# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1425933'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_date             2015-09-16T18:59:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
5-carboxyethyl-4-[4ethoxy(oxo)acetyl]-1-phenyl-1H-pyrazol
;
_chemical_name_common            
5-carboxyethyl-4-[4ethoxy(oxo)acetyl]-1-phenyl-1H-pyrazol
_chemical_formula_moiety         'C16 H16 N2 O5'
_chemical_formula_sum            'C16 H16 N2 O5'
_chemical_formula_weight         316.31
_chemical_melting_point          311K

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3305(2)
_cell_length_b                   10.6140(3)
_cell_length_c                   11.3269(3)
_cell_angle_alpha                67.3590(10)
_cell_angle_beta                 80.1190(10)
_cell_angle_gamma                81.5650(10)
_cell_volume                     798.16(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      3.236
_cell_measurement_theta_max      27.41

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.572
_exptl_crystal_size_min          0.49
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_absorpt_correction_T_min  0.8854
_exptl_absorpt_correction_T_max  0.96

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

_diffrn_source                   'sealed ceramic X ray tube'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measurement_device_type  'Bruker X8 Kappa APEX II diffractometer'
_diffrn_measurement_method       '0.5 ° ω & φ scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_number            23956
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             3670
_reflns_number_gt                3020
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker Instrument Service v2012.10.0.0'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (version 3.2i; Crystal Impact GbR, Bo'
_computing_publication_material  'APEX2 (version 2012.10-0; Bruker, 2012)'

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0692P)²+0.1903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3670
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1378
_refine_ls_wR_factor_gt          0.128
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.04

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

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
O52 O 0.69755(14) 0.22132(10) -0.02235(11) 0.0544(3) Uani 1 1 d . . .
O43 O 0.65082(15) -0.17923(10) 0.42219(10) 0.0533(3) Uani 1 1 d . . .
N1 N 0.30575(15) 0.25640(11) 0.04734(11) 0.0439(3) Uani 1 1 d . . .
O51 O 0.68430(17) -0.00149(11) 0.09421(13) 0.0700(4) Uani 1 1 d . . .
O41 O 0.28799(18) -0.14263(14) 0.39161(14) 0.0832(5) Uani 1 1 d . . .
O42 O 0.6424(2) 0.04867(12) 0.34940(14) 0.0776(4) Uani 1 1 d . . .
N2 N 0.13409(18) 0.25303(15) 0.11568(13) 0.0599(4) Uani 1 1 d . . .
C5 C 0.42267(18) 0.14880(13) 0.10933(12) 0.0399(3) Uani 1 1 d . . .
C4 C 0.3220(2) 0.07140(14) 0.22311(13) 0.0464(3) Uani 1 1 d . . .
C11 C 0.33420(18) 0.36429(13) -0.07717(13) 0.0417(3) Uani 1 1 d . . .
C12 C 0.3899(2) 0.33275(15) -0.18542(14) 0.0509(3) Uani 1 1 d . . .
H12 H 0.4123 0.2419 -0.1788 0.061 Uiso 1 1 calc R . .
C41 C 0.3853(2) -0.05171(15) 0.32820(14) 0.0497(3) Uani 1 1 d . . .
C13 C 0.4122(3) 0.43796(18) -0.30429(15) 0.0620(4) Uani 1 1 d . . .
H13 H 0.4514 0.418 -0.3782 0.074 Uiso 1 1 calc R . .
C42 C 0.5776(2) -0.05401(14) 0.36540(13) 0.0475(3) Uani 1 1 d . . .
C51 C 0.61557(19) 0.11441(13) 0.05984(13) 0.0420(3) Uani 1 1 d . . .
C43 C 0.8287(2) -0.19050(19) 0.4677(2) 0.0700(5) Uani 1 1 d . . .
H43A H 0.822 -0.1323 0.5169 0.084 Uiso 1 1 calc R . .
H43B H 0.9253 -0.1617 0.3951 0.084 Uiso 1 1 calc R . .
C14 C 0.3766(2) 0.57238(18) -0.31372(18) 0.0674(5) Uani 1 1 d . . .
H14 H 0.3913 0.643 -0.3939 0.081 Uiso 1 1 calc R . .
C52 C 0.8791(2) 0.1954(2) -0.09070(19) 0.0699(5) Uani 1 1 d . . .
H52A H 0.9743 0.1689 -0.0336 0.084 Uiso 1 1 calc R . .
H52B H 0.876 0.1221 -0.1213 0.084 Uiso 1 1 calc R . .
C44 C 0.8718(3) -0.3354(2) 0.5498(3) 0.0949(7) Uani 1 1 d . . .
H44A H 0.9891 -0.3454 0.5807 0.142 Uiso 1 1 calc R . .
H44B H 0.8781 -0.392 0.5003 0.142 Uiso 1 1 calc R . .
H44C H 0.7761 -0.3627 0.6217 0.142 Uiso 1 1 calc R . .
C15 C 0.3196(3) 0.60186(17) -0.2047(2) 0.0737(5) Uani 1 1 d . . .
H15 H 0.295 0.6927 -0.2115 0.088 Uiso 1 1 calc R . .
C16 C 0.2982(3) 0.49799(16) -0.08476(17) 0.0618(4) Uani 1 1 d . . .
H16 H 0.2603 0.518 -0.0108 0.074 Uiso 1 1 calc R . .
C3 C 0.1444(2) 0.14083(18) 0.22029(15) 0.0600(4) Uani 1 1 d . . .
H3 H 0.0453 0.1115 0.2845 0.072 Uiso 1 1 calc R . .
C53 C 0.9192(3) 0.3225(3) -0.1994(2) 0.1046(9) Uani 1 1 d . . .
H53A H 1.0377 0.3093 -0.2465 0.157 Uiso 1 1 calc R . .
H53B H 0.9219 0.3942 -0.1679 0.157 Uiso 1 1 calc R . .
H53C H 0.8243 0.3476 -0.2552 0.157 Uiso 1 1 calc R . .



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

_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
O52 C51 1.3078(16) . ?
O52 C52 1.4661(18) . ?
O43 C42 1.3113(17) . ?
O43 C43 1.4555(19) . ?
N1 C5 1.3542(16) . ?
N1 N2 1.3571(16) . ?
N1 C11 1.4386(17) . ?
O51 C51 1.1981(16) . ?
O41 C41 1.2035(18) . ?
O42 C42 1.1905(18) . ?
N2 C3 1.321(2) . ?
C5 C4 1.3845(18) . ?
C5 C51 1.4768(18) . ?
C4 C3 1.397(2) . ?
C4 C41 1.4676(19) . ?
C11 C12 1.373(2) . ?
C11 C16 1.377(2) . ?
C12 C13 1.381(2) . ?
C41 C42 1.533(2) . ?
C13 C14 1.378(3) . ?
C43 C44 1.479(3) . ?
C14 C15 1.371(3) . ?
C52 C53 1.461(3) . ?
C15 C16 1.382(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
C51 O52 C52 117.12(12) . . ?
C42 O43 C43 115.62(12) . . ?
C5 N1 N2 111.57(11) . . ?
C5 N1 C11 130.42(11) . . ?
N2 N1 C11 117.94(11) . . ?
C3 N2 N1 105.09(12) . . ?
N1 C5 C4 106.84(12) . . ?
N1 C5 C51 126.45(12) . . ?
C4 C5 C51 126.53(12) . . ?
C5 C4 C3 104.45(12) . . ?
C5 C4 C41 128.97(13) . . ?
C3 C4 C41 126.50(13) . . ?
C12 C11 C16 121.53(13) . . ?
C12 C11 N1 120.00(12) . . ?
C16 C11 N1 118.43(13) . . ?
C11 C12 C13 119.03(14) . . ?
O41 C41 C4 123.07(14) . . ?
O41 C41 C42 119.81(13) . . ?
C4 C41 C42 116.78(12) . . ?
C14 C13 C12 120.23(17) . . ?
O42 C42 O43 126.02(14) . . ?
O42 C42 C41 121.74(13) . . ?
O43 C42 C41 112.10(12) . . ?
O51 C51 O52 125.49(13) . . ?
O51 C51 C5 121.25(13) . . ?
O52 C51 C5 113.26(11) . . ?
O43 C43 C44 107.96(16) . . ?
C15 C14 C13 119.91(15) . . ?
C53 C52 O52 107.20(16) . . ?
C14 C15 C16 120.71(16) . . ?
C11 C16 C15 118.59(17) . . ?
N2 C3 C4 112.04(13) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
