# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_C35H24N2O1
_database_code_depnum_ccdc_archive 'CCDC 2169390'
loop_
_audit_author_name
_audit_author_address
'Jenny Forrester'
;North Carolina State University
United States of America
;
_audit_update_record             
;
2022-04-29 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT027_C35H24N2O1          
;
RESPONSE: Weak reflection caused by the poor quality crystals. However, 
the data quality is sufficient for the structure validation.
;

_audit_creation_date             2022-03-04
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 'cu_H2_15_2A_0m in C2/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   35.8398(12)
_cell_length_b                   4.60330(10)
_cell_length_c                   15.1676(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.825(2)
_cell_angle_gamma                90
_cell_volume                     2306.42(12)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C35 H24 N2 O1 
# Dc =      1.41 Fooo =   1024.00 Mu =      6.61 M =    488.59
# Found Formula = C35 H24 N2 O1 
# Dc =      1.41 FOOO =   1024.00 Mu =      6.61 M =    488.59

_chemical_formula_sum            'C35 H24 N2 O1'
_chemical_formula_moiety         'C35 H24 N2 O1'
_chemical_compound_source        ?
_chemical_formula_weight         488.59


_cell_measurement_reflns_used    8528
_cell_measurement_theta_min      3
_cell_measurement_theta_max      66
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.010
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_max          0.150

_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.661

# Sheldrick geometric approximatio 0.95 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex4'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex4 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex4 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex4 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            17530
_reflns_number_total             2025
_diffrn_reflns_av_R_equivalents  0.086
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2025 
# Theoretical number of reflections is about 4071 


_diffrn_reflns_theta_min         2.675
_diffrn_reflns_theta_max         66.554
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        65.223
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -42
_reflns_limit_h_max              38
_reflns_limit_k_min              0
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.17
_oxford_diffrn_Wilson_scale      64.35

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.41


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     4
_refine_ls_number_parameters     210
_oxford_refine_ls_R_factor_ref   0.0792
_refine_ls_wR_factor_ref         0.1829
_refine_ls_goodness_of_fit_ref   1.0249
_refine_ls_shift/su_max          0.0002153
_refine_ls_shift/su_mean         0.0000314


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2020
_refine_ls_R_factor_all          0.0792
_refine_ls_wR_factor_all         0.1829

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1528
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_gt          0.1625

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.12P)² + 2.17P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.48095(5) -0.1994(4) 0.29570(14) 0.0286 1.0000 Uani D . . . . .
C18 C 0.5000 -0.3563(6) 0.2500 0.0267 1.0000 Uani DS T . . . .
O3 O 0.5000 -0.6250(5) 0.2500 0.0386 1.0000 Uani S T . . . .
C1 C 0.46105(7) -0.3394(5) 0.35204(18) 0.0303 1.0000 Uani D . . . . .
C2 C 0.43496(7) -0.1253(4) 0.37777(17) 0.0279 1.0000 Uani . . . . . .
C3 C 0.39958(6) -0.0068(4) 0.30724(16) 0.0257 1.0000 Uani . . . . . .
C4 C 0.38573(7) -0.0880(5) 0.20762(17) 0.0291 1.0000 Uani . . . . . .
C5 C 0.35219(7) 0.0316(5) 0.14089(18) 0.0298 1.0000 Uani . . . . . .
C6 C 0.32862(7) 0.2429(4) 0.16556(17) 0.0280 1.0000 Uani . . . . . .
C7 C 0.34090(6) 0.3246(4) 0.26329(16) 0.0258 1.0000 Uani . . . . . .
C8 C 0.37632(6) 0.1991(4) 0.33385(16) 0.0257 1.0000 Uani . . . . . .
C9 C 0.38859(6) 0.2852(5) 0.43140(17) 0.0279 1.0000 Uani . . . . . .
C10 C 0.42346(7) 0.1616(5) 0.49970(18) 0.0307 1.0000 Uani . . . . . .
C11 C 0.44602(7) -0.0399(5) 0.47245(18) 0.0305 1.0000 Uani . . . . . .
C12 C 0.36446(7) 0.4951(5) 0.45605(18) 0.0309 1.0000 Uani . . . . . .
C13 C 0.33107(7) 0.6128(5) 0.38924(18) 0.0319 1.0000 Uani . . . . . .
C14 C 0.31792(7) 0.5322(4) 0.28992(17) 0.0287 1.0000 Uani . . . . . .
C15 C 0.28359(7) 0.6543(5) 0.21996(18) 0.0320 1.0000 Uani . . . . . .
C16 C 0.27180(7) 0.5738(5) 0.12497(19) 0.0343 1.0000 Uani . . . . . .
C17 C 0.29393(7) 0.3717(5) 0.09771(18) 0.0326 1.0000 Uani . . . . . .
H11 H 0.4814(8) -0.425(5) 0.4117(18) 0.0269 1.0000 Uiso . . . . . .
H12 H 0.4447(7) -0.514(5) 0.3105(18) 0.0252 1.0000 Uiso . . . . . .
H41 H 0.3999(7) -0.240(5) 0.1874(17) 0.0227 1.0000 Uiso . . . . . .
H51 H 0.3446(10) -0.033(7) 0.073(2) 0.0494 1.0000 Uiso . . . . . .
H101 H 0.4329(9) 0.225(6) 0.568(2) 0.0434 1.0000 Uiso . . . . . .
H111 H 0.4707(9) -0.141(6) 0.525(2) 0.0401 1.0000 Uiso . . . . . .
H121 H 0.3752(9) 0.559(7) 0.523(2) 0.0486 1.0000 Uiso . . . . . .
H131 H 0.3153(8) 0.775(5) 0.4064(19) 0.0291 1.0000 Uiso . . . . . .
H151 H 0.2706(9) 0.811(6) 0.240(2) 0.0436 1.0000 Uiso . . . . . .
H161 H 0.2490(11) 0.672(7) 0.079(3) 0.0595 1.0000 Uiso . . . . . .
H171 H 0.2850(9) 0.316(7) 0.027(2) 0.0492 1.0000 Uiso . . . . . .
H1 H 0.4828(7) -0.013(4) 0.2959(17) 0.0336(19) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.12711(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C18 . 1.355(2) yes
N1 . C1 . 1.458(3) yes
N1 . H1 . 0.862(17) no
C18 . O3 . 1.237(4) yes
C1 . C2 . 1.510(3) yes
C1 . H11 . 1.00(3) no
C1 . H12 . 1.05(3) no
C2 . C3 . 1.413(3) yes
C2 . C11 . 1.390(3) yes
C3 . C4 . 1.445(3) yes
C3 . C8 . 1.420(3) yes
C4 . C5 . 1.352(3) yes
C4 . H41 . 0.98(2) no
C5 . C6 . 1.430(3) yes
C5 . H51 . 1.00(3) no
C6 . C7 . 1.423(3) yes
C6 . C17 . 1.401(3) yes
C7 . C8 . 1.427(3) yes
C7 . C14 . 1.419(3) yes
C8 . C9 . 1.427(3) yes
C9 . C10 . 1.398(3) yes
C9 . C12 . 1.439(3) yes
C10 . C11 . 1.394(3) yes
C10 . H101 . 1.00(3) no
C11 . H111 . 1.04(3) no
C12 . C13 . 1.346(3) yes
C12 . H121 . 0.98(3) no
C13 . C14 . 1.442(3) yes
C13 . H131 . 1.03(3) no
C14 . C15 . 1.394(3) yes
C15 . C16 . 1.385(4) yes
C15 . H151 . 0.97(3) no
C16 . C17 . 1.386(3) yes
C16 . H161 . 0.96(4) no
C17 . H171 . 1.02(3) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 . N1 . C1 . 121.49(18) yes
C18 . N1 . H1 . 118.6(11) no
C1 . N1 . H1 . 119.6(11) no
N1 . C18 . N1 6_655 115.6(3) yes
N1 . C18 . O3 . 122.21(13) yes
N1 6_655 C18 . O3 . 122.21(13) yes
N1 . C1 . C2 . 110.83(17) yes
N1 . C1 . H11 . 110.7(14) no
C2 . C1 . H11 . 109.3(14) no
N1 . C1 . H12 . 105.8(13) no
C2 . C1 . H12 . 113.4(13) no
H11 . C1 . H12 . 106.6(19) no
C1 . C2 . C3 . 121.3(2) yes
C1 . C2 . C11 . 119.6(2) yes
C3 . C2 . C11 . 119.0(2) yes
C2 . C3 . C4 . 122.36(19) yes
C2 . C3 . C8 . 119.7(2) yes
C4 . C3 . C8 . 117.9(2) yes
C3 . C4 . C5 . 121.5(2) yes
C3 . C4 . H41 . 120.1(14) no
C5 . C4 . H41 . 118.3(14) no
C4 . C5 . C6 . 121.7(2) yes
C4 . C5 . H51 . 117.2(18) no
C6 . C5 . H51 . 121.1(18) no
C5 . C6 . C7 . 118.5(2) yes
C5 . C6 . C17 . 122.8(2) yes
C7 . C6 . C17 . 118.8(2) yes
C6 . C7 . C8 . 120.0(2) yes
C6 . C7 . C14 . 119.7(2) yes
C8 . C7 . C14 . 120.3(2) yes
C7 . C8 . C3 . 120.4(2) yes
C7 . C8 . C9 . 119.5(2) yes
C3 . C8 . C9 . 120.1(2) yes
C8 . C9 . C10 . 118.9(2) yes
C8 . C9 . C12 . 118.8(2) yes
C10 . C9 . C12 . 122.4(2) yes
C9 . C10 . C11 . 120.4(2) yes
C9 . C10 . H101 . 119.6(17) no
C11 . C10 . H101 . 120.0(17) no
C10 . C11 . C2 . 121.9(2) yes
C10 . C11 . H111 . 118.9(16) no
C2 . C11 . H111 . 119.0(16) no
C9 . C12 . C13 . 121.5(2) yes
C9 . C12 . H121 . 115.9(18) no
C13 . C12 . H121 . 122.3(18) no
C12 . C13 . C14 . 121.2(2) yes
C12 . C13 . H131 . 121.1(15) no
C14 . C13 . H131 . 117.5(15) no
C13 . C14 . C7 . 118.7(2) yes
C13 . C14 . C15 . 121.7(2) yes
C7 . C14 . C15 . 119.6(2) yes
C14 . C15 . C16 . 120.5(2) yes
C14 . C15 . H151 . 117.0(18) no
C16 . C15 . H151 . 122.2(18) no
C15 . C16 . C17 . 120.7(2) yes
C15 . C16 . H161 . 118(2) no
C17 . C16 . H161 . 121(2) no
C6 . C17 . C16 . 120.8(2) yes
C6 . C17 . H171 . 119.4(18) no
C16 . C17 . H171 . 119.8(18) no


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
C18 N1 C1 C2 -168.05(17) . . . . no
C1 N1 C18 O3 3.3(2) . . . . no
N1 C1 C2 C3 67.9(3) . . . . no
N1 C1 C2 C11 -111.4(2) . . . . no
C1 C2 C3 C4 1.7(3) . . . . no
C1 C2 C3 C8 -178.5(2) . . . . no
C11 C2 C3 C4 -179.0(2) . . . . no
C11 C2 C3 C8 0.8(3) . . . . no
C1 C2 C11 C10 178.7(2) . . . . no
C3 C2 C11 C10 -0.7(4) . . . . no
C2 C3 C4 C5 -178.8(2) . . . . no
C8 C3 C4 C5 1.4(3) . . . . no
C2 C3 C8 C7 178.9(2) . . . . no
C2 C3 C8 C9 -0.2(3) . . . . no
C4 C3 C8 C7 -1.3(3) . . . . no
C4 C3 C8 C9 179.6(2) . . . . no
C3 C4 C5 C6 -0.4(4) . . . . no
C4 C5 C6 C7 -0.8(4) . . . . no
C4 C5 C6 C17 179.5(2) . . . . no
C5 C6 C7 C8 0.8(3) . . . . no
C5 C6 C7 C14 -179.6(2) . . . . no
C17 C6 C7 C8 -179.4(2) . . . . no
C17 C6 C7 C14 0.2(3) . . . . no
C5 C6 C17 C16 179.4(2) . . . . no
C7 C6 C17 C16 -0.3(4) . . . . no
C6 C7 C8 C3 0.2(3) . . . . no
C6 C7 C8 C9 179.3(2) . . . . no
C14 C7 C8 C3 -179.4(2) . . . . no
C14 C7 C8 C9 -0.3(3) . . . . no
C6 C7 C14 C13 -179.7(2) . . . . no
C6 C7 C14 C15 -0.1(3) . . . . no
C8 C7 C14 C13 0.0(3) . . . . no
C8 C7 C14 C15 179.5(2) . . . . no
C3 C8 C9 C10 -0.6(3) . . . . no
C3 C8 C9 C12 179.8(2) . . . . no
C7 C8 C9 C10 -179.7(2) . . . . no
C7 C8 C9 C12 0.7(3) . . . . no
C8 C9 C10 C11 0.7(4) . . . . no
C12 C9 C10 C11 -179.7(2) . . . . no
C8 C9 C12 C13 -0.7(4) . . . . no
C10 C9 C12 C13 179.7(2) . . . . no
C9 C10 C11 C2 -0.1(4) . . . . no
C9 C12 C13 C14 0.3(4) . . . . no
C12 C13 C14 C7 0.1(4) . . . . no
C12 C13 C14 C15 -179.5(2) . . . . no
C7 C14 C15 C16 0.1(4) . . . . no
C13 C14 C15 C16 179.6(2) . . . . no
C14 C15 C16 C17 -0.2(4) . . . . no
C15 C16 C17 C6 0.3(4) . . . . no

# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
