# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_I
_audit_block_doi                 10.5517/cc14mz6y
_database_code_depnum_ccdc_archive 'CCDC 1061880'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5CC03515E 2015
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            CDME
_chemical_formula_moiety         'C22 H17 N O4'
_chemical_formula_sum            'C22 H17 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         359.36

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3977(5)
_cell_length_b                   11.6656(7)
_cell_length_c                   20.3981(13)
_cell_angle_alpha                76.247(3)
_cell_angle_beta                 83.564(3)
_cell_angle_gamma                88.301(4)
_cell_volume                     1699.07(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9585
_cell_measurement_theta_min      2.2429
_cell_measurement_theta_max      74.4907
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2012). TWINABS v2012/1. Bruker AXS Inc. Madison, WI 53719,
US.
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS HB'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            6574
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_full        74.50
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25

_refine_special_details          'Refined as a 2-component twin.'

_reflns_number_total             6574
_reflns_number_gt                5471
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1090
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_number_reflns         6574
_refine_ls_number_parameters     492
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.7032P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v4.2.0 (Bruker AXS Inc., 2013)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'XT v2013/6 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 v2014.3-0 (Bruker AXS Inc., 2013)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1_1 0.5383(3) 0.92600(17) 0.23515(9) 0.0196(4) Uani d . . . 1 . .
O O1_1 0.7407(2) 0.46450(15) 0.15974(9) 0.0273(4) Uani d . . . 1 . .
O O2_1 0.7632(2) 0.64605(15) 0.09084(8) 0.0235(4) Uani d . . . 1 . .
O O3_1 0.3468(3) 0.57763(15) 0.43046(8) 0.0274(4) Uani d . . . 1 . .
O O4_1 0.4198(2) 0.41971(15) 0.38805(8) 0.0231(4) Uani d . . . 1 . .
C C1_1 0.5877(3) 0.9862(2) 0.28224(11) 0.0206(5) Uani d . . . 1 . .
C C2_1 0.6310(3) 0.9430(2) 0.34832(12) 0.0232(5) Uani d . . . 1 . .
H H2_1 0.6329 0.8606 0.3681 0.028 Uiso calc U . R 1 . .
C C3_1 0.6712(4) 1.0242(2) 0.38424(13) 0.0276(5) Uani d . . . 1 . .
H H3_1 0.6995 0.997 0.4297 0.033 Uiso calc U . R 1 . .
C C4_1 0.6709(3) 1.1453(2) 0.35501(13) 0.0278(6) Uani d . . . 1 . .
H H4_1 0.6973 1.199 0.3811 0.033 Uiso calc U . R 1 . .
C C5_1 0.6332(3) 1.1883(2) 0.28914(13) 0.0263(5) Uani d . . . 1 . .
H H5_1 0.6353 1.2707 0.2694 0.032 Uiso calc U . R 1 . .
C C6_1 0.5915(3) 1.1079(2) 0.25176(12) 0.0218(5) Uani d . . . 1 . .
C C7_1 0.5459(3) 1.1216(2) 0.18346(12) 0.0208(5) Uani d . . . 1 . .
C C8_1 0.5293(3) 1.2202(2) 0.12979(13) 0.0258(5) Uani d . . . 1 . .
H H8_1 0.5566 1.297 0.1341 0.031 Uiso calc U . R 1 . .
C C9_1 0.4731(3) 1.2039(2) 0.07080(13) 0.0283(6) Uani d . . . 1 . .
H H9_1 0.4604 1.2704 0.0342 0.034 Uiso calc U . R 1 . .
C C10_1 0.4342(3) 1.0913(2) 0.06359(12) 0.0268(5) Uani d . . . 1 . .
H H10_1 0.3932 1.0829 0.0225 0.032 Uiso calc U . R 1 . .
C C11_1 0.4542(3) 0.9915(2) 0.11526(11) 0.0218(5) Uani d . . . 1 . .
H H11_1 0.4295 0.9149 0.1101 0.026 Uiso calc U . R 1 . .
C C12_1 0.5123(3) 1.0084(2) 0.17529(11) 0.0205(5) Uani d . . . 1 . .
C C13_1 0.5409(3) 0.8012(2) 0.24432(11) 0.0185(5) Uani d . . . 1 . .
C C14_1 0.6280(3) 0.7507(2) 0.19377(11) 0.0182(5) Uani d . . . 1 . .
H H14_1 0.6845 0.7993 0.1529 0.022 Uiso calc U . R 1 . .
C C15_1 0.6317(3) 0.6286(2) 0.20348(11) 0.0185(5) Uani d . . . 1 . .
C C16_1 0.5576(3) 0.5568(2) 0.26483(11) 0.0194(5) Uani d . . . 1 . .
H H16_1 0.5635 0.4734 0.2719 0.023 Uiso calc U . R 1 . .
C C17_1 0.4754(3) 0.6079(2) 0.31520(11) 0.0200(5) Uani d . . . 1 . .
C C18_1 0.4613(3) 0.7299(2) 0.30426(11) 0.0191(5) Uani d . . . 1 . .
H H18_1 0.3971 0.7643 0.3379 0.023 Uiso calc U . R 1 . .
C C19_1 0.7174(3) 0.5699(2) 0.15040(12) 0.0203(5) Uani d . . . 1 . .
C C20_1 0.8470(4) 0.5925(2) 0.03789(12) 0.0285(6) Uani d . . . 1 . .
H H20A_1 0.8661 0.6527 -0.0048 0.043 Uiso calc U . R 1 . .
H H20B_1 0.7673 0.5306 0.0323 0.043 Uiso calc U . R 1 . .
H H20C_1 0.9642 0.5578 0.0503 0.043 Uiso calc U . R 1 . .
C C21_1 0.4053(3) 0.5360(2) 0.38369(11) 0.0200(5) Uani d . . . 1 . .
C C22_1 0.3637(4) 0.3460(2) 0.45460(11) 0.0266(5) Uani d . . . 1 . .
H H22A_1 0.2365 0.363 0.4684 0.04 Uiso calc U . R 1 . .
H H22B_1 0.4407 0.3622 0.4874 0.04 Uiso calc U . R 1 . .
H H22C_1 0.376 0.2628 0.4531 0.04 Uiso calc U . R 1 . .
N N1_2 0.1036(3) 0.41904(17) 0.25666(9) 0.0196(4) Uani d . . . 1 . .
O O1_2 -0.0252(3) -0.03654(15) 0.17855(9) 0.0267(4) Uani d . . . 1 . .
O O2_2 -0.0051(2) 0.14506(15) 0.11003(8) 0.0244(4) Uani d . . . 1 . .
O O3_2 0.2114(3) 0.06607(16) 0.44963(8) 0.0300(4) Uani d . . . 1 . .
O O4_2 0.1766(3) -0.08937(15) 0.40494(8) 0.0267(4) Uani d . . . 1 . .
C C1_2 0.0244(3) 0.4797(2) 0.30420(11) 0.0185(5) Uani d . . . 1 . .
C C2_2 -0.0584(3) 0.4362(2) 0.37040(11) 0.0220(5) Uani d . . . 1 . .
H H2_2 -0.0692 0.3538 0.3896 0.026 Uiso calc U . R 1 . .
C C3_2 -0.1241(4) 0.5175(2) 0.40697(12) 0.0251(5) Uani d . . . 1 . .
H H3_2 -0.1801 0.4904 0.4521 0.03 Uiso calc U . R 1 . .
C C4_2 -0.1091(3) 0.6391(2) 0.37842(12) 0.0246(5) Uani d . . . 1 . .
H H4_2 -0.1528 0.6931 0.4049 0.03 Uiso calc U . R 1 . .
C C5_2 -0.0326(3) 0.6818(2) 0.31291(12) 0.0225(5) Uani d . . . 1 . .
H H5_2 -0.0264 0.7644 0.2936 0.027 Uiso calc U . R 1 . .
C C6_2 0.0359(3) 0.6020(2) 0.27515(11) 0.0188(5) Uani d . . . 1 . .
C C7_2 0.1239(3) 0.6160(2) 0.20679(11) 0.0178(4) Uani d . . . 1 . .
C C8_2 0.1729(3) 0.7142(2) 0.15460(11) 0.0204(5) Uani d . . . 1 . .
H H8_2 0.1437 0.7915 0.16 0.024 Uiso calc U . R 1 . .
C C9_2 0.2648(3) 0.6976(2) 0.09463(12) 0.0234(5) Uani d . . . 1 . .
H H9_2 0.2985 0.7638 0.0585 0.028 Uiso calc U . R 1 . .
C C10_2 0.3082(3) 0.5839(2) 0.08703(11) 0.0228(5) Uani d . . . 1 . .
H H10_2 0.3743 0.5745 0.0459 0.027 Uiso calc U . R 1 . .
C C11_2 0.2579(3) 0.4843(2) 0.13756(11) 0.0197(5) Uani d . . . 1 . .
H H11_2 0.2861 0.4072 0.1316 0.024 Uiso calc U . R 1 . .
C C12_2 0.1642(3) 0.5020(2) 0.19749(11) 0.0182(5) Uani d . . . 1 . .
C C13_2 0.1062(3) 0.2948(2) 0.26504(11) 0.0188(5) Uani d . . . 1 . .
C C14_2 0.0549(3) 0.2460(2) 0.21395(11) 0.0179(4) Uani d . . . 1 . .
H H14_2 0.0192 0.2955 0.1733 0.021 Uiso calc U . R 1 . .
C C15_2 0.0562(3) 0.1242(2) 0.22285(11) 0.0189(5) Uani d . . . 1 . .
C C16_2 0.0992(3) 0.0506(2) 0.28318(11) 0.0191(5) Uani d . . . 1 . .
H H16_2 0.0964 -0.0327 0.2893 0.023 Uiso calc U . R 1 . .
C C17_2 0.1466(3) 0.0999(2) 0.33469(11) 0.0193(5) Uani d . . . 1 . .
C C18_2 0.1550(3) 0.2220(2) 0.32463(11) 0.0199(5) Uani d . . . 1 . .
H H18_2 0.1944 0.2555 0.3587 0.024 Uiso calc U . R 1 . .
C C19_2 0.0041(3) 0.0674(2) 0.16968(12) 0.0203(5) Uani d . . . 1 . .
C C20_2 -0.0503(4) 0.0938(3) 0.05593(13) 0.0313(6) Uani d . . . 1 . .
H H20A_2 -0.0383 0.1538 0.013 0.047 Uiso calc U . R 1 . .
H H20B_2 -0.1757 0.0648 0.066 0.047 Uiso calc U . R 1 . .
H H20C_2 0.0327 0.028 0.0522 0.047 Uiso calc U . R 1 . .
C C21_2 0.1839(3) 0.0263(2) 0.40223(12) 0.0222(5) Uani d . . . 1 . .
C C22_2 0.2029(4) -0.1656(2) 0.47058(13) 0.0353(6) Uani d . . . 1 . .
H H22A_2 0.2016 -0.2483 0.4677 0.053 Uiso calc U . R 1 . .
H H22B_2 0.1047 -0.1522 0.5044 0.053 Uiso calc U . R 1 . .
H H22C_2 0.3201 -0.1479 0.484 0.053 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1_1 C12_1 . 1.391(3) ?
N1_1 C1_1 . 1.401(3) ?
N1_1 C13_1 . 1.423(3) ?
O1_1 C19_1 . 1.209(3) ?
O2_1 C19_1 . 1.339(3) ?
O2_1 C20_1 . 1.445(3) ?
O3_1 C21_1 . 1.203(3) ?
O4_1 C21_1 . 1.341(3) ?
O4_1 C22_1 . 1.447(3) ?
C1_1 C2_1 . 1.392(3) ?
C1_1 C6_1 . 1.408(3) ?
C2_1 C3_1 . 1.385(3) ?
C2_1 H2_1 . 0.95 ?
C3_1 C4_1 . 1.397(4) ?
C3_1 H3_1 . 0.95 ?
C4_1 C5_1 . 1.375(4) ?
C4_1 H4_1 . 0.95 ?
C5_1 C6_1 . 1.402(3) ?
C5_1 H5_1 . 0.95 ?
C6_1 C7_1 . 1.441(3) ?
C7_1 C8_1 . 1.400(3) ?
C7_1 C12_1 . 1.403(3) ?
C8_1 C9_1 . 1.372(4) ?
C8_1 H8_1 . 0.95 ?
C9_1 C10_1 . 1.398(4) ?
C9_1 H9_1 . 0.95 ?
C10_1 C11_1 . 1.389(3) ?
C10_1 H10_1 . 0.95 ?
C11_1 C12_1 . 1.400(3) ?
C11_1 H11_1 . 0.95 ?
C13_1 C18_1 . 1.385(3) ?
C13_1 C14_1 . 1.394(3) ?
C14_1 C15_1 . 1.389(3) ?
C14_1 H14_1 . 0.95 ?
C15_1 C16_1 . 1.394(3) ?
C15_1 C19_1 . 1.489(3) ?
C16_1 C17_1 . 1.382(3) ?
C16_1 H16_1 . 0.95 ?
C17_1 C18_1 . 1.390(3) ?
C17_1 C21_1 . 1.493(3) ?
C18_1 H18_1 . 0.95 ?
C20_1 H20A_1 . 0.98 ?
C20_1 H20B_1 . 0.98 ?
C20_1 H20C_1 . 0.98 ?
C22_1 H22A_1 . 0.98 ?
C22_1 H22B_1 . 0.98 ?
C22_1 H22C_1 . 0.98 ?
N1_2 C12_2 . 1.394(3) ?
N1_2 C1_2 . 1.400(3) ?
N1_2 C13_2 . 1.418(3) ?
O1_2 C19_2 . 1.205(3) ?
O2_2 C19_2 . 1.340(3) ?
O2_2 C20_2 . 1.448(3) ?
O3_2 C21_2 . 1.206(3) ?
O4_2 C21_2 . 1.340(3) ?
O4_2 C22_2 . 1.450(3) ?
C1_2 C2_2 . 1.401(3) ?
C1_2 C6_2 . 1.410(3) ?
C2_2 C3_2 . 1.385(3) ?
C2_2 H2_2 . 0.95 ?
C3_2 C4_2 . 1.403(3) ?
C3_2 H3_2 . 0.95 ?
C4_2 C5_2 . 1.373(3) ?
C4_2 H4_2 . 0.95 ?
C5_2 C6_2 . 1.394(3) ?
C5_2 H5_2 . 0.95 ?
C6_2 C7_2 . 1.445(3) ?
C7_2 C8_2 . 1.392(3) ?
C7_2 C12_2 . 1.406(3) ?
C8_2 C9_2 . 1.384(3) ?
C8_2 H8_2 . 0.95 ?
C9_2 C10_2 . 1.395(3) ?
C9_2 H9_2 . 0.95 ?
C10_2 C11_2 . 1.386(3) ?
C10_2 H10_2 . 0.95 ?
C11_2 C12_2 . 1.393(3) ?
C11_2 H11_2 . 0.95 ?
C13_2 C18_2 . 1.385(3) ?
C13_2 C14_2 . 1.392(3) ?
C14_2 C15_2 . 1.388(3) ?
C14_2 H14_2 . 0.95 ?
C15_2 C16_2 . 1.386(3) ?
C15_2 C19_2 . 1.488(3) ?
C16_2 C17_2 . 1.393(3) ?
C16_2 H16_2 . 0.95 ?
C17_2 C18_2 . 1.393(3) ?
C17_2 C21_2 . 1.490(3) ?
C18_2 H18_2 . 0.95 ?
C20_2 H20A_2 . 0.98 ?
C20_2 H20B_2 . 0.98 ?
C20_2 H20C_2 . 0.98 ?
C22_2 H22A_2 . 0.98 ?
C22_2 H22B_2 . 0.98 ?
C22_2 H22C_2 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12_1 N1_1 C1_1 . . 108.47(19) ?
C12_1 N1_1 C13_1 . . 126.00(19) ?
C1_1 N1_1 C13_1 . . 125.0(2) ?
C19_1 O2_1 C20_1 . . 114.56(19) ?
C21_1 O4_1 C22_1 . . 114.79(18) ?
C2_1 C1_1 N1_1 . . 130.2(2) ?
C2_1 C1_1 C6_1 . . 121.4(2) ?
N1_1 C1_1 C6_1 . . 108.4(2) ?
C3_1 C2_1 C1_1 . . 117.8(2) ?
C3_1 C2_1 H2_1 . . 121.1 ?
C1_1 C2_1 H2_1 . . 121.1 ?
C2_1 C3_1 C4_1 . . 121.3(2) ?
C2_1 C3_1 H3_1 . . 119.4 ?
C4_1 C3_1 H3_1 . . 119.4 ?
C5_1 C4_1 C3_1 . . 121.2(2) ?
C5_1 C4_1 H4_1 . . 119.4 ?
C3_1 C4_1 H4_1 . . 119.4 ?
C4_1 C5_1 C6_1 . . 118.6(2) ?
C4_1 C5_1 H5_1 . . 120.7 ?
C6_1 C5_1 H5_1 . . 120.7 ?
C5_1 C6_1 C1_1 . . 119.8(2) ?
C5_1 C6_1 C7_1 . . 133.2(2) ?
C1_1 C6_1 C7_1 . . 107.0(2) ?
C8_1 C7_1 C12_1 . . 119.9(2) ?
C8_1 C7_1 C6_1 . . 133.0(2) ?
C12_1 C7_1 C6_1 . . 107.1(2) ?
C9_1 C8_1 C7_1 . . 118.8(2) ?
C9_1 C8_1 H8_1 . . 120.6 ?
C7_1 C8_1 H8_1 . . 120.6 ?
C8_1 C9_1 C10_1 . . 121.1(2) ?
C8_1 C9_1 H9_1 . . 119.4 ?
C10_1 C9_1 H9_1 . . 119.4 ?
C11_1 C10_1 C9_1 . . 121.4(2) ?
C11_1 C10_1 H10_1 . . 119.3 ?
C9_1 C10_1 H10_1 . . 119.3 ?
C10_1 C11_1 C12_1 . . 117.4(2) ?
C10_1 C11_1 H11_1 . . 121.3 ?
C12_1 C11_1 H11_1 . . 121.3 ?
N1_1 C12_1 C11_1 . . 129.6(2) ?
N1_1 C12_1 C7_1 . . 109.0(2) ?
C11_1 C12_1 C7_1 . . 121.4(2) ?
C18_1 C13_1 C14_1 . . 120.0(2) ?
C18_1 C13_1 N1_1 . . 120.0(2) ?
C14_1 C13_1 N1_1 . . 120.0(2) ?
C15_1 C14_1 C13_1 . . 119.6(2) ?
C15_1 C14_1 H14_1 . . 120.2 ?
C13_1 C14_1 H14_1 . . 120.2 ?
C14_1 C15_1 C16_1 . . 120.3(2) ?
C14_1 C15_1 C19_1 . . 122.0(2) ?
C16_1 C15_1 C19_1 . . 117.7(2) ?
C17_1 C16_1 C15_1 . . 119.6(2) ?
C17_1 C16_1 H16_1 . . 120.2 ?
C15_1 C16_1 H16_1 . . 120.2 ?
C16_1 C17_1 C18_1 . . 120.4(2) ?
C16_1 C17_1 C21_1 . . 122.1(2) ?
C18_1 C17_1 C21_1 . . 117.4(2) ?
C13_1 C18_1 C17_1 . . 119.9(2) ?
C13_1 C18_1 H18_1 . . 120.0 ?
C17_1 C18_1 H18_1 . . 120.0 ?
O1_1 C19_1 O2_1 . . 123.5(2) ?
O1_1 C19_1 C15_1 . . 123.6(2) ?
O2_1 C19_1 C15_1 . . 112.8(2) ?
O2_1 C20_1 H20A_1 . . 109.5 ?
O2_1 C20_1 H20B_1 . . 109.5 ?
H20A_1 C20_1 H20B_1 . . 109.5 ?
O2_1 C20_1 H20C_1 . . 109.5 ?
H20A_1 C20_1 H20C_1 . . 109.5 ?
H20B_1 C20_1 H20C_1 . . 109.5 ?
O3_1 C21_1 O4_1 . . 123.5(2) ?
O3_1 C21_1 C17_1 . . 123.9(2) ?
O4_1 C21_1 C17_1 . . 112.5(2) ?
O4_1 C22_1 H22A_1 . . 109.5 ?
O4_1 C22_1 H22B_1 . . 109.5 ?
H22A_1 C22_1 H22B_1 . . 109.5 ?
O4_1 C22_1 H22C_1 . . 109.5 ?
H22A_1 C22_1 H22C_1 . . 109.5 ?
H22B_1 C22_1 H22C_1 . . 109.5 ?
C12_2 N1_2 C1_2 . . 108.14(19) ?
C12_2 N1_2 C13_2 . . 125.85(19) ?
C1_2 N1_2 C13_2 . . 125.77(19) ?
C19_2 O2_2 C20_2 . . 114.5(2) ?
C21_2 O4_2 C22_2 . . 114.63(19) ?
N1_2 C1_2 C2_2 . . 130.0(2) ?
N1_2 C1_2 C6_2 . . 108.90(19) ?
C2_2 C1_2 C6_2 . . 121.1(2) ?
C3_2 C2_2 C1_2 . . 117.8(2) ?
C3_2 C2_2 H2_2 . . 121.1 ?
C1_2 C2_2 H2_2 . . 121.1 ?
C2_2 C3_2 C4_2 . . 121.0(2) ?
C2_2 C3_2 H3_2 . . 119.5 ?
C4_2 C3_2 H3_2 . . 119.5 ?
C5_2 C4_2 C3_2 . . 121.3(2) ?
C5_2 C4_2 H4_2 . . 119.4 ?
C3_2 C4_2 H4_2 . . 119.4 ?
C4_2 C5_2 C6_2 . . 118.9(2) ?
C4_2 C5_2 H5_2 . . 120.6 ?
C6_2 C5_2 H5_2 . . 120.6 ?
C5_2 C6_2 C1_2 . . 119.9(2) ?
C5_2 C6_2 C7_2 . . 133.2(2) ?
C1_2 C6_2 C7_2 . . 106.8(2) ?
C8_2 C7_2 C12_2 . . 120.0(2) ?
C8_2 C7_2 C6_2 . . 133.1(2) ?
C12_2 C7_2 C6_2 . . 106.9(2) ?
C9_2 C8_2 C7_2 . . 118.9(2) ?
C9_2 C8_2 H8_2 . . 120.5 ?
C7_2 C8_2 H8_2 . . 120.5 ?
C8_2 C9_2 C10_2 . . 120.3(2) ?
C8_2 C9_2 H9_2 . . 119.9 ?
C10_2 C9_2 H9_2 . . 119.9 ?
C11_2 C10_2 C9_2 . . 122.1(2) ?
C11_2 C10_2 H10_2 . . 119.0 ?
C9_2 C10_2 H10_2 . . 119.0 ?
C10_2 C11_2 C12_2 . . 117.1(2) ?
C10_2 C11_2 H11_2 . . 121.4 ?
C12_2 C11_2 H11_2 . . 121.4 ?
C11_2 C12_2 N1_2 . . 129.1(2) ?
C11_2 C12_2 C7_2 . . 121.6(2) ?
N1_2 C12_2 C7_2 . . 109.2(2) ?
C18_2 C13_2 C14_2 . . 120.0(2) ?
C18_2 C13_2 N1_2 . . 120.1(2) ?
C14_2 C13_2 N1_2 . . 119.8(2) ?
C15_2 C14_2 C13_2 . . 119.5(2) ?
C15_2 C14_2 H14_2 . . 120.3 ?
C13_2 C14_2 H14_2 . . 120.3 ?
C16_2 C15_2 C14_2 . . 120.9(2) ?
C16_2 C15_2 C19_2 . . 117.4(2) ?
C14_2 C15_2 C19_2 . . 121.7(2) ?
C15_2 C16_2 C17_2 . . 119.4(2) ?
C15_2 C16_2 H16_2 . . 120.3 ?
C17_2 C16_2 H16_2 . . 120.3 ?
C16_2 C17_2 C18_2 . . 120.0(2) ?
C16_2 C17_2 C21_2 . . 122.2(2) ?
C18_2 C17_2 C21_2 . . 117.8(2) ?
C13_2 C18_2 C17_2 . . 120.2(2) ?
C13_2 C18_2 H18_2 . . 119.9 ?
C17_2 C18_2 H18_2 . . 119.9 ?
O1_2 C19_2 O2_2 . . 123.4(2) ?
O1_2 C19_2 C15_2 . . 124.4(2) ?
O2_2 C19_2 C15_2 . . 112.2(2) ?
O2_2 C20_2 H20A_2 . . 109.5 ?
O2_2 C20_2 H20B_2 . . 109.5 ?
H20A_2 C20_2 H20B_2 . . 109.5 ?
O2_2 C20_2 H20C_2 . . 109.5 ?
H20A_2 C20_2 H20C_2 . . 109.5 ?
H20B_2 C20_2 H20C_2 . . 109.5 ?
O3_2 C21_2 O4_2 . . 123.9(2) ?
O3_2 C21_2 C17_2 . . 124.0(2) ?
O4_2 C21_2 C17_2 . . 112.1(2) ?
O4_2 C22_2 H22A_2 . . 109.5 ?
O4_2 C22_2 H22B_2 . . 109.5 ?
H22A_2 C22_2 H22B_2 . . 109.5 ?
O4_2 C22_2 H22C_2 . . 109.5 ?
H22A_2 C22_2 H22C_2 . . 109.5 ?
H22B_2 C22_2 H22C_2 . . 109.5 ?

####################################################################### 
# 
# 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_CME_P21c
_database_code_depnum_ccdc_archive 'CCDC 1489317'
_audit_update_record             
;
2016-06-30 deposited with the CCDC.
2016-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'CPB 2'
_chemical_name_common            CME
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36

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'

_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                   20.7631(5)
_cell_length_b                   3.95300(10)
_cell_length_c                   18.9724(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.9960(10)
_cell_angle_gamma                90
_cell_volume                     1533.55(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9783
_cell_measurement_theta_min      4.3244
_cell_measurement_theta_max      72.1685

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.699
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   \^Omulti-scan\~O
_exptl_absorpt_correction_T_min  0.6002
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Apex v2014.11 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 Quest ECO CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20952
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.324
_diffrn_reflns_theta_max         79.282
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3249
_reflns_number_gt                2697
_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       'Apex2 v2014.11 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.30C (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.30C (Bruker, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
Shelxtl (Bruker, 2013),
Publcif (westrip, 2010)
;
_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)+(0.0426P)²+0.7720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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
C1 C 0.19002(7) 1.0721(3) 0.53315(7) 0.0137(3) Uani 1 1 d . . . . .
O1 O 0.48376(5) 0.4349(3) 0.63794(6) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.22316(5) 0.9397(3) 0.48092(6) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.21391(7) 1.1596(4) 0.60413(8) 0.0152(3) Uani 1 1 d . . . . .
H2 H 0.2586 1.1275 0.6245 0.018 Uiso 1 1 calc R U . . .
O2 O 0.38417(5) 0.3887(3) 0.66885(5) 0.0162(2) Uani 1 1 d . . . . .
C3 C 0.17006(7) 1.2951(4) 0.64391(8) 0.0179(3) Uani 1 1 d . . . . .
H3 H 0.1852 1.3588 0.6922 0.021 Uiso 1 1 calc R U . . .
C4 C 0.10404(7) 1.3400(4) 0.61447(8) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.0750 1.4315 0.6431 0.024 Uiso 1 1 calc R U . . .
C5 C 0.08061(7) 1.2526(4) 0.54410(8) 0.0179(3) Uani 1 1 d . . . . .
H5 H 0.0357 1.2829 0.5243 0.022 Uiso 1 1 calc R U . . .
C6 C 0.12380(7) 1.1192(4) 0.50243(8) 0.0147(3) Uani 1 1 d . . . . .
C7 C 0.11606(7) 1.0059(4) 0.42905(8) 0.0147(3) Uani 1 1 d . . . . .
C8 C 0.06242(7) 0.9839(4) 0.37354(8) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.0206 1.0614 0.3802 0.022 Uiso 1 1 calc R U . . .
C9 C 0.07106(7) 0.8475(4) 0.30868(8) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.0349 0.8324 0.2705 0.024 Uiso 1 1 calc R U . . .
C10 C 0.13250(7) 0.7315(4) 0.29878(8) 0.0188(3) Uani 1 1 d . . . . .
H10 H 0.1372 0.6353 0.2541 0.023 Uiso 1 1 calc R U . . .
C11 C 0.18673(7) 0.7539(4) 0.35278(8) 0.0164(3) Uani 1 1 d . . . . .
H11 H 0.2284 0.6754 0.3458 0.020 Uiso 1 1 calc R U . . .
C12 C 0.17794(7) 0.8954(4) 0.41760(7) 0.0142(3) Uani 1 1 d . . . . .
C13 C 0.29138(6) 0.8800(4) 0.48964(7) 0.0132(3) Uani 1 1 d . . . . .
C14 C 0.32715(7) 0.9933(4) 0.43855(8) 0.0152(3) Uani 1 1 d . . . . .
H14 H 0.3057 1.1095 0.3972 0.018 Uiso 1 1 calc R U . . .
C15 C 0.39425(7) 0.9364(4) 0.44802(7) 0.0157(3) Uani 1 1 d . . . . .
H15 H 0.4184 1.0099 0.4126 0.019 Uiso 1 1 calc R U . . .
C16 C 0.42606(7) 0.7724(4) 0.50900(8) 0.0146(3) Uani 1 1 d . . . . .
H16 H 0.4719 0.7360 0.5157 0.018 Uiso 1 1 calc R U . . .
C17 C 0.39034(7) 0.6617(4) 0.56033(7) 0.0138(3) Uani 1 1 d . . . . .
C18 C 0.32300(6) 0.7128(4) 0.55043(7) 0.0132(3) Uani 1 1 d . . . . .
H18 H 0.2987 0.6336 0.5852 0.016 Uiso 1 1 calc R U . . .
C19 C 0.42543(7) 0.4846(4) 0.62513(7) 0.0140(3) Uani 1 1 d . . . . .
C20 C 0.41337(7) 0.2253(4) 0.73541(8) 0.0182(3) Uani 1 1 d . . . . .
H20A H 0.4397 0.3897 0.7676 0.022 Uiso 1 1 calc R U . . .
H20B H 0.4422 0.0376 0.7258 0.022 Uiso 1 1 calc R U . . .
C21 C 0.35809(7) 0.0922(4) 0.76921(8) 0.0209(3) Uani 1 1 d . . . . .
H21A H 0.3339 -0.0791 0.7379 0.031 Uiso 1 1 calc R U . . .
H21B H 0.3287 0.2786 0.7761 0.031 Uiso 1 1 calc R U . . .
H21C H 0.3757 -0.0095 0.8157 0.031 Uiso 1 1 calc R U . . .


_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
C1 C2 1.395(2) . ?
C1 N1 1.4020(17) . ?
C1 C6 1.4095(19) . ?
O1 C19 1.2092(17) . ?
N1 C12 1.4014(18) . ?
N1 C13 1.4173(17) . ?
C2 C3 1.387(2) . ?
O2 C19 1.3463(16) . ?
O2 C20 1.4539(17) . ?
C3 C4 1.399(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.445(2) . ?
C7 C8 1.396(2) . ?
C7 C12 1.4090(19) . ?
C8 C9 1.383(2) . ?
C9 C10 1.398(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.392(2) . ?
C13 C18 1.3910(19) . ?
C13 C14 1.3934(19) . ?
C14 C15 1.392(2) . ?
C15 C16 1.389(2) . ?
C16 C17 1.3930(19) . ?
C17 C18 1.3928(19) . ?
C17 C19 1.490(2) . ?
C20 C21 1.504(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
C2 C1 N1 129.70(13) . . ?
C2 C1 C6 121.61(12) . . ?
N1 C1 C6 108.67(12) . . ?
C12 N1 C1 108.34(11) . . ?
C12 N1 C13 125.91(11) . . ?
C1 N1 C13 125.66(12) . . ?
C3 C2 C1 117.64(13) . . ?
C19 O2 C20 116.51(11) . . ?
C2 C3 C4 121.46(14) . . ?
C5 C4 C3 120.66(13) . . ?
C4 C5 C6 119.17(13) . . ?
C5 C6 C1 119.44(13) . . ?
C5 C6 C7 133.40(13) . . ?
C1 C6 C7 107.15(12) . . ?
C8 C7 C12 119.58(13) . . ?
C8 C7 C6 133.38(13) . . ?
C12 C7 C6 107.03(12) . . ?
C9 C8 C7 119.04(13) . . ?
C8 C9 C10 120.63(14) . . ?
C11 C10 C9 121.48(14) . . ?
C10 C11 C12 117.65(13) . . ?
C11 C12 N1 129.55(13) . . ?
C11 C12 C7 121.59(13) . . ?
N1 C12 C7 108.80(12) . . ?
C18 C13 C14 119.85(13) . . ?
C18 C13 N1 119.62(12) . . ?
C14 C13 N1 120.52(13) . . ?
C15 C14 C13 120.04(13) . . ?
C16 C15 C14 120.23(13) . . ?
C15 C16 C17 119.67(13) . . ?
C18 C17 C16 120.25(13) . . ?
C18 C17 C19 120.99(12) . . ?
C16 C17 C19 118.75(12) . . ?
C13 C18 C17 119.94(13) . . ?
O1 C19 O2 123.55(13) . . ?
O1 C19 C17 124.83(13) . . ?
O2 C19 C17 111.62(11) . . ?
O2 C20 C21 106.96(11) . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/Hexanes'
_exptl_crystal_preparation       ', Luminescent'
