# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rc196
_audit_block_doi                 10.5517/cc144rmn
_database_code_depnum_ccdc_archive 'CCDC 1047261'
_audit_update_record             
;
2015-08-03 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_date             2015-08-03T12:57:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H16 N2 O2, H2 O'
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.32
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  ' P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

_cell_length_a                   4.715(2)
_cell_length_b                   12.331(5)
_cell_length_c                   24.742(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1438.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273.15

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.2665
_exptl_crystal_F_000             584.2975

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_ambient_temperature      273.15
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.033
_diffrn_reflns_number            14732
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9979
_reflns_Friedel_coverage         0.996
_reflns_number_total             2806
_reflns_number_gt                2399
_reflns_threshold_expression     I>=2u(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.2464P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_reflns         2806
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.0783
_refine_ls_restrained_S_all      1.0783
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0E1(3)
_refine_diff_density_max         0.1886
_refine_diff_density_min         -0.2079
_refine_diff_density_rms         0.0454

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0 0 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

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_refinement_flags_posn
O1 O -0.0689(4) -0.79075(12) -0.71569(6) 0.0492(5) Uani 1 .
N1 N 0.3210(4) -0.67247(16) -0.77075(7) 0.0408(4) Uani 1 .
N2 N 0.4957(4) -0.61532(15) -0.80541(7) 0.0417(5) Uani 1 .
O2 O 0.1785(4) -0.51938(12) -0.72704(6) 0.0525(4) Uani 1 .
C5 C 0.1631(5) -0.61843(18) -0.73451(9) 0.0399(5) Uani 1 .
C7 C 0.8302(5) -0.62737(18) -0.87800(8) 0.0417(5) Uani 1 .
C4 C -0.0365(5) -0.68376(17) -0.70280(8) 0.0388(5) Uani 1 .
C6 C 0.6527(6) -0.67442(19) -0.83550(9) 0.0445(6) Uani 1 .
C12 C 0.8256(6) -0.5181(2) -0.89049(10) 0.0563(7) Uani 1 .
C10 C 1.1443(5) -0.54393(19) -0.96568(9) 0.0438(6) Uani 1 .
C3 C -0.2073(6) -0.6580(2) -0.66141(9) 0.0461(6) Uani 1 .
C13 C 1.2976(6) -0.5037(2) -1.01577(10) 0.0560(7) Uani 1 .
C2 C -0.3529(6) -0.7534(2) -0.64714(10) 0.0534(7) Uani 1 .
C11 C 0.9801(7) -0.4779(2) -0.93319(11) 0.0589(7) Uani 1 .
C1 C -0.2660(6) -0.8311(2) -0.68080(10) 0.0535(7) Uani 1 .
C9 C 1.1563(7) -0.6525(2) -0.95191(10) 0.0539(7) Uani 1 .
C8 C 1.0043(6) -0.6938(2) -0.90897(10) 0.0537(7) Uani 1 .
C14 C 1.1306(10) -0.5338(4) -1.06618(13) 0.0827(11) Uani 1 .
C15 C 1.3641(11) -0.3830(3) -1.01481(18) 0.0842(11) Uani 1 .
H6 H 0.655(5) -0.7557(18) -0.8323(8) 0.044(6) Uiso 1 .
H3 H -0.222(5) -0.5923(18) -0.6444(8) 0.039(6) Uiso 1 .
H1 H 0.305(5) -0.745(2) -0.7730(8) 0.044(6) Uiso 1 .
H12 H 0.713(6) -0.475(2) -0.8695(10) 0.062(8) Uiso 1 .
H2 H -0.483(5) -0.7598(18) -0.6206(9) 0.049(7) Uiso 1 .
H14a H 1.232(6) -0.516(2) -1.0958(12) 0.071(9) Uiso 1 .
H11 H 0.978(6) -0.404(2) -0.9396(11) 0.073(9) Uiso 1 .
H15a H 1.479(7) -0.364(2) -1.0430(12) 0.080(10) Uiso 1 .
H14b H 1.090(9) -0.606(3) -1.0661(14) 0.103(14) Uiso 1 .
H1a H -0.314(7) -0.902(2) -0.6853(10) 0.067(8) Uiso 1 .
H13 H 1.468(5) -0.5382(18) -1.0162(9) 0.037(6) Uiso 1 .
O4 O -0.3241(6) -0.39774(14) -0.70215(9) 0.0632(5) Uani 1 .
H4a H -0.460(10) -0.440(4) -0.7134(16) 0.124(16) Uiso 1 .
H4b H -0.174(8) -0.429(3) -0.7133(13) 0.081(11) Uiso 1 .
H9 H 1.269(5) -0.6986(19) -0.9719(9) 0.055(7) Uiso 1 .
H8 H 1.009(6) -0.762(2) -0.9006(10) 0.060(8) Uiso 1 .
H15b H 1.479(8) -0.360(3) -0.9778(15) 0.117(13) Uiso 1 .
H15c H 1.185(8) -0.352(2) -1.0163(12) 0.075(10) Uiso 1 .
H14c H 0.950(9) -0.494(3) -1.0663(16) 0.126(16) Uiso 1 .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

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 1.366(3) . ?
O1 C1 1.362(3) . ?
N1 N2 1.382(3) . ?
N1 C5 1.342(3) . ?
N1 H1 0.89(2) . ?
N2 C6 1.278(3) . ?
O2 C5 1.237(3) . ?
C5 C4 1.467(3) . ?
C7 C6 1.464(3) . ?
C7 C12 1.383(3) . ?
C7 C8 1.390(3) . ?
C4 C3 1.341(3) . ?
C6 H6 1.01(2) . ?
C12 C11 1.376(4) . ?
C12 H12 0.92(3) . ?
C10 C13 1.518(3) . ?
C10 C11 1.382(4) . ?
C10 C9 1.383(3) . ?
C3 C2 1.407(3) . ?
C3 H3 0.92(2) . ?
C13 C14 1.521(5) . ?
C13 C15 1.521(4) . ?
C13 H13 0.91(2) . ?
C2 C1 1.334(4) . ?
C2 H2 0.90(2) . ?
C11 H11 0.92(3) . ?
C1 H1a 0.91(3) . ?
C9 C8 1.379(4) . ?
C9 H9 0.92(2) . ?
C8 H8 0.87(3) . ?
C14 H14a 0.90(3) . ?
C14 H14b 0.91(4) . ?
C14 H14c 0.98(4) . ?
C15 H15a 0.92(3) . ?
C15 H15b 1.10(4) . ?
C15 H15c 0.93(4) . ?
O4 H4a 0.87(4) . ?
O4 H4b 0.85(4) . ?

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 O1 C4 106.32(19) . . ?
C5 N1 N2 119.45(19) . . ?
H1 N1 N2 121.2(15) . . ?
H1 N1 C5 119.3(15) . . ?
C6 N2 N1 114.57(19) . . ?
O2 C5 N1 123.9(2) . . ?
C4 C5 N1 116.14(19) . . ?
C4 C5 O2 120.0(2) . . ?
C12 C7 C6 122.5(2) . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 C12 117.4(2) . . ?
C5 C4 O1 118.52(18) . . ?
C3 C4 O1 109.9(2) . . ?
C3 C4 C5 131.6(2) . . ?
C7 C6 N2 121.6(2) . . ?
H6 C6 N2 121.9(13) . . ?
H6 C6 C7 116.5(13) . . ?
C11 C12 C7 121.0(3) . . ?
H12 C12 C7 116.9(15) . . ?
H12 C12 C11 122.1(15) . . ?
C11 C10 C13 123.3(2) . . ?
C9 C10 C13 119.9(2) . . ?
C9 C10 C11 116.8(2) . . ?
C2 C3 C4 106.7(2) . . ?
H3 C3 C4 127.4(14) . . ?
H3 C3 C2 125.9(14) . . ?
C14 C13 C10 110.1(2) . . ?
C15 C13 C10 113.9(2) . . ?
C15 C13 C14 111.0(3) . . ?
H13 C13 C10 106.2(14) . . ?
H13 C13 C14 109.5(14) . . ?
H13 C13 C15 105.9(14) . . ?
C1 C2 C3 107.1(2) . . ?
H2 C2 C3 126.1(15) . . ?
H2 C2 C1 126.8(15) . . ?
C10 C11 C12 122.1(3) . . ?
H11 C11 C12 118.8(17) . . ?
H11 C11 C10 119.1(17) . . ?
C2 C1 O1 110.0(2) . . ?
H1a C1 O1 116.4(18) . . ?
H1a C1 C2 133.5(18) . . ?
C8 C9 C10 121.7(3) . . ?
H9 C9 C10 119.2(15) . . ?
H9 C9 C8 119.0(15) . . ?
C9 C8 C7 121.0(3) . . ?
H8 C8 C7 117.1(17) . . ?
H8 C8 C9 121.9(17) . . ?
H14a C14 C13 109.3(19) . . ?
H14b C14 C13 110(2) . . ?
H14b C14 H14a 111(3) . . ?
H14c C14 C13 109(2) . . ?
H14c C14 H14a 110(3) . . ?
H14c C14 H14b 108(4) . . ?
H15a C15 C13 111.5(18) . . ?
H15b C15 C13 111.2(18) . . ?
H15b C15 H15a 106(3) . . ?
H15c C15 C13 102(2) . . ?
H15c C15 H15a 114(3) . . ?
H15c C15 H15b 112(3) . . ?
H4b O4 H4a 104(3) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
