# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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 
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data_Cu_complex_1
_database_code_depnum_ccdc_archive 'CCDC 2224182'
loop_
_audit_author_name
_audit_author_address
'Jitendra Bera'
;Indian Institute of Technology Kanpur
India
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_audit_creation_date             2022-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H40 Cu2 N8 O2, 2(F6 P), C H2 Cl2'
_chemical_formula_sum            'C37 H42 Cl2 Cu2 F12 N8 O2 P2'
_chemical_formula_weight         1118.70
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_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                   11.0140(10)
_cell_length_b                   14.2677(14)
_cell_length_c                   15.3705(14)
_cell_angle_alpha                84.990(3)
_cell_angle_beta                 75.303(2)
_cell_angle_gamma                67.883(2)
_cell_volume                     2164.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.278
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.999
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            42273
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_min         2.730
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                8433
_reflns_number_total             10715
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         10715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+7.7184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C14(H14A,H14B), C36(H36A,H36B), C32(H32A,
 H32B), C33(H33A,H33B), C18(H18A,H18B), C34(H34A,H34B), C35(H35A,H35B),
 C31(H31A,H31B), C17(H17A,H17B), C16(H16A,H16B), C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C3(H3), C22(H22), C12(H12), C27(H27), C6(H6), C29(H29), C30(H30),
 C24(H24), C11(H11), C23(H23), C28(H28), C9(H9), C5(H5), C10(H10), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cu2 Cu 0.02236(4) 0.77902(3) 0.79110(3) 0.01446(10) Uani 1 1 d . . . . .
Cu1 Cu 0.23569(4) 0.75231(3) 0.68814(3) 0.01595(10) Uani 1 1 d . . . . .
P1 P 0.42004(10) 0.14905(7) 0.76988(6) 0.01897(19) Uani 1 1 d . . . . .
P2 P 0.68980(10) 0.57974(8) 0.71929(7) 0.0225(2) Uani 1 1 d . . . . .
Cl1 Cl 0.15677(11) 0.82897(8) 0.34183(7) 0.0327(2) Uani 1 1 d . . . . .
Cl2 Cl 0.04154(13) 0.79808(10) 0.19987(8) 0.0408(3) Uani 1 1 d . . . . .
F1 F 0.4714(3) 0.08333(19) 0.67865(16) 0.0312(6) Uani 1 1 d . . . . .
F4 F 0.3690(2) 0.21300(18) 0.86160(16) 0.0295(5) Uani 1 1 d . . . . .
F2 F 0.4242(2) 0.04912(18) 0.82767(16) 0.0283(5) Uani 1 1 d . . . . .
F6 F 0.2677(2) 0.1701(2) 0.76875(16) 0.0349(6) Uani 1 1 d . . . . .
F3 F 0.5727(2) 0.12673(19) 0.77121(18) 0.0314(5) Uani 1 1 d . . . . .
F5 F 0.4154(3) 0.24818(19) 0.71240(18) 0.0380(6) Uani 1 1 d . . . . .
O2 O 0.2408(3) 0.9275(2) 0.47753(19) 0.0297(6) Uani 1 1 d . . . . .
O1 O -0.1462(3) 0.9571(2) 1.01983(18) 0.0269(6) Uani 1 1 d . . . . .
N6 N 0.0521(3) 0.6885(2) 0.60964(19) 0.0152(6) Uani 1 1 d . . . . .
F11 F 0.6875(3) 0.4790(2) 0.6840(3) 0.0535(9) Uani 1 1 d . . . . .
N3 N 0.2593(3) 0.8062(2) 0.8572(2) 0.0185(6) Uani 1 1 d . . . . .
N7 N -0.1243(3) 0.8237(2) 0.65138(19) 0.0157(6) Uani 1 1 d . . . . .
N2 N 0.2135(3) 0.6696(2) 0.88744(19) 0.0166(6) Uani 1 1 d . . . . .
N4 N 0.3030(3) 0.8658(2) 0.6504(2) 0.0171(6) Uani 1 1 d . . . . .
N5 N 0.2707(3) 0.6214(2) 0.6343(2) 0.0173(6) Uani 1 1 d . . . . .
N8 N -0.1693(3) 0.8828(2) 0.85779(19) 0.0158(6) Uani 1 1 d . . . . .
N1 N 0.0388(3) 0.6378(2) 0.8559(2) 0.0186(6) Uani 1 1 d . . . . .
F12 F 0.8462(3) 0.5463(3) 0.6747(2) 0.0586(9) Uani 1 1 d . . . . .
F8 F 0.6942(4) 0.6809(2) 0.7505(3) 0.0667(11) Uani 1 1 d . . . . .
F9 F 0.5326(3) 0.6169(3) 0.7612(2) 0.0751(13) Uani 1 1 d . . . . .
F10 F 0.6572(4) 0.6316(3) 0.6284(2) 0.0724(12) Uani 1 1 d . . . . .
C1 C 0.1874(4) 0.7563(3) 0.8349(2) 0.0168(7) Uani 1 1 d . . . . .
F7 F 0.7213(5) 0.5292(4) 0.8092(3) 0.0901(16) Uani 1 1 d . . . . .
C26 C 0.1732(4) 0.6035(3) 0.6098(2) 0.0159(7) Uani 1 1 d . . . . .
C19 C -0.0124(4) 0.7619(3) 0.6760(2) 0.0161(7) Uani 1 1 d . . . . .
C8 C 0.1535(4) 0.5987(3) 0.8830(2) 0.0181(7) Uani 1 1 d . . . . .
C20 C -0.0203(4) 0.7057(3) 0.5429(2) 0.0166(7) Uani 1 1 d . . . . .
C13 C 0.2720(4) 0.8984(3) 0.8139(2) 0.0219(8) Uani 1 1 d . . . . .
H13A H 0.304989 0.929563 0.851744 0.026 Uiso 1 1 calc R . . . .
H13B H 0.183196 0.945333 0.809826 0.026 Uiso 1 1 calc R . . . .
C15 C 0.1908(4) 0.9613(3) 0.6374(3) 0.0229(8) Uani 1 1 d . . . . .
H15A H 0.223084 1.016818 0.627742 0.028 Uiso 1 1 calc R . . . .
H15B H 0.118010 0.976193 0.691337 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3259(4) 0.7557(3) 0.9233(2) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.2938(4) 0.6694(3) 0.9447(2) 0.0195(7) Uani 1 1 d . . . . .
C25 C 0.0051(4) 0.6569(3) 0.4619(2) 0.0204(7) Uani 1 1 d . . . . .
H25 H 0.081158 0.599028 0.442991 0.024 Uiso 1 1 calc R . . . .
C21 C -0.1334(4) 0.7927(3) 0.5702(2) 0.0166(7) Uani 1 1 d . . . . .
C14 C 0.3657(4) 0.8819(3) 0.7206(2) 0.0207(7) Uani 1 1 d . . . . .
H14A H 0.391393 0.940271 0.704639 0.025 Uiso 1 1 calc R . . . .
H14B H 0.447067 0.823442 0.721435 0.025 Uiso 1 1 calc R . . . .
C36 C -0.2147(4) 0.8466(3) 0.9493(2) 0.0205(7) Uani 1 1 d . . . . .
H36A H -0.205393 0.776568 0.945794 0.025 Uiso 1 1 calc R . . . .
H36B H -0.309231 0.886387 0.973557 0.025 Uiso 1 1 calc R . . . .
C3 C 0.3367(4) 0.6051(3) 1.0138(3) 0.0247(8) Uani 1 1 d . . . . .
H3 H 0.314224 0.548215 1.029175 0.030 Uiso 1 1 calc R . . . .
C22 C -0.2289(4) 0.8342(3) 0.5193(3) 0.0212(7) Uani 1 1 d . . . . .
H22 H -0.305136 0.891966 0.538103 0.025 Uiso 1 1 calc R . . . .
C32 C -0.2653(4) 0.8835(3) 0.8050(2) 0.0191(7) Uani 1 1 d . . . . .
H32A H -0.353835 0.931914 0.832375 0.023 Uiso 1 1 calc R . . . .
H32B H -0.271722 0.817210 0.809056 0.023 Uiso 1 1 calc R . . . .
C12 C -0.0229(4) 0.5751(3) 0.8464(3) 0.0232(8) Uani 1 1 d . . . . .
H12 H -0.102513 0.601690 0.826954 0.028 Uiso 1 1 calc R . . . .
C27 C 0.1862(4) 0.5085(3) 0.5852(3) 0.0203(7) Uani 1 1 d . . . . .
H27 H 0.115573 0.498439 0.569822 0.024 Uiso 1 1 calc R . . . .
C6 C 0.4055(4) 0.7808(3) 0.9673(3) 0.0269(9) Uani 1 1 d . . . . .
H6 H 0.428064 0.837732 0.952304 0.032 Uiso 1 1 calc R . . . .
C29 C 0.4089(4) 0.4463(3) 0.6088(3) 0.0259(8) Uani 1 1 d . . . . .
H29 H 0.490804 0.393683 0.608384 0.031 Uiso 1 1 calc R . . . .
C33 C -0.1783(4) 0.9884(3) 0.8676(3) 0.0203(7) Uani 1 1 d . . . . .
H33A H -0.272187 1.031978 0.888532 0.024 Uiso 1 1 calc R . . . .
H33B H -0.142949 1.012710 0.809506 0.024 Uiso 1 1 calc R . . . .
C18 C 0.4072(4) 0.8419(3) 0.5635(3) 0.0239(8) Uani 1 1 d . . . . .
H18A H 0.479852 0.778379 0.568512 0.029 Uiso 1 1 calc R . . . .
H18B H 0.444849 0.894524 0.550100 0.029 Uiso 1 1 calc R . . . .
C34 C -0.0997(4) 0.9940(3) 0.9335(3) 0.0242(8) Uani 1 1 d . . . . .
H34A H -0.004787 0.954309 0.910380 0.029 Uiso 1 1 calc R . . . .
H34B H -0.108907 1.063652 0.939335 0.029 Uiso 1 1 calc R . . . .
C35 C -0.1324(4) 0.8551(3) 1.0114(3) 0.0253(8) Uani 1 1 d . . . . .
H35A H -0.162153 0.829505 1.070245 0.030 Uiso 1 1 calc R . . . .
H35B H -0.038037 0.814121 0.987860 0.030 Uiso 1 1 calc R . . . .
C30 C 0.3874(4) 0.5427(3) 0.6339(3) 0.0227(8) Uani 1 1 d . . . . .
H30 H 0.455788 0.553949 0.651306 0.027 Uiso 1 1 calc R . . . .
C31 C -0.2283(4) 0.9096(3) 0.7059(2) 0.0199(7) Uani 1 1 d . . . . .
H31A H -0.308572 0.932406 0.682599 0.024 Uiso 1 1 calc R . . . .
H31B H -0.196023 0.964924 0.700559 0.024 Uiso 1 1 calc R . . . .
C24 C -0.0898(4) 0.6997(3) 0.4112(2) 0.0243(8) Uani 1 1 d . . . . .
H24 H -0.076063 0.670048 0.356245 0.029 Uiso 1 1 calc R . . . .
C17 C 0.3455(4) 0.8344(3) 0.4881(3) 0.0269(8) Uani 1 1 d . . . . .
H17A H 0.414885 0.816924 0.432349 0.032 Uiso 1 1 calc R . . . .
H17B H 0.309210 0.781042 0.501155 0.032 Uiso 1 1 calc R . . . .
C11 C 0.0273(5) 0.4725(3) 0.8645(3) 0.0293(9) Uani 1 1 d . . . . .
H11 H -0.018174 0.431072 0.858468 0.035 Uiso 1 1 calc R . . . .
C23 C -0.2050(4) 0.7855(3) 0.4395(3) 0.0239(8) Uani 1 1 d . . . . .
H23 H -0.266947 0.810467 0.403870 0.029 Uiso 1 1 calc R . . . .
C28 C 0.3068(4) 0.4289(3) 0.5842(3) 0.0262(8) Uani 1 1 d . . . . .
H28 H 0.319189 0.364428 0.567048 0.031 Uiso 1 1 calc R . . . .
C9 C 0.2126(4) 0.4959(3) 0.9006(3) 0.0273(9) Uani 1 1 d . . . . .
H9 H 0.293976 0.470291 0.917926 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4494(4) 0.7153(4) 1.0355(3) 0.0348(11) Uani 1 1 d . . . . .
H5 H 0.503436 0.728618 1.066693 0.042 Uiso 1 1 calc R . . . .
C10 C 0.1464(5) 0.4339(3) 0.8916(3) 0.0331(10) Uani 1 1 d . . . . .
H10 H 0.182551 0.365272 0.903950 0.040 Uiso 1 1 calc R . . . .
C4 C 0.4143(4) 0.6309(4) 1.0580(3) 0.0345(10) Uani 1 1 d . . . . .
H4 H 0.444388 0.590102 1.104672 0.041 Uiso 1 1 calc R . . . .
C16 C 0.1381(4) 0.9527(3) 0.5583(3) 0.0282(9) Uani 1 1 d . . . . .
H16A H 0.098431 0.901199 0.570560 0.034 Uiso 1 1 calc R . . . .
H16B H 0.067588 1.016513 0.550714 0.034 Uiso 1 1 calc R . . . .
C37 C 0.1826(5) 0.7557(4) 0.2482(3) 0.0360(10) Uani 1 1 d . . . . .
H37A H 0.200897 0.685831 0.266401 0.043 Uiso 1 1 calc R . . . .
H37B H 0.261119 0.758180 0.203357 0.043 Uiso 1 1 calc R . . . .


_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
Cu2 Cu1 2.3905(6) . ?
Cu2 N8 2.124(3) . ?
Cu2 N1 2.133(3) . ?
Cu2 C1 2.001(4) . ?
Cu2 C19 1.955(3) . ?
Cu1 N4 2.008(3) . ?
Cu1 N5 1.973(3) . ?
Cu1 C1 2.183(3) . ?
P1 F1 1.610(2) . ?
P1 F4 1.604(2) . ?
P1 F2 1.604(2) . ?
P1 F6 1.594(2) . ?
P1 F3 1.595(2) . ?
P1 F5 1.592(3) . ?
P2 F11 1.591(3) . ?
P2 F12 1.582(3) . ?
P2 F8 1.581(3) . ?
P2 F9 1.579(3) . ?
P2 F10 1.582(3) . ?
P2 F7 1.560(3) . ?
Cl1 C37 1.753(5) . ?
Cl2 C37 1.770(5) . ?
O2 C17 1.423(5) . ?
O2 C16 1.418(5) . ?
O1 C34 1.427(5) . ?
O1 C35 1.419(5) . ?
N6 C26 1.425(4) . ?
N6 C19 1.379(4) . ?
N6 C20 1.405(4) . ?
N3 C1 1.362(4) . ?
N3 C13 1.460(5) . ?
N3 C7 1.393(5) . ?
N7 C19 1.341(4) . ?
N7 C21 1.399(4) . ?
N7 C31 1.467(4) . ?
N2 C1 1.393(4) . ?
N2 C8 1.416(5) . ?
N2 C2 1.396(4) . ?
N4 C15 1.494(5) . ?
N4 C14 1.495(5) . ?
N4 C18 1.491(5) . ?
N5 C26 1.336(4) . ?
N5 C30 1.351(5) . ?
N8 C36 1.486(4) . ?
N8 C32 1.484(4) . ?
N8 C33 1.491(4) . ?
N1 C8 1.333(5) . ?
N1 C12 1.347(5) . ?
C26 C27 1.385(5) . ?
C8 C9 1.395(5) . ?
C20 C25 1.393(5) . ?
C20 C21 1.389(5) . ?
C13 C14 1.518(5) . ?
C15 C16 1.505(6) . ?
C7 C2 1.395(6) . ?
C7 C6 1.391(5) . ?
C2 C3 1.398(5) . ?
C25 C24 1.387(5) . ?
C21 C22 1.392(5) . ?
C36 C35 1.513(5) . ?
C3 C4 1.379(6) . ?
C22 C23 1.379(5) . ?
C32 C31 1.525(5) . ?
C12 C11 1.387(5) . ?
C27 C28 1.382(5) . ?
C6 C5 1.397(6) . ?
C29 C30 1.378(5) . ?
C29 C28 1.382(6) . ?
C33 C34 1.513(5) . ?
C18 C17 1.515(6) . ?
C24 C23 1.393(6) . ?
C11 C10 1.376(6) . ?
C9 C10 1.376(6) . ?
C5 C4 1.390(7) . ?

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
N8 Cu2 Cu1 148.14(8) . . ?
N8 Cu2 N1 105.12(12) . . ?
N1 Cu2 Cu1 106.22(9) . . ?
C1 Cu2 Cu1 58.83(10) . . ?
C1 Cu2 N8 120.93(13) . . ?
C1 Cu2 N1 82.00(13) . . ?
C19 Cu2 Cu1 77.35(10) . . ?
C19 Cu2 N8 100.95(13) . . ?
C19 Cu2 N1 103.21(13) . . ?
C19 Cu2 C1 135.15(14) . . ?
N4 Cu1 Cu2 121.70(9) . . ?
N4 Cu1 C1 104.54(13) . . ?
N5 Cu1 Cu2 100.48(9) . . ?
N5 Cu1 N4 134.59(12) . . ?
N5 Cu1 C1 115.27(13) . . ?
C1 Cu1 Cu2 51.64(9) . . ?
F4 P1 F1 179.14(14) . . ?
F4 P1 F2 89.37(13) . . ?
F2 P1 F1 89.77(14) . . ?
F6 P1 F1 89.80(14) . . ?
F6 P1 F4 90.20(14) . . ?
F6 P1 F2 89.27(14) . . ?
F6 P1 F3 179.37(16) . . ?
F3 P1 F1 89.95(14) . . ?
F3 P1 F4 90.04(14) . . ?
F3 P1 F2 90.15(13) . . ?
F5 P1 F1 90.14(14) . . ?
F5 P1 F4 90.71(14) . . ?
F5 P1 F2 179.77(16) . . ?
F5 P1 F6 90.52(15) . . ?
F5 P1 F3 90.07(15) . . ?
F12 P2 F11 90.86(17) . . ?
F8 P2 F11 177.8(2) . . ?
F8 P2 F12 87.96(19) . . ?
F8 P2 F10 90.2(2) . . ?
F9 P2 F11 90.19(18) . . ?
F9 P2 F12 177.7(3) . . ?
F9 P2 F8 90.9(2) . . ?
F9 P2 F10 87.9(2) . . ?
F10 P2 F11 88.0(2) . . ?
F10 P2 F12 90.1(2) . . ?
F7 P2 F11 92.2(2) . . ?
F7 P2 F12 90.2(2) . . ?
F7 P2 F8 89.6(2) . . ?
F7 P2 F9 91.9(2) . . ?
F7 P2 F10 179.7(3) . . ?
C16 O2 C17 109.8(3) . . ?
C35 O1 C34 109.4(3) . . ?
C19 N6 C26 125.0(3) . . ?
C19 N6 C20 111.1(3) . . ?
C20 N6 C26 123.9(3) . . ?
C1 N3 C13 124.5(3) . . ?
C1 N3 C7 111.9(3) . . ?
C7 N3 C13 123.5(3) . . ?
C19 N7 C21 111.8(3) . . ?
C19 N7 C31 123.9(3) . . ?
C21 N7 C31 124.2(3) . . ?
C1 N2 C8 120.5(3) . . ?
C1 N2 C2 111.3(3) . . ?
C2 N2 C8 128.1(3) . . ?
C15 N4 Cu1 111.1(2) . . ?
C15 N4 C14 109.8(3) . . ?
C14 N4 Cu1 109.1(2) . . ?
C18 N4 Cu1 111.3(2) . . ?
C18 N4 C15 107.3(3) . . ?
C18 N4 C14 108.1(3) . . ?
C26 N5 Cu1 121.1(2) . . ?
C26 N5 C30 118.0(3) . . ?
C30 N5 Cu1 120.2(3) . . ?
C36 N8 Cu2 110.7(2) . . ?
C36 N8 C33 107.3(3) . . ?
C32 N8 Cu2 106.1(2) . . ?
C32 N8 C36 107.1(3) . . ?
C32 N8 C33 109.3(3) . . ?
C33 N8 Cu2 116.1(2) . . ?
C8 N1 Cu2 110.3(2) . . ?
C8 N1 C12 118.1(3) . . ?
C12 N1 Cu2 127.8(3) . . ?
Cu2 C1 Cu1 69.53(11) . . ?
N3 C1 Cu2 142.3(3) . . ?
N3 C1 Cu1 105.9(2) . . ?
N3 C1 N2 104.3(3) . . ?
N2 C1 Cu2 109.1(2) . . ?
N2 C1 Cu1 123.2(2) . . ?
N5 C26 N6 116.5(3) . . ?
N5 C26 C27 123.1(3) . . ?
C27 C26 N6 120.4(3) . . ?
N6 C19 Cu2 133.0(3) . . ?
N7 C19 Cu2 121.6(3) . . ?
N7 C19 N6 105.1(3) . . ?
N1 C8 N2 113.9(3) . . ?
N1 C8 C9 122.8(4) . . ?
C9 C8 N2 123.2(3) . . ?
C25 C20 N6 132.9(3) . . ?
C21 C20 N6 105.4(3) . . ?
C21 C20 C25 121.6(3) . . ?
N3 C13 C14 114.3(3) . . ?
N4 C15 C16 111.4(3) . . ?
N3 C7 C2 106.6(3) . . ?
C6 C7 N3 131.1(4) . . ?
C6 C7 C2 122.2(4) . . ?
N2 C2 C3 132.7(4) . . ?
C7 C2 N2 105.8(3) . . ?
C7 C2 C3 121.5(4) . . ?
C24 C25 C20 116.0(4) . . ?
C20 C21 N7 106.6(3) . . ?
C20 C21 C22 121.9(3) . . ?
C22 C21 N7 131.6(3) . . ?
N4 C14 C13 112.9(3) . . ?
N8 C36 C35 110.9(3) . . ?
C4 C3 C2 116.2(4) . . ?
C23 C22 C21 116.7(4) . . ?
N8 C32 C31 115.0(3) . . ?
N1 C12 C11 122.7(4) . . ?
C28 C27 C26 118.3(3) . . ?
C7 C6 C5 115.9(4) . . ?
C30 C29 C28 119.0(4) . . ?
N8 C33 C34 111.2(3) . . ?
N4 C18 C17 110.3(3) . . ?
O1 C34 C33 111.6(3) . . ?
O1 C35 C36 110.9(3) . . ?
N5 C30 C29 122.4(4) . . ?
N7 C31 C32 112.8(3) . . ?
C25 C24 C23 122.5(3) . . ?
O2 C17 C18 110.9(3) . . ?
C10 C11 C12 118.0(4) . . ?
C22 C23 C24 121.3(4) . . ?
C29 C28 C27 119.3(4) . . ?
C10 C9 C8 117.8(4) . . ?
C4 C5 C6 121.7(4) . . ?
C11 C10 C9 120.5(4) . . ?
C3 C4 C5 122.6(4) . . ?
O2 C16 C15 112.2(3) . . ?
Cl1 C37 Cl2 112.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dihydroacridine_3_29
_database_code_depnum_ccdc_archive 'CCDC 2224184'
loop_
_audit_author_name
_audit_author_address
'Jitendra Bera'
;Indian Institute of Technology Kanpur
India
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_audit_creation_date             2022-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H28 N2'
_chemical_formula_sum            'C34 H28 N2'
_chemical_formula_weight         464.58
_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'

_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      triclinic
_space_group_IT_number           2
_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                   10.7845(13)
_cell_length_b                   11.1594(14)
_cell_length_c                   11.3909(14)
_cell_angle_alpha                72.040(4)
_cell_angle_beta                 88.325(4)
_cell_angle_gamma                68.640(3)
_cell_volume                     1209.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9117
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19422
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.905
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                5127
_reflns_number_total             5993
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.025
_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)+(0.0462P)²+0.7851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C20(H20), C18(H18), C26(H26), C23(H23), C3(H3), C2(H2A),
 C17(H17), C13(H13), C24(H24), C29(H29), C16(H16), C5(H5), C25(H25), C30(H30),
 C4(H4), C32(H32), C10(H10), C11(H11), C12(H12), C31(H31)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.25861(12) 0.71065(11) 0.97710(10) 0.0160(2) Uani 1 1 d . . . . .
H2 H 0.209587 0.714614 1.037777 0.019 Uiso 1 1 calc R . . . .
N1 N 1.01050(11) 0.52056(12) 0.80791(11) 0.0184(2) Uani 1 1 d . . . . .
H1 H 1.091446 0.494060 0.838881 0.022 Uiso 1 1 calc R . . . .
C20 C 0.54971(13) 0.69581(12) 0.66082(12) 0.0131(2) Uani 1 1 d . . . . .
H20 H 0.576283 0.683566 0.741998 0.016 Uiso 1 1 calc R . . . .
C27 C 0.29535(12) 0.59822(13) 0.93592(12) 0.0133(2) Uani 1 1 d . . . . .
C22 C 0.32979(12) 0.61034(13) 0.81441(12) 0.0134(2) Uani 1 1 d . . . . .
C1 C 0.92292(13) 0.65304(13) 0.79229(12) 0.0151(3) Uani 1 1 d . . . . .
C18 C 0.37627(13) 0.74648(13) 0.50601(12) 0.0163(3) Uani 1 1 d . . . . .
H18 H 0.286584 0.771557 0.480962 0.020 Uiso 1 1 calc R . . . .
C28 C 0.30137(12) 0.81669(13) 0.91987(12) 0.0139(2) Uani 1 1 d . . . . .
C15 C 0.64679(13) 0.67637(13) 0.57745(12) 0.0137(2) Uani 1 1 d . . . . .
C19 C 0.41437(13) 0.73290(12) 0.62694(12) 0.0133(2) Uani 1 1 d . . . . .
C21 C 0.31361(12) 0.75080(13) 0.72401(12) 0.0131(2) Uani 1 1 d . . . . .
C14 C 0.96902(13) 0.43050(13) 0.77417(12) 0.0153(3) Uani 1 1 d . . . . .
C26 C 0.29623(13) 0.47472(13) 1.01600(12) 0.0156(3) Uani 1 1 d . . . . .
H26 H 0.270064 0.468996 1.095433 0.019 Uiso 1 1 calc R . . . .
C23 C 0.36946(14) 0.49418(14) 0.77811(13) 0.0177(3) Uani 1 1 d . . . . .
H23 H 0.393856 0.499886 0.698164 0.021 Uiso 1 1 calc R . . . .
C3 C 0.86357(14) 0.85886(14) 0.84604(13) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.880219 0.906674 0.893639 0.023 Uiso 1 1 calc R . . . .
C2 C 0.94640(13) 0.72492(14) 0.86487(13) 0.0174(3) Uani 1 1 d . . . . .
H2A H 1.017875 0.682579 0.925956 0.021 Uiso 1 1 calc R . . . .
C9 C 0.85506(13) 0.48125(13) 0.69032(12) 0.0144(2) Uani 1 1 d . . . . .
C17 C 0.47214(14) 0.72258(14) 0.42292(12) 0.0182(3) Uani 1 1 d . . . . .
H17 H 0.446310 0.729134 0.343280 0.022 Uiso 1 1 calc R . . . .
C33 C 0.33490(12) 0.83762(13) 0.79723(12) 0.0142(2) Uani 1 1 d . . . . .
C7 C 0.79438(13) 0.63485(13) 0.62010(12) 0.0137(2) Uani 1 1 d . . . . .
C13 C 1.03977(13) 0.29077(14) 0.82437(13) 0.0176(3) Uani 1 1 d . . . . .
H13 H 1.117246 0.258456 0.877076 0.021 Uiso 1 1 calc R . . . .
C24 C 0.37340(14) 0.36996(14) 0.85872(13) 0.0197(3) Uani 1 1 d . . . . .
H24 H 0.401034 0.293687 0.832844 0.024 Uiso 1 1 calc R . . . .
C29 C 0.31094(13) 0.90052(13) 0.98587(13) 0.0176(3) Uani 1 1 d . . . . .
H29 H 0.288584 0.885404 1.067191 0.021 Uiso 1 1 calc R . . . .
C34 C 0.16764(13) 0.82244(14) 0.66387(13) 0.0184(3) Uani 1 1 d . . . . .
H34A H 0.146648 0.765534 0.625891 0.028 Uiso 1 1 calc GR . . . .
H34B H 0.157677 0.907201 0.602069 0.028 Uiso 1 1 calc GR . . . .
H34C H 0.108056 0.839019 0.726356 0.028 Uiso 1 1 calc GR . . . .
C6 C 0.81223(13) 0.71343(13) 0.70358(12) 0.0144(2) Uani 1 1 d . . . . .
C16 C 0.60606(13) 0.68904(13) 0.45753(12) 0.0169(3) Uani 1 1 d . . . . .
H16 H 0.668889 0.674947 0.400539 0.020 Uiso 1 1 calc R . . . .
C5 C 0.73084(13) 0.84880(13) 0.68609(13) 0.0178(3) Uani 1 1 d . . . . .
H5 H 0.658198 0.891369 0.626217 0.021 Uiso 1 1 calc R . . . .
C25 C 0.33571(14) 0.36051(13) 0.97835(13) 0.0180(3) Uani 1 1 d . . . . .
H25 H 0.337055 0.278231 1.032451 0.022 Uiso 1 1 calc R . . . .
C30 C 0.35366(14) 1.00592(14) 0.93010(14) 0.0201(3) Uani 1 1 d . . . . .
H30 H 0.360338 1.061441 0.974008 0.024 Uiso 1 1 calc R . . . .
C4 C 0.75578(14) 0.92164(14) 0.75614(14) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.700493 1.011814 0.742700 0.024 Uiso 1 1 calc R . . . .
C32 C 0.37598(14) 0.94558(14) 0.74320(13) 0.0190(3) Uani 1 1 d . . . . .
H32 H 0.396892 0.962582 0.661396 0.023 Uiso 1 1 calc R . . . .
C10 C 0.81022(14) 0.38815(14) 0.66566(13) 0.0178(3) Uani 1 1 d . . . . .
H10 H 0.732974 0.419951 0.612778 0.021 Uiso 1 1 calc R . . . .
C11 C 0.87864(15) 0.24830(14) 0.71855(13) 0.0207(3) Uani 1 1 d . . . . .
H11 H 0.846326 0.187927 0.701913 0.025 Uiso 1 1 calc R . . . .
C12 C 0.99553(14) 0.19975(14) 0.79633(13) 0.0203(3) Uani 1 1 d . . . . .
H12 H 1.043650 0.106823 0.829279 0.024 Uiso 1 1 calc R . . . .
C8 C 0.87764(14) 0.66434(14) 0.50903(13) 0.0192(3) Uani 1 1 d . . . . .
H8A H 0.877792 0.609717 0.458320 0.029 Uiso 1 1 calc GR . . . .
H8B H 0.967806 0.642889 0.539407 0.029 Uiso 1 1 calc GR . . . .
H8C H 0.838842 0.758658 0.460644 0.029 Uiso 1 1 calc GR . . . .
C31 C 0.38644(15) 1.02858(14) 0.80892(15) 0.0222(3) Uani 1 1 d . . . . .
H31 H 0.415417 1.099176 0.771410 0.027 Uiso 1 1 calc R . . . .


_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 H2 0.8600 . ?
N2 C27 1.3932(16) . ?
N2 C28 1.3936(16) . ?
N1 H1 0.8600 . ?
N1 C1 1.3927(17) . ?
N1 C14 1.3906(17) . ?
C20 H20 0.9300 . ?
C20 C15 1.3959(17) . ?
C20 C19 1.3946(17) . ?
C27 C22 1.4011(17) . ?
C27 C26 1.3955(18) . ?
C22 C21 1.5373(17) . ?
C22 C23 1.3967(18) . ?
C1 C2 1.4000(18) . ?
C1 C6 1.4017(19) . ?
C18 H18 0.9300 . ?
C18 C19 1.3959(18) . ?
C18 C17 1.3905(19) . ?
C28 C33 1.4027(18) . ?
C28 C29 1.3999(18) . ?
C15 C7 1.5340(18) . ?
C15 C16 1.3963(18) . ?
C19 C21 1.5334(17) . ?
C21 C33 1.5358(17) . ?
C21 C34 1.5476(18) . ?
C14 C9 1.4040(18) . ?
C14 C13 1.3962(18) . ?
C26 H26 0.9300 . ?
C26 C25 1.3860(18) . ?
C23 H23 0.9300 . ?
C23 C24 1.3932(19) . ?
C3 H3 0.9300 . ?
C3 C2 1.3852(19) . ?
C3 C4 1.387(2) . ?
C2 H2A 0.9300 . ?
C9 C7 1.5409(18) . ?
C9 C10 1.3950(18) . ?
C17 H17 0.9300 . ?
C17 C16 1.3892(19) . ?
C33 C32 1.3936(18) . ?
C7 C6 1.5357(18) . ?
C7 C8 1.5515(18) . ?
C13 H13 0.9300 . ?
C13 C12 1.3869(19) . ?
C24 H24 0.9300 . ?
C24 C25 1.3941(19) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(2) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C6 C5 1.3967(18) . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.3933(19) . ?
C25 H25 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.384(2) . ?
C4 H4 0.9300 . ?
C32 H32 0.9300 . ?
C32 C31 1.393(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3965(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(2) . ?
C12 H12 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C31 H31 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
C27 N2 H2 120.0 . . ?
C27 N2 C28 119.93(11) . . ?
C28 N2 H2 120.0 . . ?
C1 N1 H1 119.5 . . ?
C14 N1 H1 119.5 . . ?
C14 N1 C1 120.99(11) . . ?
C15 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C19 C20 C15 122.46(12) . . ?
N2 C27 C22 119.84(11) . . ?
N2 C27 C26 119.54(11) . . ?
C26 C27 C22 120.61(12) . . ?
C27 C22 C21 119.47(11) . . ?
C23 C22 C27 117.91(12) . . ?
C23 C22 C21 122.48(11) . . ?
N1 C1 C2 119.79(12) . . ?
N1 C1 C6 119.64(12) . . ?
C2 C1 C6 120.57(12) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.13(12) . . ?
N2 C28 C33 119.64(11) . . ?
N2 C28 C29 119.50(12) . . ?
C29 C28 C33 120.87(12) . . ?
C20 C15 C7 120.19(11) . . ?
C20 C15 C16 118.02(12) . . ?
C16 C15 C7 121.71(11) . . ?
C20 C19 C18 118.24(12) . . ?
C20 C19 C21 119.55(11) . . ?
C18 C19 C21 122.15(11) . . ?
C22 C21 C34 108.36(10) . . ?
C19 C21 C22 109.09(10) . . ?
C19 C21 C33 111.47(10) . . ?
C19 C21 C34 111.85(10) . . ?
C33 C21 C22 109.13(10) . . ?
C33 C21 C34 106.85(10) . . ?
N1 C14 C9 119.46(12) . . ?
N1 C14 C13 120.05(12) . . ?
C13 C14 C9 120.48(12) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 C27 120.66(12) . . ?
C25 C26 H26 119.7 . . ?
C22 C23 H23 119.2 . . ?
C24 C23 C22 121.61(12) . . ?
C24 C23 H23 119.2 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.97(13) . . ?
C4 C3 H3 120.0 . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.25(13) . . ?
C3 C2 H2A 119.9 . . ?
C14 C9 C7 118.71(11) . . ?
C10 C9 C14 118.01(12) . . ?
C10 C9 C7 122.96(12) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.74(12) . . ?
C16 C17 H17 119.6 . . ?
C28 C33 C21 119.67(11) . . ?
C32 C33 C28 117.74(12) . . ?
C32 C33 C21 122.35(12) . . ?
C15 C7 C9 109.67(10) . . ?
C15 C7 C6 111.95(10) . . ?
C15 C7 C8 111.84(11) . . ?
C9 C7 C8 107.63(10) . . ?
C6 C7 C9 109.53(10) . . ?
C6 C7 C8 106.07(10) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.58(13) . . ?
C12 C13 H13 119.7 . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.70(12) . . ?
C25 C24 H24 120.2 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.01(13) . . ?
C30 C29 H29 120.0 . . ?
C21 C34 H34A 109.5 . . ?
C21 C34 H34B 109.5 . . ?
C21 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C1 C6 C7 119.14(11) . . ?
C5 C6 C1 117.89(12) . . ?
C5 C6 C7 122.59(12) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.33(12) . . ?
C17 C16 H16 119.8 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.63(13) . . ?
C4 C5 H5 119.2 . . ?
C26 C25 C24 119.46(12) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 119.92(13) . . ?
C31 C30 H30 120.0 . . ?
C3 C4 C5 119.62(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C33 C32 H32 119.3 . . ?
C31 C32 C33 121.49(13) . . ?
C31 C32 H32 119.3 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.52(13) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.63(13) . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 119.62(13) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C30 C31 C32 119.95(13) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_dihydroacridine_3_13
_database_code_depnum_ccdc_archive 'CCDC 2224183'
loop_
_audit_author_name
_audit_author_address
'Jitendra Bera'
;Indian Institute of Technology Kanpur
India
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_audit_creation_date             2022-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Br N'
_chemical_formula_sum            'C21 H17 Br N'
_chemical_formula_weight         363.27
_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'
Br Br -0.2901 2.4595 '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'

_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   8.0166(4)
_cell_length_b                   13.4004(6)
_cell_length_c                   15.2143(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1634.41(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.025
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                1952
_reflns_number_total             2110
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0215
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+1.0790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0583
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H20 of C20
 At 1.2 times of:
  H18 of C18, H19 of C19, H12 of C12, H11 of C11, H9 of C9, H10 of C10
2. Others
 Fixed Sof: H20(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C12(H12), C11(H11), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Br1 Br 1.11395(2) 0.750000 0.24476(2) 0.01561(7) Uani 1 2 d S T P . .
N1 N 0.48235(19) 0.750000 0.54010(10) 0.0131(3) Uani 1 2 d S T P . .
C17 C 1.0074(2) 0.750000 0.35631(12) 0.0138(4) Uani 1 2 d S T P . .
C13 C 0.52555(16) 0.66110(10) 0.58364(8) 0.0130(2) Uani 1 1 d . . . . .
C7 C 0.7905(2) 0.750000 0.61733(12) 0.0140(4) Uani 1 2 d S T P . .
C14 C 0.8605(2) 0.750000 0.52238(13) 0.0130(4) Uani 1 2 d S T P . .
C19 C 0.89781(16) 0.83958(11) 0.47965(9) 0.0158(3) Uani 1 1 d . . . . .
H19 H 0.873176 0.899825 0.507081 0.019 Uiso 1 1 calc R . . . .
C8 C 0.67862(17) 0.65909(10) 0.62904(8) 0.0143(3) Uani 1 1 d . . . . .
C18 C 0.97134(16) 0.84018(10) 0.39653(9) 0.0153(3) Uani 1 1 d . . . . .
H18 H 0.995737 0.900158 0.368588 0.018 Uiso 1 1 calc R . . . .
C12 C 0.42133(17) 0.57758(10) 0.58411(9) 0.0166(3) Uani 1 1 d . . . . .
H12 H 0.321029 0.578734 0.553411 0.020 Uiso 1 1 calc R . . . .
C20 C 0.3389(3) 0.750000 0.48137(13) 0.0167(4) Uani 1 2 d S T P . .
H20 H 0.342(4) 0.692(3) 0.444(2) 0.025 Uiso 0.5 1 d R . . A -1
C11 C 0.46797(19) 0.49265(11) 0.63064(9) 0.0200(3) Uani 1 1 d . . . . .
H11 H 0.399594 0.436586 0.629970 0.024 Uiso 1 1 calc R . . . .
C21 C 0.9399(3) 0.750000 0.68035(13) 0.0219(4) Uani 1 2 d S T P . .
H21A H 1.010441 0.806057 0.667580 0.033 Uiso 0.5 1 calc GR . . B -1
H21B H 1.002118 0.689342 0.673059 0.033 Uiso 0.5 1 calc GR . . B -1
H21C H 0.900708 0.754601 0.739829 0.033 Uiso 0.5 1 calc GR . . B -1
C9 C 0.72032(18) 0.57430(11) 0.67711(9) 0.0186(3) Uani 1 1 d . . . . .
H9 H 0.819196 0.573120 0.709073 0.022 Uiso 1 1 calc R . . . .
C10 C 0.61576(18) 0.49106(12) 0.67800(10) 0.0210(3) Uani 1 1 d . . . . .
H10 H 0.645063 0.434746 0.710214 0.025 Uiso 1 1 calc R . . . .
H20A H 0.238(3) 0.750000 0.5141(16) 0.015(6) Uiso 1 2 d S T P . .


_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
Br1 C17 1.8999(18) . ?
N1 C13 1.4063(15) 7_575 ?
N1 C13 1.4063(15) . ?
N1 C20 1.456(2) . ?
C17 C18 1.3851(16) 7_575 ?
C17 C18 1.3851(16) . ?
C13 C8 1.4084(18) . ?
C13 C12 1.3966(18) . ?
C7 C14 1.550(3) . ?
C7 C8 1.5232(17) 7_575 ?
C7 C8 1.5232(17) . ?
C7 C21 1.534(3) . ?
C14 C19 1.3975(17) . ?
C14 C19 1.3974(17) 7_575 ?
C19 C18 1.3952(19) . ?
C8 C9 1.3920(18) . ?
C12 C11 1.3915(19) . ?
C11 C10 1.387(2) . ?
C9 C10 1.395(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
C13 N1 C13 115.79(15) 7_575 . ?
C13 N1 C20 118.91(8) . . ?
C13 N1 C20 118.91(8) 7_575 . ?
C18 C17 Br1 119.24(8) . . ?
C18 C17 Br1 119.24(8) 7_575 . ?
C18 C17 C18 121.50(17) 7_575 . ?
N1 C13 C8 117.50(12) . . ?
C12 C13 N1 122.27(12) . . ?
C12 C13 C8 120.22(12) . . ?
C8 C7 C14 108.80(10) 7_575 . ?
C8 C7 C14 108.80(10) . . ?
C8 C7 C8 106.22(15) . 7_575 ?
C8 C7 C21 112.74(10) 7_575 . ?
C8 C7 C21 112.74(10) . . ?
C21 C7 C14 107.43(15) . . ?
C19 C14 C7 120.73(9) . . ?
C19 C14 C7 120.73(9) 7_575 . ?
C19 C14 C19 118.41(18) 7_575 . ?
C18 C19 C14 121.13(14) . . ?
C13 C8 C7 116.13(12) . . ?
C9 C8 C13 118.85(13) . . ?
C9 C8 C7 124.95(13) . . ?
C17 C18 C19 118.92(13) . . ?
C11 C12 C13 119.82(13) . . ?
C10 C11 C12 120.42(14) . . ?
C8 C9 C10 120.88(13) . . ?
C11 C10 C9 119.73(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
