# Supplementary Information (SI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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. 
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data_P21_c_100K
_database_code_depnum_ccdc_archive 'CCDC 2386800'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-02-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1961(3)
_cell_length_b                   14.5683(4)
_cell_length_c                   24.7525(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.1460(10)
_cell_angle_gamma                90
_cell_volume                     4386.43(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7131
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0947 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.9567.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            59672
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.412
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                   xray
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6441
_reflns_number_total             9004
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     605
_refine_ls_number_reflns         9004
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.090
_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)+(0.0844P)²+5.4785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1954
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00S(H00A,H00B), C010(H01V,H01W), C013(H01A,H01B), C015(H01X,H01Y), C016(H01Z,
 H), C018(H01C,H01D), C019(H01,HA), C01A(H1,HB), C01B(H01E,H01F), C01D(H01H,
 H01I), C01E(H2,HC), C01G(H01J,H01K), C01H(H01L,H01M), C01I(H3,HD), C01K(H01O,
 H01P), C01O(H5,HE)
2.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00M(H00M), C011(H011), C014(H014), C017(H017), C01C(H01G),
 C01J(H01N), C01L(H01Q), C01M(H4), C01N(H01R), C01Q(H6), C01R(H7), C01T(H9),
 C01U(H10)
2.c Idealised Me refined as rotating group:
 C01P(H01S,H01T,H01U), C01S(H8,HF,HG)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F2A F 0.92797(10) 0.32515(9) 0.40674(5) 0.0231(3) Uani 1 1 d . . . . .
F2 F 0.41419(10) 0.32534(9) 0.40183(5) 0.0247(3) Uani 1 1 d . . . . .
F1 F 0.39690(11) 0.43760(9) 0.22340(5) 0.0244(3) Uani 1 1 d . . . . .
F1A F 0.90639(11) 0.42938(9) 0.22639(5) 0.0272(3) Uani 1 1 d . . . . .
O3 O -0.05364(13) 0.57878(11) 0.45116(6) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.63243(13) 0.17267(11) 0.26925(7) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.08996(14) 0.59362(12) 0.30123(6) 0.0308(4) Uani 1 1 d . . . . .
O3A O 0.44816(14) 0.56943(11) 0.45032(6) 0.0282(4) Uani 1 1 d . . . . .
O2A O 0.59763(14) 0.58506(12) 0.30200(6) 0.0323(4) Uani 1 1 d . . . . .
O1A O 1.13539(14) 0.16042(12) 0.27490(7) 0.0345(4) Uani 1 1 d . . . . .
N2 N 0.22189(14) 0.42867(11) 0.42380(7) 0.0169(4) Uani 1 1 d . . . . .
N2A N 0.73036(14) 0.42400(12) 0.42685(7) 0.0178(4) Uani 1 1 d . . . . .
N3A N 0.44017(15) 0.63198(13) 0.36607(7) 0.0211(4) Uani 1 1 d . . . . .
N1 N 0.49277(14) 0.31334(12) 0.30491(7) 0.0194(4) Uani 1 1 d . . . . .
N3 N -0.06402(15) 0.64198(13) 0.36694(7) 0.0224(4) Uani 1 1 d . . . . .
N1A N 1.00037(15) 0.30548(13) 0.30869(7) 0.0216(4) Uani 1 1 d . . . . .
C9A C 0.78100(17) 0.42651(14) 0.37797(8) 0.0176(4) Uani 1 1 d . . . . .
C16 C 0.08075(17) 0.53514(14) 0.39075(8) 0.0181(4) Uani 1 1 d . . . . .
C5 C 0.40765(16) 0.37608(14) 0.31255(8) 0.0178(4) Uani 1 1 d . . . . .
C10A C 0.87463(17) 0.37501(14) 0.36696(8) 0.0183(4) Uani 1 1 d . . . . .
C15 C 0.12980(16) 0.47789(14) 0.42949(8) 0.0169(4) Uani 1 1 d . . . . .
H19 H 0.096254 0.472604 0.462816 0.020 Uiso 1 1 calc R U . . .
C15A C 0.63709(17) 0.47298(14) 0.43146(8) 0.0182(4) Uani 1 1 d . . . . .
H19A H 0.603133 0.468673 0.464717 0.022 Uiso 1 1 calc R U . . .
C8 C 0.22560(16) 0.48813(14) 0.33295(8) 0.0173(4) Uani 1 1 d . . . . .
C5A C 0.91692(17) 0.36976(14) 0.31610(8) 0.0190(4) Uani 1 1 d . . . . .
C8A C 0.73513(17) 0.48205(14) 0.33563(8) 0.0195(4) Uani 1 1 d . . . . .
C18A C 0.48593(17) 0.57779(14) 0.40552(8) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.27102(16) 0.43142(14) 0.37459(8) 0.0170(4) Uani 1 1 d . . . . .
C11A C 0.77357(17) 0.37081(14) 0.47499(8) 0.0194(4) Uani 1 1 d . . . . .
H10A H 0.740915 0.395876 0.507365 0.023 Uiso 1 1 calc R U . . .
H11A H 0.854024 0.380411 0.479955 0.023 Uiso 1 1 calc R U . . .
C10 C 0.36403(17) 0.37927(14) 0.36297(8) 0.0184(4) Uani 1 1 d . . . . .
C16A C 0.58777(17) 0.52823(14) 0.39202(8) 0.0190(4) Uani 1 1 d . . . . .
C18 C -0.01798(17) 0.58619(15) 0.40588(8) 0.0193(4) Uani 1 1 d . . . . .
C17A C 0.63545(18) 0.53659(15) 0.34070(8) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.35938(17) 0.43647(14) 0.27352(8) 0.0192(4) Uani 1 1 d . . . . .
C20A C 0.36703(18) 0.78909(15) 0.37797(8) 0.0218(4) Uani 1 1 d . . . . .
C17 C 0.12757(17) 0.54381(15) 0.33932(8) 0.0195(4) Uani 1 1 d . . . . .
C11 C 0.26092(18) 0.36926(14) 0.46973(8) 0.0204(4) Uani 1 1 d . . . . .
H10 H 0.230901 0.392135 0.503317 0.024 Uiso 1 1 calc R U . . .
H11 H 0.342116 0.372465 0.474658 0.024 Uiso 1 1 calc R U . . .
C7A C 0.78261(18) 0.48529(15) 0.28570(9) 0.0214(4) Uani 1 1 d . . . . .
H9A H 0.754519 0.526311 0.258250 0.026 Uiso 1 1 calc R U . . .
C6A C 0.86903(18) 0.42954(15) 0.27663(8) 0.0216(4) Uani 1 1 d . . . . .
C19A C 0.34353(18) 0.68716(15) 0.37304(9) 0.0214(4) Uani 1 1 d . . . . .
H22A H 0.309416 0.666317 0.406005 0.026 Uiso 1 1 calc R U . . .
H21A H 0.289689 0.676851 0.341753 0.026 Uiso 1 1 calc R U . . .
C7 C 0.27278(17) 0.49175(15) 0.28303(8) 0.0200(4) Uani 1 1 d . . . . .
H9 H 0.244284 0.532888 0.255739 0.024 Uiso 1 1 calc R U . . .
C1 C 0.56300(17) 0.32816(15) 0.25976(9) 0.0217(4) Uani 1 1 d . . . . .
H1 H 0.585595 0.393334 0.258353 0.026 Uiso 1 1 calc R U . . .
H2 H 0.522544 0.312157 0.224917 0.026 Uiso 1 1 calc R U . . .
C4 C 0.46018(19) 0.21573(15) 0.30656(10) 0.0251(5) Uani 1 1 d . . . . .
H8 H 0.415017 0.199696 0.273045 0.030 Uiso 1 1 calc R U . . .
H7 H 0.415526 0.204966 0.337799 0.030 Uiso 1 1 calc R U . . .
C21A C 0.2814(2) 0.85064(16) 0.36619(9) 0.0277(5) Uani 1 1 d . . . . .
H23A H 0.209754 0.828226 0.355933 0.033 Uiso 1 1 calc R U . . .
C4A C 0.96521(19) 0.20867(15) 0.31266(10) 0.0258(5) Uani 1 1 d . . . . .
H8A H 0.918440 0.191535 0.279853 0.031 Uiso 1 1 calc R U . . .
H7A H 0.921500 0.200823 0.344525 0.031 Uiso 1 1 calc R U . . .
C19 C -0.15703(18) 0.70048(16) 0.37591(9) 0.0249(5) Uani 1 1 d . . . . .
H22 H -0.192931 0.677982 0.407996 0.030 Uiso 1 1 calc R U . . .
H21 H -0.211181 0.696010 0.344241 0.030 Uiso 1 1 calc R U . . .
C2 C 0.66281(18) 0.26718(16) 0.26956(9) 0.0237(5) Uani 1 1 d . . . . .
H4 H 0.714138 0.278342 0.241055 0.028 Uiso 1 1 calc R U . . .
H3 H 0.701314 0.282737 0.304961 0.028 Uiso 1 1 calc R U . . .
C1A C 1.06784(18) 0.31612(16) 0.26234(9) 0.0244(5) Uani 1 1 d . . . . .
H1A H 1.091490 0.380760 0.259068 0.029 Uiso 1 1 calc R U . . .
H2A H 1.025379 0.298217 0.228377 0.029 Uiso 1 1 calc R U . . .
C25A C 0.4712(2) 0.82270(17) 0.39279(10) 0.0288(5) Uani 1 1 d . . . . .
H27A H 0.530396 0.781410 0.400939 0.035 Uiso 1 1 calc R U . . .
C13A C 0.63147(19) 0.24150(16) 0.46716(10) 0.0282(5) Uani 1 1 d . . . . .
H14A H 0.597362 0.264102 0.432153 0.034 Uiso 1 1 calc R U . . .
H15A H 0.593171 0.270887 0.496555 0.034 Uiso 1 1 calc R U . . .
C12 C 0.2259(2) 0.26964(15) 0.46043(10) 0.0278(5) Uani 1 1 d . . . . .
H13 H 0.146901 0.263794 0.466668 0.033 Uiso 1 1 calc R U . . .
H12 H 0.234802 0.253351 0.422164 0.033 Uiso 1 1 calc R U . . .
C20 C -0.1255(2) 0.80026(17) 0.38471(10) 0.0290(5) Uani 1 1 d . . . . .
C2A C 1.16676(18) 0.25416(17) 0.27265(10) 0.0282(5) Uani 1 1 d . . . . .
H3A H 1.217034 0.262598 0.243380 0.034 Uiso 1 1 calc R U . . .
H4A H 1.206914 0.271640 0.307311 0.034 Uiso 1 1 calc R U . . .
C12A C 0.75131(19) 0.26830(16) 0.47233(10) 0.0266(5) Uani 1 1 d . . . . .
H12A H 0.787208 0.242715 0.441026 0.032 Uiso 1 1 calc R U . . .
H13A H 0.786238 0.239466 0.505465 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5621(2) 0.15608(16) 0.31168(10) 0.0299(5) Uani 1 1 d . . . . .
H5 H 0.602962 0.168249 0.346974 0.036 Uiso 1 1 calc R U . . .
H6 H 0.539904 0.090703 0.310975 0.036 Uiso 1 1 calc R U . . .
C22A C 0.3000(2) 0.94475(17) 0.36931(10) 0.0339(6) Uani 1 1 d . . . . .
H24A H 0.241145 0.986373 0.361079 0.041 Uiso 1 1 calc R U . . .
C3A C 1.0656(2) 0.14721(17) 0.31815(11) 0.0335(6) Uani 1 1 d . . . . .
H6A H 1.107586 0.160215 0.353036 0.040 Uiso 1 1 calc R U . . .
H5A H 1.041676 0.082288 0.318592 0.040 Uiso 1 1 calc R U . . .
C23A C 0.4035(2) 0.97755(17) 0.38432(11) 0.0356(6) Uani 1 1 d . . . . .
H25A H 0.416100 1.041809 0.386830 0.043 Uiso 1 1 calc R U . . .
C25 C -0.1970(3) 0.86942(18) 0.36601(10) 0.0389(6) Uani 1 1 d . . . . .
H27 H -0.264711 0.853725 0.346846 0.047 Uiso 1 1 calc R U . . .
C24A C 0.4890(2) 0.91690(18) 0.39572(11) 0.0347(6) Uani 1 1 d . . . . .
H26A H 0.560643 0.939708 0.405653 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2899(2) 0.20310(17) 0.49628(10) 0.0353(6) Uani 1 1 d . . . . .
H15 H 0.283864 0.220824 0.534565 0.042 Uiso 1 1 calc R U . . .
H14 H 0.368394 0.206410 0.488766 0.042 Uiso 1 1 calc R U . . .
C14A C 0.6173(2) 0.13742(17) 0.47022(11) 0.0349(6) Uani 1 1 d . . . . .
H16A H 0.655127 0.108196 0.441149 0.052 Uiso 1 1 calc R U . . .
H18A H 0.538835 0.122151 0.466102 0.052 Uiso 1 1 calc R U . . .
H17A H 0.648675 0.115186 0.505364 0.052 Uiso 1 1 calc R U . . .
C21 C -0.0270(2) 0.82475(19) 0.41309(13) 0.0437(7) Uani 1 1 d . . . . .
H23 H 0.022715 0.778275 0.426171 0.052 Uiso 1 1 calc R U . . .
C24 C -0.1706(3) 0.9614(2) 0.37503(12) 0.0513(9) Uani 1 1 d . . . . .
H26 H -0.219990 1.008104 0.361857 0.062 Uiso 1 1 calc R U . . .
C14 C 0.2495(3) 0.10450(19) 0.48807(12) 0.0506(8) Uani 1 1 d . . . . .
H16 H 0.255933 0.086375 0.450299 0.076 Uiso 1 1 calc R U . . .
H18 H 0.172493 0.100381 0.496628 0.076 Uiso 1 1 calc R U . . .
H17 H 0.294344 0.063458 0.512015 0.076 Uiso 1 1 calc R U . . .
C23 C -0.0725(3) 0.9847(2) 0.40319(16) 0.0598(10) Uani 1 1 d . . . . .
H25 H -0.054261 1.047467 0.409299 0.072 Uiso 1 1 calc R U . . .
C22 C -0.0008(3) 0.9165(2) 0.42248(17) 0.0585(9) Uani 1 1 d . . . . .
H24 H 0.066337 0.932455 0.442112 0.070 Uiso 1 1 calc R U . . .
H20 H -0.032(3) 0.640(2) 0.3334(13) 0.046(9) Uiso 1 1 d . . . . .
H20A H 0.474(2) 0.6307(19) 0.3335(12) 0.036(7) Uiso 1 1 d . . . . .


_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
F2A C10A 1.352(2) . ?
F2 C10 1.353(2) . ?
F1 C6 1.353(2) . ?
F1A C6A 1.355(2) . ?
O3 C18 1.236(3) . ?
O1 C2 1.426(3) . ?
O1 C3 1.424(3) . ?
O2 C17 1.250(3) . ?
O3A C18A 1.237(3) . ?
O2A C17A 1.251(3) . ?
O1A C2A 1.420(3) . ?
O1A C3A 1.428(3) . ?
N2 C15 1.348(3) . ?
N2 C9 1.396(3) . ?
N2 C11 1.480(3) . ?
N2A C9A 1.398(3) . ?
N2A C15A 1.355(3) . ?
N2A C11A 1.486(3) . ?
N3A C18A 1.345(3) . ?
N3A C19A 1.447(3) . ?
N3A H20A 0.93(3) . ?
N1 C5 1.406(3) . ?
N1 C1 1.472(3) . ?
N1 C4 1.478(3) . ?
N3 C18 1.351(3) . ?
N3 C19 1.449(3) . ?
N3 H20 0.94(3) . ?
N1A C5A 1.405(3) . ?
N1A C4A 1.479(3) . ?
N1A C1A 1.467(3) . ?
C9A C10A 1.409(3) . ?
C9A C8A 1.408(3) . ?
C16 C15 1.375(3) . ?
C16 C18 1.486(3) . ?
C16 C17 1.438(3) . ?
C5 C10 1.392(3) . ?
C5 C6 1.404(3) . ?
C10A C5A 1.397(3) . ?
C15 H19 0.9500 . ?
C15A H19A 0.9500 . ?
C15A C16A 1.370(3) . ?
C8 C9 1.403(3) . ?
C8 C17 1.463(3) . ?
C8 C7 1.401(3) . ?
C5A C6A 1.404(3) . ?
C8A C17A 1.465(3) . ?
C8A C7A 1.403(3) . ?
C18A C16A 1.495(3) . ?
C9 C10 1.412(3) . ?
C11A H10A 0.9900 . ?
C11A H11A 0.9900 . ?
C11A C12A 1.518(3) . ?
C16A C17A 1.440(3) . ?
C6 C7 1.362(3) . ?
C20A C19A 1.516(3) . ?
C20A C21A 1.391(3) . ?
C20A C25A 1.386(3) . ?
C11 H10 0.9900 . ?
C11 H11 0.9900 . ?
C11 C12 1.526(3) . ?
C7A H9A 0.9500 . ?
C7A C6A 1.362(3) . ?
C19A H22A 0.9900 . ?
C19A H21A 0.9900 . ?
C7 H9 0.9500 . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C1 C2 1.512(3) . ?
C4 H8 0.9900 . ?
C4 H7 0.9900 . ?
C4 C3 1.514(3) . ?
C21A H23A 0.9500 . ?
C21A C22A 1.391(3) . ?
C4A H8A 0.9900 . ?
C4A H7A 0.9900 . ?
C4A C3A 1.515(3) . ?
C19 HA 0.9900 . ?
C19 H22 0.9900 . ?
C19 C20 1.515(3) . ?
C2 HB 0.9900 . ?
C2 H4 0.9900 . ?
C1A H1A 0.9900 . ?
C1A H2A 0.9900 . ?
C1A C2A 1.514(3) . ?
C25A H27A 0.9500 . ?
C25A C24A 1.390(3) . ?
C13A H14A 0.9900 . ?
C13A H15A 0.9900 . ?
C13A C12A 1.509(3) . ?
C13A C14A 1.529(3) . ?
C12 HC 0.9900 . ?
C12 H13 0.9900 . ?
C12 C13 1.495(3) . ?
C20 C25 1.390(3) . ?
C20 C21 1.393(4) . ?
C2A H3A 0.9900 . ?
C2A H4A 0.9900 . ?
C12A H12A 0.9900 . ?
C12A H13A 0.9900 . ?
C3 HD 0.9900 . ?
C3 H5 0.9900 . ?
C22A H24A 0.9500 . ?
C22A C23A 1.376(4) . ?
C3A H6A 0.9900 . ?
C3A H5A 0.9900 . ?
C23A H25A 0.9500 . ?
C23A C24A 1.381(4) . ?
C25 H27 0.9500 . ?
C25 C24 1.393(4) . ?
C24A H26A 0.9500 . ?
C13 HE 0.9900 . ?
C13 H15 0.9900 . ?
C13 C14 1.527(4) . ?
C14A H16A 0.9800 . ?
C14A H18A 0.9800 . ?
C14A H17A 0.9800 . ?
C21 H23 0.9500 . ?
C21 C22 1.390(4) . ?
C24 H26 0.9500 . ?
C24 C23 1.383(5) . ?
C14 HF 0.9800 . ?
C14 HG 0.9800 . ?
C14 H16 0.9800 . ?
C23 H25 0.9500 . ?
C23 C22 1.386(5) . ?
C22 H24 0.9500 . ?

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
C3 O1 C2 109.28(16) . . ?
HF C14 HG 109.5 . . ?
C2A O1A C3A 109.63(17) . . ?
O1 C2 HB 109.4 . . ?
O1 C3 HD 109.2 . . ?
C15 N2 C9 119.28(17) . . ?
C15 N2 C11 117.05(16) . . ?
C9 N2 C11 123.54(17) . . ?
C9A N2A C11A 123.68(17) . . ?
C15A N2A C9A 119.03(17) . . ?
C15A N2A C11A 117.29(16) . . ?
C18A N3A C19A 122.56(18) . . ?
C18A N3A H20A 115.6(18) . . ?
C19A N3A H20A 121.8(18) . . ?
C5 N1 C1 118.85(17) . . ?
C5 N1 C4 114.78(17) . . ?
C1 N1 C4 109.54(16) . . ?
C18 N3 C19 122.27(18) . . ?
C18 N3 H20 115.7(19) . . ?
C19 N3 H20 122.0(19) . . ?
C5A N1A C4A 114.24(17) . . ?
C5A N1A C1A 118.97(18) . . ?
C1A N1A C4A 109.52(17) . . ?
N2A C9A C10A 124.63(19) . . ?
N2A C9A C8A 118.86(18) . . ?
C8A C9A C10A 116.49(18) . . ?
C15 C16 C18 116.58(18) . . ?
C15 C16 C17 119.35(18) . . ?
C17 C16 C18 124.06(18) . . ?
C10 C5 N1 118.42(18) . . ?
C10 C5 C6 115.31(18) . . ?
C6 C5 N1 126.26(18) . . ?
F2A C10A C9A 119.95(18) . . ?
F2A C10A C5A 115.93(18) . . ?
C5A C10A C9A 124.10(19) . . ?
N2 C15 C16 124.99(18) . . ?
N2 C15 H19 117.5 . . ?
C16 C15 H19 117.5 . . ?
N2A C15A H19A 117.4 . . ?
N2A C15A C16A 125.27(19) . . ?
C16A C15A H19A 117.4 . . ?
C9 C8 C17 121.98(18) . . ?
C7 C8 C9 120.29(19) . . ?
C7 C8 C17 117.72(18) . . ?
C10A C5A N1A 118.21(19) . . ?
C10A C5A C6A 115.53(19) . . ?
C6A C5A N1A 126.25(19) . . ?
C9A C8A C17A 122.38(18) . . ?
C7A C8A C9A 120.53(19) . . ?
C7A C8A C17A 117.06(19) . . ?
O3A C18A N3A 123.14(19) . . ?
O3A C18A C16A 121.46(19) . . ?
N3A C18A C16A 115.40(18) . . ?
N2 C9 C8 119.09(18) . . ?
N2 C9 C10 124.32(18) . . ?
C8 C9 C10 116.58(18) . . ?
N2A C11A H10A 108.5 . . ?
N2A C11A H11A 108.5 . . ?
N2A C11A C12A 115.22(18) . . ?
H10A C11A H11A 107.5 . . ?
C12A C11A H10A 108.5 . . ?
C12A C11A H11A 108.5 . . ?
F2 C10 C5 115.81(18) . . ?
F2 C10 C9 119.74(17) . . ?
N3 C19 HA 109.0 . . ?
C5 C10 C9 124.41(19) . . ?
C15A C16A C18A 116.96(18) . . ?
C15A C16A C17A 119.58(19) . . ?
C17A C16A C18A 123.45(19) . . ?
O3 C18 N3 123.0(2) . . ?
O3 C18 C16 121.97(19) . . ?
N3 C18 C16 115.06(18) . . ?
O2A C17A C8A 120.18(19) . . ?
O2A C17A C16A 125.0(2) . . ?
C16A C17A C8A 114.84(18) . . ?
F1 C6 C5 119.07(18) . . ?
F1 C6 C7 117.98(19) . . ?
C7 C6 C5 122.90(19) . . ?
C21A C20A C19A 118.7(2) . . ?
C25A C20A C19A 122.1(2) . . ?
C25A C20A C21A 119.2(2) . . ?
O2 C17 C16 124.82(19) . . ?
O2 C17 C8 119.92(18) . . ?
C16 C17 C8 115.26(18) . . ?
N2 C11 H10 109.3 . . ?
N2 C11 H11 109.3 . . ?
N2 C11 C12 111.67(18) . . ?
H10 C11 H11 107.9 . . ?
C12 C11 H10 109.3 . . ?
C12 C11 H11 109.3 . . ?
C8A C7A H9A 120.0 . . ?
C6A C7A C8A 119.9(2) . . ?
C6A C7A H9A 120.0 . . ?
F1A C6A C5A 119.14(19) . . ?
F1A C6A C7A 117.89(19) . . ?
C7A C6A C5A 122.90(19) . . ?
N3A C19A C20A 113.76(18) . . ?
N3A C19A H22A 108.8 . . ?
N3A C19A H21A 108.8 . . ?
C20A C19A H22A 108.8 . . ?
C20A C19A H21A 108.8 . . ?
H22A C19A H21A 107.7 . . ?
C8 C7 H9 119.9 . . ?
C6 C7 C8 120.21(19) . . ?
C6 C7 H9 119.9 . . ?
N1 C1 H1 110.2 . . ?
N1 C1 H2 110.2 . . ?
N1 C1 C2 107.33(17) . . ?
H1 C1 H2 108.5 . . ?
C2 C1 H1 110.2 . . ?
C2 C1 H2 110.2 . . ?
N1 C4 H8 109.8 . . ?
N1 C4 H7 109.8 . . ?
N1 C4 C3 109.50(18) . . ?
C11 C12 HC 108.9 . . ?
C1 C2 HB 109.4 . . ?
C4 C3 HD 109.2 . . ?
H8 C4 H7 108.2 . . ?
H22 C19 HA 107.8 . . ?
H4 C2 HB 108.0 . . ?
C12 C13 HE 109.1 . . ?
H13 C12 HC 107.7 . . ?
C20 C19 HA 109.0 . . ?
C3 C4 H8 109.8 . . ?
C3 C4 H7 109.8 . . ?
C20A C21A H23A 119.8 . . ?
C22A C21A C20A 120.5(2) . . ?
C22A C21A H23A 119.8 . . ?
N1A C4A H8A 109.8 . . ?
N1A C4A H7A 109.8 . . ?
N1A C4A C3A 109.46(18) . . ?
H8A C4A H7A 108.2 . . ?
C3A C4A H8A 109.8 . . ?
C3A C4A H7A 109.8 . . ?
N3 C19 H22 109.0 . . ?
N3 C19 C20 113.13(19) . . ?
C20 C19 H22 109.0 . . ?
O1 C2 C1 111.13(17) . . ?
O1 C2 H4 109.4 . . ?
C1 C2 H4 109.4 . . ?
N1A C1A H1A 110.3 . . ?
N1A C1A H2A 110.3 . . ?
N1A C1A C2A 106.89(19) . . ?
H1A C1A H2A 108.6 . . ?
C2A C1A H1A 110.3 . . ?
C2A C1A H2A 110.3 . . ?
C20A C25A H27A 120.0 . . ?
C20A C25A C24A 120.0(2) . . ?
C24A C25A H27A 120.0 . . ?
H14A C13A H15A 108.0 . . ?
C12A C13A H14A 109.3 . . ?
C12A C13A H15A 109.3 . . ?
C12A C13A C14A 111.4(2) . . ?
C14A C13A H14A 109.3 . . ?
C14A C13A H15A 109.3 . . ?
C11 C12 H13 108.9 . . ?
C13 C12 C11 113.5(2) . . ?
C13 C12 H13 108.9 . . ?
C25 C20 C19 120.0(2) . . ?
C25 C20 C21 118.7(3) . . ?
C21 C20 C19 121.2(2) . . ?
O1A C2A C1A 111.49(18) . . ?
O1A C2A H3A 109.3 . . ?
O1A C2A H4A 109.3 . . ?
C1A C2A H3A 109.3 . . ?
C1A C2A H4A 109.3 . . ?
H3A C2A H4A 108.0 . . ?
C11A C12A H12A 108.5 . . ?
C11A C12A H13A 108.5 . . ?
C13A C12A C11A 115.28(19) . . ?
C13A C12A H12A 108.5 . . ?
C13A C12A H13A 108.5 . . ?
H12A C12A H13A 107.5 . . ?
O1 C3 C4 112.1(2) . . ?
O1 C3 H5 109.2 . . ?
C4 C3 H5 109.2 . . ?
C21A C22A H24A 120.0 . . ?
C23A C22A C21A 120.0(2) . . ?
C23A C22A H24A 120.0 . . ?
O1A C3A C4A 112.0(2) . . ?
O1A C3A H6A 109.2 . . ?
O1A C3A H5A 109.2 . . ?
C4A C3A H6A 109.2 . . ?
C4A C3A H5A 109.2 . . ?
H6A C3A H5A 107.9 . . ?
C22A C23A H25A 120.1 . . ?
C22A C23A C24A 119.9(2) . . ?
C24A C23A H25A 120.1 . . ?
C20 C25 H27 119.6 . . ?
C20 C25 C24 120.8(3) . . ?
C24 C25 H27 119.6 . . ?
C25A C24A H26A 119.7 . . ?
C23A C24A C25A 120.5(2) . . ?
C23A C24A H26A 119.7 . . ?
C12 C13 H15 109.1 . . ?
C12 C13 C14 112.4(2) . . ?
H5 C3 HD 107.9 . . ?
C13 C12 HC 108.9 . . ?
C13 C14 HG 109.5 . . ?
C14 C13 H15 109.1 . . ?
C13 C14 HF 109.5 . . ?
H15 C13 HE 107.8 . . ?
C14 C13 HE 109.1 . . ?
C13A C14A H16A 109.5 . . ?
C13A C14A H18A 109.5 . . ?
C13A C14A H17A 109.5 . . ?
H16A C14A H18A 109.5 . . ?
H16A C14A H17A 109.5 . . ?
H18A C14A H17A 109.5 . . ?
C20 C21 H23 119.7 . . ?
C22 C21 C20 120.7(3) . . ?
C22 C21 H23 119.7 . . ?
C25 C24 H26 120.1 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H26 120.1 . . ?
C13 C14 H16 109.5 . . ?
C24 C23 H25 120.0 . . ?
C24 C23 C22 119.9(3) . . ?
H16 C14 HG 109.5 . . ?
H16 C14 HF 109.5 . . ?
C22 C23 H25 120.0 . . ?
C21 C22 H24 120.0 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H24 120.0 . . ?

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
F2A C10A C5A N1A 8.0(3) . . . . ?
F2A C10A C5A C6A -173.07(17) . . . . ?
F1 C6 C7 C8 175.25(18) . . . . ?
O3A C18A C16A C15A 0.2(3) . . . . ?
O3A C18A C16A C17A -179.3(2) . . . . ?
N2 C9 C10 F2 -3.1(3) . . . . ?
N2 C9 C10 C5 174.41(19) . . . . ?
N2 C11 C12 C13 162.52(18) . . . . ?
N2A C9A C10A F2A -6.4(3) . . . . ?
N2A C9A C10A C5A 172.18(19) . . . . ?
N2A C9A C8A C17A -0.7(3) . . . . ?
N2A C9A C8A C7A -179.01(18) . . . . ?
N2A C15A C16A C18A -179.02(19) . . . . ?
N2A C15A C16A C17A 0.5(3) . . . . ?
N2A C11A C12A C13A -60.7(3) . . . . ?
N3A C18A C16A C15A 179.47(19) . . . . ?
N3A C18A C16A C17A 0.0(3) . . . . ?
N1 C5 C10 F2 4.8(3) . . . . ?
N1 C5 C10 C9 -172.85(19) . . . . ?
N1 C5 C6 F1 -1.0(3) . . . . ?
N1 C5 C6 C7 176.1(2) . . . . ?
N1 C1 C2 O1 62.6(2) . . . . ?
N1 C4 C3 O1 -56.2(3) . . . . ?
N3 C19 C20 C25 145.8(2) . . . . ?
N3 C19 C20 C21 -36.5(3) . . . . ?
N1A C5A C6A F1A -2.0(3) . . . . ?
N1A C5A C6A C7A 174.9(2) . . . . ?
N1A C4A C3A O1A -55.5(3) . . . . ?
N1A C1A C2A O1A 62.8(2) . . . . ?
C9A N2A C15A C16A -1.8(3) . . . . ?
C9A N2A C11A C12A -77.8(2) . . . . ?
C9A C10A C5A N1A -170.63(19) . . . . ?
C9A C10A C5A C6A 8.3(3) . . . . ?
C9A C8A C17A O2A 179.9(2) . . . . ?
C9A C8A C17A C16A -0.6(3) . . . . ?
C9A C8A C7A C6A 4.7(3) . . . . ?
C5 N1 C1 C2 165.64(18) . . . . ?
C5 N1 C4 C3 -166.23(18) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
C10A C9A C8A C17A 177.69(19) . . . . ?
C10A C9A C8A C7A -0.6(3) . . . . ?
C10A C5A C6A F1A 179.24(18) . . . . ?
C10A C5A C6A C7A -3.9(3) . . . . ?
C15 N2 C9 C8 2.4(3) . . . . ?
C15 N2 C9 C10 -176.58(19) . . . . ?
C15 N2 C11 C12 98.8(2) . . . . ?
C15 C16 C18 O3 1.0(3) . . . . ?
C15 C16 C18 N3 179.86(19) . . . . ?
C15 C16 C17 O2 180.0(2) . . . . ?
C15 C16 C17 C8 0.6(3) . . . . ?
C15A N2A C9A C10A -176.41(19) . . . . ?
C15A N2A C9A C8A 1.8(3) . . . . ?
C15A N2A C11A C12A 102.8(2) . . . . ?
C15A C16A C17A O2A -179.8(2) . . . . ?
C15A C16A C17A C8A 0.7(3) . . . . ?
C8 C9 C10 F2 177.89(17) . . . . ?
C8 C9 C10 C5 -4.6(3) . . . . ?
C5A N1A C4A C3A -165.92(19) . . . . ?
C5A N1A C1A C2A 165.64(18) . . . . ?
C8A C9A C10A F2A 175.29(17) . . . . ?
C8A C9A C10A C5A -6.1(3) . . . . ?
C8A C7A C6A F1A 174.60(18) . . . . ?
C8A C7A C6A C5A -2.3(3) . . . . ?
C18A N3A C19A C20A 107.6(2) . . . . ?
C18A C16A C17A O2A -0.4(4) . . . . ?
C18A C16A C17A C8A -179.85(19) . . . . ?
C9 N2 C15 C16 -2.8(3) . . . . ?
C9 N2 C11 C12 -76.9(2) . . . . ?
C9 C8 C17 O2 179.8(2) . . . . ?
C9 C8 C17 C16 -0.8(3) . . . . ?
C9 C8 C7 C6 3.6(3) . . . . ?
C11A N2A C9A C10A 4.2(3) . . . . ?
C11A N2A C9A C8A -177.60(18) . . . . ?
C11A N2A C15A C16A 177.67(19) . . . . ?
C10 C5 C6 F1 -179.91(18) . . . . ?
C10 C5 C6 C7 -2.8(3) . . . . ?
C18 N3 C19 C20 103.1(2) . . . . ?
C18 C16 C15 N2 -177.61(19) . . . . ?
C18 C16 C17 O2 -1.3(3) . . . . ?
C18 C16 C17 C8 179.33(18) . . . . ?
C17A C8A C7A C6A -173.7(2) . . . . ?
C6 C5 C10 F2 -176.24(17) . . . . ?
C6 C5 C10 C9 6.1(3) . . . . ?
C20A C21A C22A C23A -0.2(4) . . . . ?
C20A C25A C24A C23A 0.4(4) . . . . ?
C17 C16 C15 N2 1.2(3) . . . . ?
C17 C16 C18 O3 -177.8(2) . . . . ?
C17 C16 C18 N3 1.1(3) . . . . ?
C17 C8 C9 N2 -0.6(3) . . . . ?
C17 C8 C9 C10 178.41(18) . . . . ?
C17 C8 C7 C6 -175.34(19) . . . . ?
C11 N2 C15 C16 -178.73(19) . . . . ?
C11 N2 C9 C8 178.08(18) . . . . ?
C11 N2 C9 C10 -0.9(3) . . . . ?
C11 C12 C13 C14 177.3(2) . . . . ?
C7A C8A C17A O2A -1.7(3) . . . . ?
C7A C8A C17A C16A 177.82(19) . . . . ?
C19A N3A C18A O3A 1.4(3) . . . . ?
C19A N3A C18A C16A -177.87(18) . . . . ?
C19A C20A C21A C22A -178.9(2) . . . . ?
C19A C20A C25A C24A 178.7(2) . . . . ?
C7 C8 C9 N2 -179.57(18) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C17 O2 -1.3(3) . . . . ?
C7 C8 C17 C16 178.12(18) . . . . ?
C1 N1 C5 C10 -160.64(19) . . . . ?
C1 N1 C5 C6 20.5(3) . . . . ?
C1 N1 C4 C3 57.1(2) . . . . ?
C4 N1 C5 C10 66.9(2) . . . . ?
C4 N1 C5 C6 -112.0(2) . . . . ?
C4 N1 C1 C2 -59.7(2) . . . . ?
C21A C20A C19A N3A 158.10(19) . . . . ?
C21A C20A C25A C24A 0.0(3) . . . . ?
C21A C22A C23A C24A 0.7(4) . . . . ?
C4A N1A C5A C10A 65.8(3) . . . . ?
C4A N1A C5A C6A -113.0(2) . . . . ?
C4A N1A C1A C2A -60.4(2) . . . . ?
C19 N3 C18 O3 2.3(3) . . . . ?
C19 N3 C18 C16 -176.55(19) . . . . ?
C19 C20 C25 C24 178.2(2) . . . . ?
C19 C20 C21 C22 -177.8(3) . . . . ?
C2 O1 C3 C4 57.8(3) . . . . ?
C1A N1A C5A C10A -162.27(19) . . . . ?
C1A N1A C5A C6A 19.0(3) . . . . ?
C1A N1A C4A C3A 57.8(2) . . . . ?
C25A C20A C19A N3A -20.6(3) . . . . ?
C25A C20A C21A C22A -0.1(3) . . . . ?
C20 C25 C24 C23 -0.4(4) . . . . ?
C20 C21 C22 C23 -0.5(5) . . . . ?
C2A O1A C3A C4A 56.7(3) . . . . ?
C3 O1 C2 C1 -61.4(2) . . . . ?
C22A C23A C24A C25A -0.8(4) . . . . ?
C3A O1A C2A C1A -60.8(2) . . . . ?
C25 C20 C21 C22 -0.1(4) . . . . ?
C25 C24 C23 C22 -0.2(5) . . . . ?
C14A C13A C12A C11A -174.58(19) . . . . ?
C21 C20 C25 C24 0.5(4) . . . . ?
C24 C23 C22 C21 0.6(5) . . . . ?

_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_P21_c_150K
_database_code_depnum_ccdc_archive 'CCDC 2386803'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2135(8)
_cell_length_b                   14.5839(11)
_cell_length_c                   24.8400(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.988(3)
_cell_angle_gamma                90
_cell_volume                     4413.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      2.70
_cell_measurement_theta_min      28.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            57758
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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                   xray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5922
_reflns_number_total             9048
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.067
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9048
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.068
_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)+(0.1214P)²+6.1318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1893
_refine_ls_wR_factor_ref         0.2566
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F2A F 0.07381(13) 0.67511(11) 0.59401(6) 0.0331(4) Uani 1 1 d . . . . .
F1 F 0.60272(13) 0.56297(11) 0.77607(6) 0.0345(4) Uani 1 1 d . . . . .
F2 F 0.58595(13) 0.67502(11) 0.59833(6) 0.0343(4) Uani 1 1 d . . . . .
F1A F 0.09426(14) 0.57010(12) 0.77334(6) 0.0379(4) Uani 1 1 d . . . . .
O3 O 1.05317(16) 0.42187(14) 0.54909(8) 0.0372(5) Uani 1 1 d . . . . .
O3A O 0.55163(17) 0.43033(15) 0.54972(8) 0.0394(5) Uani 1 1 d . . . . .
O2 O 0.90823(17) 0.40666(16) 0.69810(8) 0.0421(5) Uani 1 1 d . . . . .
O1 O 0.36825(16) 0.82736(14) 0.73075(9) 0.0393(5) Uani 1 1 d . . . . .
O2A O 0.40150(18) 0.41409(16) 0.69730(8) 0.0448(6) Uani 1 1 d . . . . .
N2A N 0.27018(17) 0.57562(14) 0.57336(8) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.77801(17) 0.57176(14) 0.57618(8) 0.0235(4) Uani 1 1 d . . . . .
O1A O -0.13432(17) 0.83844(15) 0.72551(10) 0.0476(6) Uani 1 1 d . . . . .
N1 N 0.50757(17) 0.68708(15) 0.69514(8) 0.0266(5) Uani 1 1 d . . . . .
N3A N 0.55911(18) 0.36753(15) 0.63340(9) 0.0295(5) Uani 1 1 d . . . . .
H20A H 0.529018 0.365530 0.664553 0.035 Uiso 1 1 calc R U . . .
N1A N 0.00093(17) 0.69421(15) 0.69167(9) 0.0290(5) Uani 1 1 d . . . . .
N3 N 1.06250(18) 0.35855(16) 0.63258(9) 0.0307(5) Uani 1 1 d . . . . .
H20 H 1.034450 0.357481 0.664263 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7288(2) 0.56891(16) 0.62534(9) 0.0232(5) Uani 1 1 d . . . . .
C5 C 0.5924(2) 0.62437(17) 0.68731(10) 0.0240(5) Uani 1 1 d . . . . .
C8 C 0.7737(2) 0.51226(17) 0.66679(9) 0.0236(5) Uani 1 1 d . . . . .
C15 C 0.8698(2) 0.52227(16) 0.57050(10) 0.0238(5) Uani 1 1 d . . . . .
H19 H 0.903418 0.527290 0.537267 0.029 Uiso 1 1 calc R U . . .
C9A C 0.2195(2) 0.57319(17) 0.62223(10) 0.0239(5) Uani 1 1 d . . . . .
C16 C 0.9183(2) 0.46530(17) 0.60903(10) 0.0244(5) Uani 1 1 d . . . . .
C8A C 0.2650(2) 0.51738(17) 0.66429(10) 0.0260(5) Uani 1 1 d . . . . .
C18A C 0.5136(2) 0.42166(18) 0.59423(10) 0.0268(5) Uani 1 1 d . . . . .
C5A C 0.0841(2) 0.62994(18) 0.68404(10) 0.0264(5) Uani 1 1 d . . . . .
C10 C 0.6359(2) 0.62125(17) 0.63699(10) 0.0250(5) Uani 1 1 d . . . . .
C10A C 0.1263(2) 0.62477(17) 0.63353(10) 0.0254(5) Uani 1 1 d . . . . .
C15A C 0.3634(2) 0.52671(17) 0.56866(10) 0.0252(5) Uani 1 1 d . . . . .
H19A H 0.397626 0.531266 0.535582 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6403(2) 0.56402(18) 0.72599(10) 0.0264(5) Uani 1 1 d . . . . .
C18 C 1.0170(2) 0.41414(18) 0.59405(10) 0.0274(5) Uani 1 1 d . . . . .
C16A C 0.4120(2) 0.47121(17) 0.60787(10) 0.0262(5) Uani 1 1 d . . . . .
C11 C 0.7389(2) 0.63101(18) 0.53049(10) 0.0287(6) Uani 1 1 d . . . . .
H11 H 0.657852 0.627837 0.525822 0.034 Uiso 1 1 calc R U . . .
H10 H 0.768640 0.607972 0.496971 0.034 Uiso 1 1 calc R U . . .
C11A C 0.2276(2) 0.62940(17) 0.52578(10) 0.0273(5) Uani 1 1 d . . . . .
H10A H 0.147256 0.620211 0.520893 0.033 Uiso 1 1 calc R U . . .
H11A H 0.260065 0.604469 0.493399 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8712(2) 0.45653(18) 0.66020(10) 0.0270(5) Uani 1 1 d . . . . .
C7 C 0.7264(2) 0.50857(18) 0.71644(10) 0.0271(5) Uani 1 1 d . . . . .
H9 H 0.754417 0.467232 0.743563 0.033 Uiso 1 1 calc R U . . .
C17A C 0.3639(2) 0.46273(18) 0.65893(10) 0.0286(6) Uani 1 1 d . . . . .
C7A C 0.2175(2) 0.51400(19) 0.71402(10) 0.0295(6) Uani 1 1 d . . . . .
H9A H 0.245305 0.472723 0.741233 0.035 Uiso 1 1 calc R U . . .
C19A C 0.6556(2) 0.31235(18) 0.62648(11) 0.0300(6) Uani 1 1 d . . . . .
H22A H 0.709214 0.322795 0.657620 0.036 Uiso 1 1 calc R U . . .
H21A H 0.689766 0.333086 0.593608 0.036 Uiso 1 1 calc R U . . .
C6A C 0.1316(2) 0.56986(19) 0.72332(10) 0.0294(6) Uani 1 1 d . . . . .
C1 C 0.4370(2) 0.67225(19) 0.73995(11) 0.0306(6) Uani 1 1 d . . . . .
H1 H 0.477081 0.688026 0.774722 0.037 Uiso 1 1 calc R U . . .
H2 H 0.414270 0.607168 0.741232 0.037 Uiso 1 1 calc R U . . .
C20A C 0.6325(2) 0.21065(19) 0.62170(10) 0.0305(6) Uani 1 1 d . . . . .
C1A C -0.0674(2) 0.6831(2) 0.73761(11) 0.0337(6) Uani 1 1 d . . . . .
H1A H -0.025480 0.700659 0.771614 0.040 Uiso 1 1 calc R U . . .
H2A H -0.090981 0.618501 0.740588 0.040 Uiso 1 1 calc R U . . .
C19 C 1.1559(2) 0.3003(2) 0.62405(12) 0.0345(6) Uani 1 1 d . . . . .
H22 H 1.209587 0.305483 0.655645 0.041 Uiso 1 1 calc R U . . .
H21 H 1.191938 0.322527 0.592034 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3378(2) 0.7331(2) 0.73026(11) 0.0332(6) Uani 1 1 d . . . . .
H4 H 0.299580 0.717775 0.694954 0.040 Uiso 1 1 calc R U . . .
H3 H 0.286283 0.721874 0.758619 0.040 Uiso 1 1 calc R U . . .
C4 C 0.5405(2) 0.78452(18) 0.69379(12) 0.0347(6) Uani 1 1 d . . . . .
H7 H 0.585659 0.795362 0.662807 0.042 Uiso 1 1 calc R U . . .
H8 H 0.585193 0.800229 0.727311 0.042 Uiso 1 1 calc R U . . .
C4A C 0.0358(2) 0.79064(19) 0.68829(12) 0.0357(6) Uani 1 1 d . . . . .
H7A H 0.080159 0.798915 0.656777 0.043 Uiso 1 1 calc R U . . .
H8A H 0.081789 0.807366 0.721210 0.043 Uiso 1 1 calc R U . . .
C21A C 0.7177(3) 0.1495(2) 0.63379(12) 0.0382(7) Uani 1 1 d . . . . .
H23A H 0.788995 0.172040 0.644207 0.046 Uiso 1 1 calc R U . . .
C20 C 1.1254(2) 0.2006(2) 0.61577(12) 0.0388(7) Uani 1 1 d . . . . .
C12A C 0.2504(2) 0.7316(2) 0.52858(13) 0.0388(7) Uani 1 1 d . . . . .
H13A H 0.215133 0.760658 0.495794 0.047 Uiso 1 1 calc R U . . .
H12A H 0.215067 0.756974 0.560014 0.047 Uiso 1 1 calc R U . . .
C25A C 0.5289(3) 0.1770(2) 0.60692(13) 0.0415(7) Uani 1 1 d . . . . .
H27A H 0.469786 0.218107 0.598707 0.050 Uiso 1 1 calc R U . . .
C2A C -0.1659(2) 0.7448(2) 0.72748(12) 0.0388(7) Uani 1 1 d . . . . .
H4A H -0.205705 0.727653 0.692870 0.047 Uiso 1 1 calc R U . . .
H3A H -0.216327 0.736206 0.756584 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7739(3) 0.7304(2) 0.53937(12) 0.0400(7) Uani 1 1 d . . . . .
H12 H 0.764875 0.746895 0.577471 0.048 Uiso 1 1 calc R U . . .
H13 H 0.852790 0.735931 0.533167 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4391(3) 0.8443(2) 0.68859(14) 0.0422(7) Uani 1 1 d . . . . .
H6 H 0.461433 0.909523 0.689514 0.051 Uiso 1 1 calc R U . . .
H5 H 0.398761 0.832399 0.653329 0.051 Uiso 1 1 calc R U . . .
C3A C -0.0641(3) 0.8521(2) 0.68270(15) 0.0472(8) Uani 1 1 d . . . . .
H6A H -0.040110 0.916908 0.682540 0.057 Uiso 1 1 calc R U . . .
H5A H -0.105485 0.839405 0.647812 0.057 Uiso 1 1 calc R U . . .
C13A C 0.3684(3) 0.7581(2) 0.53317(13) 0.0433(7) Uani 1 1 d . . . . .
H15A H 0.406164 0.728916 0.503613 0.052 Uiso 1 1 calc R U . . .
H14A H 0.402888 0.735186 0.567833 0.052 Uiso 1 1 calc R U . . .
C23A C 0.5967(3) 0.0228(2) 0.61560(14) 0.0504(8) Uani 1 1 d . . . . .
H25A H 0.584376 -0.041416 0.613053 0.060 Uiso 1 1 calc R U . . .
C22A C 0.6996(3) 0.0555(2) 0.63079(13) 0.0480(8) Uani 1 1 d . . . . .
H24A H 0.758291 0.014054 0.639214 0.058 Uiso 1 1 calc R U . . .
C21 C 1.1981(3) 0.1325(2) 0.63398(13) 0.0530(9) Uani 1 1 d . . . . .
H23 H 1.265928 0.149151 0.652480 0.064 Uiso 1 1 calc R U . . .
C24A C 0.5115(3) 0.0827(2) 0.60408(15) 0.0501(8) Uani 1 1 d . . . . .
H26A H 0.440168 0.059634 0.594123 0.060 Uiso 1 1 calc R U . . .
C13 C 0.7117(3) 0.7964(2) 0.50420(14) 0.0541(9) Uani 1 1 d . . . . .
H15 H 0.633159 0.793199 0.511467 0.065 Uiso 1 1 calc R U . . .
H14 H 0.718255 0.778909 0.466050 0.065 Uiso 1 1 calc R U . . .
C14A C 0.3833(3) 0.8621(2) 0.53037(15) 0.0544(9) Uani 1 1 d . . . . .
H17A H 0.351529 0.884745 0.495570 0.082 Uiso 1 1 calc R U . . .
H18A H 0.461732 0.876929 0.534092 0.082 Uiso 1 1 calc R U . . .
H16A H 0.346229 0.891211 0.559650 0.082 Uiso 1 1 calc R U . . .
C25 C 1.0272(3) 0.1753(3) 0.58807(19) 0.0626(11) Uani 1 1 d . . . . .
H27 H 0.976910 0.221213 0.575070 0.075 Uiso 1 1 calc R U . . .
C22 C 1.1735(5) 0.0404(3) 0.62562(17) 0.0719(14) Uani 1 1 d . . . . .
H24 H 1.223720 -0.005582 0.638557 0.086 Uiso 1 1 calc R U . . .
C14 C 0.7519(5) 0.8951(3) 0.51251(18) 0.0819(15) Uani 1 1 d . . . . .
H16 H 0.738125 0.915285 0.549069 0.123 Uiso 1 1 calc R U . . .
H17 H 0.712457 0.935246 0.486104 0.123 Uiso 1 1 calc R U . . .
H18 H 0.830756 0.898084 0.507691 0.123 Uiso 1 1 calc R U . . .
C23 C 1.0760(5) 0.0164(3) 0.5985(2) 0.0862(17) Uani 1 1 d . . . . .
H25 H 1.058737 -0.046534 0.592858 0.103 Uiso 1 1 calc R U . . .
C24 C 1.0022(4) 0.0833(3) 0.5793(2) 0.0874(16) Uani 1 1 d . . . . .
H26 H 0.935155 0.066270 0.560226 0.105 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2A C10A 1.351(3) . ?
F1 C6 1.355(3) . ?
F2 C10 1.352(3) . ?
F1A C6A 1.353(3) . ?
O3 C18 1.235(3) . ?
O3A C18A 1.235(3) . ?
O2 C17 1.249(3) . ?
O1 C2 1.424(3) . ?
O1 C3 1.426(3) . ?
O2A C17A 1.250(3) . ?
N2A C9A 1.401(3) . ?
N2A C15A 1.355(3) . ?
N2A C11A 1.482(3) . ?
N2 C9 1.399(3) . ?
N2 C15 1.349(3) . ?
N2 C11 1.479(3) . ?
O1A C2A 1.420(4) . ?
O1A C3A 1.426(4) . ?
N1 C5 1.406(3) . ?
N1 C1 1.470(3) . ?
N1 C4 1.478(3) . ?
N3A C18A 1.343(3) . ?
N3A C19A 1.447(3) . ?
N1A C5A 1.405(3) . ?
N1A C1A 1.468(3) . ?
N1A C4A 1.473(3) . ?
N3 C18 1.345(3) . ?
N3 C19 1.449(3) . ?
C9 C8 1.402(3) . ?
C9 C10 1.414(3) . ?
C5 C10 1.393(3) . ?
C5 C6 1.400(4) . ?
C8 C17 1.460(3) . ?
C8 C7 1.399(3) . ?
C15 C16 1.370(3) . ?
C9A C8A 1.407(4) . ?
C9A C10A 1.409(3) . ?
C16 C18 1.487(3) . ?
C16 C17 1.437(3) . ?
C8A C17A 1.461(4) . ?
C8A C7A 1.401(3) . ?
C18A C16A 1.495(3) . ?
C5A C10A 1.391(3) . ?
C5A C6A 1.406(4) . ?
C15A C16A 1.370(4) . ?
C6 C7 1.360(4) . ?
C16A C17A 1.440(3) . ?
C11 C12 1.523(4) . ?
C11A C12A 1.517(4) . ?
C7A C6A 1.360(4) . ?
C19A C20A 1.513(4) . ?
C1 C2 1.508(4) . ?
C20A C21A 1.387(4) . ?
C20A C25A 1.383(4) . ?
C1A C2A 1.510(4) . ?
C19 C20 1.511(4) . ?
C4 C3 1.512(4) . ?
C4A C3A 1.512(4) . ?
C21A C22A 1.389(4) . ?
C20 C21 1.387(4) . ?
C20 C25 1.390(5) . ?
C12A C13A 1.489(4) . ?
C25A C24A 1.393(5) . ?
C12 C13 1.475(4) . ?
C13A C14A 1.529(4) . ?
C23A C22A 1.373(5) . ?
C23A C24A 1.373(5) . ?
C21 C22 1.389(6) . ?
C13 C14 1.530(5) . ?
C25 C24 1.390(6) . ?
C22 C23 1.372(7) . ?
C23 C24 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
C2 O1 C3 109.4(2) . . ?
C9A N2A C11A 123.6(2) . . ?
C15A N2A C9A 119.0(2) . . ?
C15A N2A C11A 117.4(2) . . ?
C9 N2 C11 123.5(2) . . ?
C15 N2 C9 119.1(2) . . ?
C15 N2 C11 117.3(2) . . ?
C2A O1A C3A 109.8(2) . . ?
C5 N1 C1 119.1(2) . . ?
C5 N1 C4 114.7(2) . . ?
C1 N1 C4 109.5(2) . . ?
C18A N3A C19A 122.7(2) . . ?
C5A N1A C1A 119.1(2) . . ?
C5A N1A C4A 114.5(2) . . ?
C1A N1A C4A 109.3(2) . . ?
C18 N3 C19 122.7(2) . . ?
N2 C9 C8 119.2(2) . . ?
N2 C9 C10 124.2(2) . . ?
C8 C9 C10 116.5(2) . . ?
C10 C5 N1 118.4(2) . . ?
C10 C5 C6 115.4(2) . . ?
C6 C5 N1 126.2(2) . . ?
C9 C8 C17 121.8(2) . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 C17 117.9(2) . . ?
N2 C15 C16 125.0(2) . . ?
N2A C9A C8A 118.9(2) . . ?
N2A C9A C10A 124.8(2) . . ?
C8A C9A C10A 116.3(2) . . ?
C15 C16 C18 116.6(2) . . ?
C15 C16 C17 119.4(2) . . ?
C17 C16 C18 123.9(2) . . ?
C9A C8A C17A 122.2(2) . . ?
C7A C8A C9A 120.6(2) . . ?
C7A C8A C17A 117.2(2) . . ?
O3A C18A N3A 123.1(2) . . ?
O3A C18A C16A 121.5(2) . . ?
N3A C18A C16A 115.4(2) . . ?
N1A C5A C6A 126.1(2) . . ?
C10A C5A N1A 118.3(2) . . ?
C10A C5A C6A 115.5(2) . . ?
F2 C10 C9 119.8(2) . . ?
F2 C10 C5 115.9(2) . . ?
C5 C10 C9 124.3(2) . . ?
F2A C10A C9A 119.6(2) . . ?
F2A C10A C5A 116.0(2) . . ?
C5A C10A C9A 124.3(2) . . ?
N2A C15A C16A 125.1(2) . . ?
F1 C6 C5 119.0(2) . . ?
F1 C6 C7 117.9(2) . . ?
C7 C6 C5 123.0(2) . . ?
O3 C18 N3 122.9(2) . . ?
O3 C18 C16 121.9(2) . . ?
N3 C18 C16 115.3(2) . . ?
C15A C16A C18A 116.8(2) . . ?
C15A C16A C17A 119.6(2) . . ?
C17A C16A C18A 123.6(2) . . ?
N2 C11 C12 111.9(2) . . ?
N2A C11A C12A 115.5(2) . . ?
O2 C17 C8 119.7(2) . . ?
O2 C17 C16 124.9(2) . . ?
C16 C17 C8 115.4(2) . . ?
C6 C7 C8 120.2(2) . . ?
O2A C17A C8A 120.2(2) . . ?
O2A C17A C16A 124.7(2) . . ?
C16A C17A C8A 115.1(2) . . ?
C6A C7A C8A 120.0(2) . . ?
N3A C19A C20A 113.9(2) . . ?
F1A C6A C5A 119.1(2) . . ?
F1A C6A C7A 118.1(2) . . ?
C7A C6A C5A 122.8(2) . . ?
N1 C1 C2 107.4(2) . . ?
C21A C20A C19A 118.7(3) . . ?
C25A C20A C19A 122.1(3) . . ?
C25A C20A C21A 119.2(3) . . ?
N1A C1A C2A 107.1(2) . . ?
N3 C19 C20 113.2(2) . . ?
O1 C2 C1 111.1(2) . . ?
N1 C4 C3 109.4(2) . . ?
N1A C4A C3A 109.7(2) . . ?
C20A C21A C22A 120.6(3) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 C25 118.8(3) . . ?
C25 C20 C19 121.2(3) . . ?
C13A C12A C11A 115.6(2) . . ?
C20A C25A C24A 119.9(3) . . ?
O1A C2A C1A 111.3(2) . . ?
C13 C12 C11 114.1(3) . . ?
O1 C3 C4 111.9(3) . . ?
O1A C3A C4A 111.9(3) . . ?
C12A C13A C14A 111.8(3) . . ?
C22A C23A C24A 120.2(3) . . ?
C23A C22A C21A 119.8(3) . . ?
C20 C21 C22 121.1(4) . . ?
C23A C24A C25A 120.4(3) . . ?
C12 C13 C14 112.8(4) . . ?
C20 C25 C24 120.5(4) . . ?
C23 C22 C21 119.5(4) . . ?
C22 C23 C24 120.6(4) . . ?
C25 C24 C23 119.6(5) . . ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_P-1_210K
_database_code_depnum_ccdc_archive 'CCDC 2386810'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   5.3763(2)
_cell_length_b                   13.7145(5)
_cell_length_c                   15.4507(6)
_cell_angle_alpha                94.9970(10)
_cell_angle_beta                 92.1740(10)
_cell_angle_gamma                100.7060(10)
_cell_volume                     1113.44(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9298
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1026 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.9396.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26531
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.464
_diffrn_reflns_theta_min         2.109
_diffrn_ambient_temperature      210(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3449
_reflns_number_total             4591
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.010
_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)+(0.0001P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1231
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C00J-C00T \\sim C00J-C5
 with sigma of 0.02
 C00J-C00U \\sim C00J-C1
 with sigma of 0.02
 C00S-C00V \\sim C3-C2
 with sigma of 0.02
 C00S-C00W \\sim C3-C4
 with sigma of 0.02
 C00T-C00W \\sim C5-C4
 with sigma of 0.02
 C00U-C00V \\sim C1-C2
 with sigma of 0.02
 C00J-C00V \\sim C00J-C2
 with sigma of 0.04
 C00J-C00W \\sim C00J-C4
 with sigma of 0.04
 C00S-C00T \\sim C3-C5
 with sigma of 0.04
 C00S-C00U \\sim C3-C1
 with sigma of 0.04
 C00V-C00W \\sim C2-C4
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C00J: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
2A
4. Rigid body (RIGU) restrains
 C00L, C00J, C00T, C00W, C00S, C00V, C00U
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00J, C5, C4, C3, C2, C1, C00L
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=1-FVAR(1)
 Sof(C00S)=Sof(H00S)=Sof(C00T)=Sof(H00T)=Sof(C00U)=Sof(H00U)=Sof(C00V)=
 Sof(H00V)=Sof(C00W)=Sof(H00W)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00L(H00C,H00D), C00M(H00E,H00F), C00N(H00I,H00J), C00O(H00K,
 H00L), C00P(H00M,H00N), C00Q(H00O,H00P), C00R(H00Q,H00R)
6.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
6.c Idealised Me refined as rotating group:
 C00X(H00X,H00Y,H)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F2 F 0.9910(3) 0.20797(9) 0.70978(9) 0.0579(4) Uani 1 1 d . . . . .
F1 F 1.0876(3) 0.54165(10) 0.65067(9) 0.0565(4) Uani 1 1 d . . . . .
O2 O 0.4039(3) 0.37038(12) 0.43898(10) 0.0513(4) Uani 1 1 d . . . . .
N2 N 0.5652(3) 0.15299(12) 0.58734(10) 0.0390(4) Uani 1 1 d . . . . .
O3 O -0.0450(3) 0.08107(12) 0.41061(11) 0.0590(5) Uani 1 1 d . . . . .
N1 N 1.2016(3) 0.40902(14) 0.75981(11) 0.0423(4) Uani 1 1 d . . . . .
O1 O 1.5819(3) 0.44573(15) 0.89651(12) 0.0669(5) Uani 1 1 d . . . . .
N3 N 0.0028(4) 0.23834(14) 0.37012(11) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.6571(4) 0.32315(15) 0.54980(12) 0.0371(4) Uani 1 1 d . . . . .
C17 C 0.4469(4) 0.30272(15) 0.48383(12) 0.0390(4) Uani 1 1 d . . . . .
C9 C 0.7122(4) 0.24915(15) 0.60073(12) 0.0362(4) Uani 1 1 d . . . . .
C5 C 1.0367(4) 0.37572(15) 0.68602(13) 0.0377(4) Uani 1 1 d . . . . .
C16 C 0.3007(4) 0.20317(15) 0.47658(12) 0.0381(4) Uani 1 1 d . . . . .
C10 C 0.9129(4) 0.27817(15) 0.66456(13) 0.0392(4) Uani 1 1 d . . . . .
C18 C 0.0706(4) 0.16859(16) 0.41625(13) 0.0418(5) Uani 1 1 d . . . . .
C7 C 0.7955(4) 0.42103(16) 0.56431(13) 0.0427(5) Uani 1 1 d . . . . .
H9 H 0.765242 0.469642 0.528039 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3662(4) 0.13507(15) 0.52821(12) 0.0398(5) Uani 1 1 d . . . . .
H19 H 0.265387 0.070817 0.522186 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9738(4) 0.44483(16) 0.63131(13) 0.0419(5) Uani 1 1 d . . . . .
C20 C -0.1327(4) 0.21662(16) 0.21455(14) 0.0452(5) Uani 1 1 d D . . . .
C11 C 0.5868(4) 0.07427(15) 0.64538(14) 0.0448(5) Uani 1 1 d . . . . .
H11 H 0.765247 0.069030 0.653726 0.054 Uiso 1 1 calc R U . . .
H10 H 0.493312 0.010005 0.618211 0.054 Uiso 1 1 calc R U . . .
C19 C -0.2120(4) 0.21912(17) 0.30716(14) 0.0460(5) Uani 1 1 d . . . . .
H22 H -0.313163 0.271126 0.317291 0.055 Uiso 1 1 calc R U . . .
H21 H -0.319325 0.155066 0.315773 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4812(5) 0.09759(18) 0.73355(14) 0.0508(6) Uani 1 1 d . . . . .
H12 H 0.528297 0.169463 0.750245 0.061 Uiso 1 1 calc R U . . .
H13 H 0.295706 0.080411 0.727609 0.061 Uiso 1 1 calc R U . . .
C1 C 1.4676(4) 0.44448(19) 0.74313(15) 0.0501(6) Uani 1 1 d . . . . .
H1 H 1.477870 0.487478 0.695446 0.060 Uiso 1 1 calc R U . . .
H2 H 1.546458 0.387479 0.725437 0.060 Uiso 1 1 calc R U . . .
C4 C 1.1745(5) 0.35460(19) 0.83728(14) 0.0514(6) Uani 1 1 d . . . . .
H7 H 1.240209 0.292744 0.827549 0.062 Uiso 1 1 calc R U . . .
H8 H 0.995046 0.337315 0.849702 0.062 Uiso 1 1 calc R U . . .
C2 C 1.6085(5) 0.5018(2) 0.82334(17) 0.0611(7) Uani 1 1 d . . . . .
H4 H 1.788690 0.520046 0.812266 0.073 Uiso 1 1 calc R U . . .
H3 H 1.544046 0.563515 0.836181 0.073 Uiso 1 1 calc R U . . .
C3 C 1.3208(5) 0.4199(2) 0.91313(16) 0.0648(7) Uani 1 1 d . . . . .
H6 H 1.250901 0.480674 0.923494 0.078 Uiso 1 1 calc R U . . .
H5 H 1.302786 0.384449 0.965634 0.078 Uiso 1 1 calc R U . . .
C13 C 0.5732(6) 0.0430(2) 0.80556(16) 0.0668(7) Uani 1 1 d . . . . .
H15 H 0.758339 0.061094 0.813215 0.080 Uiso 1 1 calc R U . . .
H14 H 0.527907 -0.029045 0.789415 0.080 Uiso 1 1 calc R U . . .
C23 C 0.015(3) 0.2033(13) 0.0438(7) 0.073(3) Uani 0.62(2) 1 d D . P A 1
H25 H 0.060450 0.197411 -0.014349 0.087 Uiso 0.62(2) 1 calc R U P A 1
C21 C -0.196(2) 0.2795(6) 0.1576(4) 0.0557(17) Uani 0.62(2) 1 d D . P A 1
H23 H -0.291096 0.327377 0.176450 0.067 Uiso 0.62(2) 1 calc R U P A 1
C25 C 0.009(2) 0.1463(9) 0.1847(5) 0.072(3) Uani 0.62(2) 1 d D . P A 1
H27 H 0.053637 0.101481 0.222465 0.087 Uiso 0.62(2) 1 calc R U P A 1
C24 C 0.084(3) 0.1419(9) 0.1003(6) 0.087(4) Uani 0.62(2) 1 d D . P A 1
H26 H 0.183964 0.095555 0.081773 0.105 Uiso 0.62(2) 1 calc R U P A 1
C22 C -0.122(2) 0.2747(7) 0.0718(4) 0.070(2) Uani 0.62(2) 1 d D . P A 1
H24 H -0.165031 0.319491 0.033630 0.084 Uiso 0.62(2) 1 calc R U P A 1
C14 C 0.4559(9) 0.0689(3) 0.8913(2) 0.1115(14) Uani 1 1 d . . . . .
H18 H 0.273272 0.047202 0.884785 0.167 Uiso 1 1 calc R U . . .
H16 H 0.496366 0.140384 0.906406 0.167 Uiso 1 1 calc R U . . .
H17 H 0.523561 0.035410 0.937006 0.167 Uiso 1 1 calc R U . . .
H20 H 0.106(5) 0.300(2) 0.3788(18) 0.075(9) Uiso 1 1 d . . . . .
C25A C 0.081(2) 0.1861(13) 0.1867(7) 0.060(3) Uani 0.38(2) 1 d D . P A 2
H27A H 0.194313 0.167774 0.227369 0.072 Uiso 0.38(2) 1 calc R U P A 2
C24A C 0.135(3) 0.1818(16) 0.0994(8) 0.078(4) Uani 0.38(2) 1 d D . P A 2
H26A H 0.274866 0.155170 0.080593 0.093 Uiso 0.38(2) 1 calc R U P A 2
C23A C -0.018(5) 0.2168(17) 0.0405(10) 0.069(4) Uani 0.38(2) 1 d D . P A 2
H25A H 0.025204 0.219435 -0.017761 0.083 Uiso 0.38(2) 1 calc R U P A 2
C22A C -0.232(4) 0.2474(14) 0.0670(7) 0.083(4) Uani 0.38(2) 1 d D . P A 2
H24A H -0.341164 0.267419 0.026142 0.099 Uiso 0.38(2) 1 calc R U P A 2
C21A C -0.289(3) 0.2495(12) 0.1538(6) 0.059(3) Uani 0.38(2) 1 d D . P A 2
H23A H -0.434192 0.273185 0.171771 0.071 Uiso 0.38(2) 1 calc R U P A 2


_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
F2 C10 1.355(2) . ?
F1 C6 1.357(2) . ?
O2 C17 1.255(2) . ?
N2 C9 1.400(3) . ?
N2 C15 1.352(3) . ?
N2 C11 1.480(3) . ?
O3 C18 1.239(3) . ?
N1 C5 1.406(2) . ?
N1 C1 1.462(3) . ?
N1 C4 1.463(3) . ?
O1 C2 1.419(3) . ?
O1 C3 1.421(3) . ?
N3 C18 1.336(3) . ?
N3 C19 1.451(3) . ?
N3 H20 0.91(3) . ?
C8 C17 1.463(3) . ?
C8 C9 1.404(3) . ?
C8 C7 1.404(3) . ?
C17 C16 1.436(3) . ?
C9 C10 1.409(3) . ?
C5 C10 1.385(3) . ?
C5 C6 1.402(3) . ?
C16 C18 1.497(3) . ?
C16 C15 1.365(3) . ?
C7 H9 0.9400 . ?
C7 C6 1.359(3) . ?
C15 H19 0.9400 . ?
C20 C19 1.508(3) . ?
C20 C21 1.360(6) . ?
C20 C25 1.394(6) . ?
C20 C25A 1.367(10) . ?
C20 C21A 1.396(9) . ?
C11 H11 0.9800 . ?
C11 H10 0.9800 . ?
C11 C12 1.527(3) . ?
C19 H22 0.9800 . ?
C19 H21 0.9800 . ?
C12 H12 0.9800 . ?
C12 H13 0.9800 . ?
C12 C13 1.512(3) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 C2 1.505(3) . ?
C4 H7 0.9800 . ?
C4 H8 0.9800 . ?
C4 C3 1.510(3) . ?
C2 H4 0.9800 . ?
C2 H3 0.9800 . ?
C3 H6 0.9800 . ?
C3 H5 0.9800 . ?
C13 H15 0.9800 . ?
C13 H14 0.9800 . ?
C13 C14 1.531(4) . ?
C23 H25 0.9400 . ?
C23 C24 1.351(9) . ?
C23 C22 1.381(10) . ?
C21 H23 0.9400 . ?
C21 C22 1.398(7) . ?
C25 H27 0.9400 . ?
C25 C24 1.379(7) . ?
C24 H26 0.9400 . ?
C22 H24 0.9400 . ?
C14 H18 0.9700 . ?
C14 H16 0.9700 . ?
C14 H17 0.9700 . ?
C25A H27A 0.9400 . ?
C25A C24A 1.388(11) . ?
C24A H26A 0.9400 . ?
C24A C23A 1.379(13) . ?
C23A H25A 0.9400 . ?
C23A C22A 1.359(14) . ?
C22A H24A 0.9400 . ?
C22A C21A 1.387(11) . ?
C21A H23A 0.9400 . ?

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
C9 N2 C11 122.97(16) . . ?
C15 N2 C9 118.92(17) . . ?
C15 N2 C11 117.17(17) . . ?
C5 N1 C1 116.06(17) . . ?
C5 N1 C4 119.81(17) . . ?
C1 N1 C4 112.03(18) . . ?
C2 O1 C3 109.4(2) . . ?
C18 N3 C19 123.48(19) . . ?
C18 N3 H20 115.3(18) . . ?
C19 N3 H20 121.1(18) . . ?
C9 C8 C17 121.60(18) . . ?
C7 C8 C17 117.94(19) . . ?
C7 C8 C9 120.37(18) . . ?
O2 C17 C8 119.99(18) . . ?
O2 C17 C16 124.70(19) . . ?
C16 C17 C8 115.31(18) . . ?
N2 C9 C8 119.34(17) . . ?
N2 C9 C10 123.91(18) . . ?
C8 C9 C10 116.74(18) . . ?
C10 C5 N1 124.99(19) . . ?
C10 C5 C6 115.19(18) . . ?
C6 C5 N1 119.68(18) . . ?
C17 C16 C18 123.69(18) . . ?
C15 C16 C17 119.75(18) . . ?
C15 C16 C18 116.54(18) . . ?
F2 C10 C9 119.31(18) . . ?
F2 C10 C5 116.54(18) . . ?
C5 C10 C9 124.14(19) . . ?
O3 C18 N3 123.6(2) . . ?
O3 C18 C16 121.22(19) . . ?
N3 C18 C16 115.20(18) . . ?
C8 C7 H9 120.3 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H9 120.3 . . ?
N2 C15 C16 124.99(19) . . ?
N2 C15 H19 117.5 . . ?
C16 C15 H19 117.5 . . ?
F1 C6 C5 117.25(18) . . ?
F1 C6 C7 118.95(19) . . ?
C7 C6 C5 123.66(19) . . ?
C21 C20 C19 123.0(3) . . ?
C21 C20 C25 117.8(5) . . ?
C25 C20 C19 119.2(4) . . ?
C25A C20 C19 124.8(5) . . ?
C25A C20 C21A 118.3(7) . . ?
C21A C20 C19 116.8(6) . . ?
N2 C11 H11 109.5 . . ?
N2 C11 H10 109.5 . . ?
N2 C11 C12 110.90(17) . . ?
H11 C11 H10 108.0 . . ?
C12 C11 H11 109.5 . . ?
C12 C11 H10 109.5 . . ?
N3 C19 C20 112.56(18) . . ?
N3 C19 H22 109.1 . . ?
N3 C19 H21 109.1 . . ?
C20 C19 H22 109.1 . . ?
C20 C19 H21 109.1 . . ?
H22 C19 H21 107.8 . . ?
C11 C12 H12 108.7 . . ?
C11 C12 H13 108.7 . . ?
H12 C12 H13 107.6 . . ?
C13 C12 C11 114.1(2) . . ?
C13 C12 H12 108.7 . . ?
C13 C12 H13 108.7 . . ?
N1 C1 H1 109.5 . . ?
N1 C1 H2 109.5 . . ?
N1 C1 C2 110.60(19) . . ?
H1 C1 H2 108.1 . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H2 109.5 . . ?
N1 C4 H7 110.0 . . ?
N1 C4 H8 110.0 . . ?
N1 C4 C3 108.7(2) . . ?
H7 C4 H8 108.3 . . ?
C3 C4 H7 110.0 . . ?
C3 C4 H8 110.0 . . ?
O1 C2 C1 111.9(2) . . ?
O1 C2 H4 109.2 . . ?
O1 C2 H3 109.2 . . ?
C1 C2 H4 109.2 . . ?
C1 C2 H3 109.2 . . ?
H4 C2 H3 107.9 . . ?
O1 C3 C4 110.9(2) . . ?
O1 C3 H6 109.5 . . ?
O1 C3 H5 109.5 . . ?
C4 C3 H6 109.5 . . ?
C4 C3 H5 109.5 . . ?
H6 C3 H5 108.1 . . ?
C12 C13 H15 109.4 . . ?
C12 C13 H14 109.4 . . ?
C12 C13 C14 111.0(2) . . ?
H15 C13 H14 108.0 . . ?
C14 C13 H15 109.4 . . ?
C14 C13 H14 109.4 . . ?
C24 C23 H25 120.1 . . ?
C24 C23 C22 119.7(8) . . ?
C22 C23 H25 120.1 . . ?
C20 C21 H23 119.1 . . ?
C20 C21 C22 121.7(6) . . ?
C22 C21 H23 119.1 . . ?
C20 C25 H27 119.7 . . ?
C24 C25 C20 120.6(6) . . ?
C24 C25 H27 119.7 . . ?
C23 C24 C25 120.9(7) . . ?
C23 C24 H26 119.5 . . ?
C25 C24 H26 119.5 . . ?
C23 C22 C21 119.1(7) . . ?
C23 C22 H24 120.5 . . ?
C21 C22 H24 120.5 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H17 109.5 . . ?
H18 C14 H16 109.5 . . ?
H18 C14 H17 109.5 . . ?
H16 C14 H17 109.5 . . ?
C20 C25A H27A 119.4 . . ?
C20 C25A C24A 121.3(10) . . ?
C24A C25A H27A 119.4 . . ?
C25A C24A H26A 120.2 . . ?
C23A C24A C25A 119.6(12) . . ?
C23A C24A H26A 120.2 . . ?
C24A C23A H25A 120.2 . . ?
C22A C23A C24A 119.7(13) . . ?
C22A C23A H25A 120.2 . . ?
C23A C22A H24A 119.7 . . ?
C23A C22A C21A 120.7(11) . . ?
C21A C22A H24A 119.7 . . ?
C20 C21A H23A 119.9 . . ?
C22A C21A C20 120.1(10) . . ?
C22A C21A H23A 119.9 . . ?

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
O2 C17 C16 C18 -2.4(3) . . . . ?
O2 C17 C16 C15 179.3(2) . . . . ?
N2 C9 C10 F2 7.9(3) . . . . ?
N2 C9 C10 C5 -170.99(19) . . . . ?
N2 C11 C12 C13 -160.2(2) . . . . ?
N1 C5 C10 F2 -11.9(3) . . . . ?
N1 C5 C10 C9 167.02(19) . . . . ?
N1 C5 C6 F1 3.2(3) . . . . ?
N1 C5 C6 C7 -172.54(19) . . . . ?
N1 C1 C2 O1 54.2(3) . . . . ?
N1 C4 C3 O1 -59.7(3) . . . . ?
C8 C17 C16 C18 176.93(18) . . . . ?
C8 C17 C16 C15 -1.4(3) . . . . ?
C8 C9 C10 F2 -173.54(17) . . . . ?
C8 C9 C10 C5 7.6(3) . . . . ?
C8 C7 C6 F1 -173.06(18) . . . . ?
C8 C7 C6 C5 2.6(3) . . . . ?
C17 C8 C9 N2 1.0(3) . . . . ?
C17 C8 C9 C10 -177.65(18) . . . . ?
C17 C8 C7 C6 172.99(19) . . . . ?
C17 C16 C18 O3 177.9(2) . . . . ?
C17 C16 C18 N3 -1.9(3) . . . . ?
C17 C16 C15 N2 -0.7(3) . . . . ?
C9 N2 C15 C16 2.9(3) . . . . ?
C9 N2 C11 C12 70.3(3) . . . . ?
C9 C8 C17 O2 -179.50(19) . . . . ?
C9 C8 C17 C16 1.2(3) . . . . ?
C9 C8 C7 C6 -3.7(3) . . . . ?
C5 N1 C1 C2 165.3(2) . . . . ?
C5 N1 C4 C3 -164.5(2) . . . . ?
C10 C5 C6 F1 179.00(18) . . . . ?
C10 C5 C6 C7 3.3(3) . . . . ?
C18 N3 C19 C20 -106.3(2) . . . . ?
C18 C16 C15 N2 -179.05(18) . . . . ?
C7 C8 C17 O2 3.9(3) . . . . ?
C7 C8 C17 C16 -175.48(18) . . . . ?
C7 C8 C9 N2 177.53(18) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C15 N2 C9 C8 -2.9(3) . . . . ?
C15 N2 C9 C10 175.56(19) . . . . ?
C15 N2 C11 C12 -98.5(2) . . . . ?
C15 C16 C18 O3 -3.7(3) . . . . ?
C15 C16 C18 N3 176.39(19) . . . . ?
C6 C5 C10 F2 172.53(18) . . . . ?
C6 C5 C10 C9 -8.5(3) . . . . ?
C20 C21 C22 C23 1.0(12) . . . . ?
C20 C25 C24 C23 -2.2(16) . . . . ?
C20 C25A C24A C23A 6(2) . . . . ?
C11 N2 C9 C8 -171.56(18) . . . . ?
C11 N2 C9 C10 6.9(3) . . . . ?
C11 N2 C15 C16 172.16(19) . . . . ?
C11 C12 C13 C14 -179.0(3) . . . . ?
C19 N3 C18 O3 -1.0(4) . . . . ?
C19 N3 C18 C16 178.92(19) . . . . ?
C19 C20 C21 C22 -179.2(4) . . . . ?
C19 C20 C25 C24 179.8(7) . . . . ?
C19 C20 C25A C24A 177.0(9) . . . . ?
C19 C20 C21A C22A -178.6(8) . . . . ?
C1 N1 C5 C10 113.6(2) . . . . ?
C1 N1 C5 C6 -71.1(3) . . . . ?
C1 N1 C4 C3 54.4(3) . . . . ?
C4 N1 C5 C10 -26.0(3) . . . . ?
C4 N1 C5 C6 149.3(2) . . . . ?
C4 N1 C1 C2 -52.1(3) . . . . ?
C2 O1 C3 C4 62.4(3) . . . . ?
C3 O1 C2 C1 -59.4(3) . . . . ?
C21 C20 C19 N3 -120.6(6) . . . . ?
C21 C20 C25 C24 0.6(10) . . . . ?
C25 C20 C19 N3 60.3(8) . . . . ?
C25 C20 C21 C22 -0.1(7) . . . . ?
C24 C23 C22 C21 -2(2) . . . . ?
C22 C23 C24 C25 3(2) . . . . ?
C25A C20 C19 N3 31.0(9) . . . . ?
C25A C20 C21A C22A 2.3(12) . . . . ?
C25A C24A C23A C22A -5(3) . . . . ?
C24A C23A C22A C21A 4(3) . . . . ?
C23A C22A C21A C20 -2(2) . . . . ?
C21A C20 C19 N3 -148.0(8) . . . . ?
C21A C20 C25A C24A -4.0(13) . . . . ?

_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_P21_c_130K
_database_code_depnum_ccdc_archive 'CCDC 2386806'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-02-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2086(3)
_cell_length_b                   14.5790(4)
_cell_length_c                   24.8022(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.0640(10)
_cell_angle_gamma                90
_cell_volume                     4403.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9662
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7168
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0973 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.9616.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            59029
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.159
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                   xray
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6502
_reflns_number_total             9034
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     605
_refine_ls_number_reflns         9034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.060
_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)+(0.0781P)²+4.7680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00W(H00C,H00D), C00X(H00A,H00B), C012(H01A,H01B), C014(H01W,H01X), C015(H01Y,
 H), C017(H01C,H01D), C018(H01Z,HA), C019(H01,HB), C01B(H01F,H01G), C01C(H01H,
 H01I), C01F(H1,HC), C01G(H01K,H01L), C01H(H01M,H01N), C01I(H2,HD), C01J(H01O,
 H01P), C01O(H4,HE)
2.b Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00Q(H00Q), C00Z(H00Z), C011(H011), C01A(H01E), C01E(H01J),
 C01K(H01Q), C01L(H01R), C01M(H01S), C01N(H3), C01Q(H5), C01R(H6), C01T(H8),
 C01U(H9)
2.c Idealised Me refined as rotating group:
 C01P(H01T,H01U,H01V), C01S(H7,HF,HG)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F2A F 0.92736(9) 0.67521(8) 0.40648(5) 0.0273(3) Uani 1 1 d . . . . .
F1 F 0.39681(10) 0.56259(9) 0.22364(5) 0.0286(3) Uani 1 1 d . . . . .
F2 F 0.41368(10) 0.67500(9) 0.40165(5) 0.0288(3) Uani 1 1 d . . . . .
F1A F 0.90625(10) 0.57071(9) 0.22664(5) 0.0320(3) Uani 1 1 d . . . . .
O3 O -0.05339(12) 0.42139(11) 0.45110(6) 0.0312(4) Uani 1 1 d . . . . .
O3A O 0.44840(13) 0.43076(11) 0.45027(6) 0.0330(4) Uani 1 1 d . . . . .
O2 O 0.09078(13) 0.40630(12) 0.30160(6) 0.0361(4) Uani 1 1 d . . . . .
O1 O 0.63196(12) 0.82713(11) 0.26918(7) 0.0326(4) Uani 1 1 d . . . . .
O2A O 0.59848(14) 0.41464(12) 0.30249(6) 0.0385(4) Uani 1 1 d . . . . .
N2 N 0.22163(13) 0.57148(11) 0.42372(6) 0.0191(3) Uani 1 1 d . . . . .
N2A N 0.73021(13) 0.57594(11) 0.42684(6) 0.0205(3) Uani 1 1 d . . . . .
O1A O 1.13476(13) 0.83936(12) 0.27487(7) 0.0406(4) Uani 1 1 d . . . . .
N1 N 0.49248(13) 0.68685(11) 0.30489(7) 0.0219(4) Uani 1 1 d . . . . .
N3A N 0.44084(14) 0.36795(12) 0.36646(7) 0.0246(4) Uani 1 1 d . . . . .
N1A N 0.99980(13) 0.69469(12) 0.30862(7) 0.0243(4) Uani 1 1 d . . . . .
N3 N -0.06324(14) 0.35802(13) 0.36728(7) 0.0261(4) Uani 1 1 d . . . . .
C8 C 0.22587(15) 0.51193(13) 0.33307(7) 0.0197(4) Uani 1 1 d . . . . .
C15 C 0.12983(15) 0.52211(13) 0.42944(7) 0.0194(4) Uani 1 1 d . . . . .
H19 H 0.096302 0.527271 0.462721 0.023 Uiso 1 1 calc R U . . .
C9 C 0.27088(15) 0.56875(13) 0.37455(7) 0.0191(4) Uani 1 1 d . . . . .
C9A C 0.78106(15) 0.57351(13) 0.37800(7) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.40749(15) 0.62421(13) 0.31261(8) 0.0198(4) Uani 1 1 d . . . . .
C16 C 0.08109(15) 0.46497(13) 0.39085(7) 0.0201(4) Uani 1 1 d . . . . .
C5A C 0.91666(15) 0.63039(14) 0.31613(8) 0.0218(4) Uani 1 1 d . . . . .
C8A C 0.73555(16) 0.51781(14) 0.33583(8) 0.0222(4) Uani 1 1 d . . . . .
C18A C 0.48641(16) 0.42215(14) 0.40570(8) 0.0222(4) Uani 1 1 d . . . . .
C15A C 0.63721(15) 0.52708(13) 0.43140(8) 0.0206(4) Uani 1 1 d . . . . .
H19A H 0.603097 0.531528 0.464556 0.025 Uiso 1 1 calc R U . . .
C10A C 0.87433(15) 0.62499(13) 0.36681(8) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.36369(15) 0.62096(13) 0.36296(8) 0.0207(4) Uani 1 1 d . . . . .
C18 C -0.01749(16) 0.41361(14) 0.40597(8) 0.0223(4) Uani 1 1 d . . . . .
C6 C 0.35933(16) 0.56370(14) 0.27369(8) 0.0217(4) Uani 1 1 d . . . . .
C16A C 0.58811(16) 0.47167(13) 0.39213(8) 0.0218(4) Uani 1 1 d . . . . .
C11 C 0.26065(16) 0.63091(14) 0.46948(8) 0.0234(4) Uani 1 1 d . . . . .
H11 H 0.341758 0.627752 0.474274 0.028 Uiso 1 1 calc R U . . .
H10 H 0.230812 0.608000 0.503042 0.028 Uiso 1 1 calc R U . . .
C11A C 0.77306(16) 0.62930(14) 0.47476(8) 0.0224(4) Uani 1 1 d . . . . .
H10A H 0.853421 0.619723 0.479753 0.027 Uiso 1 1 calc R U . . .
H11A H 0.740326 0.604345 0.507081 0.027 Uiso 1 1 calc R U . . .
C17 C 0.12804(16) 0.45624(14) 0.33953(8) 0.0221(4) Uani 1 1 d . . . . .
C7 C 0.27297(16) 0.50828(14) 0.28325(8) 0.0226(4) Uani 1 1 d . . . . .
H9 H 0.244627 0.467079 0.256049 0.027 Uiso 1 1 calc R U . . .
C17A C 0.63599(17) 0.46314(14) 0.34100(8) 0.0244(4) Uani 1 1 d . . . . .
C7A C 0.78282(16) 0.51460(14) 0.28590(8) 0.0248(4) Uani 1 1 d . . . . .
H9A H 0.754873 0.473505 0.258556 0.030 Uiso 1 1 calc R U . . .
C19A C 0.34423(16) 0.31281(14) 0.37329(8) 0.0247(4) Uani 1 1 d . . . . .
H22A H 0.290604 0.323262 0.342059 0.030 Uiso 1 1 calc R U . . .
H21A H 0.309997 0.333526 0.406192 0.030 Uiso 1 1 calc R U . . .
C6A C 0.86894(16) 0.57061(14) 0.27677(8) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.56295(16) 0.67194(15) 0.26000(8) 0.0252(4) Uani 1 1 d . . . . .
H1 H 0.522724 0.687688 0.225168 0.030 Uiso 1 1 calc R U . . .
H2 H 0.585635 0.606821 0.258735 0.030 Uiso 1 1 calc R U . . .
C19 C -0.15642(17) 0.29955(15) 0.37606(9) 0.0286(5) Uani 1 1 d . . . . .
H22 H -0.210276 0.304183 0.344402 0.034 Uiso 1 1 calc R U . . .
H21 H -0.192505 0.321962 0.408054 0.034 Uiso 1 1 calc R U . . .
C20A C 0.36744(17) 0.21108(14) 0.37808(8) 0.0249(4) Uani 1 1 d . . . . .
C1A C 1.06783(16) 0.68398(16) 0.26252(8) 0.0288(5) Uani 1 1 d . . . . .
H2A H 1.025741 0.701774 0.228542 0.035 Uiso 1 1 calc R U . . .
H1A H 1.091429 0.619359 0.259349 0.035 Uiso 1 1 calc R U . . .
C2 C 0.66248(16) 0.73293(15) 0.26968(9) 0.0276(4) Uani 1 1 d . . . . .
H3 H 0.700842 0.717610 0.305036 0.033 Uiso 1 1 calc R U . . .
H4 H 0.713876 0.721683 0.241257 0.033 Uiso 1 1 calc R U . . .
C4 C 0.45976(17) 0.78439(14) 0.30620(9) 0.0290(5) Uani 1 1 d . . . . .
H7 H 0.414699 0.795355 0.337219 0.035 Uiso 1 1 calc R U . . .
H8 H 0.415060 0.800138 0.272613 0.035 Uiso 1 1 calc R U . . .
C21A C 0.28175(19) 0.14977(16) 0.36622(9) 0.0316(5) Uani 1 1 d . . . . .
H23A H 0.210280 0.172311 0.355975 0.038 Uiso 1 1 calc R U . . .
C4A C 0.96479(17) 0.79132(15) 0.31245(9) 0.0299(5) Uani 1 1 d . . . . .
H8A H 0.920923 0.799283 0.344200 0.036 Uiso 1 1 calc R U . . .
H7A H 0.918273 0.808361 0.279663 0.036 Uiso 1 1 calc R U . . .
C12A C 0.75091(18) 0.73172(15) 0.47208(9) 0.0307(5) Uani 1 1 d . . . . .
H13A H 0.785912 0.760593 0.505076 0.037 Uiso 1 1 calc R U . . .
H12A H 0.786638 0.757226 0.440754 0.037 Uiso 1 1 calc R U . . .
C20 C -0.12513(19) 0.19973(16) 0.38475(9) 0.0332(5) Uani 1 1 d . . . . .
C25A C 0.47114(18) 0.17729(16) 0.39284(9) 0.0334(5) Uani 1 1 d . . . . .
H27A H 0.530331 0.218440 0.401017 0.040 Uiso 1 1 calc R U . . .
C12 C 0.22560(19) 0.73044(15) 0.46034(9) 0.0323(5) Uani 1 1 d . . . . .
H12 H 0.234564 0.746848 0.422174 0.039 Uiso 1 1 calc R U . . .
H13 H 0.146696 0.736184 0.466595 0.039 Uiso 1 1 calc R U . . .
C13A C 0.63138(18) 0.75836(16) 0.46710(10) 0.0332(5) Uani 1 1 d . . . . .
H15A H 0.593350 0.729136 0.496589 0.040 Uiso 1 1 calc R U . . .
H14A H 0.597177 0.735470 0.432287 0.040 Uiso 1 1 calc R U . . .
C2A C 1.16655(17) 0.74571(17) 0.27277(9) 0.0330(5) Uani 1 1 d . . . . .
H4A H 1.206484 0.728393 0.307413 0.040 Uiso 1 1 calc R U . . .
H3A H 1.216930 0.737228 0.243602 0.040 Uiso 1 1 calc R U . . .
C3 C 0.56129(19) 0.84399(16) 0.31140(10) 0.0351(5) Uani 1 1 d . . . . .
H6 H 0.539075 0.909309 0.310534 0.042 Uiso 1 1 calc R U . . .
H5 H 0.601785 0.832028 0.346706 0.042 Uiso 1 1 calc R U . . .
C3A C 1.0648(2) 0.85266(17) 0.31794(11) 0.0401(6) Uani 1 1 d . . . . .
H6A H 1.040929 0.917537 0.318303 0.048 Uiso 1 1 calc R U . . .
H5A H 1.106612 0.839763 0.352784 0.048 Uiso 1 1 calc R U . . .
C23A C 0.4032(2) 0.02286(17) 0.38411(10) 0.0417(6) Uani 1 1 d . . . . .
H25A H 0.415526 -0.041404 0.386369 0.050 Uiso 1 1 calc R U . . .
C24A C 0.4888(2) 0.08303(18) 0.39572(11) 0.0409(6) Uani 1 1 d . . . . .
H26A H 0.560170 0.060041 0.405736 0.049 Uiso 1 1 calc R U . . .
C22A C 0.3000(2) 0.05589(17) 0.36927(10) 0.0397(6) Uani 1 1 d . . . . .
H24A H 0.241164 0.014427 0.361078 0.048 Uiso 1 1 calc R U . . .
C21 C -0.1966(2) 0.13113(18) 0.36599(10) 0.0452(7) Uani 1 1 d . . . . .
H23 H -0.263930 0.147136 0.346771 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2892(2) 0.79679(17) 0.49608(10) 0.0428(6) Uani 1 1 d . . . . .
H15 H 0.367732 0.793328 0.488711 0.051 Uiso 1 1 calc R U . . .
H14 H 0.282818 0.779160 0.534280 0.051 Uiso 1 1 calc R U . . .
C14A C 0.6168(2) 0.86227(17) 0.46991(11) 0.0420(6) Uani 1 1 d . . . . .
H16A H 0.654145 0.891349 0.440683 0.063 Uiso 1 1 calc R U . . .
H17A H 0.648427 0.884837 0.504832 0.063 Uiso 1 1 calc R U . . .
H18A H 0.538362 0.877275 0.466021 0.063 Uiso 1 1 calc R U . . .
C25 C -0.0271(2) 0.17528(19) 0.41293(14) 0.0521(7) Uani 1 1 d . . . . .
H27 H 0.022711 0.221606 0.426013 0.062 Uiso 1 1 calc R U . . .
C22 C -0.1710(3) 0.0393(2) 0.37489(12) 0.0615(9) Uani 1 1 d . . . . .
H24 H -0.220603 -0.007110 0.361733 0.074 Uiso 1 1 calc R U . . .
C14 C 0.2493(3) 0.89526(19) 0.48780(13) 0.0634(9) Uani 1 1 d . . . . .
H16 H 0.258443 0.914008 0.450443 0.095 Uiso 1 1 calc R U . . .
H17 H 0.292329 0.935932 0.512620 0.095 Uiso 1 1 calc R U . . .
H18 H 0.171571 0.899102 0.495027 0.095 Uiso 1 1 calc R U . . .
C23 C -0.0734(3) 0.0157(2) 0.40290(16) 0.0706(11) Uani 1 1 d . . . . .
H25 H -0.055737 -0.047108 0.409030 0.085 Uiso 1 1 calc R U . . .
C24 C -0.0013(3) 0.0833(2) 0.42210(17) 0.0713(10) Uani 1 1 d . . . . .
H26 H 0.065803 0.067040 0.441504 0.086 Uiso 1 1 calc R U . . .
H20 H -0.031(2) 0.3591(19) 0.3344(12) 0.044(7) Uiso 1 1 d . . . . .
H20A H 0.473(2) 0.3683(18) 0.3346(11) 0.036(7) Uiso 1 1 d . . . . .


_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
F2A C10A 1.354(2) . ?
F1 C6 1.353(2) . ?
F2 C10 1.353(2) . ?
F1A C6A 1.354(2) . ?
O3 C18 1.236(2) . ?
O3A C18A 1.235(2) . ?
O2 C17 1.250(2) . ?
O1 C2 1.423(3) . ?
O1 C3 1.425(3) . ?
O2A C17A 1.249(3) . ?
N2 C15 1.348(2) . ?
N2 C9 1.398(2) . ?
N2 C11 1.480(2) . ?
N2A C9A 1.400(2) . ?
N2A C15A 1.352(2) . ?
N2A C11A 1.484(2) . ?
O1A C2A 1.422(3) . ?
O1A C3A 1.427(3) . ?
N1 C5 1.405(2) . ?
N1 C1 1.471(2) . ?
N1 C4 1.478(3) . ?
N3A C18A 1.343(3) . ?
N3A C19A 1.447(3) . ?
N3A H20A 0.91(3) . ?
N1A C5A 1.404(3) . ?
N1A C1A 1.468(2) . ?
N1A C4A 1.477(3) . ?
N3 C18 1.347(3) . ?
N3 C19 1.450(3) . ?
N3 H20 0.93(3) . ?
C8 C9 1.402(3) . ?
C8 C17 1.462(3) . ?
C8 C7 1.400(3) . ?
C15 H19 0.9500 . ?
C15 C16 1.372(3) . ?
C9 C10 1.411(3) . ?
C9A C8A 1.407(3) . ?
C9A C10A 1.408(3) . ?
C5 C10 1.394(3) . ?
C5 C6 1.405(3) . ?
C16 C18 1.488(3) . ?
C16 C17 1.438(3) . ?
C5A C10A 1.395(3) . ?
C5A C6A 1.404(3) . ?
C8A C17A 1.467(3) . ?
C8A C7A 1.404(3) . ?
C18A C16A 1.495(3) . ?
C15A H19A 0.9500 . ?
C15A C16A 1.370(3) . ?
C6 C7 1.362(3) . ?
C16A C17A 1.439(3) . ?
C11 H11 0.9900 . ?
C11 H10 0.9900 . ?
C11 C12 1.525(3) . ?
C11A H10A 0.9900 . ?
C11A H11A 0.9900 . ?
C11A C12A 1.518(3) . ?
C7 H9 0.9500 . ?
C7A H9A 0.9500 . ?
C7A C6A 1.363(3) . ?
C19A H22A 0.9900 . ?
C19A H21A 0.9900 . ?
C19A C20A 1.513(3) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C1 C2 1.511(3) . ?
C19 H22 0.9900 . ?
C19 H21 0.9900 . ?
C19 C20 1.516(3) . ?
C20A C21A 1.392(3) . ?
C20A C25A 1.383(3) . ?
C1A H2A 0.9900 . ?
C1A H1A 0.9900 . ?
C1A C2A 1.511(3) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
C4 H7 0.9900 . ?
C4 H8 0.9900 . ?
C4 C3 1.512(3) . ?
C21A H23A 0.9500 . ?
C21A C22A 1.388(3) . ?
C4A H8A 0.9900 . ?
C4A H7A 0.9900 . ?
C4A C3A 1.512(3) . ?
C12A H13A 0.9900 . ?
C12A H12A 0.9900 . ?
C12A C13A 1.507(3) . ?
C20 C21 1.386(3) . ?
C20 C25 1.390(4) . ?
C25A H27A 0.9500 . ?
C25A C24A 1.392(3) . ?
C12 H12 0.9900 . ?
C12 H13 0.9900 . ?
C12 C13 1.492(3) . ?
C13A H15A 0.9900 . ?
C13A H14A 0.9900 . ?
C13A C14A 1.527(3) . ?
C2A H4A 0.9900 . ?
C2A H3A 0.9900 . ?
C3 H6 0.9900 . ?
C3 H5 0.9900 . ?
C3A H6A 0.9900 . ?
C3A H5A 0.9900 . ?
C23A H25A 0.9500 . ?
C23A C24A 1.379(4) . ?
C23A C22A 1.374(4) . ?
C24A H26A 0.9500 . ?
C22A H24A 0.9500 . ?
C21 H23 0.9500 . ?
C21 C22 1.389(4) . ?
C13 H15 0.9900 . ?
C13 H14 0.9900 . ?
C13 C14 1.525(4) . ?
C14A H16A 0.9800 . ?
C14A H17A 0.9800 . ?
C14A H18A 0.9800 . ?
C25 H27 0.9500 . ?
C25 C24 1.392(4) . ?
C22 H24 0.9500 . ?
C22 C23 1.380(5) . ?
C14 H16 0.9800 . ?
C14 H17 0.9800 . ?
C14 H18 0.9800 . ?
C23 H25 0.9500 . ?
C23 C24 1.385(5) . ?
C24 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.40(15) . . ?
C15 N2 C9 119.26(16) . . ?
C15 N2 C11 117.18(15) . . ?
C9 N2 C11 123.43(16) . . ?
C9A N2A C11A 123.59(16) . . ?
C15A N2A C9A 119.04(16) . . ?
C15A N2A C11A 117.36(15) . . ?
C2A O1A C3A 109.71(16) . . ?
C5 N1 C1 118.96(16) . . ?
C5 N1 C4 114.76(15) . . ?
C1 N1 C4 109.41(15) . . ?
C18A N3A C19A 122.76(17) . . ?
C18A N3A H20A 116.3(17) . . ?
C19A N3A H20A 120.9(17) . . ?
C5A N1A C1A 119.11(17) . . ?
C5A N1A C4A 114.41(16) . . ?
C1A N1A C4A 109.49(16) . . ?
C18 N3 C19 122.47(17) . . ?
C18 N3 H20 115.9(17) . . ?
C19 N3 H20 121.7(17) . . ?
C9 C8 C17 121.88(17) . . ?
C7 C8 C9 120.38(18) . . ?
C7 C8 C17 117.73(17) . . ?
N2 C15 H19 117.5 . . ?
N2 C15 C16 124.99(17) . . ?
C16 C15 H19 117.5 . . ?
N2 C9 C8 119.11(17) . . ?
N2 C9 C10 124.30(17) . . ?
C8 C9 C10 116.59(17) . . ?
N2A C9A C8A 118.80(17) . . ?
N2A C9A C10A 124.85(18) . . ?
C8A C9A C10A 116.33(17) . . ?
C10 C5 N1 118.55(17) . . ?
C10 C5 C6 115.19(17) . . ?
C6 C5 N1 126.25(17) . . ?
C15 C16 C18 116.63(17) . . ?
C15 C16 C17 119.39(17) . . ?
C17 C16 C18 123.97(17) . . ?
N1A C5A C6A 126.20(17) . . ?
C10A C5A N1A 118.35(18) . . ?
C10A C5A C6A 115.45(17) . . ?
C9A C8A C17A 122.32(17) . . ?
C7A C8A C9A 120.64(18) . . ?
C7A C8A C17A 117.01(18) . . ?
O3A C18A N3A 123.06(18) . . ?
O3A C18A C16A 121.54(18) . . ?
N3A C18A C16A 115.39(17) . . ?
N2A C15A H19A 117.3 . . ?
N2A C15A C16A 125.38(17) . . ?
C16A C15A H19A 117.3 . . ?
F2A C10A C9A 119.79(16) . . ?
F2A C10A C5A 115.84(17) . . ?
C5A C10A C9A 124.35(18) . . ?
F2 C10 C9 119.84(16) . . ?
F2 C10 C5 115.68(16) . . ?
C5 C10 C9 124.43(18) . . ?
O3 C18 N3 123.01(18) . . ?
O3 C18 C16 121.82(18) . . ?
N3 C18 C16 115.17(17) . . ?
F1 C6 C5 119.03(17) . . ?
F1 C6 C7 117.95(17) . . ?
C7 C6 C5 122.96(17) . . ?
C15A C16A C18A 116.94(17) . . ?
C15A C16A C17A 119.52(18) . . ?
C17A C16A C18A 123.53(18) . . ?
N2 C11 H11 109.3 . . ?
N2 C11 H10 109.3 . . ?
N2 C11 C12 111.80(16) . . ?
H11 C11 H10 107.9 . . ?
C12 C11 H11 109.3 . . ?
C12 C11 H10 109.3 . . ?
N2A C11A H10A 108.4 . . ?
N2A C11A H11A 108.4 . . ?
N2A C11A C12A 115.39(16) . . ?
H10A C11A H11A 107.5 . . ?
C12A C11A H10A 108.4 . . ?
C12A C11A H11A 108.4 . . ?
O2 C17 C8 119.84(17) . . ?
O2 C17 C16 124.83(18) . . ?
C16 C17 C8 115.32(17) . . ?
C8 C7 H9 119.9 . . ?
C6 C7 C8 120.15(18) . . ?
C6 C7 H9 119.9 . . ?
O2A C17A C8A 120.13(18) . . ?
O2A C17A C16A 124.97(18) . . ?
C16A C17A C8A 114.90(17) . . ?
C8A C7A H9A 120.1 . . ?
C6A C7A C8A 119.80(19) . . ?
C6A C7A H9A 120.1 . . ?
N3A C19A H22A 108.8 . . ?
N3A C19A H21A 108.8 . . ?
N3A C19A C20A 113.83(17) . . ?
H22A C19A H21A 107.7 . . ?
C20A C19A H22A 108.8 . . ?
C20A C19A H21A 108.8 . . ?
F1A C6A C5A 119.19(17) . . ?
F1A C6A C7A 117.84(18) . . ?
C7A C6A C5A 122.91(18) . . ?
N1 C1 H1 110.2 . . ?
N1 C1 H2 110.2 . . ?
N1 C1 C2 107.44(17) . . ?
H1 C1 H2 108.5 . . ?
C2 C1 H1 110.2 . . ?
C2 C1 H2 110.2 . . ?
N3 C19 H22 108.9 . . ?
N3 C19 H21 108.9 . . ?
N3 C19 C20 113.15(18) . . ?
H22 C19 H21 107.8 . . ?
C20 C19 H22 108.9 . . ?
C20 C19 H21 108.9 . . ?
C21A C20A C19A 118.64(19) . . ?
C25A C20A C19A 122.18(19) . . ?
C25A C20A C21A 119.2(2) . . ?
N1A C1A H2A 110.3 . . ?
N1A C1A H1A 110.3 . . ?
N1A C1A C2A 107.10(18) . . ?
H2A C1A H1A 108.5 . . ?
C2A C1A H2A 110.3 . . ?
C2A C1A H1A 110.3 . . ?
O1 C2 C1 111.07(16) . . ?
O1 C2 H3 109.4 . . ?
O1 C2 H4 109.4 . . ?
C1 C2 H3 109.4 . . ?
C1 C2 H4 109.4 . . ?
H3 C2 H4 108.0 . . ?
N1 C4 H7 109.8 . . ?
N1 C4 H8 109.8 . . ?
N1 C4 C3 109.49(17) . . ?
H7 C4 H8 108.2 . . ?
C3 C4 H7 109.8 . . ?
C3 C4 H8 109.8 . . ?
C20A C21A H23A 119.8 . . ?
C22A C21A C20A 120.4(2) . . ?
C22A C21A H23A 119.8 . . ?
N1A C4A H8A 109.8 . . ?
N1A C4A H7A 109.8 . . ?
N1A C4A C3A 109.53(18) . . ?
H8A C4A H7A 108.2 . . ?
C3A C4A H8A 109.8 . . ?
C3A C4A H7A 109.8 . . ?
C11A C12A H13A 108.5 . . ?
C11A C12A H12A 108.5 . . ?
H13A C12A H12A 107.5 . . ?
C13A C12A C11A 115.19(18) . . ?
C13A C12A H13A 108.5 . . ?
C13A C12A H12A 108.5 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 C25 118.9(2) . . ?
C25 C20 C19 121.1(2) . . ?
C20A C25A H27A 120.0 . . ?
C20A C25A C24A 120.0(2) . . ?
C24A C25A H27A 120.0 . . ?
C11 C12 H12 108.9 . . ?
C11 C12 H13 108.9 . . ?
H12 C12 H13 107.7 . . ?
C13 C12 C11 113.6(2) . . ?
C13 C12 H12 108.9 . . ?
C13 C12 H13 108.9 . . ?
C12A C13A H15A 109.3 . . ?
C12A C13A H14A 109.3 . . ?
C12A C13A C14A 111.56(19) . . ?
H15A C13A H14A 108.0 . . ?
C14A C13A H15A 109.3 . . ?
C14A C13A H14A 109.3 . . ?
O1A C2A C1A 111.19(17) . . ?
O1A C2A H4A 109.4 . . ?
O1A C2A H3A 109.4 . . ?
C1A C2A H4A 109.4 . . ?
C1A C2A H3A 109.4 . . ?
H4A C2A H3A 108.0 . . ?
O1 C3 C4 111.94(19) . . ?
O1 C3 H6 109.2 . . ?
O1 C3 H5 109.2 . . ?
C4 C3 H6 109.2 . . ?
C4 C3 H5 109.2 . . ?
H6 C3 H5 107.9 . . ?
O1A C3A C4A 112.0(2) . . ?
O1A C3A H6A 109.2 . . ?
O1A C3A H5A 109.2 . . ?
C4A C3A H6A 109.2 . . ?
C4A C3A H5A 109.2 . . ?
H6A C3A H5A 107.9 . . ?
C24A C23A H25A 120.0 . . ?
C22A C23A H25A 120.0 . . ?
C22A C23A C24A 120.0(2) . . ?
C25A C24A H26A 119.8 . . ?
C23A C24A C25A 120.3(2) . . ?
C23A C24A H26A 119.8 . . ?
C21A C22A H24A 120.0 . . ?
C23A C22A C21A 120.1(2) . . ?
C23A C22A H24A 120.0 . . ?
C20 C21 H23 119.5 . . ?
C20 C21 C22 120.9(3) . . ?
C22 C21 H23 119.5 . . ?
C12 C13 H15 109.1 . . ?
C12 C13 H14 109.1 . . ?
C12 C13 C14 112.5(2) . . ?
H15 C13 H14 107.8 . . ?
C14 C13 H15 109.1 . . ?
C14 C13 H14 109.1 . . ?
C13A C14A H16A 109.5 . . ?
C13A C14A H17A 109.5 . . ?
C13A C14A H18A 109.5 . . ?
H16A C14A H17A 109.5 . . ?
H16A C14A H18A 109.5 . . ?
H17A C14A H18A 109.5 . . ?
C20 C25 H27 119.8 . . ?
C20 C25 C24 120.4(3) . . ?
C24 C25 H27 119.8 . . ?
C21 C22 H24 120.1 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H24 120.1 . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H17 109.5 . . ?
C13 C14 H18 109.5 . . ?
H16 C14 H17 109.5 . . ?
H16 C14 H18 109.5 . . ?
H17 C14 H18 109.5 . . ?
C22 C23 H25 120.0 . . ?
C22 C23 C24 120.1(3) . . ?
C24 C23 H25 120.0 . . ?
C25 C24 H26 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H26 120.0 . . ?

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
F1 C6 C7 C8 -175.22(17) . . . . ?
O3A C18A C16A C15A 0.0(3) . . . . ?
O3A C18A C16A C17A 179.39(19) . . . . ?
N2 C15 C16 C18 177.59(17) . . . . ?
N2 C15 C16 C17 -1.0(3) . . . . ?
N2 C9 C10 F2 3.1(3) . . . . ?
N2 C9 C10 C5 -174.41(17) . . . . ?
N2 C11 C12 C13 -162.68(18) . . . . ?
N2A C9A C8A C17A 0.8(3) . . . . ?
N2A C9A C8A C7A 178.89(17) . . . . ?
N2A C9A C10A F2A 6.3(3) . . . . ?
N2A C9A C10A C5A -172.11(18) . . . . ?
N2A C15A C16A C18A 178.94(18) . . . . ?
N2A C15A C16A C17A -0.5(3) . . . . ?
N2A C11A C12A C13A 60.9(2) . . . . ?
N1 C5 C10 F2 -4.7(3) . . . . ?
N1 C5 C10 C9 172.93(17) . . . . ?
N1 C5 C6 F1 0.9(3) . . . . ?
N1 C5 C6 C7 -176.31(18) . . . . ?
N1 C1 C2 O1 -62.5(2) . . . . ?
N1 C4 C3 O1 56.3(2) . . . . ?
N3A C18A C16A C15A -179.55(18) . . . . ?
N3A C18A C16A C17A -0.1(3) . . . . ?
N3A C19A C20A C21A -158.16(18) . . . . ?
N3A C19A C20A C25A 20.6(3) . . . . ?
N1A C5A C10A F2A -7.9(3) . . . . ?
N1A C5A C10A C9A 170.61(18) . . . . ?
N1A C5A C6A F1A 2.1(3) . . . . ?
N1A C5A C6A C7A -175.01(19) . . . . ?
N1A C1A C2A O1A -62.8(2) . . . . ?
N1A C4A C3A O1A 55.6(3) . . . . ?
N3 C19 C20 C21 -145.8(2) . . . . ?
N3 C19 C20 C25 36.3(3) . . . . ?
C8 C9 C10 F2 -177.81(16) . . . . ?
C8 C9 C10 C5 4.7(3) . . . . ?
C15 N2 C9 C8 -2.4(3) . . . . ?
C15 N2 C9 C10 176.66(18) . . . . ?
C15 N2 C11 C12 -98.9(2) . . . . ?
C15 C16 C18 O3 -0.5(3) . . . . ?
C15 C16 C18 N3 -179.87(18) . . . . ?
C15 C16 C17 O2 179.9(2) . . . . ?
C15 C16 C17 C8 -0.7(3) . . . . ?
C9 N2 C15 C16 2.6(3) . . . . ?
C9 N2 C11 C12 77.1(2) . . . . ?
C9 C8 C17 O2 -179.78(19) . . . . ?
C9 C8 C17 C16 0.8(3) . . . . ?
C9 C8 C7 C6 -3.6(3) . . . . ?
C9A N2A C15A C16A 2.0(3) . . . . ?
C9A N2A C11A C12A 77.6(2) . . . . ?
C9A C8A C17A O2A 180.0(2) . . . . ?
C9A C8A C17A C16A 0.6(3) . . . . ?
C9A C8A C7A C6A -4.6(3) . . . . ?
C5 N1 C1 C2 -165.65(16) . . . . ?
C5 N1 C4 C3 166.07(17) . . . . ?
C5 C6 C7 C8 2.0(3) . . . . ?
C5A N1A C1A C2A -165.33(17) . . . . ?
C5A N1A C4A C3A 165.77(18) . . . . ?
C8A C9A C10A F2A -175.36(16) . . . . ?
C8A C9A C10A C5A 6.2(3) . . . . ?
C8A C7A C6A F1A -174.72(17) . . . . ?
C8A C7A C6A C5A 2.4(3) . . . . ?
C18A N3A C19A C20A -107.8(2) . . . . ?
C18A C16A C17A O2A 0.5(3) . . . . ?
C18A C16A C17A C8A 179.80(18) . . . . ?
C15A N2A C9A C8A -2.1(3) . . . . ?
C15A N2A C9A C10A 176.22(18) . . . . ?
C15A N2A C11A C12A -102.7(2) . . . . ?
C15A C16A C17A O2A 179.9(2) . . . . ?
C15A C16A C17A C8A -0.8(3) . . . . ?
C10A C9A C8A C17A -177.64(18) . . . . ?
C10A C9A C8A C7A 0.5(3) . . . . ?
C10A C5A C6A F1A -179.21(17) . . . . ?
C10A C5A C6A C7A 3.7(3) . . . . ?
C10 C5 C6 F1 179.85(16) . . . . ?
C10 C5 C6 C7 2.7(3) . . . . ?
C18 N3 C19 C20 -103.2(2) . . . . ?
C18 C16 C17 O2 1.4(3) . . . . ?
C18 C16 C17 C8 -179.20(17) . . . . ?
C6 C5 C10 F2 176.27(16) . . . . ?
C6 C5 C10 C9 -6.1(3) . . . . ?
C11 N2 C15 C16 178.73(18) . . . . ?
C11 N2 C9 C8 -178.25(17) . . . . ?
C11 N2 C9 C10 0.8(3) . . . . ?
C11 C12 C13 C14 -177.6(2) . . . . ?
C11A N2A C9A C8A 177.61(17) . . . . ?
C11A N2A C9A C10A -4.1(3) . . . . ?
C11A N2A C15A C16A -177.69(18) . . . . ?
C11A C12A C13A C14A 174.76(19) . . . . ?
C17 C8 C9 N2 0.8(3) . . . . ?
C17 C8 C9 C10 -178.39(17) . . . . ?
C17 C8 C7 C6 175.26(18) . . . . ?
C17 C16 C18 O3 178.03(19) . . . . ?
C17 C16 C18 N3 -1.3(3) . . . . ?
C7 C8 C9 N2 179.53(17) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C17 O2 1.4(3) . . . . ?
C7 C8 C17 C16 -178.03(17) . . . . ?
C17A C8A C7A C6A 173.61(19) . . . . ?
C7A C8A C17A O2A 1.8(3) . . . . ?
C7A C8A C17A C16A -177.54(18) . . . . ?
C19A N3A C18A O3A -1.5(3) . . . . ?
C19A N3A C18A C16A 177.98(18) . . . . ?
C19A C20A C21A C22A 179.0(2) . . . . ?
C19A C20A C25A C24A -178.8(2) . . . . ?
C6A C5A C10A F2A 173.31(16) . . . . ?
C6A C5A C10A C9A -8.2(3) . . . . ?
C1 N1 C5 C10 160.42(17) . . . . ?
C1 N1 C5 C6 -20.6(3) . . . . ?
C1 N1 C4 C3 -57.2(2) . . . . ?
C19 N3 C18 O3 -2.5(3) . . . . ?
C19 N3 C18 C16 176.88(18) . . . . ?
C19 C20 C21 C22 -178.1(2) . . . . ?
C19 C20 C25 C24 177.9(3) . . . . ?
C20A C21A C22A C23A 0.1(4) . . . . ?
C20A C25A C24A C23A -0.2(4) . . . . ?
C1A N1A C5A C10A 161.91(17) . . . . ?
C1A N1A C5A C6A -19.4(3) . . . . ?
C1A N1A C4A C3A -57.6(2) . . . . ?
C2 O1 C3 C4 -57.9(2) . . . . ?
C4 N1 C5 C10 -67.2(2) . . . . ?
C4 N1 C5 C6 111.7(2) . . . . ?
C4 N1 C1 C2 59.7(2) . . . . ?
C21A C20A C25A C24A 0.0(3) . . . . ?
C4A N1A C5A C10A -65.9(2) . . . . ?
C4A N1A C5A C6A 112.8(2) . . . . ?
C4A N1A C1A C2A 60.3(2) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C20 C25 C24 C23 0.2(5) . . . . ?
C25A C20A C21A C22A 0.1(3) . . . . ?
C2A O1A C3A C4A -56.9(3) . . . . ?
C3 O1 C2 C1 61.3(2) . . . . ?
C3A O1A C2A C1A 60.9(2) . . . . ?
C24A C23A C22A C21A -0.3(4) . . . . ?
C22A C23A C24A C25A 0.4(4) . . . . ?
C21 C20 C25 C24 0.0(4) . . . . ?
C21 C22 C23 C24 0.0(5) . . . . ?
C25 C20 C21 C22 -0.2(4) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?

_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_P21_c_120K
_database_code_depnum_ccdc_archive 'CCDC 2386801'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-02-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2041(3)
_cell_length_b                   14.5742(3)
_cell_length_c                   24.7844(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.0940(10)
_cell_angle_gamma                90
_cell_volume                     4397.03(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0954 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.9512.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            66982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.412
_diffrn_reflns_theta_min         2.160
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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                   xray
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6612
_reflns_number_total             9020
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     605
_refine_ls_number_reflns         9020
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.072
_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)+(0.0731P)²+5.1068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1785
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00U(H00C,H00D), C00V(H00A,H00B), C014(H01W,H01X), C015(H01A,H01B), C016(H01C,
 H01D), C017(H01E,H01F), C018(H01Y,H), C01A(H01Z,HA), C01B(H01G,H01H), C01C(H01,
 HB), C01E(H2,HC), C01F(H01I,H01J), C01H(H01K,H01L), C01I(H3,HD), C01K(H5,HE),
 C01O(H01M,H01N)
2.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00R(H00R), C00X(H00X), C013(H013), C019(H019), C01D(H1),
 C01J(H4), C01L(H6), C01M(H7), C01P(H01P), C01Q(H01Q), C01R(H01R), C01T(H01U),
 C01U(H01V)
2.c Idealised Me refined as rotating group:
 C01N(H8,HF,HG), C01S(H01O,H01S,H01T)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F1 F 0.39678(10) 0.56257(9) 0.22352(5) 0.0270(3) Uani 1 1 d . . . . .
F2 F 0.41385(10) 0.67490(8) 0.40166(5) 0.0273(3) Uani 1 1 d . . . . .
F2A F 0.92767(9) 0.67510(8) 0.40660(5) 0.0257(3) Uani 1 1 d . . . . .
F1A F 0.90640(10) 0.57080(9) 0.22660(5) 0.0304(3) Uani 1 1 d . . . . .
O3 O -0.05347(12) 0.42130(11) 0.45109(6) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.09048(13) 0.40627(12) 0.30149(6) 0.0340(4) Uani 1 1 d . . . . .
O3A O 0.44832(13) 0.43080(11) 0.45029(6) 0.0312(4) Uani 1 1 d . . . . .
O1 O 0.63213(12) 0.82720(10) 0.26914(6) 0.0308(4) Uani 1 1 d . . . . .
O2A O 0.59834(13) 0.41482(12) 0.30235(6) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.22169(13) 0.57137(11) 0.42374(6) 0.0185(3) Uani 1 1 d . . . . .
O1A O 1.13497(13) 0.83958(12) 0.27495(7) 0.0385(4) Uani 1 1 d . . . . .
N2A N 0.73043(13) 0.57602(11) 0.42687(6) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.49247(13) 0.68674(11) 0.30483(6) 0.0208(3) Uani 1 1 d . . . . .
N3A N 0.44063(14) 0.36806(12) 0.36629(7) 0.0231(4) Uani 1 1 d . . . . .
N3 N -0.06345(14) 0.35794(12) 0.36720(7) 0.0247(4) Uani 1 1 d . . . . .
N1A N 1.00005(13) 0.69466(12) 0.30866(7) 0.0234(4) Uani 1 1 d . . . . .
C5 C 0.40743(15) 0.62404(13) 0.31257(8) 0.0193(4) Uani 1 1 d . . . . .
C8 C 0.22573(15) 0.51192(13) 0.33301(7) 0.0187(4) Uani 1 1 d . . . . .
C9A C 0.78108(15) 0.57365(13) 0.37803(7) 0.0190(4) Uani 1 1 d . . . . .
C15 C 0.12969(15) 0.52214(13) 0.42949(7) 0.0184(4) Uani 1 1 d . . . . .
H19 H 0.096145 0.527400 0.462778 0.022 Uiso 1 1 calc R U . . .
C16 C 0.08085(15) 0.46495(13) 0.39082(8) 0.0193(4) Uani 1 1 d . . . . .
C9 C 0.27084(15) 0.56872(13) 0.37453(7) 0.0181(4) Uani 1 1 d . . . . .
C10A C 0.87449(16) 0.62503(13) 0.36690(8) 0.0199(4) Uani 1 1 d . . . . .
C8A C 0.73542(16) 0.51788(13) 0.33577(8) 0.0211(4) Uani 1 1 d . . . . .
C5A C 0.91679(15) 0.63045(13) 0.31616(8) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.36375(16) 0.62095(13) 0.36293(7) 0.0195(4) Uani 1 1 d . . . . .
C15A C 0.63725(16) 0.52710(13) 0.43147(8) 0.0200(4) Uani 1 1 d . . . . .
H19A H 0.603272 0.531412 0.464685 0.024 Uiso 1 1 calc R U . . .
C6 C 0.35933(16) 0.56368(14) 0.27362(8) 0.0208(4) Uani 1 1 d . . . . .
C18A C 0.48617(16) 0.42220(13) 0.40563(8) 0.0212(4) Uani 1 1 d . . . . .
C11A C 0.77338(16) 0.62931(13) 0.47487(7) 0.0213(4) Uani 1 1 d . . . . .
H11A H 0.853789 0.619786 0.479840 0.026 Uiso 1 1 calc R U . . .
H10A H 0.740716 0.604286 0.507210 0.026 Uiso 1 1 calc R U . . .
C11 C 0.26074(16) 0.63088(14) 0.46953(8) 0.0223(4) Uani 1 1 d . . . . .
H11 H 0.341893 0.627803 0.474320 0.027 Uiso 1 1 calc R U . . .
H10 H 0.230965 0.607979 0.503128 0.027 Uiso 1 1 calc R U . . .
C18 C -0.01767(16) 0.41366(14) 0.40587(8) 0.0216(4) Uani 1 1 d . . . . .
C7A C 0.78275(16) 0.51472(14) 0.28588(8) 0.0237(4) Uani 1 1 d . . . . .
H9A H 0.754691 0.473712 0.258471 0.028 Uiso 1 1 calc R U . . .
C16A C 0.58795(16) 0.47185(13) 0.39210(8) 0.0210(4) Uani 1 1 d . . . . .
C20A C 0.36729(17) 0.21102(14) 0.37803(8) 0.0236(4) Uani 1 1 d . . . . .
C6A C 0.86910(16) 0.57061(14) 0.27678(8) 0.0236(4) Uani 1 1 d . . . . .
C17 C 0.12786(16) 0.45622(14) 0.33950(8) 0.0212(4) Uani 1 1 d . . . . .
C17A C 0.63592(16) 0.46330(14) 0.34094(8) 0.0230(4) Uani 1 1 d . . . . .
C7 C 0.27290(16) 0.50828(14) 0.28317(8) 0.0219(4) Uani 1 1 d . . . . .
H9 H 0.244543 0.467063 0.255949 0.026 Uiso 1 1 calc R U . . .
C19A C 0.34401(16) 0.31302(14) 0.37313(8) 0.0235(4) Uani 1 1 d . . . . .
H22A H 0.290374 0.323412 0.341851 0.028 Uiso 1 1 calc R U . . .
H21A H 0.309767 0.333841 0.406028 0.028 Uiso 1 1 calc R U . . .
C19 C -0.15654(17) 0.29950(15) 0.37602(9) 0.0273(5) Uani 1 1 d . . . . .
H22 H -0.210408 0.304000 0.344312 0.033 Uiso 1 1 calc R U . . .
H21 H -0.192669 0.322021 0.407992 0.033 Uiso 1 1 calc R U . . .
C1 C 0.56289(16) 0.67194(14) 0.25987(8) 0.0241(4) Uani 1 1 d . . . . .
H1 H 0.522655 0.687934 0.225039 0.029 Uiso 1 1 calc R U . . .
H2 H 0.585426 0.606774 0.258483 0.029 Uiso 1 1 calc R U . . .
C2 C 0.66265(16) 0.73277(15) 0.26967(9) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.700876 0.717403 0.305095 0.031 Uiso 1 1 calc R U . . .
H4 H 0.714145 0.721463 0.241288 0.031 Uiso 1 1 calc R U . . .
C1A C 1.06799(16) 0.68406(16) 0.26247(8) 0.0276(5) Uani 1 1 d . . . . .
H2A H 1.025770 0.701916 0.228495 0.033 Uiso 1 1 calc R U . . .
H1A H 1.091593 0.619428 0.259234 0.033 Uiso 1 1 calc R U . . .
C21A C 0.28165(19) 0.14973(15) 0.36618(9) 0.0299(5) Uani 1 1 d . . . . .
H23A H 0.210158 0.172284 0.355899 0.036 Uiso 1 1 calc R U . . .
C4A C 0.96478(17) 0.79145(14) 0.31260(9) 0.0284(5) Uani 1 1 d . . . . .
H7A H 0.920998 0.799305 0.344401 0.034 Uiso 1 1 calc R U . . .
H8A H 0.918145 0.808544 0.279813 0.034 Uiso 1 1 calc R U . . .
C4 C 0.45978(17) 0.78436(14) 0.30633(9) 0.0274(4) Uani 1 1 d . . . . .
H7 H 0.414862 0.795209 0.337437 0.033 Uiso 1 1 calc R U . . .
H8 H 0.414948 0.800313 0.272778 0.033 Uiso 1 1 calc R U . . .
C12A C 0.75106(18) 0.73181(15) 0.47218(9) 0.0287(5) Uani 1 1 d . . . . .
H13A H 0.786016 0.760715 0.505218 0.034 Uiso 1 1 calc R U . . .
H12A H 0.786781 0.757372 0.440852 0.034 Uiso 1 1 calc R U . . .
C25A C 0.47109(18) 0.17725(16) 0.39274(9) 0.0315(5) Uani 1 1 d . . . . .
H27A H 0.530302 0.218459 0.400853 0.038 Uiso 1 1 calc R U . . .
C13A C 0.63142(18) 0.75838(15) 0.46715(9) 0.0309(5) Uani 1 1 d . . . . .
H14A H 0.593358 0.729069 0.496625 0.037 Uiso 1 1 calc R U . . .
H15A H 0.597251 0.735547 0.432283 0.037 Uiso 1 1 calc R U . . .
C12 C 0.22552(19) 0.73033(15) 0.46032(9) 0.0306(5) Uani 1 1 d . . . . .
H12 H 0.234341 0.746704 0.422104 0.037 Uiso 1 1 calc R U . . .
H13 H 0.146631 0.736076 0.466641 0.037 Uiso 1 1 calc R U . . .
C20 C -0.12520(19) 0.19962(16) 0.38486(9) 0.0315(5) Uani 1 1 d . . . . .
C3 C 0.56160(19) 0.84385(15) 0.31157(10) 0.0337(5) Uani 1 1 d . . . . .
H6 H 0.539517 0.909230 0.310892 0.040 Uiso 1 1 calc R U . . .
H5 H 0.602271 0.831588 0.346830 0.040 Uiso 1 1 calc R U . . .
C3A C 1.06507(19) 0.85287(17) 0.31809(11) 0.0377(6) Uani 1 1 d . . . . .
H6A H 1.041203 0.917773 0.318494 0.045 Uiso 1 1 calc R U . . .
H5A H 1.106933 0.839909 0.352954 0.045 Uiso 1 1 calc R U . . .
C22A C 0.3000(2) 0.05557(16) 0.36927(10) 0.0371(5) Uani 1 1 d . . . . .
H24A H 0.241096 0.014033 0.361107 0.045 Uiso 1 1 calc R U . . .
C2A C 1.16681(17) 0.74581(16) 0.27269(9) 0.0312(5) Uani 1 1 d . . . . .
H4A H 1.206949 0.728378 0.307299 0.037 Uiso 1 1 calc R U . . .
H3A H 1.217030 0.737443 0.243428 0.037 Uiso 1 1 calc R U . . .
C24A C 0.4889(2) 0.08308(17) 0.39568(10) 0.0383(6) Uani 1 1 d . . . . .
H26A H 0.560366 0.060178 0.405679 0.046 Uiso 1 1 calc R U . . .
C23A C 0.4033(2) 0.02274(17) 0.38415(10) 0.0393(6) Uani 1 1 d . . . . .
H25A H 0.415767 -0.041520 0.386506 0.047 Uiso 1 1 calc R U . . .
C14A C 0.6168(2) 0.86235(16) 0.47004(10) 0.0389(6) Uani 1 1 d . . . . .
H16A H 0.654670 0.891535 0.440985 0.058 Uiso 1 1 calc R U . . .
H17A H 0.648013 0.884797 0.505116 0.058 Uiso 1 1 calc R U . . .
H18A H 0.538408 0.877408 0.465873 0.058 Uiso 1 1 calc R U . . .
C13 C 0.2895(2) 0.79680(17) 0.49613(10) 0.0393(6) Uani 1 1 d . . . . .
H14 H 0.368025 0.793388 0.488650 0.047 Uiso 1 1 calc R U . . .
H15 H 0.283383 0.779132 0.534369 0.047 Uiso 1 1 calc R U . . .
C21 C -0.1968(2) 0.13090(17) 0.36594(10) 0.0426(6) Uani 1 1 d . . . . .
H23 H -0.264171 0.146741 0.346633 0.051 Uiso 1 1 calc R U . . .
C25 C -0.0271(2) 0.17526(19) 0.41304(13) 0.0490(7) Uani 1 1 d . . . . .
H27 H 0.022697 0.221674 0.426069 0.059 Uiso 1 1 calc R U . . .
C22 C -0.1706(3) 0.0390(2) 0.37503(12) 0.0577(9) Uani 1 1 d . . . . .
H24 H -0.219977 -0.007635 0.361901 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2494(3) 0.89534(18) 0.48786(12) 0.0586(8) Uani 1 1 d . . . . .
H16 H 0.256695 0.913625 0.450237 0.088 Uiso 1 1 calc R U . . .
H17 H 0.293549 0.936286 0.512065 0.088 Uiso 1 1 calc R U . . .
H18 H 0.172092 0.899383 0.495971 0.088 Uiso 1 1 calc R U . . .
C23 C -0.0729(3) 0.0155(2) 0.40311(15) 0.0666(10) Uani 1 1 d . . . . .
H25 H -0.054951 -0.047273 0.409263 0.080 Uiso 1 1 calc R U . . .
C24 C -0.0011(3) 0.0835(2) 0.42232(17) 0.0661(10) Uani 1 1 d . . . . .
H26 H 0.066007 0.067389 0.441843 0.079 Uiso 1 1 calc R U . . .
H20 H -0.033(2) 0.360(2) 0.3345(12) 0.048(8) Uiso 1 1 d . . . . .
H20A H 0.473(2) 0.3689(18) 0.3339(11) 0.036(7) Uiso 1 1 d . . . . .


_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
F1 C6 1.353(2) . ?
F2 C10 1.353(2) . ?
F2A C10A 1.353(2) . ?
F1A C6A 1.354(2) . ?
O3 C18 1.237(2) . ?
O2 C17 1.251(2) . ?
O3A C18A 1.236(2) . ?
O1 C2 1.426(3) . ?
O1 C3 1.426(3) . ?
O2A C17A 1.250(2) . ?
N2 C15 1.349(2) . ?
N2 C9 1.397(2) . ?
N2 C11 1.480(2) . ?
O1A C3A 1.428(3) . ?
O1A C2A 1.423(3) . ?
N2A C9A 1.398(2) . ?
N2A C15A 1.354(2) . ?
N2A C11A 1.485(2) . ?
N1 C5 1.406(2) . ?
N1 C1 1.471(2) . ?
N1 C4 1.479(3) . ?
N3A C18A 1.343(3) . ?
N3A C19A 1.446(3) . ?
N3A H20A 0.92(3) . ?
N3 C18 1.347(3) . ?
N3 C19 1.449(3) . ?
N3 H20 0.91(3) . ?
N1A C5A 1.403(3) . ?
N1A C1A 1.469(2) . ?
N1A C4A 1.480(3) . ?
C5 C10 1.392(3) . ?
C5 C6 1.403(3) . ?
C8 C9 1.402(3) . ?
C8 C17 1.462(3) . ?
C8 C7 1.401(3) . ?
C9A C10A 1.408(3) . ?
C9A C8A 1.409(3) . ?
C15 H19 0.9500 . ?
C15 C16 1.374(3) . ?
C16 C18 1.486(3) . ?
C16 C17 1.438(3) . ?
C9 C10 1.412(3) . ?
C10A C5A 1.395(3) . ?
C8A C7A 1.402(3) . ?
C8A C17A 1.465(3) . ?
C5A C6A 1.404(3) . ?
C15A H19A 0.9500 . ?
C15A C16A 1.370(3) . ?
C6 C7 1.362(3) . ?
C18A C16A 1.496(3) . ?
C11A H11A 0.9900 . ?
C11A H10A 0.9900 . ?
C11A C12A 1.519(3) . ?
C11 H11 0.9900 . ?
C11 H10 0.9900 . ?
C11 C12 1.524(3) . ?
C7A H9A 0.9500 . ?
C7A C6A 1.364(3) . ?
C16A C17A 1.439(3) . ?
C20A C19A 1.517(3) . ?
C20A C21A 1.390(3) . ?
C20A C25A 1.383(3) . ?
C7 H9 0.9500 . ?
C19A H22A 0.9900 . ?
C19A H21A 0.9900 . ?
C19 H22 0.9900 . ?
C19 H21 0.9900 . ?
C19 C20 1.517(3) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C1 C2 1.512(3) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
C1A H2A 0.9900 . ?
C1A H1A 0.9900 . ?
C1A C2A 1.512(3) . ?
C21A H23A 0.9500 . ?
C21A C22A 1.392(3) . ?
C4A H7A 0.9900 . ?
C4A H8A 0.9900 . ?
C4A C3A 1.515(3) . ?
C4 H7 0.9900 . ?
C4 H8 0.9900 . ?
C4 C3 1.513(3) . ?
C12A H13A 0.9900 . ?
C12A H12A 0.9900 . ?
C12A C13A 1.507(3) . ?
C25A H27A 0.9500 . ?
C25A C24A 1.391(3) . ?
C13A H14A 0.9900 . ?
C13A H15A 0.9900 . ?
C13A C14A 1.528(3) . ?
C12 H12 0.9900 . ?
C12 H13 0.9900 . ?
C12 C13 1.496(3) . ?
C20 C21 1.388(3) . ?
C20 C25 1.389(4) . ?
C3 H6 0.9900 . ?
C3 H5 0.9900 . ?
C3A H6A 0.9900 . ?
C3A H5A 0.9900 . ?
C22A H24A 0.9500 . ?
C22A C23A 1.374(4) . ?
C2A H4A 0.9900 . ?
C2A H3A 0.9900 . ?
C24A H26A 0.9500 . ?
C24A C23A 1.380(4) . ?
C23A H25A 0.9500 . ?
C14A H16A 0.9800 . ?
C14A H17A 0.9800 . ?
C14A H18A 0.9800 . ?
C13 H14 0.9900 . ?
C13 H15 0.9900 . ?
C13 C14 1.527(4) . ?
C21 H23 0.9500 . ?
C21 C22 1.392(4) . ?
C25 H27 0.9500 . ?
C25 C24 1.390(4) . ?
C22 H24 0.9500 . ?
C22 C23 1.380(5) . ?
C14 H16 0.9800 . ?
C14 H17 0.9800 . ?
C14 H18 0.9800 . ?
C23 H25 0.9500 . ?
C23 C24 1.385(5) . ?
C24 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.18(15) . . ?
C15 N2 C9 119.34(16) . . ?
C15 N2 C11 117.11(15) . . ?
C9 N2 C11 123.41(16) . . ?
C2A O1A C3A 109.82(16) . . ?
C9A N2A C11A 123.64(16) . . ?
C15A N2A C9A 119.06(16) . . ?
C15A N2A C11A 117.30(15) . . ?
C5 N1 C1 119.01(16) . . ?
C5 N1 C4 114.75(15) . . ?
C1 N1 C4 109.48(15) . . ?
C18A N3A C19A 122.63(17) . . ?
C18A N3A H20A 116.3(17) . . ?
C19A N3A H20A 121.0(16) . . ?
C18 N3 C19 122.48(17) . . ?
C18 N3 H20 116.1(19) . . ?
C19 N3 H20 121.4(19) . . ?
C5A N1A C1A 119.16(17) . . ?
C5A N1A C4A 114.21(16) . . ?
C1A N1A C4A 109.54(16) . . ?
C10 C5 N1 118.48(17) . . ?
C10 C5 C6 115.36(17) . . ?
C6 C5 N1 126.15(17) . . ?
C9 C8 C17 121.87(17) . . ?
C7 C8 C9 120.33(17) . . ?
C7 C8 C17 117.80(17) . . ?
N2A C9A C10A 124.80(17) . . ?
N2A C9A C8A 118.81(17) . . ?
C10A C9A C8A 116.37(17) . . ?
N2 C15 H19 117.6 . . ?
N2 C15 C16 124.90(17) . . ?
C16 C15 H19 117.6 . . ?
C15 C16 C18 116.65(17) . . ?
C15 C16 C17 119.36(17) . . ?
C17 C16 C18 123.97(17) . . ?
N2 C9 C8 119.09(17) . . ?
N2 C9 C10 124.31(17) . . ?
C8 C9 C10 116.59(17) . . ?
F2A C10A C9A 119.84(16) . . ?
F2A C10A C5A 115.83(17) . . ?
C5A C10A C9A 124.31(18) . . ?
C9A C8A C17A 122.31(17) . . ?
C7A C8A C9A 120.57(18) . . ?
C7A C8A C17A 117.09(18) . . ?
N1A C5A C6A 126.18(17) . . ?
C10A C5A N1A 118.36(18) . . ?
C10A C5A C6A 115.45(17) . . ?
F2 C10 C5 115.76(16) . . ?
F2 C10 C9 119.85(16) . . ?
C5 C10 C9 124.35(17) . . ?
N2A C15A H19A 117.3 . . ?
N2A C15A C16A 125.32(17) . . ?
C16A C15A H19A 117.3 . . ?
F1 C6 C5 119.11(17) . . ?
F1 C6 C7 117.95(17) . . ?
C7 C6 C5 122.88(17) . . ?
O3A C18A N3A 123.22(18) . . ?
O3A C18A C16A 121.40(18) . . ?
N3A C18A C16A 115.38(17) . . ?
N2A C11A H11A 108.5 . . ?
N2A C11A H10A 108.5 . . ?
N2A C11A C12A 115.30(16) . . ?
H11A C11A H10A 107.5 . . ?
C12A C11A H11A 108.5 . . ?
C12A C11A H10A 108.5 . . ?
N2 C11 H11 109.3 . . ?
N2 C11 H10 109.3 . . ?
N2 C11 C12 111.74(16) . . ?
H11 C11 H10 107.9 . . ?
C12 C11 H11 109.3 . . ?
C12 C11 H10 109.3 . . ?
O3 C18 N3 122.94(18) . . ?
O3 C18 C16 121.80(18) . . ?
N3 C18 C16 115.25(17) . . ?
C8A C7A H9A 120.1 . . ?
C6A C7A C8A 119.87(19) . . ?
C6A C7A H9A 120.1 . . ?
C15A C16A C18A 117.00(17) . . ?
C15A C16A C17A 119.50(18) . . ?
C17A C16A C18A 123.49(17) . . ?
C21A C20A C19A 118.63(19) . . ?
C25A C20A C19A 122.18(19) . . ?
C25A C20A C21A 119.2(2) . . ?
F1A C6A C5A 119.16(17) . . ?
F1A C6A C7A 117.87(18) . . ?
C7A C6A C5A 122.90(18) . . ?
O2 C17 C8 119.81(17) . . ?
O2 C17 C16 124.80(18) . . ?
C16 C17 C8 115.39(17) . . ?
O2A C17A C8A 120.08(18) . . ?
O2A C17A C16A 124.96(18) . . ?
C16A C17A C8A 114.95(17) . . ?
C8 C7 H9 119.9 . . ?
C6 C7 C8 120.19(18) . . ?
C6 C7 H9 119.9 . . ?
N3A C19A C20A 113.79(17) . . ?
N3A C19A H22A 108.8 . . ?
N3A C19A H21A 108.8 . . ?
C20A C19A H22A 108.8 . . ?
C20A C19A H21A 108.8 . . ?
H22A C19A H21A 107.7 . . ?
N3 C19 H22 108.9 . . ?
N3 C19 H21 108.9 . . ?
N3 C19 C20 113.17(18) . . ?
H22 C19 H21 107.8 . . ?
C20 C19 H22 108.9 . . ?
C20 C19 H21 108.9 . . ?
N1 C1 H1 110.2 . . ?
N1 C1 H2 110.2 . . ?
N1 C1 C2 107.44(16) . . ?
H1 C1 H2 108.5 . . ?
C2 C1 H1 110.2 . . ?
C2 C1 H2 110.2 . . ?
O1 C2 C1 110.96(16) . . ?
O1 C2 H3 109.4 . . ?
O1 C2 H4 109.4 . . ?
C1 C2 H3 109.4 . . ?
C1 C2 H4 109.4 . . ?
H3 C2 H4 108.0 . . ?
N1A C1A H2A 110.3 . . ?
N1A C1A H1A 110.3 . . ?
N1A C1A C2A 107.14(18) . . ?
H2A C1A H1A 108.5 . . ?
C2A C1A H2A 110.3 . . ?
C2A C1A H1A 110.3 . . ?
C20A C21A H23A 119.8 . . ?
C20A C21A C22A 120.4(2) . . ?
C22A C21A H23A 119.8 . . ?
N1A C4A H7A 109.8 . . ?
N1A C4A H8A 109.8 . . ?
N1A C4A C3A 109.40(17) . . ?
H7A C4A H8A 108.2 . . ?
C3A C4A H7A 109.8 . . ?
C3A C4A H8A 109.8 . . ?
N1 C4 H7 109.8 . . ?
N1 C4 H8 109.8 . . ?
N1 C4 C3 109.39(17) . . ?
H7 C4 H8 108.2 . . ?
C3 C4 H7 109.8 . . ?
C3 C4 H8 109.8 . . ?
C11A C12A H13A 108.5 . . ?
C11A C12A H12A 108.5 . . ?
H13A C12A H12A 107.5 . . ?
C13A C12A C11A 115.21(18) . . ?
C13A C12A H13A 108.5 . . ?
C13A C12A H12A 108.5 . . ?
C20A C25A H27A 119.9 . . ?
C20A C25A C24A 120.1(2) . . ?
C24A C25A H27A 119.9 . . ?
C12A C13A H14A 109.3 . . ?
C12A C13A H15A 109.3 . . ?
C12A C13A C14A 111.50(19) . . ?
H14A C13A H15A 108.0 . . ?
C14A C13A H14A 109.3 . . ?
C14A C13A H15A 109.3 . . ?
C11 C12 H12 108.9 . . ?
C11 C12 H13 108.9 . . ?
H12 C12 H13 107.7 . . ?
C13 C12 C11 113.4(2) . . ?
C13 C12 H12 108.9 . . ?
C13 C12 H13 108.9 . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 C25 119.0(2) . . ?
C25 C20 C19 121.2(2) . . ?
O1 C3 C4 111.98(19) . . ?
O1 C3 H6 109.2 . . ?
O1 C3 H5 109.2 . . ?
C4 C3 H6 109.2 . . ?
C4 C3 H5 109.2 . . ?
H6 C3 H5 107.9 . . ?
O1A C3A C4A 112.0(2) . . ?
O1A C3A H6A 109.2 . . ?
O1A C3A H5A 109.2 . . ?
C4A C3A H6A 109.2 . . ?
C4A C3A H5A 109.2 . . ?
H6A C3A H5A 107.9 . . ?
C21A C22A H24A 120.0 . . ?
C23A C22A C21A 119.9(2) . . ?
C23A C22A H24A 120.0 . . ?
O1A C2A C1A 111.19(17) . . ?
O1A C2A H4A 109.4 . . ?
O1A C2A H3A 109.4 . . ?
C1A C2A H4A 109.4 . . ?
C1A C2A H3A 109.4 . . ?
H4A C2A H3A 108.0 . . ?
C25A C24A H26A 119.8 . . ?
C23A C24A C25A 120.3(2) . . ?
C23A C24A H26A 119.8 . . ?
C22A C23A C24A 120.0(2) . . ?
C22A C23A H25A 120.0 . . ?
C24A C23A H25A 120.0 . . ?
C13A C14A H16A 109.5 . . ?
C13A C14A H17A 109.5 . . ?
C13A C14A H18A 109.5 . . ?
H16A C14A H17A 109.5 . . ?
H16A C14A H18A 109.5 . . ?
H17A C14A H18A 109.5 . . ?
C12 C13 H14 109.1 . . ?
C12 C13 H15 109.1 . . ?
C12 C13 C14 112.4(2) . . ?
H14 C13 H15 107.9 . . ?
C14 C13 H14 109.1 . . ?
C14 C13 H15 109.1 . . ?
C20 C21 H23 119.7 . . ?
C20 C21 C22 120.5(3) . . ?
C22 C21 H23 119.7 . . ?
C20 C25 H27 119.7 . . ?
C20 C25 C24 120.5(3) . . ?
C24 C25 H27 119.7 . . ?
C21 C22 H24 120.0 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H24 120.0 . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H17 109.5 . . ?
C13 C14 H18 109.5 . . ?
H16 C14 H17 109.5 . . ?
H16 C14 H18 109.5 . . ?
H17 C14 H18 109.5 . . ?
C22 C23 H25 120.0 . . ?
C22 C23 C24 119.9(3) . . ?
C24 C23 H25 120.0 . . ?
C25 C24 H26 120.0 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H26 120.0 . . ?

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
F1 C6 C7 C8 -175.18(17) . . . . ?
F2A C10A C5A N1A -7.9(3) . . . . ?
F2A C10A C5A C6A 173.15(16) . . . . ?
O3A C18A C16A C15A 0.1(3) . . . . ?
O3A C18A C16A C17A 179.27(19) . . . . ?
N2 C15 C16 C18 177.51(17) . . . . ?
N2 C15 C16 C17 -1.1(3) . . . . ?
N2 C9 C10 F2 3.1(3) . . . . ?
N2 C9 C10 C5 -174.56(17) . . . . ?
N2 C11 C12 C13 -162.60(18) . . . . ?
N2A C9A C10A F2A 6.2(3) . . . . ?
N2A C9A C10A C5A -172.17(18) . . . . ?
N2A C9A C8A C7A 178.99(17) . . . . ?
N2A C9A C8A C17A 0.9(3) . . . . ?
N2A C15A C16A C18A 178.94(17) . . . . ?
N2A C15A C16A C17A -0.3(3) . . . . ?
N2A C11A C12A C13A 60.9(2) . . . . ?
N1 C5 C10 F2 -4.8(3) . . . . ?
N1 C5 C10 C9 172.90(17) . . . . ?
N1 C5 C6 F1 0.9(3) . . . . ?
N1 C5 C6 C7 -176.25(18) . . . . ?
N1 C1 C2 O1 -62.7(2) . . . . ?
N1 C4 C3 O1 56.3(2) . . . . ?
N3A C18A C16A C15A -179.42(18) . . . . ?
N3A C18A C16A C17A -0.2(3) . . . . ?
N3 C19 C20 C21 -145.7(2) . . . . ?
N3 C19 C20 C25 36.2(3) . . . . ?
N1A C5A C6A F1A 1.9(3) . . . . ?
N1A C5A C6A C7A -174.96(19) . . . . ?
N1A C1A C2A O1A -62.7(2) . . . . ?
N1A C4A C3A O1A 55.5(2) . . . . ?
C5 N1 C1 C2 -165.47(16) . . . . ?
C5 N1 C4 C3 166.01(17) . . . . ?
C5 C6 C7 C8 2.0(3) . . . . ?
C8 C9 C10 F2 -177.76(16) . . . . ?
C8 C9 C10 C5 4.6(3) . . . . ?
C9A N2A C15A C16A 1.9(3) . . . . ?
C9A N2A C11A C12A 77.6(2) . . . . ?
C9A C10A C5A N1A 170.58(17) . . . . ?
C9A C10A C5A C6A -8.4(3) . . . . ?
C9A C8A C7A C6A -4.5(3) . . . . ?
C9A C8A C17A O2A 179.98(19) . . . . ?
C9A C8A C17A C16A 0.7(3) . . . . ?
C15 N2 C9 C8 -2.6(3) . . . . ?
C15 N2 C9 C10 176.57(17) . . . . ?
C15 N2 C11 C12 -98.7(2) . . . . ?
C15 C16 C18 O3 -0.6(3) . . . . ?
C15 C16 C18 N3 -179.77(18) . . . . ?
C15 C16 C17 O2 179.9(2) . . . . ?
C15 C16 C17 C8 -0.8(3) . . . . ?
C9 N2 C15 C16 2.8(3) . . . . ?
C9 N2 C11 C12 77.0(2) . . . . ?
C9 C8 C17 O2 -179.79(19) . . . . ?
C9 C8 C17 C16 0.9(3) . . . . ?
C9 C8 C7 C6 -3.6(3) . . . . ?
C10A C9A C8A C7A 0.4(3) . . . . ?
C10A C9A C8A C17A -177.74(17) . . . . ?
C10A C5A C6A F1A -179.22(16) . . . . ?
C10A C5A C6A C7A 3.9(3) . . . . ?
C8A C9A C10A F2A -175.29(16) . . . . ?
C8A C9A C10A C5A 6.3(3) . . . . ?
C8A C7A C6A F1A -174.65(17) . . . . ?
C8A C7A C6A C5A 2.2(3) . . . . ?
C5A N1A C1A C2A -165.45(17) . . . . ?
C5A N1A C4A C3A 165.80(18) . . . . ?
C10 C5 C6 F1 179.79(16) . . . . ?
C10 C5 C6 C7 2.6(3) . . . . ?
C15A N2A C9A C10A 176.36(18) . . . . ?
C15A N2A C9A C8A -2.1(3) . . . . ?
C15A N2A C11A C12A -102.7(2) . . . . ?
C15A C16A C17A O2A 179.8(2) . . . . ?
C15A C16A C17A C8A -1.0(3) . . . . ?
C6 C5 C10 F2 176.23(16) . . . . ?
C6 C5 C10 C9 -6.1(3) . . . . ?
C18A N3A C19A C20A -107.7(2) . . . . ?
C18A C16A C17A O2A 0.6(3) . . . . ?
C18A C16A C17A C8A 179.85(17) . . . . ?
C11A N2A C9A C10A -4.0(3) . . . . ?
C11A N2A C9A C8A 177.57(17) . . . . ?
C11A N2A C15A C16A -177.80(18) . . . . ?
C11A C12A C13A C14A 174.69(18) . . . . ?
C11 N2 C15 C16 178.69(18) . . . . ?
C11 N2 C9 C8 -178.18(17) . . . . ?
C11 N2 C9 C10 1.0(3) . . . . ?
C11 C12 C13 C14 -177.5(2) . . . . ?
C18 N3 C19 C20 -103.2(2) . . . . ?
C18 C16 C17 O2 1.5(3) . . . . ?
C18 C16 C17 C8 -179.24(17) . . . . ?
C7A C8A C17A O2A 1.8(3) . . . . ?
C7A C8A C17A C16A -177.52(17) . . . . ?
C20A C21A C22A C23A 0.0(3) . . . . ?
C20A C25A C24A C23A -0.2(4) . . . . ?
C17 C8 C9 N2 0.8(3) . . . . ?
C17 C8 C9 C10 -178.43(17) . . . . ?
C17 C8 C7 C6 175.30(18) . . . . ?
C17 C16 C18 O3 177.86(19) . . . . ?
C17 C16 C18 N3 -1.3(3) . . . . ?
C17A C8A C7A C6A 173.75(18) . . . . ?
C7 C8 C9 N2 179.64(17) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C17 O2 1.3(3) . . . . ?
C7 C8 C17 C16 -178.02(17) . . . . ?
C19A N3A C18A O3A -1.4(3) . . . . ?
C19A N3A C18A C16A 178.05(17) . . . . ?
C19A C20A C21A C22A 178.9(2) . . . . ?
C19A C20A C25A C24A -178.8(2) . . . . ?
C19 N3 C18 O3 -2.3(3) . . . . ?
C19 N3 C18 C16 176.82(18) . . . . ?
C19 C20 C21 C22 -178.2(2) . . . . ?
C19 C20 C25 C24 177.9(3) . . . . ?
C1 N1 C5 C10 160.54(17) . . . . ?
C1 N1 C5 C6 -20.6(3) . . . . ?
C1 N1 C4 C3 -57.1(2) . . . . ?
C2 O1 C3 C4 -58.1(2) . . . . ?
C1A N1A C5A C10A 161.99(17) . . . . ?
C1A N1A C5A C6A -19.1(3) . . . . ?
C1A N1A C4A C3A -57.6(2) . . . . ?
C21A C20A C19A N3A -158.13(18) . . . . ?
C21A C20A C25A C24A -0.1(3) . . . . ?
C21A C22A C23A C24A -0.4(4) . . . . ?
C4A N1A C5A C10A -65.9(2) . . . . ?
C4A N1A C5A C6A 113.0(2) . . . . ?
C4A N1A C1A C2A 60.4(2) . . . . ?
C4 N1 C5 C10 -67.0(2) . . . . ?
C4 N1 C5 C6 111.9(2) . . . . ?
C4 N1 C1 C2 59.8(2) . . . . ?
C25A C20A C19A N3A 20.5(3) . . . . ?
C25A C20A C21A C22A 0.2(3) . . . . ?
C25A C24A C23A C22A 0.5(4) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C20 C25 C24 C23 0.4(5) . . . . ?
C3 O1 C2 C1 61.5(2) . . . . ?
C3A O1A C2A C1A 60.8(2) . . . . ?
C2A O1A C3A C4A -56.9(2) . . . . ?
C21 C20 C25 C24 -0.2(4) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C25 C20 C21 C22 0.0(4) . . . . ?
C22 C23 C24 C25 -0.4(5) . . . . ?

_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_P-1_130K
_database_code_depnum_ccdc_archive 'CCDC 2386816'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   10.6773(2)
_cell_length_b                   13.7320(4)
_cell_length_c                   15.4286(4)
_cell_angle_alpha                84.1380(10)
_cell_angle_beta                 88.2670(10)
_cell_angle_gamma                77.3240(10)
_cell_volume                     2195.40(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0948 before and 0.0753 after correction.
The Ratio of minimum to maximum transmission is 0.9214.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            49662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_min         1.923
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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                   xray
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6410
_reflns_number_total             9028
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.099
_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)+(0.1113P)²+2.5762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2395
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C012(H01Y,H), C013(H01A,H01B), C014(H01Z,HA), C015(H01C,H01D), C016(H01E,
 H01F), C018(H01G,H01H), C019(H01,HB), C01A(H0AA,HC), C01B(H1AA,HD), C01C(H01I,
 H01J), C01E(H01K,H01L), C01F(H3AA,HE), C01G(H01M,H01N), C01J(H01O,H01P),
 C01K(H6AA,HF), C01M(H7AA,HG)
2.b Aromatic/amide H refined with riding coordinates:
 N00F(H00F), N00G(H00G), C00O(H00O), C00Q(H00Q), C00S(H00S), C011(H011),
 C01D(H2AA), C01H(H4AA), C01I(H5AA), C01L(H01Q), C01N(H8AA), C01O(H01R),
 C01P(H9AA), C01Q(H01S), C01R(H01T), C01T(H01U)
2.c Idealised Me refined as rotating group:
 C01S(H0BA,HH,HI), C01U(H01V,H01W,H01X)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F2A F 0.64649(15) 0.21489(11) 0.29528(10) 0.0366(4) Uani 1 1 d . . . . .
F1A F 0.51301(15) 0.55269(11) 0.34652(10) 0.0365(4) Uani 1 1 d . . . . .
F2 F -0.13218(15) 0.80234(12) 0.71810(11) 0.0390(4) Uani 1 1 d . . . . .
F1 F -0.02964(16) 0.47059(12) 0.64523(11) 0.0398(4) Uani 1 1 d . . . . .
O2 O 0.22678(19) 0.64166(14) 0.43548(12) 0.0353(4) Uani 1 1 d . . . . .
O2A O 0.26316(19) 0.38172(14) 0.56192(12) 0.0354(4) Uani 1 1 d . . . . .
O3 O 0.31496(19) 0.92873(14) 0.41220(13) 0.0383(5) Uani 1 1 d . . . . .
O3A O 0.1881(2) 0.09046(15) 0.59189(14) 0.0413(5) Uani 1 1 d . . . . .
O1A O 0.82437(19) 0.44658(16) 0.10764(13) 0.0415(5) Uani 1 1 d . . . . .
O1 O -0.3037(2) 0.55371(18) 0.90079(14) 0.0490(6) Uani 1 1 d . . . . .
N2A N 0.4575(2) 0.16131(16) 0.41517(13) 0.0276(4) Uani 1 1 d . . . . .
N1A N 0.6434(2) 0.41778(16) 0.24066(13) 0.0293(5) Uani 1 1 d . . . . .
N2 N 0.0449(2) 0.85861(16) 0.58942(13) 0.0276(4) Uani 1 1 d . . . . .
N1 N -0.1424(2) 0.60022(17) 0.76085(14) 0.0311(5) Uani 1 1 d . . . . .
N3A N 0.1324(2) 0.24861(17) 0.63309(14) 0.0325(5) Uani 1 1 d . . . . .
H20A H 0.147044 0.309531 0.625259 0.039 Uiso 1 1 calc R . . . .
N3 N 0.3664(2) 0.77058(16) 0.36972(14) 0.0310(5) Uani 1 1 d . . . . .
H20 H 0.349982 0.710204 0.377198 0.037 Uiso 1 1 calc R . . . .
C8A C 0.4138(2) 0.33341(19) 0.45119(15) 0.0266(5) Uani 1 1 d . . . . .
C9 C 0.0187(2) 0.76237(19) 0.60198(15) 0.0263(5) Uani 1 1 d . . . . .
C8 C 0.0793(2) 0.68922(19) 0.54838(15) 0.0277(5) Uani 1 1 d . . . . .
C9A C 0.4811(2) 0.25812(18) 0.40150(16) 0.0264(5) Uani 1 1 d . . . . .
C5A C 0.5773(2) 0.38469(19) 0.31430(16) 0.0267(5) Uani 1 1 d . . . . .
C17A C 0.3193(2) 0.31334(19) 0.51737(15) 0.0275(5) Uani 1 1 d . . . . .
C16A C 0.2978(2) 0.21306(19) 0.52554(15) 0.0272(5) Uani 1 1 d . . . . .
C15A C 0.3665(2) 0.14409(19) 0.47431(16) 0.0286(5) Uani 1 1 d . . . . .
H19A H 0.348882 0.078832 0.480727 0.034 Uiso 1 1 calc R . . . .
C16 C 0.2001(2) 0.80785(19) 0.47646(16) 0.0280(5) Uani 1 1 d . . . . .
C7A C 0.4304(3) 0.43243(19) 0.43474(16) 0.0295(5) Uani 1 1 d . . . . .
H9A H 0.388389 0.482516 0.470311 0.035 Uiso 1 1 calc R . . . .
C17 C 0.1741(2) 0.70883(19) 0.48199(15) 0.0284(5) Uani 1 1 d . . . . .
C15 C 0.1351(2) 0.87584(19) 0.52986(16) 0.0281(5) Uani 1 1 d . . . . .
H19 H 0.154811 0.940372 0.524686 0.034 Uiso 1 1 calc R . . . .
C5 C -0.0799(2) 0.63501(19) 0.68678(16) 0.0283(5) Uani 1 1 d . . . . .
C10A C 0.5678(2) 0.28664(19) 0.33788(16) 0.0282(5) Uani 1 1 d . . . . .
C18 C 0.2987(2) 0.84129(19) 0.41660(16) 0.0301(5) Uani 1 1 d . . . . .
C20 C 0.4231(2) 0.7895(2) 0.21436(17) 0.0311(5) Uani 1 1 d . . . . .
C10 C -0.0646(2) 0.73315(19) 0.66789(16) 0.0277(5) Uani 1 1 d . . . . .
C6A C 0.5072(2) 0.45587(19) 0.36749(17) 0.0294(5) Uani 1 1 d . . . . .
C18A C 0.2011(2) 0.1785(2) 0.58627(16) 0.0304(5) Uani 1 1 d . . . . .
C6 C -0.0195(3) 0.5672(2) 0.62822(17) 0.0316(6) Uani 1 1 d . . . . .
C7 C 0.0564(3) 0.5918(2) 0.56080(16) 0.0307(5) Uani 1 1 d . . . . .
H9 H 0.093746 0.543396 0.522339 0.037 Uiso 1 1 calc R . . . .
C11 C -0.0036(2) 0.93728(19) 0.64807(16) 0.0298(5) Uani 1 1 d . . . . .
H11 H -0.096391 0.941605 0.659225 0.036 Uiso 1 1 calc R . . . .
H10 H 0.007162 1.002922 0.619631 0.036 Uiso 1 1 calc R . . . .
C11A C 0.5098(3) 0.08164(19) 0.35803(17) 0.0312(5) Uani 1 1 d . . . . .
H10A H 0.492922 0.017020 0.384654 0.037 Uiso 1 1 calc R . . . .
H11A H 0.603930 0.074322 0.352165 0.037 Uiso 1 1 calc R . . . .
C19 C 0.4658(2) 0.7882(2) 0.30694(16) 0.0313(6) Uani 1 1 d . . . . .
H21 H 0.544151 0.734871 0.318022 0.038 Uiso 1 1 calc R . . . .
H22 H 0.487478 0.853234 0.314795 0.038 Uiso 1 1 calc R . . . .
C1A C 0.7606(2) 0.4511(2) 0.25967(17) 0.0322(6) Uani 1 1 d . . . . .
H2A H 0.828472 0.392245 0.279774 0.039 Uiso 1 1 calc R . . . .
H1A H 0.742818 0.495949 0.307001 0.039 Uiso 1 1 calc R . . . .
C12A C 0.4484(3) 0.1068(2) 0.26775(17) 0.0345(6) Uani 1 1 d . . . . .
H13A H 0.362762 0.089981 0.270788 0.041 Uiso 1 1 calc R . . . .
H12A H 0.435949 0.179843 0.251354 0.041 Uiso 1 1 calc R . . . .
C20A C 0.0772(3) 0.2228(2) 0.78948(17) 0.0337(6) Uani 1 1 d . . . . .
C19A C 0.0350(3) 0.2295(2) 0.69611(17) 0.0340(6) Uani 1 1 d . . . . .
H22A H 0.011550 0.165807 0.685784 0.041 Uiso 1 1 calc R . . . .
H21A H -0.042717 0.283857 0.686892 0.041 Uiso 1 1 calc R . . . .
C12 C 0.0682(3) 0.9145(2) 0.73448(17) 0.0336(6) Uani 1 1 d . . . . .
H12 H 0.083626 0.841514 0.752097 0.040 Uiso 1 1 calc R . . . .
H13 H 0.152759 0.932630 0.725946 0.040 Uiso 1 1 calc R . . . .
C1 C -0.2576(2) 0.5632(2) 0.74530(18) 0.0345(6) Uani 1 1 d . . . . .
H1 H -0.242613 0.522352 0.695180 0.041 Uiso 1 1 calc R . . . .
H2 H -0.330418 0.620625 0.731004 0.041 Uiso 1 1 calc R . . . .
C4 C -0.1532(3) 0.6515(2) 0.84068(17) 0.0356(6) Uani 1 1 d . . . . .
H7 H -0.221573 0.713405 0.834193 0.043 Uiso 1 1 calc R . . . .
H8 H -0.071198 0.670350 0.851805 0.043 Uiso 1 1 calc R . . . .
C4A C 0.6612(3) 0.3597(2) 0.16483(16) 0.0338(6) Uani 1 1 d . . . . .
H7A H 0.579407 0.342358 0.150704 0.041 Uiso 1 1 calc R . . . .
H8A H 0.726205 0.296624 0.177670 0.041 Uiso 1 1 calc R . . . .
C25 C 0.4772(3) 0.7137(2) 0.16368(19) 0.0406(7) Uani 1 1 d . . . . .
H27 H 0.541958 0.659435 0.187635 0.049 Uiso 1 1 calc R . . . .
C2A C 0.8073(3) 0.5063(2) 0.17944(19) 0.0395(6) Uani 1 1 d . . . . .
H3A H 0.744139 0.569710 0.163793 0.047 Uiso 1 1 calc R . . . .
H4A H 0.889800 0.523309 0.192258 0.047 Uiso 1 1 calc R . . . .
C13 C -0.0037(3) 0.9704(2) 0.80750(18) 0.0395(6) Uani 1 1 d . . . . .
H15 H -0.028679 1.042821 0.787666 0.047 Uiso 1 1 calc R . . . .
H14 H -0.083128 0.945872 0.821811 0.047 Uiso 1 1 calc R . . . .
C3A C 0.7052(3) 0.4225(2) 0.08872(18) 0.0401(6) Uani 1 1 d . . . . .
H6A H 0.715514 0.385129 0.036448 0.048 Uiso 1 1 calc R . . . .
H5A H 0.639384 0.485089 0.075996 0.048 Uiso 1 1 calc R . . . .
C21 C 0.3282(3) 0.8673(2) 0.1787(2) 0.0435(7) Uani 1 1 d . . . . .
H23 H 0.289608 0.919878 0.212828 0.052 Uiso 1 1 calc R . . . .
C23 C 0.3450(3) 0.7934(2) 0.04273(19) 0.0432(7) Uani 1 1 d . . . . .
H25 H 0.319141 0.795133 -0.015885 0.052 Uiso 1 1 calc R . . . .
C13A C 0.5278(3) 0.0513(2) 0.19718(19) 0.0424(7) Uani 1 1 d . . . . .
H14A H 0.537065 -0.021857 0.211644 0.051 Uiso 1 1 calc R . . . .
H15A H 0.614721 0.065844 0.195123 0.051 Uiso 1 1 calc R . . . .
C2 C -0.2905(3) 0.5000(2) 0.8258(2) 0.0441(7) Uani 1 1 d . . . . .
H4 H -0.371755 0.479394 0.816069 0.053 Uiso 1 1 calc R . . . .
H3 H -0.221978 0.438583 0.835752 0.053 Uiso 1 1 calc R . . . .
C21A C 0.2043(3) 0.1912(3) 0.8139(2) 0.0468(7) Uani 1 1 d . . . . .
H23A H 0.268284 0.175544 0.770251 0.056 Uiso 1 1 calc R . . . .
C3 C -0.1850(3) 0.5811(3) 0.91562(19) 0.0461(7) Uani 1 1 d . . . . .
H5 H -0.115371 0.520089 0.922418 0.055 Uiso 1 1 calc R . . . .
H6 H -0.191379 0.614129 0.970211 0.055 Uiso 1 1 calc R . . . .
C22 C 0.2886(3) 0.8696(3) 0.0931(2) 0.0472(7) Uani 1 1 d . . . . .
H24 H 0.223011 0.923271 0.069325 0.057 Uiso 1 1 calc R . . . .
C25A C -0.0147(3) 0.2461(2) 0.8539(2) 0.0477(7) Uani 1 1 d . . . . .
H27A H -0.102732 0.267823 0.838740 0.057 Uiso 1 1 calc R . . . .
C24 C 0.4386(3) 0.7152(2) 0.0781(2) 0.0468(7) Uani 1 1 d . . . . .
H26 H 0.476864 0.662371 0.044135 0.056 Uiso 1 1 calc R . . . .
C23A C 0.1486(4) 0.2049(3) 0.9641(2) 0.0541(9) Uani 1 1 d . . . . .
H25A H 0.172716 0.198276 1.023506 0.065 Uiso 1 1 calc R . . . .
C22A C 0.2411(4) 0.1816(3) 0.9005(2) 0.0555(9) Uani 1 1 d . . . . .
H24A H 0.328915 0.159238 0.915831 0.067 Uiso 1 1 calc R . . . .
C14 C 0.0782(4) 0.9557(3) 0.8885(2) 0.0565(9) Uani 1 1 d . . . . .
H18 H 0.158169 0.977816 0.873949 0.085 Uiso 1 1 calc GR . . . .
H16 H 0.098029 0.884580 0.910507 0.085 Uiso 1 1 calc GR . . . .
H17 H 0.031152 0.995274 0.933256 0.085 Uiso 1 1 calc GR . . . .
C24A C 0.0216(4) 0.2379(3) 0.9413(2) 0.0592(9) Uani 1 1 d . . . . .
H26A H -0.041708 0.255044 0.985066 0.071 Uiso 1 1 calc R . . . .
C14A C 0.4655(4) 0.0821(3) 0.1082(2) 0.0596(9) Uani 1 1 d . . . . .
H17A H 0.521083 0.048205 0.063729 0.089 Uiso 1 1 calc GR . . . .
H16A H 0.453033 0.154913 0.094853 0.089 Uiso 1 1 calc GR . . . .
H18A H 0.382145 0.063136 0.108872 0.089 Uiso 1 1 calc GR . . . .


_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
F2A C10A 1.358(3) . ?
F1A C6A 1.350(3) . ?
F2 C10 1.356(3) . ?
F1 C6 1.353(3) . ?
O2 C17 1.251(3) . ?
O2A C17A 1.254(3) . ?
O3 C18 1.245(3) . ?
O3A C18A 1.242(3) . ?
O1A C2A 1.429(4) . ?
O1A C3A 1.429(4) . ?
O1 C2 1.422(4) . ?
O1 C3 1.430(4) . ?
N2A C9A 1.400(3) . ?
N2A C15A 1.355(3) . ?
N2A C11A 1.478(3) . ?
N1A C5A 1.408(3) . ?
N1A C1A 1.471(3) . ?
N1A C4A 1.467(3) . ?
N2 C9 1.403(3) . ?
N2 C15 1.352(3) . ?
N2 C11 1.476(3) . ?
N1 C5 1.401(3) . ?
N1 C1 1.466(3) . ?
N1 C4 1.470(3) . ?
N3A C18A 1.336(3) . ?
N3A C19A 1.450(3) . ?
N3 C18 1.338(3) . ?
N3 C19 1.458(3) . ?
C8A C9A 1.405(3) . ?
C8A C17A 1.462(3) . ?
C8A C7A 1.406(3) . ?
C9 C8 1.401(4) . ?
C9 C10 1.416(3) . ?
C8 C17 1.465(3) . ?
C8 C7 1.405(4) . ?
C9A C10A 1.414(3) . ?
C5A C10A 1.383(3) . ?
C5A C6A 1.413(4) . ?
C17A C16A 1.437(3) . ?
C16A C15A 1.368(4) . ?
C16A C18A 1.494(3) . ?
C16 C17 1.440(3) . ?
C16 C15 1.368(4) . ?
C16 C18 1.497(3) . ?
C7A C6A 1.359(4) . ?
C5 C10 1.394(3) . ?
C5 C6 1.405(4) . ?
C20 C19 1.510(4) . ?
C20 C25 1.380(4) . ?
C20 C21 1.382(4) . ?
C6 C7 1.361(4) . ?
C11 C12 1.528(4) . ?
C11A C12A 1.532(4) . ?
C1A C2A 1.514(4) . ?
C12A C13A 1.522(4) . ?
C20A C19A 1.510(4) . ?
C20A C21A 1.383(4) . ?
C20A C25A 1.387(4) . ?
C12 C13 1.521(4) . ?
C1 C2 1.518(4) . ?
C4 C3 1.510(4) . ?
C4A C3A 1.510(4) . ?
C25 C24 1.392(4) . ?
C13 C14 1.518(4) . ?
C21 C22 1.393(4) . ?
C23 C22 1.387(4) . ?
C23 C24 1.375(4) . ?
C13A C14A 1.523(5) . ?
C21A C22A 1.389(4) . ?
C25A C24A 1.401(5) . ?
C23A C22A 1.380(5) . ?
C23A C24A 1.377(5) . ?

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
C2A O1A C3A 109.5(2) . . ?
C2 O1 C3 109.0(2) . . ?
C9A N2A C11A 123.1(2) . . ?
C15A N2A C9A 118.5(2) . . ?
C15A N2A C11A 117.5(2) . . ?
C5A N1A C1A 115.1(2) . . ?
C5A N1A C4A 119.1(2) . . ?
C4A N1A C1A 111.5(2) . . ?
C9 N2 C11 123.2(2) . . ?
C15 N2 C9 118.7(2) . . ?
C15 N2 C11 117.2(2) . . ?
C5 N1 C1 116.2(2) . . ?
C5 N1 C4 120.7(2) . . ?
C1 N1 C4 112.2(2) . . ?
C18A N3A C19A 123.4(2) . . ?
C18 N3 C19 123.5(2) . . ?
C9A C8A C17A 121.6(2) . . ?
C9A C8A C7A 120.4(2) . . ?
C7A C8A C17A 117.9(2) . . ?
N2 C9 C10 123.6(2) . . ?
C8 C9 N2 119.3(2) . . ?
C8 C9 C10 117.0(2) . . ?
C9 C8 C17 121.8(2) . . ?
C9 C8 C7 120.4(2) . . ?
C7 C8 C17 117.7(2) . . ?
N2A C9A C8A 119.6(2) . . ?
N2A C9A C10A 123.6(2) . . ?
C8A C9A C10A 116.7(2) . . ?
N1A C5A C6A 119.3(2) . . ?
C10A C5A N1A 125.5(2) . . ?
C10A C5A C6A 115.1(2) . . ?
O2A C17A C8A 119.9(2) . . ?
O2A C17A C16A 124.7(2) . . ?
C16A C17A C8A 115.4(2) . . ?
C17A C16A C18A 123.8(2) . . ?
C15A C16A C17A 119.5(2) . . ?
C15A C16A C18A 116.6(2) . . ?
N2A C15A C16A 125.3(2) . . ?
C17 C16 C18 123.7(2) . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 C18 116.8(2) . . ?
C6A C7A C8A 119.4(2) . . ?
O2 C17 C8 120.2(2) . . ?
O2 C17 C16 124.6(2) . . ?
C16 C17 C8 115.2(2) . . ?
N2 C15 C16 125.3(2) . . ?
N1 C5 C6 119.6(2) . . ?
C10 C5 N1 124.9(2) . . ?
C10 C5 C6 115.3(2) . . ?
F2A C10A C9A 119.3(2) . . ?
F2A C10A C5A 116.6(2) . . ?
C5A C10A C9A 124.2(2) . . ?
O3 C18 N3 123.7(2) . . ?
O3 C18 C16 121.3(2) . . ?
N3 C18 C16 115.0(2) . . ?
C25 C20 C19 121.2(2) . . ?
C25 C20 C21 118.6(3) . . ?
C21 C20 C19 120.2(2) . . ?
F2 C10 C9 119.7(2) . . ?
F2 C10 C5 116.6(2) . . ?
C5 C10 C9 123.7(2) . . ?
F1A C6A C5A 117.1(2) . . ?
F1A C6A C7A 119.2(2) . . ?
C7A C6A C5A 123.5(2) . . ?
O3A C18A N3A 123.6(2) . . ?
O3A C18A C16A 121.2(2) . . ?
N3A C18A C16A 115.2(2) . . ?
F1 C6 C5 117.2(2) . . ?
F1 C6 C7 119.0(2) . . ?
C7 C6 C5 123.5(2) . . ?
C6 C7 C8 119.6(2) . . ?
N2 C11 C12 111.0(2) . . ?
N2A C11A C12A 110.8(2) . . ?
N3 C19 C20 111.7(2) . . ?
N1A C1A C2A 110.7(2) . . ?
C13A C12A C11A 113.5(2) . . ?
C21A C20A C19A 122.4(2) . . ?
C21A C20A C25A 118.4(3) . . ?
C25A C20A C19A 119.2(3) . . ?
N3A C19A C20A 113.5(2) . . ?
C13 C12 C11 113.3(2) . . ?
N1 C1 C2 110.0(2) . . ?
N1 C4 C3 108.4(2) . . ?
N1A C4A C3A 108.4(2) . . ?
C20 C25 C24 121.2(3) . . ?
O1A C2A C1A 111.0(2) . . ?
C14 C13 C12 111.3(2) . . ?
O1A C3A C4A 110.6(2) . . ?
C20 C21 C22 120.7(3) . . ?
C24 C23 C22 119.6(3) . . ?
C12A C13A C14A 111.3(3) . . ?
O1 C2 C1 111.5(2) . . ?
C20A C21A C22A 121.7(3) . . ?
O1 C3 C4 110.7(2) . . ?
C23 C22 C21 119.9(3) . . ?
C20A C25A C24A 120.3(3) . . ?
C23 C24 C25 119.9(3) . . ?
C24A C23A C22A 120.0(3) . . ?
C23A C22A C21A 119.4(3) . . ?
C23A C24A C25A 120.2(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_p21_c_225k
_database_code_depnum_ccdc_archive 'CCDC 2386807'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2025-01-14
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.0544(2)
_cell_length_b                   15.1710(4)
_cell_length_c                   24.6379(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.1470(10)
_cell_angle_gamma                90
_cell_volume                     2253.90(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0914 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9549.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            30122
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      225.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                3870
_reflns_number_total             5580
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5580
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0614
_refine_ls_restrained_S_all      1.074
_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)+(0.0736P)²+1.8501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1925
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C14 \\sim C14A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C14A \\sim C14: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C13A \\sim C13: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
3. Others
 Fixed Sof: C13A(0.2) H14A(0.2) H15A(0.2) C14A(0.8) H16A(0.8) H18A(0.8)
 H17A(0.8) C13(0.8) H14(0.8) H15(0.8) C14(0.2) H16(0.2) H18(0.2) H17(0.2)
4.a Secondary CH2 refined with riding coordinates:
 C11(H10,H11), C19(H21,H22), C1(H1,H2), C4(H7,H8), C3(H5,H6), C13A(H14A,H15A),
 C13(H14,H15)
4.b Aromatic/amide H refined with riding coordinates:
 C15(H19), C7(H9), C21(H23), C25(H27), C22(H24), C23(H25), C24(H26)
4.c Idealised Me refined as rotating group:
 C14A(H16A,H18A,H17A), C14(H16,H18,H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F2 F 0.8276(2) 0.33170(9) 0.40225(5) 0.0497(3) Uani 1 1 d . . . . .
F1 F 0.8097(2) 0.45271(10) 0.22629(5) 0.0536(4) Uani 1 1 d . . . . .
O1 O 1.2472(3) 0.18598(12) 0.26659(8) 0.0580(5) Uani 1 1 d . . . . .
N2 N 0.4493(3) 0.43570(11) 0.42518(7) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.2097(3) 0.60804(13) 0.30581(7) 0.0581(5) Uani 1 1 d . . . . .
O3 O -0.0903(3) 0.58754(13) 0.45316(7) 0.0579(5) Uani 1 1 d . . . . .
N1 N 0.9831(3) 0.32317(12) 0.30498(7) 0.0393(4) Uani 1 1 d . . . . .
N3 N -0.1060(3) 0.65128(13) 0.36969(8) 0.0441(4) Uani 1 1 d . . . . .
C9 C 0.5522(3) 0.44038(12) 0.37647(8) 0.0323(4) Uani 1 1 d . . . . .
C10 C 0.7324(3) 0.38751(13) 0.36435(8) 0.0344(4) Uani 1 1 d . . . . .
C8 C 0.4707(3) 0.50005(13) 0.33623(8) 0.0347(4) Uani 1 1 d . . . . .
C15 C 0.2695(3) 0.48624(13) 0.43104(8) 0.0349(4) Uani 1 1 d . . . . .
H19 H 0.199634 0.479787 0.463373 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8203(3) 0.38633(13) 0.31396(8) 0.0351(4) Uani 1 1 d . . . . .
C17 C 0.2781(3) 0.55640(14) 0.34294(8) 0.0386(4) Uani 1 1 d . . . . .
C16 C 0.1809(3) 0.54614(13) 0.39369(8) 0.0354(4) Uani 1 1 d . . . . .
C18 C -0.0171(3) 0.59647(14) 0.40840(9) 0.0394(4) Uani 1 1 d . . . . .
C6 C 0.7327(3) 0.44938(14) 0.27639(8) 0.0390(4) Uani 1 1 d . . . . .
C11 C 0.5102(4) 0.36998(14) 0.46815(8) 0.0412(5) Uani 1 1 d . . . . .
H10 H 0.451609 0.388543 0.502151 0.049 Uiso 1 1 calc R U . . .
H11 H 0.672120 0.366734 0.474607 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5674(4) 0.50574(14) 0.28673(9) 0.0406(5) Uani 1 1 d . . . . .
H9 H 0.517946 0.548441 0.260782 0.049 Uiso 1 1 calc R U . . .
C19 C -0.2985(4) 0.70529(16) 0.37661(10) 0.0471(5) Uani 1 1 d . . . . .
H21 H -0.366044 0.685598 0.409201 0.056 Uiso 1 1 calc R U . . .
H22 H -0.407584 0.696582 0.345212 0.056 Uiso 1 1 calc R U . . .
C1 C 1.1289(4) 0.33765(16) 0.26123(9) 0.0453(5) Uani 1 1 d . . . . .
H1 H 1.182734 0.398589 0.262141 0.054 Uiso 1 1 calc R U . . .
H2 H 1.047547 0.326903 0.225641 0.054 Uiso 1 1 calc R U . . .
C4 C 0.9046(4) 0.23093(15) 0.30300(10) 0.0453(5) Uani 1 1 d . . . . .
H7 H 0.814199 0.220338 0.268605 0.054 Uiso 1 1 calc R U . . .
H8 H 0.812094 0.220173 0.332989 0.054 Uiso 1 1 calc R U . . .
C20 C -0.2460(4) 0.80250(16) 0.38211(10) 0.0469(5) Uani 1 1 d . . . . .
C2 C 1.3202(4) 0.27482(18) 0.27017(11) 0.0516(6) Uani 1 1 d . . . . .
C12 C 0.4185(5) 0.27905(17) 0.45192(12) 0.0553(6) Uani 1 1 d . . . . .
C3 C 1.0999(4) 0.16902(17) 0.30763(12) 0.0560(6) Uani 1 1 d . . . . .
H5 H 1.180720 0.175558 0.343684 0.067 Uiso 1 1 calc R U . . .
H6 H 1.046421 0.108133 0.304182 0.067 Uiso 1 1 calc R U . . .
C21 C -0.4081(5) 0.86413(18) 0.36583(11) 0.0561(6) Uani 1 1 d . . . . .
H23 H -0.548591 0.844877 0.351182 0.067 Uiso 1 1 calc R U . . .
C25 C -0.0411(5) 0.8325(2) 0.40358(14) 0.0683(8) Uani 1 1 d . . . . .
H27 H 0.070924 0.791925 0.414925 0.082 Uiso 1 1 calc R U . . .
C22 C -0.3657(6) 0.9537(2) 0.37088(14) 0.0730(9) Uani 1 1 d . . . . .
H24 H -0.476756 0.994697 0.359611 0.088 Uiso 1 1 calc R U . . .
C23 C -0.1624(7) 0.9822(2) 0.39223(17) 0.0860(11) Uani 1 1 d . . . . .
H25 H -0.133637 1.042896 0.395817 0.103 Uiso 1 1 calc R U . . .
C24 C 0.0004(6) 0.9222(2) 0.40849(18) 0.0888(11) Uani 1 1 d . . . . .
H26 H 0.140506 0.941998 0.423010 0.107 Uiso 1 1 calc R U . . .
C13A C 0.430(6) 0.211(3) 0.4895(16) 0.098(10) Uani 0.2 1 d . U P A 2
H14A H 0.312048 0.222096 0.513343 0.118 Uiso 0.2 1 calc R U P A 2
H15A H 0.570584 0.218923 0.512001 0.118 Uiso 0.2 1 calc R U P A 2
C14A C 0.4166(15) 0.1181(4) 0.4753(4) 0.110(3) Uani 0.8 1 d . U P A 2
H16A H 0.448099 0.110501 0.437650 0.164 Uiso 0.8 1 calc R U P A 2
H18A H 0.268659 0.096469 0.479847 0.164 Uiso 0.8 1 calc R U P A 2
H17A H 0.524034 0.085323 0.498886 0.164 Uiso 0.8 1 calc R U P A 2
H20 H -0.050(5) 0.650(2) 0.3374(14) 0.074(9) Uiso 1 1 d . . . . .
H3 H 1.425(5) 0.2823(19) 0.2404(12) 0.061(8) Uiso 1 1 d . . . . .
H4 H 1.400(5) 0.2869(19) 0.3077(12) 0.062(8) Uiso 1 1 d . . . . .
C13 C 0.5300(12) 0.2069(5) 0.4876(3) 0.0728(18) Uani 0.8 1 d . U P A 1
H14 H 0.554095 0.222664 0.526248 0.087 Uiso 0.8 1 calc R U P A 1
H15 H 0.666058 0.183764 0.474155 0.087 Uiso 0.8 1 calc R U P A 1
C14 C 0.271(7) 0.133(2) 0.4701(15) 0.135(15) Uani 0.2 1 d . U P A 1
H16 H 0.284468 0.103360 0.435615 0.203 Uiso 0.2 1 calc R U P A 1
H18 H 0.138755 0.169266 0.467255 0.203 Uiso 0.2 1 calc R U P A 1
H17 H 0.261189 0.089424 0.498563 0.203 Uiso 0.2 1 calc R U P A 1
H13 H 0.247(10) 0.268(4) 0.458(2) 0.162 Uiso 1 1 d . U . B 1
H12 H 0.448(9) 0.266(4) 0.413(2) 0.162 Uiso 1 1 d . U . C 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C10 1.351(2) . ?
F1 C6 1.359(2) . ?
O1 C2 1.419(3) . ?
O1 C3 1.430(3) . ?
N2 C9 1.403(2) . ?
N2 C15 1.349(2) . ?
N2 C11 1.477(3) . ?
O2 C17 1.247(3) . ?
O3 C18 1.232(2) . ?
N1 C5 1.406(3) . ?
N1 C1 1.470(3) . ?
N1 C4 1.477(3) . ?
N3 C18 1.341(3) . ?
N3 C19 1.447(3) . ?
N3 H20 0.89(3) . ?
C9 C10 1.408(3) . ?
C9 C8 1.399(3) . ?
C10 C5 1.394(3) . ?
C8 C17 1.467(3) . ?
C8 C7 1.402(3) . ?
C15 H19 0.9400 . ?
C15 C16 1.368(3) . ?
C5 C6 1.402(3) . ?
C17 C16 1.437(3) . ?
C16 C18 1.493(3) . ?
C6 C7 1.358(3) . ?
C11 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 C12 1.527(3) . ?
C7 H9 0.9400 . ?
C19 H21 0.9800 . ?
C19 H22 0.9800 . ?
C19 C20 1.512(3) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 C2 1.501(3) . ?
C4 H7 0.9800 . ?
C4 H8 0.9800 . ?
C4 C3 1.506(3) . ?
C20 C21 1.388(3) . ?
C20 C25 1.382(4) . ?
C2 H3 1.02(3) . ?
C2 H4 1.02(3) . ?
C12 C13A 1.38(4) . ?
C12 C13 1.524(7) . ?
C12 H13 1.07(6) . ?
C12 H12 1.01(6) . ?
C3 H5 0.9800 . ?
C3 H6 0.9800 . ?
C21 H23 0.9400 . ?
C21 C22 1.386(4) . ?
C25 H27 0.9400 . ?
C25 C24 1.386(5) . ?
C22 H24 0.9400 . ?
C22 C23 1.365(5) . ?
C23 H25 0.9400 . ?
C23 C24 1.375(5) . ?
C24 H26 0.9400 . ?
C13A H14A 0.9800 . ?
C13A H15A 0.9800 . ?
C13A C14A 1.46(4) . ?
C14A H16A 0.9700 . ?
C14A H18A 0.9700 . ?
C14A H17A 0.9700 . ?
C13 H14 0.9800 . ?
C13 H15 0.9800 . ?
C13 C14 1.94(4) . ?
C14 H16 0.9700 . ?
C14 H18 0.9700 . ?
C14 H17 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.72(18) . . ?
C9 N2 C11 123.08(16) . . ?
C15 N2 C9 119.16(17) . . ?
C15 N2 C11 117.32(16) . . ?
C5 N1 C1 119.29(18) . . ?
C5 N1 C4 115.02(16) . . ?
C1 N1 C4 109.27(16) . . ?
C18 N3 C19 122.92(19) . . ?
C18 N3 H20 118(2) . . ?
C19 N3 H20 119(2) . . ?
N2 C9 C10 124.39(17) . . ?
C8 C9 N2 118.92(17) . . ?
C8 C9 C10 116.68(17) . . ?
F2 C10 C9 120.08(17) . . ?
F2 C10 C5 115.75(17) . . ?
C5 C10 C9 124.15(18) . . ?
C9 C8 C17 122.03(17) . . ?
C9 C8 C7 120.54(18) . . ?
C7 C8 C17 117.39(18) . . ?
N2 C15 H19 117.4 . . ?
N2 C15 C16 125.21(18) . . ?
C16 C15 H19 117.4 . . ?
C10 C5 N1 118.55(18) . . ?
C10 C5 C6 115.29(17) . . ?
C6 C5 N1 126.16(18) . . ?
O2 C17 C8 119.92(18) . . ?
O2 C17 C16 124.84(19) . . ?
C16 C17 C8 115.24(17) . . ?
C15 C16 C17 119.38(18) . . ?
C15 C16 C18 116.82(17) . . ?
C17 C16 C18 123.79(18) . . ?
O3 C18 N3 123.44(19) . . ?
O3 C18 C16 121.46(19) . . ?
N3 C18 C16 115.10(18) . . ?
F1 C6 C5 118.99(18) . . ?
C7 C6 F1 117.76(19) . . ?
C7 C6 C5 123.20(18) . . ?
N2 C11 H10 109.4 . . ?
N2 C11 H11 109.4 . . ?
N2 C11 C12 111.13(19) . . ?
H10 C11 H11 108.0 . . ?
C12 C11 H10 109.4 . . ?
C12 C11 H11 109.4 . . ?
C8 C7 H9 120.1 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H9 120.1 . . ?
N3 C19 H21 108.9 . . ?
N3 C19 H22 108.9 . . ?
N3 C19 C20 113.46(19) . . ?
H21 C19 H22 107.7 . . ?
C20 C19 H21 108.9 . . ?
C20 C19 H22 108.9 . . ?
N1 C1 H1 110.2 . . ?
N1 C1 H2 110.2 . . ?
N1 C1 C2 107.7(2) . . ?
H1 C1 H2 108.5 . . ?
C2 C1 H1 110.2 . . ?
C2 C1 H2 110.2 . . ?
N1 C4 H7 109.7 . . ?
N1 C4 H8 109.7 . . ?
N1 C4 C3 109.89(18) . . ?
H7 C4 H8 108.2 . . ?
C3 C4 H7 109.7 . . ?
C3 C4 H8 109.7 . . ?
C21 C20 C19 119.6(2) . . ?
C25 C20 C19 122.0(2) . . ?
C25 C20 C21 118.4(3) . . ?
O1 C2 C1 111.23(19) . . ?
O1 C2 H3 105.8(16) . . ?
O1 C2 H4 110.3(17) . . ?
C1 C2 H3 110.3(16) . . ?
C1 C2 H4 108.3(16) . . ?
H3 C2 H4 111(2) . . ?
C11 C12 H13 116(3) . . ?
C11 C12 H12 110(3) . . ?
C13A C12 C11 120.2(18) . . ?
C13 C12 C11 111.5(4) . . ?
C13 C12 H13 102(3) . . ?
C13 C12 H12 107(3) . . ?
H13 C12 H12 110(4) . . ?
O1 C3 C4 111.7(2) . . ?
O1 C3 H5 109.3 . . ?
O1 C3 H6 109.3 . . ?
C4 C3 H5 109.3 . . ?
C4 C3 H6 109.3 . . ?
H5 C3 H6 107.9 . . ?
C20 C21 H23 119.6 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H23 119.6 . . ?
C20 C25 H27 119.8 . . ?
C20 C25 C24 120.4(3) . . ?
C24 C25 H27 119.8 . . ?
C21 C22 H24 120.0 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H24 120.0 . . ?
C22 C23 H25 120.0 . . ?
C22 C23 C24 120.0(3) . . ?
C24 C23 H25 120.0 . . ?
C25 C24 H26 119.8 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H26 119.8 . . ?
C12 C13A H14A 106.2 . . ?
C12 C13A H15A 106.2 . . ?
C12 C13A C14A 124(3) . . ?
H14A C13A H15A 106.4 . . ?
C14A C13A H14A 106.2 . . ?
C14A C13A H15A 106.2 . . ?
C13A C14A H16A 109.5 . . ?
C13A C14A H18A 109.5 . . ?
C13A C14A H17A 109.5 . . ?
H16A C14A H18A 109.5 . . ?
H16A C14A H17A 109.5 . . ?
H18A C14A H17A 109.5 . . ?
C12 C13 H14 113.8 . . ?
C12 C13 H15 113.8 . . ?
C12 C13 C14 88.8(13) . . ?
H14 C13 H15 111.1 . . ?
C14 C13 H14 113.8 . . ?
C14 C13 H15 113.8 . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H17 109.5 . . ?
H16 C14 H18 109.5 . . ?
H16 C14 H17 109.5 . . ?
H18 C14 H17 109.5 . . ?

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
F2 C10 C5 N1 5.6(3) . . . . ?
F2 C10 C5 C6 -175.08(17) . . . . ?
F1 C6 C7 C8 175.01(18) . . . . ?
N2 C9 C10 F2 -4.6(3) . . . . ?
N2 C9 C10 C5 173.52(18) . . . . ?
N2 C9 C8 C17 -1.4(3) . . . . ?
N2 C9 C8 C7 -179.13(18) . . . . ?
N2 C15 C16 C17 1.8(3) . . . . ?
N2 C15 C16 C18 -179.17(19) . . . . ?
N2 C11 C12 C13A -170.9(15) . . . . ?
N2 C11 C12 C13 164.4(3) . . . . ?
O2 C17 C16 C15 179.1(2) . . . . ?
O2 C17 C16 C18 0.2(4) . . . . ?
N1 C5 C6 F1 -0.9(3) . . . . ?
N1 C5 C6 C7 176.6(2) . . . . ?
N1 C1 C2 O1 62.5(3) . . . . ?
N1 C4 C3 O1 -55.7(3) . . . . ?
N3 C19 C20 C21 152.3(2) . . . . ?
N3 C19 C20 C25 -28.4(3) . . . . ?
C9 N2 C15 C16 -2.9(3) . . . . ?
C9 N2 C11 C12 -75.5(2) . . . . ?
C9 C10 C5 N1 -172.57(18) . . . . ?
C9 C10 C5 C6 6.7(3) . . . . ?
C9 C8 C17 O2 -179.3(2) . . . . ?
C9 C8 C17 C16 0.3(3) . . . . ?
C9 C8 C7 C6 3.9(3) . . . . ?
C10 C9 C8 C17 177.56(18) . . . . ?
C10 C9 C8 C7 -0.2(3) . . . . ?
C10 C5 C6 F1 179.91(18) . . . . ?
C10 C5 C6 C7 -2.6(3) . . . . ?
C8 C9 C10 F2 176.49(17) . . . . ?
C8 C9 C10 C5 -5.4(3) . . . . ?
C8 C17 C16 C15 -0.5(3) . . . . ?
C8 C17 C16 C18 -179.38(19) . . . . ?
C15 N2 C9 C10 -176.28(18) . . . . ?
C15 N2 C9 C8 2.6(3) . . . . ?
C15 N2 C11 C12 96.8(2) . . . . ?
C15 C16 C18 O3 3.5(3) . . . . ?
C15 C16 C18 N3 -176.79(19) . . . . ?
C5 N1 C1 C2 165.21(18) . . . . ?
C5 N1 C4 C3 -165.6(2) . . . . ?
C5 C6 C7 C8 -2.5(3) . . . . ?
C17 C8 C7 C6 -173.9(2) . . . . ?
C17 C16 C18 O3 -177.6(2) . . . . ?
C17 C16 C18 N3 2.1(3) . . . . ?
C18 N3 C19 C20 109.5(3) . . . . ?
C11 N2 C9 C10 -4.1(3) . . . . ?
C11 N2 C9 C8 174.72(18) . . . . ?
C11 N2 C15 C16 -175.51(19) . . . . ?
C11 C12 C13A C14A -159(2) . . . . ?
C11 C12 C13 C14 156.6(10) . . . . ?
C7 C8 C17 O2 -1.5(3) . . . . ?
C7 C8 C17 C16 178.15(18) . . . . ?
C19 N3 C18 O3 -0.4(4) . . . . ?
C19 N3 C18 C16 179.9(2) . . . . ?
C19 C20 C21 C22 179.4(2) . . . . ?
C19 C20 C25 C24 -179.4(3) . . . . ?
C1 N1 C5 C10 -159.97(18) . . . . ?
C1 N1 C5 C6 20.8(3) . . . . ?
C1 N1 C4 C3 57.1(3) . . . . ?
C4 N1 C5 C10 67.2(2) . . . . ?
C4 N1 C5 C6 -112.0(2) . . . . ?
C4 N1 C1 C2 -59.6(2) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C20 C25 C24 C23 0.2(6) . . . . ?
C2 O1 C3 C4 57.2(3) . . . . ?
C3 O1 C2 C1 -60.9(3) . . . . ?
C21 C20 C25 C24 -0.1(5) . . . . ?
C21 C22 C23 C24 0.3(5) . . . . ?
C25 C20 C21 C22 0.1(4) . . . . ?
C22 C23 C24 C25 -0.3(6) . . . . ?

_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_P-1_140K
_database_code_depnum_ccdc_archive 'CCDC 2386815'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   10.6853(2)
_cell_length_b                   13.7323(3)
_cell_length_c                   15.4315(4)
_cell_angle_alpha                84.1290(10)
_cell_angle_beta                 88.2300(10)
_cell_angle_gamma                77.4240(10)
_cell_volume                     2198.32(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7009
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0992 before and 0.0762 after correction.
The Ratio of minimum to maximum transmission is 0.9403.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            71372
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.438
_diffrn_reflns_theta_min         1.922
_diffrn_ambient_temperature      140(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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                   xray
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6823
_reflns_number_total             9051
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9051
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.089
_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)+(0.0776P)²+2.0484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1850
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C010(H01Y,H), C013(H01A,H01B), C015(H01C,H01D), C016(H01Z,HA), C017(H01E,
 H01F), C018(H01,HB), C019(H0AA,HC), C01A(H01G,H01H), C01B(H01I,H01J),
 C01C(H1AA,HD), C01E(H01K,H01L), C01F(H01M,H01N), C01G(H3AA,HE), C01H(H01O,
 H01P), C01K(H6AA,HF), C01L(H7AA,HG)
2.b Aromatic/amide H refined with riding coordinates:
 N00F(H00F), N00G(H00G), C00P(H00P), C00Q(H00Q), C00V(H00V), C011(H011),
 C01D(H2AA), C01I(H4AA), C01J(H5AA), C01M(H01Q), C01N(H8AA), C01O(H01R),
 C01P(H9AA), C01Q(H01S), C01R(H01T), C01T(H01U)
2.c Idealised Me refined as rotating group:
 C01S(H0BA,HH,HI), C01U(H01V,H01W,H01X)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F2A F 0.35344(12) 0.78510(9) 0.70481(8) 0.0356(3) Uani 1 1 d . . . . .
F1A F 0.48637(13) 0.44749(9) 0.65360(8) 0.0355(3) Uani 1 1 d . . . . .
F2 F 1.13254(12) 0.19811(9) 0.28257(9) 0.0383(3) Uani 1 1 d . . . . .
F1 F 1.02919(13) 0.52994(10) 0.35454(9) 0.0390(3) Uani 1 1 d . . . . .
O2 O 0.77272(15) 0.35885(11) 0.56436(10) 0.0342(3) Uani 1 1 d . . . . .
O2A O 0.73641(15) 0.61876(11) 0.43838(10) 0.0343(3) Uani 1 1 d . . . . .
O3 O 0.68524(16) 0.07167(11) 0.58798(11) 0.0380(4) Uani 1 1 d . . . . .
O1A O 0.17578(16) 0.55337(13) 0.89260(11) 0.0407(4) Uani 1 1 d . . . . .
O3A O 0.81176(17) 0.90985(12) 0.40828(11) 0.0413(4) Uani 1 1 d . . . . .
N2A N 0.54266(16) 0.83880(12) 0.58498(11) 0.0265(4) Uani 1 1 d . . . . .
O1 O 1.30418(18) 0.44617(14) 0.09962(11) 0.0488(4) Uani 1 1 d . . . . .
N2 N 0.95477(16) 0.14191(12) 0.41081(11) 0.0267(4) Uani 1 1 d . . . . .
N1A N 0.35629(16) 0.58234(13) 0.75942(11) 0.0278(4) Uani 1 1 d . . . . .
N1 N 1.14235(16) 0.40019(14) 0.23915(11) 0.0298(4) Uani 1 1 d . . . . .
N3 N 0.63334(17) 0.22956(13) 0.63009(11) 0.0297(4) Uani 1 1 d . . . . .
H20 H 0.649604 0.289994 0.622385 0.036 Uiso 1 1 calc R . . . .
N3A N 0.86756(18) 0.75186(14) 0.36734(11) 0.0316(4) Uani 1 1 d . . . . .
H20A H 0.853233 0.690842 0.375384 0.038 Uiso 1 1 calc R . . . .
C9A C 0.51884(18) 0.74203(14) 0.59874(12) 0.0251(4) Uani 1 1 d . . . . .
C8A C 0.58592(19) 0.66678(15) 0.54910(12) 0.0256(4) Uani 1 1 d . . . . .
C17A C 0.68016(19) 0.68700(15) 0.48270(12) 0.0262(4) Uani 1 1 d . . . . .
C9 C 0.98103(18) 0.23801(15) 0.39803(12) 0.0256(4) Uani 1 1 d . . . . .
C16A C 0.70179(19) 0.78726(15) 0.47457(12) 0.0258(4) Uani 1 1 d . . . . .
C8 C 0.92041(19) 0.31118(15) 0.45157(12) 0.0261(4) Uani 1 1 d . . . . .
C5A C 0.42257(18) 0.61517(15) 0.68583(13) 0.0258(4) Uani 1 1 d . . . . .
C17 C 0.8257(2) 0.29174(15) 0.51811(12) 0.0270(4) Uani 1 1 d . . . . .
C15A C 0.6333(2) 0.85626(15) 0.52585(13) 0.0276(4) Uani 1 1 d . . . . .
H19A H 0.650900 0.921534 0.519401 0.033 Uiso 1 1 calc R . . . .
C7A C 0.5691(2) 0.56775(15) 0.56544(13) 0.0281(4) Uani 1 1 d . . . . .
H9A H 0.610967 0.517671 0.529884 0.034 Uiso 1 1 calc R . . . .
C5 C 1.07992(19) 0.36529(15) 0.31345(13) 0.0268(4) Uani 1 1 d . . . . .
C16 C 0.79957(19) 0.19236(15) 0.52364(12) 0.0263(4) Uani 1 1 d . . . . .
C20 C 0.5766(2) 0.21067(16) 0.78554(13) 0.0296(4) Uani 1 1 d . . . . .
C10 C 1.06493(19) 0.26718(15) 0.33233(13) 0.0264(4) Uani 1 1 d . . . . .
C15 C 0.86474(19) 0.12465(15) 0.47031(13) 0.0270(4) Uani 1 1 d . . . . .
H19 H 0.845117 0.060060 0.475494 0.032 Uiso 1 1 calc R . . . .
C10A C 0.43203(19) 0.71371(15) 0.66226(13) 0.0266(4) Uani 1 1 d . . . . .
C18 C 0.7010(2) 0.15882(15) 0.58350(13) 0.0286(4) Uani 1 1 d . . . . .
C6A C 0.4923(2) 0.54457(15) 0.63257(13) 0.0275(4) Uani 1 1 d . . . . .
C18A C 0.7986(2) 0.82192(16) 0.41387(13) 0.0291(4) Uani 1 1 d . . . . .
C11 C 1.0034(2) 0.06309(15) 0.35214(13) 0.0286(4) Uani 1 1 d . . . . .
H10 H 0.992185 -0.002495 0.380484 0.034 Uiso 1 1 calc R . . . .
H11 H 1.096195 0.058625 0.341194 0.034 Uiso 1 1 calc R . . . .
C7 C 0.9431(2) 0.40887(16) 0.43913(13) 0.0299(4) Uani 1 1 d . . . . .
H9 H 0.905716 0.457275 0.477507 0.036 Uiso 1 1 calc R . . . .
C6 C 1.0192(2) 0.43339(16) 0.37159(14) 0.0303(4) Uani 1 1 d . . . . .
C1A C 0.23928(19) 0.54896(17) 0.74028(14) 0.0314(4) Uani 1 1 d . . . . .
H1A H 0.257134 0.504104 0.693010 0.038 Uiso 1 1 calc R . . . .
H2A H 0.171568 0.607760 0.720168 0.038 Uiso 1 1 calc R . . . .
C20A C 0.9227(2) 0.77770(16) 0.21087(14) 0.0321(5) Uani 1 1 d . . . . .
C11A C 0.4901(2) 0.91832(15) 0.64221(14) 0.0299(4) Uani 1 1 d . . . . .
H11A H 0.396105 0.925176 0.648231 0.036 Uiso 1 1 calc R . . . .
H10A H 0.506514 0.983096 0.615577 0.036 Uiso 1 1 calc R . . . .
C19 C 0.5341(2) 0.21191(16) 0.69297(13) 0.0299(4) Uani 1 1 d . . . . .
H22 H 0.512273 0.146896 0.685145 0.036 Uiso 1 1 calc R . . . .
H21 H 0.455841 0.265193 0.681904 0.036 Uiso 1 1 calc R . . . .
C12A C 0.5516(2) 0.89338(17) 0.73239(14) 0.0331(5) Uani 1 1 d . . . . .
H12A H 0.564155 0.820329 0.748817 0.040 Uiso 1 1 calc R . . . .
H13A H 0.637239 0.910261 0.729097 0.040 Uiso 1 1 calc R . . . .
C12 C 0.9322(2) 0.08611(16) 0.26560(13) 0.0315(4) Uani 1 1 d . . . . .
H13 H 0.847486 0.068081 0.273932 0.038 Uiso 1 1 calc R . . . .
H12 H 0.917047 0.159085 0.248116 0.038 Uiso 1 1 calc R . . . .
C1 C 1.2577(2) 0.43725(17) 0.25492(15) 0.0342(5) Uani 1 1 d . . . . .
H2 H 1.330212 0.379873 0.269510 0.041 Uiso 1 1 calc R . . . .
H1 H 1.242483 0.478317 0.304880 0.041 Uiso 1 1 calc R . . . .
C19A C 0.9648(2) 0.77117(17) 0.30428(14) 0.0328(5) Uani 1 1 d . . . . .
H21A H 1.042511 0.716984 0.313502 0.039 Uiso 1 1 calc R . . . .
H22A H 0.988132 0.834940 0.314559 0.039 Uiso 1 1 calc R . . . .
C4A C 0.3389(2) 0.64023(17) 0.83528(13) 0.0327(5) Uani 1 1 d . . . . .
H7A H 0.274235 0.703335 0.822573 0.039 Uiso 1 1 calc R . . . .
H8A H 0.420827 0.657385 0.849320 0.039 Uiso 1 1 calc R . . . .
C4 C 1.1533(2) 0.34857(18) 0.15980(14) 0.0350(5) Uani 1 1 d . . . . .
H8 H 1.071380 0.329730 0.148667 0.042 Uiso 1 1 calc R . . . .
H7 H 1.221455 0.286697 0.166587 0.042 Uiso 1 1 calc R . . . .
C25 C 0.5219(2) 0.28590(18) 0.83655(15) 0.0399(5) Uani 1 1 d . . . . .
H27 H 0.456700 0.339813 0.812862 0.048 Uiso 1 1 calc R . . . .
C2A C 0.1927(2) 0.49372(18) 0.82087(15) 0.0386(5) Uani 1 1 d . . . . .
H4A H 0.110281 0.476571 0.808202 0.046 Uiso 1 1 calc R . . . .
H3A H 0.255821 0.430417 0.836468 0.046 Uiso 1 1 calc R . . . .
C3A C 0.2947(2) 0.57725(19) 0.91157(15) 0.0394(5) Uani 1 1 d . . . . .
H5A H 0.360264 0.514618 0.924232 0.047 Uiso 1 1 calc R . . . .
H6A H 0.284501 0.614524 0.963867 0.047 Uiso 1 1 calc R . . . .
C13 C 1.0040(2) 0.03040(18) 0.19265(15) 0.0388(5) Uani 1 1 d . . . . .
H14 H 1.028216 -0.042077 0.212243 0.047 Uiso 1 1 calc R . . . .
H15 H 1.083707 0.054622 0.178692 0.047 Uiso 1 1 calc R . . . .
C13A C 0.4728(2) 0.94878(19) 0.80330(15) 0.0417(5) Uani 1 1 d . . . . .
H15A H 0.463647 1.021898 0.788925 0.050 Uiso 1 1 calc R . . . .
H14A H 0.385909 0.934194 0.805643 0.050 Uiso 1 1 calc R . . . .
C23 C 0.6547(2) 0.2067(2) 0.95708(15) 0.0430(6) Uani 1 1 d . . . . .
H25 H 0.680554 0.204809 1.015687 0.052 Uiso 1 1 calc R . . . .
C21 C 0.6729(2) 0.13325(19) 0.82125(16) 0.0433(6) Uani 1 1 d . . . . .
H23 H 0.712391 0.081124 0.786960 0.052 Uiso 1 1 calc R . . . .
C2 C 1.2910(2) 0.49991(19) 0.17453(16) 0.0435(6) Uani 1 1 d . . . . .
H3 H 1.222917 0.561423 0.164424 0.052 Uiso 1 1 calc R . . . .
H4 H 1.372372 0.520393 0.184263 0.052 Uiso 1 1 calc R . . . .
C3 C 1.1858(3) 0.4187(2) 0.08453(15) 0.0448(6) Uani 1 1 d . . . . .
H6 H 1.192463 0.385466 0.030090 0.054 Uiso 1 1 calc R . . . .
H5 H 1.116327 0.479753 0.077382 0.054 Uiso 1 1 calc R . . . .
C21A C 0.7959(2) 0.8099(2) 0.18647(16) 0.0468(6) Uani 1 1 d . . . . .
H23A H 0.731993 0.826073 0.229978 0.056 Uiso 1 1 calc R . . . .
C24 C 0.5605(3) 0.2841(2) 0.92214(16) 0.0458(6) Uani 1 1 d . . . . .
H26 H 0.521676 0.336494 0.956365 0.055 Uiso 1 1 calc R . . . .
C25A C 1.0141(3) 0.7531(2) 0.14659(16) 0.0473(6) Uani 1 1 d . . . . .
H27A H 1.101813 0.730509 0.161826 0.057 Uiso 1 1 calc R . . . .
C22 C 0.7119(3) 0.1313(2) 0.90639(17) 0.0483(6) Uani 1 1 d . . . . .
H24 H 0.778005 0.078059 0.930013 0.058 Uiso 1 1 calc R . . . .
C23A C 0.8517(3) 0.7948(2) 0.03658(17) 0.0547(7) Uani 1 1 d . . . . .
H25A H 0.827775 0.801289 -0.022860 0.066 Uiso 1 1 calc R . . . .
C22A C 0.7597(3) 0.8192(2) 0.09983(18) 0.0562(7) Uani 1 1 d . . . . .
H24A H 0.672134 0.842261 0.084331 0.067 Uiso 1 1 calc R . . . .
C14 C 0.9224(3) 0.0459(2) 0.11132(17) 0.0581(8) Uani 1 1 d . . . . .
H17 H 0.969978 0.007632 0.066016 0.087 Uiso 1 1 calc GR . . . .
H16 H 0.901665 0.117299 0.090299 0.087 Uiso 1 1 calc GR . . . .
H18 H 0.842914 0.022758 0.125237 0.087 Uiso 1 1 calc GR . . . .
C24A C 0.9780(3) 0.7612(2) 0.05944(18) 0.0606(8) Uani 1 1 d . . . . .
H26A H 1.041185 0.743277 0.015823 0.073 Uiso 1 1 calc R . . . .
C14A C 0.5356(3) 0.9177(2) 0.89192(17) 0.0612(8) Uani 1 1 d . . . . .
H18A H 0.619248 0.936244 0.890856 0.092 Uiso 1 1 calc GR . . . .
H16A H 0.547356 0.845008 0.905375 0.092 Uiso 1 1 calc GR . . . .
H17A H 0.480799 0.951887 0.936600 0.092 Uiso 1 1 calc GR . . . .


_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
F2A C10A 1.355(2) . ?
F1A C6A 1.354(2) . ?
F2 C10 1.352(2) . ?
F1 C6 1.352(2) . ?
O2 C17 1.250(2) . ?
O2A C17A 1.252(2) . ?
O3 C18 1.239(3) . ?
O1A C2A 1.428(3) . ?
O1A C3A 1.426(3) . ?
O3A C18A 1.240(3) . ?
N2A C9A 1.401(2) . ?
N2A C15A 1.353(3) . ?
N2A C11A 1.479(3) . ?
O1 C2 1.421(3) . ?
O1 C3 1.429(3) . ?
N2 C9 1.401(3) . ?
N2 C15 1.351(3) . ?
N2 C11 1.479(3) . ?
N1A C5A 1.407(2) . ?
N1A C1A 1.470(2) . ?
N1A C4A 1.466(3) . ?
N1 C5 1.403(3) . ?
N1 C1 1.468(3) . ?
N1 C4 1.466(3) . ?
N3 C18 1.337(3) . ?
N3 C19 1.458(3) . ?
N3A C18A 1.336(3) . ?
N3A C19A 1.450(3) . ?
C9A C8A 1.405(3) . ?
C9A C10A 1.413(3) . ?
C8A C17A 1.463(3) . ?
C8A C7A 1.407(3) . ?
C17A C16A 1.437(3) . ?
C9 C8 1.402(3) . ?
C9 C10 1.417(3) . ?
C16A C15A 1.369(3) . ?
C16A C18A 1.496(3) . ?
C8 C17 1.465(3) . ?
C8 C7 1.408(3) . ?
C5A C10A 1.389(3) . ?
C5A C6A 1.407(3) . ?
C17 C16 1.445(3) . ?
C7A C6A 1.357(3) . ?
C5 C10 1.392(3) . ?
C5 C6 1.404(3) . ?
C16 C15 1.366(3) . ?
C16 C18 1.496(3) . ?
C20 C19 1.510(3) . ?
C20 C25 1.380(3) . ?
C20 C21 1.390(3) . ?
C11 C12 1.528(3) . ?
C7 C6 1.362(3) . ?
C1A C2A 1.517(3) . ?
C20A C19A 1.511(3) . ?
C20A C21A 1.382(3) . ?
C20A C25A 1.384(3) . ?
C11A C12A 1.532(3) . ?
C12A C13A 1.523(3) . ?
C12 C13 1.519(3) . ?
C1 C2 1.514(3) . ?
C4A C3A 1.514(3) . ?
C4 C3 1.513(3) . ?
C25 C24 1.392(3) . ?
C13 C14 1.521(4) . ?
C13A C14A 1.522(4) . ?
C23 C24 1.373(4) . ?
C23 C22 1.385(4) . ?
C21 C22 1.386(3) . ?
C21A C22A 1.389(4) . ?
C25A C24A 1.397(4) . ?
C23A C22A 1.377(4) . ?
C23A C24A 1.373(5) . ?

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
C3A O1A C2A 109.51(17) . . ?
C9A N2A C11A 122.90(16) . . ?
C15A N2A C9A 118.69(17) . . ?
C15A N2A C11A 117.55(17) . . ?
C2 O1 C3 109.20(19) . . ?
C9 N2 C11 123.10(16) . . ?
C15 N2 C9 118.81(17) . . ?
C15 N2 C11 117.19(17) . . ?
C5A N1A C1A 114.97(16) . . ?
C5A N1A C4A 119.14(16) . . ?
C4A N1A C1A 111.75(16) . . ?
C5 N1 C1 116.01(16) . . ?
C5 N1 C4 120.55(17) . . ?
C4 N1 C1 112.36(17) . . ?
C18 N3 C19 123.50(17) . . ?
C18A N3A C19A 123.38(18) . . ?
N2A C9A C8A 119.54(17) . . ?
N2A C9A C10A 123.62(18) . . ?
C8A C9A C10A 116.82(18) . . ?
C9A C8A C17A 121.58(18) . . ?
C9A C8A C7A 120.43(18) . . ?
C7A C8A C17A 117.90(18) . . ?
O2A C17A C8A 119.97(18) . . ?
O2A C17A C16A 124.68(18) . . ?
C16A C17A C8A 115.35(17) . . ?
N2 C9 C8 119.22(17) . . ?
N2 C9 C10 123.73(18) . . ?
C8 C9 C10 117.04(18) . . ?
C17A C16A C18A 123.84(18) . . ?
C15A C16A C17A 119.61(18) . . ?
C15A C16A C18A 116.54(18) . . ?
C9 C8 C17 122.00(18) . . ?
C9 C8 C7 120.44(18) . . ?
C7 C8 C17 117.44(18) . . ?
N1A C5A C6A 119.61(18) . . ?
C10A C5A N1A 125.24(18) . . ?
C10A C5A C6A 115.06(18) . . ?
O2 C17 C8 120.40(18) . . ?
O2 C17 C16 124.62(18) . . ?
C16 C17 C8 114.98(18) . . ?
N2A C15A C16A 125.15(19) . . ?
C6A C7A C8A 119.25(19) . . ?
N1 C5 C6 119.48(18) . . ?
C10 C5 N1 124.82(19) . . ?
C10 C5 C6 115.55(18) . . ?
C17 C16 C18 123.67(18) . . ?
C15 C16 C17 119.42(18) . . ?
C15 C16 C18 116.89(18) . . ?
C25 C20 C19 121.2(2) . . ?
C25 C20 C21 118.4(2) . . ?
C21 C20 C19 120.4(2) . . ?
F2 C10 C9 119.62(17) . . ?
F2 C10 C5 116.77(17) . . ?
C5 C10 C9 123.58(18) . . ?
N2 C15 C16 125.42(19) . . ?
F2A C10A C9A 119.49(17) . . ?
F2A C10A C5A 116.60(17) . . ?
C5A C10A C9A 123.90(18) . . ?
O3 C18 N3 123.92(19) . . ?
O3 C18 C16 121.20(19) . . ?
N3 C18 C16 114.88(18) . . ?
F1A C6A C5A 116.99(17) . . ?
F1A C6A C7A 119.07(18) . . ?
C7A C6A C5A 123.84(18) . . ?
O3A C18A N3A 123.61(19) . . ?
O3A C18A C16A 121.22(19) . . ?
N3A C18A C16A 115.17(18) . . ?
N2 C11 C12 110.85(16) . . ?
C6 C7 C8 119.42(19) . . ?
F1 C6 C5 117.40(18) . . ?
F1 C6 C7 118.89(19) . . ?
C7 C6 C5 123.48(19) . . ?
N1A C1A C2A 110.46(17) . . ?
C21A C20A C19A 122.4(2) . . ?
C21A C20A C25A 118.3(2) . . ?
C25A C20A C19A 119.3(2) . . ?
N2A C11A C12A 110.72(16) . . ?
N3 C19 C20 111.80(17) . . ?
C13A C12A C11A 113.63(19) . . ?
C13 C12 C11 113.33(18) . . ?
N1 C1 C2 109.92(18) . . ?
N3A C19A C20A 113.48(18) . . ?
N1A C4A C3A 108.37(18) . . ?
N1 C4 C3 108.33(19) . . ?
C20 C25 C24 121.1(2) . . ?
O1A C2A C1A 111.13(19) . . ?
O1A C3A C4A 110.53(18) . . ?
C12 C13 C14 111.2(2) . . ?
C14A C13A C12A 111.3(2) . . ?
C24 C23 C22 119.6(2) . . ?
C22 C21 C20 120.7(2) . . ?
O1 C2 C1 111.6(2) . . ?
O1 C3 C4 110.59(19) . . ?
C20A C21A C22A 121.5(2) . . ?
C23 C24 C25 120.0(2) . . ?
C20A C25A C24A 120.4(3) . . ?
C23 C22 C21 120.2(2) . . ?
C24A C23A C22A 120.0(3) . . ?
C23A C22A C21A 119.5(3) . . ?
C23A C24A C25A 120.3(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_p21_c_298k
_database_code_depnum_ccdc_archive 'CCDC 2386802'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2025-01-14
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.105(C25 H27 F2 N3 O3)'
_chemical_formula_sum            'C2.63 H2.84 F0.21 N0.32 O0.32'
_chemical_formula_weight         47.95
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.0713(2)
_cell_length_b                   15.0980(5)
_cell_length_c                   24.9433(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.4230(10)
_cell_angle_gamma                90
_cell_volume                     2279.61(13)
_cell_formula_units_Z            38
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7122
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28085
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.122
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                3200
_reflns_number_total             4668
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4668
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0689
_refine_ls_restrained_S_all      1.078
_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)+(0.0985P)²+1.5975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2268
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C13 \\sim C13A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C14A \\sim C14: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C13A \\sim C13: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C12A \\sim C12: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
Uanis(C14A) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C11) = Uanis(C13A)
3. Rigid body (RIGU) restrains
 C14A, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: C12A(0.7) H13A(0.7) H12A(0.7) C13A(0.7) H14A(0.7) H15A(0.7)
 C14A(0.7) H16A(0.7) H17A(0.7) H18A(0.7) C12(0.3) H12(0.3) H13(0.3) C13(0.3)
 H15(0.3) H14(0.3) C14(0.3) H16(0.3) H17(0.3) H18(0.3)
5.a Secondary CH2 refined with riding coordinates:
 C19(H22,H21), C1(H2,H1), C4(H7,H8), C12A(H13A,H12A), C3(H6,H5), C13A(H14A,
 H15A), C12(H12,H13), C13(H15,H14)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H19), C7(H9), C21(H23), C25(H27), C22(H24), C23(H25), C24(H26)
5.c Idealised Me refined as rotating group:
 C14A(H16A,H17A,H18A), C14(H16,H17,H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F2 F 0.8272(3) 0.67008(12) 0.40175(7) 0.0702(5) Uani 1 1 d . . . . .
F1 F 0.8095(3) 0.55110(13) 0.22750(7) 0.0769(6) Uani 1 1 d . . . . .
N2 N 0.4489(3) 0.56576(14) 0.42477(8) 0.0498(5) Uani 1 1 d . . . . .
O1 O 1.2483(4) 0.81685(16) 0.26759(10) 0.0830(7) Uani 1 1 d . . . . .
O2 O 0.2132(4) 0.39348(17) 0.30708(9) 0.0813(7) Uani 1 1 d . . . . .
N1 N 0.9819(4) 0.68014(15) 0.30521(9) 0.0563(6) Uani 1 1 d . . . . .
O3 O -0.0919(4) 0.41457(17) 0.45237(9) 0.0804(7) Uani 1 1 d . . . . .
N3 N -0.1034(4) 0.34978(17) 0.37033(10) 0.0625(6) Uani 1 1 d . . . . .
C9 C 0.5522(4) 0.56142(15) 0.37643(9) 0.0460(5) Uani 1 1 d . . . . .
C10 C 0.7318(4) 0.61458(17) 0.36423(10) 0.0502(6) Uani 1 1 d . . . . .
C8 C 0.4708(4) 0.50224(17) 0.33657(10) 0.0505(6) Uani 1 1 d . . . . .
C16 C 0.1819(4) 0.45533(16) 0.39380(10) 0.0502(6) Uani 1 1 d . . . . .
C15 C 0.2701(4) 0.51498(17) 0.43081(10) 0.0496(6) Uani 1 1 d . . . . .
H19 H 0.201068 0.520916 0.462633 0.060 Uiso 1 1 calc R U . . .
C5 C 0.8197(4) 0.61650(17) 0.31434(10) 0.0503(6) Uani 1 1 d . . . . .
C17 C 0.2799(5) 0.44553(18) 0.34369(11) 0.0560(6) Uani 1 1 d . . . . .
C18 C -0.0162(4) 0.40494(18) 0.40835(11) 0.0561(6) Uani 1 1 d . . . . .
C6 C 0.7324(5) 0.55384(18) 0.27718(11) 0.0557(6) Uani 1 1 d . . . . .
C7 C 0.5678(5) 0.49713(18) 0.28757(11) 0.0572(7) Uani 1 1 d . . . . .
H9 H 0.519498 0.454927 0.262167 0.069 Uiso 1 1 calc R U . . .
C11 C 0.5122(6) 0.6307(2) 0.46742(13) 0.0685(7) Uani 1 1 d . . . . .
H11 H 0.685(6) 0.633(2) 0.4753(14) 0.082 Uiso 1 1 d . U . A 1
H10 H 0.452(6) 0.611(2) 0.4951(14) 0.082 Uiso 1 1 d . U . B 1
C19 C -0.2965(5) 0.2957(2) 0.37692(13) 0.0655(8) Uani 1 1 d . . . . .
H22 H -0.402385 0.304955 0.346293 0.079 Uiso 1 1 calc R U . . .
H21 H -0.364593 0.315149 0.408815 0.079 Uiso 1 1 calc R U . . .
C20 C -0.2472(5) 0.1984(2) 0.38195(12) 0.0647(7) Uani 1 1 d . . . . .
C1 C 1.1304(5) 0.6649(2) 0.26217(13) 0.0671(8) Uani 1 1 d . . . . .
H2 H 1.052317 0.675016 0.227302 0.081 Uiso 1 1 calc R U . . .
H1 H 1.183869 0.604377 0.263469 0.081 Uiso 1 1 calc R U . . .
C4 C 0.9061(5) 0.77236(19) 0.30346(14) 0.0670(8) Uani 1 1 d . . . . .
H7 H 0.814048 0.783194 0.332881 0.080 Uiso 1 1 calc R U . . .
H8 H 0.817909 0.783085 0.269988 0.080 Uiso 1 1 calc R U . . .
C2 C 1.3194(5) 0.7280(3) 0.27071(16) 0.0753(9) Uani 1 1 d . . . . .
C21 C -0.4079(7) 0.1376(2) 0.36575(14) 0.0809(10) Uani 1 1 d . . . . .
H23 H -0.544973 0.157538 0.351408 0.097 Uiso 1 1 calc R U . . .
C12A C 0.4314(15) 0.7247(6) 0.4527(4) 0.081(3) Uani 0.7 1 d . U P C 2
H13A H 0.463366 0.737795 0.416051 0.097 Uiso 0.7 1 calc R U P C 2
H12A H 0.272597 0.727554 0.454593 0.097 Uiso 0.7 1 calc R U P C 2
C3 C 1.0993(6) 0.8341(2) 0.30774(17) 0.0828(10) Uani 1 1 d . . . . .
H6 H 1.046618 0.894618 0.304126 0.099 Uiso 1 1 calc R U . . .
H5 H 1.176975 0.827985 0.343011 0.099 Uiso 1 1 calc R U . . .
C25 C -0.0454(7) 0.1670(3) 0.4023(2) 0.0977(12) Uani 1 1 d . . . . .
H27 H 0.066388 0.206711 0.413176 0.117 Uiso 1 1 calc R U . . .
C22 C -0.3693(10) 0.0475(3) 0.37039(19) 0.1034(14) Uani 1 1 d . . . . .
H24 H -0.479854 0.007394 0.359367 0.124 Uiso 1 1 calc R U . . .
C23 C -0.1697(11) 0.0179(3) 0.3911(2) 0.1215(18) Uani 1 1 d . . . . .
H25 H -0.143942 -0.042578 0.394535 0.146 Uiso 1 1 calc R U . . .
C24 C -0.0066(9) 0.0766(4) 0.4068(3) 0.1283(19) Uani 1 1 d . . . . .
H26 H 0.130713 0.056070 0.420492 0.154 Uiso 1 1 calc R U . . .
C13A C 0.5362(10) 0.7907(3) 0.48852(19) 0.0685(7) Uani 0.7 1 d . U P C 2
H14A H 0.693110 0.793144 0.483709 0.082 Uiso 0.7 1 calc R U P C 2
H15A H 0.517958 0.774690 0.525570 0.082 Uiso 0.7 1 calc R U P C 2
C14A C 0.430(2) 0.8829(6) 0.4760(6) 0.156(6) Uani 0.7 1 d . U P C 2
H16A H 0.421070 0.893238 0.437954 0.233 Uiso 0.7 1 calc R U P C 2
H17A H 0.518830 0.928174 0.494012 0.233 Uiso 0.7 1 calc R U P C 2
H18A H 0.284126 0.884322 0.488454 0.233 Uiso 0.7 1 calc R U P C 2
H3 H 1.420(6) 0.722(2) 0.2429(14) 0.081(10) Uiso 1 1 d . . . . .
H4 H 1.390(6) 0.712(3) 0.3096(17) 0.096(12) Uiso 1 1 d . . . . .
H20 H -0.033(7) 0.353(3) 0.3368(17) 0.101(13) Uiso 1 1 d . . . . .
C12 C 0.390(4) 0.7183(17) 0.4555(8) 0.103(8) Uani 0.3 1 d . U P C 1
H12 H 0.425938 0.734406 0.419513 0.123 Uiso 0.3 1 calc R U P C 1
H13 H 0.235001 0.702695 0.452443 0.123 Uiso 0.3 1 calc R U P C 1
C13 C 0.402(4) 0.7992(14) 0.4849(8) 0.128(7) Uani 0.3 1 d . U P C 1
H15 H 0.375813 0.785337 0.521891 0.153 Uiso 0.3 1 calc R U P C 1
H14 H 0.552101 0.820975 0.485040 0.153 Uiso 0.3 1 calc R U P C 1
C14 C 0.264(6) 0.867(2) 0.4688(14) 0.184(16) Uani 0.3 1 d . U P C 1
H16 H 0.256443 0.872282 0.430328 0.276 Uiso 0.3 1 calc R U P C 1
H17 H 0.319092 0.921567 0.484692 0.276 Uiso 0.3 1 calc R U P C 1
H18 H 0.118731 0.855793 0.480026 0.276 Uiso 0.3 1 calc R U P C 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C10 1.353(3) . ?
F1 C6 1.359(3) . ?
N2 C9 1.403(3) . ?
N2 C15 1.347(3) . ?
N2 C11 1.476(4) . ?
O1 C2 1.409(4) . ?
O1 C3 1.425(4) . ?
O2 C17 1.248(3) . ?
N1 C5 1.407(3) . ?
N1 C1 1.472(3) . ?
N1 C4 1.466(4) . ?
O3 C18 1.231(3) . ?
N3 C18 1.340(4) . ?
N3 C19 1.448(4) . ?
N3 H20 0.97(4) . ?
C9 C10 1.406(3) . ?
C9 C8 1.398(4) . ?
C10 C5 1.392(3) . ?
C8 C17 1.463(4) . ?
C8 C7 1.399(3) . ?
C16 C15 1.369(4) . ?
C16 C17 1.433(4) . ?
C16 C18 1.491(4) . ?
C15 H19 0.9300 . ?
C5 C6 1.400(4) . ?
C6 C7 1.356(4) . ?
C7 H9 0.9300 . ?
C11 H11 1.05(4) . ?
C11 H10 0.86(4) . ?
C11 C12A 1.536(10) . ?
C11 C12 1.53(3) . ?
C19 H22 0.9700 . ?
C19 H21 0.9700 . ?
C19 C20 1.502(4) . ?
C20 C21 1.377(5) . ?
C20 C25 1.374(5) . ?
C1 H2 0.9700 . ?
C1 H1 0.9700 . ?
C1 C2 1.494(5) . ?
C4 H7 0.9700 . ?
C4 H8 0.9700 . ?
C4 C3 1.495(4) . ?
C2 H3 0.96(4) . ?
C2 H4 1.06(4) . ?
C21 H23 0.9300 . ?
C21 C22 1.384(6) . ?
C12A H13A 0.9700 . ?
C12A H12A 0.9700 . ?
C12A C13A 1.452(11) . ?
C3 H6 0.9700 . ?
C3 H5 0.9700 . ?
C25 H27 0.9300 . ?
C25 C24 1.388(6) . ?
C22 H24 0.9300 . ?
C22 C23 1.355(7) . ?
C23 H25 0.9300 . ?
C23 C24 1.364(8) . ?
C24 H26 0.9300 . ?
C13A H14A 0.9700 . ?
C13A H15A 0.9700 . ?
C13A C14A 1.556(14) . ?
C14A H16A 0.9600 . ?
C14A H17A 0.9600 . ?
C14A H18A 0.9600 . ?
C12 H12 0.9700 . ?
C12 H13 0.9700 . ?
C12 C13 1.42(3) . ?
C13 H15 0.9700 . ?
C13 H14 0.9700 . ?
C13 C14 1.37(4) . ?
C14 H16 0.9600 . ?
C14 H17 0.9600 . ?
C14 H18 0.9600 . ?

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
C9 N2 C11 122.8(2) . . ?
C15 N2 C9 119.2(2) . . ?
C15 N2 C11 117.7(2) . . ?
C2 O1 C3 110.1(2) . . ?
C5 N1 C1 119.2(2) . . ?
C5 N1 C4 115.6(2) . . ?
C4 N1 C1 109.6(2) . . ?
C18 N3 C19 123.3(2) . . ?
C18 N3 H20 114(2) . . ?
C19 N3 H20 123(2) . . ?
N2 C9 C10 124.4(2) . . ?
C8 C9 N2 118.9(2) . . ?
C8 C9 C10 116.6(2) . . ?
F2 C10 C9 120.1(2) . . ?
F2 C10 C5 115.6(2) . . ?
C5 C10 C9 124.3(2) . . ?
C9 C8 C17 121.8(2) . . ?
C9 C8 C7 120.5(2) . . ?
C7 C8 C17 117.7(2) . . ?
C15 C16 C17 119.3(2) . . ?
C15 C16 C18 116.9(2) . . ?
C17 C16 C18 123.8(2) . . ?
N2 C15 C16 125.2(2) . . ?
N2 C15 H19 117.4 . . ?
C16 C15 H19 117.4 . . ?
C10 C5 N1 118.7(2) . . ?
C10 C5 C6 115.2(2) . . ?
C6 C5 N1 126.0(2) . . ?
O2 C17 C8 119.7(2) . . ?
O2 C17 C16 124.7(2) . . ?
C16 C17 C8 115.6(2) . . ?
O3 C18 N3 123.4(3) . . ?
O3 C18 C16 121.4(3) . . ?
N3 C18 C16 115.3(2) . . ?
F1 C6 C5 119.0(2) . . ?
C7 C6 F1 117.8(3) . . ?
C7 C6 C5 123.2(2) . . ?
C8 C7 H9 120.1 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H9 120.1 . . ?
N2 C11 H11 110.7(19) . . ?
N2 C11 H10 104(2) . . ?
N2 C11 C12A 112.4(5) . . ?
N2 C11 C12 109.8(7) . . ?
H11 C11 H10 110(3) . . ?
C12 C11 H11 118(2) . . ?
C12 C11 H10 103(3) . . ?
N3 C19 H22 108.8 . . ?
N3 C19 H21 108.8 . . ?
N3 C19 C20 113.8(3) . . ?
H22 C19 H21 107.7 . . ?
C20 C19 H22 108.8 . . ?
C20 C19 H21 108.8 . . ?
C21 C20 C19 119.7(3) . . ?
C25 C20 C19 122.3(3) . . ?
C25 C20 C21 118.0(3) . . ?
N1 C1 H2 110.2 . . ?
N1 C1 H1 110.2 . . ?
N1 C1 C2 107.7(3) . . ?
H2 C1 H1 108.5 . . ?
C2 C1 H2 110.2 . . ?
C2 C1 H1 110.2 . . ?
N1 C4 H7 109.6 . . ?
N1 C4 H8 109.6 . . ?
N1 C4 C3 110.3(3) . . ?
H7 C4 H8 108.1 . . ?
C3 C4 H7 109.6 . . ?
C3 C4 H8 109.6 . . ?
O1 C2 C1 111.7(3) . . ?
O1 C2 H3 105(2) . . ?
O1 C2 H4 111(2) . . ?
C1 C2 H3 111(2) . . ?
C1 C2 H4 104(2) . . ?
H3 C2 H4 114(3) . . ?
C20 C21 H23 119.4 . . ?
C20 C21 C22 121.3(4) . . ?
C22 C21 H23 119.4 . . ?
C11 C12A H13A 109.3 . . ?
C11 C12A H12A 109.3 . . ?
H13A C12A H12A 107.9 . . ?
C13A C12A C11 111.8(7) . . ?
C13A C12A H13A 109.3 . . ?
C13A C12A H12A 109.3 . . ?
O1 C3 C4 111.9(3) . . ?
O1 C3 H6 109.2 . . ?
O1 C3 H5 109.2 . . ?
C4 C3 H6 109.2 . . ?
C4 C3 H5 109.2 . . ?
H6 C3 H5 107.9 . . ?
C20 C25 H27 119.7 . . ?
C20 C25 C24 120.6(4) . . ?
C24 C25 H27 119.7 . . ?
C21 C22 H24 120.1 . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H24 120.1 . . ?
C22 C23 H25 119.9 . . ?
C22 C23 C24 120.2(5) . . ?
C24 C23 H25 119.9 . . ?
C25 C24 H26 120.0 . . ?
C23 C24 C25 120.1(5) . . ?
C23 C24 H26 120.0 . . ?
C12A C13A H14A 109.7 . . ?
C12A C13A H15A 109.7 . . ?
C12A C13A C14A 109.6(7) . . ?
H14A C13A H15A 108.2 . . ?
C14A C13A H14A 109.7 . . ?
C14A C13A H15A 109.7 . . ?
C13A C14A H16A 109.5 . . ?
C13A C14A H17A 109.5 . . ?
C13A C14A H18A 109.5 . . ?
H16A C14A H17A 109.5 . . ?
H16A C14A H18A 109.5 . . ?
H17A C14A H18A 109.5 . . ?
C11 C12 H12 104.9 . . ?
C11 C12 H13 104.9 . . ?
H12 C12 H13 105.8 . . ?
C13 C12 C11 129.5(17) . . ?
C13 C12 H12 104.9 . . ?
C13 C12 H13 104.9 . . ?
C12 C13 H15 107.5 . . ?
C12 C13 H14 107.5 . . ?
H15 C13 H14 107.0 . . ?
C14 C13 C12 119(3) . . ?
C14 C13 H15 107.5 . . ?
C14 C13 H14 107.5 . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H17 109.5 . . ?
C13 C14 H18 109.5 . . ?
H16 C14 H17 109.5 . . ?
H16 C14 H18 109.5 . . ?
H17 C14 H18 109.5 . . ?

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
F2 C10 C5 N1 -6.0(3) . . . . ?
F2 C10 C5 C6 175.0(2) . . . . ?
F1 C6 C7 C8 -174.9(2) . . . . ?
N2 C9 C10 F2 5.1(4) . . . . ?
N2 C9 C10 C5 -173.2(2) . . . . ?
N2 C9 C8 C17 0.6(4) . . . . ?
N2 C9 C8 C7 179.0(2) . . . . ?
N2 C11 C12A C13A -166.7(5) . . . . ?
N2 C11 C12 C13 -179(2) . . . . ?
N1 C5 C6 F1 1.1(4) . . . . ?
N1 C5 C6 C7 -176.5(3) . . . . ?
N1 C1 C2 O1 -61.5(4) . . . . ?
N1 C4 C3 O1 55.2(4) . . . . ?
N3 C19 C20 C21 -152.3(3) . . . . ?
N3 C19 C20 C25 27.6(5) . . . . ?
C9 N2 C15 C16 2.6(4) . . . . ?
C9 N2 C11 C12A 74.1(5) . . . . ?
C9 N2 C11 C12 85.0(11) . . . . ?
C9 C10 C5 N1 172.4(2) . . . . ?
C9 C10 C5 C6 -6.6(4) . . . . ?
C9 C8 C17 O2 -179.8(3) . . . . ?
C9 C8 C17 C16 0.5(4) . . . . ?
C9 C8 C7 C6 -4.3(4) . . . . ?
C10 C9 C8 C17 -177.9(2) . . . . ?
C10 C9 C8 C7 0.5(4) . . . . ?
C10 C5 C6 F1 -179.9(2) . . . . ?
C10 C5 C6 C7 2.5(4) . . . . ?
C8 C9 C10 F2 -176.5(2) . . . . ?
C8 C9 C10 C5 5.2(4) . . . . ?
C15 N2 C9 C10 176.3(2) . . . . ?
C15 N2 C9 C8 -2.1(3) . . . . ?
C15 N2 C11 C12A -99.1(5) . . . . ?
C15 N2 C11 C12 -88.2(11) . . . . ?
C15 C16 C17 O2 -179.8(3) . . . . ?
C15 C16 C17 C8 -0.2(4) . . . . ?
C15 C16 C18 O3 -2.3(4) . . . . ?
C15 C16 C18 N3 177.4(2) . . . . ?
C5 N1 C1 C2 -165.1(2) . . . . ?
C5 N1 C4 C3 165.5(3) . . . . ?
C5 C6 C7 C8 2.7(4) . . . . ?
C17 C8 C7 C6 174.2(3) . . . . ?
C17 C16 C15 N2 -1.4(4) . . . . ?
C17 C16 C18 O3 178.7(3) . . . . ?
C17 C16 C18 N3 -1.6(4) . . . . ?
C18 N3 C19 C20 -110.0(3) . . . . ?
C18 C16 C15 N2 179.6(2) . . . . ?
C18 C16 C17 O2 -0.9(5) . . . . ?
C18 C16 C17 C8 178.8(2) . . . . ?
C7 C8 C17 O2 1.7(4) . . . . ?
C7 C8 C17 C16 -178.0(2) . . . . ?
C11 N2 C9 C10 3.1(4) . . . . ?
C11 N2 C9 C8 -175.3(3) . . . . ?
C11 N2 C15 C16 176.1(3) . . . . ?
C11 C12A C13A C14A -173.7(6) . . . . ?
C11 C12 C13 C14 -175(2) . . . . ?
C19 N3 C18 O3 0.1(5) . . . . ?
C19 N3 C18 C16 -179.7(3) . . . . ?
C19 C20 C21 C22 -179.2(3) . . . . ?
C19 C20 C25 C24 179.4(4) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C20 C25 C24 C23 -0.2(8) . . . . ?
C1 N1 C5 C10 158.7(2) . . . . ?
C1 N1 C5 C6 -22.4(4) . . . . ?
C1 N1 C4 C3 -56.5(4) . . . . ?
C4 N1 C5 C10 -67.5(3) . . . . ?
C4 N1 C5 C6 111.4(3) . . . . ?
C4 N1 C1 C2 58.6(3) . . . . ?
C2 O1 C3 C4 -56.4(4) . . . . ?
C21 C20 C25 C24 -0.7(6) . . . . ?
C21 C22 C23 C24 -0.6(8) . . . . ?
C3 O1 C2 C1 60.2(4) . . . . ?
C25 C20 C21 C22 0.9(5) . . . . ?
C22 C23 C24 C25 0.8(8) . . . . ?

_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_P21_c_140K
_database_code_depnum_ccdc_archive 'CCDC 2386808'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2144(7)
_cell_length_b                   14.5808(10)
_cell_length_c                   24.8197(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.020(2)
_cell_angle_gamma                90
_cell_volume                     4409.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9525
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7820
_exptl_absorpt_correction_T_min  0.7520
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            63957
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.158
_diffrn_ambient_temperature      140(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   xray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6181
_reflns_number_total             9044
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9044
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.080
_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)+(0.0940P)²+5.3752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.2152
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F2A F 0.92684(11) 0.32476(10) 0.40628(5) 0.0301(3) Uani 1 1 d . . . . .
F1 F 0.39693(11) 0.43726(10) 0.22377(5) 0.0317(3) Uani 1 1 d . . . . .
F2 F 0.41378(11) 0.32498(10) 0.40161(5) 0.0318(3) Uani 1 1 d . . . . .
F1A F 0.90614(12) 0.42945(11) 0.22669(5) 0.0351(4) Uani 1 1 d . . . . .
O3A O 0.44852(15) 0.56948(13) 0.45025(7) 0.0366(4) Uani 1 1 d . . . . .
O3 O -0.05324(14) 0.57845(13) 0.45104(7) 0.0344(4) Uani 1 1 d . . . . .
O2 O 0.09118(15) 0.59364(14) 0.30175(7) 0.0390(5) Uani 1 1 d . . . . .
O1 O 0.63183(14) 0.17273(12) 0.26922(8) 0.0360(4) Uani 1 1 d . . . . .
O2A O 0.59858(16) 0.58565(14) 0.30264(7) 0.0419(5) Uani 1 1 d . . . . .
N2A N 0.73006(15) 0.42421(12) 0.42674(7) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.22182(15) 0.42837(12) 0.42372(7) 0.0215(4) Uani 1 1 d . . . . .
O1A O 1.13448(15) 0.16099(13) 0.27468(9) 0.0445(5) Uani 1 1 d . . . . .
N1 N 0.49234(15) 0.31299(13) 0.30483(7) 0.0243(4) Uani 1 1 d . . . . .
N3A N 0.44090(16) 0.63219(13) 0.36657(8) 0.0273(4) Uani 1 1 d . . . . .
H20A H 0.471110 0.634165 0.335423 0.033 Uiso 1 1 calc R U . . .
N1A N 0.99944(15) 0.30550(14) 0.30852(8) 0.0265(4) Uani 1 1 d . . . . .
N3 N -0.06291(16) 0.64179(14) 0.36740(8) 0.0282(4) Uani 1 1 d . . . . .
H20 H -0.035022 0.642815 0.335661 0.034 Uiso 1 1 calc R U . . .
C9 C 0.27101(17) 0.43125(14) 0.37454(8) 0.0212(4) Uani 1 1 d . . . . .
C8 C 0.22600(17) 0.48789(15) 0.33313(8) 0.0215(4) Uani 1 1 d . . . . .
C15 C 0.13006(17) 0.47778(15) 0.42947(9) 0.0215(4) Uani 1 1 d . . . . .
H19 H 0.096554 0.472656 0.462739 0.026 Uiso 1 1 calc R U . . .
C9A C 0.78092(18) 0.42662(15) 0.37785(9) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.40743(17) 0.37570(15) 0.31267(9) 0.0220(4) Uani 1 1 d . . . . .
C18A C 0.48643(18) 0.57799(15) 0.40576(9) 0.0243(5) Uani 1 1 d . . . . .
C16 C 0.08137(18) 0.53494(15) 0.39090(9) 0.0223(4) Uani 1 1 d . . . . .
C8A C 0.73527(18) 0.48240(15) 0.33584(9) 0.0245(5) Uani 1 1 d . . . . .
C5A C 0.91638(17) 0.36982(15) 0.31612(9) 0.0238(5) Uani 1 1 d . . . . .
C10 C 0.36390(18) 0.37891(15) 0.36292(9) 0.0224(4) Uani 1 1 d . . . . .
C10A C 0.87402(18) 0.37505(15) 0.36666(9) 0.0233(5) Uani 1 1 d . . . . .
C15A C 0.63708(18) 0.47303(15) 0.43137(9) 0.0231(5) Uani 1 1 d . . . . .
H19A H 0.602895 0.468455 0.464483 0.028 Uiso 1 1 calc R U . . .
C18 C -0.01725(18) 0.58617(16) 0.40598(9) 0.0246(5) Uani 1 1 d . . . . .
C6 C 0.35955(18) 0.43620(15) 0.27384(9) 0.0238(5) Uani 1 1 d . . . . .
C11A C 0.77293(19) 0.37050(15) 0.47448(9) 0.0251(5) Uani 1 1 d . . . . .
H11A H 0.740592 0.395461 0.506887 0.030 Uiso 1 1 calc R U . . .
H10A H 0.853311 0.379766 0.479310 0.030 Uiso 1 1 calc R U . . .
C16A C 0.58817(18) 0.52850(15) 0.39222(9) 0.0237(5) Uani 1 1 d . . . . .
C11 C 0.26077(19) 0.36902(16) 0.46941(9) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.230902 0.391948 0.502941 0.031 Uiso 1 1 calc R U . . .
H11 H 0.341832 0.372257 0.474188 0.031 Uiso 1 1 calc R U . . .
C17 C 0.12835(18) 0.54378(16) 0.33967(9) 0.0245(5) Uani 1 1 d . . . . .
C17A C 0.63608(19) 0.53701(16) 0.34094(9) 0.0264(5) Uani 1 1 d . . . . .
C7A C 0.78273(19) 0.48569(16) 0.28592(9) 0.0270(5) Uani 1 1 d . . . . .
H9A H 0.754948 0.526897 0.258631 0.032 Uiso 1 1 calc R U . . .
C6A C 0.86868(19) 0.42964(16) 0.27675(9) 0.0267(5) Uani 1 1 d . . . . .
C19A C 0.34443(19) 0.68746(16) 0.37326(10) 0.0273(5) Uani 1 1 d . . . . .
H22A H 0.309875 0.666670 0.406044 0.033 Uiso 1 1 calc R U . . .
H21A H 0.291078 0.677101 0.341959 0.033 Uiso 1 1 calc R U . . .
C7 C 0.27338(18) 0.49166(16) 0.28342(9) 0.0251(5) Uani 1 1 d . . . . .
H9 H 0.245306 0.533035 0.256289 0.030 Uiso 1 1 calc R U . . .
C1 C 0.56293(19) 0.32778(17) 0.25998(9) 0.0281(5) Uani 1 1 d . . . . .
H1 H 0.585492 0.392909 0.258621 0.034 Uiso 1 1 calc R U . . .
H2 H 0.522863 0.311841 0.225180 0.034 Uiso 1 1 calc R U . . .
C1A C 1.06761(19) 0.31634(18) 0.26250(10) 0.0312(5) Uani 1 1 d . . . . .
H1A H 1.091349 0.380945 0.259459 0.037 Uiso 1 1 calc R U . . .
H2A H 1.025592 0.298797 0.228503 0.037 Uiso 1 1 calc R U . . .
C20A C 0.36750(19) 0.78913(16) 0.37818(9) 0.0277(5) Uani 1 1 d . . . . .
C19 C -0.1562(2) 0.70009(17) 0.37604(10) 0.0314(5) Uani 1 1 d . . . . .
H21 H -0.192354 0.677741 0.408006 0.038 Uiso 1 1 calc R U . . .
H22 H -0.209867 0.695310 0.344372 0.038 Uiso 1 1 calc R U . . .
C2 C 0.66250(19) 0.26695(17) 0.26978(10) 0.0304(5) Uani 1 1 d . . . . .
H4 H 0.714062 0.278208 0.241446 0.036 Uiso 1 1 calc R U . . .
H3 H 0.700586 0.282265 0.305157 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4596(2) 0.21551(16) 0.30620(11) 0.0318(5) Uani 1 1 d . . . . .
H7 H 0.414860 0.199763 0.272678 0.038 Uiso 1 1 calc R U . . .
H8 H 0.414652 0.204608 0.337239 0.038 Uiso 1 1 calc R U . . .
C4A C 0.9645(2) 0.20901(17) 0.31221(11) 0.0327(6) Uani 1 1 d . . . . .
H7A H 0.918173 0.192089 0.279388 0.039 Uiso 1 1 calc R U . . .
H8A H 0.920429 0.200998 0.343870 0.039 Uiso 1 1 calc R U . . .
C21A C 0.2821(2) 0.85029(18) 0.36616(10) 0.0351(6) Uani 1 1 d . . . . .
H23A H 0.210789 0.827734 0.355700 0.042 Uiso 1 1 calc R U . . .
C12A C 0.7503(2) 0.26827(17) 0.47173(11) 0.0348(6) Uani 1 1 d . . . . .
H12A H 0.785663 0.242766 0.440322 0.042 Uiso 1 1 calc R U . . .
H13A H 0.785382 0.239223 0.504603 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2260(2) 0.26956(17) 0.46041(11) 0.0358(6) Uani 1 1 d . . . . .
H13 H 0.147066 0.263869 0.466562 0.043 Uiso 1 1 calc R U . . .
H12 H 0.235131 0.253107 0.422291 0.043 Uiso 1 1 calc R U . . .
C25A C 0.4711(2) 0.82291(19) 0.39293(11) 0.0370(6) Uani 1 1 d . . . . .
H27A H 0.530285 0.781793 0.401175 0.044 Uiso 1 1 calc R U . . .
C20 C -0.1251(2) 0.79982(18) 0.38462(11) 0.0365(6) Uani 1 1 d . . . . .
C2A C 1.16608(19) 0.25451(19) 0.27261(11) 0.0364(6) Uani 1 1 d . . . . .
H3A H 1.216393 0.263033 0.243435 0.044 Uiso 1 1 calc R U . . .
H4A H 1.206061 0.271737 0.307210 0.044 Uiso 1 1 calc R U . . .
C3 C 0.5610(2) 0.15581(18) 0.31132(12) 0.0388(6) Uani 1 1 d . . . . .
H6 H 0.601392 0.167567 0.346630 0.047 Uiso 1 1 calc R U . . .
H5 H 0.538691 0.090525 0.310343 0.047 Uiso 1 1 calc R U . . .
C13A C 0.6315(2) 0.24194(18) 0.46700(11) 0.0381(6) Uani 1 1 d . . . . .
H14A H 0.597158 0.264890 0.432277 0.046 Uiso 1 1 calc R U . . .
H15A H 0.593740 0.271220 0.496551 0.046 Uiso 1 1 calc R U . . .
C3A C 1.0643(2) 0.14753(19) 0.31775(13) 0.0437(7) Uani 1 1 d . . . . .
H6A H 1.105903 0.160275 0.352611 0.052 Uiso 1 1 calc R U . . .
H5A H 1.040262 0.082693 0.318012 0.052 Uiso 1 1 calc R U . . .
C22A C 0.3003(3) 0.94417(19) 0.36934(12) 0.0434(7) Uani 1 1 d . . . . .
H24A H 0.241450 0.985621 0.361213 0.052 Uiso 1 1 calc R U . . .
C23A C 0.4031(3) 0.9771(2) 0.38419(12) 0.0462(7) Uani 1 1 d . . . . .
H25A H 0.415418 1.041378 0.386561 0.055 Uiso 1 1 calc R U . . .
C24A C 0.4887(2) 0.9170(2) 0.39569(12) 0.0452(7) Uani 1 1 d . . . . .
H26A H 0.560014 0.940032 0.405549 0.054 Uiso 1 1 calc R U . . .
C21 C -0.1973(3) 0.8683(2) 0.36591(12) 0.0496(8) Uani 1 1 d . . . . .
H23 H -0.264849 0.851993 0.346991 0.060 Uiso 1 1 calc R U . . .
C13 C 0.2888(3) 0.2032(2) 0.49596(12) 0.0475(7) Uani 1 1 d . . . . .
H15 H 0.282330 0.220864 0.534126 0.057 Uiso 1 1 calc R U . . .
H14 H 0.367344 0.206491 0.488656 0.057 Uiso 1 1 calc R U . . .
C14A C 0.6166(3) 0.1379(2) 0.46983(13) 0.0480(7) Uani 1 1 d . . . . .
H16A H 0.654763 0.108655 0.440931 0.072 Uiso 1 1 calc R U . . .
H18A H 0.538236 0.122965 0.465448 0.072 Uiso 1 1 calc R U . . .
H17A H 0.647216 0.115385 0.504921 0.072 Uiso 1 1 calc R U . . .
C25 C -0.0271(3) 0.8248(2) 0.41255(16) 0.0569(9) Uani 1 1 d . . . . .
H27 H 0.022853 0.778716 0.425646 0.068 Uiso 1 1 calc R U . . .
C22 C -0.1719(4) 0.9602(2) 0.37461(15) 0.0664(11) Uani 1 1 d . . . . .
H24 H -0.221558 1.006437 0.361446 0.080 Uiso 1 1 calc R U . . .
C14 C 0.2487(4) 0.1046(2) 0.48769(15) 0.0716(12) Uani 1 1 d . . . . .
H18 H 0.170863 0.100973 0.494790 0.107 Uiso 1 1 calc R U . . .
H17 H 0.291351 0.063961 0.512586 0.107 Uiso 1 1 calc R U . . .
H16 H 0.258034 0.085783 0.450399 0.107 Uiso 1 1 calc R U . . .
C23 C -0.0746(4) 0.9841(2) 0.40230(19) 0.0778(14) Uani 1 1 d . . . . .
H25 H -0.057252 1.046936 0.408295 0.093 Uiso 1 1 calc R U . . .
C24 C -0.0016(3) 0.9167(3) 0.4215(2) 0.0786(13) Uani 1 1 d . . . . .
H26 H 0.065440 0.933312 0.440746 0.094 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2A C10A 1.353(3) . ?
F1 C6 1.354(2) . ?
F2 C10 1.353(3) . ?
F1A C6A 1.354(2) . ?
O3A C18A 1.233(3) . ?
O3 C18 1.235(3) . ?
O2 C17 1.249(3) . ?
O1 C2 1.424(3) . ?
O1 C3 1.424(3) . ?
O2A C17A 1.247(3) . ?
N2A C9A 1.402(3) . ?
N2A C15A 1.352(3) . ?
N2A C11A 1.485(3) . ?
N2 C9 1.398(3) . ?
N2 C15 1.348(3) . ?
N2 C11 1.478(3) . ?
O1A C2A 1.419(3) . ?
O1A C3A 1.430(3) . ?
N1 C5 1.406(3) . ?
N1 C1 1.471(3) . ?
N1 C4 1.478(3) . ?
N3A C18A 1.343(3) . ?
N3A C19A 1.447(3) . ?
N1A C5A 1.404(3) . ?
N1A C1A 1.468(3) . ?
N1A C4A 1.475(3) . ?
N3 C18 1.346(3) . ?
N3 C19 1.449(3) . ?
C9 C8 1.400(3) . ?
C9 C10 1.414(3) . ?
C8 C17 1.463(3) . ?
C8 C7 1.400(3) . ?
C15 C16 1.373(3) . ?
C9A C8A 1.406(3) . ?
C9A C10A 1.407(3) . ?
C5 C10 1.390(3) . ?
C5 C6 1.404(3) . ?
C18A C16A 1.495(3) . ?
C16 C18 1.487(3) . ?
C16 C17 1.437(3) . ?
C8A C17A 1.463(3) . ?
C8A C7A 1.405(3) . ?
C5A C10A 1.392(3) . ?
C5A C6A 1.405(3) . ?
C15A C16A 1.369(3) . ?
C6 C7 1.361(3) . ?
C11A C12A 1.517(3) . ?
C16A C17A 1.443(3) . ?
C11 C12 1.523(3) . ?
C7A C6A 1.362(3) . ?
C19A C20A 1.512(3) . ?
C1 C2 1.511(3) . ?
C1A C2A 1.510(4) . ?
C20A C21A 1.389(3) . ?
C20A C25A 1.383(4) . ?
C19 C20 1.514(4) . ?
C4 C3 1.512(3) . ?
C4A C3A 1.511(4) . ?
C21A C22A 1.388(4) . ?
C12A C13A 1.497(4) . ?
C12 C13 1.486(4) . ?
C25A C24A 1.390(4) . ?
C20 C21 1.390(4) . ?
C20 C25 1.388(4) . ?
C13A C14A 1.530(4) . ?
C22A C23A 1.371(4) . ?
C23A C24A 1.378(4) . ?
C21 C22 1.389(5) . ?
C13 C14 1.528(5) . ?
C25 C24 1.390(5) . ?
C22 C23 1.375(6) . ?
C23 C24 1.389(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.45(18) . . ?
C9A N2A C11A 123.44(18) . . ?
C15A N2A C9A 119.09(19) . . ?
C15A N2A C11A 117.48(18) . . ?
C9 N2 C11 123.52(18) . . ?
C15 N2 C9 119.18(18) . . ?
C15 N2 C11 117.19(18) . . ?
C2A O1A C3A 109.74(19) . . ?
C5 N1 C1 119.11(19) . . ?
C5 N1 C4 114.77(18) . . ?
C1 N1 C4 109.40(18) . . ?
C18A N3A C19A 122.93(19) . . ?
C5A N1A C1A 119.2(2) . . ?
C5A N1A C4A 114.44(18) . . ?
C1A N1A C4A 109.47(18) . . ?
C18 N3 C19 122.62(19) . . ?
N2 C9 C8 119.18(19) . . ?
N2 C9 C10 124.2(2) . . ?
C8 C9 C10 116.62(19) . . ?
C9 C8 C17 121.90(19) . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 C17 117.8(2) . . ?
N2 C15 C16 125.0(2) . . ?
N2A C9A C8A 118.65(19) . . ?
N2A C9A C10A 124.8(2) . . ?
C8A C9A C10A 116.53(19) . . ?
C10 C5 N1 118.6(2) . . ?
C10 C5 C6 115.31(19) . . ?
C6 C5 N1 126.12(19) . . ?
O3A C18A N3A 123.0(2) . . ?
O3A C18A C16A 121.5(2) . . ?
N3A C18A C16A 115.42(19) . . ?
C15 C16 C18 116.64(19) . . ?
C15 C16 C17 119.4(2) . . ?
C17 C16 C18 123.9(2) . . ?
C9A C8A C17A 122.6(2) . . ?
C7A C8A C9A 120.5(2) . . ?
C7A C8A C17A 116.9(2) . . ?
N1A C5A C6A 126.1(2) . . ?
C10A C5A N1A 118.4(2) . . ?
C10A C5A C6A 115.5(2) . . ?
F2 C10 C9 119.80(18) . . ?
F2 C10 C5 115.83(19) . . ?
C5 C10 C9 124.3(2) . . ?
F2A C10A C9A 119.79(19) . . ?
F2A C10A C5A 115.88(19) . . ?
C5A C10A C9A 124.3(2) . . ?
N2A C15A C16A 125.3(2) . . ?
O3 C18 N3 122.9(2) . . ?
O3 C18 C16 121.9(2) . . ?
N3 C18 C16 115.23(19) . . ?
F1 C6 C5 119.10(19) . . ?
F1 C6 C7 117.9(2) . . ?
C7 C6 C5 122.9(2) . . ?
N2A C11A C12A 115.43(19) . . ?
C15A C16A C18A 116.98(19) . . ?
C15A C16A C17A 119.5(2) . . ?
C17A C16A C18A 123.5(2) . . ?
N2 C11 C12 111.93(19) . . ?
O2 C17 C8 119.8(2) . . ?
O2 C17 C16 124.9(2) . . ?
C16 C17 C8 115.30(19) . . ?
O2A C17A C8A 120.4(2) . . ?
O2A C17A C16A 124.8(2) . . ?
C16A C17A C8A 114.8(2) . . ?
C6A C7A C8A 119.8(2) . . ?
F1A C6A C5A 119.1(2) . . ?
F1A C6A C7A 117.9(2) . . ?
C7A C6A C5A 122.9(2) . . ?
N3A C19A C20A 114.0(2) . . ?
C6 C7 C8 120.2(2) . . ?
N1 C1 C2 107.45(19) . . ?
N1A C1A C2A 107.2(2) . . ?
C21A C20A C19A 118.6(2) . . ?
C25A C20A C19A 122.2(2) . . ?
C25A C20A C21A 119.2(2) . . ?
N3 C19 C20 113.1(2) . . ?
O1 C2 C1 110.89(19) . . ?
N1 C4 C3 109.6(2) . . ?
N1A C4A C3A 109.7(2) . . ?
C22A C21A C20A 120.4(3) . . ?
C13A C12A C11A 115.4(2) . . ?
C13 C12 C11 113.9(2) . . ?
C20A C25A C24A 120.0(3) . . ?
C21 C20 C19 119.7(3) . . ?
C25 C20 C19 121.4(2) . . ?
C25 C20 C21 118.9(3) . . ?
O1A C2A C1A 111.4(2) . . ?
O1 C3 C4 112.0(2) . . ?
C12A C13A C14A 111.6(2) . . ?
O1A C3A C4A 111.9(2) . . ?
C23A C22A C21A 120.1(3) . . ?
C22A C23A C24A 120.0(3) . . ?
C23A C24A C25A 120.4(3) . . ?
C22 C21 C20 120.7(4) . . ?
C12 C13 C14 112.7(3) . . ?
C20 C25 C24 120.6(3) . . ?
C23 C22 C21 119.9(3) . . ?
C22 C23 C24 120.2(4) . . ?
C23 C24 C25 119.7(4) . . ?

####################################################################### 
# 
# 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_P-1_160K
_database_code_depnum_ccdc_archive 'CCDC 2386809'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-02-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   5.35040(10)
_cell_length_b                   13.6627(4)
_cell_length_c                   15.4350(4)
_cell_angle_alpha                95.0210(10)
_cell_angle_beta                 92.0420(10)
_cell_angle_gamma                100.4030(10)
_cell_volume                     1103.98(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7684
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0826 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.9369.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18289
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.113
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3402
_reflns_number_total             4500
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     98
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.012
_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)+(0.0001P)²+1.5875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1292
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C00K-C00T \\sim C00K-C1
 with sigma of 0.02
 C00K-C00W \\sim C00K-C4
 with sigma of 0.02
 C00R-C00V \\sim C2-C3
 with sigma of 0.02
 C00R-C00X \\sim C2-C00Y
 with sigma of 0.02
 C00T-C00X \\sim C1-C00Y
 with sigma of 0.02
 C00V-C00W \\sim C3-C4
 with sigma of 0.02
 C00K-C00V \\sim C00K-C3
 with sigma of 0.04
 C00K-C00X \\sim C00K-C00Y
 with sigma of 0.04
 C00R-C00T \\sim C2-C1
 with sigma of 0.04
 C00R-C00W \\sim C2-C4
 with sigma of 0.04
 C00V-C00X \\sim C3-C00Y
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C00K: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
2A
4. Rigid body (RIGU) restrains
 C00W, C00K, C00T, C00X, C00R, C00V, C00J
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00K, C1, C00Y, C2, C3, C4, C00J
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1)=Sof(H1)=Sof(C00Y)=Sof(H00)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=
 Sof(H4)=1-FVAR(1)
 Sof(C00R)=Sof(H00R)=Sof(C00T)=Sof(H00T)=Sof(C00V)=Sof(H00X)=Sof(C00W)=
 Sof(H00Y)=Sof(C00X)=Sof(H00Z)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C00J(H00A,H00B), C00L(H00C,H00D), C00M(H00E,H00G), C00N(H00I,H00J), C00O(H00K,
 H00L), C00P(H00M,H00N), C00Q(H00O,H00P), C00S(H00Q,H00S)
6.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00R(H00R), C00T(H00T), C00V(H00X), C00W(H00Y),
 C00X(H00Z), C1(H1), C00Y(H00), C2(H2), C3(H3), C4(H4)
6.c Idealised Me refined as rotating group:
 C00U(H00U,H00V,H00W)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F2 F 0.9898(3) 0.20703(10) 0.71069(10) 0.0506(4) Uani 1 1 d . . . . .
F1 F 1.0874(3) 0.54185(11) 0.65088(9) 0.0487(4) Uani 1 1 d . . . . .
O2 O 0.4050(3) 0.37059(13) 0.43809(10) 0.0437(4) Uani 1 1 d . . . . .
O3 O -0.0458(3) 0.08067(13) 0.40978(12) 0.0491(5) Uani 1 1 d . . . . .
O1 O 1.5823(4) 0.44457(14) 0.89709(12) 0.0531(5) Uani 1 1 d . . . . .
N2 N 0.5658(4) 0.15238(14) 0.58707(11) 0.0344(4) Uani 1 1 d . . . . .
N3 N 0.0028(4) 0.23880(16) 0.36923(12) 0.0387(5) Uani 1 1 d . . . . .
N1 N 1.2000(3) 0.40897(15) 0.76066(12) 0.0359(4) Uani 1 1 d . . . . .
C5 C 1.0362(4) 0.37530(17) 0.68640(14) 0.0327(5) Uani 1 1 d . . . . .
C8 C 0.6577(4) 0.32283(17) 0.54943(13) 0.0328(5) Uani 1 1 d . . . . .
C17 C 0.4468(4) 0.30273(17) 0.48297(13) 0.0342(5) Uani 1 1 d . . . . .
C9 C 0.7119(4) 0.24855(16) 0.60056(13) 0.0318(5) Uani 1 1 d . . . . .
C16 C 0.3009(4) 0.20301(17) 0.47596(13) 0.0340(5) Uani 1 1 d . . . . .
C10 C 0.9129(4) 0.27753(17) 0.66488(14) 0.0346(5) Uani 1 1 d . . . . .
C7 C 0.7960(4) 0.42087(18) 0.56396(14) 0.0375(5) Uani 1 1 d . . . . .
H9 H 0.765858 0.470057 0.527010 0.045 Uiso 1 1 calc R U . . .
C18 C 0.0704(4) 0.16842(17) 0.41547(14) 0.0363(5) Uani 1 1 d . . . . .
C15 C 0.3661(4) 0.13445(17) 0.52762(14) 0.0350(5) Uani 1 1 d . . . . .
H19 H 0.264168 0.069418 0.521474 0.042 Uiso 1 1 calc R U . . .
C6 C 0.9738(4) 0.44494(18) 0.63148(15) 0.0373(5) Uani 1 1 d . . . . .
C19 C -0.2138(4) 0.21953(18) 0.30610(14) 0.0390(5) Uani 1 1 d . . . . .
H22 H -0.316568 0.272477 0.316189 0.047 Uiso 1 1 calc R U . . .
H21 H -0.322482 0.154836 0.315042 0.047 Uiso 1 1 calc R U . . .
C20 C -0.1332(4) 0.21652(17) 0.21343(15) 0.0372(5) Uani 1 1 d D . . . .
C11 C 0.5863(5) 0.07306(17) 0.64516(15) 0.0390(5) Uani 1 1 d . . . . .
H11 H 0.767039 0.067085 0.653578 0.047 Uiso 1 1 calc R U . . .
H10 H 0.491175 0.008207 0.617662 0.047 Uiso 1 1 calc R U . . .
C4 C 1.1733(5) 0.35377(19) 0.83791(15) 0.0415(5) Uani 1 1 d . . . . .
H7 H 1.241919 0.291367 0.827828 0.050 Uiso 1 1 calc R U . . .
H8 H 0.991317 0.335803 0.850361 0.050 Uiso 1 1 calc R U . . .
C1 C 1.4679(4) 0.44414(18) 0.74355(15) 0.0395(5) Uani 1 1 d . . . . .
H1 H 1.478241 0.487658 0.695282 0.047 Uiso 1 1 calc R U . . .
H2 H 1.548109 0.386198 0.725654 0.047 Uiso 1 1 calc R U . . .
C12 C 0.4797(5) 0.09691(19) 0.73352(15) 0.0441(6) Uani 1 1 d . . . . .
H12 H 0.526135 0.169784 0.750114 0.053 Uiso 1 1 calc R U . . .
H13 H 0.291669 0.079332 0.727755 0.053 Uiso 1 1 calc R U . . .
C3 C 1.3184(5) 0.4193(2) 0.91417(16) 0.0500(6) Uani 1 1 d . . . . .
H5 H 1.247309 0.481098 0.924426 0.060 Uiso 1 1 calc R U . . .
H6 H 1.299490 0.383501 0.967314 0.060 Uiso 1 1 calc R U . . .
C2 C 1.6093(5) 0.5018(2) 0.82409(17) 0.0492(6) Uani 1 1 d . . . . .
H4 H 1.792018 0.520261 0.812853 0.059 Uiso 1 1 calc R U . . .
H3 H 1.542933 0.564201 0.837397 0.059 Uiso 1 1 calc R U . . .
C23 C -0.005(5) 0.2106(18) 0.0389(9) 0.062(4) Uani 0.471(17) 1 d D . P A 1
H25 H 0.040363 0.209101 -0.020105 0.074 Uiso 0.471(17) 1 calc R U P A 1
C13 C 0.5740(6) 0.0424(2) 0.80581(17) 0.0573(7) Uani 1 1 d . . . . .
H15 H 0.761613 0.061137 0.813461 0.069 Uiso 1 1 calc R U . . .
H14 H 0.529951 -0.030599 0.789689 0.069 Uiso 1 1 calc R U . . .
C21 C -0.282(2) 0.2508(9) 0.1496(5) 0.052(2) Uani 0.471(17) 1 d D . P A 1
H23 H -0.425951 0.278327 0.166141 0.062 Uiso 0.471(17) 1 calc R U P A 1
C14 C 0.4549(10) 0.0685(3) 0.8915(2) 0.1027(15) Uani 1 1 d . . . . .
H18 H 0.270000 0.046219 0.884985 0.154 Uiso 1 1 calc R U . . .
H16 H 0.494092 0.141018 0.906528 0.154 Uiso 1 1 calc R U . . .
H17 H 0.524358 0.034998 0.937914 0.154 Uiso 1 1 calc R U . . .
C24 C 0.1475(19) 0.1781(11) 0.1008(5) 0.062(2) Uani 0.471(17) 1 d D . P A 1
H26 H 0.292961 0.151666 0.084046 0.074 Uiso 0.471(17) 1 calc R U P A 1
C25 C 0.0860(16) 0.1844(10) 0.1874(4) 0.051(2) Uani 0.471(17) 1 d D . P A 1
H27 H 0.197268 0.166181 0.229975 0.062 Uiso 0.471(17) 1 calc R U P A 1
C22 C -0.220(3) 0.2449(10) 0.0626(5) 0.068(3) Uani 0.471(17) 1 d D . P A 1
H24 H -0.327797 0.264648 0.019645 0.082 Uiso 0.471(17) 1 calc R U P A 1
C21A C -0.1865(18) 0.2828(6) 0.1601(5) 0.0412(16) Uani 0.529(17) 1 d D . P A 2
H23A H -0.276816 0.333124 0.181027 0.049 Uiso 0.529(17) 1 calc R U P A 2
C22A C -0.1119(19) 0.2795(6) 0.0742(5) 0.0493(19) Uani 0.529(17) 1 d D . P A 2
H24A H -0.146553 0.328505 0.037687 0.059 Uiso 0.529(17) 1 calc R U P A 2
C23A C 0.013(4) 0.2043(17) 0.0426(8) 0.055(4) Uani 0.529(17) 1 d D . P A 2
H25A H 0.061507 0.200732 -0.016065 0.066 Uiso 0.529(17) 1 calc R U P A 2
C24A C 0.066(2) 0.1354(8) 0.0963(5) 0.059(2) Uani 0.529(17) 1 d D . P A 2
H26A H 0.153970 0.084494 0.075236 0.071 Uiso 0.529(17) 1 calc R U P A 2
C25A C -0.010(2) 0.1396(8) 0.1811(4) 0.052(2) Uani 0.529(17) 1 d D . P A 2
H27A H 0.022608 0.090298 0.217677 0.063 Uiso 0.529(17) 1 calc R U P A 2
H20 H 0.102(6) 0.301(2) 0.379(2) 0.068(10) Uiso 1 1 d . . . . .


_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
F2 C10 1.356(3) . ?
F1 C6 1.356(3) . ?
O2 C17 1.251(3) . ?
O3 C18 1.241(3) . ?
O1 C3 1.432(3) . ?
O1 C2 1.423(3) . ?
N2 C9 1.396(3) . ?
N2 C15 1.357(3) . ?
N2 C11 1.482(3) . ?
N3 C18 1.339(3) . ?
N3 C19 1.458(3) . ?
N3 H20 0.91(3) . ?
N1 C5 1.409(3) . ?
N1 C4 1.463(3) . ?
N1 C1 1.468(3) . ?
C5 C10 1.385(3) . ?
C5 C6 1.404(3) . ?
C8 C17 1.468(3) . ?
C8 C9 1.403(3) . ?
C8 C7 1.404(3) . ?
C17 C16 1.436(3) . ?
C9 C10 1.414(3) . ?
C16 C18 1.499(3) . ?
C16 C15 1.365(3) . ?
C7 H9 0.9500 . ?
C7 C6 1.362(3) . ?
C15 H19 0.9500 . ?
C19 H22 0.9900 . ?
C19 H21 0.9900 . ?
C19 C20 1.508(3) . ?
C20 C21 1.407(7) . ?
C20 C25 1.385(7) . ?
C20 C21A 1.336(6) . ?
C20 C25A 1.405(6) . ?
C11 H11 0.9900 . ?
C11 H10 0.9900 . ?
C11 C12 1.529(3) . ?
C4 H7 0.9900 . ?
C4 H8 0.9900 . ?
C4 C3 1.513(3) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C1 C2 1.511(3) . ?
C12 H12 0.9900 . ?
C12 H13 0.9900 . ?
C12 C13 1.515(3) . ?
C3 H5 0.9900 . ?
C3 H6 0.9900 . ?
C2 H4 0.9900 . ?
C2 H3 0.9900 . ?
C23 H25 0.9500 . ?
C23 C24 1.388(13) . ?
C23 C22 1.370(14) . ?
C13 H15 0.9900 . ?
C13 H14 0.9900 . ?
C13 C14 1.531(5) . ?
C21 H23 0.9500 . ?
C21 C22 1.394(9) . ?
C14 H18 0.9800 . ?
C14 H16 0.9800 . ?
C14 H17 0.9800 . ?
C24 H26 0.9500 . ?
C24 C25 1.386(9) . ?
C25 H27 0.9500 . ?
C22 H24 0.9500 . ?
C21A H23A 0.9500 . ?
C21A C22A 1.398(7) . ?
C22A H24A 0.9500 . ?
C22A C23A 1.387(12) . ?
C23A H25A 0.9500 . ?
C23A C24A 1.367(11) . ?
C24A H26A 0.9500 . ?
C24A C25A 1.383(8) . ?
C25A H27A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.28(19) . . ?
C9 N2 C11 123.22(17) . . ?
C15 N2 C9 118.94(19) . . ?
C15 N2 C11 116.87(19) . . ?
C18 N3 C19 123.2(2) . . ?
C18 N3 H20 116.0(19) . . ?
C19 N3 H20 120.8(19) . . ?
C5 N1 C4 119.73(19) . . ?
C5 N1 C1 115.53(18) . . ?
C4 N1 C1 111.99(18) . . ?
C10 C5 N1 125.1(2) . . ?
C10 C5 C6 115.33(19) . . ?
C6 C5 N1 119.4(2) . . ?
C9 C8 C17 121.6(2) . . ?
C9 C8 C7 120.46(19) . . ?
C7 C8 C17 117.8(2) . . ?
O2 C17 C8 119.9(2) . . ?
O2 C17 C16 125.0(2) . . ?
C16 C17 C8 115.03(19) . . ?
N2 C9 C8 119.49(18) . . ?
N2 C9 C10 123.8(2) . . ?
C8 C9 C10 116.7(2) . . ?
C17 C16 C18 123.6(2) . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 C18 116.3(2) . . ?
F2 C10 C5 116.60(19) . . ?
F2 C10 C9 119.3(2) . . ?
C5 C10 C9 124.1(2) . . ?
C8 C7 H9 120.3 . . ?
C6 C7 C8 119.5(2) . . ?
C6 C7 H9 120.3 . . ?
O3 C18 N3 123.6(2) . . ?
O3 C18 C16 121.4(2) . . ?
N3 C18 C16 115.0(2) . . ?
N2 C15 C16 124.8(2) . . ?
N2 C15 H19 117.6 . . ?
C16 C15 H19 117.6 . . ?
F1 C6 C5 117.31(19) . . ?
F1 C6 C7 119.2(2) . . ?
C7 C6 C5 123.4(2) . . ?
N3 C19 H22 109.1 . . ?
N3 C19 H21 109.1 . . ?
N3 C19 C20 112.36(19) . . ?
H22 C19 H21 107.9 . . ?
C20 C19 H22 109.1 . . ?
C20 C19 H21 109.1 . . ?
C21 C20 C19 119.1(4) . . ?
C25 C20 C19 123.4(4) . . ?
C25 C20 C21 117.4(5) . . ?
C21A C20 C19 121.5(3) . . ?
C21A C20 C25A 119.2(4) . . ?
C25A C20 C19 119.3(3) . . ?
N2 C11 H11 109.5 . . ?
N2 C11 H10 109.5 . . ?
N2 C11 C12 110.83(18) . . ?
H11 C11 H10 108.1 . . ?
C12 C11 H11 109.5 . . ?
C12 C11 H10 109.5 . . ?
N1 C4 H7 110.0 . . ?
N1 C4 H8 110.0 . . ?
N1 C4 C3 108.5(2) . . ?
H7 C4 H8 108.4 . . ?
C3 C4 H7 110.0 . . ?
C3 C4 H8 110.0 . . ?
N1 C1 H1 109.6 . . ?
N1 C1 H2 109.6 . . ?
N1 C1 C2 110.4(2) . . ?
H1 C1 H2 108.1 . . ?
C2 C1 H1 109.6 . . ?
C2 C1 H2 109.6 . . ?
C11 C12 H12 108.8 . . ?
C11 C12 H13 108.8 . . ?
H12 C12 H13 107.7 . . ?
C13 C12 C11 113.9(2) . . ?
C13 C12 H12 108.8 . . ?
C13 C12 H13 108.8 . . ?
O1 C3 C4 110.3(2) . . ?
O1 C3 H5 109.6 . . ?
O1 C3 H6 109.6 . . ?
C4 C3 H5 109.6 . . ?
C4 C3 H6 109.6 . . ?
H5 C3 H6 108.1 . . ?
O1 C2 C1 111.5(2) . . ?
O1 C2 H4 109.3 . . ?
O1 C2 H3 109.3 . . ?
C1 C2 H4 109.3 . . ?
C1 C2 H3 109.3 . . ?
H4 C2 H3 108.0 . . ?
C24 C23 H25 119.9 . . ?
C22 C23 H25 119.9 . . ?
C22 C23 C24 120.2(11) . . ?
C12 C13 H15 109.5 . . ?
C12 C13 H14 109.5 . . ?
C12 C13 C14 110.8(2) . . ?
H15 C13 H14 108.1 . . ?
C14 C13 H15 109.5 . . ?
C14 C13 H14 109.5 . . ?
C20 C21 H23 119.6 . . ?
C22 C21 C20 120.8(7) . . ?
C22 C21 H23 119.6 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H17 109.5 . . ?
H18 C14 H16 109.5 . . ?
H18 C14 H17 109.5 . . ?
H16 C14 H17 109.5 . . ?
C23 C24 H26 120.2 . . ?
C25 C24 C23 119.6(9) . . ?
C25 C24 H26 120.2 . . ?
C20 C25 C24 121.8(7) . . ?
C20 C25 H27 119.1 . . ?
C24 C25 H27 119.1 . . ?
C23 C22 C21 120.0(9) . . ?
C23 C22 H24 120.0 . . ?
C21 C22 H24 120.0 . . ?
C20 C21A H23A 119.4 . . ?
C20 C21A C22A 121.3(6) . . ?
C22A C21A H23A 119.4 . . ?
C21A C22A H24A 120.2 . . ?
C23A C22A C21A 119.6(7) . . ?
C23A C22A H24A 120.2 . . ?
C22A C23A H25A 120.2 . . ?
C24A C23A C22A 119.6(8) . . ?
C24A C23A H25A 120.2 . . ?
C23A C24A H26A 119.9 . . ?
C23A C24A C25A 120.1(7) . . ?
C25A C24A H26A 119.9 . . ?
C20 C25A H27A 119.9 . . ?
C24A C25A C20 120.2(5) . . ?
C24A C25A H27A 119.9 . . ?

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
O2 C17 C16 C18 -2.5(4) . . . . ?
O2 C17 C16 C15 179.1(2) . . . . ?
N2 C9 C10 F2 7.4(3) . . . . ?
N2 C9 C10 C5 -171.1(2) . . . . ?
N2 C11 C12 C13 -159.5(2) . . . . ?
N3 C19 C20 C21 -146.8(7) . . . . ?
N3 C19 C20 C25 31.1(8) . . . . ?
N3 C19 C20 C21A -117.0(6) . . . . ?
N3 C19 C20 C25A 66.0(7) . . . . ?
N1 C5 C10 F2 -11.7(3) . . . . ?
N1 C5 C10 C9 166.8(2) . . . . ?
N1 C5 C6 F1 3.4(3) . . . . ?
N1 C5 C6 C7 -172.5(2) . . . . ?
N1 C4 C3 O1 -60.3(3) . . . . ?
N1 C1 C2 O1 54.6(3) . . . . ?
C5 N1 C4 C3 -164.9(2) . . . . ?
C5 N1 C1 C2 165.6(2) . . . . ?
C8 C17 C16 C18 176.92(19) . . . . ?
C8 C17 C16 C15 -1.5(3) . . . . ?
C8 C9 C10 F2 -173.82(19) . . . . ?
C8 C9 C10 C5 7.7(3) . . . . ?
C8 C7 C6 F1 -173.0(2) . . . . ?
C8 C7 C6 C5 2.8(4) . . . . ?
C17 C8 C9 N2 1.3(3) . . . . ?
C17 C8 C9 C10 -177.5(2) . . . . ?
C17 C8 C7 C6 172.7(2) . . . . ?
C17 C16 C18 O3 177.9(2) . . . . ?
C17 C16 C18 N3 -2.0(3) . . . . ?
C17 C16 C15 N2 -0.5(3) . . . . ?
C9 N2 C15 C16 3.0(3) . . . . ?
C9 N2 C11 C12 69.8(3) . . . . ?
C9 C8 C17 O2 -179.5(2) . . . . ?
C9 C8 C17 C16 1.0(3) . . . . ?
C9 C8 C7 C6 -3.8(3) . . . . ?
C10 C5 C6 F1 179.07(19) . . . . ?
C10 C5 C6 C7 3.1(3) . . . . ?
C7 C8 C17 O2 4.0(3) . . . . ?
C7 C8 C17 C16 -175.4(2) . . . . ?
C7 C8 C9 N2 177.7(2) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C18 N3 C19 C20 -106.3(3) . . . . ?
C18 C16 C15 N2 -179.0(2) . . . . ?
C15 N2 C9 C8 -3.3(3) . . . . ?
C15 N2 C9 C10 175.5(2) . . . . ?
C15 N2 C11 C12 -98.7(2) . . . . ?
C15 C16 C18 O3 -3.6(3) . . . . ?
C15 C16 C18 N3 176.4(2) . . . . ?
C6 C5 C10 F2 172.91(19) . . . . ?
C6 C5 C10 C9 -8.6(3) . . . . ?
C19 N3 C18 O3 -0.8(4) . . . . ?
C19 N3 C18 C16 179.2(2) . . . . ?
C19 C20 C21 C22 -177.0(6) . . . . ?
C19 C20 C25 C24 176.8(6) . . . . ?
C19 C20 C21A C22A -179.8(4) . . . . ?
C19 C20 C25A C24A 179.9(5) . . . . ?
C20 C21 C22 C23 -3.7(19) . . . . ?
C20 C21A C22A C23A 2.0(15) . . . . ?
C11 N2 C9 C8 -171.7(2) . . . . ?
C11 N2 C9 C10 7.1(3) . . . . ?
C11 N2 C15 C16 172.1(2) . . . . ?
C11 C12 C13 C14 -178.8(3) . . . . ?
C4 N1 C5 C10 -25.1(3) . . . . ?
C4 N1 C5 C6 150.0(2) . . . . ?
C4 N1 C1 C2 -52.6(3) . . . . ?
C1 N1 C5 C10 113.5(2) . . . . ?
C1 N1 C5 C6 -71.3(3) . . . . ?
C1 N1 C4 C3 55.2(3) . . . . ?
C3 O1 C2 C1 -60.0(3) . . . . ?
C2 O1 C3 C4 63.1(3) . . . . ?
C23 C24 C25 C20 4.2(18) . . . . ?
C21 C20 C25 C24 -5.2(9) . . . . ?
C24 C23 C22 C21 2(3) . . . . ?
C25 C20 C21 C22 5.0(9) . . . . ?
C22 C23 C24 C25 -3(3) . . . . ?
C21A C20 C25A C24A 2.8(9) . . . . ?
C21A C22A C23A C24A -1(3) . . . . ?
C22A C23A C24A C25A 1(3) . . . . ?
C23A C24A C25A C20 -2.0(17) . . . . ?
C25A C20 C21A C22A -2.8(8) . . . . ?

_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_p21_c_170k
_database_code_depnum_ccdc_archive 'CCDC 2386804'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2025-01-17
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2289(3)
_cell_length_b                   14.6129(4)
_cell_length_c                   24.8725(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.8930(10)
_cell_angle_gamma                90
_cell_volume                     4434.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7005
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            56343
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_min         2.153
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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                5310
_reflns_number_total             9088
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         9088
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.040
_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)+(0.0955P)²+6.1091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.2423
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C14A \\sim C13A \\sim C13B \\sim C14B: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
C14 \\sim C13 \\sim C27 \\sim C32: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
C29 \\sim C20 \\sim C25 \\sim C35 \\sim C24 \\sim C34 \\sim C23 \\sim C33 \\sim
C22 \\sim C31 \\sim C21 \\sim C30: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
3. Others
 Fixed Sof: C20(0.5) C21(0.5) H23(0.5) C25(0.5) H27(0.5) C22(0.5) H24(0.5)
 C23(0.5) H25(0.5) C24(0.5) H26(0.5) C13B(0.75) H14B(0.75) H15B(0.75)
 C14B(0.75) H17B(0.75) H16B(0.75) H18B(0.75) C27(0.7) H29(0.7) H28(0.7)
 C32(0.7) H40(0.7) H41(0.7) H42(0.7) C13A(0.25) H14A(0.25) H15A(0.25)
 C14A(0.25) H17A(0.25) H16A(0.25) H18A(0.25) C13(0.3) H14(0.3) H15(0.3)
 C14(0.3) H18(0.3) H17(0.3) H16(0.3) C35(0.5) H39(0.5) C34(0.5) H38(0.5)
 C33(0.5) H37(0.5) C31(0.5) H36(0.5) C30(0.5) H32(0.5) C29(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11,H10), C11A(H10A,H11A), C19A(H21A,H22A), C19(H22,H21), C1(H1,H2),
 C1A(H1A,H2A), C4(H7,H8), C2(H4,H3), C4A(H7A,H8A), C2A(H4A,H3A), C3A(H5A,H6A),
 C3(H5,H6), C12A(H13A,H12A), C12(H12,H13), C13B(H14B,H15B), C27(H29,H28),
 C13A(H14A,H15A), C13(H14,H15)
4.b Aromatic/amide H refined with riding coordinates:
 C15(H19), C15A(H19A), C7A(H9A), C7(H9), C21A(H23A), C25A(H27A), C21(H23),
 C22A(H24A), C23A(H25A), C24A(H26A), C25(H27), C24(H26), C35(H39), C34(H38),
 C33(H37), C31(H36), C30(H32)
4.c Idealised Me refined as rotating group:
 C14B(H17B,H16B,H18B), C32(H40,H41,H42), C14A(H17A,H16A,H18A), C14(H18,H17,H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F1 F 0.60124(13) 0.43647(12) 0.77550(6) 0.0417(4) Uani 1 1 d . . . . .
F2A F 0.07641(13) 0.32521(11) 0.59501(6) 0.0403(4) Uani 1 1 d . . . . .
F2 F 0.58464(13) 0.32526(11) 0.59795(6) 0.0410(4) Uani 1 1 d . . . . .
F1A F 0.09569(14) 0.43181(12) 0.77372(6) 0.0442(4) Uani 1 1 d . . . . .
O3 O 1.05267(16) 0.57714(15) 0.54923(8) 0.0449(5) Uani 1 1 d . . . . .
O3A O 0.55160(17) 0.57139(15) 0.54967(8) 0.0465(5) Uani 1 1 d . . . . .
O2 O 0.90681(17) 0.59250(16) 0.69772(8) 0.0499(6) Uani 1 1 d . . . . .
O1 O 0.36856(17) 0.17184(14) 0.73033(9) 0.0475(5) Uani 1 1 d . . . . .
N2 N 0.77694(17) 0.42807(14) 0.57593(8) 0.0283(5) Uani 1 1 d . . . . .
O2A O 0.40219(18) 0.58773(17) 0.69718(8) 0.0527(6) Uani 1 1 d . . . . .
N2A N 0.27165(17) 0.42529(14) 0.57399(8) 0.0294(5) Uani 1 1 d . . . . .
O1A O -0.13312(17) 0.16473(16) 0.72687(10) 0.0542(6) Uani 1 1 d . . . . .
N1 N 0.50686(17) 0.31229(15) 0.69475(9) 0.0326(5) Uani 1 1 d . . . . .
N3A N 0.55926(19) 0.63417(16) 0.63309(9) 0.0354(5) Uani 1 1 d . . . . .
N1A N 0.00243(18) 0.30750(16) 0.69240(9) 0.0347(5) Uani 1 1 d . . . . .
N3 N 1.06147(19) 0.64008(16) 0.63274(9) 0.0367(5) Uani 1 1 d . . . . .
C8 C 0.7723(2) 0.48741(17) 0.66632(10) 0.0286(5) Uani 1 1 d . . . . .
C9A C 0.2212(2) 0.42787(17) 0.62284(10) 0.0286(5) Uani 1 1 d . . . . .
C9 C 0.7277(2) 0.43092(17) 0.62502(10) 0.0280(5) Uani 1 1 d . . . . .
C15 C 0.8689(2) 0.47733(17) 0.57032(10) 0.0285(5) Uani 1 1 d . . . . .
H19 H 0.902672 0.472227 0.537170 0.034 Uiso 1 1 calc R U . . .
C16 C 0.9171(2) 0.53409(17) 0.60881(10) 0.0295(5) Uani 1 1 d . . . . .
C8A C 0.2663(2) 0.48385(18) 0.66457(10) 0.0311(6) Uani 1 1 d . . . . .
C5 C 0.5915(2) 0.37541(17) 0.68701(10) 0.0291(5) Uani 1 1 d . . . . .
C10A C 0.1281(2) 0.37628(17) 0.63427(10) 0.0306(6) Uani 1 1 d . . . . .
C5A C 0.0856(2) 0.37160(18) 0.68470(10) 0.0310(6) Uani 1 1 d . . . . .
C18A C 0.5140(2) 0.57985(18) 0.59419(10) 0.0324(6) Uani 1 1 d . . . . .
C10 C 0.6347(2) 0.37877(17) 0.63660(10) 0.0296(5) Uani 1 1 d . . . . .
C15A C 0.3644(2) 0.47453(17) 0.56910(10) 0.0302(6) Uani 1 1 d . . . . .
H19A H 0.398496 0.470090 0.535989 0.036 Uiso 1 1 calc R U . . .
C18 C 1.0162(2) 0.58502(18) 0.59406(10) 0.0323(6) Uani 1 1 d . . . . .
C16A C 0.4129(2) 0.53002(18) 0.60802(10) 0.0309(6) Uani 1 1 d . . . . .
C6 C 0.6386(2) 0.43543(18) 0.72557(10) 0.0314(6) Uani 1 1 d . . . . .
C11 C 0.7375(2) 0.36952(19) 0.53009(10) 0.0356(6) Uani 1 1 d . . . . .
H11 H 0.766978 0.392913 0.496626 0.043 Uiso 1 1 calc R U . . .
H10 H 0.656547 0.372702 0.525638 0.043 Uiso 1 1 calc R U . . .
C17 C 0.8698(2) 0.54271(18) 0.65980(10) 0.0320(6) Uani 1 1 d . . . . .
C7A C 0.2189(2) 0.48748(19) 0.71423(11) 0.0350(6) Uani 1 1 d . . . . .
H9A H 0.246574 0.528808 0.741314 0.042 Uiso 1 1 calc R U . . .
C6A C 0.1331(2) 0.43183(19) 0.72364(10) 0.0341(6) Uani 1 1 d . . . . .
C17A C 0.3649(2) 0.53841(19) 0.65896(10) 0.0340(6) Uani 1 1 d . . . . .
C7 C 0.7248(2) 0.49100(18) 0.71597(10) 0.0327(6) Uani 1 1 d . . . . .
H9 H 0.752633 0.532288 0.743051 0.039 Uiso 1 1 calc R U . . .
C11A C 0.2299(2) 0.37026(18) 0.52693(10) 0.0342(6) Uani 1 1 d . . . . .
H10A H 0.262335 0.394606 0.494458 0.041 Uiso 1 1 calc R U . . .
H11A H 0.149573 0.379248 0.521908 0.041 Uiso 1 1 calc R U . . .
C19A C 0.6555(2) 0.68951(19) 0.62601(11) 0.0366(6) Uani 1 1 d . . . . .
H21A H 0.689846 0.668715 0.593239 0.044 Uiso 1 1 calc R U . . .
H22A H 0.708984 0.679591 0.657140 0.044 Uiso 1 1 calc R U . . .
C19 C 1.1556(2) 0.6977(2) 0.62451(12) 0.0400(7) Uani 1 1 d . . . . .
H22 H 1.212396 0.686610 0.654090 0.048 Uiso 1 1 calc R U . A 1
H21 H 1.186772 0.679827 0.590324 0.048 Uiso 1 1 calc R U . A 1
C1 C 0.4364(2) 0.3266(2) 0.73963(11) 0.0366(6) Uani 1 1 d . . . . .
H1 H 0.413446 0.391468 0.741098 0.044 Uiso 1 1 calc R U . . .
H2 H 0.476466 0.310668 0.774281 0.044 Uiso 1 1 calc R U . . .
C1A C -0.0665(2) 0.3196(2) 0.73823(11) 0.0391(7) Uani 1 1 d . . . . .
H1A H -0.089986 0.384206 0.740768 0.047 Uiso 1 1 calc R U . . .
H2A H -0.025135 0.302588 0.772362 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5401(2) 0.21510(19) 0.69334(12) 0.0399(7) Uani 1 1 d . . . . .
H7 H 0.584877 0.199553 0.726744 0.048 Uiso 1 1 calc R U . . .
H8 H 0.585119 0.204454 0.662327 0.048 Uiso 1 1 calc R U . . .
C20A C 0.6315(2) 0.7907(2) 0.62095(11) 0.0385(6) Uani 1 1 d . . . . .
C2 C 0.3375(2) 0.2656(2) 0.72981(12) 0.0407(7) Uani 1 1 d . . . . .
H4 H 0.285798 0.276577 0.758066 0.049 Uiso 1 1 calc R U . . .
H3 H 0.299602 0.280791 0.694512 0.049 Uiso 1 1 calc R U . . .
C4A C 0.0373(2) 0.21094(19) 0.68973(13) 0.0420(7) Uani 1 1 d . . . . .
H7A H 0.082730 0.194751 0.722818 0.050 Uiso 1 1 calc R U . . .
H8A H 0.081982 0.201949 0.658434 0.050 Uiso 1 1 calc R U . . .
C20 C 1.1310(19) 0.7917(16) 0.6226(7) 0.029(3) Uani 0.5 1 d . U P B 1
C2A C -0.1649(2) 0.2580(2) 0.72819(13) 0.0446(7) Uani 1 1 d . . . . .
H4A H -0.215743 0.267129 0.757067 0.054 Uiso 1 1 calc R U . . .
H3A H -0.204204 0.274610 0.693439 0.054 Uiso 1 1 calc R U . . .
C21A C 0.7155(3) 0.8525(2) 0.63421(12) 0.0491(8) Uani 1 1 d . . . . .
H23A H 0.786287 0.830458 0.645867 0.059 Uiso 1 1 calc R U . . .
C3A C -0.0623(3) 0.1502(2) 0.68434(15) 0.0546(9) Uani 1 1 d . . . . .
H5A H -0.103229 0.162405 0.649352 0.066 Uiso 1 1 calc R U . . .
H6A H -0.038713 0.085390 0.684584 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4399(3) 0.1553(2) 0.68834(14) 0.0505(8) Uani 1 1 d . . . . .
H5 H 0.399674 0.166778 0.653080 0.061 Uiso 1 1 calc R U . . .
H6 H 0.462708 0.090335 0.689370 0.061 Uiso 1 1 calc R U . . .
C12A C 0.2524(3) 0.2691(2) 0.53008(14) 0.0532(8) Uani 1 1 d . . . . .
H13A H 0.332547 0.263317 0.527568 0.064 Uiso 1 1 calc R U . C 1
H12A H 0.238361 0.251654 0.567458 0.064 Uiso 1 1 calc R U . C 1
C25A C 0.5293(3) 0.8235(2) 0.60506(15) 0.0538(8) Uani 1 1 d . . . . .
H27A H 0.470933 0.782225 0.595996 0.065 Uiso 1 1 calc R U . . .
C12 C 0.7725(3) 0.2704(2) 0.53854(14) 0.0531(9) Uani 1 1 d . . . . .
H12 H 0.754651 0.253359 0.575463 0.064 Uiso 1 1 calc R U . D 1
H13 H 0.724631 0.232993 0.513490 0.064 Uiso 1 1 calc R U . D 1
C21 C 1.1863(16) 0.8721(18) 0.6318(11) 0.050(4) Uani 0.5 1 d . U P B 1
H23 H 1.258095 0.864024 0.648246 0.060 Uiso 0.5 1 calc R U P B 1
C22A C 0.6968(3) 0.9457(2) 0.63055(14) 0.0600(10) Uani 1 1 d . . . . .
H24A H 0.754799 0.987417 0.639529 0.072 Uiso 1 1 calc R U . . .
C23A C 0.5958(4) 0.9776(3) 0.61413(16) 0.0648(10) Uani 1 1 d . . . . .
H25A H 0.583465 1.041635 0.610873 0.078 Uiso 1 1 calc R U . . .
C24A C 0.5114(3) 0.9175(3) 0.60226(18) 0.0671(11) Uani 1 1 d . . . . .
H26A H 0.440190 0.940251 0.592050 0.081 Uiso 1 1 calc R U . . .
C25 C 1.0282(17) 0.8294(14) 0.5826(6) 0.058(4) Uani 0.5 1 d . U P B 1
H27 H 0.983921 0.783849 0.564680 0.070 Uiso 0.5 1 calc R U P B 1
C22 C 1.1590(16) 0.9636(14) 0.6221(8) 0.061(5) Uani 0.5 1 d . U P B 1
H24 H 1.212(6) 1.016(6) 0.637(3) 0.073 Uiso 0.5 1 d . U P E 1
C23 C 1.0633(17) 0.9858(14) 0.5920(6) 0.072(4) Uani 0.5 1 d . U P B 1
H25 H 1.049(7) 1.050(6) 0.585(3) 0.086 Uiso 0.5 1 d . U P F 1
C24 C 0.9994(16) 0.9150(13) 0.5721(5) 0.073(4) Uani 0.5 1 d . U P B 1
H26 H 0.933978 0.927548 0.550581 0.087 Uiso 0.5 1 calc R U P B 1
H20A H 0.525(3) 0.633(2) 0.6654(13) 0.046(9) Uiso 1 1 d . . . . .
H20 H 1.030(3) 0.638(2) 0.6665(15) 0.064(11) Uiso 1 1 d . . . . .
C13B C 0.3698(3) 0.2412(3) 0.53340(17) 0.0421(9) Uani 0.75 1 d . U P G 2
H14B H 0.405938 0.264121 0.567598 0.051 Uiso 0.75 1 calc R U P G 2
H15B H 0.406504 0.269761 0.503355 0.051 Uiso 0.75 1 calc R U P G 2
C14B C 0.3836(4) 0.1386(3) 0.53079(19) 0.0517(11) Uani 0.75 1 d . U P G 2
H17B H 0.355842 0.116474 0.495249 0.078 Uiso 0.75 1 calc R U P G 2
H16B H 0.342521 0.109667 0.558688 0.078 Uiso 0.75 1 calc R U P G 2
H18B H 0.461473 0.123111 0.536721 0.078 Uiso 0.75 1 calc R U P G 2
C27 C 0.7121(4) 0.2023(3) 0.50398(18) 0.0519(12) Uani 0.7 1 d . U P H 2
H29 H 0.718751 0.218834 0.465742 0.062 Uiso 0.7 1 calc R U P H 2
H28 H 0.633395 0.205044 0.511008 0.062 Uiso 0.7 1 calc R U P H 2
C32 C 0.7528(6) 0.1053(3) 0.5131(2) 0.0712(17) Uani 0.7 1 d . U P H 2
H40 H 0.704960 0.062881 0.491959 0.107 Uiso 0.7 1 calc R U P H 2
H41 H 0.751879 0.090030 0.551454 0.107 Uiso 0.7 1 calc R U P H 2
H42 H 0.827751 0.100112 0.501837 0.107 Uiso 0.7 1 calc R U P H 2
C13A C 0.2140(11) 0.2093(10) 0.5030(5) 0.057(4) Uani 0.25 1 d . U P G 1
H14A H 0.223297 0.225090 0.464879 0.068 Uiso 0.25 1 calc R U P G 1
H15A H 0.134306 0.207671 0.507685 0.068 Uiso 0.25 1 calc R U P G 1
C14A C 0.263(2) 0.1046(11) 0.5140(7) 0.092(6) Uani 0.25 1 d . U P G 1
H17A H 0.232417 0.063191 0.485901 0.138 Uiso 0.25 1 calc R U P G 1
H16A H 0.243404 0.083035 0.549315 0.138 Uiso 0.25 1 calc R U P G 1
H18A H 0.343360 0.105673 0.513169 0.138 Uiso 0.25 1 calc R U P G 1
C13 C 0.8653(8) 0.2456(7) 0.5335(4) 0.043(2) Uani 0.3 1 d . U P H 1
H14 H 0.912659 0.269670 0.564157 0.051 Uiso 0.3 1 calc R U P H 1
H15 H 0.890820 0.272917 0.500132 0.051 Uiso 0.3 1 calc R U P H 1
C14 C 0.8810(12) 0.1361(10) 0.5308(6) 0.076(4) Uani 0.3 1 d . U P H 1
H18 H 0.959090 0.121677 0.529819 0.114 Uiso 0.3 1 calc R U P H 1
H17 H 0.841200 0.112282 0.498221 0.114 Uiso 0.3 1 calc R U P H 1
H16 H 0.852199 0.107886 0.562651 0.114 Uiso 0.3 1 calc R U P H 1
C35 C 1.0277(16) 0.8206(11) 0.6007(5) 0.048(3) Uani 0.5 1 d . U P B 2
H39 H 0.971743 0.775626 0.596145 0.058 Uiso 0.5 1 calc R U P B 2
C34 C 1.0087(13) 0.9188(11) 0.5965(5) 0.064(3) Uani 0.5 1 d . U P B 2
H38 H 0.938801 0.941639 0.584041 0.077 Uiso 0.5 1 calc R U P B 2
C33 C 1.0945(13) 0.9793(10) 0.6110(6) 0.051(3) Uani 0.5 1 d . U P B 2
H37 H 1.082438 1.043238 0.606870 0.062 Uiso 0.5 1 calc R U P B 2
C31 C 1.1950(14) 0.9492(15) 0.6310(8) 0.048(3) Uani 0.5 1 d . U P B 2
H36 H 1.251015 0.991956 0.641426 0.058 Uiso 0.5 1 calc R U P B 2
C30 C 1.2151(15) 0.8567(17) 0.6361(10) 0.039(3) Uani 0.5 1 d . U P B 2
H32 H 1.279230 0.830548 0.653539 0.047 Uiso 0.5 1 calc R U P B 2
C29 C 1.122(2) 0.8040(17) 0.6104(7) 0.037(3) Uani 0.5 1 d . U P B 2


_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
F1 C6 1.352(3) . ?
F2A C10A 1.352(3) . ?
F2 C10 1.353(3) . ?
F1A C6A 1.356(3) . ?
O3 C18 1.234(3) . ?
O3A C18A 1.233(3) . ?
O2 C17 1.251(3) . ?
O1 C2 1.421(4) . ?
O1 C3 1.426(4) . ?
N2 C9 1.398(3) . ?
N2 C15 1.350(3) . ?
N2 C11 1.480(3) . ?
O2A C17A 1.254(3) . ?
N2A C9A 1.400(3) . ?
N2A C15A 1.356(3) . ?
N2A C11A 1.482(3) . ?
O1A C2A 1.419(4) . ?
O1A C3A 1.427(4) . ?
N1 C5 1.409(3) . ?
N1 C1 1.471(3) . ?
N1 C4 1.478(3) . ?
N3A C18A 1.341(3) . ?
N3A C19A 1.448(3) . ?
N3A H20A 0.93(3) . ?
N1A C5A 1.405(3) . ?
N1A C1A 1.474(3) . ?
N1A C4A 1.477(4) . ?
N3 C18 1.344(3) . ?
N3 C19 1.452(3) . ?
N3 H20 0.95(4) . ?
C8 C9 1.399(4) . ?
C8 C17 1.459(4) . ?
C8 C7 1.401(3) . ?
C9A C8A 1.405(4) . ?
C9A C10A 1.410(4) . ?
C9 C10 1.415(3) . ?
C15 H19 0.9500 . ?
C15 C16 1.370(3) . ?
C16 C18 1.489(3) . ?
C16 C17 1.435(3) . ?
C8A C7A 1.401(3) . ?
C8A C17A 1.459(4) . ?
C5 C10 1.394(3) . ?
C5 C6 1.395(4) . ?
C10A C5A 1.392(3) . ?
C5A C6A 1.405(4) . ?
C18A C16A 1.496(4) . ?
C15A H19A 0.9500 . ?
C15A C16A 1.367(4) . ?
C16A C17A 1.437(3) . ?
C6 C7 1.364(4) . ?
C11 H11 0.9900 . ?
C11 H10 0.9900 . ?
C11 C12 1.521(4) . ?
C7A H9A 0.9500 . ?
C7A C6A 1.360(4) . ?
C7 H9 0.9500 . ?
C11A H10A 0.9900 . ?
C11A H11A 0.9900 . ?
C11A C12A 1.505(4) . ?
C19A H21A 0.9900 . ?
C19A H22A 0.9900 . ?
C19A C20A 1.512(4) . ?
C19 H22 0.9900 . ?
C19 H21 0.9900 . ?
C19 C20 1.41(2) . ?
C19 C29 1.64(2) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C1 C2 1.508(4) . ?
C1A H1A 0.9900 . ?
C1A H2A 0.9900 . ?
C1A C2A 1.510(4) . ?
C4 H7 0.9900 . ?
C4 H8 0.9900 . ?
C4 C3 1.503(4) . ?
C20A C21A 1.390(4) . ?
C20A C25A 1.371(4) . ?
C2 H4 0.9900 . ?
C2 H3 0.9900 . ?
C4A H7A 0.9900 . ?
C4A H8A 0.9900 . ?
C4A C3A 1.506(4) . ?
C20 C21 1.37(4) . ?
C20 C25 1.65(3) . ?
C2A H4A 0.9900 . ?
C2A H3A 0.9900 . ?
C21A H23A 0.9500 . ?
C21A C22A 1.383(5) . ?
C3A H5A 0.9900 . ?
C3A H6A 0.9900 . ?
C3 H5 0.9900 . ?
C3 H6 0.9900 . ?
C12A H13A 0.9900 . ?
C12A H12A 0.9900 . ?
C12A C13B 1.489(5) . ?
C12A C13A 1.180(11) . ?
C25A H27A 0.9500 . ?
C25A C24A 1.392(5) . ?
C12 H12 0.9900 . ?
C12 H13 0.9900 . ?
C12 C27 1.479(5) . ?
C12 C13 1.206(10) . ?
C21 H23 0.9500 . ?
C21 C22 1.40(3) . ?
C22A H24A 0.9500 . ?
C22A C23A 1.358(6) . ?
C23A H25A 0.9500 . ?
C23A C24A 1.372(6) . ?
C24A H26A 0.9500 . ?
C25 H27 0.9500 . ?
C25 C24 1.32(3) . ?
C22 H24 1.05(8) . ?
C22 C23 1.383(18) . ?
C23 H25 0.98(9) . ?
C23 C24 1.37(3) . ?
C24 H26 0.9500 . ?
C13B H14B 0.9900 . ?
C13B H15B 0.9900 . ?
C13B C14B 1.511(6) . ?
C14B H17B 0.9800 . ?
C14B H16B 0.9800 . ?
C14B H18B 0.9800 . ?
C27 H29 0.9900 . ?
C27 H28 0.9900 . ?
C27 C32 1.515(7) . ?
C32 H40 0.9800 . ?
C32 H41 0.9800 . ?
C32 H42 0.9800 . ?
C13A H14A 0.9900 . ?
C13A H15A 0.9900 . ?
C13A C14A 1.66(2) . ?
C14A H17A 0.9800 . ?
C14A H16A 0.9800 . ?
C14A H18A 0.9800 . ?
C13 H14 0.9900 . ?
C13 H15 0.9900 . ?
C13 C14 1.614(17) . ?
C14 H18 0.9800 . ?
C14 H17 0.9800 . ?
C14 H16 0.9800 . ?
C35 H39 0.9500 . ?
C35 C34 1.46(2) . ?
C35 C29 1.18(3) . ?
C34 H38 0.9500 . ?
C34 C33 1.40(2) . ?
C33 H37 0.9500 . ?
C33 C31 1.368(17) . ?
C31 H36 0.9500 . ?
C31 C30 1.38(3) . ?
C30 H32 0.9500 . ?
C30 C29 1.49(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.4(2) . . ?
C9 N2 C11 123.6(2) . . ?
C15 N2 C9 119.0(2) . . ?
C15 N2 C11 117.3(2) . . ?
C9A N2A C11A 123.4(2) . . ?
C15A N2A C9A 119.0(2) . . ?
C15A N2A C11A 117.6(2) . . ?
C2A O1A C3A 109.9(2) . . ?
C5 N1 C1 119.0(2) . . ?
C5 N1 C4 114.8(2) . . ?
C1 N1 C4 109.3(2) . . ?
C18A N3A C19A 122.8(2) . . ?
C18A N3A H20A 115(2) . . ?
C19A N3A H20A 123(2) . . ?
C5A N1A C1A 118.9(2) . . ?
C5A N1A C4A 114.7(2) . . ?
C1A N1A C4A 109.3(2) . . ?
C18 N3 C19 122.6(2) . . ?
C18 N3 H20 116(2) . . ?
C19 N3 H20 121(2) . . ?
C9 C8 C17 121.8(2) . . ?
C9 C8 C7 120.3(2) . . ?
C7 C8 C17 117.9(2) . . ?
N2A C9A C8A 118.8(2) . . ?
N2A C9A C10A 124.8(2) . . ?
C8A C9A C10A 116.4(2) . . ?
N2 C9 C8 119.3(2) . . ?
N2 C9 C10 124.2(2) . . ?
C8 C9 C10 116.6(2) . . ?
N2 C15 H19 117.5 . . ?
N2 C15 C16 124.9(2) . . ?
C16 C15 H19 117.5 . . ?
C15 C16 C18 116.7(2) . . ?
C15 C16 C17 119.4(2) . . ?
C17 C16 C18 123.9(2) . . ?
C9A C8A C17A 122.2(2) . . ?
C7A C8A C9A 120.5(2) . . ?
C7A C8A C17A 117.3(2) . . ?
C10 C5 N1 118.2(2) . . ?
C10 C5 C6 115.6(2) . . ?
C6 C5 N1 126.2(2) . . ?
F2A C10A C9A 119.6(2) . . ?
F2A C10A C5A 116.0(2) . . ?
C5A C10A C9A 124.4(2) . . ?
N1A C5A C6A 126.4(2) . . ?
C10A C5A N1A 118.3(2) . . ?
C10A C5A C6A 115.3(2) . . ?
O3A C18A N3A 123.1(2) . . ?
O3A C18A C16A 121.5(2) . . ?
N3A C18A C16A 115.4(2) . . ?
F2 C10 C9 119.9(2) . . ?
F2 C10 C5 116.0(2) . . ?
C5 C10 C9 124.1(2) . . ?
N2A C15A H19A 117.4 . . ?
N2A C15A C16A 125.2(2) . . ?
C16A C15A H19A 117.4 . . ?
O3 C18 N3 123.1(2) . . ?
O3 C18 C16 121.8(2) . . ?
N3 C18 C16 115.2(2) . . ?
C15A C16A C18A 116.8(2) . . ?
C15A C16A C17A 119.5(2) . . ?
C17A C16A C18A 123.7(2) . . ?
F1 C6 C5 119.2(2) . . ?
F1 C6 C7 117.9(2) . . ?
C7 C6 C5 122.8(2) . . ?
N2 C11 H11 109.3 . . ?
N2 C11 H10 109.3 . . ?
N2 C11 C12 111.7(2) . . ?
H11 C11 H10 107.9 . . ?
C12 C11 H11 109.3 . . ?
C12 C11 H10 109.3 . . ?
O2 C17 C8 119.6(2) . . ?
O2 C17 C16 124.8(2) . . ?
C16 C17 C8 115.6(2) . . ?
C8A C7A H9A 120.0 . . ?
C6A C7A C8A 120.0(3) . . ?
C6A C7A H9A 120.0 . . ?
F1A C6A C5A 118.9(2) . . ?
F1A C6A C7A 118.1(2) . . ?
C7A C6A C5A 122.9(2) . . ?
O2A C17A C8A 120.1(2) . . ?
O2A C17A C16A 124.6(2) . . ?
C16A C17A C8A 115.3(2) . . ?
C8 C7 H9 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H9 119.9 . . ?
N2A C11A H10A 108.3 . . ?
N2A C11A H11A 108.3 . . ?
N2A C11A C12A 116.1(2) . . ?
H10A C11A H11A 107.4 . . ?
C12A C11A H10A 108.3 . . ?
C12A C11A H11A 108.3 . . ?
N3A C19A H21A 108.8 . . ?
N3A C19A H22A 108.8 . . ?
N3A C19A C20A 113.7(2) . . ?
H21A C19A H22A 107.7 . . ?
C20A C19A H21A 108.8 . . ?
C20A C19A H22A 108.8 . . ?
N3 C19 H22 108.8 . . ?
N3 C19 H21 108.8 . . ?
N3 C19 C29 112.8(10) . . ?
H22 C19 H21 107.7 . . ?
C20 C19 N3 113.6(10) . . ?
C20 C19 H22 108.8 . . ?
C20 C19 H21 108.8 . . ?
N1 C1 H1 110.2 . . ?
N1 C1 H2 110.2 . . ?
N1 C1 C2 107.3(2) . . ?
H1 C1 H2 108.5 . . ?
C2 C1 H1 110.2 . . ?
C2 C1 H2 110.2 . . ?
N1A C1A H1A 110.3 . . ?
N1A C1A H2A 110.3 . . ?
N1A C1A C2A 107.0(2) . . ?
H1A C1A H2A 108.6 . . ?
C2A C1A H1A 110.3 . . ?
C2A C1A H2A 110.3 . . ?
N1 C4 H7 109.7 . . ?
N1 C4 H8 109.7 . . ?
N1 C4 C3 109.6(2) . . ?
H7 C4 H8 108.2 . . ?
C3 C4 H7 109.7 . . ?
C3 C4 H8 109.7 . . ?
C21A C20A C19A 118.6(3) . . ?
C25A C20A C19A 122.2(3) . . ?
C25A C20A C21A 119.1(3) . . ?
O1 C2 C1 111.0(2) . . ?
O1 C2 H4 109.4 . . ?
O1 C2 H3 109.4 . . ?
C1 C2 H4 109.4 . . ?
C1 C2 H3 109.4 . . ?
H4 C2 H3 108.0 . . ?
N1A C4A H7A 109.8 . . ?
N1A C4A H8A 109.8 . . ?
N1A C4A C3A 109.5(2) . . ?
H7A C4A H8A 108.2 . . ?
C3A C4A H7A 109.8 . . ?
C3A C4A H8A 109.8 . . ?
C19 C20 C25 120.1(17) . . ?
C21 C20 C19 137.0(18) . . ?
C21 C20 C25 99.3(17) . . ?
O1A C2A C1A 111.1(2) . . ?
O1A C2A H4A 109.4 . . ?
O1A C2A H3A 109.4 . . ?
C1A C2A H4A 109.4 . . ?
C1A C2A H3A 109.4 . . ?
H4A C2A H3A 108.0 . . ?
C20A C21A H23A 119.8 . . ?
C22A C21A C20A 120.5(3) . . ?
C22A C21A H23A 119.8 . . ?
O1A C3A C4A 112.0(3) . . ?
O1A C3A H5A 109.2 . . ?
O1A C3A H6A 109.2 . . ?
C4A C3A H5A 109.2 . . ?
C4A C3A H6A 109.2 . . ?
H5A C3A H6A 107.9 . . ?
O1 C3 C4 112.1(3) . . ?
O1 C3 H5 109.2 . . ?
O1 C3 H6 109.2 . . ?
C4 C3 H5 109.2 . . ?
C4 C3 H6 109.2 . . ?
H5 C3 H6 107.9 . . ?
C11A C12A H13A 105.0 . . ?
C11A C12A H12A 105.0 . . ?
H13A C12A H12A 105.8 . . ?
C13B C12A C11A 116.3(3) . . ?
C13A C12A C11A 129.2(9) . . ?
C13A C12A H13A 105.0 . . ?
C13A C12A H12A 105.0 . . ?
C20A C25A H27A 120.1 . . ?
C20A C25A C24A 119.8(3) . . ?
C24A C25A H27A 120.1 . . ?
C11 C12 H12 106.8 . . ?
C11 C12 H13 106.8 . . ?
H12 C12 H13 106.7 . . ?
C27 C12 C11 115.8(4) . . ?
C13 C12 C11 121.9(5) . . ?
C13 C12 H12 106.8 . . ?
C13 C12 H13 106.8 . . ?
C20 C21 H23 113.4 . . ?
C20 C21 C22 133.2(17) . . ?
C22 C21 H23 113.4 . . ?
C21A C22A H24A 120.0 . . ?
C23A C22A C21A 120.1(4) . . ?
C23A C22A H24A 120.0 . . ?
C22A C23A H25A 120.0 . . ?
C22A C23A C24A 120.1(4) . . ?
C24A C23A H25A 120.0 . . ?
C25A C24A H26A 119.8 . . ?
C23A C24A C25A 120.5(4) . . ?
C23A C24A H26A 119.8 . . ?
C20 C25 H27 115.9 . . ?
C24 C25 C20 128(2) . . ?
C24 C25 H27 115.9 . . ?
C21 C22 H24 120(5) . . ?
C23 C22 C21 120.1(18) . . ?
C23 C22 H24 120(5) . . ?
C22 C23 H25 117(6) . . ?
C24 C23 C22 117.4(18) . . ?
C24 C23 H25 125(5) . . ?
C25 C24 C23 120.4(18) . . ?
C25 C24 H26 119.8 . . ?
C23 C24 H26 119.8 . . ?
C12A C13B H14B 109.1 . . ?
C12A C13B H15B 109.1 . . ?
C12A C13B C14B 112.3(3) . . ?
H14B C13B H15B 107.9 . . ?
C14B C13B H14B 109.1 . . ?
C14B C13B H15B 109.1 . . ?
C13B C14B H17B 109.5 . . ?
C13B C14B H16B 109.5 . . ?
C13B C14B H18B 109.5 . . ?
H17B C14B H16B 109.5 . . ?
H17B C14B H18B 109.5 . . ?
H16B C14B H18B 109.5 . . ?
C12 C27 H29 108.9 . . ?
C12 C27 H28 108.9 . . ?
C12 C27 C32 113.3(5) . . ?
H29 C27 H28 107.7 . . ?
C32 C27 H29 108.9 . . ?
C32 C27 H28 108.9 . . ?
C27 C32 H40 109.5 . . ?
C27 C32 H41 109.5 . . ?
C27 C32 H42 109.5 . . ?
H40 C32 H41 109.5 . . ?
H40 C32 H42 109.5 . . ?
H41 C32 H42 109.5 . . ?
C12A C13A H14A 107.9 . . ?
C12A C13A H15A 107.9 . . ?
C12A C13A C14A 117.5(13) . . ?
H14A C13A H15A 107.2 . . ?
C14A C13A H14A 107.9 . . ?
C14A C13A H15A 107.9 . . ?
C13A C14A H17A 109.5 . . ?
C13A C14A H16A 109.5 . . ?
C13A C14A H18A 109.5 . . ?
H17A C14A H16A 109.5 . . ?
H17A C14A H18A 109.5 . . ?
H16A C14A H18A 109.5 . . ?
C12 C13 H14 108.6 . . ?
C12 C13 H15 108.6 . . ?
C12 C13 C14 114.6(9) . . ?
H14 C13 H15 107.6 . . ?
C14 C13 H14 108.6 . . ?
C14 C13 H15 108.6 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H17 109.5 . . ?
C13 C14 H16 109.5 . . ?
H18 C14 H17 109.5 . . ?
H18 C14 H16 109.5 . . ?
H17 C14 H16 109.5 . . ?
C34 C35 H39 124.3 . . ?
C29 C35 H39 124.3 . . ?
C29 C35 C34 111.4(19) . . ?
C35 C34 H38 120.3 . . ?
C33 C34 C35 119.4(14) . . ?
C33 C34 H38 120.3 . . ?
C34 C33 H37 119.0 . . ?
C31 C33 C34 122.0(16) . . ?
C31 C33 H37 119.0 . . ?
C33 C31 H36 120.0 . . ?
C33 C31 C30 120.0(19) . . ?
C30 C31 H36 120.0 . . ?
C31 C30 H32 125.0 . . ?
C31 C30 C29 110.0(16) . . ?
C29 C30 H32 125.0 . . ?
C35 C29 C19 118(2) . . ?
C35 C29 C30 133(3) . . ?
C30 C29 C19 102.9(15) . . ?

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
F1 C6 C7 C8 175.0(2) . . . . ?
F2A C10A C5A N1A 7.3(3) . . . . ?
F2A C10A C5A C6A -173.9(2) . . . . ?
O3A C18A C16A C15A 0.2(4) . . . . ?
O3A C18A C16A C17A -179.1(3) . . . . ?
N2 C9 C10 F2 -3.4(4) . . . . ?
N2 C9 C10 C5 174.0(2) . . . . ?
N2 C15 C16 C18 -177.9(2) . . . . ?
N2 C15 C16 C17 1.0(4) . . . . ?
N2 C11 C12 C27 162.8(3) . . . . ?
N2 C11 C12 C13 -75.1(7) . . . . ?
N2A C9A C8A C7A -179.3(2) . . . . ?
N2A C9A C8A C17A -0.8(4) . . . . ?
N2A C9A C10A F2A -5.5(4) . . . . ?
N2A C9A C10A C5A 172.7(2) . . . . ?
N2A C15A C16A C18A -178.9(2) . . . . ?
N2A C15A C16A C17A 0.5(4) . . . . ?
N2A C11A C12A C13B -62.6(4) . . . . ?
N2A C11A C12A C13A 166.4(8) . . . . ?
N1 C5 C10 F2 5.1(3) . . . . ?
N1 C5 C10 C9 -172.4(2) . . . . ?
N1 C5 C6 F1 -1.0(4) . . . . ?
N1 C5 C6 C7 176.1(2) . . . . ?
N1 C1 C2 O1 62.9(3) . . . . ?
N1 C4 C3 O1 -55.9(3) . . . . ?
N3A C18A C16A C15A 179.6(2) . . . . ?
N3A C18A C16A C17A 0.3(4) . . . . ?
N3A C19A C20A C21A 156.0(3) . . . . ?
N3A C19A C20A C25A -22.3(4) . . . . ?
N1A C5A C6A F1A -1.7(4) . . . . ?
N1A C5A C6A C7A 175.1(2) . . . . ?
N1A C1A C2A O1A 62.6(3) . . . . ?
N1A C4A C3A O1A -55.8(3) . . . . ?
N3 C19 C20 C21 156(2) . . . . ?
N3 C19 C20 C25 -50.7(17) . . . . ?
N3 C19 C29 C35 -11(2) . . . . ?
N3 C19 C29 C30 146.2(14) . . . . ?
C8 C9 C10 F2 177.5(2) . . . . ?
C8 C9 C10 C5 -5.1(4) . . . . ?
C9A N2A C15A C16A -2.0(4) . . . . ?
C9A N2A C11A C12A -76.8(3) . . . . ?
C9A C8A C7A C6A 4.6(4) . . . . ?
C9A C8A C17A O2A 179.7(3) . . . . ?
C9A C8A C17A C16A -0.6(4) . . . . ?
C9A C10A C5A N1A -170.9(2) . . . . ?
C9A C10A C5A C6A 7.9(4) . . . . ?
C9 N2 C15 C16 -2.7(4) . . . . ?
C9 N2 C11 C12 -77.8(3) . . . . ?
C9 C8 C17 O2 179.8(3) . . . . ?
C9 C8 C17 C16 -0.9(4) . . . . ?
C9 C8 C7 C6 3.9(4) . . . . ?
C15 N2 C9 C8 2.5(3) . . . . ?
C15 N2 C9 C10 -176.6(2) . . . . ?
C15 N2 C11 C12 98.6(3) . . . . ?
C15 C16 C18 O3 0.6(4) . . . . ?
C15 C16 C18 N3 -180.0(2) . . . . ?
C15 C16 C17 O2 -179.9(3) . . . . ?
C15 C16 C17 C8 0.8(4) . . . . ?
C8A C9A C10A F2A 176.0(2) . . . . ?
C8A C9A C10A C5A -5.8(4) . . . . ?
C8A C7A C6A F1A 174.4(2) . . . . ?
C8A C7A C6A C5A -2.4(4) . . . . ?
C5 N1 C1 C2 165.4(2) . . . . ?
C5 N1 C4 C3 -166.2(2) . . . . ?
C5 C6 C7 C8 -2.1(4) . . . . ?
C10A C9A C8A C7A -0.7(4) . . . . ?
C10A C9A C8A C17A 177.8(2) . . . . ?
C10A C5A C6A F1A 179.6(2) . . . . ?
C10A C5A C6A C7A -3.6(4) . . . . ?
C5A N1A C1A C2A 165.2(2) . . . . ?
C5A N1A C4A C3A -165.7(3) . . . . ?
C18A N3A C19A C20A 107.6(3) . . . . ?
C18A C16A C17A O2A -0.2(4) . . . . ?
C18A C16A C17A C8A -179.8(2) . . . . ?
C10 C5 C6 F1 179.9(2) . . . . ?
C10 C5 C6 C7 -3.0(4) . . . . ?
C15A N2A C9A C8A 2.1(3) . . . . ?
C15A N2A C9A C10A -176.4(2) . . . . ?
C15A N2A C11A C12A 102.4(3) . . . . ?
C15A C16A C17A O2A -179.5(3) . . . . ?
C15A C16A C17A C8A 0.8(4) . . . . ?
C18 N3 C19 C20 110.3(8) . . . . ?
C18 N3 C19 C29 98.8(8) . . . . ?
C18 C16 C17 O2 -1.1(4) . . . . ?
C18 C16 C17 C8 179.6(2) . . . . ?
C6 C5 C10 F2 -175.8(2) . . . . ?
C6 C5 C10 C9 6.7(4) . . . . ?
C11 N2 C9 C8 178.9(2) . . . . ?
C11 N2 C9 C10 -0.2(4) . . . . ?
C11 N2 C15 C16 -179.3(2) . . . . ?
C11 C12 C27 C32 178.3(3) . . . . ?
C11 C12 C13 C14 -166.9(7) . . . . ?
C17 C8 C9 N2 -0.8(4) . . . . ?
C17 C8 C9 C10 178.4(2) . . . . ?
C17 C8 C7 C6 -175.0(2) . . . . ?
C17 C16 C18 O3 -178.3(3) . . . . ?
C17 C16 C18 N3 1.2(4) . . . . ?
C7A C8A C17A O2A -1.8(4) . . . . ?
C7A C8A C17A C16A 177.9(2) . . . . ?
C17A C8A C7A C6A -173.9(2) . . . . ?
C7 C8 C9 N2 -179.6(2) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C7 C8 C17 O2 -1.3(4) . . . . ?
C7 C8 C17 C16 178.0(2) . . . . ?
C11A N2A C9A C8A -178.7(2) . . . . ?
C11A N2A C9A C10A 2.8(4) . . . . ?
C11A N2A C15A C16A 178.8(2) . . . . ?
C11A C12A C13B C14B -174.3(3) . . . . ?
C11A C12A C13A C14A 175.5(8) . . . . ?
C19A N3A C18A O3A 1.3(4) . . . . ?
C19A N3A C18A C16A -178.1(2) . . . . ?
C19A C20A C21A C22A -179.5(3) . . . . ?
C19A C20A C25A C24A 178.6(3) . . . . ?
C19 N3 C18 O3 2.1(4) . . . . ?
C19 N3 C18 C16 -177.3(2) . . . . ?
C19 C20 C21 C22 170(2) . . . . ?
C19 C20 C25 C24 -173.5(15) . . . . ?
C1 N1 C5 C10 -160.3(2) . . . . ?
C1 N1 C5 C6 20.6(4) . . . . ?
C1 N1 C4 C3 57.1(3) . . . . ?
C1A N1A C5A C10A -161.4(2) . . . . ?
C1A N1A C5A C6A 20.0(4) . . . . ?
C1A N1A C4A C3A 57.9(3) . . . . ?
C4 N1 C5 C10 67.4(3) . . . . ?
C4 N1 C5 C6 -111.7(3) . . . . ?
C4 N1 C1 C2 -59.9(3) . . . . ?
C20A C21A C22A C23A 0.3(5) . . . . ?
C20A C25A C24A C23A 1.4(6) . . . . ?
C2 O1 C3 C4 57.5(3) . . . . ?
C4A N1A C5A C10A 66.6(3) . . . . ?
C4A N1A C5A C6A -112.0(3) . . . . ?
C4A N1A C1A C2A -60.5(3) . . . . ?
C20 C21 C22 C23 -9(4) . . . . ?
C20 C25 C24 C23 6(3) . . . . ?
C2A O1A C3A C4A 57.0(3) . . . . ?
C21A C20A C25A C24A 0.2(5) . . . . ?
C21A C22A C23A C24A 1.4(6) . . . . ?
C3A O1A C2A C1A -60.8(3) . . . . ?
C3 O1 C2 C1 -61.2(3) . . . . ?
C25A C20A C21A C22A -1.1(5) . . . . ?
C21 C20 C25 C24 -11(3) . . . . ?
C21 C22 C23 C24 -1(3) . . . . ?
C22A C23A C24A C25A -2.3(6) . . . . ?
C25 C20 C21 C22 13(4) . . . . ?
C22 C23 C24 C25 1(2) . . . . ?
C35 C34 C33 C31 -2(2) . . . . ?
C34 C35 C29 C19 171.9(11) . . . . ?
C34 C35 C29 C30 24(3) . . . . ?
C34 C33 C31 C30 2(3) . . . . ?
C33 C31 C30 C29 8(3) . . . . ?
C31 C30 C29 C19 -175.7(16) . . . . ?
C31 C30 C29 C35 -24(3) . . . . ?
C29 C35 C34 C33 -9(2) . . . . ?

_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_P-1_298K
_database_code_depnum_ccdc_archive 'CCDC 2386813'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-02-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   5.4526(2)
_cell_length_b                   13.8271(5)
_cell_length_c                   15.4128(6)
_cell_angle_alpha                94.7690(10)
_cell_angle_beta                 92.4240(10)
_cell_angle_gamma                101.0930(10)
_cell_volume                     1134.35(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9473
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.059
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39855
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_min         1.914
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                   xray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3095
_reflns_number_total             4632
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4632
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.036
_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)+(0.0001P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C25 \\sim C20-C25A
 with sigma of 0.02
 C20-C21 \\sim C20-C21A
 with sigma of 0.02
 C23-C22 \\sim C23A-C22A
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C25-C24 \\sim C25A-C24A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C20-C22 \\sim C20-C22A
 with sigma of 0.04
 C20-C24 \\sim C20-C24A
 with sigma of 0.04
 C23-C25 \\sim C23A-C25A
 with sigma of 0.04
 C23-C21 \\sim C23A-C21A
 with sigma of 0.04
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C20: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C22, C21, C20, C25, C24, C23, C19, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C20, C25A, C24A, C23A, C22A, C21A, C19, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(C22A)=
 Sof(H22A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(C23)=Sof(H23)=Sof(C25)=Sof(H25)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=
 Sof(C24)=Sof(H24)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C19(H19A,H19B), C15(H15A,H15B), C4(H4A,H4B), C1(H1A,H1B),
 C2(H2A,H2B), C3(H3A,H3B), C16(H16A,H16B)
6.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C23(H23), C25(H25), C21(H21), C22(H22), C24(H24),
 C25A(H25A), C24A(H24A), C23A(H23A), C22A(H22A), C21A(H21A)
6.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F1 F 1.0849(3) 0.54041(9) 0.64824(9) 0.0805(4) Uani 1 1 d . . . . .
F2 F 0.9928(3) 0.20987(10) 0.70782(10) 0.0848(4) Uani 1 1 d . . . . .
O2 O 0.3989(3) 0.36968(11) 0.44027(10) 0.0742(5) Uani 1 1 d . . . . .
N2 N 0.5639(3) 0.15456(12) 0.58792(11) 0.0554(4) Uani 1 1 d . . . . .
O3 O -0.0453(3) 0.08264(12) 0.41336(12) 0.0863(6) Uani 1 1 d . . . . .
N3 N 0.0026(4) 0.23736(16) 0.37172(12) 0.0656(5) Uani 1 1 d . . . . .
N1 N 1.2065(3) 0.40759(14) 0.75620(11) 0.0611(5) Uani 1 1 d . . . . .
C9 C 0.7114(4) 0.25036(15) 0.60058(12) 0.0510(5) Uani 1 1 d . . . . .
O1 O 1.5780(4) 0.45283(18) 0.89397(14) 0.1073(7) Uani 1 1 d . . . . .
C10 C 0.9127(4) 0.27929(15) 0.66314(13) 0.0559(5) Uani 1 1 d . . . . .
C8 C 0.6539(4) 0.32327(15) 0.54997(12) 0.0518(5) Uani 1 1 d . . . . .
C17 C 0.4433(4) 0.30315(16) 0.48466(13) 0.0554(5) Uani 1 1 d . . . . .
C16 C 0.2980(4) 0.20388(15) 0.47814(13) 0.0533(5) Uani 1 1 d . . . . .
C15 C 0.3661(4) 0.13706(15) 0.52944(13) 0.0568(5) Uani 1 1 d . . . . .
H18 H 0.267689 0.073728 0.523684 0.068 Uiso 1 1 calc R U . . .
C18 C 0.0701(4) 0.16900(16) 0.41820(14) 0.0599(5) Uani 1 1 d . . . . .
C7 C 0.7919(4) 0.42050(16) 0.56399(13) 0.0589(5) Uani 1 1 d . . . . .
H8 H 0.760054 0.468377 0.528444 0.071 Uiso 1 1 calc R U . . .
C5 C 1.0375(4) 0.37598(16) 0.68377(13) 0.0532(5) Uani 1 1 d . . . . .
C11 C 0.5884(5) 0.07575(16) 0.64531(15) 0.0662(6) Uani 1 1 d . . . . .
H10 H 0.763376 0.071492 0.653087 0.079 Uiso 1 1 calc R U . . .
H9 H 0.497464 0.012578 0.617979 0.079 Uiso 1 1 calc R U . . .
C6 C 0.9716(4) 0.44394(16) 0.62971(14) 0.0584(5) Uani 1 1 d . . . . .
C20 C -0.1327(4) 0.21710(17) 0.21584(15) 0.0651(6) Uani 1 1 d D . . . .
C19 C -0.2090(4) 0.21813(18) 0.30815(14) 0.0673(6) Uani 1 1 d . . . . .
H21 H -0.308570 0.268559 0.318492 0.081 Uiso 1 1 calc R U . . .
H20 H -0.313324 0.154687 0.316235 0.081 Uiso 1 1 calc R U . . .
C12 C 0.4864(5) 0.09685(19) 0.73407(15) 0.0784(7) Uani 1 1 d . . . . .
H11 H 0.534494 0.167205 0.751709 0.094 Uiso 1 1 calc R U . . .
H12 H 0.304965 0.080374 0.728134 0.094 Uiso 1 1 calc R U . . .
C4 C 1.1797(5) 0.3580(2) 0.83492(15) 0.0832(8) Uani 1 1 d . . . . .
H6 H 1.234901 0.295423 0.826156 0.100 Uiso 1 1 calc R U . . .
H7 H 1.004553 0.343994 0.847885 0.100 Uiso 1 1 calc R U . . .
C1 C 1.4622(4) 0.4478(2) 0.74026(17) 0.0846(8) Uani 1 1 d . . . . .
H1 H 1.465195 0.491819 0.694329 0.102 Uiso 1 1 calc R U . . .
H2 H 1.543667 0.394254 0.720192 0.102 Uiso 1 1 calc R U . . .
C2 C 1.6035(5) 0.5029(2) 0.8190(2) 0.0970(9) Uani 1 1 d . . . . .
H3 H 1.779604 0.518142 0.807441 0.116 Uiso 1 1 calc R U . . .
H4 H 1.548223 0.565110 0.830073 0.116 Uiso 1 1 calc R U . . .
C3 C 1.3280(6) 0.4192(3) 0.90952(18) 0.1077(11) Uani 1 1 d . . . . .
H5 H 1.252275 0.475911 0.924450 0.129 Uiso 1 1 calc R U . . .
H3B H 1.320042 0.380633 0.959456 0.129 Uiso 1 1 calc R U . . .
C23 C 0.019(2) 0.2038(11) 0.0452(7) 0.106(3) Uani 0.63(2) 1 d D . P A 1
H24 H 0.066529 0.198309 -0.011933 0.127 Uiso 0.63(2) 1 calc R U P A 1
C13 C 0.5743(7) 0.0416(2) 0.8042(2) 0.1117(11) Uani 1 1 d . . . . .
H14 H 0.755259 0.059594 0.812463 0.134 Uiso 1 1 calc R U . . .
H13 H 0.529616 -0.028883 0.786936 0.134 Uiso 1 1 calc R U . . .
C21 C -0.198(2) 0.2756(7) 0.1560(5) 0.087(2) Uani 0.63(2) 1 d D . P A 1
H22 H -0.294704 0.321515 0.173009 0.104 Uiso 0.63(2) 1 calc R U P A 1
C25 C 0.013(2) 0.1504(10) 0.1871(5) 0.101(3) Uani 0.63(2) 1 d D . P A 1
H26 H 0.059058 0.107483 0.225325 0.121 Uiso 0.63(2) 1 calc R U P A 1
C24 C 0.092(3) 0.1462(11) 0.1038(6) 0.129(4) Uani 0.63(2) 1 d D . P A 1
H25 H 0.197723 0.103217 0.087509 0.155 Uiso 0.63(2) 1 calc R U P A 1
C22 C -0.127(3) 0.2701(9) 0.0705(5) 0.109(3) Uani 0.63(2) 1 d D . P A 1
H23 H -0.176894 0.310936 0.031172 0.131 Uiso 0.63(2) 1 calc R U P A 1
C14 C 0.4567(9) 0.0651(3) 0.8904(2) 0.174(2) Uani 1 1 d . . . . .
H15 H 0.502221 0.134787 0.907760 0.261 Uiso 1 1 calc R U . . .
H16 H 0.516519 0.029072 0.934725 0.261 Uiso 1 1 calc R U . . .
H17 H 0.277744 0.046039 0.882530 0.261 Uiso 1 1 calc R U . . .
H19 H 0.090(5) 0.2931(19) 0.3780(16) 0.088(9) Uiso 1 1 d . . . . .
C21A C -0.297(3) 0.2507(13) 0.1601(8) 0.084(3) Uani 0.37(2) 1 d D . P A 2
H23A H -0.439644 0.270126 0.180498 0.101 Uiso 0.37(2) 1 calc R U P A 2
C22A C -0.244(4) 0.2547(17) 0.0742(9) 0.124(6) Uani 0.37(2) 1 d D . P A 2
H24A H -0.350912 0.278361 0.036467 0.149 Uiso 0.37(2) 1 calc R U P A 2
C23A C -0.041(4) 0.2254(17) 0.0432(10) 0.097(4) Uani 0.37(2) 1 d D . P A 2
H25A H -0.007752 0.229648 -0.015220 0.116 Uiso 0.37(2) 1 calc R U P A 2
C24A C 0.119(4) 0.189(2) 0.0978(9) 0.116(6) Uani 0.37(2) 1 d D . P A 2
H26A H 0.250943 0.163005 0.075864 0.139 Uiso 0.37(2) 1 calc R U P A 2
C25A C 0.078(2) 0.1917(15) 0.1866(8) 0.087(4) Uani 0.37(2) 1 d D . P A 2
H27A H 0.196188 0.175970 0.225536 0.104 Uiso 0.37(2) 1 calc R U P A 2


_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
F1 C6 1.359(2) . ?
F2 C10 1.354(2) . ?
O2 C17 1.245(2) . ?
N2 C9 1.405(2) . ?
N2 C15 1.347(2) . ?
N2 C11 1.481(3) . ?
O3 C18 1.233(2) . ?
N3 C18 1.329(3) . ?
N3 C19 1.451(3) . ?
N3 H19 0.82(3) . ?
N1 C5 1.401(2) . ?
N1 C4 1.442(3) . ?
N1 C1 1.438(3) . ?
C9 C10 1.404(3) . ?
C9 C8 1.398(3) . ?
O1 C2 1.393(3) . ?
O1 C3 1.391(3) . ?
C10 C5 1.383(3) . ?
C8 C17 1.463(3) . ?
C8 C7 1.403(3) . ?
C17 C16 1.440(3) . ?
C16 C15 1.358(3) . ?
C16 C18 1.493(3) . ?
C15 H18 0.9300 . ?
C7 H8 0.9300 . ?
C7 C6 1.353(3) . ?
C5 C6 1.393(3) . ?
C11 H10 0.9700 . ?
C11 H9 0.9700 . ?
C11 C12 1.525(3) . ?
C20 C19 1.499(3) . ?
C20 C21 1.355(6) . ?
C20 C25 1.388(7) . ?
C20 C21A 1.384(10) . ?
C20 C25A 1.350(11) . ?
C19 H21 0.9700 . ?
C19 H20 0.9700 . ?
C12 H11 0.9700 . ?
C12 H12 0.9700 . ?
C12 C13 1.488(3) . ?
C4 H6 0.9700 . ?
C4 H7 0.9700 . ?
C4 C3 1.480(3) . ?
C1 H1 0.9700 . ?
C1 H2 0.9700 . ?
C1 C2 1.480(3) . ?
C2 H3 0.9700 . ?
C2 H4 0.9700 . ?
C3 H5 0.9700 . ?
C3 H3B 0.9700 . ?
C23 H24 0.9300 . ?
C23 C24 1.350(8) . ?
C23 C22 1.367(9) . ?
C13 H14 0.9700 . ?
C13 H13 0.9700 . ?
C13 C14 1.537(5) . ?
C21 H22 0.9300 . ?
C21 C22 1.390(8) . ?
C25 H26 0.9300 . ?
C25 C24 1.371(8) . ?
C24 H25 0.9300 . ?
C22 H23 0.9300 . ?
C14 H15 0.9600 . ?
C14 H16 0.9600 . ?
C14 H17 0.9600 . ?
C21A H23A 0.9300 . ?
C21A C22A 1.370(12) . ?
C22A H24A 0.9300 . ?
C22A C23A 1.343(13) . ?
C23A H25A 0.9300 . ?
C23A C24A 1.375(14) . ?
C24A H26A 0.9300 . ?
C24A C25A 1.393(12) . ?
C25A H27A 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
C9 N2 C11 123.20(17) . . ?
C15 N2 C9 118.70(17) . . ?
C15 N2 C11 117.34(17) . . ?
C18 N3 C19 124.0(2) . . ?
C18 N3 H19 117.5(18) . . ?
C19 N3 H19 118.4(18) . . ?
C5 N1 C4 120.75(18) . . ?
C5 N1 C1 117.77(18) . . ?
C1 N1 C4 113.50(19) . . ?
C10 C9 N2 124.06(19) . . ?
C8 C9 N2 119.03(18) . . ?
C8 C9 C10 116.89(18) . . ?
C3 O1 C2 111.8(2) . . ?
F2 C10 C9 119.40(18) . . ?
F2 C10 C5 116.32(18) . . ?
C5 C10 C9 124.28(19) . . ?
C9 C8 C17 122.05(18) . . ?
C9 C8 C7 120.06(18) . . ?
C7 C8 C17 117.81(19) . . ?
O2 C17 C8 120.28(19) . . ?
O2 C17 C16 124.69(19) . . ?
C16 C17 C8 115.02(19) . . ?
C17 C16 C18 123.68(19) . . ?
C15 C16 C17 119.47(19) . . ?
C15 C16 C18 116.85(19) . . ?
N2 C15 C16 125.67(19) . . ?
N2 C15 H18 117.2 . . ?
C16 C15 H18 117.2 . . ?
O3 C18 N3 123.3(2) . . ?
O3 C18 C16 121.4(2) . . ?
N3 C18 C16 115.28(19) . . ?
C8 C7 H8 120.3 . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 H8 120.3 . . ?
C10 C5 N1 124.3(2) . . ?
C10 C5 C6 114.94(18) . . ?
C6 C5 N1 120.62(19) . . ?
N2 C11 H10 109.4 . . ?
N2 C11 H9 109.4 . . ?
N2 C11 C12 110.98(18) . . ?
H10 C11 H9 108.0 . . ?
C12 C11 H10 109.4 . . ?
C12 C11 H9 109.4 . . ?
F1 C6 C5 117.35(18) . . ?
C7 C6 F1 118.6(2) . . ?
C7 C6 C5 124.0(2) . . ?
C21 C20 C19 125.4(4) . . ?
C21 C20 C25 115.9(5) . . ?
C25 C20 C19 118.7(4) . . ?
C21A C20 C19 113.2(7) . . ?
C25A C20 C19 126.1(6) . . ?
C25A C20 C21A 120.6(9) . . ?
N3 C19 C20 113.1(2) . . ?
N3 C19 H21 109.0 . . ?
N3 C19 H20 109.0 . . ?
C20 C19 H21 109.0 . . ?
C20 C19 H20 109.0 . . ?
H21 C19 H20 107.8 . . ?
C11 C12 H11 108.7 . . ?
C11 C12 H12 108.7 . . ?
H11 C12 H12 107.6 . . ?
C13 C12 C11 114.4(2) . . ?
C13 C12 H11 108.7 . . ?
C13 C12 H12 108.7 . . ?
N1 C4 H6 109.4 . . ?
N1 C4 H7 109.4 . . ?
N1 C4 C3 111.2(2) . . ?
H6 C4 H7 108.0 . . ?
C3 C4 H6 109.4 . . ?
C3 C4 H7 109.4 . . ?
N1 C1 H1 109.1 . . ?
N1 C1 H2 109.1 . . ?
N1 C1 C2 112.3(2) . . ?
H1 C1 H2 107.9 . . ?
C2 C1 H1 109.1 . . ?
C2 C1 H2 109.1 . . ?
O1 C2 C1 114.6(2) . . ?
O1 C2 H3 108.6 . . ?
O1 C2 H4 108.6 . . ?
C1 C2 H3 108.6 . . ?
C1 C2 H4 108.6 . . ?
H3 C2 H4 107.6 . . ?
O1 C3 C4 114.1(3) . . ?
O1 C3 H5 108.7 . . ?
O1 C3 H3B 108.7 . . ?
C4 C3 H5 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H5 C3 H3B 107.6 . . ?
C24 C23 H24 120.3 . . ?
C24 C23 C22 119.5(8) . . ?
C22 C23 H24 120.3 . . ?
C12 C13 H14 109.5 . . ?
C12 C13 H13 109.5 . . ?
C12 C13 C14 110.8(3) . . ?
H14 C13 H13 108.1 . . ?
C14 C13 H14 109.5 . . ?
C14 C13 H13 109.5 . . ?
C20 C21 H22 118.4 . . ?
C20 C21 C22 123.1(7) . . ?
C22 C21 H22 118.4 . . ?
C20 C25 H26 119.1 . . ?
C24 C25 C20 121.8(7) . . ?
C24 C25 H26 119.1 . . ?
C23 C24 C25 120.7(8) . . ?
C23 C24 H25 119.7 . . ?
C25 C24 H25 119.7 . . ?
C23 C22 C21 118.9(7) . . ?
C23 C22 H23 120.5 . . ?
C21 C22 H23 120.5 . . ?
C13 C14 H15 109.5 . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H17 109.5 . . ?
H15 C14 H16 109.5 . . ?
H15 C14 H17 109.5 . . ?
H16 C14 H17 109.5 . . ?
C20 C21A H23A 120.8 . . ?
C22A C21A C20 118.4(11) . . ?
C22A C21A H23A 120.8 . . ?
C21A C22A H24A 119.1 . . ?
C23A C22A C21A 121.7(12) . . ?
C23A C22A H24A 119.1 . . ?
C22A C23A H25A 120.0 . . ?
C22A C23A C24A 120.0(12) . . ?
C24A C23A H25A 120.0 . . ?
C23A C24A H26A 120.5 . . ?
C23A C24A C25A 118.9(12) . . ?
C25A C24A H26A 120.5 . . ?
C20 C25A C24A 119.8(11) . . ?
C20 C25A H27A 120.1 . . ?
C24A C25A H27A 120.1 . . ?

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
F2 C10 C5 N1 -11.5(3) . . . . ?
F2 C10 C5 C6 172.58(18) . . . . ?
O2 C17 C16 C15 179.3(2) . . . . ?
O2 C17 C16 C18 -1.6(3) . . . . ?
N2 C9 C10 F2 8.3(3) . . . . ?
N2 C9 C10 C5 -171.1(2) . . . . ?
N2 C9 C8 C17 0.5(3) . . . . ?
N2 C9 C8 C7 177.28(18) . . . . ?
N2 C11 C12 C13 -161.4(2) . . . . ?
N1 C5 C6 F1 2.6(3) . . . . ?
N1 C5 C6 C7 -173.2(2) . . . . ?
N1 C4 C3 O1 -52.3(4) . . . . ?
N1 C1 C2 O1 48.5(4) . . . . ?
C9 N2 C15 C16 2.2(3) . . . . ?
C9 N2 C11 C12 71.7(3) . . . . ?
C9 C10 C5 N1 167.9(2) . . . . ?
C9 C10 C5 C6 -8.0(3) . . . . ?
C9 C8 C17 O2 -179.4(2) . . . . ?
C9 C8 C17 C16 1.4(3) . . . . ?
C9 C8 C7 C6 -3.4(3) . . . . ?
C10 C9 C8 C17 -177.92(19) . . . . ?
C10 C9 C8 C7 -1.2(3) . . . . ?
C10 C5 C6 F1 178.65(19) . . . . ?
C10 C5 C6 C7 2.9(3) . . . . ?
C8 C9 C10 F2 -173.37(18) . . . . ?
C8 C9 C10 C5 7.2(3) . . . . ?
C8 C17 C16 C15 -1.5(3) . . . . ?
C8 C17 C16 C18 177.62(19) . . . . ?
C8 C7 C6 F1 -173.13(19) . . . . ?
C8 C7 C6 C5 2.5(3) . . . . ?
C17 C8 C7 C6 173.5(2) . . . . ?
C17 C16 C15 N2 -0.2(3) . . . . ?
C17 C16 C18 O3 178.3(2) . . . . ?
C17 C16 C18 N3 -1.9(3) . . . . ?
C15 N2 C9 C10 176.0(2) . . . . ?
C15 N2 C9 C8 -2.3(3) . . . . ?
C15 N2 C11 C12 -98.1(2) . . . . ?
C15 C16 C18 O3 -2.5(3) . . . . ?
C15 C16 C18 N3 177.2(2) . . . . ?
C18 N3 C19 C20 -106.9(3) . . . . ?
C18 C16 C15 N2 -179.4(2) . . . . ?
C7 C8 C17 O2 3.8(3) . . . . ?
C7 C8 C17 C16 -175.47(19) . . . . ?
C5 N1 C4 C3 -163.7(2) . . . . ?
C5 N1 C1 C2 164.2(2) . . . . ?
C11 N2 C9 C10 6.3(3) . . . . ?
C11 N2 C9 C8 -172.01(19) . . . . ?
C11 N2 C15 C16 172.6(2) . . . . ?
C11 C12 C13 C14 -178.4(3) . . . . ?
C20 C21 C22 C23 -0.9(13) . . . . ?
C20 C25 C24 C23 -3.5(18) . . . . ?
C20 C21A C22A C23A 1(2) . . . . ?
C19 N3 C18 O3 -2.0(4) . . . . ?
C19 N3 C18 C16 178.3(2) . . . . ?
C19 C20 C21 C22 -178.5(6) . . . . ?
C19 C20 C25 C24 -179.2(9) . . . . ?
C19 C20 C21A C22A 178.9(12) . . . . ?
C19 C20 C25A C24A 176.5(11) . . . . ?
C4 N1 C5 C10 -29.8(3) . . . . ?
C4 N1 C5 C6 145.9(2) . . . . ?
C4 N1 C1 C2 -46.5(3) . . . . ?
C1 N1 C5 C10 117.1(3) . . . . ?
C1 N1 C5 C6 -67.2(3) . . . . ?
C1 N1 C4 C3 48.1(3) . . . . ?
C2 O1 C3 C4 54.1(4) . . . . ?
C3 O1 C2 C1 -52.0(4) . . . . ?
C21 C20 C19 N3 -122.8(7) . . . . ?
C21 C20 C25 C24 1.7(12) . . . . ?
C25 C20 C19 N3 58.3(8) . . . . ?
C25 C20 C21 C22 0.5(9) . . . . ?
C24 C23 C22 C21 -0.9(17) . . . . ?
C22 C23 C24 C25 3.0(19) . . . . ?
C21A C20 C19 N3 -147.8(9) . . . . ?
C21A C20 C25A C24A -6.9(16) . . . . ?
C21A C22A C23A C24A 1(3) . . . . ?
C22A C23A C24A C25A -6(3) . . . . ?
C23A C24A C25A C20 9(2) . . . . ?
C25A C20 C19 N3 28.9(11) . . . . ?
C25A C20 C21A C22A 1.9(16) . . . . ?

_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_P-1_100K
_database_code_depnum_ccdc_archive 'CCDC 2386889'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   10.6475(4)
_cell_length_b                   13.7206(4)
_cell_length_c                   15.4089(4)
_cell_angle_alpha                84.1320(10)
_cell_angle_beta                 88.4210(10)
_cell_angle_gamma                77.0710(10)
_cell_volume                     2182.50(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ROD
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.9585
_exptl_transmission_factor_min   0.8985
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            54198
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         1.962
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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                   xray
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7638
_reflns_number_total             8935
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     605
_refine_ls_number_reflns         8935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.027
_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)+(0.0507P)²+0.8406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          ?
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F1 F 1.03056(7) 0.52805(5) 0.35547(5) 0.02562(17) Uani 1 1 d . . . . .
N1 N 1.14129(10) 0.39887(8) 0.23855(6) 0.0193(2) Uani 1 1 d . . . . .
O1 O 1.30090(10) 0.44703(8) 0.09823(6) 0.0334(2) Uani 1 1 d . . . . .
C1 C 1.25695(12) 0.43612(10) 0.25378(8) 0.0224(3) Uani 1 1 d . . . . .
H2 H 1.330627 0.378618 0.267378 0.027 Uiso 1 1 calc R U . . .
H1 H 1.242382 0.476429 0.304345 0.027 Uiso 1 1 calc R U . . .
F2 F 1.13054(7) 0.19661(5) 0.28013(5) 0.02487(17) Uani 1 1 d . . . . .
N2 N 0.95501(9) 0.14012(7) 0.41001(6) 0.0169(2) Uani 1 1 d . . . . .
O2 O 0.77500(9) 0.35695(6) 0.56503(5) 0.02210(19) Uani 1 1 d . . . . .
C2 C 1.28793(14) 0.50011(10) 0.17382(9) 0.0290(3) Uani 1 1 d . . . . .
H3 H 1.218434 0.561496 0.164414 0.035 Uiso 1 1 calc R U . . .
H4 H 1.369212 0.521027 0.183422 0.035 Uiso 1 1 calc R U . . .
N3 N 0.63413(10) 0.22852(8) 0.63012(6) 0.0196(2) Uani 1 1 d . . . . .
O3 O 0.68478(9) 0.07074(6) 0.58692(6) 0.0247(2) Uani 1 1 d . . . . .
C3 C 1.18216(14) 0.41923(11) 0.08335(9) 0.0306(3) Uani 1 1 d . . . . .
H6 H 1.188575 0.386348 0.028629 0.037 Uiso 1 1 calc R U . . .
H5 H 1.111652 0.480229 0.076717 0.037 Uiso 1 1 calc R U . . .
C4 C 1.15145(13) 0.34800(10) 0.15869(8) 0.0230(3) Uani 1 1 d . . . . .
H8 H 1.069218 0.329147 0.147788 0.028 Uiso 1 1 calc R U . . .
H7 H 1.220493 0.286030 0.164825 0.028 Uiso 1 1 calc R U . . .
C5 C 1.07988(11) 0.36338(9) 0.31280(8) 0.0176(2) Uani 1 1 d . . . . .
C6 C 1.02012(12) 0.43126(9) 0.37211(8) 0.0193(2) Uani 1 1 d . . . . .
C7 C 0.94526(12) 0.40661(9) 0.43986(8) 0.0192(2) Uani 1 1 d . . . . .
H9 H 0.908860 0.454803 0.478875 0.023 Uiso 1 1 calc R U . . .
C8 C 0.92200(11) 0.30919(9) 0.45185(7) 0.0170(2) Uani 1 1 d . . . . .
C9 C 0.98163(11) 0.23614(9) 0.39727(7) 0.0164(2) Uani 1 1 d . . . . .
C10 C 1.06416(11) 0.26551(9) 0.33122(8) 0.0174(2) Uani 1 1 d . . . . .
C17 C 0.82708(11) 0.28997(9) 0.51849(7) 0.0172(2) Uani 1 1 d . . . . .
C15 C 0.86536(11) 0.12283(9) 0.46966(7) 0.0171(2) Uani 1 1 d . . . . .
H19 H 0.845896 0.058200 0.474857 0.021 Uiso 1 1 calc R U . . .
C16 C 0.80029(11) 0.19087(9) 0.52324(7) 0.0169(2) Uani 1 1 d . . . . .
C11 C 1.00410(11) 0.06086(8) 0.35130(8) 0.0179(2) Uani 1 1 d . . . . .
H10 H 0.994074 -0.004911 0.379980 0.021 Uiso 1 1 calc R U . . .
H11 H 1.097000 0.056684 0.339827 0.021 Uiso 1 1 calc R U . . .
C13 C 1.00278(13) 0.02766(10) 0.19212(8) 0.0237(3) Uani 1 1 d . . . . .
H15 H 1.081035 0.053471 0.176675 0.028 Uiso 1 1 calc R U . . .
H14 H 1.030394 -0.044627 0.212559 0.028 Uiso 1 1 calc R U . . .
C12 C 0.93115(12) 0.08353(9) 0.26529(8) 0.0204(3) Uani 1 1 d . . . . .
H12 H 0.846587 0.065204 0.274178 0.025 Uiso 1 1 calc R U . . .
H13 H 0.914861 0.156663 0.247602 0.025 Uiso 1 1 calc R U . . .
C18 C 0.70174(11) 0.15747(9) 0.58307(7) 0.0178(2) Uani 1 1 d . . . . .
C14 C 0.91940(15) 0.03988(12) 0.11171(9) 0.0348(3) Uani 1 1 d . . . . .
H16 H 0.893997 0.111217 0.090315 0.052 Uiso 1 1 calc R U . . .
H18 H 0.842170 0.013904 0.126692 0.052 Uiso 1 1 calc R U . . .
H17 H 0.968199 0.002397 0.066190 0.052 Uiso 1 1 calc R U . . .
C1A C 0.24044(11) 0.54828(9) 0.73950(8) 0.0209(3) Uani 1 1 d . . . . .
H1A H 0.258884 0.502942 0.692482 0.025 Uiso 1 1 calc R U . . .
H2A H 0.172361 0.607262 0.718743 0.025 Uiso 1 1 calc R U . . .
O1A O 0.17560(9) 0.55381(7) 0.89158(6) 0.0271(2) Uani 1 1 d . . . . .
F1A F 0.48868(7) 0.44626(5) 0.65341(5) 0.02279(16) Uani 1 1 d . . . . .
N1A N 0.35781(9) 0.58158(7) 0.75905(6) 0.0180(2) Uani 1 1 d . . . . .
C19 C 0.53443(11) 0.21144(9) 0.69254(7) 0.0191(2) Uani 1 1 d . . . . .
H22 H 0.512553 0.146496 0.684595 0.023 Uiso 1 1 calc R U . . .
H21 H 0.455857 0.265192 0.681149 0.023 Uiso 1 1 calc R U . . .
C20 C 0.57701(11) 0.20999(9) 0.78564(8) 0.0184(2) Uani 1 1 d . . . . .
C21 C 0.67088(13) 0.13027(10) 0.82253(9) 0.0258(3) Uani 1 1 d . . . . .
H23 H 0.708419 0.076711 0.788946 0.031 Uiso 1 1 calc R U . . .
C22 C 0.71026(13) 0.12819(10) 0.90791(9) 0.0293(3) Uani 1 1 d . . . . .
H24 H 0.774491 0.073386 0.932484 0.035 Uiso 1 1 calc R U . . .
C23 C 0.65596(13) 0.20599(10) 0.95737(8) 0.0268(3) Uani 1 1 d . . . . .
H25 H 0.682173 0.204274 1.016045 0.032 Uiso 1 1 calc R U . . .
C24 C 0.56348(14) 0.28614(10) 0.92102(9) 0.0283(3) Uani 1 1 d . . . . .
H26 H 0.526398 0.339814 0.954597 0.034 Uiso 1 1 calc R U . . .
C25 C 0.52485(13) 0.28809(10) 0.83531(8) 0.0247(3) Uani 1 1 d . . . . .
H27 H 0.461910 0.343644 0.810475 0.030 Uiso 1 1 calc R U . . .
C2A C 0.19328(12) 0.49369(10) 0.82005(8) 0.0248(3) Uani 1 1 d . . . . .
H4A H 0.110596 0.476788 0.806989 0.030 Uiso 1 1 calc R U . . .
H3A H 0.256682 0.430111 0.836210 0.030 Uiso 1 1 calc R U . . .
O2A O 0.73782(9) 0.61701(6) 0.43759(5) 0.02236(19) Uani 1 1 d . . . . .
F2A F 0.35315(7) 0.78516(5) 0.70356(5) 0.02289(16) Uani 1 1 d . . . . .
N2A N 0.54325(9) 0.83804(7) 0.58399(6) 0.0169(2) Uani 1 1 d . . . . .
C3A C 0.29476(13) 0.57773(10) 0.91104(8) 0.0260(3) Uani 1 1 d . . . . .
H5A H 0.360862 0.514936 0.924321 0.031 Uiso 1 1 calc R U . . .
H6A H 0.283867 0.615462 0.963179 0.031 Uiso 1 1 calc R U . . .
O3A O 0.81273(9) 0.90835(7) 0.40742(6) 0.0272(2) Uani 1 1 d . . . . .
N3A N 0.86836(10) 0.75008(8) 0.36608(7) 0.0203(2) Uani 1 1 d . . . . .
C4A C 0.33940(12) 0.64034(9) 0.83459(8) 0.0219(3) Uani 1 1 d . . . . .
H7A H 0.274145 0.703605 0.821209 0.026 Uiso 1 1 calc R U . . .
H8A H 0.421375 0.657521 0.849004 0.026 Uiso 1 1 calc R U . . .
C5A C 0.42392(11) 0.61446(9) 0.68533(7) 0.0168(2) Uani 1 1 d . . . . .
C6A C 0.49420(11) 0.54335(9) 0.63226(8) 0.0178(2) Uani 1 1 d . . . . .
C7A C 0.57064(11) 0.56664(9) 0.56501(7) 0.0180(2) Uani 1 1 d . . . . .
H9A H 0.612625 0.516416 0.529361 0.022 Uiso 1 1 calc R U . . .
C8A C 0.58722(11) 0.66556(9) 0.54849(7) 0.0165(2) Uani 1 1 d . . . . .
C9A C 0.51929(11) 0.74123(8) 0.59798(7) 0.0163(2) Uani 1 1 d . . . . .
C10A C 0.43241(11) 0.71326(9) 0.66138(8) 0.0173(2) Uani 1 1 d . . . . .
C17A C 0.68157(11) 0.68543(9) 0.48170(7) 0.0168(2) Uani 1 1 d . . . . .
C16A C 0.70299(11) 0.78600(9) 0.47392(7) 0.0170(2) Uani 1 1 d . . . . .
C15A C 0.63392(11) 0.85512(9) 0.52523(7) 0.0177(2) Uani 1 1 d . . . . .
H19A H 0.651320 0.920437 0.518901 0.021 Uiso 1 1 calc R U . . .
C11A C 0.49003(12) 0.91819(9) 0.64137(8) 0.0193(2) Uani 1 1 d . . . . .
H11A H 0.395543 0.925769 0.646752 0.023 Uiso 1 1 calc R U . . .
H10A H 0.506979 0.982871 0.614898 0.023 Uiso 1 1 calc R U . . .
C12A C 0.55086(12) 0.89291(9) 0.73181(8) 0.0214(3) Uani 1 1 d . . . . .
H12A H 0.563644 0.819694 0.748149 0.026 Uiso 1 1 calc R U . . .
H13A H 0.636725 0.909630 0.729278 0.026 Uiso 1 1 calc R U . . .
C13A C 0.47041(13) 0.94852(10) 0.80227(8) 0.0269(3) Uani 1 1 d . . . . .
H14A H 0.461125 1.021767 0.787891 0.032 Uiso 1 1 calc R U . . .
H15A H 0.383222 0.934237 0.803563 0.032 Uiso 1 1 calc R U . . .
C14A C 0.53149(17) 0.91760(12) 0.89181(9) 0.0389(4) Uani 1 1 d . . . . .
H16A H 0.541129 0.845066 0.906139 0.058 Uiso 1 1 calc R U . . .
H17A H 0.476328 0.953613 0.935584 0.058 Uiso 1 1 calc R U . . .
H18A H 0.616376 0.934209 0.891418 0.058 Uiso 1 1 calc R U . . .
C18A C 0.79953(12) 0.82068(9) 0.41295(8) 0.0191(2) Uani 1 1 d . . . . .
C19A C 0.96533(12) 0.76921(9) 0.30289(8) 0.0215(3) Uani 1 1 d . . . . .
H22A H 1.043460 0.714507 0.311861 0.026 Uiso 1 1 calc R U . . .
H21A H 0.989005 0.832773 0.313414 0.026 Uiso 1 1 calc R U . . .
C20A C 0.92229(12) 0.77661(9) 0.20918(8) 0.0212(3) Uani 1 1 d . . . . .
C21A C 0.79360(13) 0.80622(11) 0.18544(9) 0.0281(3) Uani 1 1 d . . . . .
H23A H 0.729413 0.819713 0.229339 0.034 Uiso 1 1 calc R U . . .
C22A C 0.75705(15) 0.81644(12) 0.09867(9) 0.0353(3) Uani 1 1 d . . . . .
H24A H 0.668558 0.837326 0.083453 0.042 Uiso 1 1 calc R U . . .
C23A C 0.84981(17) 0.79616(12) 0.03436(9) 0.0373(4) Uani 1 1 d . . . . .
H25A H 0.825260 0.803550 -0.025174 0.045 Uiso 1 1 calc R U . . .
C24A C 0.97841(16) 0.76507(11) 0.05704(9) 0.0373(4) Uani 1 1 d . . . . .
H26A H 1.042075 0.749911 0.013065 0.045 Uiso 1 1 calc R U . . .
C25A C 1.01480(14) 0.75593(10) 0.14397(9) 0.0289(3) Uani 1 1 d . . . . .
H27A H 1.103397 0.735434 0.158993 0.035 Uiso 1 1 calc R U . . .
H20 H 0.6560(15) 0.2876(13) 0.6236(10) 0.031(4) Uiso 1 1 d . . . . .
H20A H 0.8532(16) 0.6907(13) 0.3740(11) 0.038(5) Uiso 1 1 d . . . . .


_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
F1 C6 1.3552(13) . ?
N1 C1 1.4680(15) . ?
N1 C4 1.4655(16) . ?
N1 C5 1.4003(15) . ?
O1 C2 1.4231(17) . ?
O1 C3 1.4304(17) . ?
C1 H2 0.9900 . ?
C1 H1 0.9900 . ?
C1 C2 1.5112(17) . ?
F2 C10 1.3549(13) . ?
N2 C9 1.4020(15) . ?
N2 C15 1.3494(15) . ?
N2 C11 1.4816(14) . ?
O2 C17 1.2455(14) . ?
C2 H3 0.9900 . ?
C2 H4 0.9900 . ?
N3 H3N 0.887(17) . ?
N3 C18 1.3402(15) . ?
N3 C19 1.4546(15) . ?
O3 C18 1.2382(14) . ?
C3 H6 0.9900 . ?
C3 H5 0.9900 . ?
C3 C4 1.5165(17) . ?
C4 H8 0.9900 . ?
C4 H7 0.9900 . ?
C5 C6 1.4086(17) . ?
C5 C10 1.3899(16) . ?
C6 C7 1.3573(17) . ?
C7 H9 0.9500 . ?
C7 C8 1.4062(16) . ?
C8 C9 1.4047(16) . ?
C8 C17 1.4670(16) . ?
C9 C10 1.4126(16) . ?
C17 C16 1.4449(16) . ?
C15 H19 0.9500 . ?
C15 C16 1.3673(16) . ?
C16 C18 1.4955(16) . ?
C11 H10 0.9900 . ?
C11 H11 0.9900 . ?
C11 C12 1.5233(16) . ?
C13 H15 0.9900 . ?
C13 H14 0.9900 . ?
C13 C12 1.5193(16) . ?
C13 C14 1.5176(19) . ?
C12 H12 0.9900 . ?
C12 H13 0.9900 . ?
C14 H16 0.9800 . ?
C14 H18 0.9800 . ?
C14 H17 0.9800 . ?
C1A H1A 0.9900 . ?
C1A H2A 0.9900 . ?
C1A N1A 1.4717(15) . ?
C1A C2A 1.5157(17) . ?
O1A C2A 1.4267(16) . ?
O1A C3A 1.4264(16) . ?
F1A C6A 1.3525(13) . ?
N1A C4A 1.4669(15) . ?
N1A C5A 1.4081(15) . ?
C19 H22 0.9900 . ?
C19 H21 0.9900 . ?
C19 C20 1.5132(16) . ?
C20 C21 1.3905(18) . ?
C20 C25 1.3858(17) . ?
C21 H23 0.9500 . ?
C21 C22 1.3873(18) . ?
C22 H24 0.9500 . ?
C22 C23 1.3859(19) . ?
C23 H25 0.9500 . ?
C23 C24 1.3829(19) . ?
C24 H26 0.9500 . ?
C24 C25 1.3899(18) . ?
C25 H27 0.9500 . ?
C2A H4A 0.9900 . ?
C2A H3A 0.9900 . ?
O2A C17A 1.2485(14) . ?
F2A C10A 1.3551(13) . ?
N2A C9A 1.4022(15) . ?
N2A C15A 1.3477(15) . ?
N2A C11A 1.4847(15) . ?
C3A H5A 0.9900 . ?
C3A H6A 0.9900 . ?
C3A C4A 1.5154(17) . ?
O3A C18A 1.2361(15) . ?
N3A H3NA 0.861(18) . ?
N3A C18A 1.3391(16) . ?
N3A C19A 1.4480(15) . ?
C4A H7A 0.9900 . ?
C4A H8A 0.9900 . ?
C5A C6A 1.4084(17) . ?
C5A C10A 1.3901(16) . ?
C6A C7A 1.3567(16) . ?
C7A H9A 0.9500 . ?
C7A C8A 1.4043(16) . ?
C8A C9A 1.4065(16) . ?
C8A C17A 1.4666(16) . ?
C9A C10A 1.4107(16) . ?
C17A C16A 1.4408(16) . ?
C16A C15A 1.3691(17) . ?
C16A C18A 1.4967(16) . ?
C15A H19A 0.9500 . ?
C11A H11A 0.9900 . ?
C11A H10A 0.9900 . ?
C11A C12A 1.5273(17) . ?
C12A H12A 0.9900 . ?
C12A H13A 0.9900 . ?
C12A C13A 1.5233(17) . ?
C13A H14A 0.9900 . ?
C13A H15A 0.9900 . ?
C13A C14A 1.521(2) . ?
C14A H16A 0.9800 . ?
C14A H17A 0.9800 . ?
C14A H18A 0.9800 . ?
C19A H22A 0.9900 . ?
C19A H21A 0.9900 . ?
C19A C20A 1.5136(17) . ?
C20A C21A 1.3873(19) . ?
C20A C25A 1.3924(18) . ?
C21A H23A 0.9500 . ?
C21A C22A 1.3872(19) . ?
C22A H24A 0.9500 . ?
C22A C23A 1.384(2) . ?
C23A H25A 0.9500 . ?
C23A C24A 1.383(2) . ?
C24A H26A 0.9500 . ?
C24A C25A 1.390(2) . ?
C25A H27A 0.9500 . ?

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
C4 N1 C1 112.24(10) . . ?
C5 N1 C1 116.34(9) . . ?
C5 N1 C4 120.55(10) . . ?
C2 O1 C3 109.12(10) . . ?
N1 C1 H2 109.6 . . ?
N1 C1 H1 109.6 . . ?
N1 C1 C2 110.10(10) . . ?
H2 C1 H1 108.2 . . ?
C2 C1 H2 109.6 . . ?
C2 C1 H1 109.6 . . ?
C9 N2 C11 123.02(9) . . ?
C15 N2 C9 119.07(10) . . ?
C15 N2 C11 117.11(9) . . ?
O1 C2 C1 111.45(11) . . ?
O1 C2 H3 109.3 . . ?
O1 C2 H4 109.3 . . ?
C1 C2 H3 109.3 . . ?
C1 C2 H4 109.3 . . ?
H3 C2 H4 108.0 . . ?
C18 N3 C19 123.56(10) . . ?
O1 C3 H6 109.5 . . ?
O1 C3 H5 109.5 . . ?
O1 C3 C4 110.61(11) . . ?
H6 C3 H5 108.1 . . ?
C4 C3 H6 109.5 . . ?
C4 C3 H5 109.5 . . ?
N1 C4 C3 108.35(10) . . ?
N1 C4 H8 110.0 . . ?
N1 C4 H7 110.0 . . ?
C3 C4 H8 110.0 . . ?
C3 C4 H7 110.0 . . ?
H8 C4 H7 108.4 . . ?
N1 C5 C6 119.39(10) . . ?
C10 C5 N1 125.18(11) . . ?
C10 C5 C6 115.27(10) . . ?
F1 C6 C5 117.21(10) . . ?
F1 C6 C7 118.97(11) . . ?
C7 C6 C5 123.60(11) . . ?
C6 C7 H9 120.3 . . ?
C6 C7 C8 119.48(11) . . ?
C8 C7 H9 120.3 . . ?
C7 C8 C17 117.48(11) . . ?
C9 C8 C7 120.34(11) . . ?
C9 C8 C17 122.03(10) . . ?
N2 C9 C8 119.00(10) . . ?
N2 C9 C10 123.96(10) . . ?
C8 C9 C10 117.03(10) . . ?
F2 C10 C5 116.51(10) . . ?
F2 C10 C9 119.63(10) . . ?
C5 C10 C9 123.84(11) . . ?
O2 C17 C8 120.26(10) . . ?
O2 C17 C16 124.86(11) . . ?
C16 C17 C8 114.87(10) . . ?
N2 C15 H19 117.4 . . ?
N2 C15 C16 125.24(11) . . ?
C16 C15 H19 117.4 . . ?
C18 N3 H3N 116.3(10) . . ?
C17 C16 C18 123.65(10) . . ?
C15 C16 C17 119.60(10) . . ?
C15 C16 C18 116.74(10) . . ?
N2 C11 H10 109.5 . . ?
N2 C11 H11 109.5 . . ?
N2 C11 C12 110.73(9) . . ?
H10 C11 H11 108.1 . . ?
C12 C11 H10 109.5 . . ?
C12 C11 H11 109.5 . . ?
H15 C13 H14 107.9 . . ?
C12 C13 H15 109.3 . . ?
C12 C13 H14 109.3 . . ?
C14 C13 H15 109.3 . . ?
C14 C13 H14 109.3 . . ?
C14 C13 C12 111.68(11) . . ?
C11 C12 H12 108.9 . . ?
C11 C12 H13 108.9 . . ?
C13 C12 C11 113.26(10) . . ?
C13 C12 H12 108.9 . . ?
C13 C12 H13 108.9 . . ?
H12 C12 H13 107.7 . . ?
N3 C18 C16 114.80(10) . . ?
O3 C18 N3 123.75(11) . . ?
O3 C18 C16 121.45(11) . . ?
C13 C14 H16 109.5 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H17 109.5 . . ?
H16 C14 H18 109.5 . . ?
H16 C14 H17 109.5 . . ?
H18 C14 H17 109.5 . . ?
H1A C1A H2A 108.1 . . ?
N1A C1A H1A 109.5 . . ?
N1A C1A H2A 109.5 . . ?
N1A C1A C2A 110.55(10) . . ?
C19 N3 H3N 120.1(10) . . ?
C2A C1A H1A 109.5 . . ?
C2A C1A H2A 109.5 . . ?
C3A O1A C2A 109.58(9) . . ?
C4A N1A C1A 111.67(9) . . ?
C5A N1A C1A 114.80(9) . . ?
C5A N1A C4A 118.97(9) . . ?
N3 C19 H22 109.3 . . ?
N3 C19 H21 109.3 . . ?
N3 C19 C20 111.81(10) . . ?
H22 C19 H21 107.9 . . ?
C20 C19 H22 109.3 . . ?
C20 C19 H21 109.3 . . ?
C21 C20 C19 120.25(11) . . ?
C25 C20 C19 120.97(11) . . ?
C25 C20 C21 118.77(11) . . ?
C20 C21 H23 119.7 . . ?
C22 C21 C20 120.64(12) . . ?
C22 C21 H23 119.7 . . ?
C21 C22 H24 120.0 . . ?
C23 C22 C21 120.05(12) . . ?
C23 C22 H24 120.0 . . ?
C22 C23 H25 120.1 . . ?
C24 C23 C22 119.77(12) . . ?
C24 C23 H25 120.1 . . ?
C23 C24 H26 120.0 . . ?
C23 C24 C25 119.94(12) . . ?
C25 C24 H26 120.0 . . ?
C20 C25 C24 120.82(12) . . ?
C20 C25 H27 119.6 . . ?
C24 C25 H27 119.6 . . ?
C1A C2A H4A 109.4 . . ?
C1A C2A H3A 109.4 . . ?
O1A C2A C1A 111.21(10) . . ?
O1A C2A H4A 109.4 . . ?
O1A C2A H3A 109.4 . . ?
H4A C2A H3A 108.0 . . ?
C9A N2A C11A 122.73(9) . . ?
C15A N2A C9A 118.88(10) . . ?
C15A N2A C11A 117.54(9) . . ?
O1A C3A H5A 109.5 . . ?
O1A C3A H6A 109.5 . . ?
O1A C3A C4A 110.59(10) . . ?
H5A C3A H6A 108.1 . . ?
C4A C3A H5A 109.5 . . ?
C4A C3A H6A 109.5 . . ?
C18A N3A C19A 123.20(10) . . ?
N1A C4A C3A 108.27(10) . . ?
N1A C4A H7A 110.0 . . ?
N1A C4A H8A 110.0 . . ?
C3A C4A H7A 110.0 . . ?
C3A C4A H8A 110.0 . . ?
H7A C4A H8A 108.4 . . ?
N1A C5A C6A 119.41(10) . . ?
C10A C5A N1A 125.35(11) . . ?
C10A C5A C6A 115.15(10) . . ?
F1A C6A C5A 117.04(10) . . ?
F1A C6A C7A 119.28(10) . . ?
C7A C6A C5A 123.60(11) . . ?
C6A C7A H9A 120.2 . . ?
C6A C7A C8A 119.50(11) . . ?
C8A C7A H9A 120.2 . . ?
C7A C8A C9A 120.29(10) . . ?
C7A C8A C17A 117.89(10) . . ?
C9A C8A C17A 121.75(10) . . ?
N2A C9A C8A 119.30(10) . . ?
N2A C9A C10A 123.78(10) . . ?
C8A C9A C10A 116.90(10) . . ?
F2A C10A C5A 116.76(10) . . ?
F2A C10A C9A 119.42(10) . . ?
C5A C10A C9A 123.81(11) . . ?
O2A C17A C8A 119.97(10) . . ?
O2A C17A C16A 124.97(11) . . ?
C16A C17A C8A 115.05(10) . . ?
C17A C16A C18A 123.73(11) . . ?
C15A C16A C17A 119.61(10) . . ?
C15A C16A C18A 116.65(10) . . ?
N2A C15A C16A 125.32(11) . . ?
N2A C15A H19A 117.3 . . ?
C16A C15A H19A 117.3 . . ?
N2A C11A H11A 109.5 . . ?
N2A C11A H10A 109.5 . . ?
N2A C11A C12A 110.83(9) . . ?
H11A C11A H10A 108.1 . . ?
C12A C11A H11A 109.5 . . ?
C12A C11A H10A 109.5 . . ?
C11A C12A H12A 108.9 . . ?
C11A C12A H13A 108.9 . . ?
H12A C12A H13A 107.7 . . ?
C13A C12A C11A 113.49(10) . . ?
C13A C12A H12A 108.9 . . ?
C13A C12A H13A 108.9 . . ?
C12A C13A H14A 109.3 . . ?
C12A C13A H15A 109.3 . . ?
H14A C13A H15A 107.9 . . ?
C14A C13A C12A 111.71(12) . . ?
C14A C13A H14A 109.3 . . ?
C14A C13A H15A 109.3 . . ?
C13A C14A H16A 109.5 . . ?
C13A C14A H17A 109.5 . . ?
C13A C14A H18A 109.5 . . ?
H16A C14A H17A 109.5 . . ?
H16A C14A H18A 109.5 . . ?
H17A C14A H18A 109.5 . . ?
O3A C18A N3A 123.72(11) . . ?
C18A N3A H3NA 117.8(11) . . ?
C19A N3A H3NA 119.0(11) . . ?
O3A C18A C16A 121.35(11) . . ?
N3A C18A C16A 114.93(10) . . ?
N3A C19A H22A 108.8 . . ?
N3A C19A H21A 108.8 . . ?
N3A C19A C20A 113.63(10) . . ?
H22A C19A H21A 107.7 . . ?
C20A C19A H22A 108.8 . . ?
C20A C19A H21A 108.8 . . ?
C21A C20A C19A 122.24(11) . . ?
C21A C20A C25A 118.57(12) . . ?
C25A C20A C19A 119.16(12) . . ?
C20A C21A H23A 119.4 . . ?
C22A C21A C20A 121.12(13) . . ?
C22A C21A H23A 119.4 . . ?
C21A C22A H24A 120.1 . . ?
C23A C22A C21A 119.83(14) . . ?
C23A C22A H24A 120.1 . . ?
C22A C23A H25A 120.1 . . ?
C24A C23A C22A 119.78(13) . . ?
C24A C23A H25A 120.1 . . ?
C23A C24A H26A 119.9 . . ?
C23A C24A C25A 120.23(13) . . ?
C25A C24A H26A 119.9 . . ?
C20A C25A H27A 119.8 . . ?
C24A C25A C20A 120.45(14) . . ?
C24A C25A H27A 119.8 . . ?

####################################################################### 
# 
# 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_P-1_150K
_database_code_depnum_ccdc_archive 'CCDC 2386811'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   10.6998(3)
_cell_length_b                   13.7430(4)
_cell_length_c                   15.4384(4)
_cell_angle_alpha                84.1400(10)
_cell_angle_beta                 88.1650(10)
_cell_angle_gamma                77.5590(10)
_cell_volume                     2205.17(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7195
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0902 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.9653.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43541
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         1.949
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_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                   xray
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6161
_reflns_number_total             9042
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0863
_refine_ls_restrained_S_all      1.110
_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)+(0.1437P)²+2.5206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C012(H01A,H01B), C013(H01Y,H), C014(H01Z,HA), C015(H01C,H01D), C017(H01E,
 H01F), C018(H01,HB), C019(H01G,H01H), C01A(H0AA,HC), C01B(H01I,H01J),
 C01C(H1AA,HD), C01D(H2AA,HE), C01F(H01K,H01L), C01G(H01M,H01N), C01I(H01O,
 H01P), C01K(H6AA,HF), C01M(H8AA,HG)
2.b Aromatic/amide H refined with riding coordinates:
 N00E(H00E), N00F(H00F), C00L(H00L), C00N(H00N), C00O(H00O), C00U(H00U),
 C01E(H3AA), C01H(H4AA), C01J(H5AA), C01L(H7AA), C01N(H01Q), C01O(H01R),
 C01P(H9AA), C01Q(H01S), C01R(H01T), C01S(H01U)
2.c Idealised Me refined as rotating group:
 C01T(H0BA,HH,HI), C01U(H01V,H01W,H01X)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F1 F 0.48544(18) 0.44833(12) 0.65350(12) 0.0436(4) Uani 1 1 d . . . . .
F2 F 0.35381(17) 0.78542(12) 0.70545(12) 0.0437(5) Uani 1 1 d . . . . .
F1A F 1.02848(19) 0.53118(13) 0.35383(12) 0.0467(5) Uani 1 1 d . . . . .
F2A F 1.13374(17) 0.19892(13) 0.28374(12) 0.0463(5) Uani 1 1 d . . . . .
O2A O 0.7718(2) 0.35992(15) 0.56403(14) 0.0419(5) Uani 1 1 d . . . . .
O2 O 0.7359(2) 0.61996(15) 0.43852(13) 0.0413(5) Uani 1 1 d . . . . .
O3A O 0.6854(2) 0.07230(16) 0.58851(15) 0.0458(6) Uani 1 1 d . . . . .
O3 O 0.8117(2) 0.91062(16) 0.40856(16) 0.0490(6) Uani 1 1 d . . . . .
O1 O 0.1761(2) 0.55336(18) 0.89324(15) 0.0494(6) Uani 1 1 d . . . . .
N2 N 0.5424(2) 0.83941(17) 0.58529(15) 0.0328(5) Uani 1 1 d . . . . .
N2A N 0.9549(2) 0.14292(17) 0.41106(15) 0.0329(5) Uani 1 1 d . . . . .
O1A O 1.3064(3) 0.4455(2) 0.10005(16) 0.0571(7) Uani 1 1 d . . . . .
N1 N 0.3554(2) 0.58318(18) 0.75969(15) 0.0347(5) Uani 1 1 d . . . . .
N3 N 0.8677(2) 0.75272(18) 0.36779(15) 0.0379(6) Uani 1 1 d . . . . .
H20 H 0.853748 0.691640 0.376056 0.045 Uiso 1 1 calc R . . . .
N3A N 0.6329(2) 0.23039(18) 0.63024(15) 0.0368(6) Uani 1 1 d . . . . .
H20A H 0.648905 0.290889 0.622452 0.044 Uiso 1 1 calc R . . . .
N1A N 1.1433(2) 0.40082(19) 0.23929(15) 0.0367(5) Uani 1 1 d . . . . .
C8 C 0.5855(3) 0.6677(2) 0.54917(17) 0.0312(6) Uani 1 1 d . . . . .
C9A C 0.9810(3) 0.2392(2) 0.39819(17) 0.0309(6) Uani 1 1 d . . . . .
C9 C 0.5188(3) 0.7428(2) 0.59913(17) 0.0309(6) Uani 1 1 d . . . . .
C8A C 0.9196(3) 0.3123(2) 0.45139(17) 0.0324(6) Uani 1 1 d . . . . .
C15A C 0.8648(3) 0.1256(2) 0.47063(18) 0.0335(6) Uani 1 1 d . . . . .
H19A H 0.845365 0.060981 0.476044 0.040 Uiso 1 1 calc R . . . .
C10A C 1.0654(3) 0.2682(2) 0.33283(18) 0.0329(6) Uani 1 1 d . . . . .
C15 C 0.6332(3) 0.8568(2) 0.52622(18) 0.0338(6) Uani 1 1 d . . . . .
H19 H 0.650984 0.921965 0.519802 0.041 Uiso 1 1 calc R . . . .
C7 C 0.5683(3) 0.5687(2) 0.56542(18) 0.0349(6) Uani 1 1 d . . . . .
H9 H 0.609798 0.518805 0.529705 0.042 Uiso 1 1 calc R . . . .
C16 C 0.7015(3) 0.7879(2) 0.47499(17) 0.0325(6) Uani 1 1 d . . . . .
C20A C 0.5768(3) 0.2110(2) 0.78547(19) 0.0376(6) Uani 1 1 d . . . . .
C17 C 0.6799(3) 0.6879(2) 0.48286(17) 0.0323(6) Uani 1 1 d . . . . .
C10 C 0.4322(3) 0.7141(2) 0.66274(18) 0.0332(6) Uani 1 1 d . . . . .
C16A C 0.7995(3) 0.1933(2) 0.52356(17) 0.0336(6) Uani 1 1 d . . . . .
C7A C 0.9421(3) 0.4101(2) 0.43878(18) 0.0363(6) Uani 1 1 d . . . . .
H9A H 0.904240 0.458485 0.476938 0.044 Uiso 1 1 calc R . . . .
C17A C 0.8248(3) 0.2927(2) 0.51776(17) 0.0337(6) Uani 1 1 d . . . . .
C5 C 0.4218(3) 0.6160(2) 0.68593(18) 0.0322(6) Uani 1 1 d . . . . .
C6 C 0.4916(3) 0.5454(2) 0.63272(18) 0.0340(6) Uani 1 1 d . . . . .
C18A C 0.7009(3) 0.1596(2) 0.58362(18) 0.0355(6) Uani 1 1 d . . . . .
C5A C 1.0803(3) 0.3663(2) 0.31352(18) 0.0332(6) Uani 1 1 d . . . . .
C18 C 0.7984(3) 0.8227(2) 0.41415(18) 0.0357(6) Uani 1 1 d . . . . .
C20 C 0.9231(3) 0.7781(2) 0.2118(2) 0.0398(7) Uani 1 1 d . . . . .
C1 C 0.2388(3) 0.5495(2) 0.7410(2) 0.0381(6) Uani 1 1 d . . . . .
H1 H 0.256589 0.504825 0.693635 0.046 Uiso 1 1 calc R . . . .
H2 H 0.171203 0.608145 0.720993 0.046 Uiso 1 1 calc R . . . .
C11A C 1.0039(3) 0.0643(2) 0.35235(18) 0.0362(6) Uani 1 1 d . . . . .
H10A H 0.992726 -0.001268 0.380526 0.043 Uiso 1 1 calc R . . . .
H11A H 1.096559 0.060189 0.341507 0.043 Uiso 1 1 calc R . . . .
C19A C 0.5339(3) 0.2122(2) 0.69319(18) 0.0372(6) Uani 1 1 d . . . . .
H22A H 0.512363 0.147202 0.685316 0.045 Uiso 1 1 calc R . . . .
H21A H 0.455753 0.265253 0.682372 0.045 Uiso 1 1 calc R . . . .
C11 C 0.4901(3) 0.9188(2) 0.64253(19) 0.0367(6) Uani 1 1 d . . . . .
H11 H 0.396371 0.925264 0.649028 0.044 Uiso 1 1 calc R . . . .
H10 H 0.506043 0.983654 0.615686 0.044 Uiso 1 1 calc R . . . .
C6A C 1.0186(3) 0.4347(2) 0.37135(19) 0.0371(6) Uani 1 1 d . . . . .
C12 C 0.5525(3) 0.8942(2) 0.73254(19) 0.0415(7) Uani 1 1 d . . . . .
H12 H 0.565609 0.821232 0.748945 0.050 Uiso 1 1 calc R . . . .
H13 H 0.637699 0.911691 0.728794 0.050 Uiso 1 1 calc R . . . .
C12A C 0.9330(3) 0.0874(2) 0.26564(19) 0.0400(7) Uani 1 1 d . . . . .
H13A H 0.848360 0.069362 0.273849 0.048 Uiso 1 1 calc R . . . .
H12A H 0.918142 0.160281 0.248175 0.048 Uiso 1 1 calc R . . . .
C4 C 0.3389(3) 0.6407(2) 0.83568(19) 0.0403(7) Uani 1 1 d . . . . .
H7 H 0.274321 0.703719 0.823361 0.048 Uiso 1 1 calc R . . . .
H8 H 0.420805 0.657856 0.849375 0.048 Uiso 1 1 calc R . . . .
C4A C 1.1544(3) 0.3490(2) 0.16007(19) 0.0432(7) Uani 1 1 d . . . . .
H7A H 1.072436 0.330486 0.148706 0.052 Uiso 1 1 calc R . . . .
H8A H 1.221885 0.286956 0.167180 0.052 Uiso 1 1 calc R . . . .
C19 C 0.9648(3) 0.7721(2) 0.30464(19) 0.0404(7) Uani 1 1 d . . . . .
H21 H 1.042394 0.718129 0.313904 0.048 Uiso 1 1 calc R . . . .
H22 H 0.987984 0.835907 0.314710 0.048 Uiso 1 1 calc R . . . .
C1A C 1.2585(3) 0.4378(2) 0.2552(2) 0.0412(7) Uani 1 1 d . . . . .
H2A H 1.330434 0.380532 0.270298 0.049 Uiso 1 1 calc R . . . .
H1A H 1.242934 0.479334 0.304773 0.049 Uiso 1 1 calc R . . . .
C13A C 1.0049(3) 0.0318(2) 0.1929(2) 0.0474(8) Uani 1 1 d . . . . .
H15A H 1.027501 -0.040776 0.212046 0.057 Uiso 1 1 calc R . . . .
H14A H 1.085411 0.055109 0.179709 0.057 Uiso 1 1 calc R . . . .
C25A C 0.5204(4) 0.2847(3) 0.8372(2) 0.0509(8) Uani 1 1 d . . . . .
H27A H 0.454102 0.337754 0.814065 0.061 Uiso 1 1 calc R . . . .
C2 C 0.1923(3) 0.4942(3) 0.8213(2) 0.0472(8) Uani 1 1 d . . . . .
H4 H 0.109684 0.477356 0.808680 0.057 Uiso 1 1 calc R . . . .
H3 H 0.254898 0.430795 0.836528 0.057 Uiso 1 1 calc R . . . .
C13 C 0.4740(4) 0.9492(3) 0.8038(2) 0.0507(8) Uani 1 1 d . . . . .
H14 H 0.464341 1.022260 0.789463 0.061 Uiso 1 1 calc R . . . .
H15 H 0.387493 0.934032 0.806587 0.061 Uiso 1 1 calc R . . . .
C23A C 0.6539(4) 0.2069(3) 0.9570(2) 0.0517(8) Uani 1 1 d . . . . .
H25A H 0.679612 0.204999 1.015625 0.062 Uiso 1 1 calc R . . . .
C3 C 0.2952(3) 0.5776(3) 0.9120(2) 0.0477(8) Uani 1 1 d . . . . .
H5 H 0.360731 0.515221 0.924526 0.057 Uiso 1 1 calc R . . . .
H6 H 0.285088 0.614830 0.964343 0.057 Uiso 1 1 calc R . . . .
C21A C 0.6736(4) 0.1353(3) 0.8206(2) 0.0550(9) Uani 1 1 d . . . . .
H23A H 0.714193 0.084045 0.785791 0.066 Uiso 1 1 calc R . . . .
C2A C 1.2930(3) 0.4996(3) 0.1746(2) 0.0503(8) Uani 1 1 d . . . . .
H3A H 1.225478 0.561173 0.164089 0.060 Uiso 1 1 calc R . . . .
H4A H 1.374321 0.519898 0.184529 0.060 Uiso 1 1 calc R . . . .
C22A C 0.7127(4) 0.1327(3) 0.9058(2) 0.0596(10) Uani 1 1 d . . . . .
H24A H 0.779604 0.080211 0.928940 0.072 Uiso 1 1 calc R . . . .
C3A C 1.1882(4) 0.4185(3) 0.0849(2) 0.0527(8) Uani 1 1 d . . . . .
H6A H 1.194938 0.384996 0.030634 0.063 Uiso 1 1 calc R . . . .
H5A H 1.119338 0.479564 0.077478 0.063 Uiso 1 1 calc R . . . .
C25 C 1.0136(4) 0.7513(3) 0.1478(2) 0.0596(10) Uani 1 1 d . . . . .
H27 H 1.100966 0.727829 0.163049 0.071 Uiso 1 1 calc R . . . .
C21 C 0.7973(4) 0.8121(3) 0.1864(2) 0.0592(9) Uani 1 1 d . . . . .
H23 H 0.733496 0.829852 0.229601 0.071 Uiso 1 1 calc R . . . .
C24A C 0.5587(4) 0.2829(3) 0.9230(2) 0.0579(9) Uani 1 1 d . . . . .
H26A H 0.518680 0.334412 0.957671 0.069 Uiso 1 1 calc R . . . .
C23 C 0.8517(5) 0.7948(3) 0.0375(2) 0.0633(10) Uani 1 1 d . . . . .
H25 H 0.827824 0.801473 -0.021876 0.076 Uiso 1 1 calc R . . . .
C22 C 0.7613(4) 0.8211(4) 0.1003(3) 0.0703(11) Uani 1 1 d . . . . .
H24 H 0.674096 0.845542 0.084813 0.084 Uiso 1 1 calc R . . . .
C24 C 0.9771(5) 0.7587(3) 0.0605(3) 0.0737(13) Uani 1 1 d . . . . .
H26 H 1.039629 0.738505 0.017089 0.088 Uiso 1 1 calc R . . . .
C14A C 0.9242(5) 0.0489(4) 0.1110(2) 0.0716(12) Uani 1 1 d . . . . .
H18A H 0.842935 0.028591 0.124645 0.107 Uiso 1 1 calc GR . . . .
H17A H 0.970495 0.009173 0.066218 0.107 Uiso 1 1 calc GR . . . .
H16A H 0.907387 0.120077 0.089501 0.107 Uiso 1 1 calc GR . . . .
C14 C 0.5375(5) 0.9184(3) 0.8917(3) 0.0732(12) Uani 1 1 d . . . . .
H16 H 0.550307 0.845688 0.904910 0.110 Uiso 1 1 calc GR . . . .
H17 H 0.482818 0.951828 0.936771 0.110 Uiso 1 1 calc GR . . . .
H18 H 0.620535 0.937862 0.890319 0.110 Uiso 1 1 calc GR . . . .


_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
F1 C6 1.355(3) . ?
F2 C10 1.357(3) . ?
F1A C6A 1.353(3) . ?
F2A C10A 1.352(3) . ?
O2A C17A 1.253(3) . ?
O2 C17 1.250(3) . ?
O3A C18A 1.240(3) . ?
O3 C18 1.242(4) . ?
O1 C2 1.427(4) . ?
O1 C3 1.431(4) . ?
N2 C9 1.399(3) . ?
N2 C15 1.353(4) . ?
N2 C11 1.479(3) . ?
N2A C9A 1.404(3) . ?
N2A C15A 1.352(4) . ?
N2A C11A 1.479(3) . ?
O1A C2A 1.420(4) . ?
O1A C3A 1.426(4) . ?
N1 C5 1.410(3) . ?
N1 C1 1.467(4) . ?
N1 C4 1.466(4) . ?
N3 C18 1.336(4) . ?
N3 C19 1.449(4) . ?
N3A C18A 1.341(4) . ?
N3A C19A 1.458(4) . ?
N1A C5A 1.404(4) . ?
N1A C4A 1.466(4) . ?
N1A C1A 1.467(4) . ?
C8 C9 1.407(4) . ?
C8 C7 1.408(4) . ?
C8 C17 1.463(4) . ?
C9A C8A 1.402(4) . ?
C9A C10A 1.417(4) . ?
C9 C10 1.414(4) . ?
C8A C7A 1.408(4) . ?
C8A C17A 1.465(4) . ?
C15A C16A 1.364(4) . ?
C10A C5A 1.392(4) . ?
C15 C16 1.369(4) . ?
C7 C6 1.359(4) . ?
C16 C17 1.434(4) . ?
C16 C18 1.498(4) . ?
C20A C19A 1.508(4) . ?
C20A C25A 1.379(4) . ?
C20A C21A 1.381(5) . ?
C10 C5 1.385(4) . ?
C16A C17A 1.442(4) . ?
C16A C18A 1.500(4) . ?
C7A C6A 1.364(4) . ?
C5 C6 1.409(4) . ?
C5A C6A 1.408(4) . ?
C20 C19 1.504(4) . ?
C20 C25 1.381(5) . ?
C20 C21 1.381(5) . ?
C1 C2 1.515(4) . ?
C11A C12A 1.531(4) . ?
C11 C12 1.535(4) . ?
C12 C13 1.524(4) . ?
C12A C13A 1.518(4) . ?
C4 C3 1.513(4) . ?
C4A C3A 1.511(4) . ?
C1A C2A 1.514(4) . ?
C13A C14A 1.523(5) . ?
C25A C24A 1.395(5) . ?
C13 C14 1.517(6) . ?
C23A C22A 1.385(5) . ?
C23A C24A 1.367(5) . ?
C21A C22A 1.388(5) . ?
C25 C24 1.403(6) . ?
C21 C22 1.382(5) . ?
C23 C22 1.367(6) . ?
C23 C24 1.371(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.7(2) . . ?
C9 N2 C11 122.9(2) . . ?
C15 N2 C9 118.6(2) . . ?
C15 N2 C11 117.6(2) . . ?
C9A N2A C11A 123.0(2) . . ?
C15A N2A C9A 118.7(2) . . ?
C15A N2A C11A 117.4(2) . . ?
C2A O1A C3A 109.1(3) . . ?
C5 N1 C1 115.2(2) . . ?
C5 N1 C4 119.1(2) . . ?
C4 N1 C1 111.9(2) . . ?
C18 N3 C19 123.5(2) . . ?
C18A N3A C19A 123.3(2) . . ?
C5A N1A C4A 120.5(2) . . ?
C5A N1A C1A 116.0(2) . . ?
C4A N1A C1A 112.4(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 C17 121.6(2) . . ?
C7 C8 C17 117.9(2) . . ?
N2A C9A C10A 123.7(2) . . ?
C8A C9A N2A 119.1(2) . . ?
C8A C9A C10A 117.2(2) . . ?
N2 C9 C8 119.5(2) . . ?
N2 C9 C10 123.7(2) . . ?
C8 C9 C10 116.7(2) . . ?
C9A C8A C7A 120.3(3) . . ?
C9A C8A C17A 122.1(2) . . ?
C7A C8A C17A 117.5(2) . . ?
N2A C15A C16A 125.4(3) . . ?
F2A C10A C9A 119.5(2) . . ?
F2A C10A C5A 116.8(2) . . ?
C5A C10A C9A 123.7(3) . . ?
N2 C15 C16 125.2(3) . . ?
C6 C7 C8 119.3(3) . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 C18 116.5(2) . . ?
C17 C16 C18 123.7(3) . . ?
C25A C20A C19A 121.2(3) . . ?
C25A C20A C21A 118.1(3) . . ?
C21A C20A C19A 120.6(3) . . ?
O2 C17 C8 120.0(2) . . ?
O2 C17 C16 124.8(2) . . ?
C16 C17 C8 115.2(2) . . ?
F2 C10 C9 119.3(2) . . ?
F2 C10 C5 116.5(2) . . ?
C5 C10 C9 124.2(3) . . ?
C15A C16A C17A 119.6(3) . . ?
C15A C16A C18A 116.8(2) . . ?
C17A C16A C18A 123.5(3) . . ?
C6A C7A C8A 119.5(3) . . ?
O2A C17A C8A 120.3(2) . . ?
O2A C17A C16A 124.8(3) . . ?
C16A C17A C8A 115.0(2) . . ?
C10 C5 N1 125.2(3) . . ?
C10 C5 C6 115.1(2) . . ?
C6 C5 N1 119.6(2) . . ?
F1 C6 C7 119.0(3) . . ?
F1 C6 C5 117.1(2) . . ?
C7 C6 C5 123.8(3) . . ?
O3A C18A N3A 123.8(3) . . ?
O3A C18A C16A 121.3(3) . . ?
N3A C18A C16A 114.9(2) . . ?
N1A C5A C6A 119.6(2) . . ?
C10A C5A N1A 124.8(3) . . ?
C10A C5A C6A 115.4(2) . . ?
O3 C18 N3 123.5(3) . . ?
O3 C18 C16 121.2(3) . . ?
N3 C18 C16 115.3(2) . . ?
C25 C20 C19 119.4(3) . . ?
C21 C20 C19 122.9(3) . . ?
C21 C20 C25 117.7(3) . . ?
N1 C1 C2 110.8(2) . . ?
N2A C11A C12A 110.8(2) . . ?
N3A C19A C20A 111.6(2) . . ?
N2 C11 C12 110.6(2) . . ?
F1A C6A C7A 119.1(3) . . ?
F1A C6A C5A 117.2(2) . . ?
C7A C6A C5A 123.4(3) . . ?
C13 C12 C11 113.6(3) . . ?
C13A C12A C11A 113.2(3) . . ?
N1 C4 C3 108.4(3) . . ?
N1A C4A C3A 108.3(3) . . ?
N3 C19 C20 113.5(3) . . ?
N1A C1A C2A 110.0(3) . . ?
C12A C13A C14A 111.0(3) . . ?
C20A C25A C24A 121.3(3) . . ?
O1 C2 C1 111.1(3) . . ?
C14 C13 C12 111.2(3) . . ?
C24A C23A C22A 119.7(3) . . ?
O1 C3 C4 110.4(3) . . ?
C20A C21A C22A 121.1(3) . . ?
O1A C2A C1A 111.7(3) . . ?
C23A C22A C21A 119.9(3) . . ?
O1A C3A C4A 110.8(3) . . ?
C20 C25 C24 120.3(4) . . ?
C20 C21 C22 122.2(4) . . ?
C23A C24A C25A 119.8(3) . . ?
C22 C23 C24 119.8(4) . . ?
C23 C22 C21 119.6(4) . . ?
C23 C24 C25 120.3(4) . . ?

_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_p21_c_210k
_database_code_depnum_ccdc_archive 'CCDC 2386805'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2025-01-14
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.0472(4)
_cell_length_b                   15.1916(11)
_cell_length_c                   24.5820(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.256(2)
_cell_angle_gamma                90
_cell_volume                     2248.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6950
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.028
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            30038
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.137
_diffrn_ambient_temperature      210.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                3423
_reflns_number_total             4619
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0100(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4619
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.042
_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)+(0.0723P)²+2.4749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1834
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C25 \\sim C24 \\sim C23 \\sim C22 \\sim C21 \\sim C20: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(C14A) = Uanis(C14)
3. Rigid body (RIGU) restrains
 C25, C24, C23, C22, C21, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: C14(0.8) H18(0.8) H17(0.8) H16(0.8) C14A(0.2) H18A(0.2) H17A(0.2)
 H16A(0.2)
5.a Secondary CH2 refined with riding coordinates:
 C11(H10,H11), C19(H22,H21), C4(H8,H7), C1(H1,H2), C2(H3,H4), C12(H13,H12),
 C3(H6,H5), C13(H14,H15)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H19), C7(H9), C21(H23), C25(H27), C22(H24), C23(H25), C24(H26)
5.c Idealised Me refined as rotating group:
 C14(H18,H17,H16), C14A(H18A,H17A,H16A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
F2 F 0.8278(2) 0.33196(10) 0.40232(6) 0.0480(4) Uani 1 1 d . . . . .
F1 F 0.8100(3) 0.45352(11) 0.22612(6) 0.0521(4) Uani 1 1 d . . . . .
O1 O 1.2468(3) 0.18643(13) 0.26637(8) 0.0548(5) Uani 1 1 d . . . . .
O2 O 0.2095(3) 0.60839(14) 0.30566(8) 0.0556(5) Uani 1 1 d . . . . .
O3 O -0.0898(3) 0.58799(14) 0.45332(7) 0.0552(5) Uani 1 1 d . . . . .
N2 N 0.4492(3) 0.43593(12) 0.42526(7) 0.0333(4) Uani 1 1 d . . . . .
N1 N 0.9830(3) 0.32372(13) 0.30496(8) 0.0384(5) Uani 1 1 d . . . . .
N3 N -0.1064(3) 0.65165(14) 0.36962(9) 0.0422(5) Uani 1 1 d . . . . .
C9 C 0.5522(4) 0.44086(14) 0.37643(8) 0.0313(5) Uani 1 1 d . . . . .
C8 C 0.4709(4) 0.50053(14) 0.33620(9) 0.0336(5) Uani 1 1 d . . . . .
C10 C 0.7326(4) 0.38796(15) 0.36438(9) 0.0339(5) Uani 1 1 d . . . . .
C5 C 0.8204(4) 0.38673(15) 0.31388(9) 0.0341(5) Uani 1 1 d . . . . .
C15 C 0.2699(4) 0.48656(15) 0.43120(9) 0.0339(5) Uani 1 1 d . . . . .
H19 H 0.200407 0.480208 0.463646 0.041 Uiso 1 1 calc R U . . .
C17 C 0.2781(4) 0.55669(15) 0.34295(9) 0.0373(5) Uani 1 1 d . . . . .
C16 C 0.1807(4) 0.54656(14) 0.39373(9) 0.0341(5) Uani 1 1 d . . . . .
C18 C -0.0171(4) 0.59677(16) 0.40831(9) 0.0380(5) Uani 1 1 d . . . . .
C11 C 0.5100(4) 0.36993(16) 0.46816(9) 0.0396(5) Uani 1 1 d . . . . .
H10 H 0.451160 0.388286 0.502232 0.047 Uiso 1 1 calc R U . . .
H11 H 0.672132 0.366819 0.474760 0.047 Uiso 1 1 calc R U . . .
C6 C 0.7331(4) 0.44985(16) 0.27626(9) 0.0375(5) Uani 1 1 d . . . . .
C7 C 0.5674(4) 0.50628(16) 0.28664(10) 0.0391(5) Uani 1 1 d . . . . .
H9 H 0.517819 0.548978 0.260655 0.047 Uiso 1 1 calc R U . . .
C19 C -0.2988(4) 0.70588(17) 0.37646(11) 0.0451(6) Uani 1 1 d . . . . .
H22 H -0.366918 0.686090 0.408999 0.054 Uiso 1 1 calc R U . . .
H21 H -0.407790 0.697409 0.344870 0.054 Uiso 1 1 calc R U . . .
C4 C 0.9042(4) 0.23151(16) 0.30301(11) 0.0439(6) Uani 1 1 d . . . . .
H8 H 0.813085 0.220949 0.268582 0.053 Uiso 1 1 calc R U . . .
H7 H 0.812221 0.220756 0.333144 0.053 Uiso 1 1 calc R U . . .
C1 C 1.1284(4) 0.33813(17) 0.26112(10) 0.0437(6) Uani 1 1 d . . . . .
H1 H 1.182357 0.398985 0.262017 0.052 Uiso 1 1 calc R U . . .
H2 H 1.046502 0.327426 0.225456 0.052 Uiso 1 1 calc R U . . .
C20 C -0.2464(4) 0.80283(17) 0.38224(11) 0.0454(6) Uani 1 1 d . U . . .
C2 C 1.3203(4) 0.27528(19) 0.27001(12) 0.0499(7) Uani 1 1 d . . . . .
H3 H 1.424771 0.286011 0.242534 0.060 Uiso 1 1 calc R U . . .
H4 H 1.398556 0.285658 0.306132 0.060 Uiso 1 1 calc R U . . .
C12 C 0.4192(5) 0.27917(17) 0.45192(12) 0.0529(7) Uani 1 1 d . . . . .
H13 H 0.257922 0.279110 0.453708 0.063 Uiso 1 1 calc R U . . .
H12 H 0.447719 0.267269 0.414007 0.063 Uiso 1 1 calc R U . . .
C3 C 1.0999(5) 0.16968(19) 0.30751(13) 0.0534(7) Uani 1 1 d . . . . .
H6 H 1.181393 0.176197 0.343620 0.064 Uiso 1 1 calc R U . . .
H5 H 1.046276 0.108876 0.304096 0.064 Uiso 1 1 calc R U . . .
C21 C -0.4076(5) 0.86453(19) 0.36588(12) 0.0543(7) Uani 1 1 d . U . . .
H23 H -0.548345 0.845558 0.351061 0.065 Uiso 1 1 calc R U . . .
C25 C -0.0406(5) 0.8326(2) 0.40385(15) 0.0655(8) Uani 1 1 d . U . . .
H27 H 0.071471 0.791922 0.415185 0.079 Uiso 1 1 calc R U . . .
C22 C -0.3641(7) 0.9539(2) 0.37106(14) 0.0689(9) Uani 1 1 d . U . . .
H24 H -0.474772 0.995098 0.359626 0.083 Uiso 1 1 calc R U . . .
C23 C -0.1612(7) 0.9820(2) 0.39271(17) 0.0807(11) Uani 1 1 d . U . . .
H25 H -0.132427 1.042627 0.396576 0.097 Uiso 1 1 calc R U . . .
C24 C 0.0013(7) 0.9223(3) 0.40888(19) 0.0839(11) Uani 1 1 d . U . . .
H26 H 0.141700 0.942066 0.423450 0.101 Uiso 1 1 calc R U . . .
H20 H -0.046(6) 0.649(2) 0.3364(16) 0.082(11) Uiso 1 1 d . . . . .
C13 C 0.5196(8) 0.2072(2) 0.48761(14) 0.0839(12) Uani 1 1 d . . . . .
H14 H 0.501729 0.221855 0.525777 0.101 Uiso 1 1 calc R U . A 1
H15 H 0.679222 0.204582 0.483551 0.101 Uiso 1 1 calc R U . A 1
C14 C 0.4203(14) 0.1175(3) 0.4753(3) 0.104(3) Uani 0.8 1 d . . P B 1
H18 H 0.262953 0.118884 0.480146 0.156 Uiso 0.8 1 calc R U P B 1
H17 H 0.493408 0.074465 0.499887 0.156 Uiso 0.8 1 calc R U P B 1
H16 H 0.440597 0.101608 0.437841 0.156 Uiso 0.8 1 calc R U P B 1
C14A C 0.299(6) 0.1306(17) 0.4701(15) 0.104(3) Uani 0.2 1 d . . P B 2
H18A H 0.158477 0.162022 0.465373 0.156 Uiso 0.2 1 calc R U P B 2
H17A H 0.293510 0.087622 0.499139 0.156 Uiso 0.2 1 calc R U P B 2
H16A H 0.324275 0.100830 0.436360 0.156 Uiso 0.2 1 calc R U P B 2


_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
F2 C10 1.352(3) . ?
F1 C6 1.358(2) . ?
O1 C2 1.421(3) . ?
O1 C3 1.429(3) . ?
O2 C17 1.249(3) . ?
O3 C18 1.235(3) . ?
N2 C9 1.404(3) . ?
N2 C15 1.348(3) . ?
N2 C11 1.477(3) . ?
N1 C5 1.404(3) . ?
N1 C4 1.479(3) . ?
N1 C1 1.468(3) . ?
N3 C18 1.340(3) . ?
N3 C19 1.448(3) . ?
N3 H20 0.93(4) . ?
C9 C8 1.397(3) . ?
C9 C10 1.408(3) . ?
C8 C17 1.466(3) . ?
C8 C7 1.401(3) . ?
C10 C5 1.394(3) . ?
C5 C6 1.401(3) . ?
C15 H19 0.9400 . ?
C15 C16 1.371(3) . ?
C17 C16 1.436(3) . ?
C16 C18 1.490(3) . ?
C11 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 C12 1.524(4) . ?
C6 C7 1.361(3) . ?
C7 H9 0.9400 . ?
C19 H22 0.9800 . ?
C19 H21 0.9800 . ?
C19 C20 1.510(4) . ?
C4 H8 0.9800 . ?
C4 H7 0.9800 . ?
C4 C3 1.507(4) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 C2 1.503(4) . ?
C20 C21 1.385(4) . ?
C20 C25 1.384(4) . ?
C2 H3 0.9800 . ?
C2 H4 0.9800 . ?
C12 H13 0.9800 . ?
C12 H12 0.9800 . ?
C12 C13 1.496(4) . ?
C3 H6 0.9800 . ?
C3 H5 0.9800 . ?
C21 H23 0.9400 . ?
C21 C22 1.387(4) . ?
C25 H27 0.9400 . ?
C25 C24 1.390(5) . ?
C22 H24 0.9400 . ?
C22 C23 1.361(5) . ?
C23 H25 0.9400 . ?
C23 C24 1.369(6) . ?
C24 H26 0.9400 . ?
C13 H14 0.9800 . ?
C13 H15 0.9800 . ?
C13 C14 1.508(8) . ?
C13 C14A 1.79(4) . ?
C14 H18 0.9700 . ?
C14 H17 0.9700 . ?
C14 H16 0.9700 . ?
C14A H18A 0.9700 . ?
C14A H17A 0.9700 . ?
C14A H16A 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 109.61(19) . . ?
C9 N2 C11 123.07(18) . . ?
C15 N2 C9 119.09(18) . . ?
C15 N2 C11 117.40(18) . . ?
C5 N1 C4 114.99(18) . . ?
C5 N1 C1 119.2(2) . . ?
C1 N1 C4 109.29(18) . . ?
C18 N3 C19 123.2(2) . . ?
C18 N3 H20 115(2) . . ?
C19 N3 H20 121(2) . . ?
N2 C9 C10 124.2(2) . . ?
C8 C9 N2 119.00(19) . . ?
C8 C9 C10 116.77(19) . . ?
C9 C8 C17 121.95(19) . . ?
C9 C8 C7 120.5(2) . . ?
C7 C8 C17 117.5(2) . . ?
F2 C10 C9 120.21(19) . . ?
F2 C10 C5 115.66(19) . . ?
C5 C10 C9 124.1(2) . . ?
C10 C5 N1 118.5(2) . . ?
C10 C5 C6 115.3(2) . . ?
C6 C5 N1 126.2(2) . . ?
N2 C15 H19 117.4 . . ?
N2 C15 C16 125.3(2) . . ?
C16 C15 H19 117.4 . . ?
O2 C17 C8 119.8(2) . . ?
O2 C17 C16 124.8(2) . . ?
C16 C17 C8 115.4(2) . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 C18 117.0(2) . . ?
C17 C16 C18 123.8(2) . . ?
O3 C18 N3 123.4(2) . . ?
O3 C18 C16 121.3(2) . . ?
N3 C18 C16 115.3(2) . . ?
N2 C11 H10 109.3 . . ?
N2 C11 H11 109.3 . . ?
N2 C11 C12 111.5(2) . . ?
H10 C11 H11 108.0 . . ?
C12 C11 H10 109.3 . . ?
C12 C11 H11 109.3 . . ?
F1 C6 C5 119.2(2) . . ?
F1 C6 C7 117.6(2) . . ?
C7 C6 C5 123.2(2) . . ?
C8 C7 H9 120.1 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H9 120.1 . . ?
N3 C19 H22 108.8 . . ?
N3 C19 H21 108.8 . . ?
N3 C19 C20 113.7(2) . . ?
H22 C19 H21 107.7 . . ?
C20 C19 H22 108.8 . . ?
C20 C19 H21 108.8 . . ?
N1 C4 H8 109.7 . . ?
N1 C4 H7 109.7 . . ?
N1 C4 C3 109.8(2) . . ?
H8 C4 H7 108.2 . . ?
C3 C4 H8 109.7 . . ?
C3 C4 H7 109.7 . . ?
N1 C1 H1 110.2 . . ?
N1 C1 H2 110.2 . . ?
N1 C1 C2 107.7(2) . . ?
H1 C1 H2 108.5 . . ?
C2 C1 H1 110.2 . . ?
C2 C1 H2 110.2 . . ?
C21 C20 C19 119.8(3) . . ?
C25 C20 C19 121.9(2) . . ?
C25 C20 C21 118.3(3) . . ?
O1 C2 C1 111.2(2) . . ?
O1 C2 H3 109.4 . . ?
O1 C2 H4 109.4 . . ?
C1 C2 H3 109.4 . . ?
C1 C2 H4 109.4 . . ?
H3 C2 H4 108.0 . . ?
C11 C12 H13 109.0 . . ?
C11 C12 H12 109.0 . . ?
H13 C12 H12 107.8 . . ?
C13 C12 C11 113.0(3) . . ?
C13 C12 H13 109.0 . . ?
C13 C12 H12 109.0 . . ?
O1 C3 C4 111.8(2) . . ?
O1 C3 H6 109.2 . . ?
O1 C3 H5 109.2 . . ?
C4 C3 H6 109.2 . . ?
C4 C3 H5 109.2 . . ?
H6 C3 H5 107.9 . . ?
C20 C21 H23 119.6 . . ?
C20 C21 C22 120.9(3) . . ?
C22 C21 H23 119.6 . . ?
C20 C25 H27 119.8 . . ?
C20 C25 C24 120.3(3) . . ?
C24 C25 H27 119.8 . . ?
C21 C22 H24 120.0 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H24 120.0 . . ?
C22 C23 H25 119.9 . . ?
C22 C23 C24 120.2(3) . . ?
C24 C23 H25 119.9 . . ?
C25 C24 H26 119.9 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H26 119.9 . . ?
C12 C13 H14 108.7 . . ?
C12 C13 H15 108.7 . . ?
C12 C13 C14 114.2(4) . . ?
C12 C13 C14A 94.6(10) . . ?
H14 C13 H15 107.6 . . ?
C14 C13 H14 108.7 . . ?
C14 C13 H15 108.7 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H17 109.5 . . ?
C13 C14 H16 109.5 . . ?
H18 C14 H17 109.5 . . ?
H18 C14 H16 109.5 . . ?
H17 C14 H16 109.5 . . ?
C13 C14A H18A 109.5 . . ?
C13 C14A H17A 109.5 . . ?
C13 C14A H16A 109.5 . . ?
H18A C14A H17A 109.5 . . ?
H18A C14A H16A 109.5 . . ?
H17A C14A H16A 109.5 . . ?

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
F2 C10 C5 N1 5.4(3) . . . . ?
F2 C10 C5 C6 -175.07(19) . . . . ?
F1 C6 C7 C8 175.1(2) . . . . ?
O2 C17 C16 C15 179.1(2) . . . . ?
O2 C17 C16 C18 0.3(4) . . . . ?
N2 C9 C8 C17 -1.4(3) . . . . ?
N2 C9 C8 C7 -179.0(2) . . . . ?
N2 C9 C10 F2 -4.6(3) . . . . ?
N2 C9 C10 C5 173.3(2) . . . . ?
N2 C15 C16 C17 1.7(4) . . . . ?
N2 C15 C16 C18 -179.4(2) . . . . ?
N2 C11 C12 C13 166.6(2) . . . . ?
N1 C5 C6 F1 -0.8(3) . . . . ?
N1 C5 C6 C7 176.6(2) . . . . ?
N1 C4 C3 O1 -55.7(3) . . . . ?
N1 C1 C2 O1 62.5(3) . . . . ?
N3 C19 C20 C21 152.2(2) . . . . ?
N3 C19 C20 C25 -28.1(4) . . . . ?
C9 N2 C15 C16 -2.6(3) . . . . ?
C9 N2 C11 C12 -75.3(3) . . . . ?
C9 C8 C17 O2 -179.2(2) . . . . ?
C9 C8 C17 C16 0.5(3) . . . . ?
C9 C8 C7 C6 3.9(3) . . . . ?
C9 C10 C5 N1 -172.6(2) . . . . ?
C9 C10 C5 C6 6.9(3) . . . . ?
C8 C9 C10 F2 176.55(19) . . . . ?
C8 C9 C10 C5 -5.5(3) . . . . ?
C8 C17 C16 C15 -0.5(3) . . . . ?
C8 C17 C16 C18 -179.4(2) . . . . ?
C10 C9 C8 C17 177.5(2) . . . . ?
C10 C9 C8 C7 -0.1(3) . . . . ?
C10 C5 C6 F1 179.7(2) . . . . ?
C10 C5 C6 C7 -2.8(3) . . . . ?
C5 N1 C4 C3 -165.9(2) . . . . ?
C5 N1 C1 C2 165.3(2) . . . . ?
C5 C6 C7 C8 -2.3(4) . . . . ?
C15 N2 C9 C8 2.4(3) . . . . ?
C15 N2 C9 C10 -176.5(2) . . . . ?
C15 N2 C11 C12 97.1(2) . . . . ?
C15 C16 C18 O3 3.8(4) . . . . ?
C15 C16 C18 N3 -176.8(2) . . . . ?
C17 C8 C7 C6 -173.9(2) . . . . ?
C17 C16 C18 O3 -177.4(2) . . . . ?
C17 C16 C18 N3 2.0(3) . . . . ?
C18 N3 C19 C20 109.2(3) . . . . ?
C11 N2 C9 C8 174.6(2) . . . . ?
C11 N2 C9 C10 -4.3(3) . . . . ?
C11 N2 C15 C16 -175.2(2) . . . . ?
C11 C12 C13 C14 175.5(4) . . . . ?
C11 C12 C13 C14A 159.8(11) . . . . ?
C7 C8 C17 O2 -1.5(3) . . . . ?
C7 C8 C17 C16 178.2(2) . . . . ?
C19 N3 C18 O3 -0.5(4) . . . . ?
C19 N3 C18 C16 -179.9(2) . . . . ?
C19 C20 C21 C22 179.6(3) . . . . ?
C19 C20 C25 C24 -179.6(3) . . . . ?
C4 N1 C5 C10 67.2(3) . . . . ?
C4 N1 C5 C6 -112.2(3) . . . . ?
C4 N1 C1 C2 -59.6(3) . . . . ?
C1 N1 C5 C10 -160.1(2) . . . . ?
C1 N1 C5 C6 20.5(3) . . . . ?
C1 N1 C4 C3 57.0(3) . . . . ?
C20 C21 C22 C23 -0.3(5) . . . . ?
C20 C25 C24 C23 0.3(6) . . . . ?
C2 O1 C3 C4 57.2(3) . . . . ?
C3 O1 C2 C1 -60.9(3) . . . . ?
C21 C20 C25 C24 0.1(5) . . . . ?
C21 C22 C23 C24 0.7(6) . . . . ?
C25 C20 C21 C22 -0.1(4) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?

_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_P-1_120K
_database_code_depnum_ccdc_archive 'CCDC 2386812'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-04
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.49
_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'
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'

_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                   10.6690(2)
_cell_length_b                   13.7277(3)
_cell_length_c                   15.4240(4)
_cell_angle_alpha                84.1320(10)
_cell_angle_beta                 88.2880(10)
_cell_angle_gamma                77.2170(10)
_cell_volume                     2191.42(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.9375.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            70861
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_min         1.924
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                   xray
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6751
_reflns_number_total             9023
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.106
_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)+(0.0914P)²+2.6714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.2107
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C011(H01Y,H), C013(H01A,H01B), C014(H01C,H01D), C015(H01Z,HA), C016(H01E,
 H01F), C018(H01G,H01H), C019(H01,HB), C01A(H0AA,HC), C01B(H01I,H01J),
 C01C(H1AA,HD), C01E(H01K,H01L), C01F(H3AA,HE), C01H(H01M,H01N), C01J(H01O,
 H01P), C01K(H6AA,HF), C01P(H9AA,HG)
2.b Aromatic/amide H refined with riding coordinates:
 N00E(H00E), N00G(H00G), C00Q(H00Q), C00R(H00R), C00T(H00T), C010(H010),
 C01D(H2AA), C01G(H4AA), C01I(H5AA), C01L(H01Q), C01M(H7AA), C01N(H01R),
 C01O(H8AA), C01Q(H01S), C01R(H01T), C01T(H01U)
2.c Idealised Me refined as rotating group:
 C01S(H0BA,HH,HI), C01U(H01V,H01W,H01X)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
F2 F 0.35338(13) 0.78518(10) 0.70428(9) 0.0333(3) Uani 1 1 d . . . . .
F1 F 0.48763(14) 0.44687(10) 0.65343(9) 0.0337(3) Uani 1 1 d . . . . .
F2A F 1.13165(14) 0.19722(10) 0.28121(10) 0.0359(3) Uani 1 1 d . . . . .
F1A F 1.03005(15) 0.52889(11) 0.35508(9) 0.0366(4) Uani 1 1 d . . . . .
O2A O 0.77382(17) 0.35787(13) 0.56472(11) 0.0325(4) Uani 1 1 d . . . . .
O2 O 0.73724(17) 0.61779(13) 0.43775(11) 0.0325(4) Uani 1 1 d . . . . .
O3A O 0.68491(17) 0.07107(13) 0.58746(12) 0.0354(4) Uani 1 1 d . . . . .
O3 O 0.81244(19) 0.90908(13) 0.40767(12) 0.0386(4) Uani 1 1 d . . . . .
O1 O 0.17548(17) 0.55369(15) 0.89204(12) 0.0381(4) Uani 1 1 d . . . . .
O1A O 1.3029(2) 0.44656(16) 0.09883(13) 0.0451(5) Uani 1 1 d . . . . .
N2 N 0.54291(19) 0.83836(14) 0.58457(12) 0.0257(4) Uani 1 1 d . . . . .
N1 N 0.35686(18) 0.58215(15) 0.75908(12) 0.0272(4) Uani 1 1 d . . . . .
N2A N 0.95513(19) 0.14075(14) 0.41021(12) 0.0259(4) Uani 1 1 d . . . . .
N3A N 0.63393(19) 0.22902(15) 0.63024(12) 0.0285(4) Uani 1 1 d . . . . .
H20A H 0.650595 0.289316 0.622829 0.034 Uiso 1 1 calc R . . . .
N1A N 1.14209(19) 0.39952(16) 0.23885(13) 0.0289(4) Uani 1 1 d . . . . .
N3 N 0.8679(2) 0.75082(15) 0.36639(13) 0.0301(4) Uani 1 1 d . . . . .
H20 H 0.853444 0.689846 0.374256 0.036 Uiso 1 1 calc R . . . .
C9A C 0.9816(2) 0.23689(17) 0.39757(14) 0.0244(4) Uani 1 1 d . . . . .
C5 C 0.4232(2) 0.61517(17) 0.68540(14) 0.0248(5) Uani 1 1 d . . . . .
C9 C 0.5193(2) 0.74173(17) 0.59836(14) 0.0246(5) Uani 1 1 d . . . . .
C8 C 0.5867(2) 0.66614(17) 0.54872(14) 0.0245(5) Uani 1 1 d . . . . .
C16 C 0.7024(2) 0.78657(17) 0.47419(14) 0.0246(5) Uani 1 1 d . . . . .
C17 C 0.6810(2) 0.68625(17) 0.48221(14) 0.0252(5) Uani 1 1 d . . . . .
C8A C 0.9212(2) 0.30995(17) 0.45152(14) 0.0253(5) Uani 1 1 d . . . . .
C17A C 0.8266(2) 0.29067(17) 0.51813(14) 0.0264(5) Uani 1 1 d . . . . .
C5A C 1.0801(2) 0.36441(18) 0.31310(15) 0.0261(5) Uani 1 1 d . . . . .
C15 C 0.6337(2) 0.85564(17) 0.52544(14) 0.0263(5) Uani 1 1 d . . . . .
H19 H 0.651188 0.920938 0.519009 0.032 Uiso 1 1 calc R . . . .
C7 C 0.5703(2) 0.56704(18) 0.56510(14) 0.0270(5) Uani 1 1 d . . . . .
H9 H 0.612488 0.516856 0.529587 0.032 Uiso 1 1 calc R . . . .
C10A C 1.0647(2) 0.26622(17) 0.33169(14) 0.0253(5) Uani 1 1 d . . . . .
C15A C 0.8650(2) 0.12363(17) 0.46987(14) 0.0260(5) Uani 1 1 d . . . . .
H19A H 0.845225 0.059135 0.474975 0.031 Uiso 1 1 calc R . . . .
C18A C 0.7014(2) 0.15815(18) 0.58327(14) 0.0274(5) Uani 1 1 d . . . . .
C10 C 0.4323(2) 0.71350(17) 0.66194(14) 0.0255(5) Uani 1 1 d . . . . .
C16A C 0.8002(2) 0.19152(17) 0.52342(14) 0.0259(5) Uani 1 1 d . . . . .
C20A C 0.5767(2) 0.21043(18) 0.78562(15) 0.0288(5) Uani 1 1 d . . . . .
C18 C 0.7992(2) 0.82098(18) 0.41331(15) 0.0280(5) Uani 1 1 d . . . . .
C6 C 0.4933(2) 0.54390(17) 0.63241(15) 0.0271(5) Uani 1 1 d . . . . .
C7A C 0.9439(2) 0.40751(18) 0.43938(15) 0.0283(5) Uani 1 1 d . . . . .
H9A H 0.906491 0.455839 0.477956 0.034 Uiso 1 1 calc R . . . .
C11A C 1.0040(2) 0.06190(17) 0.35164(15) 0.0276(5) Uani 1 1 d . . . . .
H10A H 0.993341 -0.003787 0.380114 0.033 Uiso 1 1 calc R . . . .
H11A H 1.096795 0.057565 0.340418 0.033 Uiso 1 1 calc R . . . .
C6A C 1.0198(2) 0.43217(18) 0.37183(15) 0.0288(5) Uani 1 1 d . . . . .
C11 C 0.4899(2) 0.91819(17) 0.64170(15) 0.0290(5) Uani 1 1 d . . . . .
H11 H 0.395753 0.925378 0.647429 0.035 Uiso 1 1 calc R . . . .
H10 H 0.506577 0.982897 0.615060 0.035 Uiso 1 1 calc R . . . .
C1 C 0.2398(2) 0.54877(19) 0.73996(16) 0.0299(5) Uani 1 1 d . . . . .
H1 H 0.257871 0.503858 0.692682 0.036 Uiso 1 1 calc R . . . .
H2 H 0.171803 0.607690 0.719722 0.036 Uiso 1 1 calc R . . . .
C19A C 0.5343(2) 0.21168(18) 0.69305(15) 0.0291(5) Uani 1 1 d . . . . .
H21A H 0.512486 0.146691 0.685233 0.035 Uiso 1 1 calc R . . . .
H22A H 0.455866 0.265195 0.681833 0.035 Uiso 1 1 calc R . . . .
C12 C 0.5512(2) 0.89322(19) 0.73215(15) 0.0319(5) Uani 1 1 d . . . . .
H12 H 0.564101 0.820079 0.748569 0.038 Uiso 1 1 calc R . . . .
H13 H 0.636856 0.910155 0.729193 0.038 Uiso 1 1 calc R . . . .
C20 C 0.9225(2) 0.77695(18) 0.20994(16) 0.0308(5) Uani 1 1 d . . . . .
C19 C 0.9650(2) 0.77004(19) 0.30326(15) 0.0316(5) Uani 1 1 d . . . . .
H22 H 1.042923 0.715608 0.312321 0.038 Uiso 1 1 calc R . . . .
H21 H 0.988402 0.833721 0.313630 0.038 Uiso 1 1 calc R . . . .
C12A C 0.9317(2) 0.08486(18) 0.26518(15) 0.0306(5) Uani 1 1 d . . . . .
H13A H 0.847009 0.066879 0.273798 0.037 Uiso 1 1 calc R . . . .
H12A H 0.916246 0.157889 0.247512 0.037 Uiso 1 1 calc R . . . .
C1A C 1.2575(2) 0.4365(2) 0.25442(17) 0.0324(5) Uani 1 1 d . . . . .
H2A H 1.330472 0.378959 0.268467 0.039 Uiso 1 1 calc R . . . .
H1A H 1.242516 0.477091 0.304724 0.039 Uiso 1 1 calc R . . . .
C4 C 0.3390(2) 0.64027(19) 0.83486(15) 0.0309(5) Uani 1 1 d . . . . .
H7 H 0.274047 0.703481 0.821923 0.037 Uiso 1 1 calc R . . . .
H8 H 0.420961 0.657420 0.849016 0.037 Uiso 1 1 calc R . . . .
C4A C 1.1525(2) 0.3482(2) 0.15908(15) 0.0327(5) Uani 1 1 d . . . . .
H8A H 1.070252 0.329677 0.148024 0.039 Uiso 1 1 calc R . . . .
H7A H 1.220845 0.286163 0.165474 0.039 Uiso 1 1 calc R . . . .
C25A C 0.5235(3) 0.2871(2) 0.83602(17) 0.0365(6) Uani 1 1 d . . . . .
H27A H 0.459519 0.341883 0.811795 0.044 Uiso 1 1 calc R . . . .
C2 C 0.1930(3) 0.4936(2) 0.82035(17) 0.0361(6) Uani 1 1 d . . . . .
H4 H 0.110550 0.476464 0.807451 0.043 Uiso 1 1 calc R . . . .
H3 H 0.256387 0.430189 0.836203 0.043 Uiso 1 1 calc R . . . .
C13A C 1.0035(3) 0.0288(2) 0.19233(16) 0.0360(6) Uani 1 1 d . . . . .
H14A H 1.029286 -0.043538 0.212468 0.043 Uiso 1 1 calc R . . . .
H15A H 1.082467 0.053745 0.177510 0.043 Uiso 1 1 calc R . . . .
C21A C 0.6717(3) 0.1319(2) 0.82178(17) 0.0386(6) Uani 1 1 d . . . . .
H23A H 0.710119 0.078988 0.787825 0.046 Uiso 1 1 calc R . . . .
C13 C 0.4716(3) 0.9486(2) 0.80271(17) 0.0389(6) Uani 1 1 d . . . . .
H14 H 0.462178 1.021769 0.788280 0.047 Uiso 1 1 calc R . . . .
H15 H 0.384640 0.934031 0.804527 0.047 Uiso 1 1 calc R . . . .
C23A C 0.6552(3) 0.2065(2) 0.95728(17) 0.0394(6) Uani 1 1 d . . . . .
H25A H 0.681216 0.204634 1.015908 0.047 Uiso 1 1 calc R . . . .
C3 C 0.2948(3) 0.5776(2) 0.91123(17) 0.0370(6) Uani 1 1 d . . . . .
H5 H 0.360603 0.514909 0.924204 0.044 Uiso 1 1 calc R . . . .
H6 H 0.284204 0.615184 0.963412 0.044 Uiso 1 1 calc R . . . .
C2A C 1.2898(3) 0.5000(2) 0.17412(18) 0.0405(6) Uani 1 1 d . . . . .
H3A H 1.221025 0.561496 0.164392 0.049 Uiso 1 1 calc R . . . .
H4A H 1.371105 0.520628 0.183815 0.049 Uiso 1 1 calc R . . . .
C25 C 0.7950(3) 0.8077(2) 0.18585(18) 0.0423(6) Uani 1 1 d . . . . .
H27 H 0.730928 0.822510 0.229587 0.051 Uiso 1 1 calc R . . . .
C24A C 0.5622(3) 0.2852(2) 0.92186(18) 0.0416(6) Uani 1 1 d . . . . .
H26A H 0.524263 0.338271 0.955771 0.050 Uiso 1 1 calc R . . . .
C21 C 1.0147(3) 0.7546(2) 0.14523(18) 0.0429(6) Uani 1 1 d . . . . .
H23 H 1.102894 0.733443 0.160356 0.051 Uiso 1 1 calc R . . . .
C22A C 0.7109(3) 0.1298(2) 0.90714(18) 0.0426(6) Uani 1 1 d . . . . .
H24A H 0.776065 0.075721 0.931204 0.051 Uiso 1 1 calc R . . . .
C3A C 1.1844(3) 0.4190(2) 0.08395(17) 0.0413(6) Uani 1 1 d . . . . .
H6A H 1.190956 0.385967 0.029339 0.050 Uiso 1 1 calc R . . . .
H5A H 1.114455 0.480020 0.077093 0.050 Uiso 1 1 calc R . . . .
C24 C 0.7583(3) 0.8175(3) 0.09902(19) 0.0498(7) Uani 1 1 d . . . . .
H26 H 0.670241 0.839210 0.083721 0.060 Uiso 1 1 calc R . . . .
C23 C 0.8509(3) 0.7954(2) 0.03534(19) 0.0497(7) Uani 1 1 d . . . . .
H25 H 0.826660 0.802453 -0.024129 0.060 Uiso 1 1 calc R . . . .
C14A C 0.9207(3) 0.0427(3) 0.11161(18) 0.0510(8) Uani 1 1 d . . . . .
H17A H 0.968348 0.003934 0.066474 0.077 Uiso 1 1 calc GR . . . .
H16A H 0.898694 0.113918 0.089879 0.077 Uiso 1 1 calc GR . . . .
H18A H 0.841804 0.019054 0.126409 0.077 Uiso 1 1 calc GR . . . .
C22 C 0.9785(3) 0.7631(2) 0.0579(2) 0.0529(8) Uani 1 1 d . . . . .
H24 H 1.041875 0.746612 0.014046 0.064 Uiso 1 1 calc R . . . .
C14 C 0.5333(4) 0.9179(3) 0.89170(19) 0.0546(8) Uani 1 1 d . . . . .
H18 H 0.617119 0.936079 0.891130 0.082 Uiso 1 1 calc GR . . . .
H16 H 0.544856 0.845138 0.905450 0.082 Uiso 1 1 calc GR . . . .
H17 H 0.477756 0.952522 0.935924 0.082 Uiso 1 1 calc GR . . . .


_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
F2 C10 1.355(3) . ?
F1 C6 1.353(3) . ?
F2A C10A 1.354(3) . ?
F1A C6A 1.354(3) . ?
O2A C17A 1.251(3) . ?
O2 C17 1.254(3) . ?
O3A C18A 1.241(3) . ?
O3 C18 1.243(3) . ?
O1 C2 1.430(3) . ?
O1 C3 1.429(3) . ?
O1A C2A 1.423(3) . ?
O1A C3A 1.429(3) . ?
N2 C9 1.398(3) . ?
N2 C15 1.353(3) . ?
N2 C11 1.480(3) . ?
N1 C5 1.410(3) . ?
N1 C1 1.470(3) . ?
N1 C4 1.466(3) . ?
N2A C9A 1.403(3) . ?
N2A C15A 1.352(3) . ?
N2A C11A 1.477(3) . ?
N3A C18A 1.339(3) . ?
N3A C19A 1.459(3) . ?
N1A C5A 1.402(3) . ?
N1A C1A 1.466(3) . ?
N1A C4A 1.468(3) . ?
N3 C18 1.337(3) . ?
N3 C19 1.449(3) . ?
C9A C8A 1.402(3) . ?
C9A C10A 1.415(3) . ?
C5 C10 1.385(3) . ?
C5 C6 1.410(3) . ?
C9 C8 1.407(3) . ?
C9 C10 1.415(3) . ?
C8 C17 1.464(3) . ?
C8 C7 1.406(3) . ?
C16 C17 1.438(3) . ?
C16 C15 1.368(3) . ?
C16 C18 1.496(3) . ?
C8A C17A 1.465(3) . ?
C8A C7A 1.406(3) . ?
C17A C16A 1.443(3) . ?
C5A C10A 1.394(3) . ?
C5A C6A 1.404(3) . ?
C7 C6 1.360(3) . ?
C15A C16A 1.367(3) . ?
C18A C16A 1.498(3) . ?
C20A C19A 1.508(3) . ?
C20A C25A 1.382(3) . ?
C20A C21A 1.388(4) . ?
C7A C6A 1.362(3) . ?
C11A C12A 1.530(3) . ?
C11 C12 1.533(3) . ?
C1 C2 1.516(3) . ?
C12 C13 1.521(3) . ?
C20 C19 1.509(3) . ?
C20 C25 1.382(4) . ?
C20 C21 1.389(4) . ?
C12A C13A 1.518(3) . ?
C1A C2A 1.517(3) . ?
C4 C3 1.513(3) . ?
C4A C3A 1.515(3) . ?
C25A C24A 1.395(4) . ?
C13A C14A 1.519(4) . ?
C21A C22A 1.389(4) . ?
C13 C14 1.519(4) . ?
C23A C24A 1.374(4) . ?
C23A C22A 1.387(4) . ?
C25 C24 1.391(4) . ?
C21 C22 1.399(4) . ?
C24 C23 1.379(5) . ?
C23 C22 1.378(5) . ?

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
C3 O1 C2 109.49(19) . . ?
C2A O1A C3A 109.1(2) . . ?
C9 N2 C11 122.94(18) . . ?
C15 N2 C9 118.68(19) . . ?
C15 N2 C11 117.53(19) . . ?
C5 N1 C1 115.08(18) . . ?
C5 N1 C4 119.03(19) . . ?
C4 N1 C1 111.64(19) . . ?
C9A N2A C11A 123.11(18) . . ?
C15A N2A C9A 118.79(19) . . ?
C15A N2A C11A 117.25(19) . . ?
C18A N3A C19A 123.5(2) . . ?
C5A N1A C1A 116.12(18) . . ?
C5A N1A C4A 120.53(19) . . ?
C1A N1A C4A 112.42(19) . . ?
C18 N3 C19 123.4(2) . . ?
N2A C9A C10A 123.8(2) . . ?
C8A C9A N2A 119.1(2) . . ?
C8A C9A C10A 117.0(2) . . ?
N1 C5 C6 119.2(2) . . ?
C10 C5 N1 125.3(2) . . ?
C10 C5 C6 115.4(2) . . ?
N2 C9 C8 119.6(2) . . ?
N2 C9 C10 123.6(2) . . ?
C8 C9 C10 116.8(2) . . ?
C9 C8 C17 121.5(2) . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 C17 117.8(2) . . ?
C17 C16 C18 123.7(2) . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 C18 116.7(2) . . ?
O2 C17 C8 119.9(2) . . ?
O2 C17 C16 124.8(2) . . ?
C16 C17 C8 115.3(2) . . ?
C9A C8A C17A 122.1(2) . . ?
C9A C8A C7A 120.5(2) . . ?
C7A C8A C17A 117.3(2) . . ?
O2A C17A C8A 120.4(2) . . ?
O2A C17A C16A 124.6(2) . . ?
C16A C17A C8A 115.0(2) . . ?
N1A C5A C6A 119.6(2) . . ?
C10A C5A N1A 124.9(2) . . ?
C10A C5A C6A 115.3(2) . . ?
N2 C15 C16 125.2(2) . . ?
C6 C7 C8 119.2(2) . . ?
F2A C10A C9A 119.6(2) . . ?
F2A C10A C5A 116.66(19) . . ?
C5A C10A C9A 123.7(2) . . ?
N2A C15A C16A 125.3(2) . . ?
O3A C18A N3A 123.8(2) . . ?
O3A C18A C16A 121.3(2) . . ?
N3A C18A C16A 114.9(2) . . ?
F2 C10 C5 116.75(19) . . ?
F2 C10 C9 119.41(19) . . ?
C5 C10 C9 123.8(2) . . ?
C17A C16A C18A 123.7(2) . . ?
C15A C16A C17A 119.5(2) . . ?
C15A C16A C18A 116.8(2) . . ?
C25A C20A C19A 121.2(2) . . ?
C25A C20A C21A 118.5(2) . . ?
C21A C20A C19A 120.2(2) . . ?
O3 C18 N3 123.5(2) . . ?
O3 C18 C16 121.2(2) . . ?
N3 C18 C16 115.2(2) . . ?
F1 C6 C5 117.2(2) . . ?
F1 C6 C7 119.1(2) . . ?
C7 C6 C5 123.6(2) . . ?
C6A C7A C8A 119.4(2) . . ?
N2A C11A C12A 110.77(18) . . ?
F1A C6A C5A 117.3(2) . . ?
F1A C6A C7A 119.0(2) . . ?
C7A C6A C5A 123.5(2) . . ?
N2 C11 C12 110.78(19) . . ?
N1 C1 C2 110.71(19) . . ?
N3A C19A C20A 111.80(19) . . ?
C13 C12 C11 113.6(2) . . ?
C25 C20 C19 122.4(2) . . ?
C25 C20 C21 118.4(2) . . ?
C21 C20 C19 119.1(2) . . ?
N3 C19 C20 113.5(2) . . ?
C13A C12A C11A 113.2(2) . . ?
N1A C1A C2A 110.0(2) . . ?
N1 C4 C3 108.5(2) . . ?
N1A C4A C3A 108.2(2) . . ?
C20A C25A C24A 121.1(2) . . ?
O1 C2 C1 110.9(2) . . ?
C12A C13A C14A 111.3(2) . . ?
C20A C21A C22A 120.6(2) . . ?
C14 C13 C12 111.6(2) . . ?
C24A C23A C22A 119.7(2) . . ?
O1 C3 C4 110.5(2) . . ?
O1A C2A C1A 111.5(2) . . ?
C20 C25 C24 121.5(3) . . ?
C23A C24A C25A 119.9(3) . . ?
C20 C21 C22 120.4(3) . . ?
C23A C22A C21A 120.1(3) . . ?
O1A C3A C4A 110.8(2) . . ?
C23 C24 C25 119.5(3) . . ?
C22 C23 C24 120.1(3) . . ?
C23 C22 C21 120.1(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_P-1_225K
_database_code_depnum_ccdc_archive 'CCDC 2386814'
loop_
_audit_author_name
_audit_author_address
'Parthapratim Munshi'
;Shiv Nadar Institution of Eminence Deemed to be University
India
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2026-02-12 downloaded from the CCDC.
;
_audit_creation_date             2024-01-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_systematic        ULF_7
_chemical_formula_moiety         'C25 H27 F2 N3 O3'
_chemical_formula_sum            'C25 H27 F2 N3 O3'
_chemical_formula_weight         455.508
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_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   5.3871(4)
_cell_length_b                   13.7306(11)
_cell_length_c                   15.4560(12)
_cell_angle_alpha                94.989(3)
_cell_angle_beta                 92.216(3)
_cell_angle_gamma                100.770(3)
_cell_volume                     1117.10(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9529
_cell_measurement_temperature    225(2)
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      2.65
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0943 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.9417.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             480.352
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29521
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9995
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.92
_diffrn_ambient_temperature      225(2)
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3337
_reflns_number_total             4390
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2881
_refine_diff_density_min         -0.2439
_refine_diff_density_rms         0.0519
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             10.6306
_refine_ls_extinction_coef       0.0086(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.1081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    53
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     112
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.0930
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0002P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1349
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C25 \\sim C20-C25A
 with sigma of 0.02
 C20-C21 \\sim C20-C21A
 with sigma of 0.02
 C23-C22 \\sim C23A-C22A
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C25-C24 \\sim C25A-C24A
 with sigma of 0.02
 C21-C22 \\sim C21A-C22A
 with sigma of 0.02
 C20-C22 \\sim C20-C22A
 with sigma of 0.04
 C20-C24 \\sim C20-C24A
 with sigma of 0.04
 C23-C25 \\sim C23A-C25A
 with sigma of 0.04
 C23-C21 \\sim C23A-C21A
 with sigma of 0.04
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C20: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C21, C22, C23, C24, C25, C20, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21A, C22A, C23A, C24A, C25A, C20, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(C22A)=
 Sof(H22A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(C23)=Sof(H23)=Sof(C25)=Sof(H25)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=
 Sof(C24)=Sof(H24)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C19(H19a,H19b), C15(H15a,H15b), C4(H4a,H4b), C3(H3a,H3b),
 C2(H2a,H2b), C1(H1a,H1b), C16(H16a,H16b)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C23(H23), C25(H25), C21(H21), C22(H22), C24(H24),
 C25A(H25A), C24A(H24A), C23A(H23A), C22A(H22A), C21A(H21A)
6.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
F2 F 0.0092(3) 0.79178(11) 0.29050(10) 0.0622(4) Uani 1.000000 . . . .
F1 F -0.0872(3) 0.45861(11) 0.34962(10) 0.0610(4) Uani 1.000000 . . . .
O2 O 0.5971(3) 0.62977(13) 0.56090(11) 0.0556(5) Uani 1.000000 . . . .
N2 N 0.4352(4) 0.84684(14) 0.41258(12) 0.0415(4) Uani 1.000000 . . . .
O3 O 1.0449(4) 0.91861(13) 0.58904(13) 0.0639(5) Uani 1.000000 . . . .
N1 N -0.2020(3) 0.59114(15) 0.24056(12) 0.0454(5) Uani 1.000000 . . . .
N3 N 0.9965(4) 0.76155(16) 0.62966(13) 0.0487(5) Uani 1.000000 . . . .
O1 O -0.5810(4) 0.55341(17) 0.10393(13) 0.0729(6) Uani 1.000000 . . . .
C8 C 0.3434(4) 0.67690(17) 0.45006(13) 0.0392(5) Uani 1.000000 . . . .
C9 C 0.2881(4) 0.75063(16) 0.39921(14) 0.0394(5) Uani 1.000000 . . . .
C17 C 0.5537(4) 0.69724(17) 0.51605(14) 0.0420(5) Uani 1.000000 . . . .
C5 C -0.0367(4) 0.62431(17) 0.31432(14) 0.0408(5) Uani 1.000000 . . . .
C10 C 0.0876(4) 0.72172(17) 0.33566(15) 0.0419(5) Uani 1.000000 . . . .
C16 C 0.6996(4) 0.79670(17) 0.52332(14) 0.0410(5) Uani 1.000000 . . . .
C7 C 0.2051(4) 0.57903(18) 0.43567(15) 0.0461(6) Uani 1.000000 . . . .
H9 H 0.2355(4) 0.53045(18) 0.47187(15) 0.0553(7) Uiso 1.000000 R . . .
C18 C 0.9291(5) 0.83127(18) 0.58353(15) 0.0455(5) Uani 1.000000 . . . .
C15 C 0.6336(4) 0.86454(17) 0.47182(14) 0.0430(5) Uani 1.000000 . . . .
H19 H 0.7342(4) 0.92880(17) 0.47800(14) 0.0516(6) Uiso 1.000000 R . . .
C6 C 0.0267(4) 0.55541(17) 0.36883(15) 0.0447(5) Uani 1.000000 . . . .
C20 C 1.1325(5) 0.78330(18) 0.78518(16) 0.0486(6) Uani 1.000000 D U . .
C11 C 0.4134(5) 0.92561(17) 0.35468(16) 0.0482(6) Uani 1.000000 . . . .
H11 H 0.2352(5) 0.93082(17) 0.34643(16) 0.0578(7) Uiso 1.000000 R . . .
H10 H 0.5069(5) 0.98979(17) 0.38189(16) 0.0578(7) Uiso 1.000000 R . . .
C19 C 1.2114(5) 0.78090(19) 0.69284(15) 0.0498(6) Uani 1.000000 . U . .
H21 H 1.3125(5) 0.72902(19) 0.68273(15) 0.0598(7) Uiso 1.000000 R . . .
H22 H 1.3185(5) 0.84494(19) 0.68428(15) 0.0598(7) Uiso 1.000000 R . . .
C12 C 0.5184(5) 0.9024(2) 0.26638(16) 0.0548(6) Uani 1.000000 . . . .
H13 H 0.7036(5) 0.9195(2) 0.27230(16) 0.0658(8) Uiso 1.000000 R . . .
H12 H 0.4709(5) 0.8307(2) 0.24956(16) 0.0658(8) Uiso 1.000000 R . . .
C4 C -0.1749(5) 0.6451(2) 0.16299(16) 0.0561(7) Uani 1.000000 . . . .
H8 H -0.2401(5) 0.7070(2) 0.17256(16) 0.0673(8) Uiso 1.000000 R . . .
H7 H 0.0042(5) 0.6622(2) 0.15056(16) 0.0673(8) Uiso 1.000000 R . . .
C1 C -0.4669(4) 0.5553(2) 0.25717(17) 0.0547(7) Uani 1.000000 . . . .
H1 H -0.4765(4) 0.5124(2) 0.30487(17) 0.0656(8) Uiso 1.000000 R . . .
H2 H -0.5460(4) 0.6121(2) 0.27486(17) 0.0656(8) Uiso 1.000000 R . . .
C2 C -0.6077(5) 0.4979(2) 0.1772(2) 0.0666(8) Uani 1.000000 . . . .
H3 H -0.7876(5) 0.4798(2) 0.1883(2) 0.0799(9) Uiso 1.000000 R . . .
H4 H -0.5439(5) 0.4361(2) 0.1646(2) 0.0799(9) Uiso 1.000000 R . . .
C3 C -0.3213(6) 0.5799(3) 0.08732(19) 0.0712(9) Uani 1.000000 . . . .
H6 H -0.2508(6) 0.5194(3) 0.07676(19) 0.0854(10) Uiso 1.000000 R . . .
H5 H -0.3041(6) 0.6154(3) 0.03491(19) 0.0854(10) Uiso 1.000000 R . . .
C13 C 0.4269(7) 0.9572(2) 0.19463(19) 0.0731(9) Uani 1.000000 . . . .
H15 H 0.2421(7) 0.9390(2) 0.18687(19) 0.0877(11) Uiso 1.000000 R . . .
H14 H 0.4721(7) 1.0291(2) 0.21102(19) 0.0877(11) Uiso 1.000000 R . . .
C23 C 0.979(3) 0.7980(13) 0.9560(7) 0.074(3) Uani 0.59(2) D U P 1
H25 H 0.929(3) 0.8034(13) 1.0136(7) 0.089(3) Uiso 0.59(2) R . P 1
C25 C 1.192(2) 0.7212(7) 0.8422(5) 0.060(2) Uani 0.59(2) D U P 1
H27 H 1.285(2) 0.6723(7) 0.8236(5) 0.072(2) Uiso 0.59(2) R . P 1
C21 C 0.992(3) 0.8542(9) 0.8157(5) 0.076(3) Uani 0.59(2) D U P 1
H23 H 0.951(3) 0.8999(9) 0.7783(5) 0.091(3) Uiso 0.59(2) R . P 1
C22 C 0.914(3) 0.8582(11) 0.8992(6) 0.094(4) Uani 0.59(2) D U P 1
H24 H 0.813(3) 0.9043(11) 0.9168(6) 0.113(4) Uiso 0.59(2) R . P 1
C24 C 1.120(3) 0.7277(8) 0.9291(5) 0.078(3) Uani 0.59(2) D U P 1
H26 H 1.168(3) 0.6847(8) 0.9682(5) 0.094(3) Uiso 0.59(2) R . P 1
C14 C 0.5440(10) 0.9318(4) 0.1089(2) 0.1181(16) Uani 1.000000 . . . .
H17 H 0.480(5) 0.967(2) 0.0637(6) 0.177(2) Uiso 1.000000 GR . . .
H18 H 0.7266(11) 0.952(2) 0.1160(7) 0.177(2) Uiso 1.000000 GR . . .
H16 H 0.500(6) 0.8606(5) 0.0928(12) 0.177(2) Uiso 1.000000 GR . . .
H20 H 0.887(6) 0.698(3) 0.621(2) 0.089(11) Uiso 1.000000 . . . .
C25A C 1.289(3) 0.7480(12) 0.8453(6) 0.066(3) Uani 0.41(2) D U P 2
H27A H 1.435(3) 0.7256(12) 0.8272(6) 0.079(4) Uiso 0.41(2) R . P 2
C24A C 1.228(4) 0.7467(15) 0.9298(8) 0.101(5) Uani 0.41(2) D U P 2
H26A H 1.330(4) 0.7209(15) 0.9691(8) 0.122(6) Uiso 0.41(2) R . P 2
C23A C 1.027(4) 0.7810(16) 0.9585(9) 0.069(4) Uani 0.41(2) D U P 2
H25A H 0.990(4) 0.7795(16) 1.0173(9) 0.083(4) Uiso 0.41(2) R . P 2
C22A C 0.870(3) 0.8195(18) 0.9005(8) 0.087(5) Uani 0.41(2) D U P 2
H24A H 0.734(3) 0.8478(18) 0.9206(8) 0.105(6) Uiso 0.41(2) R . P 2
C21A C 0.921(2) 0.8145(15) 0.8124(7) 0.068(4) Uani 0.41(2) D U P 2
H23A H 0.808(2) 0.8329(15) 0.7717(7) 0.081(4) Uiso 0.41(2) R . P 2


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
F2 C10 1.355(3) . ?
F1 C6 1.358(3) . ?
O2 C17 1.254(3) . ?
N2 C9 1.402(3) . ?
N2 C15 1.352(3) . ?
N2 C11 1.481(3) . ?
O3 C18 1.238(3) . ?
N1 C5 1.407(3) . ?
N1 C4 1.461(3) . ?
N1 C1 1.460(3) . ?
N3 C18 1.336(3) . ?
N3 C19 1.455(3) . ?
N3 H20 0.95(3) . ?
O1 C2 1.417(4) . ?
O1 C3 1.418(4) . ?
C8 C9 1.402(3) . ?
C8 C17 1.464(3) . ?
C8 C7 1.404(3) . ?
C9 C10 1.406(3) . ?
C17 C16 1.436(3) . ?
C5 C10 1.385(3) . ?
C5 C6 1.400(3) . ?
C16 C18 1.495(3) . ?
C16 C15 1.363(3) . ?
C7 H9 0.9400 . ?
C7 C6 1.358(3) . ?
C15 H19 0.9400 . ?
C20 C19 1.504(3) . ?
C20 C25 1.350(7) . ?
C20 C21 1.402(8) . ?
C20 C25A 1.407(10) . ?
C20 C21A 1.360(12) . ?
C11 H11 0.9800 . ?
C11 H10 0.9800 . ?
C11 C12 1.528(3) . ?
C19 H21 0.9800 . ?
C19 H22 0.9800 . ?
C12 H13 0.9800 . ?
C12 H12 0.9800 . ?
C12 C13 1.509(3) . ?
C4 H8 0.9800 . ?
C4 H7 0.9800 . ?
C4 C3 1.508(4) . ?
C1 H1 0.9800 . ?
C1 H2 0.9800 . ?
C1 C2 1.503(4) . ?
C2 H3 0.9800 . ?
C2 H4 0.9800 . ?
C3 H6 0.9800 . ?
C3 H5 0.9800 . ?
C13 H15 0.9800 . ?
C13 H14 0.9800 . ?
C13 C14 1.529(5) . ?
C23 H25 0.9400 . ?
C23 C22 1.337(12) . ?
C23 C24 1.384(12) . ?
C25 H27 0.9400 . ?
C25 C24 1.413(9) . ?
C21 H23 0.9400 . ?
C21 C22 1.371(10) . ?
C22 H24 0.9400 . ?
C24 H26 0.9400 . ?
C14 H17 0.9700 . ?
C14 H18 0.9700 . ?
C14 H16 0.9700 . ?
C25A H27A 0.9400 . ?
C25A C24A 1.360(13) . ?
C24A H26A 0.9400 . ?
C24A C23A 1.335(18) . ?
C23A H25A 0.9400 . ?
C23A C22A 1.411(17) . ?
C22A H24A 0.9400 . ?
C22A C21A 1.398(13) . ?
C21A H23A 0.9400 . ?

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
C15 N2 C9 118.74(19) . . ?
C11 N2 C9 123.04(18) . . ?
C11 N2 C15 117.32(19) . . ?
C4 N1 C5 119.94(19) . . ?
C1 N1 C5 116.18(19) . . ?
C1 N1 C4 112.2(2) . . ?
C19 N3 C18 123.4(2) . . ?
H20 N3 C18 115(2) . . ?
H20 N3 C19 121(2) . . ?
C3 O1 C2 109.7(2) . . ?
C17 C8 C9 121.8(2) . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 C17 117.8(2) . . ?
C8 C9 N2 119.28(19) . . ?
C10 C9 N2 123.9(2) . . ?
C10 C9 C8 116.8(2) . . ?
C8 C17 O2 120.2(2) . . ?
C16 C17 O2 124.6(2) . . ?
C16 C17 C8 115.3(2) . . ?
C10 C5 N1 124.9(2) . . ?
C6 C5 N1 119.8(2) . . ?
C6 C5 C10 115.1(2) . . ?
C9 C10 F2 119.4(2) . . ?
C5 C10 F2 116.44(19) . . ?
C5 C10 C9 124.2(2) . . ?
C18 C16 C17 123.7(2) . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 C18 116.6(2) . . ?
H9 C7 C8 120.40(13) . . ?
C6 C7 C8 119.2(2) . . ?
C6 C7 H9 120.40(14) . . ?
N3 C18 O3 123.6(2) . . ?
C16 C18 O3 121.3(2) . . ?
C16 C18 N3 115.1(2) . . ?
C16 C15 N2 125.3(2) . . ?
H19 C15 N2 117.37(13) . . ?
H19 C15 C16 117.37(13) . . ?
C5 C6 F1 117.3(2) . . ?
C7 C6 F1 118.8(2) . . ?
C7 C6 C5 123.8(2) . . ?
C25 C20 C19 123.6(4) . . ?
C21 C20 C19 119.4(4) . . ?
C21 C20 C25 117.0(5) . . ?
C25A C20 C19 116.2(6) . . ?
C25A C20 C25 24.0(5) . . ?
C25A C20 C21 118.5(6) . . ?
C21A C20 C19 124.4(5) . . ?
C21A C20 C25 107.1(6) . . ?
C21A C20 C21 25.1(6) . . ?
C21A C20 C25A 119.4(7) . . ?
H11 C11 N2 109.47(13) . . ?
H10 C11 N2 109.47(11) . . ?
H10 C11 H11 108.1 . . ?
C12 C11 N2 110.88(19) . . ?
C12 C11 H11 109.47(14) . . ?
C12 C11 H10 109.47(14) . . ?
C20 C19 N3 112.6(2) . . ?
H21 C19 N3 109.08(14) . . ?
H21 C19 C20 109.08(14) . . ?
H22 C19 N3 109.08(13) . . ?
H22 C19 C20 109.08(13) . . ?
H22 C19 H21 107.8 . . ?
H13 C12 C11 108.72(14) . . ?
H12 C12 C11 108.72(14) . . ?
H12 C12 H13 107.6 . . ?
C13 C12 C11 114.2(2) . . ?
C13 C12 H13 108.72(18) . . ?
C13 C12 H12 108.72(16) . . ?
H8 C4 N1 109.93(14) . . ?
H7 C4 N1 109.93(13) . . ?
H7 C4 H8 108.3 . . ?
C3 C4 N1 108.8(2) . . ?
C3 C4 H8 109.93(18) . . ?
C3 C4 H7 109.93(17) . . ?
H1 C1 N1 109.49(14) . . ?
H2 C1 N1 109.49(14) . . ?
H2 C1 H1 108.1 . . ?
C2 C1 N1 110.8(2) . . ?
C2 C1 H1 109.49(17) . . ?
C2 C1 H2 109.49(16) . . ?
C1 C2 O1 111.9(2) . . ?
H3 C2 O1 109.22(15) . . ?
H3 C2 C1 109.22(15) . . ?
H4 C2 O1 109.22(16) . . ?
H4 C2 C1 109.22(16) . . ?
H4 C2 H3 107.9 . . ?
C4 C3 O1 111.1(2) . . ?
H6 C3 O1 109.42(17) . . ?
H6 C3 C4 109.42(18) . . ?
H5 C3 O1 109.42(16) . . ?
H5 C3 C4 109.42(17) . . ?
H5 C3 H6 108.0 . . ?
H15 C13 C12 109.42(18) . . ?
H14 C13 C12 109.42(16) . . ?
H14 C13 H15 108.0 . . ?
C14 C13 C12 111.1(3) . . ?
C14 C13 H15 109.4(2) . . ?
C14 C13 H14 109.4(2) . . ?
C22 C23 H25 120.4(6) . . ?
C24 C23 H25 120.4(6) . . ?
C24 C23 C22 119.2(9) . . ?
H27 C25 C20 119.1(4) . . ?
C24 C25 C20 121.8(7) . . ?
C24 C25 H27 119.1(5) . . ?
H23 C21 C20 119.4(4) . . ?
C22 C21 C20 121.2(7) . . ?
C22 C21 H23 119.4(6) . . ?
C21 C22 C23 121.5(9) . . ?
H24 C22 C23 119.2(6) . . ?
H24 C22 C21 119.2(6) . . ?
C25 C24 C23 119.1(8) . . ?
H26 C24 C23 120.4(6) . . ?
H26 C24 C25 120.4(5) . . ?
H17 C14 C13 109.5 . . ?
H18 C14 C13 109.5 . . ?
H18 C14 H17 109.5 . . ?
H16 C14 C13 109.5 . . ?
H16 C14 H17 109.5 . . ?
H16 C14 H18 109.5 . . ?
H27A C25A C20 120.3(6) . . ?
C24A C25A C20 119.5(11) . . ?
C24A C25A H27A 120.3(8) . . ?
H26A C24A C25A 119.0(8) . . ?
C23A C24A C25A 122.0(12) . . ?
C23A C24A H26A 119.0(8) . . ?
H25A C23A C24A 120.0(8) . . ?
C22A C23A C24A 120.0(13) . . ?
C22A C23A H25A 120.0(9) . . ?
H24A C22A C23A 120.8(9) . . ?
C21A C22A C23A 118.4(13) . . ?
C21A C22A H24A 120.8(8) . . ?
C22A C21A C20 120.4(11) . . ?
H23A C21A C20 119.8(5) . . ?
H23A C21A C22A 119.8(8) . . ?

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
F2 C10 C9 N2 -7.9(3) . . . . ?
F2 C10 C9 C8 173.5(2) . . . . ?
F2 C10 C5 N1 12.0(3) . . . . ?
F2 C10 C5 C6 -172.6(2) . . . . ?
F1 C6 C5 N1 -3.3(2) . . . . ?
F1 C6 C5 C10 -178.9(2) . . . . ?
F1 C6 C7 C8 173.1(2) . . . . ?
O2 C17 C8 C9 179.5(2) . . . . ?
O2 C17 C8 C7 -3.8(3) . . . . ?
O2 C17 C16 C18 2.4(3) . . . . ?
O2 C17 C16 C15 -179.3(2) . . . . ?
N2 C9 C8 C17 -0.9(2) . . . . ?
N2 C9 C8 C7 -177.5(2) . . . . ?
N2 C9 C10 C5 171.1(2) . . . . ?
N2 C15 C16 C17 0.5(3) . . . . ?
N2 C15 C16 C18 179.0(2) . . . . ?
N2 C11 C12 C13 160.3(2) . . . . ?
O3 C18 N3 C19 1.1(3) . . . . ?
O3 C18 C16 C17 -178.1(2) . . . . ?
O3 C18 C16 C15 3.5(3) . . . . ?
N1 C5 C10 C9 -167.0(2) . . . . ?
N1 C5 C6 C7 172.5(2) . . . . ?
N1 C4 C3 O1 59.2(2) . . . . ?
N1 C1 C2 O1 -53.9(2) . . . . ?
N3 C18 C16 C17 1.9(3) . . . . ?
N3 C18 C16 C15 -176.6(2) . . . . ?
N3 C19 C20 C25 120.2(7) . . . . ?
N3 C19 C20 C21 -60.8(8) . . . . ?
N3 C19 C20 C25A 146.7(9) . . . . ?
N3 C19 C20 C21A -31.7(10) . . . . ?
C8 C9 C10 C5 -7.5(2) . . . . ?
C8 C17 C16 C18 -176.97(18) . . . . ?
C8 C17 C16 C15 1.4(2) . . . . ?
C8 C7 C6 C5 -2.7(3) . . . . ?
C9 C10 C5 C6 8.4(3) . . . . ?
C20 C25 C24 C23 1.6(15) . . . . ?
C20 C21 C22 C23 3.3(18) . . . . ?
C20 C25A C24A C23A -2(2) . . . . ?
C20 C21A C22A C23A -7(2) . . . . ?
C11 C12 C13 C14 178.8(3) . . . . ?
C25A C24A C23A C22A 0(3) . . . . ?
C24A C23A C22A C21A 4(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C20 C25 1 1
C20 C21 1 2
C20 C22 1 7
C20 C24 1 8
C20 C25A 1 1
C20 C24A 1 8
C20 C22A 1 7
C20 C21A 1 2
C23 C25 1 9
C23 C21 1 10
C23 C22 1 3
C23 C24 1 4
C25 C24 1 5
C21 C22 1 6
C22 C24 1 11
C25A C24A 1 5
C23A C25A 1 9
C23A C24A 1 4
C23A C22A 1 3
C23A C21A 1 10
C22A C24A 1 11
C21A C22A 1 6

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.3784 0.0289 0.0289
2 0.0200 1.3813 0.0208 0.0208
3 0.0200 1.3737 0.0368 0.0368
4 0.0200 1.3592 0.0243 0.0243
5 0.0200 1.3864 0.0263 0.0263
6 0.0200 1.3846 0.0134 0.0134
7 0.0400 2.4052 0.0114 0.0114
8 0.0400 2.4021 0.0119 0.0119
9 0.0400 2.3841 0.0270 0.0270
10 0.0400 2.3876 0.0243 0.0243
11 0.0400 2.3625 0.0156 0.0156

loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
C20 C19 0.004000 0.003142 0.000517 -0.000810
C20 C19 0.004000 0.003142 0.000517 -0.000810
C20 C25 0.004000 0.003654 -0.004603 -0.001093
C20 C21 0.004000 -0.000331 -0.002092 0.004324
C20 C22 0.004000 -0.004115 -0.006189 0.001904
C20 C24 0.004000 -0.000460 -0.008523 -0.002424
C20 C25A 0.004000 -0.003386 0.000805 -0.001474
C20 C24A 0.004000 -0.000503 -0.006877 -0.006474
C20 C22A 0.004000 0.010252 -0.001447 -0.003261
C20 C21A 0.004000 0.007816 -0.003742 -0.001547
C19 C25 0.004000 0.004285 -0.009867 -0.002675
C19 C21 0.004000 -0.001833 -0.004705 -0.000193
C19 C25A 0.004000 0.004851 0.002086 -0.001415
C19 C21A 0.004000 0.006645 -0.006249 -0.002446
C23 C25 0.004000 0.005984 0.005491 -0.006212
C23 C21 0.004000 -0.007632 -0.001118 0.004343
C23 C22 0.004000 -0.005062 -0.010686 -0.000563
C23 C24 0.004000 0.008547 -0.000566 -0.005501
C25 C21 0.004000 -0.002411 -0.005584 0.000429
C25 C24 0.004000 0.003491 -0.004440 0.003400
C21 C22 0.004000 -0.005204 -0.002083 -0.003405
C22 C24 0.004000 -0.009139 0.017196 -0.000566
C25A C24A 0.004000 0.004231 0.000400 -0.000912
C25A C23A 0.004000 0.012992 0.012840 -0.002065
C25A C21A 0.004000 0.002319 0.011324 0.002127
C24A C23A 0.004000 0.004323 0.004858 0.000697
C24A C22A 0.004000 -0.000106 0.017189 0.002996
C23A C22A 0.004000 -0.010064 0.005393 -0.008456
C23A C21A 0.004000 -0.005879 0.005642 -0.004792
C22A C21A 0.004000 -0.001187 0.006369 -0.000466

