# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_25
_database_code_depnum_ccdc_archive 'CCDC 1855508'
loop_
_audit_author_name
_audit_author_address
'ElSayed Shalaby'
;X-Ray Crystallography Lab., Physics Division, National Research Centre
Egypt
;
_audit_update_record             
;
2018-07-12 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   26.930(3)
_cell_length_b                   12.9179(18)
_cell_length_c                   12.9500(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.491(3)
_cell_angle_gamma                90
_cell_volume                     4296.7(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C1 H1 Cl1 N1 O1 
# Dc =      1.70 Fooo =   1792.00 Mu =      9.67 M =    549.34
# Found Formula = C3.71 H3 Cl0.14 N0.29 O0.29 
# Dc =      1.33 FOOO =   1792.00 Mu =      2.04 M =    428.92

_chemical_formula_sum            'C26 H21 Cl1 N2 O2'
_chemical_formula_moiety         'C26 H21 Cl1 N2 O2'
_chemical_compound_source        ?
_chemical_formula_weight         428.90


_cell_measurement_reflns_used    1012
_cell_measurement_theta_min      2
_cell_measurement_theta_max      26
_cell_measurement_temperature    293

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.14
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    0.204

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   none
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      293
_diffrn_reflns_number            11327
_reflns_number_total             2861
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2861 
# Theoretical number of reflections is about 5747 


_diffrn_reflns_theta_min         1.765
_diffrn_reflns_theta_max         26.678
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        26.678
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -29
_reflns_limit_h_max              27
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   4.41
_oxford_diffrn_Wilson_scale      759.37

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

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.13


# 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>2.0\s(I)
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     0
_refine_ls_number_parameters     173
_oxford_refine_ls_R_factor_ref   0.0386
_refine_ls_wR_factor_ref         0.0771
_refine_ls_goodness_of_fit_ref   0.9493
_refine_ls_shift/su_max          0.0007524
_refine_ls_shift/su_mean         0.0000484


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2843
_refine_ls_R_factor_all          0.0787
_refine_ls_wR_factor_all         0.1038

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1790
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_gt          0.0771

# 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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 8.00 13.1 7.72 3.14 0.675 
;

# 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
O1 O 0.22803(8) 0.2156(2) 0.12978(18) 0.0674 1.0000 Uani . . . . . .
O2 O 0.16374(8) 0.28805(19) 0.49669(17) 0.0610 1.0000 Uani . . . . . .
N1 N 0.30443(9) 0.2330(2) 0.26555(19) 0.0477 1.0000 Uani D . . . . .
N2 N 0.23023(9) 0.3246(2) 0.26672(19) 0.0533 1.0000 Uani . . . . . .
C1 C 0.38112(11) 0.1287(3) 0.2955(2) 0.0481 1.0000 Uani . . . . . .
C2 C 0.41469(12) 0.0675(3) 0.2597(3) 0.0521 1.0000 Uani . . . . . .
C3 C 0.40317(12) 0.0450(3) 0.1511(3) 0.0488 1.0000 Uani . . . . . .
C4 C 0.35879(12) 0.0843(3) 0.0791(3) 0.0539 1.0000 Uani . . . . . .
C5 C 0.32515(12) 0.1464(3) 0.1142(2) 0.0518 1.0000 Uani . . . . . .
C6 C 0.33603(11) 0.1686(2) 0.2237(2) 0.0409 1.0000 Uani D . . . . .
C7 C 0.25314(12) 0.2561(3) 0.2154(2) 0.0461 1.0000 Uani D . . . . .
C8 C 0.25465(12) 0.3918(3) 0.3575(2) 0.0512 1.0000 Uani . . . . . .
C9 C 0.17457(11) 0.3423(3) 0.2251(2) 0.0533 1.0000 Uani . . . . . .
C10 C 0.05733(12) 0.3044(3) 0.0898(3) 0.0597 1.0000 Uani . . . . . .
C11 C 0.02031(15) 0.2819(3) -0.0076(3) 0.0782 1.0000 Uani . . . . . .
C12 C -0.00906(16) 0.1939(4) -0.0179(3) 0.0868 1.0000 Uani . . . . . .
C13 C -0.00206(16) 0.1271(4) 0.0678(4) 0.0850 1.0000 Uani . . . . . .
C14 C 0.03478(13) 0.1504(3) 0.1649(3) 0.0692 1.0000 Uani . . . . . .
C15 C 0.06569(12) 0.2388(3) 0.1780(3) 0.0521 1.0000 Uani . . . . . .
C16 C 0.10333(12) 0.2586(3) 0.2849(2) 0.0529 1.0000 Uani . . . . . .
C17 C 0.14954(12) 0.3065(3) 0.3078(2) 0.0459 1.0000 Uani . . . . . .
C18 C 0.18055(12) 0.3205(3) 0.4240(2) 0.0460 1.0000 Uani . . . . . .
C19 C 0.23095(11) 0.3772(2) 0.4485(2) 0.0447 1.0000 Uani . . . . . .
C20 C 0.25266(12) 0.4132(2) 0.5493(2) 0.0497 1.0000 Uani . . . . . .
C21 C 0.30002(13) 0.4734(3) 0.5952(2) 0.0508 1.0000 Uani . . . . . .
C22 C 0.32389(14) 0.4707(3) 0.7075(3) 0.0612 1.0000 Uani . . . . . .
C23 C 0.36831(16) 0.5268(3) 0.7551(3) 0.0775 1.0000 Uani . . . . . .
C24 C 0.39033(16) 0.5872(3) 0.6928(4) 0.0797 1.0000 Uani . . . . . .
C25 C 0.36730(17) 0.5931(3) 0.5835(3) 0.0818 1.0000 Uani . . . . . .
C26 C 0.32256(15) 0.5363(3) 0.5357(3) 0.0684 1.0000 Uani . . . . . .
Cl1 Cl 0.44468(3) -0.03383(8) 0.10479(8) 0.0694 1.0000 Uani . . . . . .
H21 H 0.4457 0.0408 0.3089 0.0655 1.0000 Uiso R . . . . .
H11 H 0.3888 0.1442 0.3704 0.0579 1.0000 Uiso R . . . . .
H91 H 0.1609 0.3041 0.1601 0.0654 1.0000 Uiso R . . . . .
H92 H 0.1678 0.4139 0.2108 0.0654 1.0000 Uiso R . . . . .
H81 H 0.2501 0.4617 0.3339 0.0612 1.0000 Uiso R . . . . .
H82 H 0.2908 0.3762 0.3829 0.0612 1.0000 Uiso R . . . . .
H201 H 0.2343 0.3958 0.5991 0.0612 1.0000 Uiso R . . . . .
H221 H 0.3090 0.4294 0.7511 0.0770 1.0000 Uiso R . . . . .
H231 H 0.3840 0.5242 0.8313 0.0872 1.0000 Uiso R . . . . .
H241 H 0.4216 0.6238 0.7265 0.0930 1.0000 Uiso R . . . . .
H251 H 0.3822 0.6355 0.5407 0.0984 1.0000 Uiso R . . . . .
H261 H 0.3064 0.5418 0.4598 0.0833 1.0000 Uiso R . . . . .
H161 H 0.0940 0.2340 0.3457 0.0610 1.0000 Uiso R . . . . .
H101 H 0.0777 0.3655 0.0974 0.0749 1.0000 Uiso R . . . . .
H111 H 0.0153 0.3271 -0.0677 0.0947 1.0000 Uiso R . . . . .
H121 H -0.0346 0.1789 -0.0848 0.1021 1.0000 Uiso R . . . . .
H131 H -0.0225 0.0660 0.0599 0.1020 1.0000 Uiso R . . . . .
H141 H 0.0401 0.1046 0.2246 0.0854 1.0000 Uiso R . . . . .
H51 H 0.2946 0.1739 0.0642 0.0635 1.0000 Uiso R . . . . .
H41 H 0.3514 0.0680 0.0045 0.0649 1.0000 Uiso R . . . . .
H262 H 0.3152(8) 0.242(2) 0.3343(14) 0.056(2) 1.0000 Uiso D . . . . .

_refine_ls_extinction_coef       45(5)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.064462(16)
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
O1 . C7 . 1.229(3) yes
O2 . C18 . 1.234(3) yes
N1 . C6 . 1.410(4) yes
N1 . C7 . 1.371(4) yes
N1 . H262 . 0.858(17) no
N2 . C7 . 1.361(4) yes
N2 . C8 . 1.450(4) yes
N2 . C9 . 1.451(4) yes
C1 . C2 . 1.381(4) yes
C1 . C6 . 1.388(4) yes
C1 . H11 . 0.950 no
C2 . C3 . 1.377(4) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.373(4) yes
C3 . Cl1 . 1.746(3) yes
C4 . C5 . 1.385(4) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.389(4) yes
C5 . H51 . 0.950 no
C8 . C19 . 1.512(4) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C9 . C17 . 1.500(4) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C10 . C11 . 1.383(5) yes
C10 . C15 . 1.386(5) yes
C10 . H101 . 0.950 no
C11 . C12 . 1.368(5) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.374(6) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.381(5) yes
C13 . H131 . 0.950 no
C14 . C15 . 1.393(5) yes
C14 . H141 . 0.950 no
C15 . C16 . 1.472(4) yes
C16 . C17 . 1.341(4) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.496(4) yes
C18 . C19 . 1.490(4) yes
C19 . C20 . 1.342(4) yes
C20 . C21 . 1.459(4) yes
C20 . H201 . 0.950 no
C21 . C22 . 1.403(4) yes
C21 . C26 . 1.380(5) yes
C22 . C23 . 1.376(5) yes
C22 . H221 . 0.950 no
C23 . C24 . 1.378(5) yes
C23 . H231 . 0.950 no
C24 . C25 . 1.366(5) yes
C24 . H241 . 0.950 no
C25 . C26 . 1.387(5) yes
C25 . H251 . 0.950 no
C26 . H261 . 0.950 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
C6 . N1 . C7 . 125.8(2) yes
C6 . N1 . H262 . 115.0(12) no
C7 . N1 . H262 . 116.2(12) no
C7 . N2 . C8 . 128.6(3) yes
C7 . N2 . C9 . 119.4(3) yes
C8 . N2 . C9 . 111.9(3) yes
C2 . C1 . C6 . 121.1(3) yes
C2 . C1 . H11 . 120.0 no
C6 . C1 . H11 . 118.9 no
C1 . C2 . C3 . 119.6(3) yes
C1 . C2 . H21 . 121.0 no
C3 . C2 . H21 . 119.4 no
C2 . C3 . C4 . 119.9(3) yes
C2 . C3 . Cl1 . 120.2(3) yes
C4 . C3 . Cl1 . 119.9(2) yes
C3 . C4 . C5 . 120.9(3) yes
C3 . C4 . H41 . 118.9 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . C6 . 119.7(3) yes
C4 . C5 . H51 . 120.8 no
C6 . C5 . H51 . 119.5 no
N1 . C6 . C5 . 123.2(3) yes
N1 . C6 . C1 . 118.0(3) yes
C5 . C6 . C1 . 118.8(3) yes
N1 . C7 . N2 . 116.8(3) yes
N1 . C7 . O1 . 122.5(3) yes
N2 . C7 . O1 . 120.7(3) yes
N2 . C8 . C19 . 111.3(3) yes
N2 . C8 . H81 . 109.0 no
C19 . C8 . H81 . 109.0 no
N2 . C8 . H82 . 108.8 no
C19 . C8 . H82 . 109.4 no
H81 . C8 . H82 . 109.5 no
N2 . C9 . C17 . 108.8(2) yes
N2 . C9 . H91 . 109.1 no
C17 . C9 . H91 . 109.6 no
N2 . C9 . H92 . 110.0 no
C17 . C9 . H92 . 109.8 no
H91 . C9 . H92 . 109.5 no
C11 . C10 . C15 . 121.2(4) yes
C11 . C10 . H101 . 120.4 no
C15 . C10 . H101 . 118.5 no
C10 . C11 . C12 . 120.0(4) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 119.8 no
C11 . C12 . C13 . 120.6(4) yes
C11 . C12 . H121 . 119.8 no
C13 . C12 . H121 . 119.6 no
C12 . C13 . C14 . 119.0(4) yes
C12 . C13 . H131 . 120.1 no
C14 . C13 . H131 . 120.9 no
C13 . C14 . C15 . 122.0(4) yes
C13 . C14 . H141 . 119.8 no
C15 . C14 . H141 . 118.2 no
C14 . C15 . C10 . 117.2(3) yes
C14 . C15 . C16 . 118.3(3) yes
C10 . C15 . C16 . 124.4(3) yes
C15 . C16 . C17 . 128.2(3) yes
C15 . C16 . H161 . 116.3 no
C17 . C16 . H161 . 115.5 no
C9 . C17 . C16 . 124.9(3) yes
C9 . C17 . C18 . 116.5(3) yes
C16 . C17 . C18 . 118.6(3) yes
C17 . C18 . O2 . 120.3(3) yes
C17 . C18 . C19 . 118.1(3) yes
O2 . C18 . C19 . 121.5(3) yes
C8 . C19 . C18 . 117.7(3) yes
C8 . C19 . C20 . 123.5(3) yes
C18 . C19 . C20 . 118.7(3) yes
C19 . C20 . C21 . 130.8(3) yes
C19 . C20 . H201 . 114.5 no
C21 . C20 . H201 . 114.7 no
C20 . C21 . C22 . 118.8(3) yes
C20 . C21 . C26 . 124.3(3) yes
C22 . C21 . C26 . 116.9(3) yes
C21 . C22 . C23 . 121.2(4) yes
C21 . C22 . H221 . 119.1 no
C23 . C22 . H221 . 119.7 no
C22 . C23 . C24 . 120.3(4) yes
C22 . C23 . H231 . 120.1 no
C24 . C23 . H231 . 119.6 no
C23 . C24 . C25 . 119.8(4) yes
C23 . C24 . H241 . 119.4 no
C25 . C24 . H241 . 120.8 no
C24 . C25 . C26 . 119.8(4) yes
C24 . C25 . H251 . 119.8 no
C26 . C25 . H251 . 120.4 no
C25 . C26 . C21 . 122.1(3) yes
C25 . C26 . H261 . 119.2 no
C21 . C26 . H261 . 118.7 no
####################################################################### 
# 
# 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_34
_database_code_depnum_ccdc_archive 'CCDC 1855509'
loop_
_audit_author_name
_audit_author_address
'ElSayed Shalaby'
;X-Ray Crystallography Lab., Physics Division, National Research Centre
Egypt
;
_audit_update_record             
;
2018-07-12 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   14.374(3)
_cell_length_b                   8.0590(16)
_cell_length_c                   18.554(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.61(3)
_cell_angle_gamma                90
_cell_volume                     2135.0(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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 0.0033 0.0016 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'
N 0.0061 0.0033 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 0.0106 0.0060 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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 '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'


_cell_formula_units_Z            4

# Given Formula = C44 H20 F2 N2 O2 
# Dc =      2.01 Fooo =   1328.00 Mu =      1.36 M =    646.65
# Found Formula = C26 H20 F2 N2 O2 
# Dc =      1.34 FOOO =    896.00 Mu =      0.97 M =    430.45

_chemical_formula_sum            'C26 H20 F2 N2 O2'
_chemical_formula_moiety         'C26 H20 F2 N2 O2'
_chemical_compound_source        ?
_chemical_formula_weight         430.45


_cell_measurement_reflns_used    1254
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30
_cell_measurement_temperature    293

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_max          0.07

_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.097

# Sheldrick geometric approximatio 1.00 1.00 
_exptl_absorpt_correction_type   none
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.70000
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      293
_diffrn_reflns_number            29314
_reflns_number_total             6693
_diffrn_reflns_av_R_equivalents  0.056
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6693 
# Theoretical number of reflections is about 14191 


_diffrn_reflns_theta_min         1.675
_diffrn_reflns_theta_max         30.961
_diffrn_measured_fraction_theta_max 0.943

_diffrn_reflns_theta_full        25.078
_diffrn_measured_fraction_theta_full 0.971


_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -21
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              27

_oxford_diffrn_Wilson_B_factor   4.95
_oxford_diffrn_Wilson_scale      0.08

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

_refine_diff_density_min         -0.41
_refine_diff_density_max         0.49


# 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>2.0\s(I)
_refine_ls_number_reflns         5048
_refine_ls_number_restraints     4
_refine_ls_number_parameters     294
_oxford_refine_ls_R_factor_ref   0.0636
_refine_ls_wR_factor_ref         0.1772
_refine_ls_goodness_of_fit_ref   0.9980
_refine_ls_shift/su_max          0.0038243
_refine_ls_shift/su_mean         0.0006897


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6677
_refine_ls_R_factor_all          0.0763
_refine_ls_wR_factor_all         0.1841

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5048
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_gt          0.1772

# 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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.219E+04 0.370E+04 0.224E+04 894. 193. 
;

# 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
O1 O 0.60775(8) 0.42423(17) 0.25103(6) 0.0737 1.0000 Uani . . . . . .
O2 O 0.64227(9) 0.60347(19) -0.05161(6) 0.0796 1.0000 Uani . . . . . .
N1 N 0.45760(9) 0.43629(18) 0.19598(6) 0.0639 1.0000 Uani D . . . . .
N2 N 0.57707(9) 0.57368(18) 0.14807(6) 0.0664 1.0000 Uani . . . . . .
C1 C 0.33775(11) 0.2482(2) 0.22233(11) 0.0737 1.0000 Uani . . . . . .
C2 C 0.29034(14) 0.1614(3) 0.27163(16) 0.0984 1.0000 Uani . . . . . .
C3 C 0.31759(19) 0.1716(4) 0.34383(17) 0.1140 1.0000 Uani . . . . . .
C4 C 0.39213(19) 0.2685(4) 0.36812(12) 0.1031 1.0000 Uani . . . . . .
C5 C 0.44174(14) 0.3569(3) 0.32134(9) 0.0761 1.0000 Uani . . . . . .
C6 C 0.41345(10) 0.34619(19) 0.24763(8) 0.0595 1.0000 Uani D . . . . .
C7 C 0.55072(10) 0.47616(18) 0.20290(6) 0.0567 1.0000 Uani D . . . . .
C8 C 0.51682(11) 0.6944(2) 0.10716(7) 0.0647 1.0000 Uani . . . . . .
C9 C 0.67593(11) 0.6100(2) 0.14849(8) 0.0662 1.0000 Uani . . . . . .
C10 C 0.88820(12) 0.5464(2) 0.17554(10) 0.0736 1.0000 Uani . . . . . .
C11 C 0.96286(14) 0.4847(3) 0.22037(14) 0.0920 1.0000 Uani . . . . . .
C12 C 1.01619(17) 0.3662(4) 0.1957(2) 0.1077 1.0000 Uani . . . . . .
C13 C 1.0030(2) 0.3083(4) 0.1271(3) 0.1306 1.0000 Uani . . . . . .
C14 C 0.92644(18) 0.3697(3) 0.08062(19) 0.1105 1.0000 Uani . . . . . .
C15 C 0.86674(12) 0.4870(2) 0.10476(10) 0.0701 1.0000 Uani . . . . . .
C16 C 0.78499(12) 0.5386(2) 0.05618(9) 0.0682 1.0000 Uani . . . . . .
C17 C 0.70191(10) 0.59292(18) 0.07255(7) 0.0593 1.0000 Uani . . . . . .
C18 C 0.62807(11) 0.6296(2) 0.01192(7) 0.0615 1.0000 Uani . . . . . .
C19 C 0.53798(10) 0.70012(17) 0.02949(7) 0.0581 1.0000 Uani . . . . . .
C20 C 0.48004(11) 0.76777(18) -0.02536(7) 0.0628 1.0000 Uani . . . . . .
C21 C 0.38956(12) 0.84879(19) -0.02612(8) 0.0652 1.0000 Uani . . . . . .
C22 C 0.33559(15) 0.8674(2) -0.09397(10) 0.0778 1.0000 Uani . . . . . .
C23 C 0.24880(16) 0.9415(3) -0.10088(12) 0.0887 1.0000 Uani . . . . . .
C24 C 0.21575(15) 0.9993(3) -0.03943(14) 0.0863 1.0000 Uani . . . . . .
C25 C 0.26559(16) 0.9877(3) 0.02838(12) 0.0834 1.0000 Uani . . . . . .
C26 C 0.35286(14) 0.9119(2) 0.03440(10) 0.0742 1.0000 Uani . . . . . .
H251 H 0.2396 1.0304 0.0694 0.1036 1.0000 Uiso R . . . . .
H261 H 0.3883 0.9029 0.0807 0.0897 1.0000 Uiso R . . . . .
H201 H 0.5028 0.7620 -0.0714 0.0761 1.0000 Uiso R . . . . .
H81 H 0.5273 0.8010 0.1284 0.0812 1.0000 Uiso R . . . . .
H82 H 0.4533 0.6634 0.1085 0.0812 1.0000 Uiso R . . . . .
H91 H 0.6881 0.7204 0.1649 0.0822 1.0000 Uiso R . . . . .
H92 H 0.7118 0.5348 0.1799 0.0822 1.0000 Uiso R . . . . .
H161 H 0.7915 0.5340 0.0058 0.0833 1.0000 Uiso R . . . . .
H101 H 0.8498 0.6301 0.1927 0.0922 1.0000 Uiso R . . . . .
H111 H 0.9780 0.5245 0.2685 0.1176 1.0000 Uiso R . . . . .
H131 H 1.0447 0.2289 0.1108 0.1497 1.0000 Uiso R . . . . .
H141 H 0.9146 0.3321 0.0319 0.1361 1.0000 Uiso R . . . . .
H11 H 0.3179 0.2431 0.1717 0.0916 1.0000 Uiso R . . . . .
H21 H 0.2383 0.0939 0.2544 0.1225 1.0000 Uiso R . . . . .
H31 H 0.2854 0.1115 0.3774 0.1353 1.0000 Uiso R . . . . .
H41 H 0.4109 0.2752 0.4188 0.1209 1.0000 Uiso R . . . . .
H51 H 0.4934 0.4250 0.3388 0.0936 1.0000 Uiso R . . . . .
H221 H 0.3597 0.8263 -0.1361 0.0955 1.0000 Uiso R . . . . .
H231 H 0.2126 0.9537 -0.1467 0.1068 1.0000 Uiso R . . . . .
F1 F 0.12986(10) 1.0720(2) -0.04436(11) 0.1192 1.0000 Uani . . . . . .
F2 F 1.08882(12) 0.3031(3) 0.24046(16) 0.1640 1.0000 Uani . . . . . .
H2 H 0.4258(11) 0.443(2) 0.1543(8) 0.0774(19) 1.0000 Uiso D . . . . .

_refine_ls_extinction_coef       730(30)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          5.33(16)
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
O1 . C7 . 1.2149(17) yes
O2 . C18 . 1.2372(18) yes
N1 . C6 . 1.4101(17) yes
N1 . C7 . 1.3682(19) yes
N1 . H2 . 0.854(15) no
N2 . C7 . 1.3730(16) yes
N2 . C8 . 1.457(2) yes
N2 . C9 . 1.4499(19) yes
C1 . C2 . 1.391(3) yes
C1 . C6 . 1.382(2) yes
C1 . H11 . 0.950 no
C2 . C3 . 1.354(4) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.360(4) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.383(3) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.384(2) yes
C5 . H51 . 0.950 no
C8 . C19 . 1.5074(19) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C9 . C17 . 1.505(2) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C10 . C11 . 1.373(3) yes
C10 . C15 . 1.398(3) yes
C10 . H101 . 0.950 no
C11 . C12 . 1.338(4) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.347(5) yes
C12 . F2 . 1.356(3) yes
C13 . C14 . 1.408(5) yes
C13 . H131 . 0.950 no
C14 . C15 . 1.385(3) yes
C14 . H141 . 0.950 no
C15 . C16 . 1.457(2) yes
C16 . C17 . 1.339(2) yes
C16 . H161 . 0.950 no
C17 . C18 . 1.485(2) yes
C18 . C19 . 1.484(2) yes
C19 . C20 . 1.353(2) yes
C20 . C21 . 1.454(2) yes
C20 . H201 . 0.950 no
C21 . C22 . 1.409(2) yes
C21 . C26 . 1.391(3) yes
C22 . C23 . 1.376(3) yes
C22 . H221 . 0.950 no
C23 . C24 . 1.366(3) yes
C23 . H231 . 0.950 no
C24 . C25 . 1.377(3) yes
C24 . F1 . 1.360(3) yes
C25 . C26 . 1.388(3) yes
C25 . H251 . 0.950 no
C26 . H261 . 0.950 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
C6 . N1 . C7 . 124.68(12) yes
C6 . N1 . H2 . 114.4(10) no
C7 . N1 . H2 . 119.1(10) no
C7 . N2 . C8 . 124.77(13) yes
C7 . N2 . C9 . 117.73(12) yes
C8 . N2 . C9 . 113.06(12) yes
C2 . C1 . C6 . 119.36(19) yes
C2 . C1 . H11 . 120.9 no
C6 . C1 . H11 . 119.7 no
C1 . C2 . C3 . 120.8(2) yes
C1 . C2 . H21 . 119.6 no
C3 . C2 . H21 . 119.6 no
C2 . C3 . C4 . 119.32(19) yes
C2 . C3 . H31 . 120.6 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 122.1(2) yes
C3 . C4 . H41 . 119.0 no
C5 . C4 . H41 . 118.9 no
C4 . C5 . C6 . 118.3(2) yes
C4 . C5 . H51 . 121.5 no
C6 . C5 . H51 . 120.2 no
N1 . C6 . C5 . 122.38(15) yes
N1 . C6 . C1 . 117.49(14) yes
C5 . C6 . C1 . 120.10(15) yes
N2 . C7 . N1 . 114.53(12) yes
N2 . C7 . O1 . 121.43(13) yes
N1 . C7 . O1 . 123.93(13) yes
N2 . C8 . C19 . 110.19(13) yes
N2 . C8 . H81 . 109.4 no
C19 . C8 . H81 . 109.3 no
N2 . C8 . H82 . 109.0 no
C19 . C8 . H82 . 109.5 no
H81 . C8 . H82 . 109.5 no
N2 . C9 . C17 . 108.98(12) yes
N2 . C9 . H91 . 109.6 no
C17 . C9 . H91 . 109.2 no
N2 . C9 . H92 . 109.7 no
C17 . C9 . H92 . 109.9 no
H91 . C9 . H92 . 109.5 no
C11 . C10 . C15 . 121.2(2) yes
C11 . C10 . H101 . 119.9 no
C15 . C10 . H101 . 118.9 no
C10 . C11 . C12 . 119.3(3) yes
C10 . C11 . H111 . 121.7 no
C12 . C11 . H111 . 119.0 no
C11 . C12 . C13 . 123.1(2) yes
C11 . C12 . F2 . 119.3(3) yes
C13 . C12 . F2 . 117.6(3) yes
C12 . C13 . C14 . 118.2(3) yes
C12 . C13 . H131 . 120.6 no
C14 . C13 . H131 . 121.3 no
C13 . C14 . C15 . 120.7(3) yes
C13 . C14 . H141 . 120.9 no
C15 . C14 . H141 . 118.4 no
C10 . C15 . C14 . 117.3(2) yes
C10 . C15 . C16 . 123.95(17) yes
C14 . C15 . C16 . 118.70(19) yes
C15 . C16 . C17 . 129.04(15) yes
C15 . C16 . H161 . 115.7 no
C17 . C16 . H161 . 115.3 no
C9 . C17 . C16 . 124.47(14) yes
C9 . C17 . C18 . 117.28(14) yes
C16 . C17 . C18 . 118.14(14) yes
C17 . C18 . O2 . 120.40(16) yes
C17 . C18 . C19 . 118.40(12) yes
O2 . C18 . C19 . 121.20(14) yes
C8 . C19 . C18 . 118.38(12) yes
C8 . C19 . C20 . 123.83(15) yes
C18 . C19 . C20 . 117.78(13) yes
C19 . C20 . C21 . 131.36(15) yes
C19 . C20 . H201 . 114.2 no
C21 . C20 . H201 . 114.4 no
C20 . C21 . C22 . 117.17(17) yes
C20 . C21 . C26 . 125.34(14) yes
C22 . C21 . C26 . 117.48(18) yes
C21 . C22 . C23 . 122.0(2) yes
C21 . C22 . H221 . 118.8 no
C23 . C22 . H221 . 119.2 no
C22 . C23 . C24 . 117.94(18) yes
C22 . C23 . H231 . 121.7 no
C24 . C23 . H231 . 120.4 no
C23 . C24 . C25 . 123.0(2) yes
C23 . C24 . F1 . 119.4(2) yes
C25 . C24 . F1 . 117.6(2) yes
C24 . C25 . C26 . 118.3(2) yes
C24 . C25 . H251 . 119.7 no
C26 . C25 . H251 . 122.0 no
C21 . C26 . C25 . 121.28(17) yes
C21 . C26 . H261 . 119.2 no
C25 . C26 . H261 . 119.5 no


