# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ab50716_tw
_database_code_depnum_ccdc_archive 'CCDC 1577318'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '2-Methylbenzylammonium Formate'
_chemical_formula_moiety         'C H O2, C8 H12 N'
_chemical_formula_sum            'C9 H13 N O2'
_chemical_formula_weight         167.20
_chemical_absolute_configuration ?
_chemical_melting_point          391.15-397.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.9761(6)
_cell_length_b                   7.6181(6)
_cell_length_c                   8.3283(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.646(4)
_cell_angle_gamma                90
_cell_volume                     441.15(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8321
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      34.15
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1286 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8935. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.92
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.192
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3310
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.207
_diffrn_reflns_theta_min         2.454
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.888
_reflns_number_gt                3234
_reflns_number_total             3310
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Flack x determined using 1441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      1.114
_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)+(0.1620P)²+0.0330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2041
_refine_special_details          'Refined as a 2-component perfect twin.,Twin'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 N7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_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
O O 0.4838(2) 0.6881(2) 0.4989(2) 0.0187(3) Uani 1 1 d . . . . .
O1 O 0.1638(2) 0.7126(2) 0.4837(2) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.3319(3) 0.7740(3) 0.4782(2) 0.0139(4) Uani 1 1 d . . . . .
H2 H 0.3428 0.8932 0.4569 0.017 Uiso 1 1 calc R . . . .
C3 C 0.2318(3) 0.2412(3) 0.8634(3) 0.0138(4) Uani 1 1 d . . . . .
C4 C 0.2636(3) 0.2621(3) 1.0331(3) 0.0159(4) Uani 1 1 d . . . . .
C5 C 0.2094(3) 0.0738(3) 0.7981(3) 0.0148(4) Uani 1 1 d . . . . .
H5 H 0.1890 0.0607 0.6870 0.018 Uiso 1 1 calc R . . . .
C6 C 0.2474(3) -0.0557(3) 1.0636(3) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.2522 -0.1537 1.1305 0.023 Uiso 1 1 calc R . . . .
N7 N 0.1931(2) 0.3709(2) 0.5852(2) 0.0147(3) Uani 1 1 d . . . . .
H7A H 0.1888 0.4724 0.5321 0.018 Uiso 1 1 calc GR . . . .
H7B H 0.0827 0.3138 0.5642 0.018 Uiso 1 1 calc GR . . . .
H7C H 0.2895 0.3061 0.5539 0.018 Uiso 1 1 calc GR . . . .
C8 C 0.2241(3) 0.4054(3) 0.7621(3) 0.0152(4) Uani 1 1 d . . . . .
H8A H 0.1209 0.4795 0.7942 0.018 Uiso 1 1 calc R . . . .
H8B H 0.3437 0.4693 0.7835 0.018 Uiso 1 1 calc R . . . .
C9 C 0.2168(3) -0.0751(3) 0.8962(3) 0.0185(4) Uani 1 1 d . . . . .
H9 H 0.2016 -0.1862 0.8508 0.022 Uiso 1 1 calc R . . . .
C10 C 0.2705(3) 0.1122(3) 1.1284(3) 0.0186(4) Uani 1 1 d . . . . .
H10 H 0.2912 0.1244 1.2396 0.022 Uiso 1 1 calc R . . . .
C11 C 0.2860(3) 0.4416(3) 1.1072(3) 0.0206(4) Uani 1 1 d . . . . .
H11A H 0.3827 0.5057 1.0559 0.031 Uiso 1 1 calc GR . . . .
H11B H 0.3239 0.4305 1.2202 0.031 Uiso 1 1 calc GR . . . .
H11C H 0.1659 0.5033 1.0929 0.031 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
O C2 1.245(2) . ?
O1 C2 1.267(2) . ?
C3 C4 1.422(3) . ?
C3 C5 1.390(3) . ?
C3 C8 1.507(3) . ?
C4 C10 1.390(3) . ?
C4 C11 1.503(3) . ?
C5 C9 1.396(3) . ?
C6 C9 1.401(3) . ?
C6 C10 1.393(3) . ?
N7 C8 1.495(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O C2 O1 125.5(2) . . ?
C4 C3 C8 117.32(18) . . ?
C5 C3 C4 119.69(19) . . ?
C5 C3 C8 123.00(18) . . ?
C3 C4 C11 120.87(19) . . ?
C10 C4 C3 118.1(2) . . ?
C10 C4 C11 121.01(19) . . ?
C3 C5 C9 121.24(19) . . ?
C10 C6 C9 119.1(2) . . ?
N7 C8 C3 113.70(17) . . ?
C5 C9 C6 119.5(2) . . ?
C4 C10 C6 122.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_ab51517
_database_code_depnum_ccdc_archive 'CCDC 1577319'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '4-Methoxybenzylammonium Formate'
_chemical_formula_moiety         'C H O2, C8 H12 N O'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_chemical_absolute_configuration ?
_chemical_melting_point          388.15-390.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   6.7615(3)
_cell_length_b                   18.9173(7)
_cell_length_c                   7.8044(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.9340(19)
_cell_angle_gamma                90
_cell_volume                     959.90(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7572
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.70
_cell_measurement_theta_min      3.31
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0968 before and 0.0370 after correction. The Ratio of minimum to maximum transmission is 0.9051. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.725
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.128
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11804
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.702
_diffrn_reflns_theta_min         2.153
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3159
_reflns_number_total             3233
_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       'SAINT V8.38A'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1526 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.051
_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)+(0.0520P)²+0.0780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0747
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_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
O O 1.47917(13) 0.28755(5) 1.59135(11) 0.01740(17) Uani 1 1 d . . . . .
O0AA O 1.81156(14) 0.28707(5) 1.59626(13) 0.02304(19) Uani 1 1 d . . . . .
O1AA O 0.23378(13) 0.44755(5) 0.97090(11) 0.01883(17) Uani 1 1 d . . . . .
N1AA N 1.07990(15) 0.30342(5) 1.38541(13) 0.01583(17) Uani 1 1 d . . . . .
H1AA H 1.216(3) 0.2956(9) 1.449(3) 0.020(4) Uiso 1 1 d . . . . .
H1AB H 1.001(3) 0.3008(11) 1.454(3) 0.023(5) Uiso 1 1 d . . . . .
H1AC H 1.053(3) 0.2713(11) 1.306(3) 0.021(4) Uiso 1 1 d . . . . .
C C 0.5320(2) 0.45665(6) 1.20956(15) 0.0191(2) Uani 1 1 d . . . . .
H H 0.458(3) 0.4863(11) 1.268(3) 0.030(5) Uiso 1 1 d . . . . .
C1 C 0.43517(17) 0.42799(5) 1.04247(14) 0.01465(19) Uani 1 1 d . . . . .
C2 C 0.74901(18) 0.36817(6) 1.04298(15) 0.0168(2) Uani 1 1 d . . . . .
H2 H 0.829(3) 0.3370(10) 0.989(2) 0.020(4) Uiso 1 1 d . . . . .
C3 C 1.06674(17) 0.37536(7) 1.30283(15) 0.0197(2) Uani 1 1 d . . . . .
H3A H 1.150(3) 0.3744(10) 1.223(3) 0.019(4) Uiso 1 1 d . . . . .
H3B H 1.130(3) 0.4080(11) 1.400(3) 0.023(4) Uiso 1 1 d . . . . .
C4 C 0.84806(17) 0.39550(6) 1.21063(14) 0.0164(2) Uani 1 1 d . . . . .
C5 C 0.73664(19) 0.44042(6) 1.29225(15) 0.0192(2) Uani 1 1 d . . . . .
H5 H 0.792(3) 0.4606(11) 1.406(3) 0.028(5) Uiso 1 1 d . . . . .
C6 C 1.62544(18) 0.29373(6) 1.51979(15) 0.0160(2) Uani 1 1 d . . . . .
H6 H 1.586(3) 0.3057(10) 1.397(3) 0.018(4) Uiso 1 1 d . . . . .
C7 C 0.54361(17) 0.38362(6) 0.95825(14) 0.01577(19) Uani 1 1 d . . . . .
H7 H 0.485(3) 0.3646(10) 0.846(3) 0.019(4) Uiso 1 1 d . . . . .
C8 C 0.12319(19) 0.41214(7) 0.81134(17) 0.0225(2) Uani 1 1 d . . . . .
H8A H -0.015(4) 0.4266(13) 0.787(3) 0.044(6) Uiso 1 1 d . . . . .
H8B H 0.180(3) 0.4234(12) 0.711(3) 0.029(5) Uiso 1 1 d . . . . .
H8C H 0.127(4) 0.3622(12) 0.831(3) 0.030(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C6 1.2676(14) . ?
O0AA C6 1.2424(15) . ?
O1AA C1 1.3731(13) . ?
O1AA C8 1.4308(15) . ?
N1AA C3 1.4979(16) . ?
C C1 1.3980(15) . ?
C C5 1.3908(17) . ?
C1 C7 1.3924(15) . ?
C2 C4 1.3953(15) . ?
C2 C7 1.3954(15) . ?
C3 C4 1.5050(16) . ?
C4 C5 1.3995(17) . ?

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 O1AA C8 116.80(9) . . ?
C5 C C1 119.92(10) . . ?
O1AA C1 C 115.68(10) . . ?
O1AA C1 C7 124.22(9) . . ?
C7 C1 C 120.10(10) . . ?
C4 C2 C7 121.72(10) . . ?
N1AA C3 C4 111.73(9) . . ?
C2 C4 C3 120.68(10) . . ?
C2 C4 C5 118.17(10) . . ?
C5 C4 C3 121.13(10) . . ?
C C5 C4 120.93(10) . . ?
O0AA C6 O 126.08(10) . . ?
C1 C7 C2 119.15(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate'
####################################################################### 
# 
# 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_ab57316a
_database_code_depnum_ccdc_archive 'CCDC 1577323'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '3-Chlorobenzylammonium Formate'
_chemical_formula_moiety         'C7 H9 Cl N, C H O2'
_chemical_formula_sum            'C8 H10 Cl N O2'
_chemical_formula_weight         187.62
_chemical_melting_point          373.15-376.15
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.7899(10)
_cell_length_b                   4.7766(3)
_cell_length_c                   11.5500(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.162(3)
_cell_angle_gamma                90
_cell_volume                     898.14(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9597
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.60
_cell_measurement_theta_min      3.54
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0549 before and 0.0441 after correction. The Ratio of minimum to maximum transmission is 0.9346. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20616
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.650
_diffrn_reflns_theta_min         2.502
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2789
_reflns_number_total             2991
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.143
_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)+(0.0360P)²+0.9640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_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
Cl1 Cl 0.04203(2) 0.27410(9) 0.16279(4) 0.02444(11) Uani 1 1 d . . . . .
N N 0.38570(7) 0.8587(3) 0.17787(10) 0.0132(2) Uani 1 1 d . . . . .
HA H 0.4023(14) 0.683(5) 0.205(2) 0.029(6) Uiso 1 1 d . . . . .
HB H 0.4155(13) 0.994(5) 0.2218(19) 0.024(5) Uiso 1 1 d . . . . .
HC H 0.3911(14) 0.866(5) 0.099(2) 0.028(6) Uiso 1 1 d . . . . .
C C 0.12150(8) 0.3873(3) 0.10175(13) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.24158(8) 0.6742(3) 0.11737(11) 0.0132(2) Uani 1 1 d . . . . .
C2 C 0.29915(8) 0.8945(3) 0.18414(12) 0.0144(2) Uani 1 1 d . . . . .
H2A H 0.2981(13) 0.892(4) 0.2651(19) 0.019(5) Uiso 1 1 d . . . . .
H2B H 0.2809(12) 1.083(4) 0.1490(18) 0.019(5) Uiso 1 1 d . . . . .
C3 C 0.17696(8) 0.5838(3) 0.16426(12) 0.0146(2) Uani 1 1 d . . . . .
H3 H 0.1696(12) 0.657(4) 0.2391(18) 0.018(5) Uiso 1 1 d . . . . .
C4 C 0.12825(9) 0.2775(3) -0.00650(13) 0.0190(3) Uani 1 1 d . . . . .
H4 H 0.0898(15) 0.147(5) -0.047(2) 0.035(6) Uiso 1 1 d . . . . .
C6 C 0.24910(9) 0.5657(3) 0.00837(13) 0.0182(3) Uani 1 1 d . . . . .
H6 H 0.2959(13) 0.623(5) -0.0270(19) 0.023(5) Uiso 1 1 d . . . . .
C7 C 0.19292(10) 0.3691(3) -0.05237(13) 0.0214(3) Uani 1 1 d . . . . .
H7 H 0.1961(14) 0.294(5) -0.130(2) 0.029(6) Uiso 1 1 d . . . . .
O O 0.43388(6) 1.1460(2) -0.20262(9) 0.01544(19) Uani 1 1 d . . . . .
O1 O 0.39790(7) 0.9034(2) -0.05816(9) 0.0203(2) Uani 1 1 d . . . . .
C5 C 0.42010(8) 1.1213(3) -0.10028(12) 0.0151(2) Uani 1 1 d . . . . .
H5 H 0.4269(14) 1.307(5) -0.052(2) 0.033(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C 1.7407(14) . ?
N C2 1.4825(17) . ?
C C3 1.3930(19) . ?
C C4 1.386(2) . ?
C1 C2 1.5073(19) . ?
C1 C3 1.3944(18) . ?
C1 C6 1.3954(19) . ?
C4 C7 1.390(2) . ?
C6 C7 1.393(2) . ?
O C5 1.2643(16) . ?
O1 C5 1.2443(17) . ?

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
C3 C Cl1 118.74(11) . . ?
C4 C Cl1 119.20(11) . . ?
C4 C C3 122.06(13) . . ?
C3 C1 C2 118.68(12) . . ?
C3 C1 C6 119.09(12) . . ?
C6 C1 C2 122.19(12) . . ?
N C2 C1 114.07(11) . . ?
C C3 C1 119.50(12) . . ?
C C4 C7 117.94(13) . . ?
C7 C6 C1 120.34(13) . . ?
C4 C7 C6 121.07(14) . . ?
O1 C5 O 125.77(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_ab53716a
_database_code_depnum_ccdc_archive 'CCDC 1577321'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '1-Naphthylethylammonium Formate'
_chemical_formula_moiety         'C H O2, C12 H14 N'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_chemical_absolute_configuration ?
_chemical_melting_point          429.15-433.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   6.9086(3)
_cell_length_b                   17.9665(7)
_cell_length_c                   9.1840(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1139.95(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    111(2)
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0546 before and 0.0419 after correction. The Ratio of minimum to maximum transmission is 0.9426. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.471
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.148
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25693
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.065
_diffrn_reflns_theta_min         2.267
_diffrn_ambient_temperature      110.96
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3494
_reflns_number_total             3610
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.040
_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)+(0.0550P)²+0.1110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_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
O O 0.66665(13) 0.46857(5) 0.23569(11) 0.01953(19) Uani 1 1 d . . . . .
O1 O 0.69585(14) 0.58349(5) 0.32776(12) 0.0234(2) Uani 1 1 d . . . . .
C2 C 0.69652(16) 0.53778(7) 0.22576(15) 0.0172(2) Uani 1 1 d . . . . .
H2 H 0.720(3) 0.5541(10) 0.125(2) 0.022(4) Uiso 1 1 d . . . . .
N5 N 0.65543(16) 0.40240(5) 0.96684(12) 0.01613(19) Uani 1 1 d . . . . .
H5A H 0.533(3) 0.4088(12) 0.937(3) 0.032(5) Uiso 1 1 d . . . . .
H5B H 0.663(3) 0.4204(12) 1.056(2) 0.024(5) Uiso 1 1 d . . . . .
H5C H 0.731(4) 0.4302(12) 0.906(3) 0.032(5) Uiso 1 1 d . . . . .
C3 C 0.56944(15) 0.19472(7) 0.97995(13) 0.0149(2) Uani 1 1 d . . . . .
C4 C 0.32098(18) 0.17119(7) 1.16722(16) 0.0202(2) Uani 1 1 d . . . . .
H4 H 0.231(3) 0.1386(12) 1.210(3) 0.031(5) Uiso 1 1 d . . . . .
C6 C 0.57855(15) 0.27058(6) 1.02818(12) 0.0137(2) Uani 1 1 d . . . . .
C7 C 0.43874(17) 0.14485(7) 1.05105(14) 0.0175(2) Uani 1 1 d . . . . .
C8 C 0.72076(16) 0.32336(6) 0.95665(13) 0.0142(2) Uani 1 1 d . . . . .
H8 H 0.721(2) 0.3124(9) 0.853(2) 0.011(4) Uiso 1 1 d . . . . .
C9 C 0.68275(17) 0.16657(7) 0.86242(15) 0.0181(2) Uani 1 1 d . . . . .
H9 H 0.776(3) 0.1995(11) 0.816(2) 0.022(4) Uiso 1 1 d . . . . .
C10 C 0.46083(17) 0.29362(7) 1.14061(13) 0.0162(2) Uani 1 1 d . . . . .
H10 H 0.465(3) 0.3459(11) 1.174(2) 0.021(4) Uiso 1 1 d . . . . .
C11 C 0.42849(18) 0.06957(7) 1.00376(16) 0.0216(3) Uani 1 1 d . . . . .
H11 H 0.339(3) 0.0354(12) 1.058(3) 0.031(6) Uiso 1 1 d . . . . .
C12 C 0.66714(19) 0.09334(7) 0.81860(17) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.744(4) 0.0752(11) 0.737(3) 0.030(5) Uiso 1 1 d . . . . .
C13 C 0.33162(17) 0.24403(7) 1.21073(14) 0.0192(2) Uani 1 1 d . . . . .
H13 H 0.255(3) 0.2612(11) 1.285(2) 0.024(4) Uiso 1 1 d . . . . .
C14 C 0.92488(17) 0.31693(7) 1.02046(15) 0.0185(2) Uani 1 1 d . . . . .
H14A H 1.011(3) 0.3498(12) 0.969(3) 0.031(5) Uiso 1 1 d . . . . .
H14B H 0.923(3) 0.3342(12) 1.122(3) 0.033(6) Uiso 1 1 d . . . . .
H14C H 0.969(3) 0.2640(12) 1.016(3) 0.033(5) Uiso 1 1 d . . . . .
C15 C 0.5396(2) 0.04426(7) 0.89072(17) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.531(3) -0.0074(11) 0.857(2) 0.028(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O C2 1.2638(15) . ?
O1 C2 1.2459(17) . ?
N5 C8 1.4931(15) . ?
C3 C6 1.4345(15) . ?
C3 C7 1.4299(15) . ?
C3 C9 1.4261(17) . ?
C4 C7 1.4227(19) . ?
C4 C13 1.3703(19) . ?
C6 C8 1.5153(15) . ?
C6 C10 1.3780(16) . ?
C7 C11 1.4222(17) . ?
C8 C14 1.5315(16) . ?
C9 C12 1.3801(17) . ?
C10 C13 1.4160(16) . ?
C11 C15 1.369(2) . ?
C12 C15 1.412(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
O1 C2 O 126.43(13) . . ?
C7 C3 C6 118.82(10) . . ?
C9 C3 C6 123.14(10) . . ?
C9 C3 C7 118.04(11) . . ?
C13 C4 C7 120.38(11) . . ?
C3 C6 C8 119.28(10) . . ?
C10 C6 C3 119.40(10) . . ?
C10 C6 C8 121.30(10) . . ?
C4 C7 C3 119.68(11) . . ?
C11 C7 C3 119.20(12) . . ?
C11 C7 C4 121.12(11) . . ?
N5 C8 C6 111.84(9) . . ?
N5 C8 C14 109.03(9) . . ?
C6 C8 C14 112.58(10) . . ?
C12 C9 C3 121.06(12) . . ?
C6 C10 C13 121.59(11) . . ?
C15 C11 C7 121.31(12) . . ?
C9 C12 C15 120.49(13) . . ?
C4 C13 C10 120.14(12) . . ?
C11 C15 C12 119.89(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_ab54016
_database_code_depnum_ccdc_archive 'CCDC 1577325'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        'Benzylammonium Formate'
_chemical_formula_moiety         'C7 H10 N, C H O2'
_chemical_formula_sum            'C8 H11 N O2'
_chemical_formula_weight         153.18
_chemical_melting_point          352.15-367.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5468(5)
_cell_length_b                   11.0536(7)
_cell_length_c                   17.5296(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1656.07(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.92
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0562 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.9480. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.152
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39249
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.966
_diffrn_reflns_theta_min         2.324
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2557
_reflns_number_total             2869
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.045
_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)+(0.0590P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_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
H2A H -0.0843(14) 1.3742(11) -0.2156(6) 0.026(3) Uiso 1 1 d . . . . .
H2B H -0.2353(15) 1.3866(11) -0.1762(7) 0.029(3) Uiso 1 1 d . . . . .
H2C H -0.1445(14) 1.2673(11) -0.1664(7) 0.029(3) Uiso 1 1 d . . . . .
H4A H 0.0538(16) 1.3804(12) -0.1067(7) 0.032(3) Uiso 1 1 d . . . . .
H4B H -0.0505(14) 1.4954(10) -0.1139(7) 0.025(3) Uiso 1 1 d . . . . .
H5 H -0.4046(15) 1.4885(11) 0.0862(7) 0.028(3) Uiso 1 1 d . . . . .
H6 H -0.0856(14) 1.2150(11) 0.1249(7) 0.031(3) Uiso 1 1 d . . . . .
H8 H 0.0179(15) 1.2474(11) 0.0022(7) 0.030(3) Uiso 1 1 d . . . . .
H9 H -0.2914(14) 1.5175(11) -0.0347(7) 0.029(3) Uiso 1 1 d . . . . .
H10 H -0.2998(14) 1.3350(11) 0.1658(7) 0.028(3) Uiso 1 1 d . . . . .
C3 C -0.12831(8) 1.38478(6) -0.02820(4) 0.01640(13) Uani 1 1 d . . . . .
C4 C -0.05374(8) 1.40944(7) -0.10443(4) 0.01864(14) Uani 1 1 d . . . . .
C5 C -0.31709(8) 1.43686(7) 0.06913(4) 0.02048(14) Uani 1 1 d . . . . .
C6 C -0.13174(10) 1.27637(7) 0.09186(4) 0.02324(15) Uani 1 1 d . . . . .
C8 C -0.06833(9) 1.29507(7) 0.01952(4) 0.02156(15) Uani 1 1 d . . . . .
C9 C -0.25323(8) 1.45564(6) -0.00301(4) 0.01790(14) Uani 1 1 d . . . . .
C10 C -0.25614(9) 1.34734(7) 0.11658(4) 0.02135(15) Uani 1 1 d . . . . .
N2 N -0.13964(7) 1.35379(5) -0.16988(3) 0.01626(12) Uani 1 1 d . . . . .
H7 H 0.0059(14) 0.9058(10) 0.2508(7) 0.028(3) Uiso 1 1 d . . . . .
C7 C 0.07661(8) 0.95313(6) 0.21621(4) 0.01784(14) Uani 1 1 d . . . . .
O O 0.17271(7) 0.89525(5) 0.17706(3) 0.02246(13) Uani 1 1 d . . . . .
O1 O 0.06067(6) 1.06678(5) 0.21644(3) 0.02019(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C3 C4 1.5053(10) . ?
C3 C8 1.3950(10) . ?
C3 C9 1.3958(10) . ?
C4 N2 1.4946(9) . ?
C5 C9 1.3928(10) . ?
C5 C10 1.3936(11) . ?
C6 C8 1.3945(11) . ?
C6 C10 1.3905(11) . ?
C7 O 1.2469(9) . ?
C7 O1 1.2635(9) . ?

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
C8 C3 C4 120.36(6) . . ?
C8 C3 C9 119.36(6) . . ?
C9 C3 C4 120.21(6) . . ?
N2 C4 C3 113.51(6) . . ?
C9 C5 C10 120.08(7) . . ?
C10 C6 C8 119.79(7) . . ?
C6 C8 C3 120.52(7) . . ?
C5 C9 C3 120.22(6) . . ?
C6 C10 C5 120.03(7) . . ?
O C7 O1 125.65(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_ab50617a
_database_code_depnum_ccdc_archive 'CCDC 1577322'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '3-Methylbenzylammonium Formate'
_chemical_formula_moiety         'C H O2, C8 H12 N'
_chemical_formula_sum            'C9 H13 N O2'
_chemical_formula_weight         167.20
_chemical_melting_point          359.15-366.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.9827(8)
_cell_length_b                   4.8029(2)
_cell_length_c                   11.5315(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.947(3)
_cell_angle_gamma                90
_cell_volume                     912.85(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6037
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.74
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0945 before and 0.0434 after correction. The Ratio of minimum to maximum transmission is 0.8893. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.758
_exptl_crystal_size_mid          0.612
_exptl_crystal_size_min          0.043
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.989
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16747
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.802
_diffrn_reflns_theta_min         2.471
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2449
_reflns_number_total             2820
_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       'SAINT V8.38A'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      0.945
_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)+(0.0700P)²+0.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_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
O0AA O 0.43438(4) 0.34934(12) 0.29726(5) 0.01544(14) Uani 1 1 d . . . . .
O1AA O 0.39960(4) 0.59281(15) 0.44270(5) 0.02010(15) Uani 1 1 d . . . . .
N N 0.38691(4) 0.64552(15) 0.67895(6) 0.01279(14) Uani 1 1 d . . . . .
HA H 0.4155(8) 0.509(3) 0.7225(11) 0.023(3) Uiso 1 1 d . . . . .
HB H 0.3948(8) 0.631(3) 0.6003(13) 0.026(3) Uiso 1 1 d . . . . .
HC H 0.4083(8) 0.807(3) 0.7125(11) 0.021(3) Uiso 1 1 d . . . . .
C C 0.42142(5) 0.37487(17) 0.40037(7) 0.01437(16) Uani 1 1 d . . . . .
H H 0.4290(8) 0.210(3) 0.4500(11) 0.024(3) Uiso 1 1 d . . . . .
C0AA C 0.30111(5) 0.61689(17) 0.68593(7) 0.01381(15) Uani 1 1 d . . . . .
H0AA H 0.3004(8) 0.626(3) 0.7696(12) 0.024(3) Uiso 1 1 d . . . . .
H0AB H 0.2848(7) 0.428(3) 0.6565(10) 0.017(3) Uiso 1 1 d . . . . .
C1AA C 0.24552(5) 0.83749(16) 0.61713(7) 0.01304(15) Uani 1 1 d . . . . .
C2AA C 0.17923(5) 0.92556(18) 0.66010(7) 0.01497(16) Uani 1 1 d . . . . .
H2AA H 0.1698(8) 0.849(3) 0.7349(12) 0.022(3) Uiso 1 1 d . . . . .
C3AA C 0.12400(5) 1.12215(18) 0.59850(7) 0.01773(17) Uani 1 1 d . . . . .
C4AA C 0.20187(6) 1.1467(2) 0.44835(8) 0.02154(19) Uani 1 1 d . . . . .
H4AA H 0.2102(8) 1.227(3) 0.3749(13) 0.031(3) Uiso 1 1 d . . . . .
C5AA C 0.25649(5) 0.94887(19) 0.51027(7) 0.01758(17) Uani 1 1 d . . . . .
H5AA H 0.3040(9) 0.894(3) 0.4759(13) 0.030(3) Uiso 1 1 d . . . . .
C6AA C 0.05352(6) 1.2182(2) 0.64658(9) 0.0261(2) Uani 1 1 d . . . . .
H6AA H 0.0526(14) 1.125(5) 0.718(2) 0.086(7) Uiso 1 1 d . . . . .
H6AB H 0.0021(11) 1.194(4) 0.5854(15) 0.052(5) Uiso 1 1 d . . . . .
H6AC H 0.0584(13) 1.424(5) 0.6612(19) 0.075(6) Uiso 1 1 d . . . . .
C7AA C 0.13646(5) 1.2326(2) 0.49218(8) 0.02066(18) Uani 1 1 d . . . . .
H7AA H 0.0985(9) 1.374(3) 0.4482(13) 0.037(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O0AA C 1.2662(10) . ?
O1AA C 1.2484(10) . ?
N C0AA 1.4849(10) . ?
C0AA C1AA 1.5107(11) . ?
C1AA C2AA 1.4003(10) . ?
C1AA C5AA 1.3964(11) . ?
C2AA C3AA 1.3981(12) . ?
C3AA C6AA 1.5076(12) . ?
C3AA C7AA 1.3981(12) . ?
C4AA C5AA 1.3976(12) . ?
C4AA C7AA 1.3895(12) . ?

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
O1AA C O0AA 125.70(8) . . ?
N C0AA C1AA 113.81(6) . . ?
C2AA C1AA C0AA 118.68(7) . . ?
C5AA C1AA C0AA 122.19(7) . . ?
C5AA C1AA C2AA 119.09(7) . . ?
C3AA C2AA C1AA 121.49(7) . . ?
C2AA C3AA C6AA 120.98(8) . . ?
C7AA C3AA C2AA 118.49(7) . . ?
C7AA C3AA C6AA 120.52(8) . . ?
C7AA C4AA C5AA 120.43(8) . . ?
C1AA C5AA C4AA 119.87(7) . . ?
C4AA C7AA C3AA 120.63(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_ab18715a
_database_code_depnum_ccdc_archive 'CCDC 1577320'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '4-Methylbenzylammonium Formate'
_chemical_formula_moiety         'C H O2, C8 H12 N'
_chemical_formula_sum            'C9 H13 N O2'
_chemical_formula_weight         167.20
_chemical_melting_point          413.15-416.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.090(8)
_cell_length_b                   4.909(2)
_cell_length_c                   11.565(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.75(3)
_cell_angle_gamma                90
_cell_volume                     913.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2920
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_correction_T_min  0.8080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0780 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.9374. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.068
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14294
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.486
_diffrn_reflns_theta_min         2.533
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1309
_reflns_number_total             1880
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.024
_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)+(0.0700P)²+0.1950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1418
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C9(H9), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_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 0.42991(8) 0.6398(2) 0.78353(12) 0.0425(4) Uani 1 1 d . . . . .
O5 O 0.39305(9) 0.4076(3) 0.92156(12) 0.0584(5) Uani 1 1 d . . . . .
C4 C 0.41589(11) 0.6164(4) 0.88200(18) 0.0424(5) Uani 1 1 d . . . . .
H4 H 0.4233 0.7715 0.9307 0.051 Uiso 1 1 calc R . . . .
N2 N 0.38425(8) 0.3628(3) 1.15861(13) 0.0360(4) Uani 1 1 d . . . . .
H2A H 0.3878 0.3687 1.0836 0.043 Uiso 1 1 calc GR . . . .
H2B H 0.4016 0.2010 1.1923 0.043 Uiso 1 1 calc GR . . . .
H2C H 0.4159 0.4931 1.2048 0.043 Uiso 1 1 calc GR . . . .
C3 C 0.23767(10) 0.1887(3) 1.07905(15) 0.0329(4) Uani 1 1 d . . . . .
C6 C 0.11775(11) -0.0952(4) 1.05452(17) 0.0429(5) Uani 1 1 d . . . . .
H6 H 0.0769 -0.1548 1.0850 0.052 Uiso 1 1 calc R . . . .
C7 C 0.11911(11) -0.1965(4) 0.94348(16) 0.0384(4) Uani 1 1 d . . . . .
C8 C 0.29706(10) 0.4050(4) 1.15059(16) 0.0368(4) Uani 1 1 d . . . . .
H8A H 0.2786 0.5803 1.1124 0.044 Uiso 1 1 calc R . . . .
H8B H 0.2947 0.4117 1.2332 0.044 Uiso 1 1 calc R . . . .
C9 C 0.18103(12) -0.1025(4) 0.90213(17) 0.0458(5) Uani 1 1 d . . . . .
H9 H 0.1839 -0.1680 0.8282 0.055 Uiso 1 1 calc R . . . .
C11 C 0.17602(11) 0.0931(4) 1.12122(17) 0.0415(5) Uani 1 1 d . . . . .
H11 H 0.1736 0.1564 1.1957 0.050 Uiso 1 1 calc R . . . .
C12 C 0.23932(12) 0.0877(4) 0.96820(16) 0.0438(5) Uani 1 1 d . . . . .
H12 H 0.2800 0.1480 0.9374 0.053 Uiso 1 1 calc R . . . .
C1 C 0.05668(12) -0.4049(4) 0.87182(18) 0.0487(5) Uani 1 1 d . . . . .
H1A H 0.0751 -0.5838 0.9028 0.073 Uiso 1 1 calc GR . . . .
H1B H 0.0514 -0.3951 0.7866 0.073 Uiso 1 1 calc GR . . . .
H1C H 0.0037 -0.3686 0.8805 0.073 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
O1 C4 1.246(2) . ?
O5 C4 1.238(2) . ?
N2 C8 1.476(2) . ?
C3 C8 1.508(2) . ?
C3 C11 1.384(2) . ?
C3 C12 1.384(2) . ?
C6 C7 1.385(3) . ?
C6 C11 1.386(3) . ?
C7 C9 1.379(3) . ?
C7 C1 1.508(3) . ?
C9 C12 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 C4 O1 126.59(18) . . ?
C11 C3 C8 119.78(16) . . ?
C12 C3 C8 122.67(15) . . ?
C12 C3 C11 117.48(17) . . ?
C7 C6 C11 121.42(16) . . ?
C6 C7 C1 121.51(17) . . ?
C9 C7 C6 117.19(17) . . ?
C9 C7 C1 121.30(18) . . ?
N2 C8 C3 114.43(14) . . ?
C7 C9 C12 121.67(17) . . ?
C3 C11 C6 121.28(17) . . ?
C3 C12 C9 120.97(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_ab50516a
_database_code_depnum_ccdc_archive 'CCDC 1577324'
_audit_update_record             
;
2017-09-30 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_audit_creation_date             2017-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        '4-Chlorobenzylammonum Formate'
_chemical_formula_moiety         'C7 H9 Cl N, C H O2'
_chemical_formula_sum            'C8 H10 Cl N O2'
_chemical_formula_weight         187.62
_chemical_melting_point          415.15-419.15
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   16.7551(13)
_cell_length_b                   4.8441(4)
_cell_length_c                   11.4478(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.041(3)
_cell_angle_gamma                90
_cell_volume                     878.30(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.09
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0454 before and 0.0320 after correction. The Ratio of minimum to maximum transmission is 0.9274. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.243
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22168
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.160
_diffrn_reflns_theta_min         2.572
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3328
_reflns_number_total             3487
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.103
_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)+(0.0350P)²+0.1670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0657
_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:
 C9(H9)
;
_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
Cl1 Cl 0.04997(2) 0.54795(3) 0.85450(2) 0.01829(5) Uani 1 1 d . . . . .
N2 N 0.38308(3) 1.35903(10) 1.16396(4) 0.01155(9) Uani 1 1 d . . . . .
H2A H 0.4035(6) 1.201(2) 1.2021(9) 0.018(2) Uiso 1 1 d . . . . .
H2B H 0.4123(7) 1.497(2) 1.2113(10) 0.021(2) Uiso 1 1 d . . . . .
H2C H 0.3887(7) 1.373(2) 1.0873(11) 0.026(3) Uiso 1 1 d . . . . .
C3 C 0.12053(4) 0.79018(12) 0.94297(5) 0.01363(10) Uani 1 1 d . . . . .
C4 C 0.29389(4) 1.39479(12) 1.15804(5) 0.01232(9) Uani 1 1 d . . . . .
H4A H 0.2766(7) 1.570(2) 1.1271(10) 0.021(2) Uiso 1 1 d . . . . .
H4B H 0.2925(7) 1.394(2) 1.2414(10) 0.020(2) Uiso 1 1 d . . . . .
C5 C 0.24378(4) 1.07018(13) 0.97454(6) 0.01584(11) Uani 1 1 d . . . . .
H5 H 0.2910(8) 1.129(3) 0.9487(11) 0.031(3) Uiso 1 1 d . . . . .
C7 C 0.23522(3) 1.17649(12) 1.08299(5) 0.01116(9) Uani 1 1 d . . . . .
C8 C 0.16804(4) 1.08579(13) 1.12002(5) 0.01412(10) Uani 1 1 d . . . . .
H8 H 0.1606(7) 1.158(2) 1.1943(10) 0.023(3) Uiso 1 1 d . . . . .
C10 C 0.18678(4) 0.87628(14) 0.90420(6) 0.01691(11) Uani 1 1 d . . . . .
H10 H 0.1940(8) 0.796(3) 0.8293(11) 0.030(3) Uiso 1 1 d . . . . .
C11 C 0.11032(4) 0.89268(13) 1.05034(6) 0.01526(10) Uani 1 1 d . . . . .
H11 H 0.0638(7) 0.833(3) 1.0756(11) 0.027(3) Uiso 1 1 d . . . . .
O1 O 0.43165(3) 0.85366(9) 1.28704(4) 0.01419(8) Uani 1 1 d . . . . .
O6 O 0.39578(3) 1.09580(11) 1.42830(4) 0.01899(10) Uani 1 1 d . . . . .
C9 C 0.41772(4) 0.87919(13) 1.38834(5) 0.01385(10) Uani 1 1 d . . . . .
H9 H 0.4246 0.7192 1.4387 0.017 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 C3 1.7376(6) . ?
N2 C4 1.4837(8) . ?
C3 C10 1.3872(8) . ?
C3 C11 1.3870(9) . ?
C4 C7 1.5072(8) . ?
C5 C7 1.3940(8) . ?
C5 C10 1.3932(8) . ?
C7 C8 1.3968(8) . ?
C8 C11 1.3940(9) . ?
O1 C9 1.2614(7) . ?
O6 C9 1.2470(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C3 Cl1 118.68(5) . . ?
C11 C3 Cl1 120.07(4) . . ?
C11 C3 C10 121.26(5) . . ?
N2 C4 C7 113.83(5) . . ?
C10 C5 C7 120.90(5) . . ?
C5 C7 C4 121.96(5) . . ?
C5 C7 C8 118.77(5) . . ?
C8 C7 C4 119.22(5) . . ?
C11 C8 C7 120.98(5) . . ?
C3 C10 C5 119.14(6) . . ?
C3 C11 C8 118.96(5) . . ?
O6 C9 O1 125.79(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
