# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_CPCMERI-1
_database_code_depnum_ccdc_archive 'CCDC 1571158'
_audit_update_record             
;
2017-08-28 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N2'
_chemical_formula_weight         384.46

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'

_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                   11.7907(4)
_cell_length_b                   7.1668(2)
_cell_length_c                   24.0105(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.472(2)
_cell_angle_gamma                90
_cell_volume                     2006.79(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.6221
_cell_measurement_theta_max      28.2990

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .18
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36774
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.746
_diffrn_reflns_theta_max         28.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5087
_reflns_number_gt                3931
_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    'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0577P)²+0.5060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0049(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5087
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
N001 N 0.20081(9) 0.73084(15) 0.42675(5) 0.0427(3) Uani 1 1 d . . . . .
N002 N 0.32473(9) 0.75280(15) 0.59344(5) 0.0430(3) Uani 1 1 d . . . . .
C003 C 0.24950(10) 0.57797(17) 0.40175(5) 0.0377(3) Uani 1 1 d . . . . .
C004 C 0.29424(10) 0.61162(16) 0.35069(5) 0.0361(3) Uani 1 1 d . . . . .
C005 C 0.43519(10) 0.86795(17) 0.52432(5) 0.0369(3) Uani 1 1 d . . . . .
C006 C 0.10479(11) 0.70996(18) 0.44358(5) 0.0415(3) Uani 1 1 d . . . . .
H006 H 0.0665 0.5968 0.4371 0.050 Uiso 1 1 calc R U . . .
C007 C 0.34697(10) 0.46111(18) 0.32581(5) 0.0397(3) Uani 1 1 d . . . . .
C008 C 0.05231(11) 0.85877(17) 0.47290(5) 0.0392(3) Uani 1 1 d . . . . .
C009 C 0.16841(11) 0.63133(18) 0.63872(5) 0.0404(3) Uani 1 1 d . . . . .
C00A C 0.48440(11) 0.82458(18) 0.47674(5) 0.0424(3) Uani 1 1 d . . . . .
H00A H 0.4740 0.7062 0.4609 0.051 Uiso 1 1 calc R U . . .
C00B C 0.27354(11) 0.59990(18) 0.61760(5) 0.0411(3) Uani 1 1 d . . . . .
C00C C 0.54830(11) 0.95434(18) 0.45274(5) 0.0427(3) Uani 1 1 d . . . . .
H00C H 0.5807 0.9229 0.4210 0.051 Uiso 1 1 calc R U . . .
C00D C 0.37088(11) 0.72448(18) 0.54974(5) 0.0406(3) Uani 1 1 d . . . . .
H00D H 0.3635 0.6071 0.5331 0.049 Uiso 1 1 calc R U . . .
C00E C 0.11323(12) 1.01819(19) 0.49188(6) 0.0442(3) Uani 1 1 d . . . . .
H00E H 0.1894 1.0307 0.4866 0.053 Uiso 1 1 calc R U . . .
C00F C 0.25949(11) 0.40510(18) 0.42621(6) 0.0443(3) Uani 1 1 d . . . . .
H00F H 0.2306 0.3849 0.4597 0.053 Uiso 1 1 calc R U . . .
C00G C 0.06141(12) 1.15790(19) 0.51853(6) 0.0443(3) Uani 1 1 d . . . . .
H00G H 0.1028 1.2642 0.5309 0.053 Uiso 1 1 calc R U . . .
C00H C 0.28527(12) 0.78612(18) 0.32319(6) 0.0463(3) Uani 1 1 d . . . . .
H00H H 0.2515 0.8860 0.3393 0.056 Uiso 1 1 calc R U . . .
C00I C 0.35550(12) 0.28529(19) 0.35276(6) 0.0472(3) Uani 1 1 d . . . . .
H00I H 0.3910 0.1870 0.3369 0.057 Uiso 1 1 calc R U . . .
C00J C 0.31261(12) 0.25819(19) 0.40147(6) 0.0490(3) Uani 1 1 d . . . . .
H00J H 0.3185 0.1415 0.4186 0.059 Uiso 1 1 calc R U . . .
C00K C 0.11147(12) 0.8047(2) 0.63364(6) 0.0497(3) Uani 1 1 d . . . . .
H00K H 0.1419 0.9029 0.6153 0.060 Uiso 1 1 calc R U . . .
C00L C 0.11999(12) 0.4821(2) 0.66643(5) 0.0477(3) Uani 1 1 d . . . . .
C00M C 0.32704(14) 0.4300(2) 0.62511(6) 0.0523(3) Uani 1 1 d . . . . .
H00M H 0.3969 0.4117 0.6123 0.063 Uiso 1 1 calc R U . . .
C00N C 0.38742(12) 0.4923(2) 0.27408(6) 0.0504(3) Uani 1 1 d . . . . .
H00N H 0.4226 0.3953 0.2574 0.060 Uiso 1 1 calc R U . . .
C00O C 0.37592(14) 0.6609(2) 0.24837(6) 0.0560(4) Uani 1 1 d . . . . .
H00O H 0.4017 0.6777 0.2139 0.067 Uiso 1 1 calc R U . . .
C00P C 0.01211(13) 0.8295(3) 0.65537(7) 0.0603(4) Uani 1 1 d . . . . .
H00P H -0.0246 0.9446 0.6519 0.072 Uiso 1 1 calc R U . . .
C00Q C 0.32552(14) 0.8100(2) 0.27327(6) 0.0546(4) Uani 1 1 d . . . . .
H00Q H 0.3194 0.9260 0.2557 0.066 Uiso 1 1 calc R U . . .
C00R C 0.01657(13) 0.5145(2) 0.68808(6) 0.0582(4) Uani 1 1 d . . . . .
H00R H -0.0163 0.4183 0.7062 0.070 Uiso 1 1 calc R U . . .
C00S C 0.17703(16) 0.3088(2) 0.67196(7) 0.0601(4) Uani 1 1 d . . . . .
H00S H 0.1452 0.2104 0.6896 0.072 Uiso 1 1 calc R U . . .
C00T C 0.27734(17) 0.2835(2) 0.65194(7) 0.0624(4) Uani 1 1 d . . . . .
H00T H 0.3137 0.1681 0.6560 0.075 Uiso 1 1 calc R U . . .
C00U C -0.03518(13) 0.6828(3) 0.68289(7) 0.0629(4) Uani 1 1 d . . . . .
H00U H -0.1028 0.7016 0.6977 0.075 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
N001 C006 1.2657(16) . ?
N001 C003 1.4112(15) . ?
N002 C00D 1.2674(16) . ?
N002 C00B 1.4159(15) . ?
C003 C00F 1.3688(18) . ?
C003 C004 1.4248(17) . ?
C004 C00H 1.4109(18) . ?
C004 C007 1.4200(16) . ?
C005 C00C 1.3898(18) 3_676 ?
C005 C00A 1.3907(17) . ?
C005 C00D 1.4632(16) . ?
C006 C008 1.4644(17) . ?
C006 H006 0.9300 . ?
C007 C00I 1.4133(19) . ?
C007 C00N 1.4123(19) . ?
C008 C00E 1.3901(19) . ?
C008 C00G 1.3914(18) 3_576 ?
C009 C00K 1.409(2) . ?
C009 C00L 1.4230(17) . ?
C009 C00B 1.4246(18) . ?
C00A C00C 1.3756(17) . ?
C00A H00A 0.9300 . ?
C00B C00M 1.3708(19) . ?
C00C C005 1.3898(18) 3_676 ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E C00G 1.3786(17) . ?
C00E H00E 0.9300 . ?
C00F C00J 1.4012(18) . ?
C00F H00F 0.9300 . ?
C00G C008 1.3913(18) 3_576 ?
C00G H00G 0.9300 . ?
C00H C00Q 1.3632(19) . ?
C00H H00H 0.9300 . ?
C00I C00J 1.355(2) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K C00P 1.362(2) . ?
C00K H00K 0.9300 . ?
C00L C00S 1.409(2) . ?
C00L C00R 1.413(2) . ?
C00M C00T 1.405(2) . ?
C00M H00M 0.9300 . ?
C00N C00O 1.355(2) . ?
C00N H00N 0.9300 . ?
C00O C00Q 1.399(2) . ?
C00O H00O 0.9300 . ?
C00P C00U 1.400(2) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R C00U 1.350(2) . ?
C00R H00R 0.9300 . ?
C00S C00T 1.353(2) . ?
C00S H00S 0.9300 . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?

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
C006 N001 C003 118.88(11) . . ?
C00D N002 C00B 118.44(11) . . ?
C00F C003 N001 122.34(11) . . ?
C00F C003 C004 120.20(11) . . ?
N001 C003 C004 117.39(11) . . ?
C00H C004 C007 118.93(11) . . ?
C00H C004 C003 122.75(11) . . ?
C007 C004 C003 118.29(11) . . ?
C00C C005 C00A 118.64(11) 3_676 . ?
C00C C005 C00D 121.97(11) 3_676 . ?
C00A C005 C00D 119.36(11) . . ?
N001 C006 C008 121.91(12) . . ?
N001 C006 H006 119.0 . . ?
C008 C006 H006 119.0 . . ?
C00I C007 C00N 122.23(12) . . ?
C00I C007 C004 119.39(11) . . ?
C00N C007 C004 118.38(12) . . ?
C00E C008 C00G 119.00(11) . 3_576 ?
C00E C008 C006 121.44(11) . . ?
C00G C008 C006 119.55(12) 3_576 . ?
C00K C009 C00L 118.98(12) . . ?
C00K C009 C00B 122.49(11) . . ?
C00L C009 C00B 118.53(12) . . ?
C00C C00A C005 120.90(12) . . ?
C00C C00A H00A 119.6 . . ?
C005 C00A H00A 119.6 . . ?
C00M C00B N002 121.70(12) . . ?
C00M C00B C009 120.09(12) . . ?
N002 C00B C009 117.98(11) . . ?
C00A C00C C005 120.46(11) . 3_676 ?
C00A C00C H00C 119.8 . . ?
C005 C00C H00C 119.8 3_676 . ?
N002 C00D C005 123.02(12) . . ?
N002 C00D H00D 118.5 . . ?
C005 C00D H00D 118.5 . . ?
C00G C00E C008 120.41(12) . . ?
C00G C00E H00E 119.8 . . ?
C008 C00E H00E 119.8 . . ?
C003 C00F C00J 120.92(12) . . ?
C003 C00F H00F 119.5 . . ?
C00J C00F H00F 119.5 . . ?
C00E C00G C008 120.59(12) . 3_576 ?
C00E C00G H00G 119.7 . . ?
C008 C00G H00G 119.7 3_576 . ?
C00Q C00H C004 120.73(13) . . ?
C00Q C00H H00H 119.6 . . ?
C004 C00H H00H 119.6 . . ?
C00J C00I C007 120.84(12) . . ?
C00J C00I H00I 119.6 . . ?
C007 C00I H00I 119.6 . . ?
C00I C00J C00F 120.35(13) . . ?
C00I C00J H00J 119.8 . . ?
C00F C00J H00J 119.8 . . ?
C00P C00K C009 120.50(14) . . ?
C00P C00K H00K 119.8 . . ?
C009 C00K H00K 119.8 . . ?
C00S C00L C00R 122.40(13) . . ?
C00S C00L C009 119.19(13) . . ?
C00R C00L C009 118.40(14) . . ?
C00B C00M C00T 120.63(14) . . ?
C00B C00M H00M 119.7 . . ?
C00T C00M H00M 119.7 . . ?
C00O C00N C007 121.18(13) . . ?
C00O C00N H00N 119.4 . . ?
C007 C00N H00N 119.4 . . ?
C00N C00O C00Q 120.45(13) . . ?
C00N C00O H00O 119.8 . . ?
C00Q C00O H00O 119.8 . . ?
C00K C00P C00U 120.50(16) . . ?
C00K C00P H00P 119.7 . . ?
C00U C00P H00P 119.7 . . ?
C00H C00Q C00O 120.31(14) . . ?
C00H C00Q H00Q 119.8 . . ?
C00O C00Q H00Q 119.8 . . ?
C00U C00R C00L 121.05(14) . . ?
C00U C00R H00R 119.5 . . ?
C00L C00R H00R 119.5 . . ?
C00T C00S C00L 120.99(13) . . ?
C00T C00S H00S 119.5 . . ?
C00L C00S H00S 119.5 . . ?
C00S C00T C00M 120.55(15) . . ?
C00S C00T H00T 119.7 . . ?
C00M C00T H00T 119.7 . . ?
C00R C00U C00P 120.56(14) . . ?
C00R C00U H00U 119.7 . . ?
C00P C00U H00U 119.7 . . ?

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039

