 C5 C4 124.49(16) . . ?
O2 C5 C6 115.14(16) . . ?
C4 C5 C6 120.35(15) . . ?
C7 C6 C5 120.30(16) . . ?
C7 C6 H4 120.7(13) . . ?
C5 C6 H4 118.9(13) . . ?
C6 C7 C2 120.29(14) . . ?
C6 C7 H1 119.8(11) . . ?
C2 C7 H1 119.9(11) . . ?
C12 C8 C9 127.84(12) . . ?
C12 C8 C1 117.47(11) . . ?
C9 C8 C1 114.59(11) . . ?
C8 C9 C11 125.13(11) . . ?
C8 C9 C10 120.37(11) . . ?
C11 C9 C10 114.50(12) . . ?
N1 C10 C9 178.97(17) . . ?
N2 C11 C9 177.34(16) . . ?
C8 C12 C13 123.17(12) . . ?
C8 C12 C14 121.24(12) . . ?
C13 C12 C14 115.53(12) . . ?
N3 C13 C12 177.42(18) . . ?
N4 C14 C12 178.13(18) . . ?
O2 C15 H5 109.9(16) . . ?
O2 C15 H7 102(2) . . ?
H5 C15 H7 116(3) . . ?
O2 C15 H8 110(2) . . ?
H5 C15 H8 103(3) . . ?
H7 C15 H8 116(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
O1 C1 C2 C7 178.81(14) . . . . ?
C8 C1 C2 C7 1.08(19) . . . . ?
O1 C1 C2 C3 -0.4(2) . . . . ?
C8 C1 C2 C3 -178.17(12) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -179.60(13) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C15 O2 C5 C4 -3.2(3) . . . . ?
C15 O2 C5 C6 178.5(2) . . . . ?
C3 C4 C5 O2 -179.96(15) . . . . ?
C3 C4 C5 C6 -1.7(2) . . . . ?
O2 C5 C6 C7 179.91(15) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C3 C2 C7 C6 -1.4(2) . . . . ?
C1 C2 C7 C6 179.39(14) . . . . ?
O1 C1 C8 C12 91.14(16) . . . . ?
C2 C1 C8 C12 -90.97(16) . . . . ?
O1 C1 C8 C9 -85.53(16) . . . . ?
C2 C1 C8 C9 92.36(14) . . . . ?
C12 C8 C9 C11 5.8(2) . . . . ?
C1 C8 C9 C11 -177.91(13) . . . . ?
C12 C8 C9 C10 -175.34(14) . . . . ?
C1 C8 C9 C10 0.92(18) . . . . ?
C9 C8 C12 C13 9.0(2) . . . . ?
C1 C8 C12 C13 -167.13(13) . . . . ?
C9 C8 C12 C14 -173.96(14) . . . . ?
C1 C8 C12 C14 9.9(2) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_yak424
_database_code_depnum_ccdc_archive 'CCDC 1575039'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 N10 O3'
_chemical_formula_sum            'C30 H24 N10 O3'
_chemical_formula_weight         572.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -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                   33.875(2)
_cell_length_b                   9.8866(5)
_cell_length_c                   8.8250(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.005(4)
_cell_angle_gamma                90
_cell_volume                     2955.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1675
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             1192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .10
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.709

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'

_diffrn_reflns_number            10348
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.659
_diffrn_reflns_theta_max         66.465
_diffrn_reflns_theta_full        66.465
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2592
_reflns_number_gt                1858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1546P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2592
_refine_ls_number_parameters     199
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2163
_refine_ls_wR_factor_gt          0.1999
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.08892(6) 0.35352(17) 0.7238(2) 0.0711(6) Uani 1 1 d . . . . .
N1 N 0.03764(8) 0.3314(2) 0.3845(3) 0.0758(7) Uani 1 1 d . . . . .
N2 N 0.03862(8) -0.1033(2) 0.4340(4) 0.0906(9) Uani 1 1 d . . . . .
N3 N 0.11172(8) -0.2100(2) 0.6537(3) 0.0800(8) Uani 1 1 d . . . . .
N4 N 0.17919(9) 0.1051(3) 0.8731(3) 0.0892(8) Uani 1 1 d . . . . .
C1 C 0.11168(7) 0.2896(2) 0.6445(3) 0.0510(6) Uani 1 1 d . . . . .
C2 C 0.10113(7) 0.1425(2) 0.6113(3) 0.0508(6) Uani 1 1 d . . . . .
C3 C 0.06927(8) 0.1241(2) 0.5106(3) 0.0552(6) Uani 1 1 d . . . . .
C4 C 0.12330(7) 0.0447(2) 0.6865(3) 0.0543(6) Uani 1 1 d . . . . .
C5 C 0.05147(8) 0.2376(3) 0.4398(3) 0.0597(6) Uani 1 1 d . . . . .
C6 C 0.05274(8) -0.0028(2) 0.4696(3) 0.0646(7) Uani 1 1 d . . . . .
C7 C 0.11654(8) -0.0963(2) 0.6669(3) 0.0596(6) Uani 1 1 d . . . . .
C8 C 0.15420(9) 0.0795(2) 0.7891(3) 0.0621(7) Uani 1 1 d . . . . .
C9 C 0.14633(7) 0.3503(2) 0.5752(3) 0.0509(6) Uani 1 1 d . . . . .
C10 C 0.15332(8) 0.4884(2) 0.5960(3) 0.0584(6) Uani 1 1 d . . . . .
H10 H 0.1371 0.5382 0.6591 0.070 Uiso 1 1 calc R U . . .
C11 C 0.18374(9) 0.5510(3) 0.5247(3) 0.0678(7) Uani 1 1 d . . . . .
H11 H 0.1875 0.6434 0.5381 0.081 Uiso 1 1 calc R U . . .
C12 C 0.20911(8) 0.4796(3) 0.4326(3) 0.0659(7) Uani 1 1 d . . . . .
C13 C 0.20285(9) 0.3414(3) 0.4154(3) 0.0700(8) Uani 1 1 d . . . . .
H13 H 0.2201 0.2912 0.3568 0.084 Uiso 1 1 calc R U . . .
C14 C 0.17176(8) 0.2774(2) 0.4831(3) 0.0599(6) Uani 1 1 d . . . . .
H14 H 0.1677 0.1854 0.4674 0.072 Uiso 1 1 calc R U . . .
C15 C 0.24270(11) 0.5490(4) 0.3550(4) 0.0963(11) Uani 1 1 d . . . . .
H15A H 0.2507 0.4958 0.2699 0.144 Uiso 1 1 calc R U . . .
H15B H 0.2645 0.5588 0.4250 0.144 Uiso 1 1 calc R U . . .
H15C H 0.2343 0.6366 0.3205 0.144 Uiso 1 1 calc R U . . .
O2 O 0.0000 0.6453(3) 0.2500 0.0775(8) Uani 1 2 d DS T P . .
H21 H 0.0196(5) 0.701(3) 0.230(5) 0.116 Uiso 1 1 d D U . . .
N5 N 0.04944(8) 0.3965(2) 0.0474(3) 0.0771(7) Uani 1 1 d . . . . .
H51 H 0.0525 0.4300 -0.0454 0.092 Uiso 1 1 d R U . . .
H52 H 0.0475 0.4670 0.1103 0.092 Uiso 1 1 d R U . . .
H53 H 0.0696 0.3464 0.0731 0.092 Uiso 1 1 d R U . . .
H54 H 0.0270 0.3515 0.0502 0.092 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(3) . ?
N1 C5 1.144(3) . ?
N2 C6 1.145(3) . ?
N3 C7 1.142(3) . ?
N4 C8 1.143(4) . ?
C1 C9 1.462(3) . ?
C1 C2 1.525(3) . ?
C2 C4 1.387(3) . ?
C2 C3 1.398(4) . ?
C3 C5 1.414(4) . ?
C3 C6 1.418(3) . ?
C4 C8 1.415(4) . ?
C4 C7 1.422(3) . ?
C9 C14 1.396(3) . ?
C9 C10 1.397(3) . ?
C10 C11 1.365(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(4) . ?
C12 C15 1.504(4) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O2 H21 0.883(17) . ?
N5 H51 0.8906 . ?
N5 H52 0.8943 . ?
N5 H53 0.8707 . ?
N5 H54 0.8815 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C9 123.0(2) . . ?
O1 C1 C2 117.0(2) . . ?
C9 C1 C2 119.92(18) . . ?
C4 C2 C3 128.3(2) . . ?
C4 C2 C1 116.8(2) . . ?
C3 C2 C1 115.0(2) . . ?
C2 C3 C5 119.8(2) . . ?
C2 C3 C6 125.0(2) . . ?
C5 C3 C6 115.2(2) . . ?
C2 C4 C8 121.7(2) . . ?
C2 C4 C7 122.7(2) . . ?
C8 C4 C7 115.6(2) . . ?
N1 C5 C3 178.3(3) . . ?
N2 C6 C3 178.1(3) . . ?
N3 C7 C4 178.5(3) . . ?
N4 C8 C4 178.6(3) . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C1 122.7(2) . . ?
C10 C9 C1 118.8(2) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 118.0(2) . . ?
C11 C12 C15 121.1(3) . . ?
C13 C12 C15 120.9(3) . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C9 120.1(2) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H51 N5 H52 107.0 . . ?
H51 N5 H53 110.3 . . ?
H52 N5 H53 110.3 . . ?
H51 N5 H54 109.2 . . ?
H52 N5 H54 107.6 . . ?
H53 N5 H54 112.2 . . ?

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
O1 C1 C2 C4 -106.3(3) . . . . ?
C9 C1 C2 C4 77.3(3) . . . . ?
O1 C1 C2 C3 72.1(3) . . . . ?
C9 C1 C2 C3 -104.3(3) . . . . ?
C4 C2 C3 C5 -177.2(2) . . . . ?
C1 C2 C3 C5 4.7(3) . . . . ?
C4 C2 C3 C6 2.0(4) . . . . ?
C1 C2 C3 C6 -176.2(2) . . . . ?
C3 C2 C4 C8 -178.1(2) . . . . ?
C1 C2 C4 C8 0.1(3) . . . . ?
C3 C2 C4 C7 1.5(4) . . . . ?
C1 C2 C4 C7 179.7(2) . . . . ?
O1 C1 C9 C14 -178.9(2) . . . . ?
C2 C1 C9 C14 -2.7(4) . . . . ?
O1 C1 C9 C10 -2.1(4) . . . . ?
C2 C1 C9 C10 174.1(2) . . . . ?
C14 C9 C10 C11 1.6(4) . . . . ?
C1 C9 C10 C11 -175.4(2) . . . . ?
C9 C10 C11 C12 -1.5(4) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C11 C12 C15 -179.7(3) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C15 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C9 -2.0(4) . . . . ?
C10 C9 C14 C13 0.1(4) . . . . ?
C1 C9 C14 C13 177.0(2) . . . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.083

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

data_shelx_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc1kqyt1
_database_code_depnum_ccdc_archive 'CCDC 1452034'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.6b01040 2016
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Sodium 2-benzoyl-1,1,3,3-tetracyanopropenide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H7 N4 Na O2'
_chemical_formula_sum            'C14 H7 N4 Na O2'
_chemical_formula_weight         286.23

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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.1536(2)
_cell_length_b                   10.1851(2)
_cell_length_c                   16.6349(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.739(2)
_cell_angle_gamma                90
_cell_volume                     1379.87(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       PRISM
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .15
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_T_max  0.970

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            5886
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.093
_diffrn_reflns_theta_max         73.234
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2727
_reflns_number_gt                2046
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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.
;



_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²+0.0421P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0192(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2727
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.01845(10) 0.65126(8) 0.55980(5) 0.0450(3) Uani 1 1 d . . . . .
O1 O 0.04912(17) 0.79861(17) 0.44651(8) 0.0457(4) Uani 1 1 d . . . . .
O2 O 0.2074(2) 0.48791(19) 0.50025(11) 0.0551(5) Uani 1 1 d . . . . .
N1 N -0.2415(2) 0.7645(2) 0.15534(11) 0.0525(5) Uani 1 1 d . . . . .
N2 N 0.0114(3) 0.5208(2) 0.33884(12) 0.0603(6) Uani 1 1 d . . . . .
N3 N 0.1361(3) 1.1812(2) 0.36502(13) 0.0583(6) Uani 1 1 d . . . . .
N4 N -0.0203(5) 1.0307(3) 0.12851(16) 0.0950(11) Uani 1 1 d . . . . .
C1 C 0.1324(2) 0.83231(19) 0.39133(10) 0.0325(4) Uani 1 1 d . . . . .
C2 C 0.3116(2) 0.84529(19) 0.40033(11) 0.0344(4) Uani 1 1 d . . . . .
C3 C 0.3862(3) 0.8265(3) 0.47615(14) 0.0485(6) Uani 1 1 d . . . . .
C4 C 0.5545(3) 0.8347(3) 0.48735(18) 0.0641(7) Uani 1 1 d . . . . .
C5 C 0.6480(3) 0.8635(3) 0.42334(19) 0.0675(8) Uani 1 1 d . . . . .
C6 C 0.5766(3) 0.8814(3) 0.34798(17) 0.0612(7) Uani 1 1 d . . . . .
C7 C 0.4080(3) 0.8715(2) 0.33550(14) 0.0452(5) Uani 1 1 d . . . . .
C8 C 0.0460(2) 0.85668(19) 0.30928(10) 0.0328(4) Uani 1 1 d . . . . .
C9 C -0.0286(2) 0.7477(2) 0.27384(11) 0.0368(4) Uani 1 1 d . . . . .
C10 C -0.0069(3) 0.6218(2) 0.30957(12) 0.0425(5) Uani 1 1 d . . . . .
C11 C -0.1430(2) 0.7552(2) 0.20659(11) 0.0393(5) Uani 1 1 d . . . . .
C12 C 0.0471(2) 0.9837(2) 0.27785(12) 0.0403(5) Uani 1 1 d . . . . .
C13 C 0.0988(3) 1.0924(2) 0.32619(13) 0.0429(5) Uani 1 1 d . . . . .
C14 C 0.0058(4) 1.0108(2) 0.19600(14) 0.0568(7) Uani 1 1 d . . . . .
H2 H 0.275(6) 0.509(5) 0.458(3) 0.126(16) Uiso 1 1 d . . . . .
H21 H 0.265(4) 0.467(3) 0.540(2) 0.066(9) Uiso 1 1 d . . . . .
H3 H 0.324(3) 0.810(3) 0.5223(17) 0.059(7) Uiso 1 1 d . . . . .
H4 H 0.595(5) 0.819(3) 0.540(2) 0.088(10) Uiso 1 1 d . . . . .
H5 H 0.766(5) 0.878(4) 0.430(2) 0.102(12) Uiso 1 1 d . . . . .
H6 H 0.646(4) 0.904(3) 0.3020(18) 0.070(8) Uiso 1 1 d . . . . .
H7 H 0.361(3) 0.884(3) 0.2818(16) 0.053(7) Uiso 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
Na1 O1 2.4313(16) . ?
Na1 N2 2.452(2) 3_566 ?
Na1 N3 2.493(2) 3_576 ?
Na1 O2 2.494(2) 3_566 ?
Na1 O2 2.504(2) . ?
Na1 N1 2.607(2) 4_676 ?
Na1 Na1 3.6723(16) 3_566 ?
O1 C1 1.217(2) . ?
O2 Na1 2.4942(19) 3_566 ?
N1 C11 1.147(3) . ?
N1 Na1 2.607(2) 4_575 ?
N2 C10 1.145(3) . ?
N2 Na1 2.452(2) 3_566 ?
N3 C13 1.144(3) . ?
N3 Na1 2.493(2) 3_576 ?
N4 C14 1.151(3) . ?
C1 C2 1.468(3) . ?
C1 C8 1.526(2) . ?
C2 C3 1.387(3) . ?
C2 C7 1.390(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.371(4) . ?
C5 C6 1.369(4) . ?
C6 C7 1.384(3) . ?
C8 C9 1.385(3) . ?
C8 C12 1.396(3) . ?
C9 C10 1.420(3) . ?
C9 C11 1.424(2) . ?
C12 C14 1.414(3) . ?
C12 C13 1.420(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Na1 N2 172.48(7) . 3_566 ?
O1 Na1 N3 92.27(7) . 3_576 ?
N2 Na1 N3 94.30(8) 3_566 3_576 ?
O1 Na1 O2 98.15(6) . 3_566 ?
N2 Na1 O2 76.91(7) 3_566 3_566 ?
N3 Na1 O2 102.04(7) 3_576 3_566 ?
O1 Na1 O2 90.89(6) . . ?
N2 Na1 O2 83.12(8) 3_566 . ?
N3 Na1 O2 171.39(7) 3_576 . ?
O2 Na1 O2 85.42(7) 3_566 . ?
O1 Na1 N1 99.63(6) . 4_676 ?
N2 Na1 N1 84.98(7) 3_566 4_676 ?
N3 Na1 N1 81.48(7) 3_576 4_676 ?
O2 Na1 N1 161.73(7) 3_566 4_676 ?
O2 Na1 N1 90.10(7) . 4_676 ?
O1 Na1 Na1 96.13(5) . 3_566 ?
N2 Na1 Na1 76.38(6) 3_566 3_566 ?
N3 Na1 Na1 144.67(7) 3_576 3_566 ?
O2 Na1 Na1 42.81(5) 3_566 3_566 ?
O2 Na1 Na1 42.61(5) . 3_566 ?
N1 Na1 Na1 130.25(6) 4_676 3_566 ?
C1 O1 Na1 147.19(14) . . ?
Na1 O2 Na1 94.58(7) 3_566 . ?
C11 N1 Na1 163.56(18) . 4_575 ?
C10 N2 Na1 156.8(2) . 3_566 ?
C13 N3 Na1 134.22(18) . 3_576 ?
O1 C1 C2 122.49(17) . . ?
O1 C1 C8 118.04(16) . . ?
C2 C1 C8 119.43(15) . . ?
C3 C2 C7 119.49(19) . . ?
C3 C2 C1 118.12(17) . . ?
C7 C2 C1 122.36(18) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C4 C3 119.7(2) . . ?
C6 C5 C4 120.8(2) . . ?
C5 C6 C7 120.2(2) . . ?
C6 C7 C2 119.5(2) . . ?
C9 C8 C12 126.48(16) . . ?
C9 C8 C1 115.16(16) . . ?
C12 C8 C1 118.36(16) . . ?
C8 C9 C10 120.13(16) . . ?
C8 C9 C11 123.34(18) . . ?
C10 C9 C11 116.18(17) . . ?
N2 C10 C9 179.4(2) . . ?
N1 C11 C9 176.0(2) . . ?
C8 C12 C14 122.42(19) . . ?
C8 C12 C13 121.16(17) . . ?
C14 C12 C13 116.34(19) . . ?
N3 C13 C12 178.1(2) . . ?
N4 C14 C12 176.7(4) . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_rb
_audit_block_doi                 10.5517/ccdc.csd.cc1kqyv2
_database_code_depnum_ccdc_archive 'CCDC 1452035'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.joc.6b01040 2016
_audit_update_record             
;
2016-02-06 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Rubidium 2-benzoyl-1,1,3,3-tetracyanopropenide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H5 N4 O Rb'
_chemical_formula_sum            'C14 H5 N4 O Rb'
_chemical_formula_weight         330.69

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'
Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   9.3706(12)
_cell_length_b                   17.767(5)
_cell_length_c                   8.5579(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.183(12)
_cell_angle_gamma                90.00
_cell_volume                     1361.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      14
_cell_measurement_theta_max      18

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    3.637
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.3561
_exptl_absorpt_correction_T_max  0.6464

_exptl_absorpt_process_details   
;
(See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometr'
_diffrn_measurement_method       'non-profiled omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            2904
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         26.97
_reflns_number_total             2904
_reflns_number_gt                1713
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement       'CAD-4 Software'
_computing_data_reduction        'XCAD-4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2000)'
_computing_publication_material  'WinGX (Farrugia, 1999)'


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0305P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2904
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Rb1 Rb 0.77317(4) 0.83618(2) 0.13125(5) 0.05432(17) Uani 1 1 d . . .
O1 O 0.4944(3) 1.09581(14) 0.0778(3) 0.0516(7) Uani 1 1 d . . .
N1 N 0.4831(4) 1.24517(19) 0.3401(5) 0.0698(11) Uani 1 1 d . . .
N2 N 1.0822(4) 1.20112(19) 0.1412(4) 0.0583(10) Uani 1 1 d . . .
N3 N 0.8790(4) 1.33203(19) 0.2345(4) 0.0630(10) Uani 1 1 d . . .
N4 N 0.8413(3) 0.9879(2) 0.0271(5) 0.0601(10) Uani 1 1 d . . .
C1 C 0.6133(4) 1.08980(19) 0.1840(4) 0.0350(8) Uani 1 1 d . . .
C2 C 0.7342(4) 1.14760(18) 0.1883(4) 0.0330(8) Uani 1 1 d . . .
C3 C 0.7124(4) 1.21888(19) 0.2436(4) 0.0374(9) Uani 1 1 d . . .
C4 C 0.8521(4) 1.1227(2) 0.1344(4) 0.0360(9) Uani 1 1 d . . .
C5 C 0.8485(4) 1.0480(2) 0.0738(5) 0.0415(9) Uani 1 1 d . . .
C6 C 0.9791(4) 1.1669(2) 0.1359(4) 0.0404(8) Uani 1 1 d . . .
C7 C 0.5852(4) 1.2335(2) 0.2973(5) 0.0469(10) Uani 1 1 d . . .
C8 C 0.8045(4) 1.2817(2) 0.2393(5) 0.0430(9) Uani 1 1 d . . .
C9 C 0.6432(4) 1.0303(2) 0.3094(4) 0.0355(8) Uani 1 1 d . . .
C10 C 0.5402(4) 0.9723(2) 0.2943(4) 0.0442(10) Uani 1 1 d . . .
H10 H 0.4547 0.9710 0.2050 0.053 Uiso 1 1 calc . . .
C11 C 0.5649(5) 0.9169(2) 0.4116(6) 0.0564(11) Uani 1 1 d . . .
H11 H 0.4963 0.8781 0.4009 0.068 Uiso 1 1 calc . . .
C12 C 0.6897(5) 0.9188(3) 0.5436(6) 0.0691(13) Uani 1 1 d . . .
H12 H 0.7061 0.8809 0.6220 0.083 Uiso 1 1 calc . . .
C13 C 0.7911(5) 0.9761(3) 0.5610(5) 0.0690(14) Uani 1 1 d . . .
H13 H 0.8747 0.9777 0.6524 0.083 Uiso 1 1 calc . . .
C14 C 0.7694(4) 1.0317(2) 0.4428(5) 0.0524(11) Uani 1 1 d . . .
H14 H 0.8396 1.0698 0.4532 0.063 Uiso 1 1 calc . . .


_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
Rb1 O1 2.881(2) 3_675 ?
Rb1 N1 2.965(3) 2_645 ?
Rb1 N4 2.967(4) . ?
Rb1 N2 3.095(3) 3_775 ?
Rb1 N3 3.121(3) 2_745 ?
Rb1 N2 3.135(3) 2_745 ?
Rb1 C6 3.708(3) 3_775 ?
Rb1 Rb1 5.2619(8) 4_575 ?
Rb1 Rb1 5.2619(8) 4_576 ?
O1 C1 1.216(4) . ?
O1 Rb1 2.881(2) 3_675 ?
N1 C7 1.140(4) . ?
N1 Rb1 2.965(3) 2_655 ?
N2 C6 1.131(4) . ?
N2 Rb1 3.095(3) 3_775 ?
N2 Rb1 3.135(3) 2_755 ?
N3 C8 1.142(4) . ?
N3 Rb1 3.121(3) 2_755 ?
N4 C5 1.135(4) . ?
C1 C9 1.474(5) . ?
C1 C2 1.522(4) . ?
C2 C4 1.388(4) . ?
C2 C3 1.388(4) . ?
C3 C8 1.418(5) . ?
C3 C7 1.422(5) . ?
C4 C6 1.422(5) . ?
C4 C5 1.423(5) . ?
C6 Rb1 3.708(3) 3_775 ?
C9 C14 1.380(5) . ?
C9 C10 1.391(5) . ?
C10 C11 1.375(5) . ?
C11 C12 1.365(6) . ?
C12 C13 1.371(6) . ?
C13 C14 1.385(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Rb1 N1 72.69(9) 3_675 2_645 ?
O1 Rb1 N4 69.96(8) 3_675 . ?
N1 Rb1 N4 140.51(9) 2_645 . ?
O1 Rb1 N2 96.69(8) 3_675 3_775 ?
N1 Rb1 N2 119.42(10) 2_645 3_775 ?
N4 Rb1 N2 77.71(9) . 3_775 ?
O1 Rb1 N3 149.49(8) 3_675 2_745 ?
N1 Rb1 N3 137.74(9) 2_645 2_745 ?
N4 Rb1 N3 80.68(9) . 2_745 ?
N2 Rb1 N3 68.29(9) 3_775 2_745 ?
O1 Rb1 N2 147.59(8) 3_675 2_745 ?
N1 Rb1 N2 75.13(9) 2_645 2_745 ?
N4 Rb1 N2 142.19(9) . 2_745 ?
N2 Rb1 N2 95.67(7) 3_775 2_745 ?
N3 Rb1 N2 62.63(9) 2_745 2_745 ?
O1 Rb1 C6 102.22(7) 3_675 3_775 ?
N1 Rb1 C6 135.46(9) 2_645 3_775 ?
N4 Rb1 C6 66.34(9) . 3_775 ?
N2 Rb1 C6 16.12(8) 3_775 3_775 ?
N3 Rb1 C6 56.68(9) 2_745 3_775 ?
N2 Rb1 C6 97.89(8) 2_745 3_775 ?
O1 Rb1 Rb1 87.02(5) 3_675 4_575 ?
N1 Rb1 Rb1 86.81(8) 2_645 4_575 ?
N4 Rb1 Rb1 103.45(7) . 4_575 ?
N2 Rb1 Rb1 32.61(6) 3_775 4_575 ?
N3 Rb1 Rb1 91.99(7) 2_745 4_575 ?
N2 Rb1 Rb1 87.47(7) 2_745 4_575 ?
C6 Rb1 Rb1 48.69(6) 3_775 4_575 ?
O1 Rb1 Rb1 122.69(5) 3_675 4_576 ?
N1 Rb1 Rb1 54.60(7) 2_645 4_576 ?
N4 Rb1 Rb1 145.56(7) . 4_576 ?
N2 Rb1 Rb1 126.38(7) 3_775 4_576 ?
N3 Rb1 Rb1 86.43(7) 2_745 4_576 ?
N2 Rb1 Rb1 32.14(6) 2_745 4_576 ?
C6 Rb1 Rb1 130.03(6) 3_775 4_576 ?
Rb1 Rb1 Rb1 108.82(2) 4_575 4_576 ?
C1 O1 Rb1 159.7(2) . 3_675 ?
C7 N1 Rb1 154.5(3) . 2_655 ?
C6 N2 Rb1 114.4(3) . 3_775 ?
C6 N2 Rb1 130.1(3) . 2_755 ?
Rb1 N2 Rb1 115.25(10) 3_775 2_755 ?
C8 N3 Rb1 126.0(3) . 2_755 ?
C5 N4 Rb1 138.1(3) . . ?
O1 C1 C9 122.8(3) . . ?
O1 C1 C2 118.0(3) . . ?
C9 C1 C2 119.1(3) . . ?
C4 C2 C3 128.0(3) . . ?
C4 C2 C1 115.9(3) . . ?
C3 C2 C1 116.1(3) . . ?
C2 C3 C8 123.9(3) . . ?
C2 C3 C7 119.9(3) . . ?
C8 C3 C7 116.0(3) . . ?
C2 C4 C6 124.6(3) . . ?
C2 C4 C5 118.9(3) . . ?
C6 C4 C5 116.6(3) . . ?
N4 C5 C4 177.6(4) . . ?
N2 C6 C4 178.1(4) . . ?
N2 C6 Rb1 49.5(2) . 3_775 ?
C4 C6 Rb1 131.4(2) . 3_775 ?
N1 C7 C3 179.9(5) . . ?
N3 C8 C3 179.3(4) . . ?
C14 C9 C10 119.4(3) . . ?
C14 C9 C1 121.5(3) . . ?
C10 C9 C1 119.1(3) . . ?
C11 C10 C9 119.9(3) . . ?
C12 C11 C10 120.4(4) . . ?
C11 C12 C13 120.3(4) . . ?
C12 C13 C14 120.2(4) . . ?
C9 C14 C13 119.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        26.97
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.069
_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# 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_YAK405
_database_code_depnum_ccdc_archive 'CCDC 1575022'
_audit_update_record             
;
2017-10-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H9 Br2 N8 O2.5 Rb2'
_chemical_formula_sum            'C28 H9 Br2 N8 O2.5 Rb2'
_chemical_formula_weight         828.17

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rb Rb -0.4688 1.6079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9306(3)
_cell_length_b                   10.2782(3)
_cell_length_c                   15.3731(4)
_cell_angle_alpha                107.505(3)
_cell_angle_beta                 92.216(2)
_cell_angle_gamma                95.179(2)
_cell_volume                     1486.76(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    854
_cell_measurement_theta_min      4
_cell_measurement_theta_max      55

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.850
_exptl_crystal_F_000             794
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .13
_exptl_absorpt_coefficient_mu    7.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  0.608

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            11756
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.482
_diffrn_reflns_theta_max         70.504
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5336
_reflns_number_gt                4602
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²+0.5575P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5336
_refine_ls_number_parameters     395
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Rb1 Rb 0.17035(4) 0.53199(4) 0.69876(3) 0.06214(15) Uani 1 1 d . . . . .
Rb2 Rb 0.46216(6) 0.94769(6) 0.81840(4) 0.08763(18) Uani 1 1 d . . . . .
Br1A Br 0.40603(7) 0.27230(5) 0.75793(4) 0.0894(2) Uani 1 1 d . . . . .
O1A O 0.7284(3) 0.8554(3) 1.0659(2) 0.0732(8) Uani 1 1 d . . . . .
N1A N 0.9218(5) 0.6057(5) 1.1573(3) 0.0895(12) Uani 1 1 d . . . . .
N2A N 1.2683(5) 0.7871(6) 1.0569(4) 0.1037(15) Uani 1 1 d . . . . .
N3A N 1.1845(4) 0.8101(4) 0.8493(3) 0.0711(9) Uani 1 1 d . . . . .
N4A N 0.7585(4) 0.8894(4) 0.8296(3) 0.0818(10) Uani 1 1 d . . . . .
C1A C 0.7710(4) 0.7636(4) 1.0070(2) 0.0550(8) Uani 1 1 d . . . . .
C2A C 0.6837(4) 0.6443(4) 0.9476(2) 0.0550(8) Uani 1 1 d . . . . .
C3A C 0.7400(4) 0.5350(4) 0.8874(3) 0.0595(9) Uani 1 1 d . . . . .
H3A H 0.8335 0.5371 0.8845 0.071 Uiso 1 1 calc R U . . .
C4A C 0.6564(5) 0.4247(4) 0.8325(3) 0.0664(10) Uani 1 1 d . . . . .
H4A H 0.6929 0.3508 0.7931 0.080 Uiso 1 1 calc R U . . .
C5A C 0.5184(5) 0.4245(4) 0.8364(3) 0.0638(9) Uani 1 1 d . . . . .
C6A C 0.4594(5) 0.5314(4) 0.8947(3) 0.0670(10) Uani 1 1 d . . . . .
H6A H 0.3656 0.5292 0.8959 0.080 Uiso 1 1 calc R U . . .
C7A C 0.5424(4) 0.6399(4) 0.9504(3) 0.0621(9) Uani 1 1 d . . . . .
H7A H 0.5047 0.7120 0.9907 0.074 Uiso 1 1 calc R U . . .
C8A C 0.9212(4) 0.7757(3) 0.9908(2) 0.0544(8) Uani 1 1 d . . . . .
C9A C 1.0094(4) 0.7366(4) 1.0484(3) 0.0625(9) Uani 1 1 d . . . . .
C10A C 0.9596(5) 0.6660(5) 1.1096(3) 0.0698(10) Uani 1 1 d . . . . .
C11A C 1.1532(5) 0.7625(5) 1.0512(3) 0.0740(11) Uani 1 1 d . . . . .
C12A C 0.9525(4) 0.8232(4) 0.9169(3) 0.0550(8) Uani 1 1 d . . . . .
C13A C 0.8467(4) 0.8611(4) 0.8676(3) 0.0621(9) Uani 1 1 d . . . . .
C14A C 1.0812(4) 0.8186(4) 0.8808(3) 0.0582(8) Uani 1 1 d . . . . .
Br1 Br 0.92255(5) 0.02037(5) 0.28835(4) 0.08116(18) Uani 1 1 d . . . . .
O1 O 1.1850(3) -0.3402(3) 0.5511(2) 0.0700(7) Uani 1 1 d . . . . .
N1 N 1.1074(4) -0.5903(4) 0.3135(3) 0.0879(12) Uani 1 1 d . . . . .
N2 N 1.5324(3) -0.6257(3) 0.3028(2) 0.0637(8) Uani 1 1 d . . . . .
N3 N 1.7189(4) -0.3444(4) 0.4592(3) 0.0734(9) Uani 1 1 d . . . . .
N4 N 1.4691(5) -0.0577(4) 0.6236(3) 0.0931(13) Uani 1 1 d . . . . .
C1 C 1.2284(3) -0.3091(3) 0.4869(2) 0.0499(7) Uani 1 1 d . . . . .
C2 C 1.1591(3) -0.2256(3) 0.4402(2) 0.0478(7) Uani 1 1 d . . . . .
C3 C 1.0219(4) -0.2117(4) 0.4527(2) 0.0541(8) Uani 1 1 d . . . . .
H3 H 0.9776 -0.2518 0.4920 0.065 Uiso 1 1 calc R U . . .
C4 C 0.9523(4) -0.1392(4) 0.4075(3) 0.0576(8) Uani 1 1 d . . . . .
H4 H 0.8606 -0.1315 0.4150 0.069 Uiso 1 1 calc R U . . .
C5 C 1.0190(4) -0.0784(4) 0.3513(3) 0.0563(8) Uani 1 1 d . . . . .
C6 C 1.1549(4) -0.0877(4) 0.3386(3) 0.0625(9) Uani 1 1 d . . . . .
H6 H 1.1989 -0.0440 0.3010 0.075 Uiso 1 1 calc R U . . .
C7 C 1.2246(4) -0.1629(4) 0.3825(3) 0.0563(8) Uani 1 1 d . . . . .
H7 H 1.3159 -0.1717 0.3735 0.068 Uiso 1 1 calc R U . . .
C8 C 1.3614(3) -0.3611(3) 0.4513(2) 0.0466(7) Uani 1 1 d . . . . .
C9 C 1.3461(3) -0.4840(3) 0.3799(2) 0.0484(7) Uani 1 1 d . . . . .
C10 C 1.2139(4) -0.5444(4) 0.3438(3) 0.0599(9) Uani 1 1 d . . . . .
C11 C 1.4530(4) -0.5594(3) 0.3389(2) 0.0505(7) Uani 1 1 d . . . . .
C12 C 1.4790(4) -0.2817(3) 0.4949(2) 0.0520(7) Uani 1 1 d . . . . .
C13 C 1.6110(4) -0.3173(4) 0.4744(2) 0.0553(8) Uani 1 1 d . . . . .
C14 C 1.4720(4) -0.1574(4) 0.5664(3) 0.0638(9) Uani 1 1 d . . . . .
O3 O 0.4397(12) 0.9642(11) 1.0063(9) 0.152(4) Uani 0.5 1 d D . P . .
H3B H 0.392(4) 1.018(4) 0.989(4) 0.182 Uiso 0.5 1 d D U P . .
H3C H 0.387(4) 0.899(3) 1.015(4) 0.182 Uiso 0.5 1 d D U P . .


_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
Rb1 N1 2.886(4) 2_656 ?
Rb1 N3 2.932(4) 2_756 ?
Rb1 O1 2.947(3) 1_465 ?
Rb1 N2 3.025(4) 2_756 ?
Rb1 N3A 3.078(4) 1_455 ?
Rb1 N1A 3.089(4) 2_667 ?
Rb1 C14A 3.605(4) 1_455 ?
Rb1 C3 3.717(4) 2_656 ?
Rb1 Br1A 3.9816(7) . ?
Rb1 Rb2 4.7603(7) . ?
Rb2 O3 2.684(12) 2_677 ?
Rb2 O3 2.860(12) . ?
Rb2 N4 2.982(5) 1_465 ?
Rb2 N4A 3.064(4) . ?
Rb2 O1A 3.102(3) 2_677 ?
Rb2 N3A 3.103(4) 1_455 ?
Rb2 N2 3.280(3) 2_756 ?
Rb2 N2A 3.662(6) 2_777 ?
Rb2 C14 3.703(4) 1_465 ?
Rb2 Br1A 3.8037(8) 1_565 ?
Rb2 Rb2 5.3680(10) 2_677 ?
Rb2 H3B 2.64(6) . ?
Br1A C5A 1.895(4) . ?
Br1A Rb2 3.8037(8) 1_545 ?
O1A C1A 1.216(4) . ?
O1A Rb2 3.102(3) 2_677 ?
N1A C10A 1.147(6) . ?
N1A Rb1 3.089(4) 2_667 ?
N2A C11A 1.142(6) . ?
N2A Rb2 3.662(6) 2_777 ?
N3A C14A 1.150(5) . ?
N3A Rb1 3.078(4) 1_655 ?
N3A Rb2 3.103(4) 1_655 ?
N4A C13A 1.141(6) . ?
C1A C2A 1.470(5) . ?
C1A C8A 1.522(5) . ?
C2A C3A 1.399(5) . ?
C2A C7A 1.403(6) . ?
C3A C4A 1.374(6) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.374(6) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.385(6) . ?
C6A C7A 1.364(6) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A C9A 1.390(6) . ?
C8A C12A 1.399(5) . ?
C9A C11A 1.425(6) . ?
C9A C10A 1.427(6) . ?
C12A C14A 1.413(6) . ?
C12A C13A 1.422(6) . ?
C14A Rb1 3.605(4) 1_655 ?
Br1 C5 1.892(4) . ?
O1 C1 1.208(4) . ?
O1 Rb1 2.947(3) 1_645 ?
N1 C10 1.140(5) . ?
N1 Rb1 2.886(4) 2_656 ?
N2 C11 1.138(5) . ?
N2 Rb1 3.025(3) 2_756 ?
N2 Rb2 3.280(3) 2_756 ?
N3 C13 1.146(5) . ?
N3 Rb1 2.932(4) 2_756 ?
N4 C14 1.136(6) . ?
N4 Rb2 2.982(5) 1_645 ?
C1 C2 1.471(5) . ?
C1 C8 1.529(5) . ?
C2 C7 1.392(5) . ?
C2 C3 1.397(5) . ?
C3 C4 1.373(5) . ?
C3 Rb1 3.717(4) 2_656 ?
C3 H3 0.9300 . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(6) . ?
C6 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C12 1.384(5) . ?
C8 C9 1.394(5) . ?
C9 C10 1.417(5) . ?
C9 C11 1.425(5) . ?
C12 C13 1.415(5) . ?
C12 C14 1.422(5) . ?
C14 Rb2 3.703(4) 1_645 ?
O3 O3 1.40(2) 2_677 ?
O3 Rb2 2.684(12) 2_677 ?
O3 H3B 0.8601(10) . ?
O3 H3C 0.8600(11) . ?

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
N1 Rb1 N3 119.72(11) 2_656 2_756 ?
N1 Rb1 O1 80.69(12) 2_656 1_465 ?
N3 Rb1 O1 71.17(10) 2_756 1_465 ?
N1 Rb1 N2 147.99(11) 2_656 2_756 ?
N3 Rb1 N2 71.35(10) 2_756 2_756 ?
O1 Rb1 N2 74.96(9) 1_465 2_756 ?
N1 Rb1 N3A 79.71(11) 2_656 1_455 ?
N3 Rb1 N3A 150.99(10) 2_756 1_455 ?
O1 Rb1 N3A 93.14(9) 1_465 1_455 ?
N2 Rb1 N3A 81.20(10) 2_756 1_455 ?
N1 Rb1 N1A 85.46(14) 2_656 2_667 ?
N3 Rb1 N1A 113.43(12) 2_756 2_667 ?
O1 Rb1 N1A 165.70(11) 1_465 2_667 ?
N2 Rb1 N1A 119.25(11) 2_756 2_667 ?
N3A Rb1 N1A 87.87(11) 1_455 2_667 ?
N1 Rb1 C14A 64.88(10) 2_656 1_455 ?
N3 Rb1 C14A 167.58(10) 2_756 1_455 ?
O1 Rb1 C14A 99.39(8) 1_465 1_455 ?
N2 Rb1 C14A 98.76(9) 2_756 1_455 ?
N3A Rb1 C14A 17.65(9) 1_455 1_455 ?
N1A Rb1 C14A 77.73(11) 2_667 1_455 ?
N1 Rb1 C3 73.84(10) 2_656 2_656 ?
N3 Rb1 C3 56.22(9) 2_756 2_656 ?
O1 Rb1 C3 92.76(9) 1_465 2_656 ?
N2 Rb1 C3 127.16(9) 2_756 2_656 ?
N3A Rb1 C3 151.55(9) 1_455 2_656 ?
N1A Rb1 C3 79.88(11) 2_667 2_656 ?
C14A Rb1 C3 134.07(9) 1_455 2_656 ?
N1 Rb1 Br1A 143.36(10) 2_656 . ?
N3 Rb1 Br1A 64.95(8) 2_756 . ?
O1 Rb1 Br1A 129.44(6) 1_465 . ?
N2 Rb1 Br1A 68.37(6) 2_756 . ?
N3A Rb1 Br1A 113.59(7) 1_455 . ?
N1A Rb1 Br1A 62.27(9) 2_667 . ?
C14A Rb1 Br1A 119.22(6) 1_455 . ?
C3 Rb1 Br1A 83.24(6) 2_656 . ?
N1 Rb1 Rb2 110.19(8) 2_656 . ?
N3 Rb1 Rb2 111.22(7) 2_756 . ?
O1 Rb1 Rb2 73.88(7) 1_465 . ?
N2 Rb1 Rb2 43.03(6) 2_756 . ?
N3A Rb1 Rb2 39.83(7) 1_455 . ?
N1A Rb1 Rb2 114.72(9) 2_667 . ?
C14A Rb1 Rb2 57.33(7) 1_455 . ?
C3 Rb1 Rb2 164.78(6) 2_656 . ?
Br1A Rb1 Rb2 99.457(13) . . ?
O3 Rb2 O3 29.0(4) 2_677 . ?
O3 Rb2 N4 152.3(3) 2_677 1_465 ?
O3 Rb2 N4 175.9(2) . 1_465 ?
O3 Rb2 N4A 70.6(3) 2_677 . ?
O3 Rb2 N4A 90.9(3) . . ?
N4 Rb2 N4A 92.87(13) 1_465 . ?
O3 Rb2 O1A 70.6(3) 2_677 2_677 ?
O3 Rb2 O1A 60.7(2) . 2_677 ?
N4 Rb2 O1A 115.34(11) 1_465 2_677 ?
N4A Rb2 O1A 138.23(11) . 2_677 ?
O3 Rb2 N3A 97.2(3) 2_677 1_455 ?
O3 Rb2 N3A 68.3(2) . 1_455 ?
N4 Rb2 N3A 109.75(12) 1_465 1_455 ?
N4A Rb2 N3A 135.95(11) . 1_455 ?
O1A Rb2 N3A 64.43(9) 2_677 1_455 ?
O3 Rb2 N2 120.2(2) 2_677 2_756 ?
O3 Rb2 N2 109.1(2) . 2_756 ?
N4 Rb2 N2 73.44(10) 1_465 2_756 ?
N4A Rb2 N2 74.10(11) . 2_756 ?
O1A Rb2 N2 141.15(9) 2_677 2_756 ?
N3A Rb2 N2 76.90(10) 1_455 2_756 ?
O3 Rb2 N2A 47.0(2) 2_677 2_777 ?
O3 Rb2 N2A 75.2(2) . 2_777 ?
N4 Rb2 N2A 105.50(12) 1_465 2_777 ?
N4A Rb2 N2A 57.91(12) . 2_777 ?
O1A Rb2 N2A 84.10(10) 2_677 2_777 ?
N3A Rb2 N2A 140.13(11) 1_455 2_777 ?
N2 Rb2 N2A 131.98(10) 2_756 2_777 ?
O3 Rb2 C14 157.3(3) 2_677 1_465 ?
O3 Rb2 C14 167.1(2) . 1_465 ?
N4 Rb2 C14 15.18(10) 1_465 1_465 ?
N4A Rb2 C14 88.19(11) . 1_465 ?
O1A Rb2 C14 126.39(9) 2_677 1_465 ?
N3A Rb2 C14 103.84(10) 1_455 1_465 ?
N2 Rb2 C14 58.27(9) 2_756 1_465 ?
N2A Rb2 C14 114.76(11) 2_777 1_465 ?
O3 Rb2 Br1A 105.0(2) 2_677 1_565 ?
O3 Rb2 Br1A 115.7(2) . 1_565 ?
N4 Rb2 Br1A 61.20(9) 1_465 1_565 ?
N4A Rb2 Br1A 115.12(8) . 1_565 ?
O1A Rb2 Br1A 61.79(6) 2_677 1_565 ?
N3A Rb2 Br1A 108.91(7) 1_455 1_565 ?
N2 Rb2 Br1A 133.68(6) 2_756 1_565 ?
N2A Rb2 Br1A 72.77(7) 2_777 1_565 ?
C14 Rb2 Br1A 76.19(7) 1_465 1_565 ?
O3 Rb2 Rb1 121.6(2) 2_677 . ?
O3 Rb2 Rb1 95.6(2) . . ?
N4 Rb2 Rb1 84.56(9) 1_465 . ?
N4A Rb2 Rb1 110.83(9) . . ?
O1A Rb2 Rb1 102.37(6) 2_677 . ?
N3A Rb2 Rb1 39.44(7) 1_455 . ?
N2 Rb2 Rb1 39.00(6) 2_756 . ?
N2A Rb2 Rb1 164.58(7) 2_777 . ?
C14 Rb2 Rb1 72.81(6) 1_465 . ?
Br1A Rb2 Rb1 122.637(16) 1_565 . ?
O3 Rb2 Rb2 15.0(2) 2_677 2_677 ?
O3 Rb2 Rb2 14.0(2) . 2_677 ?
N4 Rb2 Rb2 167.01(9) 1_465 2_677 ?
N4A Rb2 Rb2 80.93(9) . 2_677 ?
O1A Rb2 Rb2 64.72(6) 2_677 2_677 ?
N3A Rb2 Rb2 82.31(7) 1_455 2_677 ?
N2 Rb2 Rb2 115.21(6) 2_756 2_677 ?
N2A Rb2 Rb2 61.53(8) 2_777 2_677 ?
C14 Rb2 Rb2 168.73(7) 1_465 2_677 ?
Br1A Rb2 Rb2 111.096(18) 1_565 2_677 ?
Rb1 Rb2 Rb2 108.293(16) . 2_677 ?
O3 Rb2 H3B 36.4(9) 2_677 . ?
O3 Rb2 H3B 17.39(19) . . ?
N4 Rb2 H3B 158.6(3) 1_465 . ?
N4A Rb2 H3B 105.3(6) . . ?
O1A Rb2 H3B 43.3(3) 2_677 . ?
N3A Rb2 H3B 64.4(9) 1_455 . ?
N2 Rb2 H3B 121.9(7) 2_756 . ?
N2A Rb2 H3B 76.0(10) 2_777 . ?
C14 Rb2 H3B 166.1(8) 1_465 . ?
Br1A Rb2 H3B 100.1(4) 1_565 . ?
Rb1 Rb2 H3B 99.0(9) . . ?
Rb2 Rb2 H3B 24.4(6) 2_677 . ?
C5A Br1A Rb2 110.38(12) . 1_545 ?
C5A Br1A Rb1 88.97(13) . . ?
Rb2 Br1A Rb1 152.63(2) 1_545 . ?
C1A O1A Rb2 162.6(3) . 2_677 ?
C10A N1A Rb1 174.5(4) . 2_667 ?
C11A N2A Rb2 141.3(5) . 2_777 ?
C14A N3A Rb1 108.1(3) . 1_655 ?
C14A N3A Rb2 149.9(3) . 1_655 ?
Rb1 N3A Rb2 100.74(11) 1_655 1_655 ?
C13A N4A Rb2 149.9(4) . . ?
O1A C1A C2A 123.4(4) . . ?
O1A C1A C8A 118.4(3) . . ?
C2A C1A C8A 118.2(3) . . ?
C3A C2A C7A 119.4(4) . . ?
C3A C2A C1A 120.7(4) . . ?
C7A C2A C1A 119.9(3) . . ?
C4A C3A C2A 119.7(4) . . ?
C4A C3A H3A 120.2 . . ?
C2A C3A H3A 120.2 . . ?
C3A C4A C5A 119.4(4) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
C4A C5A C6A 122.4(4) . . ?
C4A C5A Br1A 118.2(3) . . ?
C6A C5A Br1A 119.3(3) . . ?
C7A C6A C5A 118.2(4) . . ?
C7A C6A H6A 120.9 . . ?
C5A C6A H6A 120.9 . . ?
C6A C7A C2A 120.9(4) . . ?
C6A C7A H7A 119.5 . . ?
C2A C7A H7A 119.5 . . ?
C9A C8A C12A 128.0(4) . . ?
C9A C8A C1A 117.4(3) . . ?
C12A C8A C1A 114.6(3) . . ?
C8A C9A C11A 123.6(4) . . ?
C8A C9A C10A 121.0(4) . . ?
C11A C9A C10A 115.3(4) . . ?
N1A C10A C9A 177.8(5) . . ?
N2A C11A C9A 177.2(6) . . ?
C8A C12A C14A 123.1(3) . . ?
C8A C12A C13A 119.1(4) . . ?
C14A C12A C13A 117.3(3) . . ?
N4A C13A C12A 177.5(4) . . ?
N3A C14A C12A 177.5(4) . . ?
N3A C14A Rb1 54.2(3) . 1_655 ?
C12A C14A Rb1 123.3(2) . 1_655 ?
C1 O1 Rb1 158.8(3) . 1_645 ?
C10 N1 Rb1 144.0(3) . 2_656 ?
C11 N2 Rb1 125.8(3) . 2_756 ?
C11 N2 Rb2 136.2(3) . 2_756 ?
Rb1 N2 Rb2 97.97(9) 2_756 2_756 ?
C13 N3 Rb1 132.5(3) . 2_756 ?
C14 N4 Rb2 121.4(4) . 1_645 ?
O1 C1 C2 123.6(3) . . ?
O1 C1 C8 118.3(3) . . ?
C2 C1 C8 118.2(3) . . ?
C7 C2 C3 119.1(3) . . ?
C7 C2 C1 122.3(3) . . ?
C3 C2 C1 118.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 Rb1 88.5(2) . 2_656 ?
C2 C3 Rb1 106.6(2) . 2_656 ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
Rb1 C3 H3 74.8 2_656 . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 Br1 119.4(3) . . ?
C6 C5 Br1 118.8(3) . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C12 C8 C9 129.3(3) . . ?
C12 C8 C1 116.1(3) . . ?
C9 C8 C1 114.6(3) . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 C11 126.0(3) . . ?
C10 C9 C11 114.9(3) . . ?
N1 C10 C9 178.1(5) . . ?
N2 C11 C9 175.7(4) . . ?
C8 C12 C13 124.0(3) . . ?
C8 C12 C14 120.3(3) . . ?
C13 C12 C14 115.7(3) . . ?
N3 C13 C12 178.8(4) . . ?
N4 C14 C12 178.6(5) . . ?
N4 C14 Rb2 43.4(3) . 1_645 ?
C12 C14 Rb2 136.7(3) . 1_645 ?
O3 O3 Rb2 82.5(10) 2_677 2_677 ?
O3 O3 Rb2 68.5(9) 2_677 . ?
Rb2 O3 Rb2 151.0(4) 2_677 . ?
O3 O3 H3B 92(4) 2_677 . ?
Rb2 O3 H3B 116(4) 2_677 . ?
Rb2 O3 H3B 66(4) . . ?
O3 O3 H3C 159(3) 2_677 . ?
Rb2 O3 H3C 93(4) 2_677 . ?
Rb2 O3 H3C 114(4) . . ?
H3B O3 H3C 109(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
Rb2 O1A C1A C2A -18.6(11) 2_677 . . . ?
Rb2 O1A C1A C8A 158.5(7) 2_677 . . . ?
O1A C1A C2A C3A -173.4(4) . . . . ?
C8A C1A C2A C3A 9.5(5) . . . . ?
O1A C1A C2A C7A 7.2(6) . . . . ?
C8A C1A C2A C7A -169.9(3) . . . . ?
C7A C2A C3A C4A -0.6(5) . . . . ?
C1A C2A C3A C4A -180.0(3) . . . . ?
C2A C3A C4A C5A 1.2(6) . . . . ?
C3A C4A C5A C6A -0.8(6) . . . . ?
C3A C4A C5A Br1A 178.7(3) . . . . ?
Rb2 Br1A C5A C4A 64.4(3) 1_545 . . . ?
Rb1 Br1A C5A C4A -135.4(3) . . . . ?
Rb2 Br1A C5A C6A -116.1(3) 1_545 . . . ?
Rb1 Br1A C5A C6A 44.1(3) . . . . ?
C4A C5A C6A C7A -0.3(6) . . . . ?
Br1A C5A C6A C7A -179.8(3) . . . . ?
C5A C6A C7A C2A 1.0(6) . . . . ?
C3A C2A C7A C6A -0.5(6) . . . . ?
C1A C2A C7A C6A 178.9(4) . . . . ?
O1A C1A C8A C9A 82.4(4) . . . . ?
C2A C1A C8A C9A -100.4(4) . . . . ?
O1A C1A C8A C12A -98.9(4) . . . . ?
C2A C1A C8A C12A 78.3(4) . . . . ?
C12A C8A C9A C11A 11.9(7) . . . . ?
C1A C8A C9A C11A -169.6(4) . . . . ?
C12A C8A C9A C10A -167.9(4) . . . . ?
C1A C8A C9A C10A 10.6(5) . . . . ?
C9A C8A C12A C14A 10.1(6) . . . . ?
C1A C8A C12A C14A -168.5(3) . . . . ?
C9A C8A C12A C13A -178.5(4) . . . . ?
C1A C8A C12A C13A 2.9(5) . . . . ?
Rb2 N3A C14A Rb1 163.2(7) 1_655 . . 1_655 ?
C8A C12A C14A Rb1 90.4(4) . . . 1_655 ?
C13A C12A C14A Rb1 -81.1(4) . . . 1_655 ?
Rb1 O1 C1 C2 178.3(5) 1_645 . . . ?
Rb1 O1 C1 C8 -0.6(10) 1_645 . . . ?
O1 C1 C2 C7 163.8(4) . . . . ?
C8 C1 C2 C7 -17.3(5) . . . . ?
O1 C1 C2 C3 -17.7(5) . . . . ?
C8 C1 C2 C3 161.2(3) . . . . ?
C7 C2 C3 C4 1.1(5) . . . . ?
C1 C2 C3 C4 -177.4(3) . . . . ?
C7 C2 C3 Rb1 99.4(3) . . . 2_656 ?
C1 C2 C3 Rb1 -79.2(3) . . . 2_656 ?
C2 C3 C4 C5 -1.2(6) . . . . ?
Rb1 C3 C4 C5 -109.7(3) 2_656 . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C3 C4 C5 Br1 179.6(3) . . . . ?
C4 C5 C6 C7 1.3(6) . . . . ?
Br1 C5 C6 C7 -178.3(3) . . . . ?
C5 C6 C7 C2 -1.4(6) . . . . ?
C3 C2 C7 C6 0.2(5) . . . . ?
C1 C2 C7 C6 178.7(3) . . . . ?
O1 C1 C8 C12 -85.7(4) . . . . ?
C2 C1 C8 C12 95.3(4) . . . . ?
O1 C1 C8 C9 93.3(4) . . . . ?
C2 C1 C8 C9 -85.7(4) . . . . ?
C12 C8 C9 C10 -177.6(3) . . . . ?
C1 C8 C9 C10 3.5(5) . . . . ?
C12 C8 C9 C11 3.6(6) . . . . ?
C1 C8 C9 C11 -175.2(3) . . . . ?
C9 C8 C12 C13 -2.2(6) . . . . ?
C1 C8 C12 C13 176.6(3) . . . . ?
C9 C8 C12 C14 179.3(4) . . . . ?
C1 C8 C12 C14 -1.9(5) . . . . ?
C8 C12 C14 Rb2 90.6(4) . . . 1_645 ?
C13 C12 C14 Rb2 -88.0(4) . . . 1_645 ?

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 H3C N2A 0.8600(11) 1.839(14) 2.685(11) 168(5) 1_455
O3 H3B O1A 0.8601(10) 2.159(12) 3.018(11) 176(6) 2_677

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.092

