# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_9-methyl-3-122-tricyanovinyl-9H-carbazole
_database_code_depnum_ccdc_archive 'CCDC 1517415'
_audit_update_record             
;
2016-11-15 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 N4'
_chemical_formula_weight         282.30

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'

_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                   8.0644(5)
_cell_length_b                   25.5256(13)
_cell_length_c                   7.0058(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.253(2)
_cell_angle_gamma                90
_cell_volume                     1369.57(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4567
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.32

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5571
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12529
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.660
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2783
_reflns_number_gt                2183
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0623P)²+0.8740P]
 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         2783
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
N1 N 0.1891(3) 0.60654(7) 0.4629(3) 0.0283(5) Uani 1 1 d . . . . .
N2 N 0.7161(2) 0.66882(7) 0.6184(3) 0.0245(4) Uani 1 1 d . . . . .
N3 N 0.3373(2) 0.35076(6) 0.8793(3) 0.0176(4) Uani 1 1 d . . . . .
N4 N 0.9314(3) 0.54727(7) 0.8493(3) 0.0329(5) Uani 1 1 d . . . . .
C1 C 0.6925(3) 0.26008(8) 1.1521(3) 0.0230(5) Uani 1 1 d . . . . .
H1 H 0.7149 0.2259 1.2084 0.028 Uiso 1 1 calc R U . . .
C2 C 0.8330(3) 0.29352(8) 1.1657(3) 0.0224(5) Uani 1 1 d . . . . .
H2 H 0.9486 0.2819 1.2323 0.027 Uiso 1 1 calc R U . . .
C3 C 0.8061(3) 0.34343(8) 1.0833(3) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.9019 0.3660 1.0917 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6348(3) 0.35976(7) 0.9876(3) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.5560(3) 0.40804(7) 0.8916(3) 0.0157(4) Uani 1 1 d . . . . .
C6 C 0.6244(3) 0.45572(7) 0.8587(3) 0.0170(4) Uani 1 1 d . . . . .
H6 H 0.7472 0.4611 0.9020 0.020 Uiso 1 1 calc R U . . .
C7 C 0.5110(3) 0.49623(7) 0.7605(3) 0.0173(4) Uani 1 1 d . . . . .
C8 C 0.5907(3) 0.54518(8) 0.7286(3) 0.0192(5) Uani 1 1 d . . . . .
C9 C 0.5167(3) 0.59094(8) 0.6385(3) 0.0196(5) Uani 1 1 d . . . . .
C10 C 0.3333(3) 0.59875(8) 0.5442(3) 0.0203(5) Uani 1 1 d . . . . .
C11 C 0.6281(3) 0.63427(8) 0.6274(3) 0.0195(5) Uani 1 1 d . . . . .
C12 C 0.5214(3) 0.27539(8) 1.0586(3) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.4262 0.2527 1.0508 0.023 Uiso 1 1 calc R U . . .
C13 C 0.4951(3) 0.32557(7) 0.9766(3) 0.0162(4) Uani 1 1 d . . . . .
C14 C 0.3720(3) 0.40032(7) 0.8273(3) 0.0167(4) Uani 1 1 d . . . . .
C15 C 0.2570(3) 0.44017(8) 0.7304(3) 0.0198(4) Uani 1 1 d . . . . .
H15 H 0.1342 0.4348 0.6866 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3278(3) 0.48753(8) 0.7006(3) 0.0195(4) Uani 1 1 d . . . . .
H16 H 0.2514 0.5152 0.6380 0.023 Uiso 1 1 calc R U . . .
C17 C 0.1659(3) 0.32589(8) 0.8288(3) 0.0248(5) Uani 1 1 d . . . . .
H17A H 0.0747 0.3525 0.7817 0.037 Uiso 1 1 calc R U . . .
H17B H 0.1532 0.3085 0.9483 0.037 Uiso 1 1 calc R U . . .
H17C H 0.1547 0.2999 0.7226 0.037 Uiso 1 1 calc R U . . .
C18 C 0.7828(3) 0.54640(7) 0.7981(3) 0.0215(5) 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
N1 C10 1.141(3) . ?
N2 C11 1.146(3) . ?
N3 C14 1.370(2) . ?
N3 C13 1.398(3) . ?
N3 C17 1.460(3) . ?
N4 C18 1.138(3) . ?
C1 C12 1.386(3) . ?
C1 C2 1.398(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9500 . ?
C4 C13 1.408(3) . ?
C4 C5 1.452(3) . ?
C5 C6 1.385(3) . ?
C5 C14 1.423(3) . ?
C6 C7 1.409(3) . ?
C6 H6 0.9500 . ?
C7 C16 1.421(3) . ?
C7 C8 1.454(3) . ?
C8 C9 1.372(3) . ?
C8 C18 1.471(3) . ?
C9 C10 1.432(3) . ?
C9 C11 1.443(3) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.401(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N3 C13 108.90(16) . . ?
C14 N3 C17 126.44(17) . . ?
C13 N3 C17 124.49(16) . . ?
C12 C1 C2 121.74(19) . . ?
C12 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 118.42(19) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C3 C4 C13 119.69(18) . . ?
C3 C4 C5 134.36(18) . . ?
C13 C4 C5 105.92(17) . . ?
C6 C5 C14 119.95(18) . . ?
C6 C5 C4 133.13(19) . . ?
C14 C5 C4 106.91(16) . . ?
C5 C6 C7 119.64(19) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C16 119.04(18) . . ?
C6 C7 C8 117.06(18) . . ?
C16 C7 C8 123.90(18) . . ?
C9 C8 C7 130.73(19) . . ?
C9 C8 C18 113.29(18) . . ?
C7 C8 C18 115.96(17) . . ?
C8 C9 C10 124.62(19) . . ?
C8 C9 C11 119.26(18) . . ?
C10 C9 C11 116.06(18) . . ?
N1 C10 C9 176.8(2) . . ?
N2 C11 C9 179.7(2) . . ?
C1 C12 C13 117.05(18) . . ?
C1 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C12 C13 N3 128.45(18) . . ?
C12 C13 C4 122.13(19) . . ?
N3 C13 C4 109.40(17) . . ?
N3 C14 C15 129.81(18) . . ?
N3 C14 C5 108.87(17) . . ?
C15 C14 C5 121.31(18) . . ?
C16 C15 C14 117.82(19) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C7 122.21(19) . . ?
C15 C16 H16 118.9 . . ?
C7 C16 H16 118.9 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 C8 179.1(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
C12 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C13 -0.2(3) . . . . ?
C2 C3 C4 C5 177.8(2) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C13 C4 C5 C6 179.0(2) . . . . ?
C3 C4 C5 C14 -178.3(2) . . . . ?
C13 C4 C5 C14 -0.1(2) . . . . ?
C14 C5 C6 C7 -0.3(3) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
C5 C6 C7 C16 1.2(3) . . . . ?
C5 C6 C7 C8 -179.44(18) . . . . ?
C6 C7 C8 C9 179.7(2) . . . . ?
C16 C7 C8 C9 -1.0(3) . . . . ?
C6 C7 C8 C18 1.7(3) . . . . ?
C16 C7 C8 C18 -179.03(19) . . . . ?
C7 C8 C9 C10 -3.1(4) . . . . ?
C18 C8 C9 C10 175.0(2) . . . . ?
C7 C8 C9 C11 179.8(2) . . . . ?
C18 C8 C9 C11 -2.1(3) . . . . ?
C2 C1 C12 C13 0.6(3) . . . . ?
C1 C12 C13 N3 -178.46(19) . . . . ?
C1 C12 C13 C4 -0.2(3) . . . . ?
C14 N3 C13 C12 178.44(19) . . . . ?
C17 N3 C13 C12 -6.1(3) . . . . ?
C14 N3 C13 C4 0.0(2) . . . . ?
C17 N3 C13 C4 175.52(18) . . . . ?
C3 C4 C13 C12 0.0(3) . . . . ?
C5 C4 C13 C12 -178.49(18) . . . . ?
C3 C4 C13 N3 178.54(17) . . . . ?
C5 C4 C13 N3 0.0(2) . . . . ?
C13 N3 C14 C15 -179.1(2) . . . . ?
C17 N3 C14 C15 5.6(3) . . . . ?
C13 N3 C14 C5 -0.1(2) . . . . ?
C17 N3 C14 C5 -175.47(19) . . . . ?
C6 C5 C14 N3 -179.10(17) . . . . ?
C4 C5 C14 N3 0.1(2) . . . . ?
C6 C5 C14 C15 0.0(3) . . . . ?
C4 C5 C14 C15 179.19(18) . . . . ?
N3 C14 C15 C16 178.3(2) . . . . ?
C5 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C7 1.5(3) . . . . ?
C6 C7 C16 C15 -1.8(3) . . . . ?
C8 C7 C16 C15 178.85(19) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.084



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

data_2-methoxy-9-methyl-3-122-tricyanovinyl-9H-carbazole
_database_code_depnum_ccdc_archive 'CCDC 1517414'
_audit_update_record             
;
2016-11-15 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 N4 O'
_chemical_formula_sum            'C19 H12 N4 O'
_chemical_formula_weight         312.33

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           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                   6.8946(9)
_cell_length_b                   16.799(2)
_cell_length_c                   13.329(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.493(6)
_cell_angle_gamma                90
_cell_volume                     1540.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1988
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      25.95

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4743
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18866
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.425
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_full        25.242
_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             3156
_reflns_number_gt                1988
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0488P)²+0.1346P]
 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         3156
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.5996(2) 0.26681(8) 0.29941(11) 0.0196(4) Uani 1 1 d . . . . .
N1 N 0.7548(2) 0.45884(11) 0.56769(13) 0.0147(4) Uani 1 1 d . . . . .
N2 N 1.0066(3) 0.49650(12) 0.11885(16) 0.0288(5) Uani 1 1 d . . . . .
N3 N 0.5435(3) 0.40872(11) -0.09682(16) 0.0240(5) Uani 1 1 d . . . . .
N4 N 0.2765(3) 0.30583(12) 0.11572(15) 0.0250(5) Uani 1 1 d . . . . .
C1 C 0.7837(3) 0.54123(13) 0.56343(17) 0.0143(5) Uani 1 1 d . . . . .
C2 C 0.8274(3) 0.59419(13) 0.64219(18) 0.0177(5) Uani 1 1 d . . . . .
H2 H 0.8421 0.5766 0.7100 0.021 Uiso 1 1 calc R U . . .
C3 C 0.8486(3) 0.67364(14) 0.61720(18) 0.0202(6) Uani 1 1 d . . . . .
H3 H 0.8786 0.7114 0.6689 0.024 Uiso 1 1 calc R U . . .
C4 C 0.8268(3) 0.69921(14) 0.51748(19) 0.0219(6) Uani 1 1 d . . . . .
H4 H 0.8417 0.7541 0.5027 0.026 Uiso 1 1 calc R U . . .
C5 C 0.7840(3) 0.64639(13) 0.43993(18) 0.0176(5) Uani 1 1 d . . . . .
H5 H 0.7698 0.6645 0.3723 0.021 Uiso 1 1 calc R U . . .
C6 C 0.7620(3) 0.56606(13) 0.46270(16) 0.0138(5) Uani 1 1 d . . . . .
C7 C 0.7185(3) 0.49511(13) 0.40397(17) 0.0135(5) Uani 1 1 d . . . . .
C8 C 0.6810(3) 0.48052(12) 0.30297(16) 0.0133(5) Uani 1 1 d . . . . .
H8 H 0.6841 0.5228 0.2558 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6384(3) 0.40283(13) 0.27031(17) 0.0144(5) Uani 1 1 d . . . . .
C10 C 0.6354(3) 0.33984(13) 0.34131(17) 0.0156(5) Uani 1 1 d . . . . .
C11 C 0.6743(3) 0.35303(13) 0.44212(17) 0.0147(5) Uani 1 1 d . . . . .
H11 H 0.6739 0.3106 0.4892 0.018 Uiso 1 1 calc R U . . .
C12 C 0.7143(3) 0.43065(13) 0.47280(17) 0.0133(5) Uani 1 1 d . . . . .
C13 C 0.5859(3) 0.38834(12) 0.16436(17) 0.0144(5) Uani 1 1 d . . . . .
C14 C 0.6808(3) 0.42137(12) 0.08751(17) 0.0148(5) Uani 1 1 d . . . . .
C15 C 0.8608(4) 0.46383(14) 0.10472(16) 0.0188(5) Uani 1 1 d . . . . .
C16 C 0.6063(3) 0.41471(13) -0.01537(18) 0.0169(5) Uani 1 1 d . . . . .
C17 C 0.4165(3) 0.34024(13) 0.13798(17) 0.0167(5) Uani 1 1 d . . . . .
C18 C 0.5956(4) 0.20003(13) 0.36588(19) 0.0242(6) Uani 1 1 d . . . . .
H18A H 0.5595 0.1521 0.3273 0.036 Uiso 1 1 calc R U . . .
H18B H 0.5002 0.2096 0.4161 0.036 Uiso 1 1 calc R U . . .
H18C H 0.7245 0.1927 0.3998 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7616(3) 0.41091(14) 0.65846(17) 0.0202(6) Uani 1 1 d . . . . .
H19A H 0.6295 0.3950 0.6730 0.030 Uiso 1 1 calc R U . . .
H19B H 0.8193 0.4421 0.7148 0.030 Uiso 1 1 calc R U . . .
H19C H 0.8405 0.3633 0.6488 0.030 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
O1 C10 1.364(3) . ?
O1 C18 1.431(3) . ?
N1 C12 1.363(3) . ?
N1 C1 1.400(3) . ?
N1 C19 1.452(3) . ?
N2 C15 1.151(3) . ?
N3 C16 1.148(3) . ?
N4 C17 1.148(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.447(3) . ?
C7 C8 1.377(3) . ?
C7 C12 1.421(3) . ?
C8 C9 1.401(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.421(3) . ?
C9 C13 1.457(3) . ?
C10 C11 1.372(3) . ?
C11 C12 1.389(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.366(3) . ?
C13 C17 1.446(3) . ?
C14 C15 1.437(3) . ?
C14 C16 1.439(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C18 117.48(17) . . ?
C12 N1 C1 109.11(18) . . ?
C12 N1 C19 125.09(19) . . ?
C1 N1 C19 125.78(18) . . ?
C2 C1 N1 128.7(2) . . ?
C2 C1 C6 122.4(2) . . ?
N1 C1 C6 108.97(19) . . ?
C3 C2 C1 117.0(2) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.3(2) . . ?
C5 C6 C7 134.5(2) . . ?
C1 C6 C7 106.19(19) . . ?
C8 C7 C12 119.1(2) . . ?
C8 C7 C6 134.1(2) . . ?
C12 C7 C6 106.86(19) . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 C13 119.46(19) . . ?
C10 C9 C13 120.56(19) . . ?
O1 C10 C11 124.5(2) . . ?
O1 C10 C9 114.00(19) . . ?
C11 C10 C9 121.5(2) . . ?
C10 C11 C12 117.6(2) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
N1 C12 C11 128.7(2) . . ?
N1 C12 C7 108.86(19) . . ?
C11 C12 C7 122.5(2) . . ?
C14 C13 C17 117.5(2) . . ?
C14 C13 C9 123.8(2) . . ?
C17 C13 C9 118.6(2) . . ?
C13 C14 C15 122.0(2) . . ?
C13 C14 C16 121.5(2) . . ?
C15 C14 C16 116.4(2) . . ?
N2 C15 C14 178.7(3) . . ?
N3 C16 C14 178.7(3) . . ?
N4 C17 C13 176.2(2) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.076



