# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_ch6173i
_audit_block_doi                 10.5517/cc1kb917
_database_code_depnum_ccdc_archive 'CCDC 1439858'
_audit_update_record             
;
2015-12-06 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;

_chemical_name_systematic        
; 
 2-(3,4,5-trimethoxyphenyl)-2-(3,5-dimethylpyrazol-4-yl)ethanol 
;
_chemical_name_common            ?
_chemical_melting_point_gt       394
_chemical_melting_point_lt       395
_chemical_formula_moiety         'C16 H21 N O5'
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_preparation       'petroleum ether : ethyl acetate, 1:2'
_exptl_crystal_density_diffrn    1.294

_cell_length_a                   7.7056(4)
_cell_length_b                   10.9002(4)
_cell_length_c                   11.0359(4)
_cell_angle_alpha                65.488(3)
_cell_angle_beta                 72.568(3)
_cell_angle_gamma                72.725(3)
_cell_volume                     788.58(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)

_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'

_diffrn_ambient_temperature      295(2)

_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1207
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
O1 O 0.38817(17) 0.32821(12) 0.52890(10) 0.0643(3) Uani 1 1 d . . . . .
N2 N 0.3001(2) 0.46083(15) 0.45779(12) 0.0652(4) Uani 1 1 d . . . . .
C3 C 0.2190(2) 0.52068(16) 0.54659(14) 0.0570(4) Uani 1 1 d . . . . .
C4 C 0.2494(2) 0.43177(14) 0.67867(13) 0.0490(3) Uani 1 1 d . . . . .
C5 C 0.3559(2) 0.31345(15) 0.66086(13) 0.0523(4) Uani 1 1 d . . . . .
C31 C 0.1118(3) 0.66387(19) 0.50271(19) 0.0798(5) Uani 1 1 d . . . . .
H31A H 0.1067 0.6941 0.4086 0.120 Uiso 1 1 calc R U . . .
H31B H 0.1711 0.7230 0.5145 0.120 Uiso 1 1 calc R U . . .
H31C H -0.0119 0.6672 0.5567 0.120 Uiso 1 1 calc R U . . .
C41 C 0.1839(2) 0.47093(13) 0.80102(14) 0.0524(4) Uani 1 1 d . . . . .
H41 H 0.0677 0.5387 0.7893 0.063 Uiso 1 1 calc R U . . .
C42 C 0.1378(2) 0.34906(13) 0.93589(13) 0.0483(3) Uani 1 1 d . . . . .
C43 C 0.0063(2) 0.28077(14) 0.94320(13) 0.0503(3) Uani 1 1 d . . . . .
H43 H -0.0518 0.3097 0.8705 0.060 Uiso 1 1 calc R U . . .
C44 C -0.0379(2) 0.16885(14) 1.05988(13) 0.0482(3) Uani 1 1 d . . . . .
C45 C 0.0474(2) 0.12615(13) 1.16911(13) 0.0487(3) Uani 1 1 d . . . . .
C46 C 0.1770(2) 0.19656(14) 1.16151(13) 0.0489(3) Uani 1 1 d . . . . .
C47 C 0.2216(2) 0.30750(15) 1.04519(13) 0.0507(3) Uani 1 1 d . . . . .
H47 H 0.3080 0.3542 1.0406 0.061 Uiso 1 1 calc R U . . .
C48 C 0.3220(3) 0.54383(15) 0.80947(15) 0.0618(4) Uani 1 1 d . . . . .
H48A H 0.3313 0.6270 0.7296 0.074 Uiso 1 1 calc R U . . .
H48B H 0.2728 0.5709 0.8885 0.074 Uiso 1 1 calc R U . . .
O48 O 0.50139(18) 0.46257(12) 0.81822(11) 0.0642(3) Uani 1 1 d . . . . .
H48 H 0.570(3) 0.486(2) 0.734(2) 0.081(6) Uiso 1 1 d . . . . .
O49 O -0.16565(16) 0.09602(11) 1.07656(10) 0.0589(3) Uani 1 1 d . . . . .
C50 C -0.2527(3) 0.13501(17) 0.96515(17) 0.0645(4) Uani 1 1 d . . . . .
H50A H -0.3199 0.2283 0.9455 0.097 Uiso 1 1 calc R U . . .
H50B H -0.3368 0.0754 0.9883 0.097 Uiso 1 1 calc R U . . .
H50C H -0.1598 0.1276 0.8867 0.097 Uiso 1 1 calc R U . . .
O51 O 0.01489(16) 0.00971(10) 1.28086(10) 0.0597(3) Uani 1 1 d . . . . .
C52 C -0.1503(3) 0.0251(2) 1.37588(17) 0.0761(5) Uani 1 1 d . . . . .
H52A H -0.1593 -0.0614 1.4493 0.114 Uiso 1 1 calc R U . . .
H52B H -0.2542 0.0547 1.3326 0.114 Uiso 1 1 calc R U . . .
H52C H -0.1504 0.0924 1.4108 0.114 Uiso 1 1 calc R U . . .
O53 O 0.24992(17) 0.14922(12) 1.27427(10) 0.0644(3) Uani 1 1 d . . . . .
C54 C 0.3752(3) 0.2207(2) 1.27362(17) 0.0742(5) Uani 1 1 d . . . . .
H54A H 0.4864 0.2094 1.2072 0.111 Uiso 1 1 calc R U . . .
H54B H 0.4052 0.1847 1.3619 0.111 Uiso 1 1 calc R U . . .
H54C H 0.3196 0.3166 1.2512 0.111 Uiso 1 1 calc R U . . .
C51 C 0.4363(3) 0.17827(17) 0.75154(17) 0.0707(5) Uani 1 1 d . . . . .
H51A H 0.3559 0.1151 0.7778 0.106 Uiso 1 1 calc R U . . .
H51B H 0.4496 0.1871 0.8312 0.106 Uiso 1 1 calc R U . . .
H51C H 0.5558 0.1444 0.7049 0.106 Uiso 1 1 calc R U . . .



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 C5 1.3495(16) . ?
O1 N2 1.4004(19) . ?
N2 C3 1.303(2) . ?
C3 C4 1.420(2) . ?
C3 C31 1.483(3) . ?
C4 C5 1.364(2) . ?
C4 C41 1.4839(19) . ?
C5 C51 1.470(2) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C41 C48 1.548(2) . ?
C41 C42 1.5586(17) . ?
C41 H41 0.9800 . ?
C42 C47 1.385(2) . ?
C42 C43 1.391(2) . ?
C43 C44 1.3940(19) . ?
C43 H43 0.9300 . ?
C44 O49 1.3663(17) . ?
C44 C45 1.389(2) . ?
C45 O51 1.3781(15) . ?
C45 C46 1.395(2) . ?
C46 O53 1.3580(18) . ?
C46 C47 1.3865(19) . ?
C47 H47 0.9300 . ?
C48 O48 1.409(2) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
O48 H48 0.89(2) . ?
O49 C50 1.4257(19) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
O51 C52 1.403(2) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
O53 C54 1.406(2) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 N2 108.28(11) . . ?
C3 N2 O1 106.60(11) . . ?
N2 C3 C4 111.28(14) . . ?
N2 C3 C31 119.85(15) . . ?
C4 C3 C31 128.87(15) . . ?
C5 C4 C3 104.14(12) . . ?
C5 C4 C41 131.03(13) . . ?
C3 C4 C41 124.74(13) . . ?
O1 C5 C4 109.69(13) . . ?
O1 C5 C51 115.63(12) . . ?
C4 C5 C51 134.67(13) . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C4 C41 C48 110.94(11) . . ?
C4 C41 C42 113.62(11) . . ?
C48 C41 C42 111.76(13) . . ?
C4 C41 H41 106.7 . . ?
C48 C41 H41 106.7 . . ?
C42 C41 H41 106.7 . . ?
C47 C42 C43 120.04(12) . . ?
C47 C42 C41 123.02(13) . . ?
C43 C42 C41 116.95(13) . . ?
C42 C43 C44 119.75(13) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
O49 C44 C45 115.81(11) . . ?
O49 C44 C43 123.90(13) . . ?
C45 C44 C43 120.28(12) . . ?
O51 C45 C44 120.76(12) . . ?
O51 C45 C46 119.58(13) . . ?
C44 C45 C46 119.51(12) . . ?
O53 C46 C47 124.57(13) . . ?
O53 C46 C45 115.25(12) . . ?
C47 C46 C45 120.17(13) . . ?
C42 C47 C46 120.24(13) . . ?
C42 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
O48 C48 C41 114.07(11) . . ?
O48 C48 H48A 108.7 . . ?
C41 C48 H48A 108.7 . . ?
O48 C48 H48B 108.7 . . ?
C41 C48 H48B 108.7 . . ?
H48A C48 H48B 107.6 . . ?
C48 O48 H48 106.8(14) . . ?
C44 O49 C50 117.28(11) . . ?
O49 C50 H50A 109.5 . . ?
O49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
O49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C45 O51 C52 116.14(12) . . ?
O51 C52 H52A 109.5 . . ?
O51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C46 O53 C54 117.30(12) . . ?
O53 C54 H54A 109.5 . . ?
O53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 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
C5 O1 N2 C3 -0.11(16) . . . . ?
O1 N2 C3 C4 0.06(18) . . . . ?
O1 N2 C3 C31 -179.70(16) . . . . ?
N2 C3 C4 C5 0.01(19) . . . . ?
C31 C3 C4 C5 179.74(17) . . . . ?
N2 C3 C4 C41 176.81(13) . . . . ?
C31 C3 C4 C41 -3.5(3) . . . . ?
N2 O1 C5 C4 0.12(17) . . . . ?
N2 O1 C5 C51 179.00(14) . . . . ?
C3 C4 C5 O1 -0.08(17) . . . . ?
C41 C4 C5 O1 -176.60(13) . . . . ?
C3 C4 C5 C51 -178.65(18) . . . . ?
C41 C4 C5 C51 4.8(3) . . . . ?
C5 C4 C41 C48 91.64(18) . . . . ?
C3 C4 C41 C48 -84.25(18) . . . . ?
C5 C4 C41 C42 -35.3(2) . . . . ?
C3 C4 C41 C42 148.84(15) . . . . ?
C4 C41 C42 C47 122.54(15) . . . . ?
C48 C41 C42 C47 -3.95(18) . . . . ?
C4 C41 C42 C43 -57.20(17) . . . . ?
C48 C41 C42 C43 176.31(12) . . . . ?
C47 C42 C43 C44 -1.2(2) . . . . ?
C41 C42 C43 C44 178.53(12) . . . . ?
C42 C43 C44 O49 179.66(12) . . . . ?
C42 C43 C44 C45 0.6(2) . . . . ?
O49 C44 C45 O51 5.60(19) . . . . ?
C43 C44 C45 O51 -175.24(12) . . . . ?
O49 C44 C45 C46 -178.81(11) . . . . ?
C43 C44 C45 C46 0.4(2) . . . . ?
O51 C45 C46 O53 -5.74(19) . . . . ?
C44 C45 C46 O53 178.61(12) . . . . ?
O51 C45 C46 C47 175.01(12) . . . . ?
C44 C45 C46 C47 -0.6(2) . . . . ?
C43 C42 C47 C46 0.9(2) . . . . ?
C41 C42 C47 C46 -178.79(12) . . . . ?
O53 C46 C47 C42 -179.19(12) . . . . ?
C45 C46 C47 C42 0.0(2) . . . . ?
C4 C41 C48 O48 -60.52(16) . . . . ?
C42 C41 C48 O48 67.41(14) . . . . ?
C45 C44 O49 C50 -178.53(13) . . . . ?
C43 C44 O49 C50 2.3(2) . . . . ?
C44 C45 O51 C52 -80.31(18) . . . . ?
C46 C45 O51 C52 104.10(17) . . . . ?
C47 C46 O53 C54 1.9(2) . . . . ?
C45 C46 O53 C54 -177.31(13) . . . . ?

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
O48 H48 N2 0.89(2) 1.97(2) 2.8586(17) 174(2) 2_666

############################################################################

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

_cell_measurement_reflns_used    14414
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      72.52

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.798
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.040
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.4209
_exptl_absorpt_correction_T_max  0.9609
_exptl_special_details           ?

_diffrn_radiation_wavelength     1.54186
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      '3497 frames, detector distance = 60 mm'
_diffrn_measurement_device_type  'Stoe STADI VARI'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2690
_diffrn_reflns_av_R_equivalents  0.0000 #0.0513
_diffrn_reflns_av_sigmaI/netI    0.0945
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.497
_diffrn_reflns_theta_max         67.689
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             2690
_reflns_number_gt                2160
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'X--AREA  (STOE & CIE, 2012)'
_computing_cell_refinement       'X--AREA  (STOE & CIE, 2012)'
_computing_data_reduction        'X--AREA  (STOE & CIE, 2012)'
_computing_structure_solution    'SHELXS97 (Sheldrick,  2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick,  2008)'
_computing_molecular_graphics    'Ortep--3 (Farrugia,   1997)'
_computing_publication_material  'WinGX    (Farrugia,   1999)'

_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     
'w=1/[σ²(Fo²)+(0.0887P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2690
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_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.
;


_refine_diff_density_max         0.189
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

