# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_C21H23NO2
_database_code_depnum_ccdc_archive 'CCDC 1545451'
_audit_update_record             
;
2017-04-23 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-1-(4-(azepan-1-yl)phenyl)-3-hydroxy-3-phenylprop-2-en-1-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   15.43(2)
_cell_length_b                   10.791(17)
_cell_length_c                   10.129(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.94(3)
_cell_angle_gamma                90
_cell_volume                     1650(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    3624
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      32.10

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5906
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27021
_diffrn_reflns_av_unetI/netI     0.1023
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.575
_diffrn_reflns_theta_max         33.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             5395
_reflns_number_gt                2957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1239P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         5395
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.2092
_refine_ls_wR_factor_gt          0.1383
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.977
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.64933(9) 0.94322(11) 0.15374(18) 0.0321(4) Uani 1 1 d . . . . .
O2 O 0.78730(9) 0.86719(11) 0.10682(19) 0.0329(4) Uani 1 1 d . . . . .
N1 N 0.35610(8) 0.85850(12) 0.49553(19) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.64897(10) 0.85520(13) 0.2400(2) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.71977(10) 0.76946(14) 0.2641(2) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.78798(10) 0.78046(13) 0.1936(2) 0.0235(4) Uani 1 1 d . . . . .
C4 C 0.86501(10) 0.69457(13) 0.2135(2) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.92594(11) 0.70773(15) 0.1307(3) 0.0288(5) Uani 1 1 d . . . . .
C6 C 0.99800(11) 0.62788(17) 0.1440(3) 0.0335(5) Uani 1 1 d . . . . .
C7 C 1.01015(11) 0.53571(16) 0.2387(3) 0.0314(5) Uani 1 1 d . . . . .
C8 C 0.94989(11) 0.52172(16) 0.3215(3) 0.0295(5) Uani 1 1 d . . . . .
C9 C 0.87760(11) 0.60134(15) 0.3093(2) 0.0254(4) Uani 1 1 d . . . . .
C10 C 0.57452(10) 0.85202(13) 0.3070(2) 0.0210(4) Uani 1 1 d . . . . .
C11 C 0.55957(10) 0.75555(14) 0.3911(2) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.48804(10) 0.75587(14) 0.4525(2) 0.0218(4) Uani 1 1 d . . . . .
C13 C 0.42709(9) 0.85599(13) 0.4347(2) 0.0193(4) Uani 1 1 d . . . . .
C14 C 0.44303(10) 0.95425(13) 0.3513(2) 0.0201(4) Uani 1 1 d . . . . .
C15 C 0.51426(10) 0.95142(13) 0.2888(2) 0.0213(4) Uani 1 1 d . . . . .
C16 C 0.34947(11) 0.77090(15) 0.6018(2) 0.0224(4) Uani 1 1 d . . . . .
C17 C 0.29587(11) 0.65592(15) 0.5489(3) 0.0258(4) Uani 1 1 d . . . . .
C18 C 0.19579(12) 0.67600(15) 0.5156(3) 0.0269(4) Uani 1 1 d . . . . .
C19 C 0.16522(11) 0.78563(16) 0.4246(3) 0.0270(4) Uani 1 1 d . . . . .
C20 C 0.19743(10) 0.91114(15) 0.4851(3) 0.0239(4) Uani 1 1 d . . . . .
C21 C 0.28624(10) 0.95111(14) 0.4563(2) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.716(3) 0.930(4) 0.118(5) 0.099(13) Uiso 1 1 d . . . . .
H2 H 0.7216(13) 0.705(2) 0.329(3) 0.022(5) Uiso 1 1 d . . . . .
H5 H 0.9165(16) 0.767(2) 0.059(3) 0.034(6) Uiso 1 1 d . . . . .
H6 H 1.0393(17) 0.641(2) 0.084(3) 0.040(7) Uiso 1 1 d . . . . .
H7 H 1.060(2) 0.480(3) 0.236(4) 0.060(9) Uiso 1 1 d . . . . .
H8 H 0.9570(17) 0.458(3) 0.393(3) 0.042(7) Uiso 1 1 d . . . . .
H9 H 0.8375(15) 0.585(2) 0.375(3) 0.031(6) Uiso 1 1 d . . . . .
H11 H 0.5987(14) 0.683(2) 0.406(3) 0.025(5) Uiso 1 1 d . . . . .
H12 H 0.4802(15) 0.689(2) 0.514(3) 0.031(6) Uiso 1 1 d . . . . .
H14 H 0.4052(15) 1.028(2) 0.346(3) 0.028(6) Uiso 1 1 d . . . . .
H15 H 0.5242(14) 1.018(2) 0.233(3) 0.027(6) Uiso 1 1 d . . . . .
H16A H 0.3230(15) 0.811(2) 0.671(3) 0.030(6) Uiso 1 1 d . . . . .
H16B H 0.4101(15) 0.748(2) 0.640(3) 0.029(6) Uiso 1 1 d . . . . .
H17A H 0.3103(15) 0.595(2) 0.617(3) 0.030(6) Uiso 1 1 d . . . . .
H17B H 0.3201(15) 0.623(2) 0.467(3) 0.032(6) Uiso 1 1 d . . . . .
H18A H 0.1755(14) 0.686(2) 0.605(3) 0.025(5) Uiso 1 1 d . . . . .
H18B H 0.1653(14) 0.601(2) 0.471(3) 0.026(5) Uiso 1 1 d . . . . .
H19A H 0.1000(17) 0.788(2) 0.399(3) 0.041(7) Uiso 1 1 d . . . . .
H19B H 0.1831(15) 0.775(2) 0.338(3) 0.030(6) Uiso 1 1 d . . . . .
H20A H 0.2009(15) 0.909(2) 0.581(3) 0.025(6) Uiso 1 1 d . . . . .
H20B H 0.1543(14) 0.976(2) 0.447(3) 0.025(5) Uiso 1 1 d . . . . .
H21A H 0.3066(14) 1.031(2) 0.509(3) 0.025(5) Uiso 1 1 d . . . . .
H21B H 0.2787(15) 0.962(2) 0.349(3) 0.028(6) 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
O1 C1 1.291(3) . ?
O1 H1 1.17(4) . ?
O2 C3 1.282(3) . ?
O2 H1 1.31(4) . ?
N1 C13 1.364(3) . ?
N1 C16 1.452(3) . ?
N1 C21 1.463(3) . ?
C1 C2 1.414(3) . ?
C1 C10 1.451(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.95(2) . ?
C3 C4 1.488(3) . ?
C4 C5 1.391(3) . ?
C4 C9 1.383(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.96(3) . ?
C6 C7 1.368(4) . ?
C6 H6 0.98(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.99(3) . ?
C8 C9 1.393(3) . ?
C8 H8 0.99(3) . ?
C9 H9 1.01(2) . ?
C10 C11 1.394(3) . ?
C10 C15 1.407(3) . ?
C11 C12 1.375(3) . ?
C11 H11 0.98(2) . ?
C12 C13 1.419(3) . ?
C12 H12 0.97(3) . ?
C13 C14 1.409(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.98(2) . ?
C15 H15 0.94(2) . ?
C16 C17 1.526(3) . ?
C16 H16A 0.98(3) . ?
C16 H16B 0.97(2) . ?
C17 C18 1.527(3) . ?
C17 H17A 0.95(3) . ?
C17 H17B 1.04(3) . ?
C18 C19 1.513(3) . ?
C18 H18A 1.02(3) . ?
C18 H18B 0.99(2) . ?
C19 C20 1.527(3) . ?
C19 H19A 0.99(3) . ?
C19 H19B 0.98(3) . ?
C20 C21 1.522(3) . ?
C20 H20A 0.96(3) . ?
C20 H20B 0.98(2) . ?
C21 H21A 1.03(2) . ?
C21 H21B 1.07(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
C1 O1 H1 104(2) . . ?
C3 O2 H1 102(2) . . ?
C13 N1 C16 120.55(14) . . ?
C13 N1 C21 120.43(17) . . ?
C16 N1 C21 119.01(15) . . ?
O1 C1 C2 119.13(17) . . ?
O1 C1 C10 116.65(15) . . ?
C2 C1 C10 124.21(18) . . ?
C3 C2 C1 119.63(19) . . ?
C3 C2 H2 119.8(12) . . ?
C1 C2 H2 120.6(12) . . ?
O2 C3 C2 120.87(15) . . ?
O2 C3 C4 116.15(16) . . ?
C2 C3 C4 122.98(19) . . ?
C5 C4 C9 118.88(16) . . ?
C5 C4 C3 118.38(19) . . ?
C9 C4 C3 122.74(17) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 120.6(14) . . ?
C6 C5 H5 118.9(14) . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 121.9(16) . . ?
C5 C6 H6 117.5(16) . . ?
C6 C7 C8 119.54(17) . . ?
C6 C7 H7 115(2) . . ?
C8 C7 H7 125(2) . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 122.3(15) . . ?
C9 C8 H8 117.3(15) . . ?
C4 C9 C8 120.30(19) . . ?
C4 C9 H9 124.5(14) . . ?
C8 C9 H9 115.2(14) . . ?
C11 C10 C15 117.45(17) . . ?
C11 C10 C1 123.41(14) . . ?
C15 C10 C1 119.13(17) . . ?
C12 C11 C10 121.64(15) . . ?
C12 C11 H11 117.1(13) . . ?
C10 C11 H11 121.2(13) . . ?
C11 C12 C13 121.15(17) . . ?
C11 C12 H12 120.1(13) . . ?
C13 C12 H12 118.6(13) . . ?
N1 C13 C14 120.80(14) . . ?
N1 C13 C12 122.07(17) . . ?
C14 C13 C12 117.13(17) . . ?
C15 C14 C13 120.92(14) . . ?
C15 C14 H14 121.0(14) . . ?
C13 C14 H14 117.9(14) . . ?
C14 C15 C10 121.70(17) . . ?
C14 C15 H15 120.1(13) . . ?
C10 C15 H15 118.2(13) . . ?
N1 C16 C17 112.7(2) . . ?
N1 C16 H16A 110.5(15) . . ?
C17 C16 H16A 109.3(14) . . ?
N1 C16 H16B 104.7(15) . . ?
C17 C16 H16B 110.0(14) . . ?
H16A C16 H16B 110(2) . . ?
C18 C17 C16 114.37(15) . . ?
C18 C17 H17A 109.5(13) . . ?
C16 C17 H17A 106.6(16) . . ?
C18 C17 H17B 112.8(14) . . ?
C16 C17 H17B 107.3(13) . . ?
H17A C17 H17B 106(2) . . ?
C19 C18 C17 114.79(15) . . ?
C19 C18 H18A 109.8(13) . . ?
C17 C18 H18A 107.5(13) . . ?
C19 C18 H18B 107.7(15) . . ?
C17 C18 H18B 110.3(13) . . ?
H18A C18 H18B 106.5(19) . . ?
C18 C19 C20 114.5(2) . . ?
C18 C19 H19A 110.8(16) . . ?
C20 C19 H19A 108.0(15) . . ?
C18 C19 H19B 109.8(14) . . ?
C20 C19 H19B 109.8(14) . . ?
H19A C19 H19B 103(2) . . ?
C21 C20 C19 113.94(16) . . ?
C21 C20 H20A 109.6(13) . . ?
C19 C20 H20A 109.3(14) . . ?
C21 C20 H20B 106.7(13) . . ?
C19 C20 H20B 109.4(14) . . ?
H20A C20 H20B 108(2) . . ?
N1 C21 C20 113.36(17) . . ?
N1 C21 H21A 107.7(13) . . ?
C20 C21 H21A 109.1(12) . . ?
N1 C21 H21B 105.7(12) . . ?
C20 C21 H21B 108.1(12) . . ?
H21A C21 H21B 113.0(19) . . ?

_refine_diff_density_max         0.733
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.113



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/hexane'
_exptl_crystal_preparation       ', Luminescent'
