# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1035363'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        zzq0923
_chemical_name_common            
(Z)-4-(9H-carbazol-9-yl)-N'-hydroxybenzimidamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N3 O'
_chemical_formula_sum            'C19 H15 N3 O'
_chemical_formula_weight         301.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/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                   8.778(5)
_cell_length_b                   27.635(5)
_cell_length_c                   7.797(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.261(5)
_cell_angle_gamma                90
_cell_volume                     1824.7(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3463
_cell_measurement_theta_min      3.1928
_cell_measurement_theta_max      29.0379

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83966
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            12029
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.199
_diffrn_reflns_theta_max         29.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4254
_reflns_number_gt                2945
_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       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+1.8953P] 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       0.041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4254
_refine_ls_number_parameters     215
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.1987
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.6859(3) -0.00435(9) -0.4170(3) 0.0756(7) Uani 1 1 d . . . . .
H1 H 0.6306 -0.0178 -0.5004 0.113 Uiso 1 1 d R U . . .
N1 N 0.3576(3) 0.14460(9) 0.2466(3) 0.0576(6) Uani 1 1 d . . . . .
N2 N 0.8040(4) 0.01088(16) -0.0880(4) 0.0968(12) Uani 1 1 d D . . . .
N3 N 0.5925(3) 0.02499(9) -0.3338(3) 0.0564(6) Uani 1 1 d . . . . .
C13 C 0.4328(3) 0.11617(9) 0.1411(3) 0.0498(6) Uani 1 1 d . . . . .
C14 C 0.4098(4) 0.12591(11) -0.0375(4) 0.0579(7) Uani 1 1 d . . . . .
H14 H 0.3442 0.1512 -0.0899 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5848(3) 0.06119(10) -0.0603(3) 0.0487(6) Uani 1 1 d . . . . .
C18 C 0.5337(3) 0.07924(10) 0.2188(3) 0.0520(7) Uani 1 1 d . . . . .
H18 H 0.5505 0.0727 0.3394 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3208(5) 0.19396(11) 0.4643(5) 0.0741(10) Uani 1 1 d . . . . .
C9 C -0.1066(7) 0.1843(2) 0.1889(10) 0.127(2) Uani 1 1 d . . . . .
H9 H -0.2096 0.1945 0.1786 0.152 Uiso 1 1 calc R U . . .
C19 C 0.6638(3) 0.03117(11) -0.1685(4) 0.0560(7) Uani 1 1 d . . . . .
C17 C 0.6085(3) 0.05237(10) 0.1192(3) 0.0521(7) Uani 1 1 d . . . . .
H17 H 0.6765 0.0277 0.1728 0.063 Uiso 1 1 calc DR U . . .
C1 C 0.4346(4) 0.16814(10) 0.4024(4) 0.0572(7) Uani 1 1 d . . . . .
C2 C 0.5925(5) 0.16995(11) 0.4875(4) 0.0706(9) Uani 1 1 d . . . . .
H2 H 0.6660 0.1530 0.4441 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1947(4) 0.15480(11) 0.2083(5) 0.0670(8) Uani 1 1 d . . . . .
C3 C 0.6390(6) 0.19769(13) 0.6396(5) 0.0937(14) Uani 1 1 d . . . . .
H3 H 0.7453 0.1993 0.7004 0.112 Uiso 1 1 calc R U . . .
C15 C 0.4831(3) 0.09844(11) -0.1374(4) 0.0559(7) Uani 1 1 d . . . . .
H15 H 0.4649 0.1047 -0.2584 0.067 Uiso 1 1 calc R U . . .
C8 C 0.0131(7) 0.20063(17) 0.3280(8) 0.1123(18) Uani 1 1 d . . . . .
H8 H -0.0084 0.2213 0.4130 0.135 Uiso 1 1 calc R U . . .
C11 C 0.0724(4) 0.13768(15) 0.0713(6) 0.0859(11) Uani 1 1 d . . . . .
H11 H 0.0914 0.1164 -0.0132 0.103 Uiso 1 1 calc R U . . .
C7 C 0.1710(5) 0.18546(12) 0.3403(5) 0.0789(11) Uani 1 1 d . . . . .
C5 C 0.3711(8) 0.22165(14) 0.6173(6) 0.1018(16) Uani 1 1 d . . . . .
H5 H 0.2985 0.2389 0.6612 0.122 Uiso 1 1 calc R U . . .
C10 C -0.0761(5) 0.15294(19) 0.0640(8) 0.1111(16) Uani 1 1 d . . . . .
H10 H -0.1598 0.1420 -0.0275 0.133 Uiso 1 1 calc R U . . .
C4 C 0.5286(9) 0.22334(14) 0.7029(6) 0.1128(19) Uani 1 1 d . . . . .
H4 H 0.5625 0.2420 0.8052 0.135 Uiso 1 1 calc R U . . .
H2B H 0.828(4) 0.0020(15) 0.0266(19) 0.135 Uiso 1 1 d D U . . .
H2A H 0.842(5) -0.0027(16) -0.173(5) 0.135 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
O1 N3 1.425(3) . ?
O1 H1 0.7940 . ?
N1 C1 1.386(4) . ?
N1 C12 1.411(4) . ?
N1 C13 1.419(3) . ?
N2 C19 1.348(4) . ?
N2 H2B 0.897(5) . ?
N2 H2A 0.899(5) . ?
N3 C19 1.287(3) . ?
C13 C14 1.380(4) . ?
C13 C18 1.382(4) . ?
C14 C15 1.364(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.381(4) . ?
C16 C15 1.391(4) . ?
C16 C19 1.480(4) . ?
C18 C17 1.362(4) . ?
C18 H18 0.9300 . ?
C6 C5 1.388(5) . ?
C6 C1 1.412(4) . ?
C6 C7 1.432(6) . ?
C9 C8 1.372(8) . ?
C9 C10 1.382(8) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C1 C2 1.371(5) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C12 C11 1.383(5) . ?
C12 C7 1.391(5) . ?
C3 C4 1.392(7) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C8 C7 1.428(6) . ?
C8 H8 0.9300 . ?
C11 C10 1.357(6) . ?
C11 H11 0.9300 . ?
C5 C4 1.369(7) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C4 H4 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
N3 O1 H1 109.8 . . ?
C1 N1 C12 109.0(2) . . ?
C1 N1 C13 125.0(3) . . ?
C12 N1 C13 126.0(3) . . ?
C19 N2 H2B 121.6(11) . . ?
C19 N2 H2A 107(3) . . ?
H2B N2 H2A 126(3) . . ?
C19 N3 O1 110.2(2) . . ?
C14 C13 C18 119.5(2) . . ?
C14 C13 N1 120.7(3) . . ?
C18 C13 N1 119.8(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C17 C16 C15 118.5(2) . . ?
C17 C16 C19 120.7(3) . . ?
C15 C16 C19 120.8(2) . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C5 C6 C1 118.7(4) . . ?
C5 C6 C7 134.3(4) . . ?
C1 C6 C7 107.0(3) . . ?
C8 C9 C10 120.9(5) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N3 C19 N2 123.7(3) . . ?
N3 C19 C16 117.9(3) . . ?
N2 C19 C16 118.4(3) . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C2 C1 N1 129.7(3) . . ?
C2 C1 C6 122.1(3) . . ?
N1 C1 C6 108.2(3) . . ?
C1 C2 C3 118.0(4) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C11 C12 C7 122.9(4) . . ?
C11 C12 N1 129.3(3) . . ?
C7 C12 N1 107.8(3) . . ?
C2 C3 C4 120.7(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C9 C8 C7 119.0(5) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C11 C12 117.9(5) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C12 C7 C8 117.4(5) . . ?
C12 C7 C6 108.1(3) . . ?
C8 C7 C6 134.4(4) . . ?
C4 C5 C6 119.3(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C11 C10 C9 121.9(5) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?

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
C1 N1 C13 C14 -125.4(3) . . . . ?
C12 N1 C13 C14 52.5(4) . . . . ?
C1 N1 C13 C18 52.7(4) . . . . ?
C12 N1 C13 C18 -129.4(3) . . . . ?
C18 C13 C14 C15 1.7(4) . . . . ?
N1 C13 C14 C15 179.8(3) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
N1 C13 C18 C17 -178.8(3) . . . . ?
O1 N3 C19 N2 -2.2(5) . . . . ?
O1 N3 C19 C16 179.5(2) . . . . ?
C17 C16 C19 N3 149.7(3) . . . . ?
C15 C16 C19 N3 -29.3(4) . . . . ?
C17 C16 C19 N2 -28.7(4) . . . . ?
C15 C16 C19 N2 152.3(3) . . . . ?
C13 C18 C17 C16 -0.3(4) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C19 C16 C17 C18 -178.7(3) . . . . ?
C12 N1 C1 C2 -177.8(3) . . . . ?
C13 N1 C1 C2 0.4(5) . . . . ?
C12 N1 C1 C6 -0.4(3) . . . . ?
C13 N1 C1 C6 177.8(2) . . . . ?
C5 C6 C1 C2 -0.6(5) . . . . ?
C7 C6 C1 C2 177.5(3) . . . . ?
C5 C6 C1 N1 -178.2(3) . . . . ?
C7 C6 C1 N1 -0.2(3) . . . . ?
N1 C1 C2 C3 177.9(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 N1 C12 C11 -177.1(3) . . . . ?
C13 N1 C12 C11 4.8(5) . . . . ?
C1 N1 C12 C7 0.8(3) . . . . ?
C13 N1 C12 C7 -177.4(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C13 C14 C15 C16 -1.7(5) . . . . ?
C17 C16 C15 C14 0.7(4) . . . . ?
C19 C16 C15 C14 179.7(3) . . . . ?
C10 C9 C8 C7 1.3(7) . . . . ?
C7 C12 C11 C10 2.0(5) . . . . ?
N1 C12 C11 C10 179.6(3) . . . . ?
C11 C12 C7 C8 -2.0(5) . . . . ?
N1 C12 C7 C8 180.0(3) . . . . ?
C11 C12 C7 C6 177.1(3) . . . . ?
N1 C12 C7 C6 -0.9(3) . . . . ?
C9 C8 C7 C12 0.3(6) . . . . ?
C9 C8 C7 C6 -178.5(4) . . . . ?
C5 C6 C7 C12 178.3(4) . . . . ?
C1 C6 C7 C12 0.6(3) . . . . ?
C5 C6 C7 C8 -2.8(7) . . . . ?
C1 C6 C7 C8 179.6(4) . . . . ?
C1 C6 C5 C4 0.3(5) . . . . ?
C7 C6 C5 C4 -177.2(4) . . . . ?
C12 C11 C10 C9 -0.4(6) . . . . ?
C8 C9 C10 C11 -1.3(8) . . . . ?
C6 C5 C4 C3 -0.2(6) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.79 2.05 2.752(3) 146.9 3_654
N2 H2A O1 0.899(5) 2.03(4) 2.536(4) 115(4) .

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.257 0.603 1.002 209 25 ' '
_platon_squeeze_details          
;
;

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_preparation       Luminescent
