# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_20151017YKDSC_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1495747'
_audit_update_record             
;
2016-08-01 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'isoliquiritigenin-isonicotinamide cocrystal'
_chemical_name_common            ?
_chemical_melting_point          459
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N2 O5'
_chemical_formula_weight         378.37

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'

_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                   6.9223(13)
_cell_length_b                   8.2857(16)
_cell_length_c                   16.275(3)
_cell_angle_alpha                79.871(5)
_cell_angle_beta                 78.545(4)
_cell_angle_gamma                82.818(5)
_cell_volume                     896.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      71.24

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5564
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3282
_reflns_number_gt                1990
_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)+(0.0863P)²+0.5897P] 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         3282
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2000
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
C1 C 0.4970(5) 0.1342(4) 0.5910(2) 0.0410(9) Uani 1 1 d . . . . .
C2 C 0.3454(5) 0.1719(4) 0.5457(2) 0.0415(9) Uani 1 1 d . . . . .
H2 H 0.2235 0.1314 0.5683 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3717(5) 0.2691(5) 0.4672(2) 0.0397(9) Uani 1 1 d . . . . .
C4 C 0.5544(5) 0.3361(4) 0.43198(19) 0.0354(8) Uani 1 1 d . . . . .
C5 C 0.7039(5) 0.2979(4) 0.4805(2) 0.0430(9) Uani 1 1 d . . . . .
H5 H 0.8251 0.3408 0.4596 0.052 Uiso 1 1 calc R U . . .
C6 C 0.6773(5) 0.1992(5) 0.5579(2) 0.0479(10) Uani 1 1 d . . . . .
H6 H 0.7801 0.1754 0.5885 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5821(5) 0.4342(4) 0.3481(2) 0.0388(9) Uani 1 1 d . . . . .
C8 C 0.7588(5) 0.5205(4) 0.3146(2) 0.0391(9) Uani 1 1 d . . . . .
H8 H 0.8515 0.5156 0.3495 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7950(5) 0.6062(4) 0.2365(2) 0.0391(9) Uani 1 1 d . . . . .
H9 H 0.7010 0.6083 0.2026 0.047 Uiso 1 1 calc R U . . .
C10 C 0.9670(5) 0.6969(4) 0.1990(2) 0.0369(8) Uani 1 1 d . . . . .
C11 C 0.9955(5) 0.7662(5) 0.1134(2) 0.0505(10) Uani 1 1 d . . . . .
H11 H 0.9027 0.7556 0.0809 0.061 Uiso 1 1 calc R U . . .
C12 C 1.1592(6) 0.8504(5) 0.0758(2) 0.0604(12) Uani 1 1 d . . . . .
H12 H 1.1763 0.8954 0.0186 0.072 Uiso 1 1 calc R U . . .
C13 C 1.2959(6) 0.8671(5) 0.1235(2) 0.0529(11) Uani 1 1 d . . . . .
C14 C 1.2702(6) 0.8021(5) 0.2087(2) 0.0518(10) Uani 1 1 d . . . . .
H14 H 1.3619 0.8155 0.2411 0.062 Uiso 1 1 calc R U . . .
C15 C 1.1079(5) 0.7173(4) 0.2453(2) 0.0442(9) Uani 1 1 d . . . . .
H15 H 1.0923 0.6725 0.3025 0.053 Uiso 1 1 calc R U . . .
C16 C 1.1777(5) 0.8190(5) 0.8165(2) 0.0492(10) Uani 1 1 d . . . . .
H16 H 1.2937 0.8334 0.8339 0.059 Uiso 1 1 calc R U . . .
C17 C 1.0394(5) 0.7319(5) 0.8733(2) 0.0471(10) Uani 1 1 d . . . . .
H17 H 1.0633 0.6860 0.9272 0.056 Uiso 1 1 calc R U . . .
C18 C 0.8633(5) 0.7131(4) 0.8493(2) 0.0372(8) Uani 1 1 d . . . . .
C19 C 0.8391(5) 0.7794(4) 0.7681(2) 0.0435(9) Uani 1 1 d . . . . .
H19 H 0.7240 0.7680 0.7491 0.052 Uiso 1 1 calc R U . . .
C20 C 0.9881(5) 0.8632(4) 0.7149(2) 0.0468(10) Uani 1 1 d . . . . .
H20 H 0.9702 0.9073 0.6600 0.056 Uiso 1 1 calc R U . . .
C21 C 0.7083(5) 0.6239(5) 0.9142(2) 0.0433(9) Uani 1 1 d . . . . .
N1 N 1.1550(4) 0.8839(4) 0.73792(18) 0.0448(8) Uani 1 1 d . . . . .
N2 N 0.5755(4) 0.5599(4) 0.88459(17) 0.0495(9) Uani 1 1 d . . . . .
H2A H 0.4825 0.5105 0.9192 0.059 Uiso 1 1 calc R U . . .
H2B H 0.5820 0.5678 0.8307 0.059 Uiso 1 1 calc R U . . .
O1 O 0.4814(4) 0.0357(4) 0.66699(15) 0.0570(8) Uani 1 1 d . . . . .
H1 H 0.3726 -0.0005 0.6792 0.086 Uiso 1 1 calc R U . . .
O2 O 0.4511(4) 0.4458(4) 0.30256(16) 0.0605(8) Uani 1 1 d . . . . .
O3 O 0.2177(4) 0.2992(4) 0.42588(17) 0.0699(9) Uani 1 1 d . . . . .
H3 H 0.2495 0.3574 0.3801 0.105 Uiso 1 1 calc R U . . .
O4 O 1.4592(5) 0.9503(5) 0.0878(2) 0.0912(12) Uani 1 1 d . . . . .
H4 H 1.5183 0.9614 0.1251 0.137 Uiso 1 1 calc R U . . .
O5 O 0.7090(4) 0.6178(4) 0.98975(15) 0.0759(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.350(4) . ?
C1 C2 1.373(5) . ?
C1 C6 1.391(5) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 O3 1.346(4) . ?
C3 C4 1.418(4) . ?
C4 C5 1.396(5) . ?
C4 C7 1.452(4) . ?
C5 C6 1.368(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.264(4) . ?
C7 C8 1.457(4) . ?
C8 C9 1.335(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.459(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.387(5) . ?
C10 C11 1.395(4) . ?
C11 C12 1.385(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(5) . ?
C12 H12 0.9300 . ?
C13 O4 1.372(4) . ?
C13 C14 1.381(5) . ?
C14 C15 1.377(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.330(4) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(5) . ?
C18 C21 1.512(4) . ?
C19 C20 1.381(5) . ?
C19 H19 0.9300 . ?
C20 N1 1.322(4) . ?
C20 H20 0.9300 . ?
C21 O5 1.223(4) . ?
C21 N2 1.321(4) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
O1 H1 0.8200 . ?
O3 H3 0.8200 . ?
O4 H4 0.8200 . ?

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 C2 123.3(3) . . ?
O1 C1 C6 117.3(3) . . ?
C2 C1 C6 119.4(3) . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
O3 C3 C2 117.6(3) . . ?
O3 C3 C4 121.5(3) . . ?
C2 C3 C4 120.9(3) . . ?
C5 C4 C3 116.8(3) . . ?
C5 C4 C7 122.9(3) . . ?
C3 C4 C7 120.3(3) . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O2 C7 C4 119.9(3) . . ?
O2 C7 C8 118.8(3) . . ?
C4 C7 C8 121.3(3) . . ?
C9 C8 C7 123.5(3) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C8 C9 C10 126.6(3) . . ?
C8 C9 H9 116.7 . . ?
C10 C9 H9 116.7 . . ?
C15 C10 C11 117.4(3) . . ?
C15 C10 C9 122.5(3) . . ?
C11 C10 C9 120.1(3) . . ?
C12 C11 C10 121.3(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 O4 120.7(3) . . ?
C12 C13 C14 120.5(3) . . ?
O4 C13 C14 118.9(4) . . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C10 121.7(3) . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?
N1 C16 C17 123.5(3) . . ?
N1 C16 H16 118.3 . . ?
C17 C16 H16 118.3 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 117.7(3) . . ?
C19 C18 C21 123.9(3) . . ?
C17 C18 C21 118.3(3) . . ?
C18 C19 C20 119.1(3) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
N1 C20 C19 123.4(3) . . ?
N1 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?
O5 C21 N2 123.8(3) . . ?
O5 C21 C18 119.4(3) . . ?
N2 C21 C18 116.8(3) . . ?
C20 N1 C16 117.2(3) . . ?
C21 N2 H2A 120.0 . . ?
C21 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 O1 H1 109.5 . . ?
C3 O3 H3 109.5 . . ?
C13 O4 H4 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
O1 C1 C2 C3 -178.0(4) . . . . ?
C6 C1 C2 C3 1.9(6) . . . . ?
C1 C2 C3 O3 179.1(3) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
O3 C3 C4 C5 179.5(4) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
O3 C3 C4 C7 -2.6(6) . . . . ?
C2 C3 C4 C7 178.2(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C7 C4 C5 C6 -177.1(4) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
O1 C1 C6 C5 179.0(4) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
C5 C4 C7 O2 170.3(3) . . . . ?
C3 C4 C7 O2 -7.4(5) . . . . ?
C5 C4 C7 C8 -9.6(6) . . . . ?
C3 C4 C7 C8 172.6(3) . . . . ?
O2 C7 C8 C9 -3.0(6) . . . . ?
C4 C7 C8 C9 177.0(3) . . . . ?
C7 C8 C9 C10 179.3(3) . . . . ?
C8 C9 C10 C15 -6.5(6) . . . . ?
C8 C9 C10 C11 173.0(4) . . . . ?
C15 C10 C11 C12 0.7(6) . . . . ?
C9 C10 C11 C12 -178.8(4) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C11 C12 C13 O4 -179.9(4) . . . . ?
C11 C12 C13 C14 -0.7(7) . . . . ?
C12 C13 C14 C15 1.3(6) . . . . ?
O4 C13 C14 C15 -179.5(4) . . . . ?
C13 C14 C15 C10 -0.9(6) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
C9 C10 C15 C14 179.4(4) . . . . ?
N1 C16 C17 C18 -1.8(6) . . . . ?
C16 C17 C18 C19 2.0(6) . . . . ?
C16 C17 C18 C21 -177.0(4) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C21 C18 C19 C20 177.9(3) . . . . ?
C18 C19 C20 N1 -0.1(6) . . . . ?
C19 C18 C21 O5 -155.5(4) . . . . ?
C17 C18 C21 O5 23.5(6) . . . . ?
C19 C18 C21 N2 22.9(6) . . . . ?
C17 C18 C21 N2 -158.2(4) . . . . ?
C19 C20 N1 C16 0.4(6) . . . . ?
C17 C16 N1 C20 0.6(6) . . . . ?

_refine_diff_density_max         0.431
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_20151029ykdc_0m
_database_code_depnum_ccdc_archive 'CCDC 1495748'
_audit_update_record             
;
2016-09-28 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'isoliquiritigenin-nicotinamide cocrystal'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N2 O5'
_chemical_formula_weight         378.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   21.909(6)
_cell_length_b                   3.7898(13)
_cell_length_c                   23.918(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.968(8)
_cell_angle_gamma                90
_cell_volume                     1800.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2362
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.2

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6927
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.051
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3086
_reflns_number_gt                2260
_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)+18.0812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3086
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1738
_refine_ls_R_factor_gt           0.1314
_refine_ls_wR_factor_ref         0.2442
_refine_ls_wR_factor_gt          0.2294
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_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
C1 C 0.7492(3) 1.0100(17) 0.1026(2) 0.0262(14) Uani 1 1 d . . . . .
C2 C 0.6898(3) 1.0284(17) 0.0496(2) 0.0283(14) Uani 1 1 d . . . . .
H2 H 0.6897 1.1209 0.0135 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6307(3) 0.9092(17) 0.0504(3) 0.0294(15) Uani 1 1 d . . . . .
H3 H 0.5910 0.9209 0.0145 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6289(2) 0.7718(16) 0.1037(2) 0.0238(13) Uani 1 1 d . . . . .
C5 C 0.6899(3) 0.7490(18) 0.1568(3) 0.0323(16) Uani 1 1 d . . . . .
H5 H 0.6902 0.6540 0.1927 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7499(3) 0.866(2) 0.1564(3) 0.0371(18) Uani 1 1 d . . . . .
H6 H 0.7901 0.8482 0.1917 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5653(2) 0.6529(16) 0.1030(3) 0.0261(14) Uani 1 1 d . . . . .
H7 H 0.5273 0.6780 0.0660 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5557(3) 0.5111(16) 0.1500(2) 0.0265(14) Uani 1 1 d . . . . .
H8 H 0.5926 0.4828 0.1878 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4889(3) 0.3985(16) 0.1440(2) 0.0235(13) Uani 1 1 d . . . . .
C10 C 0.4826(2) 0.2415(15) 0.1978(2) 0.0196(12) Uani 1 1 d . . . . .
C11 C 0.5364(2) 0.1997(16) 0.2560(2) 0.0228(13) Uani 1 1 d . . . . .
H11 H 0.5793 0.2695 0.2615 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5278(2) 0.0587(16) 0.3051(2) 0.0244(14) Uani 1 1 d . . . . .
H12 H 0.5644 0.0358 0.3432 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4637(2) -0.0507(14) 0.2978(2) 0.0164(11) Uani 1 1 d . . . . .
C14 C 0.4100(2) -0.0124(16) 0.2411(2) 0.0205(13) Uani 1 1 d . . . . .
H14 H 0.3674 -0.0852 0.2358 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4185(2) 0.1328(14) 0.1916(2) 0.0174(12) Uani 1 1 d . . . . .
C16 C 0.1997(3) 0.5698(15) 0.0508(2) 0.0225(13) Uani 1 1 d . . . . .
H16 H 0.2438 0.6498 0.0709 0.027 Uiso 1 1 calc R U . . .
C17 C 0.1676(2) 0.4571(14) 0.0866(2) 0.0141(11) Uani 1 1 d . . . . .
C18 C 0.1017(2) 0.3334(15) 0.0561(2) 0.0180(12) Uani 1 1 d . . . . .
H18 H 0.0777 0.2615 0.0783 0.022 Uiso 1 1 calc R U . . .
C19 C 0.0727(2) 0.3200(15) -0.0072(2) 0.0209(13) Uani 1 1 d . . . . .
H19 H 0.0296 0.2294 -0.0285 0.025 Uiso 1 1 calc R U . . .
C20 C 0.1087(3) 0.4431(16) -0.0388(2) 0.0232(13) Uani 1 1 d . . . . .
H20 H 0.0883 0.4364 -0.0817 0.028 Uiso 1 1 calc R U . . .
C21 C 0.2007(2) 0.4731(14) 0.1556(2) 0.0168(11) Uani 1 1 d . . . . .
N1 N 0.2673(2) 0.4281(15) 0.18293(19) 0.0275(12) Uani 1 1 d . . . . .
H1A H 0.2788 0.3493 0.2211 0.041 Uiso 1 1 d R U . . .
H1C H 0.2792 0.2702 0.1618 0.041 Uiso 1 1 d R U . . .
N2 N 0.1714(2) 0.5711(14) -0.01108(19) 0.0242(11) Uani 1 1 d . . . . .
O1 O 0.80986(17) 1.1213(13) 0.10568(17) 0.0346(11) Uani 1 1 d . . . . .
H1 H 0.8041 1.2265 0.0739 0.052 Uiso 1 1 calc R U . . .
O2 O 0.43840(18) 0.4350(12) 0.09409(16) 0.0318(11) Uani 1 1 d . . . . .
O3 O 0.36319(17) 0.1644(12) 0.13675(16) 0.0284(10) Uani 1 1 d . . . . .
H3A H 0.3733 0.2728 0.1122 0.043 Uiso 1 1 calc R U . . .
O4 O 0.45830(17) -0.1843(12) 0.34818(16) 0.0269(10) Uani 1 1 d . . . . .
H4 H 0.4202 -0.2615 0.3382 0.040 Uiso 1 1 calc R U . . .
O5 O 0.16690(16) 0.5328(12) 0.18525(16) 0.0287(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.367(6) . ?
C1 C2 1.382(7) . ?
C1 C6 1.393(8) . ?
C2 C3 1.380(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(7) . ?
C4 C7 1.456(7) . ?
C5 C6 1.390(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.340(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.473(7) . ?
C8 H8 0.9300 . ?
C9 O2 1.246(6) . ?
C9 C10 1.475(8) . ?
C10 C11 1.403(7) . ?
C10 C15 1.410(7) . ?
C11 C12 1.376(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.402(7) . ?
C12 H12 0.9300 . ?
C13 O4 1.357(6) . ?
C13 C14 1.378(6) . ?
C14 C15 1.386(7) . ?
C14 H14 0.9300 . ?
C15 O3 1.365(6) . ?
C16 N2 1.341(6) . ?
C16 C17 1.385(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(7) . ?
C17 C21 1.500(7) . ?
C18 C19 1.374(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(8) . ?
C19 H19 0.9300 . ?
C20 N2 1.338(7) . ?
C20 H20 0.9300 . ?
C21 O5 1.243(6) . ?
C21 N1 1.334(6) . ?
N1 H1A 0.8900 . ?
N1 H1C 0.8900 . ?
O1 H1 0.8200 . ?
O3 H3A 0.8200 . ?
O4 H4 0.8200 . ?

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 C2 123.5(5) . . ?
O1 C1 C6 116.1(4) . . ?
C2 C1 C6 120.4(5) . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.7(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 117.7(5) . . ?
C3 C4 C7 120.1(5) . . ?
C5 C4 C7 122.2(5) . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.3(5) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C8 C7 C4 127.0(5) . . ?
C8 C7 H7 116.5 . . ?
C4 C7 H7 116.5 . . ?
C7 C8 C9 122.4(5) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
O2 C9 C8 120.3(5) . . ?
O2 C9 C10 120.6(5) . . ?
C8 C9 C10 119.1(4) . . ?
C11 C10 C15 117.0(5) . . ?
C11 C10 C9 124.1(5) . . ?
C15 C10 C9 118.9(4) . . ?
C12 C11 C10 122.0(5) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
O4 C13 C14 123.8(4) . . ?
O4 C13 C12 117.2(4) . . ?
C14 C13 C12 118.9(5) . . ?
C13 C14 C15 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
O3 C15 C14 118.1(4) . . ?
O3 C15 C10 121.0(5) . . ?
C14 C15 C10 120.9(4) . . ?
N2 C16 C17 124.3(5) . . ?
N2 C16 H16 117.9 . . ?
C17 C16 H16 117.9 . . ?
C16 C17 C18 117.7(4) . . ?
C16 C17 C21 122.2(4) . . ?
C18 C17 C21 120.0(4) . . ?
C19 C18 C17 118.7(5) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 119.1(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
N2 C20 C19 123.6(5) . . ?
N2 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
O5 C21 N1 122.4(5) . . ?
O5 C21 C17 120.5(4) . . ?
N1 C21 C17 117.0(4) . . ?
C21 N1 H1A 108.8 . . ?
C21 N1 H1C 109.2 . . ?
H1A N1 H1C 109.5 . . ?
C20 N2 C16 116.5(5) . . ?
C1 O1 H1 109.5 . . ?
C15 O3 H3A 109.5 . . ?
C13 O4 H4 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
O1 C1 C2 C3 179.8(6) . . . . ?
C6 C1 C2 C3 1.2(10) . . . . ?
C1 C2 C3 C4 0.5(10) . . . . ?
C2 C3 C4 C5 -1.7(9) . . . . ?
C2 C3 C4 C7 179.2(6) . . . . ?
C3 C4 C5 C6 1.2(10) . . . . ?
C7 C4 C5 C6 -179.7(6) . . . . ?
C4 C5 C6 C1 0.4(10) . . . . ?
O1 C1 C6 C5 179.6(6) . . . . ?
C2 C1 C6 C5 -1.6(10) . . . . ?
C3 C4 C7 C8 179.0(6) . . . . ?
C5 C4 C7 C8 -0.1(10) . . . . ?
C4 C7 C8 C9 -179.8(6) . . . . ?
C7 C8 C9 O2 -0.4(9) . . . . ?
C7 C8 C9 C10 179.4(6) . . . . ?
O2 C9 C10 C11 -178.2(6) . . . . ?
C8 C9 C10 C11 1.9(8) . . . . ?
O2 C9 C10 C15 0.1(8) . . . . ?
C8 C9 C10 C15 -179.7(5) . . . . ?
C15 C10 C11 C12 0.1(8) . . . . ?
C9 C10 C11 C12 178.5(6) . . . . ?
C10 C11 C12 C13 0.4(9) . . . . ?
C11 C12 C13 O4 -179.4(5) . . . . ?
C11 C12 C13 C14 -0.4(9) . . . . ?
O4 C13 C14 C15 178.7(5) . . . . ?
C12 C13 C14 C15 -0.3(9) . . . . ?
C13 C14 C15 O3 -179.7(5) . . . . ?
C13 C14 C15 C10 0.8(8) . . . . ?
C11 C10 C15 O3 179.8(5) . . . . ?
C9 C10 C15 O3 1.3(8) . . . . ?
C11 C10 C15 C14 -0.8(8) . . . . ?
C9 C10 C15 C14 -179.3(5) . . . . ?
N2 C16 C17 C18 0.7(9) . . . . ?
N2 C16 C17 C21 -177.7(5) . . . . ?
C16 C17 C18 C19 1.9(8) . . . . ?
C21 C17 C18 C19 -179.7(5) . . . . ?
C17 C18 C19 C20 -2.7(8) . . . . ?
C18 C19 C20 N2 1.2(9) . . . . ?
C16 C17 C21 O5 146.2(5) . . . . ?
C18 C17 C21 O5 -32.2(8) . . . . ?
C16 C17 C21 N1 -32.4(8) . . . . ?
C18 C17 C21 N1 149.2(5) . . . . ?
C19 C20 N2 C16 1.3(9) . . . . ?
C17 C16 N2 C20 -2.2(9) . . . . ?


_refine_diff_density_max         0.464
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.096

