# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_0var306
_database_code_depnum_ccdc_archive 'CCDC 1473655'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;
_audit_creation_date             2016-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        3-(2-methoxypyridin-3-yl)-1,1-dimethylurea
_chemical_formula_moiety         'C9 H13 N3 O2'
_chemical_formula_sum            'C9 H13 N3 O2'
_chemical_formula_weight         195.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H13 O2 N3'
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                   7.3261(5)
_cell_length_b                   20.1659(12)
_cell_length_c                   13.1676(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.555(7)
_cell_angle_gamma                90
_cell_volume                     1898.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6716
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.9359
_cell_measurement_theta_min      2.8428
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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       prism
_exptl_crystal_F_000             832
_exptl_crystal_preparation       'See experimental part.'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29572
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.002
_diffrn_reflns_theta_min         2.849
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00  -44.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339 -178.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -90.00    3.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -38.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1277    0.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -99.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1277  -99.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   96.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1277 -178.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1277   57.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   -6.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1277   38.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  9 omega  -75.00  -48.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4031  -57.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega  -20.00    7.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4968  -99.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   10.00   63.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4968  -99.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   64.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4968   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega    0.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       21.4968   57.0000  -60.0000 83
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0015949000
_diffrn_orient_matrix_UB_12      -0.0183443000
_diffrn_orient_matrix_UB_13      0.0457489000
_diffrn_orient_matrix_UB_21      0.0670250000
_diffrn_orient_matrix_UB_22      0.0219210000
_diffrn_orient_matrix_UB_23      0.0293291000
_diffrn_orient_matrix_UB_31      -0.0732140000
_diffrn_orient_matrix_UB_32      0.0204759000
_diffrn_orient_matrix_UB_33      0.0095243000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3779
_reflns_number_total             4907
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0542
_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)+(0.0465P)²+1.2110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2A(H2A), N2B(H2B), C3B(H3B), C3A(H3A), C4A(H4A), C5A(H5A), C4B(H4B), C5B(H5B)
2.b Idealised Me refined as rotating group:
 C6B(H6BA,H6BB,H6BC), C8B(H8BA,H8BB,H8BC), C6A(H6AA,H6AB,H6AC), C8A(H8AA,H8AB,
 H8AC), C9B(H9BA,H9BB,H9BC), C9A(H9AA,H9AB,H9AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1A O 0.62637(17) 0.97303(5) 0.35670(9) 0.0226(3) Uani 1 1 d . . . . .
O1B O 0.86909(17) 0.47455(5) 0.64394(9) 0.0232(3) Uani 1 1 d . . . . .
O2A O 0.43307(18) 0.74386(6) 0.37777(9) 0.0291(3) Uani 1 1 d . . . . .
O2B O 0.78811(19) 0.71145(6) 0.67684(9) 0.0304(3) Uani 1 1 d . . . . .
N2A N 0.5053(2) 0.85021(7) 0.33958(10) 0.0210(3) Uani 1 1 d . . . . .
H2A H 0.5000 0.8787 0.2884 0.025 Uiso 1 1 calc R . . . .
N1A N 0.7404(2) 0.96787(7) 0.53478(11) 0.0227(3) Uani 1 1 d . . . . .
N2B N 0.8567(2) 0.60069(7) 0.68713(10) 0.0238(3) Uani 1 1 d . . . . .
H2B H 0.9025 0.5687 0.7307 0.029 Uiso 1 1 calc R . . . .
N1B N 0.7348(2) 0.48667(7) 0.46887(11) 0.0238(3) Uani 1 1 d . . . . .
N3A N 0.3338(2) 0.78230(7) 0.21253(11) 0.0266(3) Uani 1 1 d . . . . .
N3B N 0.9595(2) 0.66962(7) 0.82837(11) 0.0253(3) Uani 1 1 d . . . . .
C1B C 0.7927(2) 0.51355(8) 0.56109(12) 0.0205(3) Uani 1 1 d . . . . .
C2A C 0.5945(2) 0.87166(8) 0.43906(12) 0.0188(3) Uani 1 1 d . . . . .
C7A C 0.4244(2) 0.78847(8) 0.31341(13) 0.0213(3) Uani 1 1 d . . . . .
C3B C 0.7051(2) 0.62295(8) 0.50136(13) 0.0224(3) Uani 1 1 d . . . . .
H3B H 0.6939 0.6693 0.5118 0.027 Uiso 1 1 calc R . . . .
C7B C 0.8640(2) 0.66423(8) 0.72780(13) 0.0214(3) Uani 1 1 d . . . . .
C3A C 0.6314(2) 0.83472(8) 0.52984(13) 0.0222(3) Uani 1 1 d . . . . .
H3A H 0.5956 0.7894 0.5290 0.027 Uiso 1 1 calc R . . . .
C1A C 0.6562(2) 0.93878(8) 0.44796(12) 0.0193(3) Uani 1 1 d . . . . .
C2B C 0.7840(2) 0.58210(8) 0.58355(12) 0.0201(3) Uani 1 1 d . . . . .
C4A C 0.7222(2) 0.86496(8) 0.62291(13) 0.0243(4) Uani 1 1 d . . . . .
H4A H 0.7489 0.8402 0.6858 0.029 Uiso 1 1 calc R . . . .
C5A C 0.7725(2) 0.93052(9) 0.62272(13) 0.0246(4) Uani 1 1 d . . . . .
H5A H 0.8321 0.9506 0.6866 0.029 Uiso 1 1 calc R . . . .
C6B C 0.8775(3) 0.40446(8) 0.62332(13) 0.0246(4) Uani 1 1 d . . . . .
H6BA H 0.9505 0.3972 0.5702 0.037 Uiso 1 1 calc GR . . . .
H6BB H 0.7505 0.3873 0.5984 0.037 Uiso 1 1 calc GR . . . .
H6BC H 0.9371 0.3813 0.6874 0.037 Uiso 1 1 calc GR . . . .
C4B C 0.6422(2) 0.59516(8) 0.40279(13) 0.0240(4) Uani 1 1 d . . . . .
H4B H 0.5884 0.6225 0.3453 0.029 Uiso 1 1 calc R . . . .
C8B C 0.9576(3) 0.73306(9) 0.88135(13) 0.0280(4) Uani 1 1 d . . . . .
H8BA H 1.0809 0.7539 0.8908 0.042 Uiso 1 1 calc GR . . . .
H8BB H 0.9273 0.7258 0.9494 0.042 Uiso 1 1 calc GR . . . .
H8BC H 0.8632 0.7621 0.8394 0.042 Uiso 1 1 calc GR . . . .
C6A C 0.6966(3) 1.04007(8) 0.36325(13) 0.0240(4) Uani 1 1 d . . . . .
H6AA H 0.6738 1.0595 0.2934 0.036 Uiso 1 1 calc GR . . . .
H6AB H 0.8313 1.0398 0.3933 0.036 Uiso 1 1 calc GR . . . .
H6AC H 0.6326 1.0664 0.4074 0.036 Uiso 1 1 calc GR . . . .
C5B C 0.6586(2) 0.52786(9) 0.38969(13) 0.0254(4) Uani 1 1 d . . . . .
H5B H 0.6148 0.5095 0.3223 0.030 Uiso 1 1 calc R . . . .
C8A C 0.2485(3) 0.71917(8) 0.17620(14) 0.0283(4) Uani 1 1 d . . . . .
H8AA H 0.2850 0.6857 0.2308 0.042 Uiso 1 1 calc GR . . . .
H8AB H 0.2909 0.7054 0.1138 0.042 Uiso 1 1 calc GR . . . .
H8AC H 0.1121 0.7239 0.1595 0.042 Uiso 1 1 calc GR . . . .
C9B C 1.0700(3) 0.61672(9) 0.88674(14) 0.0275(4) Uani 1 1 d . . . . .
H9BA H 0.9870 0.5853 0.9112 0.041 Uiso 1 1 calc GR . . . .
H9BB H 1.1580 0.6356 0.9466 0.041 Uiso 1 1 calc GR . . . .
H9BC H 1.1397 0.5936 0.8418 0.041 Uiso 1 1 calc GR . . . .
C9A C 0.3132(3) 0.83562(9) 0.13625(14) 0.0343(4) Uani 1 1 d . . . . .
H9AA H 0.2517 0.8736 0.1611 0.051 Uiso 1 1 calc GR . . . .
H9AB H 0.2372 0.8201 0.0699 0.051 Uiso 1 1 calc GR . . . .
H9AC H 0.4368 0.8490 0.1265 0.051 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
O1A C1A 1.3618(18) . ?
O1A C6A 1.4426(19) . ?
O1B C1B 1.3626(19) . ?
O1B C6B 1.4429(19) . ?
O2A C7A 1.2280(19) . ?
O2B C7B 1.226(2) . ?
N2A H2A 0.8800 . ?
N2A C2A 1.399(2) . ?
N2A C7A 1.390(2) . ?
N1A C1A 1.313(2) . ?
N1A C5A 1.358(2) . ?
N2B H2B 0.8800 . ?
N2B C7B 1.385(2) . ?
N2B C2B 1.403(2) . ?
N1B C1B 1.313(2) . ?
N1B C5B 1.355(2) . ?
N3A C7A 1.355(2) . ?
N3A C8A 1.452(2) . ?
N3A C9A 1.457(2) . ?
N3B C7B 1.361(2) . ?
N3B C8B 1.459(2) . ?
N3B C9B 1.454(2) . ?
C1B C2B 1.418(2) . ?
C2A C3A 1.384(2) . ?
C2A C1A 1.424(2) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.383(2) . ?
C3B C4B 1.397(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.401(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.373(2) . ?
C5A H5A 0.9500 . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
C4B H4B 0.9500 . ?
C4B C5B 1.377(2) . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C5B H5B 0.9500 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A C6A 115.84(12) . . ?
C1B O1B C6B 116.21(13) . . ?
C2A N2A H2A 116.7 . . ?
C7A N2A H2A 116.7 . . ?
C7A N2A C2A 126.60(14) . . ?
C1A N1A C5A 117.12(14) . . ?
C7B N2B H2B 116.7 . . ?
C7B N2B C2B 126.69(14) . . ?
C2B N2B H2B 116.7 . . ?
C1B N1B C5B 117.05(15) . . ?
C7A N3A C8A 119.16(14) . . ?
C7A N3A C9A 124.28(14) . . ?
C8A N3A C9A 116.56(14) . . ?
C7B N3B C8B 118.63(14) . . ?
C7B N3B C9B 124.42(14) . . ?
C9B N3B C8B 116.92(14) . . ?
O1B C1B C2B 115.15(14) . . ?
N1B C1B O1B 119.73(14) . . ?
N1B C1B C2B 125.11(15) . . ?
N2A C2A C1A 116.49(14) . . ?
C3A C2A N2A 127.30(15) . . ?
C3A C2A C1A 116.20(14) . . ?
O2A C7A N2A 121.99(15) . . ?
O2A C7A N3A 123.36(15) . . ?
N3A C7A N2A 114.64(14) . . ?
C2B C3B H3B 120.5 . . ?
C2B C3B C4B 119.05(15) . . ?
C4B C3B H3B 120.5 . . ?
O2B C7B N2B 122.14(15) . . ?
O2B C7B N3B 123.12(15) . . ?
N3B C7B N2B 114.74(14) . . ?
C2A C3A H3A 120.4 . . ?
C2A C3A C4A 119.19(15) . . ?
C4A C3A H3A 120.4 . . ?
O1A C1A C2A 114.99(14) . . ?
N1A C1A O1A 119.76(14) . . ?
N1A C1A C2A 125.23(15) . . ?
N2B C2B C1B 116.00(14) . . ?
C3B C2B N2B 127.40(15) . . ?
C3B C2B C1B 116.60(15) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A C3A 119.63(15) . . ?
C5A C4A H4A 120.2 . . ?
N1A C5A C4A 122.60(15) . . ?
N1A C5A H5A 118.7 . . ?
C4A C5A H5A 118.7 . . ?
O1B C6B H6BA 109.5 . . ?
O1B C6B H6BB 109.5 . . ?
O1B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B C3B 119.46(15) . . ?
C5B C4B H4B 120.3 . . ?
N3B C8B H8BA 109.5 . . ?
N3B C8B H8BB 109.5 . . ?
N3B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
O1A C6A H6AA 109.5 . . ?
O1A C6A H6AB 109.5 . . ?
O1A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
N1B C5B C4B 122.73(16) . . ?
N1B C5B H5B 118.6 . . ?
C4B C5B H5B 118.6 . . ?
N3A C8A H8AA 109.5 . . ?
N3A C8A H8AB 109.5 . . ?
N3A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N3B C9B H9BA 109.5 . . ?
N3B C9B H9BB 109.5 . . ?
N3B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
N3A C9A H9AA 109.5 . . ?
N3A C9A H9AB 109.5 . . ?
N3A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method EtOAc/hexane
####################################################################### 
# 
# 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_var260
_database_code_depnum_ccdc_archive 'CCDC 1473656'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;
_audit_creation_date             2016-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        3-(6-bromopyridin-2-yl)-1,1-dimethylurea
_chemical_formula_moiety         'C8 H10 Br N3 O'
_chemical_formula_sum            'C8 H10 Br N3 O'
_chemical_formula_weight         244.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'br1 C8 H10 N2'
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'
Br Br -0.2901 2.4595 '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                   4.18964(13)
_cell_length_b                   21.1953(8)
_cell_length_c                   10.4364(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.814(3)
_cell_angle_gamma                90
_cell_volume                     921.99(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6702
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.1027
_cell_measurement_theta_min      2.7409
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_preparation       'See experimental part.'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23771
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.172
_diffrn_reflns_theta_min         2.746
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   46.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   77.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   77.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega   13.00   60.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   77.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  178.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714 -178.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   39.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   57.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega  -39.00   55.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -87.0000    7.0000 94

#__ type_ start__ end____ width___ exp.time_
  9 omega  -41.00  -14.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   20.00   47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   19.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  -25.00   24.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -99.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
 13 omega  -25.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -99.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
 14 omega  -25.00   61.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -99.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
 15 omega   -2.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 16 omega   -2.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   57.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega  -53.00   44.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -38.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 18 omega  -86.00  -51.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -57.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 19 omega  -38.00  -13.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -87.0000 -124.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega  -82.00  -52.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031 -178.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 21 omega  -18.00    9.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -87.0000    7.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega  -86.00  -47.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  178.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 23 omega   -6.00   26.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406   87.0000  172.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega    4.00   37.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406   87.0000  -55.0000 33
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1204397000
_diffrn_orient_matrix_UB_12      0.0120086000
_diffrn_orient_matrix_UB_13      0.0462586000
_diffrn_orient_matrix_UB_21      0.0119141000
_diffrn_orient_matrix_UB_22      0.0275082000
_diffrn_orient_matrix_UB_23      -0.0379377000
_diffrn_orient_matrix_UB_31      -0.1197589000
_diffrn_orient_matrix_UB_32      0.0148016000
_diffrn_orient_matrix_UB_33      0.0329046000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2148
_reflns_number_total             2504
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.132
_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)+(0.0200P)²+3.5700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1016
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2A), C3(H3)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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
Br1 Br 0.45658(9) 0.49348(2) 0.82338(4) 0.01970(12) Uani 1 1 d . . . . .
O1 O 0.2791(6) 0.24107(12) 0.4374(2) 0.0176(5) Uani 1 1 d . . . . .
N1 N 0.4240(7) 0.37491(14) 0.7140(3) 0.0137(6) Uani 1 1 d . . . . .
N3 N 0.1033(8) 0.17602(15) 0.5873(3) 0.0174(7) Uani 1 1 d . . . . .
N2 N 0.3485(7) 0.27176(14) 0.6496(3) 0.0141(6) Uani 1 1 d . . . . .
H2 H 0.2036 0.2758 0.7018 0.017 Uiso 1 1 d R . . . .
C5 C 0.5441(8) 0.43165(17) 0.6977(3) 0.0129(7) Uani 1 1 d . . . . .
C6 C 0.2407(8) 0.22985(17) 0.5507(3) 0.0135(7) Uani 1 1 d . . . . .
C4 C 0.7208(9) 0.44966(18) 0.5995(4) 0.0176(8) Uani 1 1 d . . . . .
H4 H 0.7979 0.4915 0.5925 0.021 Uiso 1 1 calc R . . . .
C1 C 0.4789(8) 0.33101(16) 0.6265(3) 0.0124(7) Uani 1 1 d . . . . .
C2 C 0.6621(8) 0.34283(18) 0.5242(4) 0.0159(7) Uani 1 1 d . . . . .
H2A H 0.7040 0.3104 0.4654 0.019 Uiso 1 1 calc R . . . .
C7 C -0.0393(9) 0.13292(18) 0.4877(4) 0.0172(8) Uani 1 1 d . . . . .
H7A H -0.2696 0.1415 0.4710 0.026 Uiso 1 1 calc GR . . . .
H7B H -0.0071 0.0892 0.5170 0.026 Uiso 1 1 calc GR . . . .
H7C H 0.0634 0.1392 0.4083 0.026 Uiso 1 1 calc GR . . . .
C3 C 0.7799(9) 0.40296(18) 0.5112(4) 0.0180(8) Uani 1 1 d . . . . .
H3 H 0.9018 0.4125 0.4418 0.022 Uiso 1 1 calc R . . . .
C8 C 0.0294(10) 0.1626(2) 0.7177(4) 0.0236(9) Uani 1 1 d . . . . .
H8A H 0.2206 0.1699 0.7781 0.035 Uiso 1 1 calc GR . . . .
H8B H -0.0378 0.1185 0.7234 0.035 Uiso 1 1 calc GR . . . .
H8C H -0.1442 0.1903 0.7395 0.035 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
Br1 C5 1.915(3) . ?
O1 C6 1.233(4) . ?
N1 C5 1.321(5) . ?
N1 C1 1.340(4) . ?
N3 C6 1.350(5) . ?
N3 C7 1.466(5) . ?
N3 C8 1.454(5) . ?
N2 H2 0.8601 . ?
N2 C6 1.401(5) . ?
N2 C1 1.400(4) . ?
C5 C4 1.378(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.392(5) . ?
C1 C2 1.399(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.378(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C3 H3 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 116.8(3) . . ?
C6 N3 C7 118.7(3) . . ?
C6 N3 C8 124.6(3) . . ?
C8 N3 C7 115.6(3) . . ?
C6 N2 H2 109.5 . . ?
C1 N2 H2 109.4 . . ?
C1 N2 C6 123.0(3) . . ?
N1 C5 Br1 115.6(3) . . ?
N1 C5 C4 126.0(3) . . ?
C4 C5 Br1 118.3(3) . . ?
O1 C6 N3 122.4(3) . . ?
O1 C6 N2 121.4(3) . . ?
N3 C6 N2 116.2(3) . . ?
C5 C4 H4 121.9 . . ?
C5 C4 C3 116.1(3) . . ?
C3 C4 H4 121.9 . . ?
N1 C1 N2 114.1(3) . . ?
N1 C1 C2 122.8(3) . . ?
C2 C1 N2 123.1(3) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2A 121.0 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method EtOAc/hexane
####################################################################### 
# 
# 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_var257
_database_code_depnum_ccdc_archive 'CCDC 1473657'
_audit_update_record             
;
2016-04-12 deposited with the CCDC.
2016-10-06 downloaded from the CCDC.
;
_audit_creation_date             2016-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        3-(6-chloropyridin-2-yl)-1,1-dimethylurea
_chemical_formula_moiety         'C8 H10 Cl N3 O'
_chemical_formula_sum            'C8 H10 Cl N3 O'
_chemical_formula_weight         199.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c8 n3 cl1 o1 H10'
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                   4.1274(3)
_cell_length_b                   20.8167(12)
_cell_length_c                   10.4887(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.909(5)
_cell_angle_gamma                90
_cell_volume                     896.38(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1214
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.0358
_cell_measurement_theta_min      2.7587
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_preparation       'See experimental part.'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4077
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.100
_diffrn_reflns_theta_min         2.764
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   23.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -99.0000   60.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   -5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   98.0000  -65.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714    0.0000 -150.0000 125

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00  -70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  178.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0039702000
_diffrn_orient_matrix_UB_12      0.0157269000
_diffrn_orient_matrix_UB_13      -0.0597842000
_diffrn_orient_matrix_UB_21      0.0622090000
_diffrn_orient_matrix_UB_22      0.0280433000
_diffrn_orient_matrix_UB_23      0.0321797000
_diffrn_orient_matrix_UB_31      0.1612530000
_diffrn_orient_matrix_UB_32      -0.0112249000
_diffrn_orient_matrix_UB_33      -0.0034216000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1696
_reflns_number_total             2078
_reflns_odcompleteness_completeness 95.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.075
_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)+(0.0370P)²+0.4340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1028
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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 0.55378(12) 0.49091(2) 0.16740(5) 0.02290(16) Uani 1 1 d . . . . .
O1 O 0.7371(3) 0.24159(7) 0.54696(12) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.5908(4) 0.37639(8) 0.26918(15) 0.0160(3) Uani 1 1 d . . . . .
N3 N 0.9078(4) 0.17421(8) 0.39783(15) 0.0180(4) Uani 1 1 d . . . . .
N2 N 0.6651(4) 0.27198(8) 0.33569(15) 0.0166(4) Uani 1 1 d . . . . .
H2 H 0.6809 0.2605 0.2578 0.020 Uiso 1 1 calc R . . . .
C6 C 0.7712(4) 0.22932(9) 0.43388(18) 0.0155(4) Uani 1 1 d . . . . .
C1 C 0.5346(4) 0.33235(9) 0.35761(17) 0.0147(4) Uani 1 1 d . . . . .
C2 C 0.3553(4) 0.34600(10) 0.46034(18) 0.0178(4) Uani 1 1 d . . . . .
H2A H 0.3135 0.3144 0.5191 0.021 Uiso 1 1 calc R . . . .
C5 C 0.4736(4) 0.43447(10) 0.28366(17) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.3008(4) 0.45423(10) 0.38290(19) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.2283 0.4963 0.3894 0.024 Uiso 1 1 calc R . . . .
C7 C 1.0476(5) 0.13027(10) 0.49730(18) 0.0197(4) Uani 1 1 d . . . . .
H7A H 1.2791 0.1364 0.5105 0.030 Uiso 1 1 calc GR . . . .
H7B H 1.0012 0.0868 0.4710 0.030 Uiso 1 1 calc GR . . . .
H7C H 0.9542 0.1387 0.5757 0.030 Uiso 1 1 calc GR . . . .
C3 C 0.2424(4) 0.40774(10) 0.47181(19) 0.0219(5) Uani 1 1 d . . . . .
H3 H 0.1256 0.4183 0.5401 0.026 Uiso 1 1 calc R . . . .
C8 C 0.9736(5) 0.15947(11) 0.26748(18) 0.0235(5) Uani 1 1 d . . . . .
H8A H 0.7973 0.1748 0.2085 0.035 Uiso 1 1 calc GR . . . .
H8B H 0.9948 0.1138 0.2581 0.035 Uiso 1 1 calc GR . . . .
H8C H 1.1723 0.1801 0.2498 0.035 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
Cl1 C5 1.7495(19) . ?
O1 C6 1.235(2) . ?
N1 C1 1.341(2) . ?
N1 C5 1.317(2) . ?
N3 C6 1.349(2) . ?
N3 C7 1.461(2) . ?
N3 C8 1.454(2) . ?
N2 H2 0.8600 . ?
N2 C6 1.396(2) . ?
N2 C1 1.396(2) . ?
C1 C2 1.398(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.377(3) . ?
C5 C4 1.383(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C3 H3 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C5 N1 C1 117.13(16) . . ?
C6 N3 C7 118.54(16) . . ?
C6 N3 C8 124.53(17) . . ?
C8 N3 C7 116.18(16) . . ?
C6 N2 H2 118.4 . . ?
C1 N2 H2 118.4 . . ?
C1 N2 C6 123.26(16) . . ?
O1 C6 N3 122.48(18) . . ?
O1 C6 N2 121.25(18) . . ?
N3 C6 N2 116.26(16) . . ?
N1 C1 N2 113.86(16) . . ?
N1 C1 C2 122.48(18) . . ?
N2 C1 C2 123.64(17) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 117.91(18) . . ?
C3 C2 H2A 121.0 . . ?
N1 C5 Cl1 115.98(14) . . ?
N1 C5 C4 125.73(18) . . ?
C4 C5 Cl1 118.28(15) . . ?
C5 C4 H4 122.0 . . ?
C3 C4 C5 116.01(19) . . ?
C3 C4 H4 122.0 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C3 C4 120.71(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method EtOAc/hexane
