# Electronic Supplementary Material (ESI) for ChemComm.
# 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_cd1337a
_database_code_depnum_ccdc_archive 'CCDC 1474206'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2015-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '2-Phenylpyridine N-Oxide'
_chemical_formula_moiety         'C11 H9 N O'
_chemical_formula_sum            'C11 H9 N O'
_chemical_formula_weight         171.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

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

_cell_length_a                   5.8141(14)
_cell_length_b                   23.591(5)
_cell_length_c                   6.8413(16)
_cell_angle_alpha                90
_cell_angle_beta                 114.257(3)
_cell_angle_gamma                90
_cell_volume                     855.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3924
_cell_measurement_temperature    293
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2600
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         3.695
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -125.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.9735
	          2theta: -35.0128
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.007005
_diffrn_orient_matrix_UB_12      0.153049
_diffrn_orient_matrix_UB_13      0.110075
_diffrn_orient_matrix_UB_21      -0.031068
_diffrn_orient_matrix_UB_22      0.015887
_diffrn_orient_matrix_UB_23      -0.024067
_diffrn_orient_matrix_UB_31      -0.101739
_diffrn_orient_matrix_UB_32      -0.012155
_diffrn_orient_matrix_UB_33      0.123313
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1310
_reflns_number_total             1458
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C7(H7), C3(H3), C1(H1), C2(H2), C9(H9), C10(H10), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2073(2) 0.56429(6) 0.6716(2) 0.0528(4) Uani 1 1 d . . . . .
N1 N 0.3024(3) 0.56749(6) 0.5285(2) 0.0383(4) Uani 1 1 d . . . . .
C5 C 0.4994(3) 0.60382(7) 0.5595(3) 0.0362(4) Uani 1 1 d . . . . .
C6 C 0.5962(3) 0.63972(7) 0.7524(3) 0.0370(4) Uani 1 1 d . . . . .
C11 C 0.4392(4) 0.67626(8) 0.8023(3) 0.0463(5) Uani 1 1 d . . . . .
H11 H 0.2667 0.6764 0.7173 0.056 Uiso 1 1 calc R . . . .
C4 C 0.6010(3) 0.60459(8) 0.4081(3) 0.0449(4) Uani 1 1 d . . . . .
H4 H 0.7360 0.6286 0.4286 0.054 Uiso 1 1 calc R . . . .
C7 C 0.8536(3) 0.63982(8) 0.8834(3) 0.0439(4) Uani 1 1 d . . . . .
H7 H 0.9615 0.6161 0.8519 0.053 Uiso 1 1 calc R . . . .
C3 C 0.5075(4) 0.57093(9) 0.2289(3) 0.0515(5) Uani 1 1 d . . . . .
H3 H 0.5755 0.5723 0.1273 0.062 Uiso 1 1 calc R . . . .
C1 C 0.2104(3) 0.53375(8) 0.3532(3) 0.0453(4) Uani 1 1 d . . . . .
H1 H 0.0773 0.5094 0.3343 0.054 Uiso 1 1 calc R . . . .
C2 C 0.3096(4) 0.53483(9) 0.2031(3) 0.0492(5) Uani 1 1 d . . . . .
H2 H 0.2439 0.5113 0.0837 0.059 Uiso 1 1 calc R . . . .
C9 C 0.7922(4) 0.71121(9) 1.1069(3) 0.0589(6) Uani 1 1 d . . . . .
H9 H 0.8572 0.7350 1.2257 0.071 Uiso 1 1 calc R . . . .
C10 C 0.5365(4) 0.71178(9) 0.9752(4) 0.0566(5) Uani 1 1 d . . . . .
H10 H 0.4303 0.7365 1.0047 0.068 Uiso 1 1 calc R . . . .
C8 C 0.9493(4) 0.67506(9) 1.0602(3) 0.0545(5) Uani 1 1 d . . . . .
H8 H 1.1209 0.6744 1.1483 0.065 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3091(18) . ?
N1 C5 1.376(2) . ?
N1 C1 1.353(2) . ?
C5 C6 1.471(2) . ?
C5 C4 1.388(2) . ?
C6 C11 1.396(2) . ?
C6 C7 1.393(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.372(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.383(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.369(3) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.386(3) . ?
C9 C8 1.380(3) . ?
C10 H10 0.9300 . ?
C8 H8 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
O1 N1 C5 120.10(14) . . ?
O1 N1 C1 119.63(14) . . ?
C1 N1 C5 120.24(15) . . ?
N1 C5 C6 118.97(14) . . ?
N1 C5 C4 118.43(16) . . ?
C4 C5 C6 122.60(15) . . ?
C11 C6 C5 121.82(16) . . ?
C7 C6 C5 119.48(15) . . ?
C7 C6 C11 118.61(17) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 C6 120.65(18) . . ?
C10 C11 H11 119.7 . . ?
C5 C4 H4 119.1 . . ?
C3 C4 C5 121.73(17) . . ?
C3 C4 H4 119.1 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.27(17) . . ?
C8 C7 H7 119.9 . . ?
C4 C3 H3 120.9 . . ?
C4 C3 C2 118.27(17) . . ?
C2 C3 H3 120.9 . . ?
N1 C1 H1 119.4 . . ?
N1 C1 C2 121.28(17) . . ?
C2 C1 H1 119.4 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.03(18) . . ?
C1 C2 H2 120.0 . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.40(19) . . ?
C11 C10 C9 120.55(18) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.50(19) . . ?
C9 C8 H8 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
O1 N1 C5 C6 -1.5(2) . . . . ?
O1 N1 C5 C4 177.77(15) . . . . ?
O1 N1 C1 C2 -178.24(16) . . . . ?
N1 C5 C6 C11 -55.6(2) . . . . ?
N1 C5 C6 C7 127.93(17) . . . . ?
N1 C5 C4 C3 1.0(3) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
C5 N1 C1 C2 -0.1(3) . . . . ?
C5 C6 C11 C10 -175.88(17) . . . . ?
C5 C6 C7 C8 177.25(16) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
C6 C5 C4 C3 -179.77(16) . . . . ?
C6 C11 C10 C9 -1.5(3) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C11 C6 C7 C8 0.7(3) . . . . ?
C4 C5 C6 C11 125.18(19) . . . . ?
C4 C5 C6 C7 -51.3(2) . . . . ?
C4 C3 C2 C1 0.6(3) . . . . ?
C7 C6 C11 C10 0.6(3) . . . . ?
C1 N1 C5 C6 -179.65(15) . . . . ?
C1 N1 C5 C4 -0.4(2) . . . . ?
C10 C9 C8 C7 0.2(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_cd1340a
_database_code_depnum_ccdc_archive 'CCDC 1474207'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2015-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
'3-Methylquinoline N-Oxide meta-Chlorobenzoic Acid (1:1) Complex '
_chemical_formula_moiety         'C7 H5 Cl O2, C10 H9 N O'
_chemical_formula_sum            'C17 H14 Cl N O3'
_chemical_formula_weight         315.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.840(4)
_cell_length_b                   13.517(4)
_cell_length_c                   7.047(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.395(5)
_cell_angle_gamma                90
_cell_volume                     1479.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4441
_cell_measurement_temperature    293
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.9
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8740
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         3.014
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 34.9506
	          2theta: -35.0083
scan:
	Number of images: 226
	           Slice: -68.0000 - 45.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 34.9506
	          2theta: -35.0083
scan:
	Number of images: 82
	           Slice: -66.0000 - -25.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.9506
	          2theta: -35.0083
scan:
	Number of images: 68
	           Slice: -125.0000 - -91.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.9506
	          2theta: -35.0083
scan:
	Number of images: 58
	           Slice: -43.0000 - -14.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.9506
	          2theta: -35.0083
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.050501
_diffrn_orient_matrix_UB_12      0.121109
_diffrn_orient_matrix_UB_13      -0.061116
_diffrn_orient_matrix_UB_21      -0.068556
_diffrn_orient_matrix_UB_22      -0.017816
_diffrn_orient_matrix_UB_23      0.021343
_diffrn_orient_matrix_UB_31      0.004380
_diffrn_orient_matrix_UB_32      0.041700
_diffrn_orient_matrix_UB_33      0.048879
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2325
_reflns_number_total             2574
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1280
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C1(H1), C3(H3), C8(H8), C14(H14), C12(H12), C5(H5), C13(H13),
 C7(H7), C6(H6)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.13714(3) 0.07900(3) -0.08816(7) 0.0650(2) Uani 1 1 d . . . . .
O2 O 0.26249(8) 0.43664(10) -0.0311(2) 0.0578(3) Uani 1 1 d . . . . .
H2 H 0.2920 0.4867 -0.0082 0.087 Uiso 1 1 calc GR . . . .
O1 O 0.37299(8) 0.57627(10) 0.05617(17) 0.0594(4) Uani 1 1 d . . . . .
O3 O 0.15440(9) 0.54483(10) -0.0547(2) 0.0644(4) Uani 1 1 d . . . . .
N1 N 0.38059(9) 0.60224(9) 0.24063(19) 0.0445(3) Uani 1 1 d . . . . .
C15 C 0.12140(10) 0.37337(12) -0.0939(2) 0.0441(4) Uani 1 1 d . . . . .
C16 C 0.15353(10) 0.27760(12) -0.0791(2) 0.0457(4) Uani 1 1 d . . . . .
H16 H 0.2126 0.2664 -0.0493 0.055 Uiso 1 1 calc R . . . .
C17 C 0.17989(11) 0.46075(13) -0.0588(2) 0.0481(4) Uani 1 1 d . . . . .
C4 C 0.46975(10) 0.64008(10) 0.5484(2) 0.0439(4) Uani 1 1 d . . . . .
C9 C 0.46289(10) 0.61316(10) 0.3530(2) 0.0436(4) Uani 1 1 d . . . . .
C1 C 0.31037(10) 0.61814(11) 0.3150(2) 0.0459(4) Uani 1 1 d . . . . .
H1 H 0.2564 0.6110 0.2353 0.055 Uiso 1 1 calc R . . . .
C2 C 0.31516(11) 0.64511(11) 0.5082(2) 0.0468(4) Uani 1 1 d . . . . .
C3 C 0.39497(11) 0.65500(11) 0.6252(2) 0.0475(4) Uani 1 1 d . . . . .
H3 H 0.3998 0.6715 0.7550 0.057 Uiso 1 1 calc R . . . .
C8 C 0.53527(12) 0.59688(12) 0.2709(3) 0.0531(4) Uani 1 1 d . . . . .
H8 H 0.5293 0.5790 0.1415 0.064 Uiso 1 1 calc R . . . .
C14 C 0.03309(11) 0.38874(14) -0.1380(2) 0.0531(4) Uani 1 1 d . . . . .
H14 H 0.0112 0.4528 -0.1476 0.064 Uiso 1 1 calc R . . . .
C12 C 0.00881(12) 0.21321(15) -0.1548(3) 0.0579(4) Uani 1 1 d . . . . .
H12 H -0.0286 0.1596 -0.1762 0.070 Uiso 1 1 calc R . . . .
C11 C 0.09659(11) 0.19909(13) -0.1094(2) 0.0483(4) Uani 1 1 d . . . . .
C5 C 0.55409(11) 0.64962(13) 0.6619(3) 0.0533(4) Uani 1 1 d . . . . .
H5 H 0.5614 0.6666 0.7920 0.064 Uiso 1 1 calc R . . . .
C13 C -0.02223(12) 0.30883(16) -0.1676(3) 0.0630(5) Uani 1 1 d . . . . .
H13 H -0.0814 0.3196 -0.1967 0.076 Uiso 1 1 calc R . . . .
C7 C 0.61565(12) 0.60812(14) 0.3870(3) 0.0593(5) Uani 1 1 d . . . . .
H7 H 0.6646 0.5982 0.3350 0.071 Uiso 1 1 calc R . . . .
C10 C 0.23340(12) 0.66249(15) 0.5808(3) 0.0625(5) Uani 1 1 d . . . . .
H10A H 0.2117 0.7273 0.5429 0.094 Uiso 1 1 calc GR . . . .
H10B H 0.2448 0.6575 0.7194 0.094 Uiso 1 1 calc GR . . . .
H10C H 0.1914 0.6138 0.5266 0.094 Uiso 1 1 calc GR . . . .
C6 C 0.62434(11) 0.63412(13) 0.5813(3) 0.0592(5) Uani 1 1 d . . . . .
H6 H 0.6791 0.6410 0.6573 0.071 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.7413(18) . ?
O2 H2 0.8200 . ?
O2 C17 1.325(2) . ?
O1 N1 1.3288(18) . ?
O3 C17 1.208(2) . ?
N1 C9 1.393(2) . ?
N1 C1 1.338(2) . ?
C15 C16 1.387(2) . ?
C15 C17 1.491(2) . ?
C15 C14 1.387(2) . ?
C16 H16 0.9300 . ?
C16 C11 1.382(2) . ?
C4 C9 1.407(2) . ?
C4 C3 1.411(2) . ?
C4 C5 1.421(2) . ?
C9 C8 1.400(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.397(2) . ?
C2 C3 1.372(2) . ?
C2 C10 1.502(2) . ?
C3 H3 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(3) . ?
C12 C13 1.379(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.362(3) . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.394(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C6 H6 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
C17 O2 H2 109.5 . . ?
O1 N1 C9 118.55(13) . . ?
O1 N1 C1 120.28(13) . . ?
C1 N1 C9 121.16(14) . . ?
C16 C15 C17 121.32(14) . . ?
C14 C15 C16 119.69(16) . . ?
C14 C15 C17 118.97(15) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 C15 119.10(15) . . ?
C11 C16 H16 120.4 . . ?
O2 C17 C15 113.12(14) . . ?
O3 C17 O2 123.55(16) . . ?
O3 C17 C15 123.32(16) . . ?
C9 C4 C3 120.26(15) . . ?
C9 C4 C5 117.15(15) . . ?
C3 C4 C5 122.58(16) . . ?
N1 C9 C4 117.80(14) . . ?
N1 C9 C8 119.93(15) . . ?
C8 C9 C4 122.27(15) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.32(15) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C10 119.23(15) . . ?
C3 C2 C1 118.48(15) . . ?
C3 C2 C10 122.29(17) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.96(16) . . ?
C2 C3 H3 120.0 . . ?
C9 C8 H8 120.9 . . ?
C7 C8 C9 118.22(17) . . ?
C7 C8 H8 120.9 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 119.90(17) . . ?
C13 C14 H14 120.0 . . ?
C11 C12 H12 120.8 . . ?
C11 C12 C13 118.40(17) . . ?
C13 C12 H12 120.8 . . ?
C16 C11 Cl1 118.96(13) . . ?
C12 C11 Cl1 119.18(14) . . ?
C12 C11 C16 121.86(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.42(17) . . ?
C6 C5 H5 119.8 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 121.04(16) . . ?
C12 C13 H13 119.5 . . ?
C8 C7 H7 119.6 . . ?
C8 C7 C6 120.72(17) . . ?
C6 C7 H7 119.6 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C6 C7 121.21(17) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 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
O1 N1 C9 C4 -179.60(13) . . . . ?
O1 N1 C9 C8 0.0(2) . . . . ?
O1 N1 C1 C2 179.71(14) . . . . ?
N1 C9 C8 C7 -179.79(15) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
N1 C1 C2 C10 179.52(15) . . . . ?
C15 C16 C11 Cl1 -179.31(11) . . . . ?
C15 C16 C11 C12 0.3(2) . . . . ?
C15 C14 C13 C12 -0.2(3) . . . . ?
C16 C15 C17 O2 5.7(2) . . . . ?
C16 C15 C17 O3 -173.78(16) . . . . ?
C16 C15 C14 C13 -0.2(3) . . . . ?
C17 C15 C16 C11 178.79(14) . . . . ?
C17 C15 C14 C13 -178.88(15) . . . . ?
C4 C9 C8 C7 -0.2(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C9 N1 C1 C2 -0.8(2) . . . . ?
C9 C4 C3 C2 -1.2(2) . . . . ?
C9 C4 C5 C6 0.7(2) . . . . ?
C9 C8 C7 C6 0.6(3) . . . . ?
C1 N1 C9 C4 0.9(2) . . . . ?
C1 N1 C9 C8 -179.43(14) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C3 C4 C9 N1 0.1(2) . . . . ?
C3 C4 C9 C8 -179.53(14) . . . . ?
C3 C4 C5 C6 179.77(15) . . . . ?
C8 C7 C6 C5 -0.3(3) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?
C14 C15 C17 O2 -175.71(15) . . . . ?
C14 C15 C17 O3 4.9(2) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C5 C4 C9 N1 179.16(13) . . . . ?
C5 C4 C9 C8 -0.5(2) . . . . ?
C5 C4 C3 C2 179.75(14) . . . . ?
C13 C12 C11 Cl1 178.88(14) . . . . ?
C13 C12 C11 C16 -0.8(3) . . . . ?
C10 C2 C3 C4 -178.50(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1345a
_database_code_depnum_ccdc_archive 'CCDC 1474208'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2015-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        6,6'-Diisopropyl-2,2'-biquinoline
_chemical_formula_moiety         'C24 H24 N2'
_chemical_formula_sum            'C24 H24 N2'
_chemical_formula_weight         340.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_cell_length_a                   12.648(15)
_cell_length_b                   5.914(7)
_cell_length_c                   13.125(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.02(2)
_cell_angle_gamma                90
_cell_volume                     979(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1998
_cell_measurement_temperature    293
_cell_measurement_theta_max      39.7
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Vapor diffusion of pentane into ethylacetate/chloroform mixture'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3070
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.045
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_min         3.112
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
scan:
	Number of images: 182
	           Slice: -125.0000 - -34.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 35.1329
	          2theta: -34.5652
scan:
	Number of images: 138
	           Slice: -51.0000 - 18.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 35.1329
	          2theta: -34.5652
scan:
	Number of images: 72
	           Slice: -125.0000 - -89.0000
	     Image width: 0.5000
	        Exp time: 45.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 35.1329
	          2theta: -34.5652
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.012006
_diffrn_orient_matrix_UB_12      -0.000408
_diffrn_orient_matrix_UB_13      -0.078346
_diffrn_orient_matrix_UB_21      0.154929
_diffrn_orient_matrix_UB_22      -0.063556
_diffrn_orient_matrix_UB_23      -0.023410
_diffrn_orient_matrix_UB_31      -0.029067
_diffrn_orient_matrix_UB_32      -0.070633
_diffrn_orient_matrix_UB_33      -0.000602
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                859
_reflns_number_total             1699
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.067(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1699
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1519
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C8(H8), C7(H7)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3928(2) 0.5684(4) 0.0753(2) 0.0732(8) Uani 1 1 d . . . . .
C1 C 0.4720(2) 0.4505(5) 0.0423(2) 0.0676(8) Uani 1 1 d . . . . .
C2 C 0.5022(2) 0.2365(5) 0.0834(2) 0.0734(9) Uani 1 1 d . . . . .
H2 H 0.5575 0.1568 0.0570 0.088 Uiso 1 1 calc R . . . .
C4 C 0.3664(2) 0.2701(5) 0.2013(2) 0.0677(8) Uani 1 1 d . . . . .
C3 C 0.4504(2) 0.1482(5) 0.1613(2) 0.0764(9) Uani 1 1 d . . . . .
H3 H 0.4700 0.0077 0.1883 0.092 Uiso 1 1 calc R . . . .
C5 C 0.3106(2) 0.1939(5) 0.2838(2) 0.0768(9) Uani 1 1 d . . . . .
H5 H 0.3292 0.0563 0.3143 0.092 Uiso 1 1 calc R . . . .
C9 C 0.3404(2) 0.4812(5) 0.1552(2) 0.0701(9) Uani 1 1 d . . . . .
C8 C 0.2559(3) 0.6068(6) 0.1932(3) 0.0822(10) Uani 1 1 d . . . . .
H8 H 0.2360 0.7442 0.1632 0.099 Uiso 1 1 calc R . . . .
C7 C 0.2041(3) 0.5275(6) 0.2728(3) 0.0830(10) Uani 1 1 d . . . . .
H7 H 0.1500 0.6143 0.2971 0.100 Uiso 1 1 calc R . . . .
C6 C 0.2294(3) 0.3174(6) 0.3205(3) 0.0777(9) Uani 1 1 d . . . . .
C10 C 0.1689(3) 0.2324(7) 0.4079(3) 0.0904(11) Uani 1 1 d . . . . .
H10 H 0.2046 0.0954 0.4345 0.108 Uiso 1 1 calc R . . . .
C11 C 0.0561(3) 0.1665(9) 0.3703(3) 0.1359(18) Uani 1 1 d . . . . .
H11A H 0.0176 0.2993 0.3476 0.204 Uiso 1 1 calc GR . . . .
H11B H 0.0213 0.0973 0.4251 0.204 Uiso 1 1 calc GR . . . .
H11C H 0.0583 0.0616 0.3147 0.204 Uiso 1 1 calc GR . . . .
C12 C 0.1690(3) 0.4023(8) 0.4953(3) 0.1215(16) Uani 1 1 d . . . . .
H12A H 0.2407 0.4420 0.5168 0.182 Uiso 1 1 calc GR . . . .
H12B H 0.1354 0.3363 0.5515 0.182 Uiso 1 1 calc GR . . . .
H12C H 0.1310 0.5355 0.4725 0.182 Uiso 1 1 calc GR . . . .


_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 C1 1.319(4) . ?
N1 C9 1.379(4) . ?
C1 C1 1.479(6) 3_665 ?
C1 C2 1.417(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(4) . ?
C4 C3 1.414(4) . ?
C4 C5 1.408(4) . ?
C4 C9 1.416(4) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.375(4) . ?
C9 C8 1.420(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.356(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.418(5) . ?
C6 C10 1.509(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.528(5) . ?
C10 C12 1.525(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C1 N1 C9 117.9(3) . . ?
N1 C1 C1 116.8(3) . 3_665 ?
N1 C1 C2 122.6(3) . . ?
C2 C1 C1 120.6(4) . 3_665 ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C3 C4 C9 116.7(3) . . ?
C5 C4 C3 123.5(3) . . ?
C5 C4 C9 119.8(3) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
N1 C9 C4 123.0(3) . . ?
N1 C9 C8 119.0(3) . . ?
C4 C9 C8 118.0(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C8 C7 H7 118.8 . . ?
C8 C7 C6 122.5(3) . . ?
C6 C7 H7 118.8 . . ?
C5 C6 C7 117.5(3) . . ?
C5 C6 C10 121.4(3) . . ?
C7 C6 C10 121.1(3) . . ?
C6 C10 H10 107.5 . . ?
C6 C10 C11 110.6(3) . . ?
C6 C10 C12 112.2(3) . . ?
C11 C10 H10 107.5 . . ?
C12 C10 H10 107.5 . . ?
C12 C10 C11 111.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
N1 C1 C2 C3 -1.5(4) . . . . ?
N1 C9 C8 C7 -178.9(3) . . . . ?
C1 N1 C9 C4 -1.5(4) . . . . ?
C1 N1 C9 C8 179.0(3) . . . . ?
C1 C1 C2 C3 179.8(3) 3_665 . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C4 C5 C6 C10 179.0(3) . . . . ?
C4 C9 C8 C7 1.6(4) . . . . ?
C3 C4 C5 C6 -180.0(3) . . . . ?
C3 C4 C9 N1 0.0(4) . . . . ?
C3 C4 C9 C8 179.5(3) . . . . ?
C5 C4 C3 C2 -178.1(3) . . . . ?
C5 C4 C9 N1 178.9(3) . . . . ?
C5 C4 C9 C8 -1.6(4) . . . . ?
C5 C6 C10 C11 -110.0(4) . . . . ?
C5 C6 C10 C12 125.2(3) . . . . ?
C9 N1 C1 C1 -179.0(3) . . . 3_665 ?
C9 N1 C1 C2 2.2(4) . . . . ?
C9 C4 C3 C2 0.8(4) . . . . ?
C9 C4 C5 C6 1.2(4) . . . . ?
C9 C8 C7 C6 -1.2(5) . . . . ?
C8 C7 C6 C5 0.7(5) . . . . ?
C8 C7 C6 C10 -179.0(3) . . . . ?
C7 C6 C10 C11 69.8(4) . . . . ?
C7 C6 C10 C12 -55.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1384a
_database_code_depnum_ccdc_archive 'CCDC 1474209'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '6-Methoxuquinoline N-Oxide Dihydrate'
_chemical_formula_moiety         'C10 H9 N O2, 2(H2 O)'
_chemical_formula_sum            'C10 H13 N O4'
_chemical_formula_weight         211.21
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.8503(12)
_cell_length_b                   17.114(4)
_cell_length_c                   6.4411(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.911(4)
_cell_angle_gamma                90
_cell_volume                     514.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2704
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      3.6
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_recrystallization_method 'vapor diffsion of MeCN/hexane'
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3647
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         4.061
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 34.5687
	          2theta: -34.7877
scan:
	Number of images: 124
	           Slice: -62.0000 - 0.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.5687
	          2theta: -34.7877
scan:
	Number of images: 120
	           Slice: -80.0000 - -20.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.5687
	          2theta: -34.7877
scan:
	Number of images: 90
	           Slice: -67.0000 - -22.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 34.5687
	          2theta: -34.7877
scan:
	Number of images: 60
	           Slice: -115.0000 - -85.0000
	     Image width: 0.5000
	        Exp time: 30.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.5687
	          2theta: -34.7877
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.117370
_diffrn_orient_matrix_UB_12      0.051424
_diffrn_orient_matrix_UB_13      0.171876
_diffrn_orient_matrix_UB_21      0.001968
_diffrn_orient_matrix_UB_22      -0.055566
_diffrn_orient_matrix_UB_23      0.017969
_diffrn_orient_matrix_UB_31      0.105585
_diffrn_orient_matrix_UB_32      0.040947
_diffrn_orient_matrix_UB_33      0.115053
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                2205
_reflns_number_total             2236
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.1600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0902
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C2(H2), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.4925(4) -0.36318(9) -0.2636(2) 0.0223(4) Uani 1 1 d . . . . .
O4 O -0.3383(4) -0.28953(10) 0.1244(3) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.0345(3) -0.62555(9) -0.7132(2) 0.0222(4) Uani 1 1 d . . . . .
O3 O -0.7692(4) -0.32290(11) -0.6854(3) 0.0282(4) Uani 1 1 d . . . . .
N1 N -0.4893(4) -0.44026(10) -0.2309(3) 0.0173(4) Uani 1 1 d . . . . .
C4 C -0.0991(4) -0.58538(12) -0.5865(3) 0.0174(4) Uani 1 1 d . . . . .
C1 C -0.3552(4) -0.48796(12) -0.3477(3) 0.0160(4) Uani 1 1 d . . . . .
C3 C -0.0893(4) -0.50283(13) -0.6077(3) 0.0184(4) Uani 1 1 d . . . . .
H3 H 0.0040 -0.4813 -0.7025 0.022 Uiso 1 1 calc R . . . .
C5 C -0.2314(4) -0.61871(12) -0.4449(3) 0.0176(4) Uani 1 1 d . . . . .
H5 H -0.2353 -0.6727 -0.4306 0.021 Uiso 1 1 calc R . . . .
C7 C -0.4989(4) -0.60090(13) -0.1703(3) 0.0186(4) Uani 1 1 d . . . . .
H7 H -0.5047 -0.6546 -0.1494 0.022 Uiso 1 1 calc R . . . .
C6 C -0.3619(4) -0.57003(12) -0.3208(3) 0.0157(4) Uani 1 1 d . . . . .
C2 C -0.2146(4) -0.45456(12) -0.4913(3) 0.0179(4) Uani 1 1 d . . . . .
H2 H -0.2074 -0.4006 -0.5063 0.022 Uiso 1 1 calc R . . . .
C9 C -0.6172(5) -0.47006(13) -0.0896(3) 0.0193(4) Uani 1 1 d . . . . .
H9 H -0.7039 -0.4367 -0.0123 0.023 Uiso 1 1 calc R . . . .
C8 C -0.6223(5) -0.55091(13) -0.0563(3) 0.0205(5) Uani 1 1 d . . . . .
H8 H -0.7102 -0.5707 0.0440 0.025 Uiso 1 1 calc R . . . .
C10 C 0.0360(6) -0.70902(14) -0.6982(4) 0.0300(5) Uani 1 1 d . . . . .
H10A H 0.1391 -0.7305 -0.7927 0.045 Uiso 1 1 calc GR . . . .
H10B H -0.1575 -0.7281 -0.7397 0.045 Uiso 1 1 calc GR . . . .
H10C H 0.1276 -0.7245 -0.5523 0.045 Uiso 1 1 calc GR . . . .
H3A H -0.642(8) -0.313(2) -0.739(6) 0.045 Uiso 1 1 d R . . . .
H4A H -0.380(8) -0.310(2) 0.002(6) 0.045 Uiso 1 1 d R . . . .
H4B H -0.173(9) -0.297(2) 0.176(6) 0.045 Uiso 1 1 d R . . . .
H3B H -0.680(9) -0.334(2) -0.558(7) 0.045 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.335(2) . ?
O4 H4A 0.84(4) . ?
O4 H4B 0.79(4) . ?
O2 C4 1.360(2) . ?
O2 C10 1.432(3) . ?
O3 H3A 0.80(4) . ?
O3 H3B 0.84(4) . ?
N1 C1 1.387(3) . ?
N1 C9 1.335(3) . ?
C4 C3 1.421(3) . ?
C4 C5 1.375(3) . ?
C1 C6 1.417(3) . ?
C1 C2 1.411(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.365(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.418(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.419(3) . ?
C7 C8 1.368(3) . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.401(3) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
H4A O4 H4B 107(4) . . ?
C4 O2 C10 117.31(17) . . ?
H3A O3 H3B 102(4) . . ?
O1 N1 C1 118.85(16) . . ?
C9 N1 O1 119.85(17) . . ?
C9 N1 C1 121.30(18) . . ?
O2 C4 C3 114.26(17) . . ?
O2 C4 C5 125.06(19) . . ?
C5 C4 C3 120.67(18) . . ?
N1 C1 C6 119.13(17) . . ?
N1 C1 C2 119.98(18) . . ?
C2 C1 C6 120.90(18) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.14(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.47(18) . . ?
C6 C5 H5 120.3 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C8 C7 C6 119.32(19) . . ?
C1 C6 C5 118.96(17) . . ?
C1 C6 C7 118.94(18) . . ?
C5 C6 C7 122.10(19) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.84(19) . . ?
C3 C2 H2 120.6 . . ?
N1 C9 H9 119.6 . . ?
N1 C9 C8 120.84(19) . . ?
C8 C9 H9 119.6 . . ?
C7 C8 C9 120.43(18) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O4 0.80(4) 1.96(4) 2.757(3) 179(4) 1_554
O4 H4A O1 0.84(4) 1.88(4) 2.715(2) 175(4) .
O4 H4B O3 0.79(4) 1.97(4) 2.755(3) 176(4) 1_656
O3 H3B O1 0.84(4) 1.93(4) 2.767(2) 177(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
O1 N1 C1 C6 -177.26(17) . . . . ?
O1 N1 C1 C2 2.7(3) . . . . ?
O1 N1 C9 C8 178.52(18) . . . . ?
O2 C4 C3 C2 179.84(18) . . . . ?
O2 C4 C5 C6 179.65(18) . . . . ?
N1 C1 C6 C5 178.27(17) . . . . ?
N1 C1 C6 C7 -1.8(3) . . . . ?
N1 C1 C2 C3 -178.65(18) . . . . ?
N1 C9 C8 C7 -0.8(3) . . . . ?
C4 C3 C2 C1 0.1(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 -179.28(19) . . . . ?
C1 N1 C9 C8 -0.7(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 178.27(19) . . . . ?
C9 N1 C1 C6 1.9(3) . . . . ?
C9 N1 C1 C2 -178.13(18) . . . . ?
C8 C7 C6 C1 0.4(3) . . . . ?
C8 C7 C6 C5 -179.63(18) . . . . ?
C10 O2 C4 C3 179.26(18) . . . . ?
C10 O2 C4 C5 0.3(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1403a
_database_code_depnum_ccdc_archive 'CCDC 1474210'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2016-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '4-Methylquinoline N-Oxide Dihydrate'
_chemical_formula_moiety         'C10 H9 N O, 2(H2 O)'
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

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

_cell_length_a                   6.690(4)
_cell_length_b                   8.863(5)
_cell_length_c                   9.115(6)
_cell_angle_alpha                107.219(6)
_cell_angle_beta                 111.191(11)
_cell_angle_gamma                92.478(5)
_cell_volume                     474.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1460
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             208
_exptl_crystal_recrystallization_method 
'vapor diffusion with acetonitrile and hexanes'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2941
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.441
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
scan:
	Number of images: 182
	           Slice: -58.0000 - 33.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.5856
	          2theta: -34.7176
scan:
	Number of images: 150
	           Slice: -68.0000 - 7.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.5856
	          2theta: -34.7176
scan:
	Number of images: 114
	           Slice: -68.0000 - -11.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.5856
	          2theta: -34.7176
scan:
	Number of images: 110
	           Slice: -66.0000 - -11.0000
	     Image width: 0.5000
	        Exp time: 35.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 34.5856
	          2theta: -34.7176
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.121914
_diffrn_orient_matrix_UB_12      -0.068341
_diffrn_orient_matrix_UB_13      0.083188
_diffrn_orient_matrix_UB_21      -0.015310
_diffrn_orient_matrix_UB_22      0.053663
_diffrn_orient_matrix_UB_23      0.106049
_diffrn_orient_matrix_UB_31      -0.038943
_diffrn_orient_matrix_UB_32      -0.083792
_diffrn_orient_matrix_UB_33      0.083985
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1817
_reflns_number_total             2135
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C5(H5), C2(H2), C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54184(18) 0.33693(12) 0.09437(12) 0.0206(3) Uani 1 1 d . . . . .
O3 O 0.8595(2) -0.13273(17) 0.06888(16) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.6207(2) 0.36962(14) 0.25969(15) 0.0169(3) Uani 1 1 d . . . . .
O2 O 0.7222(2) 0.10343(15) -0.07098(16) 0.0368(3) Uani 1 1 d . . . . .
H2A H 0.6739 0.1805 -0.0206 0.055 Uiso 1 1 d G . . . .
H2B H 0.8371 0.1397 -0.0776 0.055 Uiso 1 1 d G . . . .
C9 C 0.6873(2) 0.52966(16) 0.36269(17) 0.0156(3) Uani 1 1 d . . . . .
C4 C 0.7756(2) 0.56552(17) 0.53855(17) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.6351(2) 0.25173(17) 0.32381(18) 0.0198(3) Uani 1 1 d . . . . .
H1 H 0.5870 0.1460 0.2527 0.024 Uiso 1 1 calc R . . . .
C3 C 0.7945(2) 0.43837(18) 0.60709(18) 0.0180(3) Uani 1 1 d . . . . .
C8 C 0.6641(2) 0.65058(18) 0.28981(18) 0.0190(3) Uani 1 1 d . . . . .
H8 H 0.6046 0.6247 0.1743 0.023 Uiso 1 1 calc R . . . .
C5 C 0.8417(2) 0.72985(18) 0.63876(18) 0.0193(3) Uani 1 1 d . . . . .
H5 H 0.9001 0.7580 0.7545 0.023 Uiso 1 1 calc R . . . .
C2 C 0.7216(2) 0.28463(17) 0.49689(19) 0.0198(3) Uani 1 1 d . . . . .
H2 H 0.7299 0.1999 0.5382 0.024 Uiso 1 1 calc R . . . .
C10 C 0.8889(3) 0.47153(19) 0.79230(18) 0.0218(3) Uani 1 1 d . . . . .
H10A H 1.0328 0.5325 0.8401 0.033 Uiso 1 1 calc GR . . . .
H10B H 0.8952 0.3720 0.8142 0.033 Uiso 1 1 calc GR . . . .
H10C H 0.7989 0.5313 0.8410 0.033 Uiso 1 1 calc GR . . . .
C7 C 0.7310(3) 0.80768(18) 0.39227(19) 0.0218(3) Uani 1 1 d . . . . .
H7 H 0.7170 0.8887 0.3455 0.026 Uiso 1 1 calc R . . . .
C6 C 0.8207(3) 0.84777(18) 0.56738(19) 0.0220(3) Uani 1 1 d . . . . .
H6 H 0.8659 0.9548 0.6350 0.026 Uiso 1 1 calc R . . . .
H3A H 0.741(4) -0.205(3) 0.017(3) 0.033 Uiso 1 1 d R . . . .
H3B H 0.797(3) -0.067(3) 0.042(3) 0.033 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3366(17) . ?
O3 H3A 0.88(2) . ?
O3 H3B 0.78(2) . ?
N1 C9 1.3952(19) . ?
N1 C1 1.3312(19) . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8500 . ?
C9 C4 1.420(2) . ?
C9 C8 1.405(2) . ?
C4 C3 1.431(2) . ?
C4 C5 1.420(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.401(2) . ?
C3 C2 1.372(2) . ?
C3 C10 1.502(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.373(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(2) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C6 1.410(2) . ?
C6 H6 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
H3A O3 H3B 92(2) . . ?
O1 N1 C9 118.43(11) . . ?
C1 N1 O1 120.51(12) . . ?
C1 N1 C9 121.06(13) . . ?
H2A O2 H2B 109.5 . . ?
N1 C9 C4 118.86(12) . . ?
N1 C9 C8 119.22(13) . . ?
C8 C9 C4 121.92(13) . . ?
C9 C4 C3 119.93(13) . . ?
C5 C4 C9 117.04(13) . . ?
C5 C4 C3 123.03(14) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 120.93(13) . . ?
C2 C1 H1 119.5 . . ?
C4 C3 C10 121.46(13) . . ?
C2 C3 C4 117.39(14) . . ?
C2 C3 C10 121.15(13) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 C9 118.76(14) . . ?
C7 C8 H8 120.6 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.97(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.81(13) . . ?
C3 C2 H2 119.1 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C7 H7 119.5 . . ?
C8 C7 C6 120.90(14) . . ?
C6 C7 H7 119.5 . . ?
C5 C6 C7 120.41(14) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 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
O1 N1 C9 C4 -178.70(12) . . . . ?
O1 N1 C9 C8 1.68(19) . . . . ?
O1 N1 C1 C2 178.70(13) . . . . ?
N1 C9 C4 C3 -0.1(2) . . . . ?
N1 C9 C4 C5 179.89(12) . . . . ?
N1 C9 C8 C7 -179.73(13) . . . . ?
N1 C1 C2 C3 0.1(2) . . . . ?
C9 N1 C1 C2 -1.3(2) . . . . ?
C9 C4 C3 C2 -1.0(2) . . . . ?
C9 C4 C3 C10 179.44(13) . . . . ?
C9 C4 C5 C6 -0.1(2) . . . . ?
C9 C8 C7 C6 -0.2(2) . . . . ?
C4 C9 C8 C7 0.7(2) . . . . ?
C4 C3 C2 C1 1.0(2) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C1 N1 C9 C4 1.3(2) . . . . ?
C1 N1 C9 C8 -178.36(13) . . . . ?
C3 C4 C5 C6 179.93(14) . . . . ?
C8 C9 C4 C3 179.49(13) . . . . ?
C8 C9 C4 C5 -0.5(2) . . . . ?
C8 C7 C6 C5 -0.3(2) . . . . ?
C5 C4 C3 C2 179.00(14) . . . . ?
C5 C4 C3 C10 -0.6(2) . . . . ?
C10 C3 C2 C1 -179.39(13) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1338a
_database_code_depnum_ccdc_archive 'CCDC 1474211'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2015-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        5,5'-Diphenyl-2,2'-bipyridine
_chemical_formula_moiety         '2(C11 H8 N)'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   20.260(12)
_cell_length_b                   5.434(3)
_cell_length_c                   16.088(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.528(9)
_cell_angle_gamma                90
_cell_volume                     1658.7(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4081
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8978
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.704
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -125.0000 - -2.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: -70.0000
	             Phi: 270.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 184
	           Slice: -68.0000 - 24.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 92
	           Slice: 0.0000 - 46.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 64
	           Slice: -45.0000 - -13.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.9568
	          2theta: -35.0367
scan:
	Number of images: 62
	           Slice: 19.0000 - 50.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.9568
	          2theta: -35.0367
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.006354
_diffrn_orient_matrix_UB_12      -0.064037
_diffrn_orient_matrix_UB_13      -0.016251
_diffrn_orient_matrix_UB_21      -0.156145
_diffrn_orient_matrix_UB_22      0.038233
_diffrn_orient_matrix_UB_23      -0.089604
_diffrn_orient_matrix_UB_31      0.023926
_diffrn_orient_matrix_UB_32      -0.009879
_diffrn_orient_matrix_UB_33      -0.045910
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2142
_reflns_number_total             2904
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+0.5500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1491
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: C21A(0.5) H21A(0.5) C21B(0.5) H21B(0.5) H20A(0.5) H20(0.5)
 C22A(0.5) H22A(0.5) C22B(0.5) H22B(0.5) C18B(0.5) H18B(0.5) C18A(0.5)
 H18A(0.5) C19B(0.5) H19B(0.5) C19A(0.5) H19A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C21A(H21A), C15(H15), C21B(H21B), C13(H13), C20(H20A), C20(H20), C14(H14),
 C2(H2), C11(H11), C9(H9), C4(H4), C3(H3), C10(H10), C7(H7), C8(H8), C22A(H22A),
  C22B(H22B), C18B(H18B), C18A(H18A), C19B(H19B), C19A(H19A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.05394(8) 0.1354(3) 0.44413(9) 0.0718(5) Uani 1 1 d . . . . .
C12 C -0.00253(10) 0.1013(4) 0.46758(11) 0.0719(6) Uani 1 1 d . . . . .
C21A C 0.2219(5) 0.1692(18) 0.3521(5) 0.112(3) Uani 0.5 1 d . . P A 2
H21A H 0.2516 0.0357 0.3560 0.134 Uiso 0.5 1 calc R . P A 2
C15 C -0.00550(12) 0.4685(6) 0.35134(15) 0.0955(7) Uani 1 1 d . . . . .
H15 H -0.0055 0.5927 0.3116 0.115 Uiso 1 1 calc R . . . .
C21B C 0.2383(4) 0.299(2) 0.3920(6) 0.148(4) Uani 0.5 1 d . . P A 1
H21B H 0.2804 0.2357 0.4309 0.177 Uiso 0.5 1 calc R . P A 1
C16 C 0.05275(11) 0.3177(4) 0.38658(12) 0.0755(6) Uani 1 1 d . . . . .
C17 C 0.11730(11) 0.3491(5) 0.36439(13) 0.0765(6) Uani 1 1 d . . . . .
C13 C -0.06205(11) 0.2466(5) 0.43495(14) 0.0922(7) Uani 1 1 d . . . . .
H13 H -0.1006 0.2198 0.4525 0.111 Uiso 1 1 calc R . . . .
C20 C 0.23927(15) 0.4101(7) 0.3241(2) 0.1168(10) Uani 1 1 d . . . . .
H20A H 0.2769 0.4284 0.3043 0.140 Uiso 0.5 1 calc R . P A 2
H20 H 0.2813 0.4331 0.3141 0.140 Uiso 0.5 1 calc R . P A 1
C14 C -0.06322(13) 0.4328(6) 0.37567(16) 0.1062(9) Uani 1 1 d . . . . .
H14 H -0.1028 0.5326 0.3526 0.127 Uiso 1 1 calc R . . . .
N1 N 0.44589(10) 0.8959(3) 0.39161(12) 0.0781(5) Uani 1 1 d . . . . .
C2 C 0.55683(13) 0.7388(5) 0.48662(15) 0.0874(7) Uani 1 1 d . . . . .
H2 H 0.5946 0.7480 0.5400 0.105 Uiso 1 1 calc R . . . .
C5 C 0.44481(12) 0.7212(4) 0.33107(14) 0.0778(6) Uani 1 1 d . . . . .
C1 C 0.50137(12) 0.9033(4) 0.46788(14) 0.0765(6) Uani 1 1 d . . . . .
C11 C 0.33464(14) 0.9140(6) 0.23125(17) 0.1033(8) Uani 1 1 d . . . . .
H11 H 0.3409 1.0362 0.2738 0.124 Uiso 1 1 calc R . . . .
C9 C 0.26705(16) 0.7505(8) 0.08975(19) 0.1185(10) Uani 1 1 d . . . . .
H9 H 0.2287 0.7584 0.0369 0.142 Uiso 1 1 calc R . . . .
C4 C 0.49818(14) 0.5517(5) 0.34660(16) 0.0909(7) Uani 1 1 d . . . . .
H4 H 0.4958 0.4313 0.3046 0.109 Uiso 1 1 calc R . . . .
C6 C 0.38273(12) 0.7280(4) 0.24723(15) 0.0812(6) Uani 1 1 d . . . . .
C3 C 0.55525(14) 0.5612(5) 0.42483(17) 0.0965(7) Uani 1 1 d . . . . .
H3 H 0.5921 0.4493 0.4357 0.116 Uiso 1 1 calc R . . . .
C10 C 0.27666(16) 0.9256(7) 0.1532(2) 0.1211(10) Uani 1 1 d . . . . .
H10 H 0.2444 1.0534 0.1443 0.145 Uiso 1 1 calc R . . . .
C7 C 0.37151(17) 0.5528(6) 0.1818(2) 0.1177(9) Uani 1 1 d . . . . .
H7 H 0.4034 0.4240 0.1899 0.141 Uiso 1 1 calc R . . . .
C8 C 0.3140(2) 0.5652(8) 0.1046(2) 0.1379(12) Uani 1 1 d . . . . .
H8 H 0.3073 0.4433 0.0618 0.165 Uiso 1 1 calc R . . . .
C22A C 0.1623(4) 0.1403(14) 0.3723(4) 0.0909(18) Uani 0.5 1 d . . P A 2
H22A H 0.1511 -0.0112 0.3908 0.109 Uiso 0.5 1 calc R . P A 2
C22B C 0.1783(3) 0.2662(16) 0.4117(5) 0.117(3) Uani 0.5 1 d . . P A 1
H22B H 0.1820 0.1781 0.4627 0.140 Uiso 0.5 1 calc R . P A 1
C18B C 0.1164(3) 0.4690(11) 0.2833(4) 0.0962(15) Uani 0.5 1 d . . P A 1
H18B H 0.0741 0.5277 0.2432 0.115 Uiso 0.5 1 calc R . P A 1
C18A C 0.1374(3) 0.5793(13) 0.3487(4) 0.1091(17) Uani 0.5 1 d . . P A 2
H18A H 0.1108 0.7160 0.3517 0.131 Uiso 0.5 1 calc R . P A 2
C19B C 0.1771(3) 0.4966(12) 0.2653(4) 0.1018(17) Uani 0.5 1 d . . P A 1
H19B H 0.1761 0.5737 0.2132 0.122 Uiso 0.5 1 calc R . P A 1
C19A C 0.1985(4) 0.6070(16) 0.3281(5) 0.128(2) Uani 0.5 1 d . . P A 2
H19A H 0.2119 0.7636 0.3168 0.153 Uiso 0.5 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C12 1.337(2) . ?
N2 C16 1.350(3) . ?
C12 C12 1.495(4) 3_556 ?
C12 C13 1.382(3) . ?
C21A H21A 0.9300 . ?
C21A C20 1.466(10) . ?
C21A C22A 1.367(11) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C15 C14 1.371(3) . ?
C21B H21B 0.9300 . ?
C21B C20 1.253(9) . ?
C21B C22B 1.371(10) . ?
C16 C17 1.481(3) . ?
C17 C22A 1.432(8) . ?
C17 C22B 1.284(7) . ?
C17 C18B 1.453(5) . ?
C17 C18A 1.366(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C20 H20A 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19B 1.367(6) . ?
C20 C19A 1.366(8) . ?
C14 H14 0.9300 . ?
N1 C5 1.355(3) . ?
N1 C1 1.343(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.384(3) . ?
C2 C3 1.378(3) . ?
C5 C4 1.375(3) . ?
C5 C6 1.488(3) . ?
C1 C1 1.489(4) 3_676 ?
C11 H11 0.9300 . ?
C11 C6 1.364(3) . ?
C11 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.359(4) . ?
C9 C8 1.347(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.379(3) . ?
C6 C7 1.379(3) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.374(4) . ?
C8 H8 0.9300 . ?
C22A H22A 0.9300 . ?
C22B H22B 0.9300 . ?
C18B H18B 0.9300 . ?
C18B C19B 1.367(7) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.398(8) . ?
C19B H19B 0.9300 . ?
C19A H19A 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
C12 N2 C16 118.94(18) . . ?
N2 C12 C12 116.3(2) . 3_556 ?
N2 C12 C13 122.2(2) . . ?
C13 C12 C12 121.5(2) . 3_556 ?
C20 C21A H21A 119.9 . . ?
C22A C21A H21A 119.9 . . ?
C22A C21A C20 120.2(7) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.3(2) . . ?
C20 C21B H21B 118.3 . . ?
C20 C21B C22B 123.4(7) . . ?
C22B C21B H21B 118.3 . . ?
N2 C16 C15 121.5(2) . . ?
N2 C16 C17 116.41(19) . . ?
C15 C16 C17 122.1(2) . . ?
C22A C17 C16 118.4(3) . . ?
C22B C17 C16 124.3(3) . . ?
C22B C17 C18B 113.3(4) . . ?
C18B C17 C16 122.3(3) . . ?
C18A C17 C16 119.7(3) . . ?
C18A C17 C22A 121.3(4) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
C21A C20 H20A 120.9 . . ?
C21B C20 H20 120.8 . . ?
C21B C20 C19B 118.5(5) . . ?
C19B C20 H20 120.8 . . ?
C19A C20 C21A 118.1(5) . . ?
C19A C20 H20A 120.9 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C1 N1 C5 118.37(19) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C3 C2 C1 118.9(2) . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 115.5(2) . . ?
C4 C5 C6 122.9(2) . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 C1 115.6(3) . 3_676 ?
C2 C1 C1 122.0(3) . 3_676 ?
C6 C11 H11 119.1 . . ?
C6 C11 C10 121.8(3) . . ?
C10 C11 H11 119.1 . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.9(3) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C11 C6 C5 120.7(2) . . ?
C11 C6 C7 116.9(2) . . ?
C7 C6 C5 122.4(2) . . ?
C2 C3 C4 119.0(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C21A C22A C17 118.4(7) . . ?
C21A C22A H22A 120.8 . . ?
C17 C22A H22A 120.8 . . ?
C21B C22B H22B 117.8 . . ?
C17 C22B C21B 124.3(6) . . ?
C17 C22B H22B 117.8 . . ?
C17 C18B H18B 119.6 . . ?
C19B C18B C17 120.8(4) . . ?
C19B C18B H18B 119.6 . . ?
C17 C18A H18A 120.4 . . ?
C17 C18A C19A 119.3(6) . . ?
C19A C18A H18A 120.4 . . ?
C20 C19B H19B 120.2 . . ?
C18B C19B C20 119.6(5) . . ?
C18B C19B H19B 120.2 . . ?
C20 C19A C18A 121.8(6) . . ?
C20 C19A H19A 119.1 . . ?
C18A C19A H19A 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C12 C13 C14 0.3(3) . . . . ?
N2 C16 C17 C22A 25.5(4) . . . . ?
N2 C16 C17 C22B -19.6(6) . . . . ?
N2 C16 C17 C18B 157.4(4) . . . . ?
N2 C16 C17 C18A -145.7(4) . . . . ?
C12 N2 C16 C15 -0.2(3) . . . . ?
C12 N2 C16 C17 178.97(17) . . . . ?
C12 C12 C13 C14 179.4(2) 3_556 . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C21A C20 C19A C18A -6.9(10) . . . . ?
C15 C16 C17 C22A -155.3(3) . . . . ?
C15 C16 C17 C22B 159.5(6) . . . . ?
C15 C16 C17 C18B -23.4(5) . . . . ?
C15 C16 C17 C18A 33.4(4) . . . . ?
C21B C20 C19B C18B 2.6(11) . . . . ?
C16 N2 C12 C12 -179.2(2) . . . 3_556 ?
C16 N2 C12 C13 -0.1(3) . . . . ?
C16 C15 C14 C13 0.0(4) . . . . ?
C16 C17 C22A C21A -179.9(5) . . . . ?
C16 C17 C22B C21B -178.8(8) . . . . ?
C16 C17 C18B C19B 179.5(5) . . . . ?
C16 C17 C18A C19A 179.8(5) . . . . ?
C17 C18B C19B C20 0.1(10) . . . . ?
C17 C18A C19A C20 -0.7(11) . . . . ?
C20 C21A C22A C17 0.8(9) . . . . ?
C20 C21B C22B C17 -1.5(18) . . . . ?
C14 C15 C16 N2 0.3(4) . . . . ?
C14 C15 C16 C17 -178.9(2) . . . . ?
N1 C5 C4 C3 -1.4(3) . . . . ?
N1 C5 C6 C11 5.9(3) . . . . ?
N1 C5 C6 C7 -175.5(2) . . . . ?
C5 N1 C1 C2 -0.3(3) . . . . ?
C5 N1 C1 C1 -178.9(2) . . . 3_676 ?
C5 C4 C3 C2 1.1(4) . . . . ?
C5 C6 C7 C8 -179.4(3) . . . . ?
C1 N1 C5 C4 0.9(3) . . . . ?
C1 N1 C5 C6 -178.47(17) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C11 C6 C7 C8 -0.7(4) . . . . ?
C4 C5 C6 C11 -173.5(2) . . . . ?
C4 C5 C6 C7 5.1(3) . . . . ?
C6 C5 C4 C3 178.0(2) . . . . ?
C6 C11 C10 C9 -0.8(4) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C3 C2 C1 N1 0.1(3) . . . . ?
C3 C2 C1 C1 178.7(2) . . . 3_676 ?
C10 C11 C6 C5 179.4(2) . . . . ?
C10 C11 C6 C7 0.6(4) . . . . ?
C10 C9 C8 C7 -1.0(5) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C22A C21A C20 C19A 6.8(10) . . . . ?
C22A C17 C18A C19A 8.8(8) . . . . ?
C22B C21B C20 C19B -2.1(15) . . . . ?
C22B C17 C18B C19B -3.2(9) . . . . ?
C18B C17 C22B C21B 4.0(12) . . . . ?
C18A C17 C22A C21A -8.7(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-26
_olex2_date_sample_submission    2015-06-25
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1341f
_database_code_depnum_ccdc_archive 'CCDC 1474212'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2015-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        "6,6'-Di-tert-butyl-2,2'-biquinoline "
_chemical_formula_moiety         'C26 H28 N2'
_chemical_formula_sum            'C26 H28 N2'
_chemical_formula_weight         368.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.301(11)
_cell_length_b                   6.133(3)
_cell_length_c                   18.738(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.032(6)
_cell_angle_gamma                90
_cell_volume                     2098(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2763
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6151
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         3.008
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 188
	           Slice: -50.0000 - 44.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 0.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 94
	           Slice: -70.0000 - -23.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 88
	           Slice: -56.0000 - -12.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 34.9591
	          2theta: -35.0597
scan:
	Number of images: 62
	           Slice: -115.0000 - -84.0000
	     Image width: 0.5000
	        Exp time: 50.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 270.0000
	             XTD: 34.9591
	          2theta: -35.0597
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.050853
_diffrn_orient_matrix_UB_12      0.016597
_diffrn_orient_matrix_UB_13      -0.011794
_diffrn_orient_matrix_UB_21      0.059553
_diffrn_orient_matrix_UB_22      0.138756
_diffrn_orient_matrix_UB_23      -0.061512
_diffrn_orient_matrix_UB_31      0.000186
_diffrn_orient_matrix_UB_32      -0.021748
_diffrn_orient_matrix_UB_33      -0.048878
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1474
_reflns_number_total             1924
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+2.7500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1458
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33464(10) 0.3935(3) 0.26677(9) 0.0499(5) Uani 1 1 d . . . . .
C9 C 0.40081(11) 0.3710(4) 0.30424(10) 0.0462(5) Uani 1 1 d . . . . .
C1 C 0.28591(11) 0.2368(4) 0.27088(10) 0.0477(5) Uani 1 1 d . . . . .
C4 C 0.41890(11) 0.1856(4) 0.34739(10) 0.0469(5) Uani 1 1 d . . . . .
C5 C 0.48863(12) 0.1738(4) 0.38436(11) 0.0494(5) Uani 1 1 d . . . . .
H5 H 0.5001 0.0512 0.4121 0.059 Uiso 1 1 calc R . . . .
C6 C 0.54016(12) 0.3346(4) 0.38122(10) 0.0467(5) Uani 1 1 d . . . . .
C7 C 0.52033(13) 0.5187(4) 0.33790(12) 0.0544(6) Uani 1 1 d . . . . .
H7 H 0.5539 0.6317 0.3349 0.065 Uiso 1 1 calc R . . . .
C8 C 0.45378(13) 0.5352(4) 0.30067(12) 0.0552(6) Uani 1 1 d . . . . .
H8 H 0.4433 0.6575 0.2724 0.066 Uiso 1 1 calc R . . . .
C3 C 0.36529(13) 0.0217(4) 0.34948(12) 0.0579(6) Uani 1 1 d . . . . .
H3 H 0.3750 -0.1034 0.3766 0.070 Uiso 1 1 calc R . . . .
C10 C 0.61410(12) 0.3256(4) 0.42341(11) 0.0517(6) Uani 1 1 d . . . . .
C2 C 0.29971(13) 0.0451(4) 0.31228(12) 0.0569(6) Uani 1 1 d . . . . .
H2 H 0.2641 -0.0627 0.3138 0.068 Uiso 1 1 calc R . . . .
C12 C 0.60868(15) 0.4558(5) 0.49313(13) 0.0767(8) Uani 1 1 d . . . . .
H12A H 0.5946 0.6032 0.4818 0.115 Uiso 1 1 calc GR . . . .
H12B H 0.6554 0.4554 0.5199 0.115 Uiso 1 1 calc GR . . . .
H12C H 0.5727 0.3899 0.5212 0.115 Uiso 1 1 calc GR . . . .
C11 C 0.67446(14) 0.4263(5) 0.38093(16) 0.0765(8) Uani 1 1 d . . . . .
H11A H 0.6731 0.3618 0.3342 0.115 Uiso 1 1 calc GR . . . .
H11B H 0.7214 0.3995 0.4056 0.115 Uiso 1 1 calc GR . . . .
H11C H 0.6667 0.5807 0.3765 0.115 Uiso 1 1 calc GR . . . .
C13 C 0.63708(15) 0.0917(5) 0.44215(16) 0.0789(8) Uani 1 1 d . . . . .
H13A H 0.6029 0.0289 0.4728 0.118 Uiso 1 1 calc GR . . . .
H13B H 0.6851 0.0922 0.4663 0.118 Uiso 1 1 calc GR . . . .
H13C H 0.6377 0.0071 0.3991 0.118 Uiso 1 1 calc GR . . . .


_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 C9 1.363(3) . ?
N1 C1 1.317(3) . ?
C9 C4 1.421(3) . ?
C9 C8 1.403(3) . ?
C1 C1 1.490(4) 7 ?
C1 C2 1.421(3) . ?
C4 C5 1.410(3) . ?
C4 C3 1.407(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(3) . ?
C6 C7 1.423(3) . ?
C6 C10 1.519(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.364(3) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.352(3) . ?
C10 C12 1.540(3) . ?
C10 C11 1.536(3) . ?
C10 C13 1.529(4) . ?
C2 H2 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C1 N1 C9 118.46(19) . . ?
N1 C9 C4 122.5(2) . . ?
N1 C9 C8 119.63(19) . . ?
C8 C9 C4 117.9(2) . . ?
N1 C1 C1 117.8(2) . 7 ?
N1 C1 C2 122.7(2) . . ?
C2 C1 C1 119.5(3) . 7 ?
C5 C4 C9 119.1(2) . . ?
C5 C4 C3 123.9(2) . . ?
C3 C4 C9 116.9(2) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 C4 123.0(2) . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C7 116.6(2) . . ?
C5 C6 C10 122.8(2) . . ?
C7 C6 C10 120.5(2) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
C9 C8 H8 119.4 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.8 . . ?
C6 C10 C12 108.32(18) . . ?
C6 C10 C11 111.24(19) . . ?
C6 C10 C13 112.0(2) . . ?
C11 C10 C12 108.8(2) . . ?
C13 C10 C12 108.9(2) . . ?
C13 C10 C11 107.5(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
N1 C9 C4 C5 179.77(18) . . . . ?
N1 C9 C4 C3 0.7(3) . . . . ?
N1 C9 C8 C7 179.5(2) . . . . ?
N1 C1 C2 C3 0.4(3) . . . . ?
C9 N1 C1 C1 -179.5(2) . . . 7 ?
C9 N1 C1 C2 -0.5(3) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C9 C4 C3 C2 -0.8(3) . . . . ?
C1 N1 C9 C4 -0.1(3) . . . . ?
C1 N1 C9 C8 179.84(19) . . . . ?
C1 C1 C2 C3 179.4(2) 7 . . . ?
C4 C9 C8 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C10 177.52(19) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C5 C4 C3 C2 -179.8(2) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C5 C6 C10 C12 -95.8(3) . . . . ?
C5 C6 C10 C11 144.6(2) . . . . ?
C5 C6 C10 C13 24.3(3) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C6 C10 C12 81.8(2) . . . . ?
C7 C6 C10 C11 -37.7(3) . . . . ?
C7 C6 C10 C13 -158.0(2) . . . . ?
C8 C9 C4 C5 -0.1(3) . . . . ?
C8 C9 C4 C3 -179.23(19) . . . . ?
C3 C4 C5 C6 179.6(2) . . . . ?
C10 C6 C7 C8 -178.3(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd1360a
_database_code_depnum_ccdc_archive 'CCDC 1474213'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;
_audit_creation_date             2015-08-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '3-Methylisoquinoline N-Oxide Dihydrate'
_chemical_formula_moiety         'C10 H9 N O, 2(H2 O)'
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

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

_cell_length_a                   6.8201(14)
_cell_length_b                   16.879(3)
_cell_length_c                   9.0566(19)
_cell_angle_alpha                90
_cell_angle_beta                 106.250(3)
_cell_angle_gamma                90
_cell_volume                     1000.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3408
_cell_measurement_temperature    293
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method 
'slow evaporation of acetonitrile and hexanes'
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5302
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.043
_diffrn_reflns_theta_max         25.043
_diffrn_reflns_theta_min         3.111
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 246
	           Slice: -68.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 270.0000
	             XTD: 34.9601
	          2theta: -35.0156
scan:
	Number of images: 118
	           Slice: -67.0000 - -8.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 90.0000
	             XTD: 34.9601
	          2theta: -35.0156
scan:
	Number of images: 90
	           Slice: -68.0000 - -23.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 70.0000
	             Phi: 180.0000
	             XTD: 34.9601
	          2theta: -35.0156
scan:
	Number of images: 90
	           Slice: -125.0000 - -80.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 34.9601
	          2theta: -35.0156
scan:
	Number of images: 64
	           Slice: -66.0000 - -34.0000
	     Image width: 0.5000
	        Exp time: 40.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 90.0000
	             XTD: 34.9601
	          2theta: -35.0156
;
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.140040
_diffrn_orient_matrix_UB_12      -0.041935
_diffrn_orient_matrix_UB_13      0.044225
_diffrn_orient_matrix_UB_21      0.000043
_diffrn_orient_matrix_UB_22      -0.043058
_diffrn_orient_matrix_UB_23      -0.040692
_diffrn_orient_matrix_UB_31      0.014551
_diffrn_orient_matrix_UB_32      -0.078354
_diffrn_orient_matrix_UB_33      0.082925
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1611
_reflns_number_total             1743
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.1020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74468(13) 0.26688(6) 0.65889(11) 0.0511(3) Uani 1 1 d . . . . .
O2 O 0.34980(18) 0.20981(7) 0.53331(14) 0.0621(3) Uani 1 1 d . . . . .
O3 O 0.14516(19) 0.20872(7) 0.76147(12) 0.0625(3) Uani 1 1 d . . . . .
N1 N 0.74951(14) 0.34111(6) 0.60956(12) 0.0392(3) Uani 1 1 d . . . . .
C7 C 0.75128(15) 0.49591(7) 0.50738(14) 0.0363(3) Uani 1 1 d . . . . .
C2 C 0.71532(16) 0.43209(7) 0.40247(13) 0.0369(3) Uani 1 1 d . . . . .
C8 C 0.78779(17) 0.47777(8) 0.66519(14) 0.0401(3) Uani 1 1 d . . . . .
C1 C 0.71596(18) 0.35508(8) 0.45958(14) 0.0404(3) Uani 1 1 d . . . . .
C9 C 0.78793(17) 0.40197(8) 0.71667(14) 0.0412(3) Uani 1 1 d . . . . .
C6 C 0.75111(17) 0.57401(7) 0.45174(16) 0.0431(3) Uani 1 1 d . . . . .
C3 C 0.68036(19) 0.44730(8) 0.24315(15) 0.0456(3) Uani 1 1 d . . . . .
C4 C 0.6812(2) 0.52350(9) 0.19343(16) 0.0494(4) Uani 1 1 d . . . . .
C5 C 0.71674(19) 0.58708(8) 0.29802(17) 0.0479(4) Uani 1 1 d . . . . .
C10 C 0.8293(3) 0.37903(12) 0.88120(17) 0.0593(4) Uani 1 1 d . . . . .
H6 H 0.777(3) 0.6179(12) 0.526(2) 0.071 Uiso 1 1 d R . . . .
H1 H 0.695(3) 0.3083(12) 0.392(2) 0.071 Uiso 1 1 d R . . . .
H8 H 0.814(3) 0.5213(12) 0.742(2) 0.071 Uiso 1 1 d R . . . .
H3 H 0.654(3) 0.4025(11) 0.170(2) 0.071 Uiso 1 1 d R . . . .
H5 H 0.719(3) 0.6401(12) 0.263(2) 0.071 Uiso 1 1 d R . . . .
H10A H 0.711(3) 0.3522(13) 0.896(3) 0.089 Uiso 1 1 d R . . . .
H4 H 0.655(3) 0.5373(11) 0.085(2) 0.071 Uiso 1 1 d R . . . .
H3A H 0.211(3) 0.2079(14) 0.688(3) 0.089 Uiso 1 1 d R . . . .
H3B H 0.019(4) 0.2241(13) 0.721(3) 0.089 Uiso 1 1 d R . . . .
H10B H 0.857(3) 0.4294(13) 0.946(2) 0.089 Uiso 1 1 d R . . . .
H10C H 0.946(3) 0.3459(13) 0.912(2) 0.089 Uiso 1 1 d R . . . .
H2A H 0.292(3) 0.2363(14) 0.446(3) 0.089 Uiso 1 1 d R . . . .
H2B H 0.476(4) 0.2308(12) 0.575(3) 0.089 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3338(14) . ?
O2 H2A 0.89(3) . ?
O2 H2B 0.91(2) . ?
O3 H3A 0.90(3) . ?
O3 H3B 0.88(2) . ?
N1 C1 1.3338(17) . ?
N1 C9 1.3866(17) . ?
C7 C2 1.4117(17) . ?
C7 C8 1.4139(18) . ?
C7 C6 1.4111(18) . ?
C2 C1 1.3986(18) . ?
C2 C3 1.4185(18) . ?
C8 C9 1.3617(19) . ?
C8 H8 0.993(19) . ?
C1 H1 0.98(2) . ?
C9 C10 1.4882(19) . ?
C6 C5 1.364(2) . ?
C6 H6 0.98(2) . ?
C3 C4 1.363(2) . ?
C3 H3 0.99(2) . ?
C4 C5 1.407(2) . ?
C4 H4 0.973(18) . ?
C5 H5 0.95(2) . ?
C10 H10A 0.97(2) . ?
C10 H10B 1.02(2) . ?
C10 H10C 0.95(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
H2A O2 H2B 107.6(19) . . ?
H3A O3 H3B 109(2) . . ?
O1 N1 C1 119.59(11) . . ?
O1 N1 C9 118.63(10) . . ?
C1 N1 C9 121.77(11) . . ?
C2 C7 C8 117.60(12) . . ?
C6 C7 C2 119.33(11) . . ?
C6 C7 C8 123.06(11) . . ?
C7 C2 C3 119.64(12) . . ?
C1 C2 C7 118.58(11) . . ?
C1 C2 C3 121.78(11) . . ?
C7 C8 H8 119.6(11) . . ?
C9 C8 C7 122.18(12) . . ?
C9 C8 H8 118.2(11) . . ?
N1 C1 C2 121.52(11) . . ?
N1 C1 H1 116.3(11) . . ?
C2 C1 H1 122.2(11) . . ?
N1 C9 C10 116.97(13) . . ?
C8 C9 N1 118.34(11) . . ?
C8 C9 C10 124.69(13) . . ?
C7 C6 H6 118.5(12) . . ?
C5 C6 C7 119.90(12) . . ?
C5 C6 H6 121.6(12) . . ?
C2 C3 H3 119.5(11) . . ?
C4 C3 C2 119.45(13) . . ?
C4 C3 H3 121.0(11) . . ?
C3 C4 C5 120.88(13) . . ?
C3 C4 H4 122.8(12) . . ?
C5 C4 H4 116.3(12) . . ?
C6 C5 C4 120.79(13) . . ?
C6 C5 H5 118.4(11) . . ?
C4 C5 H5 120.8(11) . . ?
C9 C10 H10A 109.4(13) . . ?
C9 C10 H10B 108.3(12) . . ?
C9 C10 H10C 111.1(13) . . ?
H10A C10 H10B 109.4(17) . . ?
H10A C10 H10C 110.2(17) . . ?
H10B C10 H10C 108.5(16) . . ?

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 N1 C1 C2 178.63(9) . . . . ?
O1 N1 C9 C8 -178.44(9) . . . . ?
O1 N1 C9 C10 2.33(16) . . . . ?
C7 C2 C1 N1 0.01(18) . . . . ?
C7 C2 C3 C4 -0.26(18) . . . . ?
C7 C8 C9 N1 -0.42(17) . . . . ?
C7 C8 C9 C10 178.74(11) . . . . ?
C7 C6 C5 C4 0.02(19) . . . . ?
C2 C7 C8 C9 -0.34(17) . . . . ?
C2 C7 C6 C5 -0.11(18) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C8 C7 C2 C1 0.54(16) . . . . ?
C8 C7 C2 C3 -179.25(10) . . . . ?
C8 C7 C6 C5 179.34(10) . . . . ?
C1 N1 C9 C8 1.01(17) . . . . ?
C1 N1 C9 C10 -178.22(11) . . . . ?
C1 C2 C3 C4 179.96(11) . . . . ?
C9 N1 C1 C2 -0.81(18) . . . . ?
C6 C7 C2 C1 -179.98(10) . . . . ?
C6 C7 C2 C3 0.23(17) . . . . ?
C6 C7 C8 C9 -179.79(10) . . . . ?
C3 C2 C1 N1 179.80(10) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
