# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_c2
_database_code_depnum_ccdc_archive 'CCDC 1576917'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2017-09-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
4-Methyl-2-(5-[4-dimethylaminophenyl]-lH-pyrazole-3-yl)phenol
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_chemical_melting_point          ?
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 0.0000 0.0000 '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 0.0060 '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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   16.236(3)
_cell_length_b                   7.7124(15)
_cell_length_c                   25.238(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.08(3)
_cell_angle_gamma                90
_cell_volume                     3065.4(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13913
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.03
_cell_measurement_theta_min      6.16
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            23729
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.078
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3670
_reflns_number_total             6863
_reflns_special_details          
;
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         6863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0853P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1550
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C25(H25A,H25B,H25C)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C19 C -0.22796(13) 0.3892(3) 0.19323(7) 0.0605(5) Uani 1 1 d . . . . .
C14 C -0.03721(12) 0.6689(2) 0.04449(7) 0.0504(4) Uani 1 1 d . . . . .
C11 C 0.14353(12) 0.6463(2) 0.07546(7) 0.0509(5) Uani 1 1 d . . . . .
C12 C 0.10042(13) 0.7347(3) 0.02829(7) 0.0543(5) Uani 1 1 d . . . . .
C10 C 0.23564(12) 0.6345(2) 0.08914(7) 0.0518(5) Uani 1 1 d . . . . .
C15 C 0.00613(13) 0.5807(3) 0.09179(7) 0.0560(5) Uani 1 1 d . . . . .
N2 N 0.28211(12) 0.5684(3) 0.13642(7) 0.0708(5) Uani 1 1 d . . . . .
C16 C 0.09296(13) 0.5711(3) 0.10627(7) 0.0558(5) Uani 1 1 d . . . . .
C13 C 0.01362(13) 0.7471(3) 0.01331(7) 0.0541(5) Uani 1 1 d . . . . .
C9 C 0.29398(12) 0.6868(3) 0.06107(7) 0.0555(5) Uani 1 1 d . . . . .
N1 N 0.36699(12) 0.5745(3) 0.14057(7) 0.0735(5) Uani 1 1 d . . . . .
C6 C 0.45793(12) 0.6844(3) 0.08441(7) 0.0572(5) Uani 1 1 d . . . . .
C8 C 0.37430(13) 0.6479(3) 0.09415(7) 0.0566(5) Uani 1 1 d . . . . .
C1 C 0.53031(14) 0.6971(3) 0.12729(8) 0.0700(6) Uani 1 1 d . . . . .
O1 O 0.52908(13) 0.6614(3) 0.18001(6) 0.1013(6) Uani 1 1 d . . . . .
C5 C 0.46647(14) 0.7159(3) 0.03180(8) 0.0649(6) Uani 1 1 d . . . . .
C4 C 0.54214(14) 0.7641(3) 0.02029(9) 0.0689(6) Uani 1 1 d . . . . .
C2 C 0.60598(17) 0.7507(4) 0.11670(11) 0.0843(7) Uani 1 1 d . . . . .
C3 C 0.61114(17) 0.7847(3) 0.06424(11) 0.0787(7) Uani 1 1 d . . . . .
C7 C 0.54881(17) 0.7945(4) -0.03735(10) 0.0959(8) Uani 1 1 d . . . . .
H7A H 0.598575 0.862171 -0.036956 0.144 Uiso 1 1 calc GR . . . .
H7B H 0.499368 0.855593 -0.057188 0.144 Uiso 1 1 calc GR . . . .
H7C H 0.552738 0.685091 -0.054713 0.144 Uiso 1 1 calc GR . . . .
N4 N -0.03550(10) 0.0414(2) 0.11714(6) 0.0558(4) Uani 1 1 d . . . . .
N5 N 0.04960(10) 0.0259(2) 0.12572(6) 0.0547(4) Uani 1 1 d . . . . .
N6 N 0.45338(10) 0.1598(2) 0.22528(6) 0.0606(4) Uani 1 1 d . . . . .
C28 C 0.09303(11) 0.1306(2) 0.16622(6) 0.0458(4) Uani 1 1 d . . . . .
C29 C 0.18548(11) 0.1369(2) 0.18163(6) 0.0451(4) Uani 1 1 d . . . . .
C32 C 0.36617(11) 0.1541(2) 0.21131(6) 0.0499(4) Uani 1 1 d . . . . .
C31 C 0.32185(12) 0.0605(3) 0.16556(7) 0.0546(5) Uani 1 1 d . . . . .
C30 C 0.23474(12) 0.0535(3) 0.15161(7) 0.0524(5) Uani 1 1 d . . . . .
C33 C 0.31634(12) 0.2367(3) 0.24194(7) 0.0550(5) Uani 1 1 d . . . . .
C26 C -0.04693(11) 0.1603(2) 0.15316(6) 0.0474(4) Uani 1 1 d . . . . .
O2 O -0.19833(9) 0.0397(2) 0.07386(5) 0.0750(5) Uani 1 1 d . . . . .
H2 H -0.149054 0.006497 0.078872 0.113 Uiso 1 1 calc GR . . . .
C27 C 0.03143(11) 0.2192(3) 0.18468(7) 0.0479(4) Uani 1 1 d . . . . .
C24 C -0.14795(13) 0.3298(3) 0.19240(7) 0.0553(5) Uani 1 1 d . . . . .
C22 C -0.20463(12) 0.1536(3) 0.11406(7) 0.0546(5) Uani 1 1 d . . . . .
C23 C -0.13343(11) 0.2135(2) 0.15352(6) 0.0475(4) Uani 1 1 d . . . . .
C34 C 0.22939(12) 0.2289(3) 0.22761(7) 0.0524(5) Uani 1 1 d . . . . .
C35 C 0.49710(14) 0.2733(4) 0.26893(8) 0.0797(7) Uani 1 1 d . . . . .
H35A H 0.486050 0.391931 0.257932 0.120 Uiso 1 1 calc GR . . . .
H35B H 0.557063 0.251660 0.276622 0.120 Uiso 1 1 calc GR . . . .
H35C H 0.477111 0.251564 0.301112 0.120 Uiso 1 1 calc GR . . . .
C20 C -0.29601(15) 0.3294(3) 0.15293(9) 0.0657(6) Uani 1 1 d . . . . .
C21 C -0.28453(14) 0.2125(3) 0.11443(8) 0.0644(6) Uani 1 1 d . . . . .
C36 C 0.49948(14) 0.1230(4) 0.18468(9) 0.0883(8) Uani 1 1 d . . . . .
H36A H 0.487611 0.006552 0.171628 0.132 Uiso 1 1 calc GR . . . .
H36B H 0.559254 0.135317 0.200490 0.132 Uiso 1 1 calc GR . . . .
H36C H 0.482388 0.202640 0.154776 0.132 Uiso 1 1 calc GR . . . .
C25 C -0.24106(15) 0.5134(4) 0.23660(9) 0.0888(8) Uani 1 1 d . . . . .
H25A H -0.206583 0.478427 0.271481 0.133 Uiso 1 1 calc GR . . . .
H25B H -0.299751 0.512674 0.237691 0.133 Uiso 1 1 calc GR . . . .
H25C H -0.225193 0.628235 0.228223 0.133 Uiso 1 1 calc GR . . . .
N3 N -0.12363(11) 0.6787(2) 0.02979(6) 0.0616(4) Uani 1 1 d . . . . .
C17 C -0.16748(18) 0.7675(4) -0.01964(9) 0.0670(6) Uani 1 1 d . . . . .
C18 C -0.17454(18) 0.5916(4) 0.06116(12) 0.0756(7) Uani 1 1 d . . . . .
H27 H 0.0377(11) 0.303(3) 0.2129(7) 0.061(5) Uiso 1 1 d . . . . .
H34 H 0.1972(11) 0.287(3) 0.2520(7) 0.059(5) Uiso 1 1 d . . . . .
H12 H 0.1347(12) 0.792(3) 0.0049(7) 0.059(5) Uiso 1 1 d . . . . .
H9 H 0.2806(12) 0.742(3) 0.0260(8) 0.065(6) Uiso 1 1 d . . . . .
H33 H 0.3417(13) 0.301(3) 0.2748(8) 0.073(6) Uiso 1 1 d . . . . .
H24 H -0.0985(12) 0.366(3) 0.2199(7) 0.065(6) Uiso 1 1 d . . . . .
H16 H 0.1197(12) 0.506(3) 0.1385(7) 0.059(5) Uiso 1 1 d . . . . .
H13 H -0.0159(14) 0.811(3) -0.0210(8) 0.084(7) Uiso 1 1 d . . . . .
H15 H -0.0239(12) 0.522(3) 0.1153(7) 0.069(6) Uiso 1 1 d . . . . .
H5A H 0.4162(14) 0.703(3) 0.0021(8) 0.079(7) Uiso 1 1 d . . . . .
H21 H -0.3338(14) 0.167(3) 0.0888(8) 0.078(7) Uiso 1 1 d . . . . .
H18A H -0.1657(15) 0.640(3) 0.0973(10) 0.094(8) Uiso 1 1 d . . . . .
H18B H -0.1636(16) 0.469(4) 0.0652(9) 0.105(9) Uiso 1 1 d . . . . .
H30 H 0.2057(12) -0.010(3) 0.1179(7) 0.063(5) Uiso 1 1 d . . . . .
H31 H 0.3522(12) 0.000(3) 0.1427(7) 0.069(6) Uiso 1 1 d . . . . .
H17A H -0.1531(15) 0.719(3) -0.0515(9) 0.090(7) Uiso 1 1 d . . . . .
H2A H 0.2645(14) 0.523(3) 0.1638(9) 0.085(7) Uiso 1 1 d . . . . .
H20 H -0.3500(14) 0.365(3) 0.1548(8) 0.078(7) Uiso 1 1 d . . . . .
H5 H 0.0721(14) -0.052(3) 0.1055(9) 0.085(7) Uiso 1 1 d . . . . .
H2B H 0.6578(18) 0.761(4) 0.1472(10) 0.108(8) Uiso 1 1 d . . . . .
H3 H 0.6662(17) 0.827(3) 0.0587(8) 0.096(8) Uiso 1 1 d . . . . .
H17B H -0.230(2) 0.761(4) -0.0255(10) 0.130(11) Uiso 1 1 d . . . . .
H17C H -0.1497(16) 0.891(4) -0.0178(9) 0.104(9) Uiso 1 1 d . . . . .
H18C H -0.2354(19) 0.594(4) 0.0414(10) 0.113(9) Uiso 1 1 d . . . . .
H1 H 0.472(2) 0.625(4) 0.1805(11) 0.134(12) Uiso 1 1 d . . . . .


_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
C19 C24 1.382(3) . ?
C19 C20 1.386(3) . ?
C19 C25 1.508(3) . ?
C14 C15 1.405(3) . ?
C14 C13 1.407(2) . ?
C14 N3 1.363(2) . ?
C11 C12 1.402(3) . ?
C11 C10 1.454(3) . ?
C11 C16 1.388(3) . ?
C12 C13 1.371(3) . ?
C10 N2 1.347(2) . ?
C10 C9 1.374(3) . ?
C15 C16 1.370(3) . ?
N2 N1 1.357(2) . ?
C9 C8 1.399(3) . ?
N1 C8 1.332(2) . ?
C6 C8 1.465(3) . ?
C6 C1 1.394(3) . ?
C6 C5 1.389(3) . ?
C1 O1 1.364(3) . ?
C1 C2 1.383(3) . ?
C5 C4 1.381(3) . ?
C4 C3 1.380(3) . ?
C4 C7 1.503(3) . ?
C2 C3 1.372(3) . ?
N4 N5 1.351(2) . ?
N4 C26 1.336(2) . ?
N5 C28 1.357(2) . ?
N6 C32 1.374(2) . ?
N6 C35 1.450(3) . ?
N6 C36 1.437(2) . ?
C28 C29 1.457(2) . ?
C28 C27 1.383(2) . ?
C29 C30 1.386(2) . ?
C29 C34 1.399(2) . ?
C32 C31 1.403(2) . ?
C32 C33 1.401(2) . ?
C31 C30 1.373(3) . ?
C33 C34 1.371(3) . ?
C26 C27 1.402(2) . ?
C26 C23 1.465(2) . ?
O2 C22 1.364(2) . ?
C24 C23 1.392(3) . ?
C22 C23 1.408(2) . ?
C22 C21 1.377(3) . ?
C20 C21 1.371(3) . ?
N3 C17 1.449(3) . ?
N3 C18 1.442(3) . ?

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
C24 C19 C20 117.57(19) . . ?
C24 C19 C25 121.36(18) . . ?
C20 C19 C25 121.07(19) . . ?
C15 C14 C13 116.24(18) . . ?
N3 C14 C15 121.83(17) . . ?
N3 C14 C13 121.94(17) . . ?
C12 C11 C10 120.29(16) . . ?
C16 C11 C12 115.96(18) . . ?
C16 C11 C10 123.74(17) . . ?
C13 C12 C11 122.37(17) . . ?
N2 C10 C11 123.81(17) . . ?
N2 C10 C9 105.07(18) . . ?
C9 C10 C11 131.10(17) . . ?
C16 C15 C14 121.54(18) . . ?
C10 N2 N1 113.24(17) . . ?
C15 C16 C11 122.60(18) . . ?
C12 C13 C14 121.28(17) . . ?
C10 C9 C8 106.79(17) . . ?
C8 N1 N2 104.65(17) . . ?
C1 C6 C8 121.60(18) . . ?
C5 C6 C8 120.40(18) . . ?
C5 C6 C1 117.93(19) . . ?
C9 C8 C6 128.78(18) . . ?
N1 C8 C9 110.25(18) . . ?
N1 C8 C6 120.91(18) . . ?
O1 C1 C6 122.3(2) . . ?
O1 C1 C2 118.3(2) . . ?
C2 C1 C6 119.5(2) . . ?
C4 C5 C6 123.3(2) . . ?
C5 C4 C7 121.5(2) . . ?
C3 C4 C5 116.9(2) . . ?
C3 C4 C7 121.6(2) . . ?
C3 C2 C1 120.6(2) . . ?
C2 C3 C4 121.7(2) . . ?
C26 N4 N5 104.94(15) . . ?
N4 N5 C28 113.07(16) . . ?
C32 N6 C35 119.84(16) . . ?
C32 N6 C36 119.59(15) . . ?
C36 N6 C35 114.66(18) . . ?
N5 C28 C29 122.25(15) . . ?
N5 C28 C27 105.18(16) . . ?
C27 C28 C29 132.55(16) . . ?
C30 C29 C28 122.17(15) . . ?
C30 C29 C34 116.33(17) . . ?
C34 C29 C28 121.51(16) . . ?
N6 C32 C31 121.19(16) . . ?
N6 C32 C33 122.76(16) . . ?
C33 C32 C31 116.03(17) . . ?
C30 C31 C32 121.41(17) . . ?
C31 C30 C29 122.48(16) . . ?
C34 C33 C32 122.05(17) . . ?
N4 C26 C27 110.58(16) . . ?
N4 C26 C23 119.25(16) . . ?
C27 C26 C23 130.14(17) . . ?
C28 C27 C26 106.23(16) . . ?
C19 C24 C23 123.05(18) . . ?
O2 C22 C23 122.70(18) . . ?
O2 C22 C21 117.32(17) . . ?
C21 C22 C23 119.97(19) . . ?
C24 C23 C26 120.80(16) . . ?
C24 C23 C22 117.37(17) . . ?
C22 C23 C26 121.81(16) . . ?
C33 C34 C29 121.69(17) . . ?
C21 C20 C19 121.2(2) . . ?
C20 C21 C22 120.9(2) . . ?
C14 N3 C17 121.19(18) . . ?
C14 N3 C18 120.96(18) . . ?
C18 N3 C17 117.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform / petroleum ether'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 1576929'
_audit_update_record             
;
2017-09-28 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2017-09-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
4-Methyl-2-(5-[4-dimethylaminophenyl]-lH-pyrazole-3-yl)phenol
_chemical_formula_moiety         'C18 H19 N3 O'
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_chemical_melting_point          ?
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 0.0000 0.0000 '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 0.0060 '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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.841(3)
_cell_length_b                   10.286(2)
_cell_length_c                   12.663(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.023(7)
_cell_angle_gamma                90
_cell_volume                     1561.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2061
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.189
_cell_measurement_theta_min      2.610
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flaky
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9820
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.106
_diffrn_reflns_theta_max         25.106
_diffrn_reflns_theta_min         1.699
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1958
_reflns_number_total             2771
_reflns_special_details          
;
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+0.1360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N2 N 0.99835(14) 0.02273(16) 0.30209(14) 0.0568(5) Uani 1 1 d . . . . .
O1 O 0.81806(12) 0.02986(14) 0.49313(12) 0.0659(4) Uani 1 1 d . . . . .
N1 N 0.92095(13) 0.03419(15) 0.35182(13) 0.0561(4) Uani 1 1 d . . . . .
C8 C 0.84358(14) 0.11378(16) 0.28455(15) 0.0445(4) Uani 1 1 d . . . . .
C14 C 1.19442(15) 0.11699(16) 0.01992(16) 0.0482(5) Uani 1 1 d . . . . .
C16 C 1.14223(17) 0.02098(19) 0.16794(18) 0.0575(5) Uani 1 1 d . . . . .
C10 C 0.97365(14) 0.09382(16) 0.20686(15) 0.0452(4) Uani 1 1 d . . . . .
C1 C 0.73699(15) 0.10274(16) 0.41601(15) 0.0470(4) Uani 1 1 d . . . . .
C2 C 0.64416(17) 0.13365(19) 0.44234(18) 0.0553(5) Uani 1 1 d . . . . .
C11 C 1.04838(14) 0.09919(16) 0.14277(15) 0.0446(4) Uani 1 1 d . . . . .
C6 C 0.74545(14) 0.14537(15) 0.31430(15) 0.0435(4) Uani 1 1 d . . . . .
C12 C 1.02883(17) 0.18586(18) 0.05368(17) 0.0517(5) Uani 1 1 d . . . . .
C9 C 0.87352(15) 0.15399(17) 0.19316(16) 0.0457(4) Uani 1 1 d . . . . .
C5 C 0.65805(16) 0.21959(17) 0.24246(17) 0.0506(5) Uani 1 1 d . . . . .
N3 N 1.26505(13) 0.12552(16) -0.04030(15) 0.0624(5) Uani 1 1 d . . . . .
C13 C 1.09926(16) 0.19485(18) -0.00634(18) 0.0538(5) Uani 1 1 d . . . . .
C3 C 0.55985(17) 0.20782(19) 0.36916(18) 0.0584(5) Uani 1 1 d . . . . .
C15 C 1.21394(17) 0.02945(19) 0.10946(19) 0.0580(5) Uani 1 1 d . . . . .
C4 C 0.56440(16) 0.25249(18) 0.26722(18) 0.0563(5) Uani 1 1 d . . . . .
C17 C 1.3624(2) 0.0441(3) -0.0127(3) 0.0706(7) Uani 1 1 d . . . . .
C18 C 1.2397(3) 0.2104(3) -0.1362(3) 0.0754(7) Uani 1 1 d . . . . .
C7 C 0.47259(19) 0.3351(2) 0.1883(2) 0.0833(7) Uani 1 1 d . . . . .
H7A H 0.485211 0.347344 0.118702 0.125 Uiso 1 1 calc GR . . . .
H7B H 0.471884 0.418112 0.222775 0.125 Uiso 1 1 calc GR . . . .
H7C H 0.402130 0.292684 0.173164 0.125 Uiso 1 1 calc GR . . . .
H5 H 0.6628(14) 0.2506(15) 0.1718(15) 0.045(5) Uiso 1 1 d . . . . .
H9 H 0.8343(15) 0.2117(16) 0.1327(16) 0.051(5) Uiso 1 1 d . . . . .
H17A H 1.3403(19) -0.046(2) -0.018(2) 0.087(8) Uiso 1 1 d . . . . .
H13 H 1.0832(16) 0.2579(18) -0.0689(17) 0.062(6) Uiso 1 1 d . . . . .
H3 H 0.4947(17) 0.2271(16) 0.3902(16) 0.058(5) Uiso 1 1 d . . . . .
H12 H 0.9624(18) 0.2414(18) 0.0324(17) 0.065(6) Uiso 1 1 d . . . . .
H2A H 0.6392(16) 0.1002(19) 0.5145(17) 0.069(6) Uiso 1 1 d . . . . .
H15 H 1.2756(18) -0.0227(19) 0.1288(18) 0.072(6) Uiso 1 1 d . . . . .
H16 H 1.1589(17) -0.043(2) 0.2297(19) 0.076(7) Uiso 1 1 d . . . . .
H18A H 1.294(2) 0.198(2) -0.175(2) 0.114(9) Uiso 1 1 d . . . . .
H17B H 1.405(2) 0.057(2) -0.065(2) 0.107(9) Uiso 1 1 d . . . . .
H18B H 1.168(3) 0.192(3) -0.188(3) 0.127(12) Uiso 1 1 d . . . . .
H2 H 1.061(2) -0.018(2) 0.344(2) 0.086(8) Uiso 1 1 d . . . . .
H18C H 1.244(2) 0.300(3) -0.111(2) 0.124(11) Uiso 1 1 d . . . . .
H17C H 1.414(2) 0.063(3) 0.065(3) 0.121(11) Uiso 1 1 d . . . . .
H1 H 0.868(2) 0.009(2) 0.456(2) 0.091(8) Uiso 1 1 d . . . . .


_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
N2 N1 1.359(2) . ?
N2 C10 1.347(2) . ?
O1 C1 1.367(2) . ?
N1 C8 1.332(2) . ?
C8 C6 1.475(2) . ?
C8 C9 1.406(2) . ?
C14 N3 1.381(2) . ?
C14 C13 1.398(3) . ?
C14 C15 1.398(3) . ?
C16 C11 1.388(3) . ?
C16 C15 1.376(3) . ?
C10 C11 1.463(2) . ?
C10 C9 1.381(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.401(2) . ?
C2 C3 1.376(3) . ?
C11 C12 1.388(3) . ?
C6 C5 1.392(3) . ?
C12 C13 1.377(3) . ?
C5 C4 1.389(3) . ?
N3 C17 1.440(3) . ?
N3 C18 1.435(3) . ?
C3 C4 1.391(3) . ?
C4 C7 1.505(3) . ?

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
C10 N2 N1 113.03(16) . . ?
C8 N1 N2 104.99(15) . . ?
N1 C8 C6 118.78(16) . . ?
N1 C8 C9 110.22(15) . . ?
C9 C8 C6 131.01(16) . . ?
N3 C14 C13 121.56(17) . . ?
N3 C14 C15 121.76(16) . . ?
C13 C14 C15 116.68(17) . . ?
C15 C16 C11 122.23(19) . . ?
N2 C10 C11 121.76(16) . . ?
N2 C10 C9 105.38(16) . . ?
C9 C10 C11 132.83(17) . . ?
O1 C1 C2 117.03(17) . . ?
O1 C1 C6 122.54(16) . . ?
C2 C1 C6 120.44(18) . . ?
C3 C2 C1 120.16(19) . . ?
C16 C11 C10 122.62(17) . . ?
C16 C11 C12 116.61(17) . . ?
C12 C11 C10 120.77(16) . . ?
C1 C6 C8 121.38(16) . . ?
C5 C6 C8 121.09(16) . . ?
C5 C6 C1 117.53(16) . . ?
C13 C12 C11 121.89(18) . . ?
C10 C9 C8 106.38(16) . . ?
C4 C5 C6 123.13(19) . . ?
C14 N3 C17 120.94(18) . . ?
C14 N3 C18 120.73(17) . . ?
C18 N3 C17 118.24(19) . . ?
C12 C13 C14 121.42(18) . . ?
C2 C3 C4 121.55(19) . . ?
C16 C15 C14 121.15(18) . . ?
C5 C4 C3 117.19(19) . . ?
C5 C4 C7 121.54(19) . . ?
C3 C4 C7 121.25(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  chloroform / methol'
_exptl_crystal_preparation       Luminescent
