# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1829783'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2014-10-08T15:26:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
'ethyl 5-(4-bromophenyl)-1-(tert-butyl)-1H-pyrazole-3-carboxylate'
;
_chemical_name_common            pyrazole
_chemical_formula_moiety         'C32 H38 Br2 N4 O4'
_chemical_formula_sum            'C32 H38 Br2 N4 O4'
_chemical_formula_weight         702.48
_chemical_melting_point          none

#----------------------------------------------------------------------------#
#                   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                   10.8799(6)
_cell_length_b                   13.3677(7)
_cell_length_c                   13.9345(8)
_cell_angle_alpha                62.953(3)
_cell_angle_beta                 68.018(3)
_cell_angle_gamma                82.371(3)
_cell_volume                     1672.04(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7057
_cell_measurement_theta_min      2.289
_cell_measurement_theta_max      26.6445

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

_exptl_crystal_description       tabular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.102
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_special_details           
;
'XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size'
;

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

_exptl_absorpt_coefficient_mu    2.464
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.51085
_exptl_absorpt_correction_T_max  0.80069

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_unetI/netI     0.052
_diffrn_reflns_number            45369
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.22
_diffrn_reflns_theta_full        27.22
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             7398
_reflns_number_gt                3820
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.0581P)²+1.2246P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         7398
_refine_ls_number_parameters     379
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.124
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.11
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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
Br1 Br 0.50520(6) 0.23924(5) 0.45584(4) 0.0882(2) Uani 1 1 d . . .
Br2 Br 0.75273(9) 0.56567(5) 0.41487(6) 0.1424(4) Uani 1 1 d . . .
N2 N 0.9176(3) 0.7070(3) -0.2111(3) 0.0511(8) Uani 1 1 d . . .
N1A N 0.5992(3) 1.1027(2) 0.0634(3) 0.0443(7) Uani 1 1 d . . .
N2A N 0.6088(3) 1.1942(2) -0.0358(3) 0.0474(8) Uani 1 1 d . . .
N1 N 0.8465(3) 0.6122(2) -0.1261(3) 0.0449(8) Uani 1 1 d . . .
O32A O 0.8517(3) 1.2300(2) -0.3036(2) 0.0685(9) Uani 1 1 d . . .
O1A O 0.6867(3) 1.3437(2) -0.2726(2) 0.0699(9) Uani 1 1 d . . .
C53 C 0.5402(4) 0.4524(4) 0.2629(3) 0.0558(11) Uani 1 1 d . . .
H53 H 0.4535 0.4632 0.3029 0.067 Uiso 1 1 calc R . .
C3A C 0.7096(4) 1.1763(3) -0.1161(3) 0.0458(9) Uani 1 1 d . . .
C54 C 0.6004(4) 0.3549(4) 0.3097(3) 0.0544(11) Uani 1 1 d . . .
C3 C 0.9266(4) 0.7657(3) -0.1574(4) 0.0495(10) Uani 1 1 d . . .
C51A C 0.7062(4) 0.9140(3) 0.1337(3) 0.0459(9) Uani 1 1 d . . .
C5 C 0.8126(4) 0.6096(3) -0.0197(3) 0.0453(9) Uani 1 1 d . . .
C11 C 0.8190(4) 0.5276(3) -0.1591(3) 0.0503(10) Uani 1 1 d . . .
C51 C 0.7385(4) 0.5189(3) 0.0930(3) 0.0446(9) Uani 1 1 d . . .
C56 C 0.7972(4) 0.4204(4) 0.1447(4) 0.0553(11) Uani 1 1 d . . .
H56 H 0.8846 0.4099 0.1059 0.066 Uiso 1 1 calc R . .
C52 C 0.6101(4) 0.5342(3) 0.1553(3) 0.0494(10) Uani 1 1 d . . .
H52 H 0.5703 0.6013 0.1237 0.059 Uiso 1 1 calc R . .
C4A C 0.7642(4) 1.0734(3) -0.0693(3) 0.0491(10) Uani 1 1 d . . .
H4A H 0.8355 1.043 -0.1084 0.059 Uiso 1 1 calc R . .
C11A C 0.4980(4) 1.1011(3) 0.1718(3) 0.0518(10) Uani 1 1 d . . .
C55 C 0.7290(4) 0.3377(4) 0.2519(4) 0.0600(11) Uani 1 1 d . . .
H55 H 0.769 0.2713 0.2848 0.072 Uiso 1 1 calc R . .
C56A C 0.6169(5) 0.8260(3) 0.1803(4) 0.0593(11) Uani 1 1 d . . .
H56A H 0.5459 0.8365 0.1553 0.071 Uiso 1 1 calc R . .
C31A C 0.7443(4) 1.2601(3) -0.2371(3) 0.0499(10) Uani 1 1 d . . .
C31 C 0.9987(4) 0.8744(4) -0.2183(5) 0.0680(13) Uani 1 1 d . . .
O32 O 1.0498(4) 0.9106(3) -0.3303(3) 0.1012(13) Uani 1 1 d . . .
C54A C 0.7371(6) 0.7068(4) 0.2971(4) 0.0758(15) Uani 1 1 d . . .
C5A C 0.6920(4) 1.0265(3) 0.0454(3) 0.0444(9) Uani 1 1 d . . .
C52A C 0.8154(5) 0.8952(4) 0.1661(4) 0.0635(12) Uani 1 1 d . . .
H52A H 0.879 0.9528 0.1328 0.076 Uiso 1 1 calc R . .
C53A C 0.8306(6) 0.7903(5) 0.2482(5) 0.0805(15) Uani 1 1 d . . .
H53A H 0.9046 0.7773 0.2697 0.097 Uiso 1 1 calc R . .
C4 C 0.8631(4) 0.7086(3) -0.0390(4) 0.0522(10) Uani 1 1 d . . .
H4 H 0.8562 0.7325 0.0159 0.063 Uiso 1 1 calc R . .
C33A C 0.8928(5) 1.2997(4) -0.4275(4) 0.0727(14) Uani 1 1 d . . .
H33A H 0.9877 1.2955 -0.4631 0.087 Uiso 1 1 calc R . .
H33B H 0.8739 1.3774 -0.443 0.087 Uiso 1 1 calc R . .
C14A C 0.4560(7) 1.2186(5) 0.1524(5) 0.116(2) Uani 1 1 d . . .
H14A H 0.4197 1.2494 0.0921 0.174 Uiso 1 1 calc R . .
H14B H 0.5315 1.2646 0.1305 0.174 Uiso 1 1 calc R . .
H14C H 0.3899 1.2168 0.2221 0.174 Uiso 1 1 calc R . .
O1 O 1.0091(4) 0.9259(3) -0.1711(4) 0.1066(14) Uani 1 1 d . . .
C55A C 0.6307(6) 0.7220(4) 0.2636(4) 0.0724(14) Uani 1 1 d . . .
H55A H 0.5685 0.6634 0.2963 0.087 Uiso 1 1 calc R . .
C14 C 0.6800(4) 0.4763(4) -0.0861(4) 0.0665(12) Uani 1 1 d . . .
H14D H 0.6173 0.5344 -0.0973 0.1 Uiso 1 1 calc R . .
H14E H 0.6711 0.4393 -0.0064 0.1 Uiso 1 1 calc R . .
H14F H 0.6633 0.4226 -0.1083 0.1 Uiso 1 1 calc R . .
C12 C 0.8264(6) 0.5874(5) -0.2834(4) 0.0907(18) Uani 1 1 d . . .
H12A H 0.914 0.6209 -0.3324 0.136 Uiso 1 1 calc R . .
H12B H 0.7628 0.645 -0.2914 0.136 Uiso 1 1 calc R . .
H12C H 0.8073 0.5343 -0.3051 0.136 Uiso 1 1 calc R . .
C34A C 0.8229(6) 1.2616(5) -0.4762(4) 0.1019(19) Uani 1 1 d . . .
H34A H 0.8492 1.3089 -0.5576 0.153 Uiso 1 1 calc R . .
H34B H 0.729 1.2652 -0.4403 0.153 Uiso 1 1 calc R . .
H34C H 0.844 1.1855 -0.4629 0.153 Uiso 1 1 calc R . .
C13 C 0.9206(6) 0.4380(5) -0.1432(6) 0.104(2) Uani 1 1 d . . .
H13A H 1.008 0.4721 -0.191 0.156 Uiso 1 1 calc R . .
H13B H 0.9045 0.3835 -0.1648 0.156 Uiso 1 1 calc R . .
H13C H 0.9136 0.4014 -0.0639 0.156 Uiso 1 1 calc R . .
C13A C 0.5547(7) 1.0546(6) 0.2656(5) 0.122(3) Uani 1 1 d . . .
H13D H 0.6305 1.1007 0.2427 0.183 Uiso 1 1 calc R . .
H13E H 0.5811 0.9793 0.2793 0.183 Uiso 1 1 calc R . .
H13F H 0.4889 1.0539 0.3349 0.183 Uiso 1 1 calc R . .
C33 C 1.1229(11) 1.0211(6) -0.3877(7) 0.178(4) Uani 1 1 d D . .
H33C H 1.0615 1.0778 -0.3765 0.213 Uiso 1 1 calc R . .
H33D H 1.1881 1.0159 -0.3537 0.213 Uiso 1 1 calc R . .
C12A C 0.3786(6) 1.0316(7) 0.2055(7) 0.143(3) Uani 1 1 d . . .
H12D H 0.3435 1.0629 0.1445 0.215 Uiso 1 1 calc R . .
H12E H 0.3124 1.0312 0.2745 0.215 Uiso 1 1 calc R . .
H12F H 0.4034 0.956 0.219 0.215 Uiso 1 1 calc R . .
C34 C 1.1831(11) 1.0503(8) -0.4995(8) 0.218(6) Uani 1 1 d D . .
H34D H 1.228 1.1226 -0.5367 0.327 Uiso 1 1 calc R . .
H34E H 1.1185 1.0539 -0.5326 0.327 Uiso 1 1 calc R . .
H34F H 1.2465 0.9955 -0.5103 0.327 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C54 1.896(4) . ?
Br2 C54A 1.895(4) . ?
N2 C3 1.340(5) . ?
N2 N1 1.347(4) . ?
N1A N2A 1.344(4) . ?
N1A C5A 1.376(5) . ?
N1A C11A 1.492(5) . ?
N2A C3A 1.329(5) . ?
N1 C5 1.372(5) . ?
N1 C11 1.499(5) . ?
O32A C31A 1.338(5) . ?
O32A C33A 1.456(5) . ?
O1A C31A 1.196(4) . ?
C53 C54 1.369(6) . ?
C53 C52 1.378(5) . ?
C3A C4A 1.388(5) . ?
C3A C31A 1.469(5) . ?
C54 C55 1.378(6) . ?
C3 C4 1.386(6) . ?
C3 C31 1.459(6) . ?
C51A C52A 1.378(6) . ?
C51A C56A 1.374(6) . ?
C51A C5A 1.482(5) . ?
C5 C4 1.373(5) . ?
C5 C51 1.472(5) . ?
C11 C14 1.510(5) . ?
C11 C12 1.516(6) . ?
C11 C13 1.516(6) . ?
C51 C52 1.387(5) . ?
C51 C56 1.385(5) . ?
C56 C55 1.374(6) . ?
C4A C5A 1.358(5) . ?
C11A C13A 1.495(7) . ?
C11A C12A 1.496(7) . ?
C11A C14A 1.505(6) . ?
C56A C55A 1.382(6) . ?
C31 O1 1.186(6) . ?
C31 O32 1.309(6) . ?
O32 C33 1.488(7) . ?
C54A C53A 1.355(7) . ?
C54A C55A 1.361(7) . ?
C52A C53A 1.387(6) . ?
C33A C34A 1.450(7) . ?
C33 C34 1.327(10) . ?

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 N2 N1 104.8(3) . . ?
N2A N1A C5A 111.4(3) . . ?
N2A N1A C11A 117.6(3) . . ?
C5A N1A C11A 131.0(3) . . ?
C3A N2A N1A 105.0(3) . . ?
N2 N1 C5 111.8(3) . . ?
N2 N1 C11 117.8(3) . . ?
C5 N1 C11 130.4(3) . . ?
C31A O32A C33A 116.9(3) . . ?
C54 C53 C52 118.9(4) . . ?
N2A C3A C4A 111.6(3) . . ?
N2A C3A C31A 119.0(3) . . ?
C4A C3A C31A 129.4(4) . . ?
C53 C54 C55 121.4(4) . . ?
C53 C54 Br1 119.8(3) . . ?
C55 C54 Br1 118.8(3) . . ?
N2 C3 C4 111.6(3) . . ?
N2 C3 C31 122.9(4) . . ?
C4 C3 C31 125.5(4) . . ?
C52A C51A C56A 118.7(4) . . ?
C52A C51A C5A 119.3(4) . . ?
C56A C51A C5A 121.9(4) . . ?
C4 C5 N1 106.1(3) . . ?
C4 C5 C51 126.6(4) . . ?
N1 C5 C51 127.3(3) . . ?
N1 C11 C14 110.2(3) . . ?
N1 C11 C12 108.7(3) . . ?
C14 C11 C12 107.3(4) . . ?
N1 C11 C13 108.6(3) . . ?
C14 C11 C13 110.8(4) . . ?
C12 C11 C13 111.3(4) . . ?
C52 C51 C56 117.8(4) . . ?
C52 C51 C5 120.3(3) . . ?
C56 C51 C5 121.7(3) . . ?
C55 C56 C51 121.5(4) . . ?
C53 C52 C51 121.5(4) . . ?
C5A C4A C3A 105.7(3) . . ?
C13A C11A N1A 110.1(4) . . ?
C13A C11A C12A 110.7(5) . . ?
N1A C11A C12A 109.0(4) . . ?
C13A C11A C14A 108.7(5) . . ?
N1A C11A C14A 109.9(3) . . ?
C12A C11A C14A 108.3(5) . . ?
C54 C55 C56 118.9(4) . . ?
C55A C56A C51A 121.1(4) . . ?
O1A C31A O32A 124.1(4) . . ?
O1A C31A C3A 125.9(4) . . ?
O32A C31A C3A 110.1(3) . . ?
O1 C31 O32 122.9(5) . . ?
O1 C31 C3 123.3(5) . . ?
O32 C31 C3 113.8(5) . . ?
C31 O32 C33 111.4(5) . . ?
C53A C54A C55A 121.3(4) . . ?
C53A C54A Br2 119.9(5) . . ?
C55A C54A Br2 118.7(4) . . ?
C4A C5A N1A 106.3(3) . . ?
C4A C5A C51A 127.3(4) . . ?
N1A C5A C51A 126.4(3) . . ?
C51A C52A C53A 120.1(4) . . ?
C54A C53A C52A 119.8(5) . . ?
C5 C4 C3 105.7(4) . . ?
O32A C33A C34A 110.0(4) . . ?
C54A C55A C56A 118.9(5) . . ?
C34 C33 O32 109.7(7) . . ?

# END of CIF
####################################################################### 
# 
# 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_mmq0215_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1833326'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2016-12-08T19:21:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
        'ethyl 1 tert-butyl-3-(4-bromophenyl)-1H-pyrazole-5-carboxylate'
;
_chemical_name_common            pyrazole-Br
_chemical_formula_moiety         'C16 H19 Br N2 O2'
_chemical_formula_sum            'C16 H19 Br N2 O2'
_chemical_formula_weight         351.24
_chemical_melting_point          none

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc
loop_
_symmetry_equiv_pos_as_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'
'-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                   26.040(3)
_cell_length_b                   9.0972(11)
_cell_length_c                   13.8867(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.957(10)
_cell_angle_gamma                90
_cell_volume                     3287.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      3.3945
_cell_measurement_theta_max      70.059

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_special_details           
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal
;

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

_exptl_absorpt_coefficient_mu    3.456
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.1814
_exptl_absorpt_correction_T_max  0.3458

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'phi and omega scnas'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_number            23652
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.4
_diffrn_reflns_theta_max         70.24
_diffrn_reflns_theta_full        70.24
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_reflns_number_total             3043
_reflns_number_gt                2882
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.0421P)²+2.8852P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
Br1 Br 0.312157(9) 0.62970(3) 0.613576(19) 0.07272(13) Uani 1 1 d . . .
O52 O 0.67868(5) 0.46614(16) 0.63690(11) 0.0594(4) Uani 1 1 d . . .
O2 O 0.69777(6) 0.2306(2) 0.65899(17) 0.0905(6) Uani 1 1 d . . .
N1 N 0.58313(6) 0.17901(17) 0.62968(12) 0.0473(4) Uani 1 1 d . . .
N2 N 0.53255(6) 0.20635(17) 0.62366(12) 0.0484(4) Uani 1 1 d . . .
C54 C 0.73806(11) 0.6581(4) 0.6203(2) 0.0918(9) Uani 1 1 d . . .
H54A H 0.7737 0.6853 0.6242 0.138 Uiso 1 1 calc R . .
H54B H 0.7194 0.7157 0.6653 0.138 Uiso 1 1 calc R . .
H54C H 0.7245 0.6758 0.5562 0.138 Uiso 1 1 calc R . .
C53 C 0.73287(8) 0.5011(3) 0.6437(2) 0.0696(6) Uani 1 1 d . . .
H53A H 0.7516 0.4416 0.5987 0.083 Uiso 1 1 calc R . .
H53B H 0.7465 0.4817 0.7083 0.083 Uiso 1 1 calc R . .
C51 C 0.66656(7) 0.3250(2) 0.64511(15) 0.0519(4) Uani 1 1 d . . .
C5 C 0.61029(7) 0.3079(2) 0.63501(13) 0.0434(4) Uani 1 1 d . . .
C4 C 0.57510(7) 0.4202(2) 0.63203(13) 0.0426(4) Uani 1 1 d . . .
H4 H 0.5818 0.5206 0.6341 0.051 Uiso 1 1 calc R . .
C3 C 0.52716(7) 0.35246(18) 0.62522(12) 0.0403(4) Uani 1 1 d . . .
C31 C 0.47573(6) 0.41913(19) 0.62078(12) 0.0397(4) Uani 1 1 d . . .
C32 C 0.46943(7) 0.5696(2) 0.62518(15) 0.0508(4) Uani 1 1 d . . .
H32 H 0.4983 0.6296 0.6299 0.061 Uiso 1 1 calc R . .
C33 C 0.42108(8) 0.6332(2) 0.62274(17) 0.0563(5) Uani 1 1 d . . .
H33 H 0.4174 0.7347 0.626 0.068 Uiso 1 1 calc R . .
C34 C 0.37867(7) 0.5441(2) 0.61544(13) 0.0502(4) Uani 1 1 d . . .
C11 C 0.60043(9) 0.0214(2) 0.63024(19) 0.0633(6) Uani 1 1 d . . .
C13 C 0.62631(12) -0.0116(3) 0.7280(2) 0.0894(9) Uani 1 1 d . . .
H13A H 0.6562 0.0494 0.737 0.134 Uiso 1 1 calc R . .
H13B H 0.6363 -0.1131 0.7306 0.134 Uiso 1 1 calc R . .
H13C H 0.6027 0.0081 0.7781 0.134 Uiso 1 1 calc R . .
C12 C 0.63564(11) -0.0042(3) 0.5470(2) 0.0870(8) Uani 1 1 d . . .
H12A H 0.6656 0.0565 0.5551 0.131 Uiso 1 1 calc R . .
H12B H 0.6178 0.0204 0.4875 0.131 Uiso 1 1 calc R . .
H12C H 0.6457 -0.1057 0.5458 0.131 Uiso 1 1 calc R . .
C14 C 0.55341(12) -0.0754(3) 0.6163(3) 0.1050(12) Uani 1 1 d . . .
H14A H 0.5308 -0.0604 0.6686 0.157 Uiso 1 1 calc R . .
H14B H 0.5638 -0.1766 0.6147 0.157 Uiso 1 1 calc R . .
H14C H 0.5358 -0.0505 0.5566 0.157 Uiso 1 1 calc R . .
C36 C 0.43197(7) 0.3325(2) 0.61311(16) 0.0540(5) Uani 1 1 d . . .
H36 H 0.4353 0.2309 0.6097 0.065 Uiso 1 1 calc R . .
C35 C 0.38354(8) 0.3945(2) 0.61037(17) 0.0596(5) Uani 1 1 d . . .
H35 H 0.3545 0.3352 0.6051 0.072 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C34 1.8986(18) . ?
O52 C51 1.328(3) . ?
O52 C53 1.446(2) . ?
O2 C51 1.194(3) . ?
N1 N2 1.340(2) . ?
N1 C5 1.370(2) . ?
N1 C11 1.503(2) . ?
N2 C3 1.337(2) . ?
C54 C53 1.473(4) . ?
C54 H54A 0.96 . ?
C54 H54B 0.96 . ?
C54 H54C 0.96 . ?
C53 H53A 0.97 . ?
C53 H53B 0.97 . ?
C51 C5 1.476(2) . ?
C5 C4 1.373(3) . ?
C4 C3 1.393(2) . ?
C4 H4 0.93 . ?
C3 C31 1.470(2) . ?
C31 C32 1.380(3) . ?
C31 C36 1.387(3) . ?
C32 C33 1.385(3) . ?
C32 H32 0.93 . ?
C33 C34 1.371(3) . ?
C33 H33 0.93 . ?
C34 C35 1.369(3) . ?
C11 C14 1.515(4) . ?
C11 C12 1.517(4) . ?
C11 C13 1.525(4) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C36 C35 1.381(3) . ?
C36 H36 0.93 . ?
C35 H35 0.93 . ?

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 C53 116.16(16) . . ?
N2 N1 C5 110.44(14) . . ?
N2 N1 C11 118.11(15) . . ?
C5 N1 C11 131.45(15) . . ?
C3 N2 N1 106.68(15) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O52 C53 C54 107.2(2) . . ?
O52 C53 H53A 110.3 . . ?
C54 C53 H53A 110.3 . . ?
O52 C53 H53B 110.3 . . ?
C54 C53 H53B 110.3 . . ?
H53A C53 H53B 108.5 . . ?
O2 C51 O52 123.19(19) . . ?
O2 C51 C5 127.4(2) . . ?
O52 C51 C5 109.41(16) . . ?
N1 C5 C4 107.01(15) . . ?
N1 C5 C51 127.23(16) . . ?
C4 C5 C51 125.73(17) . . ?
C5 C4 C3 105.57(16) . . ?
C5 C4 H4 127.2 . . ?
C3 C4 H4 127.2 . . ?
N2 C3 C4 110.30(15) . . ?
N2 C3 C31 120.38(16) . . ?
C4 C3 C31 129.32(16) . . ?
C32 C31 C36 117.94(17) . . ?
C32 C31 C3 121.13(16) . . ?
C36 C31 C3 120.93(16) . . ?
C31 C32 C33 121.50(18) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C34 C33 C32 118.97(18) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C35 C34 C33 121.06(18) . . ?
C35 C34 Br1 119.55(15) . . ?
C33 C34 Br1 119.39(16) . . ?
N1 C11 C14 108.23(18) . . ?
N1 C11 C12 109.34(19) . . ?
C14 C11 C12 108.7(3) . . ?
N1 C11 C13 108.4(2) . . ?
C14 C11 C13 109.3(2) . . ?
C12 C11 C13 112.8(2) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C35 C36 C31 121.15(19) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
C34 C35 C36 119.39(19) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C3 -0.1(2) . . . . ?
C11 N1 N2 C3 179.53(17) . . . . ?
C51 O52 C53 C54 172.8(2) . . . . ?
C53 O52 C51 O2 1.3(3) . . . . ?
C53 O52 C51 C5 -179.07(18) . . . . ?
N2 N1 C5 C4 -0.1(2) . . . . ?
C11 N1 C5 C4 -179.6(2) . . . . ?
N2 N1 C5 C51 178.17(18) . . . . ?
C11 N1 C5 C51 -1.4(3) . . . . ?
O2 C51 C5 N1 -7.3(4) . . . . ?
O52 C51 C5 N1 173.07(18) . . . . ?
O2 C51 C5 C4 170.7(2) . . . . ?
O52 C51 C5 C4 -9.0(3) . . . . ?
N1 C5 C4 C3 0.2(2) . . . . ?
C51 C5 C4 C3 -178.09(18) . . . . ?
N1 N2 C3 C4 0.2(2) . . . . ?
N1 N2 C3 C31 -179.32(15) . . . . ?
C5 C4 C3 N2 -0.3(2) . . . . ?
C5 C4 C3 C31 179.21(17) . . . . ?
N2 C3 C31 C32 178.07(18) . . . . ?
C4 C3 C31 C32 -1.4(3) . . . . ?
N2 C3 C31 C36 -1.2(3) . . . . ?
C4 C3 C31 C36 179.36(19) . . . . ?
C36 C31 C32 C33 0.4(3) . . . . ?
C3 C31 C32 C33 -178.85(19) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C32 C33 C34 Br1 179.26(16) . . . . ?
N2 N1 C11 C14 3.9(3) . . . . ?
C5 N1 C11 C14 -176.6(2) . . . . ?
N2 N1 C11 C12 122.1(2) . . . . ?
C5 N1 C11 C12 -58.3(3) . . . . ?
N2 N1 C11 C13 -114.5(2) . . . . ?
C5 N1 C11 C13 65.0(3) . . . . ?
C32 C31 C36 C35 -0.3(3) . . . . ?
C3 C31 C36 C35 179.02(19) . . . . ?
C33 C34 C35 C36 0.3(3) . . . . ?
Br1 C34 C35 C36 -179.10(17) . . . . ?
C31 C36 C35 C34 -0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13A O2 0.96 2.27 3.059(4) 139.1 .
C13 H13A O2 0.96 2.27 3.059(4) 139.1 .

# END of CIF
####################################################################### 
# 
# 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_mo_mmv0218_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1833325'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2016-12-16T13:10:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
'ethyl 1-(tert-butyl)-3-(4-chlorophenyl)-1H-pyrazole-5-carboxylate'
;
_chemical_name_common            1,5-pirazole-Cl
_chemical_formula_moiety         'C16 H19 Cl N2 O2'
_chemical_formula_sum            'C16 H19 Cl N2 O2'
_chemical_formula_weight         306.78
_chemical_melting_point          none

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/m
_symmetry_space_group_name_Hall  -P2yb
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.077(2)
_cell_length_b                   6.9098(15)
_cell_length_c                   13.708(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.735(7)
_cell_angle_gamma                90
_cell_volume                     819.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3740
_cell_measurement_theta_min      3.197
_cell_measurement_theta_max      26.857

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_special_details           
;
 SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal
;

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

_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_T_max  0.9696

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_number            10540
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.4
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_full        27.12
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_reflns_number_total             1940
_reflns_number_gt                1411
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.0652P)²+0.1389P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         1940
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.031

#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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
Cl1 Cl 0.45946(11) 0.25 0.14016(5) 0.0862(3) Uani 1 2 d S . .
O52 O 0.62327(19) 0.25 0.85949(11) 0.0659(5) Uani 1 2 d S . .
O1 O 0.4024(2) 0.25 0.89747(12) 0.0827(6) Uani 1 2 d S . .
N1 N 0.2498(2) 0.25 0.66691(13) 0.0524(5) Uani 1 2 d S . .
N2 N 0.2326(2) 0.25 0.56567(13) 0.0536(5) Uani 1 2 d S . .
C4 C 0.4844(2) 0.25 0.65270(14) 0.0457(5) Uani 1 2 d S . .
H4 H 0.5913 0.25 0.6669 0.055 Uiso 1 2 calc SR . .
C3 C 0.3743(2) 0.25 0.55650(15) 0.0436(5) Uani 1 2 d S . .
C5 C 0.4033(2) 0.25 0.72225(15) 0.0469(5) Uani 1 2 d S . .
C31 C 0.3958(2) 0.25 0.45403(14) 0.0437(5) Uani 1 2 d S . .
C51 C 0.4704(3) 0.25 0.83501(16) 0.0542(6) Uani 1 2 d S . .
C34 C 0.4355(3) 0.25 0.26144(17) 0.0575(6) Uani 1 2 d S . .
C32 C 0.5421(3) 0.25 0.44267(17) 0.0540(6) Uani 1 2 d S . .
H32 H 0.6284 0.25 0.5006 0.065 Uiso 1 2 calc SR . .
C36 C 0.2703(3) 0.25 0.36654(17) 0.0654(7) Uani 1 2 d S . .
H36 H 0.1708 0.25 0.3722 0.078 Uiso 1 2 calc SR . .
C33 C 0.5622(3) 0.25 0.34683(19) 0.0616(6) Uani 1 2 d S . .
H33 H 0.6613 0.25 0.3403 0.074 Uiso 1 2 calc SR . .
C11 C 0.1061(3) 0.25 0.69994(18) 0.0678(7) Uani 1 2 d S . .
C35 C 0.2905(3) 0.25 0.27042(17) 0.0715(7) Uani 1 2 d S . .
H35 H 0.2049 0.25 0.2121 0.086 Uiso 1 2 calc SR . .
C53 C 0.7054(3) 0.25 0.96867(18) 0.0849(9) Uani 1 2 d S . .
H53A H 0.6781 0.3639 1.0008 0.102 Uiso 0.5 1 calc PR . .
H53B H 0.6781 0.1361 1.0008 0.102 Uiso 0.5 1 calc PR . .
C54 C 0.8678(4) 0.25 0.9803(3) 0.1386(19) Uani 1 2 d S . .
H54A H 0.9252 0.25 1.0518 0.208 Uiso 1 2 calc SR . .
H54B H 0.8935 0.3634 0.9484 0.208 Uiso 0.5 1 calc PR . .
H54C H 0.8935 0.1366 0.9484 0.208 Uiso 0.5 1 calc PR . .
C12 C 0.1049(2) 0.0660(4) 0.76108(18) 0.0944(7) Uani 1 1 d . . .
H12A H 0.1057 -0.045 0.7191 0.142 Uiso 1 1 calc R . .
H12B H 0.0134 0.0635 0.7823 0.142 Uiso 1 1 calc R . .
H12C H 0.1947 0.0635 0.8204 0.142 Uiso 1 1 calc R . .
C13 C -0.0339(4) 0.25 0.6049(3) 0.1079(15) Uani 1 2 d S . .
H13A H -0.135(4) 0.25 0.630(3) 0.104(10) Uiso 1 2 d S . .
H13B H -0.041(3) 0.372(4) 0.563(2) 0.121(9) Uiso 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C34 1.741(2) . ?
O52 C51 1.324(3) . ?
O52 C53 1.455(3) . ?
O1 C51 1.198(3) . ?
N1 N2 1.348(2) . ?
N1 C5 1.369(3) . ?
N1 C11 1.505(3) . ?
N2 C3 1.330(3) . ?
C4 C5 1.370(3) . ?
C4 C3 1.391(3) . ?
C4 H4 0.93 . ?
C3 C31 1.476(3) . ?
C5 C51 1.479(3) . ?
C31 C36 1.379(3) . ?
C31 C32 1.383(3) . ?
C34 C35 1.359(4) . ?
C34 C33 1.368(4) . ?
C32 C33 1.381(3) . ?
C32 H32 0.93 . ?
C36 C35 1.384(3) . ?
C36 H36 0.93 . ?
C33 H33 0.93 . ?
C11 C13 1.518(4) . ?
C11 C12 1.525(3) 4_565 ?
C11 C12 1.525(3) . ?
C35 H35 0.93 . ?
C53 C54 1.434(5) . ?
C53 H53A 0.97 . ?
C53 H53B 0.97 . ?
C54 H54A 0.96 . ?
C54 H54B 0.96 . ?
C54 H54C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 1.07(4) . ?
C13 H13B 1.01(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 C53 115.44(19) . . ?
N2 N1 C5 110.46(17) . . ?
N2 N1 C11 118.06(17) . . ?
C5 N1 C11 131.48(17) . . ?
C3 N2 N1 106.57(16) . . ?
C5 C4 C3 106.06(19) . . ?
C5 C4 H4 127 . . ?
C3 C4 H4 127 . . ?
N2 C3 C4 110.27(18) . . ?
N2 C3 C31 120.13(18) . . ?
C4 C3 C31 129.59(19) . . ?
N1 C5 C4 106.63(18) . . ?
N1 C5 C51 127.25(19) . . ?
C4 C5 C51 126.1(2) . . ?
C36 C31 C32 117.9(2) . . ?
C36 C31 C3 120.93(19) . . ?
C32 C31 C3 121.12(18) . . ?
O1 C51 O52 123.1(2) . . ?
O1 C51 C5 127.5(2) . . ?
O52 C51 C5 109.35(18) . . ?
C35 C34 C33 120.5(2) . . ?
C35 C34 Cl1 119.5(2) . . ?
C33 C34 Cl1 120.0(2) . . ?
C33 C32 C31 121.1(2) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C31 C36 C35 120.9(2) . . ?
C31 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C34 C33 C32 119.6(2) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
N1 C11 C13 108.5(2) . . ?
N1 C11 C12 108.52(14) . 4_565 ?
C13 C11 C12 109.09(15) . 4_565 ?
N1 C11 C12 108.52(14) . . ?
C13 C11 C12 109.09(15) . . ?
C12 C11 C12 113.0(2) 4_565 . ?
C34 C35 C36 119.9(2) . . ?
C34 C35 H35 120 . . ?
C36 C35 H35 120 . . ?
C54 C53 O52 107.6(2) . . ?
C54 C53 H53A 110.2 . . ?
O52 C53 H53A 110.2 . . ?
C54 C53 H53B 110.2 . . ?
O52 C53 H53B 110.2 . . ?
H53A C53 H53B 108.5 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 107.1(18) . . ?
C11 C13 H13B 112.2(16) . . ?
H13A C13 H13B 105.9(17) . . ?

# END of CIF
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1833320'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2018-03-28T14:05:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
        'ethyl-5-(phenyl)-1-(t-butyl)-1H-pyrazole-3-carboxylate'
;
_chemical_name_common            1,3-Ph-pyrazole
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_chemical_melting_point          none

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

_symmetry_Int_Tables_number      14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0704(9)
_cell_length_b                   10.6122(13)
_cell_length_c                   17.698(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.130(11)
_cell_angle_gamma                90
_cell_volume                     1513.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.498
_cell_measurement_theta_max      68.241
_cell_measurement_wavelength     1.54178

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_special_details           
;
'SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal'
;

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

_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.8371
_exptl_absorpt_correction_T_max  0.9051

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_number            13793
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.01
_diffrn_reflns_theta_max         68.33
_diffrn_reflns_theta_full        68.33
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_reflns_number_total             2685
_reflns_number_gt                2432
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.0978P)²+0.8506P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         2685
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.077
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.1967
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.43
_refine_diff_density_rms         0.041

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


#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 O 0.1852(3) 0.15231(17) 0.40960(12) 0.0783(6) Uani 1 1 d . . .
O32 O 0.0297(3) 0.30372(18) 0.45733(13) 0.0824(7) Uani 1 1 d . . .
N2 N 0.3975(2) 0.33999(16) 0.35980(10) 0.0486(5) Uani 1 1 d . . .
N1 N 0.4653(2) 0.45256(16) 0.34509(10) 0.0458(5) Uani 1 1 d . . .
C54 C 0.4675(3) 0.9451(2) 0.36380(17) 0.0678(7) Uani 1 1 d . . .
H54 H 0.4858 1.0316 0.3626 0.081 Uiso 1 1 calc R . .
C55 C 0.3792(3) 0.8870(2) 0.30524(15) 0.0627(6) Uani 1 1 d . . .
H55 H 0.3379 0.9343 0.2642 0.075 Uiso 1 1 calc R . .
C56 C 0.3514(3) 0.7589(2) 0.30676(13) 0.0534(6) Uani 1 1 d . . .
H56 H 0.2909 0.7206 0.2669 0.064 Uiso 1 1 calc R . .
C51 C 0.4128(2) 0.6867(2) 0.36742(12) 0.0456(5) Uani 1 1 d . . .
C5 C 0.3747(3) 0.54995(19) 0.37261(11) 0.0443(5) Uani 1 1 d . . .
C4 C 0.2441(3) 0.4960(2) 0.40666(12) 0.0489(5) Uani 1 1 d . . .
H4 H 0.1604 0.537 0.4311 0.059 Uiso 1 1 calc R . .
C3 C 0.2632(3) 0.3663(2) 0.39703(11) 0.0461(5) Uani 1 1 d . . .
C31 C 0.1597(3) 0.2609(2) 0.42121(13) 0.0552(6) Uani 1 1 d . . .
C33 C -0.0889(4) 0.2074(3) 0.4810(2) 0.0868(9) Uani 1 1 d . . .
H33A H -0.199 0.2434 0.4832 0.104 Uiso 1 1 calc R . .
H33B H -0.0941 0.1379 0.4453 0.104 Uiso 1 1 calc R . .
C34 C -0.0300(5) 0.1647(4) 0.5539(2) 0.0998(11) Uani 1 1 d . . .
H34A H -0.104 0.1017 0.5715 0.15 Uiso 1 1 calc R . .
H34B H -0.0254 0.2344 0.5886 0.15 Uiso 1 1 calc R . .
H34C H 0.0789 0.1294 0.5509 0.15 Uiso 1 1 calc R . .
C53 C 0.5287(3) 0.8749(3) 0.42435(17) 0.0704(7) Uani 1 1 d . . .
H53 H 0.589 0.9138 0.4641 0.084 Uiso 1 1 calc R . .
C52 C 0.5007(3) 0.7463(2) 0.42630(14) 0.0599(6) Uani 1 1 d . . .
H52 H 0.5414 0.6995 0.4677 0.072 Uiso 1 1 calc R . .
C11 C 0.6211(3) 0.4556(2) 0.30265(14) 0.0542(6) Uani 1 1 d . . .
C13 C 0.5863(4) 0.5271(3) 0.22866(15) 0.0733(8) Uani 1 1 d . . .
H13A H 0.5547 0.6122 0.2396 0.11 Uiso 1 1 calc R . .
H13B H 0.4979 0.4864 0.1995 0.11 Uiso 1 1 calc R . .
H13C H 0.6844 0.5278 0.2003 0.11 Uiso 1 1 calc R . .
C12 C 0.6704(4) 0.3218(3) 0.2846(2) 0.0893(10) Uani 1 1 d . . .
H12A H 0.5826 0.2822 0.2545 0.134 Uiso 1 1 calc R . .
H12B H 0.6903 0.2755 0.3308 0.134 Uiso 1 1 calc R . .
H12C H 0.7696 0.3227 0.257 0.134 Uiso 1 1 calc R . .
C14 C 0.7576(3) 0.5205(4) 0.3505(2) 0.0864(9) Uani 1 1 d . . .
H14A H 0.724 0.6051 0.3615 0.13 Uiso 1 1 calc R . .
H14B H 0.8573 0.5226 0.3233 0.13 Uiso 1 1 calc R . .
H14C H 0.7777 0.475 0.397 0.13 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C31 1.191(3) . ?
O32 C31 1.338(3) . ?
O32 C33 1.476(4) . ?
N2 C3 1.329(3) . ?
N2 N1 1.345(2) . ?
N1 C5 1.371(3) . ?
N1 C11 1.500(3) . ?
C54 C55 1.372(4) . ?
C54 C53 1.375(4) . ?
C54 H54 0.93 . ?
C55 C56 1.378(3) . ?
C55 H55 0.93 . ?
C56 C51 1.388(3) . ?
C56 H56 0.93 . ?
C51 C52 1.381(3) . ?
C51 C5 1.488(3) . ?
C5 C4 1.368(3) . ?
C4 C3 1.396(3) . ?
C4 H4 0.93 . ?
C3 C31 1.473(3) . ?
C33 C34 1.425(5) . ?
C33 H33A 0.97 . ?
C33 H33B 0.97 . ?
C34 H34A 0.96 . ?
C34 H34B 0.96 . ?
C34 H34C 0.96 . ?
C53 C52 1.384(4) . ?
C53 H53 0.93 . ?
C52 H52 0.93 . ?
C11 C12 1.514(4) . ?
C11 C14 1.518(4) . ?
C11 C13 1.526(4) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?

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
C31 O32 C33 115.9(2) . . ?
C3 N2 N1 105.12(17) . . ?
N2 N1 C5 111.75(17) . . ?
N2 N1 C11 118.47(16) . . ?
C5 N1 C11 129.78(17) . . ?
C55 C54 C53 119.6(2) . . ?
C55 C54 H54 120.2 . . ?
C53 C54 H54 120.2 . . ?
C54 C55 C56 120.5(2) . . ?
C54 C55 H55 119.7 . . ?
C56 C55 H55 119.7 . . ?
C55 C56 C51 120.5(2) . . ?
C55 C56 H56 119.8 . . ?
C51 C56 H56 119.8 . . ?
C52 C51 C56 118.6(2) . . ?
C52 C51 C5 119.9(2) . . ?
C56 C51 C5 121.32(19) . . ?
C4 C5 N1 106.22(18) . . ?
C4 C5 C51 127.08(19) . . ?
N1 C5 C51 126.69(18) . . ?
C5 C4 C3 105.46(18) . . ?
C5 C4 H4 127.3 . . ?
C3 C4 H4 127.3 . . ?
N2 C3 C4 111.45(19) . . ?
N2 C3 C31 118.41(19) . . ?
C4 C3 C31 130.1(2) . . ?
O1 C31 O32 124.0(2) . . ?
O1 C31 C3 125.3(2) . . ?
O32 C31 C3 110.7(2) . . ?
C34 C33 O32 106.7(3) . . ?
C34 C33 H33A 110.4 . . ?
O32 C33 H33A 110.4 . . ?
C34 C33 H33B 110.4 . . ?
O32 C33 H33B 110.4 . . ?
H33A C33 H33B 108.6 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C54 C53 C52 120.1(2) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C51 C52 C53 120.7(2) . . ?
C51 C52 H52 119.7 . . ?
C53 C52 H52 119.7 . . ?
N1 C11 C12 108.84(19) . . ?
N1 C11 C14 109.4(2) . . ?
C12 C11 C14 110.6(2) . . ?
N1 C11 C13 108.69(18) . . ?
C12 C11 C13 108.9(2) . . ?
C14 C11 C13 110.3(2) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 N1 C5 -0.1(2) . . . . ?
C3 N2 N1 C11 -179.76(17) . . . . ?
C53 C54 C55 C56 0.1(4) . . . . ?
C54 C55 C56 C51 -0.3(4) . . . . ?
C55 C56 C51 C52 0.7(3) . . . . ?
C55 C56 C51 C5 175.9(2) . . . . ?
N2 N1 C5 C4 0.4(2) . . . . ?
C11 N1 C5 C4 180.0(2) . . . . ?
N2 N1 C5 C51 179.46(19) . . . . ?
C11 N1 C5 C51 -0.9(3) . . . . ?
C52 C51 C5 C4 84.5(3) . . . . ?
C56 C51 C5 C4 -90.6(3) . . . . ?
C52 C51 C5 N1 -94.4(3) . . . . ?
C56 C51 C5 N1 90.5(3) . . . . ?
N1 C5 C4 C3 -0.4(2) . . . . ?
C51 C5 C4 C3 -179.5(2) . . . . ?
N1 N2 C3 C4 -0.2(2) . . . . ?
N1 N2 C3 C31 179.71(18) . . . . ?
C5 C4 C3 N2 0.4(2) . . . . ?
C5 C4 C3 C31 -179.5(2) . . . . ?
C33 O32 C31 O1 -2.1(4) . . . . ?
C33 O32 C31 C3 176.9(2) . . . . ?
N2 C3 C31 O1 -0.7(4) . . . . ?
C4 C3 C31 O1 179.2(3) . . . . ?
N2 C3 C31 O32 -179.6(2) . . . . ?
C4 C3 C31 O32 0.2(3) . . . . ?
C31 O32 C33 C34 87.9(3) . . . . ?
C55 C54 C53 C52 -0.3(4) . . . . ?
C56 C51 C52 C53 -0.9(4) . . . . ?
C5 C51 C52 C53 -176.1(2) . . . . ?
C54 C53 C52 C51 0.7(4) . . . . ?
N2 N1 C11 C12 0.0(3) . . . . ?
C5 N1 C11 C12 -179.5(2) . . . . ?
N2 N1 C11 C14 -121.0(2) . . . . ?
C5 N1 C11 C14 59.4(3) . . . . ?
N2 N1 C11 C13 118.5(2) . . . . ?
C5 N1 C11 C13 -61.1(3) . . . . ?


# END of CIF
####################################################################### 
# 
# 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_mmq0163_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1833321'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2016-09-13T10:43:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
        'ethyl 1-(t-butil)-5-(4-fluorophenyl)-1H-pyrazole-3-carboxylate'
;
_chemical_name_common            'pyrazole 1,3 F'
_chemical_formula_moiety         'C16 H19 F N2 O2'
_chemical_formula_sum            'C16 H19 F N2 O2'
_chemical_formula_weight         290.33
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9381(7)
_cell_length_b                   18.463(3)
_cell_length_c                   12.600(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.702(10)
_cell_angle_gamma                90
_cell_volume                     1568.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9835
_cell_measurement_theta_min      2.392
_cell_measurement_theta_max      71.9495

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_special_details           
;
        SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal
;

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

_exptl_absorpt_coefficient_mu    0.74
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.8156
_exptl_absorpt_correction_T_max  0.8951

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_number            29117
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         72.13
_diffrn_reflns_theta_full        72.13
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_reflns_number_total             3058
_reflns_number_gt                2598
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.0713P)²+0.2686P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
O32 O 0.27282(16) 0.59670(6) 0.89581(9) 0.0582(3) Uani 1 1 d . . .
O1 O 0.37984(18) 0.48592(6) 0.86502(9) 0.0640(3) Uani 1 1 d . . .
N1 N 0.59997(16) 0.67313(6) 0.69985(9) 0.0438(3) Uani 1 1 d . . .
N2 N 0.48852(16) 0.65910(6) 0.77179(9) 0.0455(3) Uani 1 1 d . . .
C34 C 0.0091(3) 0.62369(12) 0.97898(17) 0.0783(5) Uani 1 1 d . . .
H34A H -0.0788 0.6044 1.0203 0.117 Uiso 1 1 calc R . .
H34B H -0.0671 0.6424 0.9108 0.117 Uiso 1 1 calc R . .
H34C H 0.0868 0.662 1.0196 0.117 Uiso 1 1 calc R . .
C33 C 0.1429(3) 0.56543(10) 0.95765(16) 0.0698(5) Uani 1 1 d . . .
H33A H 0.22 0.5459 1.0261 0.084 Uiso 1 1 calc R . .
H33B H 0.0658 0.5264 0.9166 0.084 Uiso 1 1 calc R . .
C31 C 0.3812(2) 0.55052(8) 0.85322(11) 0.0459(3) Uani 1 1 d . . .
C3 C 0.49754(18) 0.58753(7) 0.78540(10) 0.0428(3) Uani 1 1 d . . .
C4 C 0.61538(19) 0.55524(7) 0.72311(11) 0.0455(3) Uani 1 1 d . . .
H4 H 0.644 0.5062 0.7192 0.055 Uiso 1 1 calc R . .
C5 C 0.68011(18) 0.61105(7) 0.66880(10) 0.0431(3) Uani 1 1 d . . .
C51 C 0.80432(19) 0.60559(7) 0.58810(11) 0.0444(3) Uani 1 1 d . . .
C56 C 1.0056(2) 0.62114(9) 0.61580(12) 0.0538(4) Uani 1 1 d . . .
H56 H 1.065 0.6362 0.6864 0.065 Uiso 1 1 calc R . .
C55 C 1.1191(2) 0.61444(10) 0.53966(13) 0.0606(4) Uani 1 1 d . . .
H55 H 1.2535 0.6257 0.5579 0.073 Uiso 1 1 calc R . .
C54 C 1.0292(2) 0.59092(8) 0.43724(13) 0.0572(4) Uani 1 1 d . . .
C11 C 0.6208(2) 0.75090(8) 0.66802(12) 0.0548(4) Uani 1 1 d . . .
C12 C 0.5826(4) 0.75697(11) 0.54442(14) 0.0834(6) Uani 1 1 d . . .
H12A H 0.6781 0.7283 0.5191 0.125 Uiso 1 1 calc R . .
H12B H 0.5943 0.8067 0.5245 0.125 Uiso 1 1 calc R . .
H12C H 0.4514 0.7398 0.5117 0.125 Uiso 1 1 calc R . .
C13 C 0.8286(3) 0.77671(10) 0.72171(19) 0.0807(6) Uani 1 1 d . . .
H13A H 0.9237 0.7483 0.6956 0.121 Uiso 1 1 calc R . .
H13B H 0.8515 0.7714 0.7995 0.121 Uiso 1 1 calc R . .
H13C H 0.8421 0.8267 0.704 0.121 Uiso 1 1 calc R . .
C14 C 0.4701(3) 0.79615(9) 0.70870(17) 0.0746(5) Uani 1 1 d . . .
H14A H 0.4946 0.7921 0.7867 0.112 Uiso 1 1 calc R . .
H14B H 0.3388 0.779 0.676 0.112 Uiso 1 1 calc R . .
H14C H 0.4817 0.8459 0.6891 0.112 Uiso 1 1 calc R . .
C52 C 0.7200(2) 0.58066(8) 0.48350(12) 0.0517(3) Uani 1 1 d . . .
H52 H 0.586 0.5688 0.4646 0.062 Uiso 1 1 calc R . .
C53 C 0.8326(2) 0.57323(9) 0.40695(12) 0.0570(4) Uani 1 1 d . . .
H53 H 0.7759 0.5567 0.3368 0.068 Uiso 1 1 calc R . .
F1 F 1.14062(17) 0.58491(6) 0.36226(9) 0.0849(4) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O32 C31 1.3308(17) . ?
O32 C33 1.4442(17) . ?
O1 C31 1.2023(17) . ?
N1 N2 1.3486(14) . ?
N1 C5 1.3709(17) . ?
N1 C11 1.5068(18) . ?
N2 C3 1.3321(18) . ?
C34 C33 1.486(3) . ?
C34 H34A 0.96 . ?
C34 H34B 0.96 . ?
C34 H34C 0.96 . ?
C33 H33A 0.97 . ?
C33 H33B 0.97 . ?
C31 C3 1.4750(17) . ?
C3 C4 1.3942(17) . ?
C4 C5 1.3702(19) . ?
C4 H4 0.93 . ?
C5 C51 1.4838(17) . ?
C51 C56 1.387(2) . ?
C51 C52 1.388(2) . ?
C56 C55 1.383(2) . ?
C56 H56 0.93 . ?
C55 C54 1.364(2) . ?
C55 H55 0.93 . ?
C54 F1 1.3598(16) . ?
C54 C53 1.366(2) . ?
C11 C13 1.517(2) . ?
C11 C14 1.519(2) . ?
C11 C12 1.521(2) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C52 C53 1.3839(19) . ?
C52 H52 0.93 . ?
C53 H53 0.93 . ?

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
C31 O32 C33 116.48(12) . . ?
N2 N1 C5 111.54(10) . . ?
N2 N1 C11 117.92(11) . . ?
C5 N1 C11 130.53(11) . . ?
C3 N2 N1 105.08(10) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O32 C33 C34 107.74(15) . . ?
O32 C33 H33A 110.2 . . ?
C34 C33 H33A 110.2 . . ?
O32 C33 H33B 110.2 . . ?
C34 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
O1 C31 O32 124.34(12) . . ?
O1 C31 C3 123.53(12) . . ?
O32 C31 C3 112.08(12) . . ?
N2 C3 C4 111.57(11) . . ?
N2 C3 C31 121.24(12) . . ?
C4 C3 C31 127.05(13) . . ?
C5 C4 C3 105.36(12) . . ?
C5 C4 H4 127.3 . . ?
C3 C4 H4 127.3 . . ?
C4 C5 N1 106.45(11) . . ?
C4 C5 C51 127.12(12) . . ?
N1 C5 C51 126.37(12) . . ?
C56 C51 C52 118.70(13) . . ?
C56 C51 C5 121.81(12) . . ?
C52 C51 C5 119.40(12) . . ?
C55 C56 C51 120.77(14) . . ?
C55 C56 H56 119.6 . . ?
C51 C56 H56 119.6 . . ?
C54 C55 C56 118.47(14) . . ?
C54 C55 H55 120.8 . . ?
C56 C55 H55 120.8 . . ?
F1 C54 C55 118.38(15) . . ?
F1 C54 C53 118.74(15) . . ?
C55 C54 C53 122.88(13) . . ?
N1 C11 C13 108.75(13) . . ?
N1 C11 C14 108.50(12) . . ?
C13 C11 C14 109.52(15) . . ?
N1 C11 C12 109.78(12) . . ?
C13 C11 C12 110.49(15) . . ?
C14 C11 C12 109.77(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C53 C52 C51 120.96(14) . . ?
C53 C52 H52 119.5 . . ?
C51 C52 H52 119.5 . . ?
C54 C53 C52 118.19(14) . . ?
C54 C53 H53 120.9 . . ?
C52 C53 H53 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 C3 -0.46(14) . . . . ?
C11 N1 N2 C3 -179.47(11) . . . . ?
C31 O32 C33 C34 -169.16(15) . . . . ?
C33 O32 C31 O1 -1.6(2) . . . . ?
C33 O32 C31 C3 175.94(13) . . . . ?
N1 N2 C3 C4 0.38(15) . . . . ?
N1 N2 C3 C31 -175.59(11) . . . . ?
O1 C31 C3 N2 177.57(14) . . . . ?
O32 C31 C3 N2 0.05(18) . . . . ?
O1 C31 C3 C4 2.3(2) . . . . ?
O32 C31 C3 C4 -175.24(13) . . . . ?
N2 C3 C4 C5 -0.17(15) . . . . ?
C31 C3 C4 C5 175.51(13) . . . . ?
C3 C4 C5 N1 -0.11(14) . . . . ?
C3 C4 C5 C51 -177.41(12) . . . . ?
N2 N1 C5 C4 0.36(14) . . . . ?
C11 N1 C5 C4 179.21(13) . . . . ?
N2 N1 C5 C51 177.69(12) . . . . ?
C11 N1 C5 C51 -3.5(2) . . . . ?
C4 C5 C51 C56 -102.05(17) . . . . ?
N1 C5 C51 C56 81.16(18) . . . . ?
C4 C5 C51 C52 74.50(18) . . . . ?
N1 C5 C51 C52 -102.28(17) . . . . ?
C52 C51 C56 C55 2.3(2) . . . . ?
C5 C51 C56 C55 178.85(14) . . . . ?
C51 C56 C55 C54 -1.2(2) . . . . ?
C56 C55 C54 F1 179.49(14) . . . . ?
C56 C55 C54 C53 -0.5(3) . . . . ?
N2 N1 C11 C13 107.09(15) . . . . ?
C5 N1 C11 C13 -71.70(18) . . . . ?
N2 N1 C11 C14 -11.97(18) . . . . ?
C5 N1 C11 C14 169.24(15) . . . . ?
N2 N1 C11 C12 -131.92(15) . . . . ?
C5 N1 C11 C12 49.3(2) . . . . ?
C56 C51 C52 C53 -1.8(2) . . . . ?
C5 C51 C52 C53 -178.44(13) . . . . ?
F1 C54 C53 C52 -179.01(13) . . . . ?
C55 C54 C53 C52 1.0(2) . . . . ?
C51 C52 C53 C54 0.2(2) . . . . ?

# END of CIF
####################################################################### 
# 
# 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_dfb1
_database_code_depnum_ccdc_archive 'CCDC 1833323'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2017-03-26T11:02:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
'ethyl 1 tert-butyl-3-(4-fluorophenyl)-1H-pyrazole-5-carboxylate'
;
_chemical_name_common            pyrazole
_chemical_formula_moiety         'C16 H19 F N2 O2'
_chemical_formula_sum            'C16 H19 F N2 O2'
_chemical_formula_weight         290.33
_chemical_melting_point          none

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

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

_cell_length_a                   8.5662(3)
_cell_length_b                   8.9965(3)
_cell_length_c                   10.0893(4)
_cell_angle_alpha                92.860(2)
_cell_angle_beta                 100.776(2)
_cell_angle_gamma                91.266(2)
_cell_volume                     762.49(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9163
_cell_measurement_theta_min      2.268
_cell_measurement_theta_max      26.955

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.746
_exptl_crystal_size_mid          0.491
_exptl_crystal_size_min          0.387
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_special_details           
;
        XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;

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

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.99738
_exptl_absorpt_correction_T_max  0.99821

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_number            21320
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_full        27.12
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3352
_reflns_number_gt                2782
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.1468P)²+0.3326P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.143
_refine_ls_wR_factor_gt          0.126
_refine_ls_goodness_of_fit_ref   0.636
_refine_ls_restrained_S_all      0.636
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.008
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.032

#----------------------------------------------------------------------------#
#                   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'
F F 0.0171 0.0103 '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 0.34095(12) 0.22563(10) 0.93180(11) 0.0507(3) Uani 1 1 d . . .
N2 N 0.53193(12) -0.14505(11) 0.69910(10) 0.0386(2) Uani 1 1 d . . .
O1 O 0.58884(13) 0.28781(11) 0.91260(12) 0.0597(3) Uani 1 1 d . . .
N1 N 0.57732(12) -0.00530(10) 0.74746(10) 0.0375(2) Uani 1 1 d . . .
F341 F 0.08259(12) -0.72914(11) 0.60171(13) 0.0799(4) Uani 1 1 d . . .
C3 C 0.39355(14) -0.17476(13) 0.73696(12) 0.0361(3) Uani 1 1 d . . .
C32 C 0.38565(15) -0.43805(14) 0.64528(14) 0.0438(3) Uani 1 1 d . . .
H32 H 0.489 -0.424 0.631 0.053 Uiso 1 1 calc R . .
C31 C 0.31133(14) -0.32070(12) 0.70073(12) 0.0362(3) Uani 1 1 d . . .
C51 C 0.47678(16) 0.20143(13) 0.88989(12) 0.0411(3) Uani 1 1 d . . .
C4 C 0.34856(15) -0.05247(13) 0.81004(12) 0.0401(3) Uani 1 1 d . . .
H4 H 0.2572 -0.0446 0.8469 0.048 Uiso 1 1 calc R . .
C36 C 0.15758(17) -0.34500(16) 0.72094(16) 0.0519(4) Uani 1 1 d . . .
H36 H 0.1058 -0.268 0.7578 0.062 Uiso 1 1 calc R . .
C33 C 0.30841(17) -0.57554(15) 0.61090(16) 0.0494(3) Uani 1 1 d . . .
H33 H 0.3585 -0.6533 0.5733 0.059 Uiso 1 1 calc R . .
C12 C 0.69324(18) 0.20551(16) 0.64647(15) 0.0517(3) Uani 1 1 d . . .
H12A H 0.6552 0.2754 0.7071 0.078 Uiso 1 1 calc R . .
H12B H 0.6137 0.1877 0.5662 0.078 Uiso 1 1 calc R . .
H12C H 0.7887 0.2454 0.6229 0.078 Uiso 1 1 calc R . .
C53 C 0.33333(18) 0.36938(14) 1.00236(15) 0.0498(3) Uani 1 1 d . . .
H53A H 0.3349 0.4486 0.9407 0.06 Uiso 1 1 calc R . .
H53B H 0.4242 0.3846 1.0756 0.06 Uiso 1 1 calc R . .
C34 C 0.15754(17) -0.59406(15) 0.63347(15) 0.0510(3) Uani 1 1 d . . .
C11 C 0.72846(15) 0.05932(14) 0.71514(13) 0.0431(3) Uani 1 1 d . . .
C5 C 0.46795(15) 0.05403(13) 0.81611(12) 0.0384(3) Uani 1 1 d . . .
C35 C 0.07934(18) -0.48202(18) 0.68716(19) 0.0610(4) Uani 1 1 d . . .
H35 H -0.0241 -0.4974 0.7007 0.073 Uiso 1 1 calc R . .
C13 C 0.85190(18) 0.08014(18) 0.84551(17) 0.0601(4) Uani 1 1 d . . .
H13A H 0.8137 0.1484 0.9074 0.09 Uiso 1 1 calc R . .
H13B H 0.9496 0.1192 0.8256 0.09 Uiso 1 1 calc R . .
H13C H 0.87 -0.0141 0.8854 0.09 Uiso 1 1 calc R . .
C14 C 0.7886(2) -0.04883(18) 0.6162(2) 0.0641(4) Uani 1 1 d . . .
H14A H 0.8112 -0.1419 0.6573 0.096 Uiso 1 1 calc R . .
H14B H 0.8837 -0.0077 0.5931 0.096 Uiso 1 1 calc R . .
H14C H 0.7088 -0.0649 0.5359 0.096 Uiso 1 1 calc R . .
C54 C 0.1841(2) 0.3712(2) 1.0564(2) 0.0784(6) Uani 1 1 d . . .
H54A H 0.1767 0.4654 1.1034 0.118 Uiso 1 1 calc R . .
H54B H 0.1839 0.2929 1.1176 0.118 Uiso 1 1 calc R . .
H54C H 0.0949 0.3564 0.9832 0.118 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3289(16) . ?
O52 C53 1.4535(15) . ?
N2 C3 1.3372(16) . ?
N2 N1 1.3476(13) . ?
O1 C51 1.2021(16) . ?
N1 C5 1.3676(16) . ?
N1 C11 1.5046(15) . ?
F341 C34 1.3570(14) . ?
C3 C4 1.3951(16) . ?
C3 C31 1.4725(15) . ?
C32 C33 1.3868(17) . ?
C32 C31 1.3917(17) . ?
C31 C36 1.3843(18) . ?
C51 C5 1.4814(16) . ?
C4 C5 1.3766(17) . ?
C36 C35 1.3860(19) . ?
C33 C34 1.362(2) . ?
C12 C11 1.5268(19) . ?
C53 C54 1.481(2) . ?
C34 C35 1.367(2) . ?
C11 C14 1.525(2) . ?
C11 C13 1.5264(19) . ?

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 C53 115.02(10) . . ?
C3 N2 N1 106.52(10) . . ?
N2 N1 C5 110.48(10) . . ?
N2 N1 C11 117.82(10) . . ?
C5 N1 C11 131.66(10) . . ?
N2 C3 C4 110.41(10) . . ?
N2 C3 C31 120.42(10) . . ?
C4 C3 C31 129.17(11) . . ?
C33 C32 C31 121.21(12) . . ?
C36 C31 C32 118.08(11) . . ?
C36 C31 C3 120.83(11) . . ?
C32 C31 C3 121.09(11) . . ?
O1 C51 O52 123.44(11) . . ?
O1 C51 C5 126.67(12) . . ?
O52 C51 C5 109.87(11) . . ?
C5 C4 C3 105.50(11) . . ?
C31 C36 C35 121.20(12) . . ?
C34 C33 C32 118.46(12) . . ?
O52 C53 C54 108.14(12) . . ?
F341 C34 C33 118.55(12) . . ?
F341 C34 C35 118.96(13) . . ?
C33 C34 C35 122.48(12) . . ?
N1 C11 C14 108.66(10) . . ?
N1 C11 C12 109.24(10) . . ?
C14 C11 C12 108.07(13) . . ?
N1 C11 C13 108.82(11) . . ?
C14 C11 C13 109.74(13) . . ?
C12 C11 C13 112.24(11) . . ?
N1 C5 C4 107.08(10) . . ?
N1 C5 C51 127.53(11) . . ?
C4 C5 C51 125.32(11) . . ?
C34 C35 C36 118.56(13) . . ?

# END of CIF
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1829872'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2018-03-14T14:24:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
'ethyl 5-(4-clorophenyl)-1-(tert-butyl)-1H-pyrazole-3-carboxylate'
;
_chemical_name_common            pyrazole
_chemical_formula_moiety         'C16 H19 Cl N2 O2'
_chemical_formula_sum            'C16 H19 Cl N2 O2'
_chemical_formula_weight         306.78
_chemical_melting_point          none
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9637(5)
_cell_length_b                   13.2546(6)
_cell_length_c                   13.9344(6)
_cell_angle_alpha                62.661(2)
_cell_angle_beta                 67.366(2)
_cell_angle_gamma                81.873(3)
_cell_volume                     1658.68(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3781
_cell_measurement_theta_min      2.275
_cell_measurement_theta_max      19.459
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.102
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648

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

_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.976
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.972

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.067
_diffrn_reflns_number            50297
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.731
_diffrn_reflns_theta_max         27.305
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             7388
_reflns_number_gt                3250
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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     
'w=1/[σ²(Fo²)+(0.1173P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.013(3)
_refine_ls_number_reflns         7388
_refine_ls_number_parameters     380
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2439
_refine_ls_wR_factor_gt          0.1897
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.11
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.062

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


#----------------------------------------------------------------------------#
#                   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'
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 0.006 '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_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 0.01058(12) 0.74867(10) 0.44931(9) 0.1029(5) Uani 1 1 d . . . . .
N2A N 0.4162(2) 1.2057(2) -0.2138(2) 0.0615(7) Uani 1 1 d . . . . .
N1A N 0.3462(2) 1.1100(2) -0.1264(2) 0.0548(7) Uani 1 1 d . . . . .
C52A C 0.1092(3) 1.0351(3) 0.1564(3) 0.0613(9) Uani 1 1 d . . . . .
H52A H 0.0693 1.1026 0.1242 0.074 Uiso 1 1 calc R U . . .
C51A C 0.2388(3) 1.0188(3) 0.0940(3) 0.0545(8) Uani 1 1 d . . . . .
C5A C 0.3126(3) 1.1096(3) -0.0203(3) 0.0552(8) Uani 1 1 d . . . . .
C53A C 0.0403(3) 0.9527(3) 0.2646(3) 0.0645(9) Uani 1 1 d . . . . .
H53A H -0.0461 0.9642 0.3051 0.077 Uiso 1 1 calc R U . . .
C56A C 0.2965(3) 0.9193(3) 0.1474(3) 0.0663(9) Uani 1 1 d . . . . .
H56A H 0.3838 0.9081 0.109 0.08 Uiso 1 1 calc R U . . .
C3A C 0.4262(3) 1.2663(3) -0.1626(3) 0.0614(9) Uani 1 1 d . . . . .
C4A C 0.3635(3) 1.2108(3) -0.0434(3) 0.0622(9) Uani 1 1 d . . . . .
H4A H 0.357 1.2366 0.0101 0.075 Uiso 1 1 calc R U . . .
C54A C 0.0987(4) 0.8538(3) 0.3129(3) 0.0666(9) Uani 1 1 d . . . . .
C11A C 0.3186(3) 1.0234(3) -0.1573(3) 0.0604(9) Uani 1 1 d . . . . .
C55A C 0.2279(4) 0.8373(3) 0.2556(3) 0.0736(10) Uani 1 1 d . . . . .
H55A H 0.2682 0.7709 0.29 0.088 Uiso 1 1 calc R U . . .
O32A O 0.5458(4) 1.4126(3) -0.3403(3) 0.1303(14) Uani 1 1 d . . . . .
C31A C 0.4968(4) 1.3776(3) -0.2286(5) 0.0823(12) Uani 1 1 d . . . . .
O2 O 0.5071(3) 1.4315(3) -0.1831(3) 0.1212(13) Uani 1 1 d . . . . .
C12A C 0.1795(3) 0.9732(3) -0.0830(3) 0.0782(11) Uani 1 1 d . . . . .
H12A H 0.1626 0.9179 -0.1033 0.117 Uiso 1 1 calc R U . . .
H12B H 0.1696 0.9374 -0.0028 0.117 Uiso 1 1 calc R U . . .
H12C H 0.1177 1.0325 -0.0958 0.117 Uiso 1 1 calc R U . . .
C14A C 0.3286(5) 1.0829(4) -0.2832(3) 0.1034(16) Uani 1 1 d . . . . .
H14A H 0.3112 1.0285 -0.3044 0.155 Uiso 1 1 calc R U . . .
H14B H 0.265 1.141 -0.2923 0.155 Uiso 1 1 calc R U . . .
H14C H 0.416 1.1168 -0.3323 0.155 Uiso 1 1 calc R U . . .
C13A C 0.4190(4) 0.9329(4) -0.1405(5) 0.1143(18) Uani 1 1 d . . . . .
H13A H 0.4024 0.8768 -0.1601 0.171 Uiso 1 1 calc R U . . .
H13B H 0.5063 0.9669 -0.1899 0.171 Uiso 1 1 calc R U . . .
H13C H 0.4123 0.8974 -0.0611 0.171 Uiso 1 1 calc R U . . .
C33A C 0.5929(9) 1.5359(6) -0.4130(9) 0.222(5) Uani 1 1 d D . . . .
H33A H 0.5499 1.5747 -0.469 0.266 Uiso 1 1 calc R U . . .
H33B H 0.5747 1.5744 -0.3646 0.266 Uiso 1 1 calc R U . . .
C34A C 0.7207(10) 1.5331(8) -0.4655(9) 0.262(6) Uani 1 1 d D . . . .
H34A H 0.7579 1.6094 -0.5139 0.393 Uiso 1 1 calc R U . . .
H34B H 0.7612 1.4939 -0.4087 0.393 Uiso 1 1 calc R U . . .
H34C H 0.7365 1.4941 -0.5124 0.393 Uiso 1 1 calc R U . . .
Cl2 Cl 0.2725(2) 0.07957(12) 0.40964(13) 0.1730(9) Uani 1 1 d . . . . .
N2 N 0.1023(3) 0.6908(2) -0.0323(2) 0.0558(7) Uani 1 1 d . . . . .
N1 N 0.0958(2) 0.5987(2) 0.0678(2) 0.0530(7) Uani 1 1 d . . . . .
O32 O 0.3430(2) 0.7319(2) -0.30474(19) 0.0764(7) Uani 1 1 d . . . . .
O1 O 0.1757(3) 0.8424(2) -0.2695(2) 0.0823(8) Uani 1 1 d . . . . .
C3 C 0.2024(3) 0.6735(3) -0.1141(3) 0.0523(8) Uani 1 1 d . . . . .
C4 C 0.2607(3) 0.5711(3) -0.0683(3) 0.0557(8) Uani 1 1 d . . . . .
H4 H 0.3327 0.5416 -0.1087 0.067 Uiso 1 1 calc R U . . .
C31 C 0.2348(3) 0.7586(3) -0.2357(3) 0.0575(8) Uani 1 1 d . . . . .
C51 C 0.2107(3) 0.4122(3) 0.1364(3) 0.0555(8) Uani 1 1 d . . . . .
C11 C -0.0042(3) 0.5966(3) 0.1781(3) 0.0614(9) Uani 1 1 d . . . . .
C5 C 0.1903(3) 0.5228(3) 0.0485(3) 0.0533(8) Uani 1 1 d . . . . .
C56 C 0.1248(4) 0.3184(3) 0.1866(3) 0.0710(10) Uani 1 1 d . . . . .
H56 H 0.0538 0.3247 0.1636 0.085 Uiso 1 1 calc R U . . .
C52 C 0.3195(4) 0.3981(3) 0.1667(3) 0.0768(11) Uani 1 1 d . . . . .
H52 H 0.3799 0.4589 0.1313 0.092 Uiso 1 1 calc R U . . .
C33 C 0.3832(4) 0.8058(3) -0.4287(3) 0.0838(12) Uani 1 1 d . . . . .
H33C H 0.4779 0.8027 -0.4656 0.101 Uiso 1 1 calc R U . . .
H33D H 0.3634 0.8837 -0.4414 0.101 Uiso 1 1 calc R U . . .
C55 C 0.1448(5) 0.2171(3) 0.2696(4) 0.0909(14) Uani 1 1 d . . . . .
H55 H 0.0859 0.1554 0.3047 0.109 Uiso 1 1 calc R U . . .
C53 C 0.3404(5) 0.2961(4) 0.2483(4) 0.0988(14) Uani 1 1 d . . . . .
H53 H 0.4148 0.2878 0.2675 0.119 Uiso 1 1 calc R U . . .
C54 C 0.2524(6) 0.2068(4) 0.3011(4) 0.0942(15) Uani 1 1 d . . . . .
C34 C 0.3141(5) 0.7709(4) -0.4807(4) 0.1133(17) Uani 1 1 d . . . . .
H34D H 0.3418 0.8205 -0.5624 0.17 Uiso 1 1 calc R U . . .
H34E H 0.3347 0.6942 -0.4691 0.17 Uiso 1 1 calc R U . . .
H34F H 0.2204 0.775 -0.4449 0.17 Uiso 1 1 calc R U . . .
C12 C -0.1196(6) 0.5218(6) 0.2170(6) 0.169(3) Uani 1 1 d . . . . .
H12D H -0.157 0.55 0.1578 0.254 Uiso 1 1 calc R U . . .
H12E H -0.0914 0.446 0.2313 0.254 Uiso 1 1 calc R U . . .
H12F H -0.185 0.5212 0.287 0.254 Uiso 1 1 calc R U . . .
C14 C -0.0520(6) 0.7145(4) 0.1573(4) 0.138(2) Uani 1 1 d . . . . .
H14D H 0.0211 0.7643 0.132 0.207 Uiso 1 1 calc R U . . .
H14E H -0.0901 0.742 0.0987 0.207 Uiso 1 1 calc R U . . .
H14F H -0.1175 0.7123 0.228 0.207 Uiso 1 1 calc R U . . .
C13 C 0.0582(6) 0.5571(6) 0.2665(4) 0.151(3) Uani 1 1 d . . . . .
H13D H 0.1321 0.6075 0.2382 0.227 Uiso 1 1 calc R U . . .
H13E H -0.0054 0.5569 0.337 0.227 Uiso 1 1 calc R U . . .
H13F H 0.0882 0.4816 0.2813 0.227 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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
Cl1 C54A 1.739(4) . ?
N2A C3A 1.333(4) . ?
N2A N1A 1.348(3) . ?
N1A C5A 1.376(4) . ?
N1A C11A 1.498(4) . ?
C52A C53A 1.371(4) . ?
C52A C51A 1.399(4) . ?
C51A C56A 1.385(5) . ?
C51A C5A 1.471(4) . ?
C5A C4A 1.375(4) . ?
C53A C54A 1.366(5) . ?
C56A C55A 1.369(5) . ?
C3A C4A 1.383(5) . ?
C3A C31A 1.467(5) . ?
C54A C55A 1.376(5) . ?
C11A C13A 1.507(5) . ?
C11A C12A 1.510(4) . ?
C11A C14A 1.523(5) . ?
O32A C31A 1.300(6) . ?
O32A C33A 1.510(7) . ?
C31A O2 1.191(5) . ?
C33A C34A 1.312(10) . ?
Cl2 C54 1.729(4) . ?
N2 C3 1.328(4) . ?
N2 N1 1.351(3) . ?
N1 C5 1.378(4) . ?
N1 C11 1.495(4) . ?
O32 C31 1.332(4) . ?
O32 C33 1.456(4) . ?
O1 C31 1.194(4) . ?
C3 C4 1.390(4) . ?
C3 C31 1.471(4) . ?
C4 C5 1.368(4) . ?
C51 C52 1.375(5) . ?
C51 C56 1.395(5) . ?
C51 C5 1.473(4) . ?
C11 C12 1.487(6) . ?
C11 C13 1.488(6) . ?
C11 C14 1.506(5) . ?
C56 C55 1.369(5) . ?
C52 C53 1.369(5) . ?
C33 C34 1.465(6) . ?
C55 C54 1.380(6) . ?
C53 C54 1.360(7) . ?

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
C3A N2A N1A 105.0(3) . . ?
N2A N1A C5A 111.6(2) . . ?
N2A N1A C11A 117.6(2) . . ?
C5A N1A C11A 130.8(3) . . ?
C53A C52A C51A 120.7(3) . . ?
C56A C51A C52A 117.7(3) . . ?
C56A C51A C5A 122.1(3) . . ?
C52A C51A C5A 120.0(3) . . ?
C4A C5A N1A 105.8(3) . . ?
C4A C5A C51A 127.3(3) . . ?
N1A C5A C51A 126.9(3) . . ?
C54A C53A C52A 120.0(3) . . ?
C55A C56A C51A 121.5(3) . . ?
N2A C3A C4A 111.7(3) . . ?
N2A C3A C31A 122.2(4) . . ?
C4A C3A C31A 126.1(4) . . ?
C5A C4A C3A 105.9(3) . . ?
C53A C54A C55A 120.6(3) . . ?
C53A C54A Cl1 119.9(3) . . ?
C55A C54A Cl1 119.5(3) . . ?
N1A C11A C13A 108.6(3) . . ?
N1A C11A C12A 110.0(3) . . ?
C13A C11A C12A 111.3(3) . . ?
N1A C11A C14A 108.4(3) . . ?
C13A C11A C14A 110.7(3) . . ?
C12A C11A C14A 107.8(3) . . ?
C56A C55A C54A 119.4(3) . . ?
C31A O32A C33A 116.2(5) . . ?
O2 C31A O32A 123.1(4) . . ?
O2 C31A C3A 122.4(5) . . ?
O32A C31A C3A 114.5(4) . . ?
C34A C33A O32A 104.7(8) . . ?
C3 N2 N1 105.0(2) . . ?
N2 N1 C5 111.4(2) . . ?
N2 N1 C11 117.6(2) . . ?
C5 N1 C11 131.0(3) . . ?
C31 O32 C33 116.9(3) . . ?
N2 C3 C4 111.8(3) . . ?
N2 C3 C31 118.8(3) . . ?
C4 C3 C31 129.3(3) . . ?
C5 C4 C3 105.7(3) . . ?
O1 C31 O32 123.6(3) . . ?
O1 C31 C3 125.6(3) . . ?
O32 C31 C3 110.8(3) . . ?
C52 C51 C56 118.5(3) . . ?
C52 C51 C5 120.1(3) . . ?
C56 C51 C5 121.4(3) . . ?
C12 C11 C13 112.0(5) . . ?
C12 C11 N1 109.0(3) . . ?
C13 C11 N1 109.3(3) . . ?
C12 C11 C14 108.1(5) . . ?
C13 C11 C14 108.6(4) . . ?
N1 C11 C14 109.8(3) . . ?
C4 C5 N1 106.1(3) . . ?
C4 C5 C51 127.3(3) . . ?
N1 C5 C51 126.7(3) . . ?
C55 C56 C51 120.2(4) . . ?
C53 C52 C51 121.0(4) . . ?
O32 C33 C34 110.7(3) . . ?
C56 C55 C54 119.9(4) . . ?
C54 C53 C52 120.0(4) . . ?
C53 C54 C55 120.3(4) . . ?
C53 C54 Cl2 120.7(5) . . ?
C55 C54 Cl2 119.1(5) . . ?


# END of CIF
####################################################################### 
# 
# 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_mo_mmv0142_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 1833322'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_date             2016-09-13T12:55:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
        'ethyl 3-(phenyl)-1-(t-butyl)1H-pyrazole-5-carboxylate'
;
_chemical_name_common            pirazol-1,5-Ph
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.900(5)
_cell_length_b                   8.307(4)
_cell_length_c                   19.352(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.44(2)
_cell_angle_gamma                90
_cell_volume                     1430.2(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      3.065
_cell_measurement_theta_max      30.044

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_special_details           
;
        SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal
;

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

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.9760
_exptl_absorpt_correction_T_max  0.9867

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_number            23991
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         30.12
_diffrn_reflns_theta_full        30.12
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             4174
_reflns_number_gt                3422
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   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 > 2σ(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)+(0.0493P)²+0.5397P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4174
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   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 0.27594(8) 0.36137(9) 0.53404(4) 0.01646(16) Uani 1 1 d . . .
O1 O 0.21274(9) 0.62014(9) 0.54898(4) 0.01972(17) Uani 1 1 d . . .
N2 N 0.64832(10) 0.60624(10) 0.65484(4) 0.01437(18) Uani 1 1 d . . .
N1 N 0.50856(10) 0.64281(10) 0.63145(4) 0.01356(17) Uani 1 1 d . . .
C34 C 1.09782(12) 0.23482(13) 0.68325(6) 0.0187(2) Uani 1 1 d . . .
H34 H 1.1887 0.1859 0.6953 0.022 Uiso 1 1 calc R . .
C33 C 1.07830(12) 0.39817(13) 0.69386(6) 0.0179(2) Uani 1 1 d . . .
H33 H 1.1566 0.4592 0.7129 0.021 Uiso 1 1 calc R . .
C32 C 0.94253(12) 0.47144(12) 0.67632(5) 0.0159(2) Uani 1 1 d . . .
H32 H 0.9308 0.5815 0.6832 0.019 Uiso 1 1 calc R . .
C31 C 0.82349(11) 0.38139(12) 0.64837(5) 0.01312(19) Uani 1 1 d . . .
C3 C 0.67772(11) 0.45723(12) 0.63218(5) 0.01342(19) Uani 1 1 d . . .
C4 C 0.55456(11) 0.39660(12) 0.59428(5) 0.0147(2) Uani 1 1 d . . .
H4 H 0.5462 0.2959 0.5735 0.018 Uiso 1 1 calc R . .
C5 C 0.44788(11) 0.51711(12) 0.59408(5) 0.0137(2) Uani 1 1 d . . .
C51 C 0.29997(11) 0.51076(12) 0.55766(5) 0.0145(2) Uani 1 1 d . . .
C53 C 0.12887(11) 0.33697(13) 0.50110(5) 0.0158(2) Uani 1 1 d . . .
H53A H 0.1112 0.417 0.4653 0.019 Uiso 1 1 calc R . .
H53B H 0.0507 0.3469 0.5349 0.019 Uiso 1 1 calc R . .
C54 C 0.12697(13) 0.17149(14) 0.47034(7) 0.0235(2) Uani 1 1 d . . .
H54A H 0.031 0.152 0.4482 0.035 Uiso 1 1 calc R . .
H54B H 0.1443 0.0933 0.5062 0.035 Uiso 1 1 calc R . .
H54C H 0.2045 0.1631 0.4369 0.035 Uiso 1 1 calc R . .
C11 C 0.44669(12) 0.80548(12) 0.64912(5) 0.0153(2) Uani 1 1 d . . .
C12 C 0.42998(13) 0.90435(13) 0.58280(6) 0.0206(2) Uani 1 1 d . . .
H12A H 0.3604 0.8519 0.5515 0.031 Uiso 1 1 calc R . .
H12B H 0.526 0.9136 0.5616 0.031 Uiso 1 1 calc R . .
H12C H 0.3931 1.0097 0.5936 0.031 Uiso 1 1 calc R . .
C13 C 0.29728(12) 0.78555(13) 0.68519(6) 0.0193(2) Uani 1 1 d . . .
H13A H 0.2263 0.7334 0.6545 0.029 Uiso 1 1 calc R . .
H13B H 0.2595 0.8895 0.6977 0.029 Uiso 1 1 calc R . .
H13C H 0.3121 0.7213 0.726 0.029 Uiso 1 1 calc R . .
C14 C 0.55695(13) 0.88890(13) 0.69896(6) 0.0212(2) Uani 1 1 d . . .
H14A H 0.6518 0.9025 0.6771 0.032 Uiso 1 1 calc R . .
H14B H 0.5707 0.8244 0.7398 0.032 Uiso 1 1 calc R . .
H14C H 0.5178 0.9923 0.7114 0.032 Uiso 1 1 calc R . .
C35 C 0.98110(13) 0.14472(13) 0.65455(6) 0.0194(2) Uani 1 1 d . . .
H35 H 0.9939 0.0351 0.647 0.023 Uiso 1 1 calc R . .
C36 C 0.84518(12) 0.21756(12) 0.63701(5) 0.0164(2) Uani 1 1 d . . .
H36 H 0.7677 0.1563 0.6174 0.02 Uiso 1 1 calc R . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3378(14) . ?
O52 C53 1.4556(14) . ?
O1 C51 1.2041(13) . ?
N2 C3 1.3411(14) . ?
N2 N1 1.3475(13) . ?
N1 C5 1.3731(14) . ?
N1 C11 1.5018(14) . ?
C34 C33 1.3840(17) . ?
C34 C35 1.3852(17) . ?
C34 H34 0.93 . ?
C33 C32 1.3875(16) . ?
C33 H33 0.93 . ?
C32 C31 1.3950(15) . ?
C32 H32 0.93 . ?
C31 C36 1.3928(16) . ?
C31 C3 1.4689(15) . ?
C3 C4 1.3975(15) . ?
C4 C5 1.3795(15) . ?
C4 H4 0.93 . ?
C5 C51 1.4786(16) . ?
C53 C54 1.4979(17) . ?
C53 H53A 0.97 . ?
C53 H53B 0.97 . ?
C54 H54A 0.96 . ?
C54 H54B 0.96 . ?
C54 H54C 0.96 . ?
C11 C14 1.5251(16) . ?
C11 C13 1.5262(16) . ?
C11 C12 1.5279(16) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C35 C36 1.3870(16) . ?
C35 H35 0.93 . ?
C36 H36 0.93 . ?

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 C53 114.40(8) . . ?
C3 N2 N1 106.52(8) . . ?
N2 N1 C5 110.67(8) . . ?
N2 N1 C11 117.84(8) . . ?
C5 N1 C11 131.49(9) . . ?
C33 C34 C35 119.58(10) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C33 C32 120.37(10) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C32 C31 120.52(10) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C36 C31 C32 118.57(10) . . ?
C36 C31 C3 120.71(9) . . ?
C32 C31 C3 120.72(10) . . ?
N2 C3 C4 110.32(9) . . ?
N2 C3 C31 120.31(9) . . ?
C4 C3 C31 129.37(10) . . ?
C5 C4 C3 105.70(9) . . ?
C5 C4 H4 127.1 . . ?
C3 C4 H4 127.1 . . ?
N1 C5 C4 106.79(9) . . ?
N1 C5 C51 127.73(9) . . ?
C4 C5 C51 125.44(9) . . ?
O1 C51 O52 123.74(10) . . ?
O1 C51 C5 127.07(10) . . ?
O52 C51 C5 109.19(9) . . ?
O52 C53 C54 107.63(9) . . ?
O52 C53 H53A 110.2 . . ?
C54 C53 H53A 110.2 . . ?
O52 C53 H53B 110.2 . . ?
C54 C53 H53B 110.2 . . ?
H53A C53 H53B 108.5 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
N1 C11 C14 108.61(9) . . ?
N1 C11 C13 109.58(8) . . ?
C14 C11 C13 108.32(10) . . ?
N1 C11 C12 108.72(9) . . ?
C14 C11 C12 109.54(9) . . ?
C13 C11 C12 112.02(9) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C34 C35 C36 120.20(11) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.74(10) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 N1 C5 0.29(11) . . . . ?
C3 N2 N1 C11 -179.61(8) . . . . ?
C35 C34 C33 C32 0.39(16) . . . . ?
C34 C33 C32 C31 0.60(16) . . . . ?
C33 C32 C31 C36 -1.50(15) . . . . ?
C33 C32 C31 C3 177.65(9) . . . . ?
N1 N2 C3 C4 -0.58(11) . . . . ?
N1 N2 C3 C31 179.38(8) . . . . ?
C36 C31 C3 N2 167.52(9) . . . . ?
C32 C31 C3 N2 -11.62(14) . . . . ?
C36 C31 C3 C4 -12.53(16) . . . . ?
C32 C31 C3 C4 168.33(10) . . . . ?
N2 C3 C4 C5 0.65(11) . . . . ?
C31 C3 C4 C5 -179.31(10) . . . . ?
N2 N1 C5 C4 0.11(11) . . . . ?
C11 N1 C5 C4 179.99(10) . . . . ?
N2 N1 C5 C51 -177.58(9) . . . . ?
C11 N1 C5 C51 2.30(17) . . . . ?
C3 C4 C5 N1 -0.44(11) . . . . ?
C3 C4 C5 C51 177.31(9) . . . . ?
C53 O52 C51 O1 -4.61(14) . . . . ?
C53 O52 C51 C5 176.05(8) . . . . ?
N1 C5 C51 O1 7.57(17) . . . . ?
C4 C5 C51 O1 -169.71(11) . . . . ?
N1 C5 C51 O52 -173.12(9) . . . . ?
C4 C5 C51 O52 9.60(14) . . . . ?
C51 O52 C53 C54 173.33(9) . . . . ?
N2 N1 C11 C14 -6.44(12) . . . . ?
C5 N1 C11 C14 173.68(10) . . . . ?
N2 N1 C11 C13 -124.59(10) . . . . ?
C5 N1 C11 C13 55.54(14) . . . . ?
N2 N1 C11 C12 112.68(10) . . . . ?
C5 N1 C11 C12 -67.19(13) . . . . ?
C33 C34 C35 C36 -0.44(17) . . . . ?
C34 C35 C36 C31 -0.49(16) . . . . ?
C32 C31 C36 C35 1.45(15) . . . . ?
C3 C31 C36 C35 -177.70(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12A O1 0.96 2.33 3.1107(18) 138 .
C13 H13A O1 0.96 2.25 3.0500(19) 140.4 .

# END of CIF
