# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_DM-USRKNB1-11-1B
_database_code_depnum_ccdc_archive 'CCDC 1440626'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_weight         245.28
_chemical_melting_point          385

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.438(7)
_cell_length_b                   11.805(7)
_cell_length_c                   8.680(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.022(11)
_cell_angle_gamma                90.0000
_cell_volume                     1230.9(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1503
_cell_measurement_theta_min      6.70
_cell_measurement_theta_max      68.40
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520.00
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_T_max  0.891

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54190
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            6085
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_theta_max         68.40
_diffrn_reflns_theta_full        68.40
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2228
_reflns_number_gt                1802
_reflns_threshold_expression     F>2.0σ(F)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1532
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2228
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.040
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.720
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.71482(9) 0.32431(10) 0.06766(13) 0.0205(4) Uani 1.0 4 d . . .
O3 O 0.90388(10) 0.17892(10) 0.20192(15) 0.0244(4) Uani 1.0 4 d . . .
O4 O 0.95805(10) 0.34702(11) 0.31934(15) 0.0263(4) Uani 1.0 4 d . . .
N2 N 0.57703(11) 0.34620(12) 0.41156(16) 0.0176(4) Uani 1.0 4 d . . .
C5 C 0.46550(13) 0.35348(14) 0.4057(2) 0.0182(4) Uani 1.0 4 d . . .
C6 C 0.61939(13) 0.41586(14) 0.32290(19) 0.0178(4) Uani 1.0 4 d . . .
C7 C 0.55369(15) 0.49709(14) 0.2207(2) 0.0221(4) Uani 1.0 4 d . . .
C8 C 0.39478(14) 0.43397(14) 0.3065(2) 0.0202(4) Uani 1.0 4 d . . .
C9 C 0.42105(14) 0.28020(15) 0.5016(2) 0.0230(4) Uani 1.0 4 d . . .
C10 C 0.74106(14) 0.40233(14) 0.3325(2) 0.0192(4) Uani 1.0 4 d . . .
C11 C 0.28064(14) 0.43796(15) 0.3077(3) 0.0247(5) Uani 1.0 4 d . . .
C12 C 0.76090(13) 0.30224(14) 0.23216(19) 0.0176(4) Uani 1.0 4 d . . .
C13 C 1.01998(14) 0.14801(16) 0.2166(2) 0.0248(5) Uani 1.0 4 d . . .
C14 C 0.44234(15) 0.50576(15) 0.2120(2) 0.0234(4) Uani 1.0 4 d . . .
C15 C 0.31051(14) 0.28665(16) 0.5003(3) 0.0262(5) Uani 1.0 4 d . . .
C16 C 0.88571(13) 0.28097(14) 0.25861(18) 0.0181(4) Uani 1.0 4 d . . .
C17 C 0.23980(15) 0.36628(16) 0.4019(3) 0.0270(5) Uani 1.0 4 d . . .
C18 C 1.07064(16) 0.09706(17) 0.3770(3) 0.0298(5) Uani 1.0 4 d . . .
H1 H 0.6478 0.3361 0.0512 0.0308 Uiso 1.0 4 calc R . .
H7 H 0.5859 0.5445 0.1595 0.0265 Uiso 1.0 4 calc R . .
H9 H 0.4668 0.2271 0.5662 0.0276 Uiso 1.0 4 calc R . .
H10A H 0.7819 0.3907 0.4428 0.0231 Uiso 1.0 4 calc R . .
H10B H 0.7687 0.4711 0.2950 0.0231 Uiso 1.0 4 calc R . .
H11 H 0.2334 0.4901 0.2435 0.0297 Uiso 1.0 4 calc R . .
H12 H 0.7259 0.2344 0.2626 0.0211 Uiso 1.0 4 calc R . .
H13A H 1.0617 0.2149 0.2024 0.0297 Uiso 1.0 4 calc R . .
H13B H 1.0237 0.0940 0.1339 0.0297 Uiso 1.0 4 calc R . .
H14 H 0.3985 0.5586 0.1444 0.0281 Uiso 1.0 4 calc R . .
H15 H 0.2821 0.2383 0.5646 0.0314 Uiso 1.0 4 calc R . .
H17 H 0.1650 0.3698 0.4014 0.0324 Uiso 1.0 4 calc R . .
H18A H 1.1468 0.0774 0.3849 0.0447 Uiso 1.0 4 calc R . .
H18B H 1.0299 0.0302 0.3902 0.0447 Uiso 1.0 4 calc R . .
H18C H 1.0677 0.1509 0.4587 0.0447 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b28'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b28'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C12 1.418(2) yes . .
O3 C13 1.463(3) yes . .
O3 C16 1.342(3) yes . .
O4 C16 1.204(2) yes . .
N2 C5 1.378(3) yes . .
N2 C6 1.325(3) yes . .
C5 C8 1.423(3) yes . .
C5 C9 1.409(3) yes . .
C6 C7 1.414(3) yes . .
C6 C10 1.502(3) yes . .
C7 C14 1.371(3) yes . .
C8 C11 1.423(3) yes . .
C8 C14 1.411(3) yes . .
C9 C15 1.374(3) yes . .
C10 C12 1.525(3) yes . .
C11 C17 1.363(3) yes . .
C12 C16 1.530(3) yes . .
C13 C18 1.497(3) yes . .
C15 C17 1.413(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C13 O3 C16 116.63(13) yes . . .
C5 N2 C6 119.20(14) yes . . .
N2 C5 C8 121.50(17) yes . . .
N2 C5 C9 119.04(15) yes . . .
C8 C5 C9 119.46(16) yes . . .
N2 C6 C7 122.23(16) yes . . .
N2 C6 C10 116.62(14) yes . . .
C7 C6 C10 121.13(16) yes . . .
C6 C7 C14 119.74(17) yes . . .
C5 C8 C11 118.60(17) yes . . .
C5 C8 C14 117.78(17) yes . . .
C11 C8 C14 123.62(16) yes . . .
C5 C9 C15 120.41(16) yes . . .
C6 C10 C12 111.12(13) yes . . .
C8 C11 C17 120.77(16) yes . . .
O1 C12 C10 110.47(13) yes . . .
O1 C12 C16 108.11(14) yes . . .
C10 C12 C16 110.45(13) yes . . .
O3 C13 C18 110.44(16) yes . . .
C7 C14 C8 119.54(16) yes . . .
C9 C15 C17 120.42(19) yes . . .
O3 C16 O4 124.33(16) yes . . .
O3 C16 C12 110.67(13) yes . . .
O4 C16 C12 124.99(16) yes . . .
C11 C17 C15 120.35(18) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        Ethyl-a-hydroxy(quinoline-2-yl)propanoate
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform:Methanol'
