# Supplementary Information (SI) for CrystEngComm.
# 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. 
# 
#######################################################################

data_KB1415_0m
_database_code_depnum_ccdc_archive 'CCDC 2494433'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-12-31 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        Ivacaftor
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O3'
_chemical_formula_sum            'C24 H28 N2 O3'
_chemical_formula_weight         392.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.867(2)
_cell_length_b                   5.9451(11)
_cell_length_c                   14.816(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.328(7)
_cell_angle_gamma                90
_cell_volume                     1008.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3227
_cell_measurement_theta_min      2.506
_cell_measurement_theta_max      23.56

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6091
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            17200
_diffrn_reflns_av_unetI/netI     0.0942
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.851
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3523
_reflns_number_gt                2380
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3523
_refine_ls_number_parameters     279
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7265(4) 1.3364(8) 0.2603(3) 0.0247(11) Uani 1 1 d . . . . .
H1 H 0.770097 1.423546 0.311428 0.030 Uiso 1 1 calc R U . . .
C2 C 0.7236(4) 1.3954(8) 0.1702(3) 0.0285(12) Uani 1 1 d . . . . .
H2 H 0.764521 1.525427 0.159125 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6613(4) 1.2665(8) 0.0946(3) 0.0252(11) Uani 1 1 d . . . . .
H3 H 0.660619 1.308773 0.032662 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6017(3) 1.0809(8) 0.1093(3) 0.0230(11) Uani 1 1 d . . . . .
H4 H 0.559940 0.993989 0.057363 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6010(3) 1.0157(7) 0.2008(3) 0.0204(11) Uani 1 1 d . . . . .
C6 C 0.6644(3) 1.1464(8) 0.2763(3) 0.0204(11) Uani 1 1 d . . . . .
C7 C 0.6042(4) 0.9050(8) 0.3826(3) 0.0225(11) Uani 1 1 d . . . . .
H7 H 0.605831 0.871626 0.445630 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5412(3) 0.7663(7) 0.3131(3) 0.0190(11) Uani 1 1 d . . . . .
C9 C 0.5344(3) 0.8187(8) 0.2165(3) 0.0204(11) Uani 1 1 d . . . . .
C10 C 0.4795(3) 0.5769(8) 0.3441(3) 0.0215(11) Uani 1 1 d . . . . .
C11 C 0.3273(3) 0.2841(7) 0.2860(3) 0.0180(10) Uani 1 1 d . . . . .
C12 C 0.3456(4) 0.1712(7) 0.3702(3) 0.0207(11) Uani 1 1 d . . . . .
H12 H 0.416711 0.195527 0.416803 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2643(3) 0.0239(7) 0.3893(3) 0.0199(11) Uani 1 1 d . . . . .
C14 C 0.1577(3) -0.0152(7) 0.3225(3) 0.0198(11) Uani 1 1 d . . . . .
C15 C 0.1474(3) 0.0877(8) 0.2362(3) 0.0194(10) Uani 1 1 d . . . . .
H15 H 0.078697 0.054383 0.188181 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2269(3) 0.2343(7) 0.2125(3) 0.0171(10) Uani 1 1 d . . . . .
C17 C 0.0592(4) -0.1529(8) 0.3437(3) 0.0234(11) Uani 1 1 d . . . . .
C18 C 0.0210(4) -0.0446(8) 0.4254(3) 0.0290(12) Uani 1 1 d . . . . .
H18A H -0.007923 0.107899 0.407780 0.043 Uiso 1 1 calc R U . . .
H18B H 0.087934 -0.037722 0.480704 0.043 Uiso 1 1 calc R U . . .
H18C H -0.041203 -0.135035 0.439511 0.043 Uiso 1 1 calc R U . . .
C19 C 0.0970(4) -0.3964(8) 0.3675(3) 0.0285(11) Uani 1 1 d . . . . .
H19A H 0.118299 -0.465474 0.314217 0.043 Uiso 1 1 calc R U . . .
H19B H 0.032449 -0.480677 0.381082 0.043 Uiso 1 1 calc R U . . .
H19C H 0.164598 -0.399201 0.422409 0.043 Uiso 1 1 calc R U . . .
C20 C -0.0502(4) -0.1590(9) 0.2604(3) 0.0299(12) Uani 1 1 d . . . . .
H20A H -0.075449 -0.004920 0.241910 0.045 Uiso 1 1 calc R U . . .
H20B H -0.112964 -0.239321 0.278470 0.045 Uiso 1 1 calc R U . . .
H20C H -0.031893 -0.236608 0.207635 0.045 Uiso 1 1 calc R U . . .
C21 C 0.2054(3) 0.3258(8) 0.1128(3) 0.0185(10) Uani 1 1 d . . . . .
C22 C 0.1887(4) 0.5834(8) 0.1095(3) 0.0252(11) Uani 1 1 d . . . . .
H22A H 0.180429 0.637194 0.045563 0.038 Uiso 1 1 calc R U . . .
H22B H 0.256829 0.654985 0.151922 0.038 Uiso 1 1 calc R U . . .
H22C H 0.118319 0.621643 0.128984 0.038 Uiso 1 1 calc R U . . .
C23 C 0.3060(3) 0.2539(8) 0.0708(3) 0.0236(11) Uani 1 1 d . . . . .
H23A H 0.284866 0.288179 0.003748 0.035 Uiso 1 1 calc R U . . .
H23B H 0.319601 0.091880 0.079969 0.035 Uiso 1 1 calc R U . . .
H23C H 0.377204 0.335907 0.102118 0.035 Uiso 1 1 calc R U . . .
C24 C 0.0943(3) 0.2271(8) 0.0467(3) 0.0265(11) Uani 1 1 d . . . . .
H24A H 0.086388 0.282135 -0.016979 0.040 Uiso 1 1 calc R U . . .
H24B H 0.026030 0.273538 0.067613 0.040 Uiso 1 1 calc R U . . .
H24C H 0.099501 0.062526 0.047433 0.040 Uiso 1 1 calc R U . . .
N1 N 0.6633(3) 1.0847(7) 0.3656(3) 0.0247(10) Uani 1 1 d . . . . .
H1N H 0.692(4) 1.184(9) 0.410(3) 0.042(16) Uiso 1 1 d . . . . .
N2 N 0.4079(3) 0.4526(6) 0.2751(2) 0.0197(9) Uani 1 1 d . . . . .
H2N H 0.407(3) 0.507(7) 0.218(3) 0.024 Uiso 1 1 d . U . . .
O1 O 0.4743(2) 0.7076(5) 0.14844(17) 0.0253(8) Uani 1 1 d . . . . .
O2 O 0.4928(2) 0.5389(6) 0.42851(19) 0.0283(8) Uani 1 1 d . . . . .
O3 O 0.2885(3) -0.0759(6) 0.47655(19) 0.0283(8) Uani 1 1 d . . . . .
H3O H 0.360(5) -0.024(11) 0.507(4) 0.08(2) 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
C1 C2 1.372(6) . ?
C1 C6 1.403(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.359(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(5) . ?
C5 C9 1.466(6) . ?
C6 N1 1.376(5) . ?
C7 N1 1.338(6) . ?
C7 C8 1.376(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.445(5) . ?
C8 C10 1.481(6) . ?
C9 O1 1.258(5) . ?
C10 O2 1.240(4) . ?
C10 N2 1.361(5) . ?
C11 C12 1.382(5) . ?
C11 C16 1.417(5) . ?
C11 N2 1.423(5) . ?
C12 C13 1.386(6) . ?
C12 H12 0.9500 . ?
C13 O3 1.382(5) . ?
C13 C14 1.404(5) . ?
C14 C15 1.394(5) . ?
C14 C17 1.526(6) . ?
C15 C16 1.395(6) . ?
C15 H15 0.9500 . ?
C16 C21 1.531(5) . ?
C17 C19 1.529(6) . ?
C17 C20 1.537(5) . ?
C17 C18 1.541(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C24 1.536(5) . ?
C21 C22 1.544(6) . ?
C21 C23 1.544(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 H1N 0.88(5) . ?
N2 H2N 0.90(4) . ?
O3 H3O 0.90(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 C1 C6 119.4(4) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C1 C2 C3 120.8(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.4(4) . . ?
C6 C5 C9 120.8(4) . . ?
C4 C5 C9 120.8(4) . . ?
N1 C6 C1 121.1(4) . . ?
N1 C6 C5 118.6(4) . . ?
C1 C6 C5 120.3(4) . . ?
N1 C7 C8 123.1(4) . . ?
N1 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 C10 116.0(4) . . ?
C9 C8 C10 124.6(4) . . ?
O1 C9 C8 123.5(4) . . ?
O1 C9 C5 120.5(4) . . ?
C8 C9 C5 116.0(4) . . ?
O2 C10 N2 123.1(4) . . ?
O2 C10 C8 120.7(4) . . ?
N2 C10 C8 116.2(4) . . ?
C12 C11 C16 119.4(4) . . ?
C12 C11 N2 119.6(3) . . ?
C16 C11 N2 120.9(4) . . ?
C11 C12 C13 122.7(4) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
O3 C13 C12 118.6(3) . . ?
O3 C13 C14 120.9(4) . . ?
C12 C13 C14 120.4(4) . . ?
C15 C14 C13 114.7(4) . . ?
C15 C14 C17 122.5(3) . . ?
C13 C14 C17 122.7(4) . . ?
C16 C15 C14 127.1(4) . . ?
C16 C15 H15 116.4 . . ?
C14 C15 H15 116.4 . . ?
C15 C16 C11 115.1(4) . . ?
C15 C16 C21 120.9(3) . . ?
C11 C16 C21 124.0(4) . . ?
C14 C17 C19 111.2(4) . . ?
C14 C17 C20 112.2(3) . . ?
C19 C17 C20 107.3(4) . . ?
C14 C17 C18 109.7(3) . . ?
C19 C17 C18 110.1(4) . . ?
C20 C17 C18 106.2(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 C24 112.0(3) . . ?
C16 C21 C22 111.7(3) . . ?
C24 C21 C22 106.1(3) . . ?
C16 C21 C23 110.0(3) . . ?
C24 C21 C23 105.2(3) . . ?
C22 C21 C23 111.6(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 N1 C6 122.2(4) . . ?
C7 N1 H1N 120(3) . . ?
C6 N1 H1N 116(3) . . ?
C10 N2 C11 127.0(3) . . ?
C10 N2 H2N 111(3) . . ?
C11 N2 H2N 121(3) . . ?
C13 O3 H3O 105(4) . . ?

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
C6 C1 C2 C3 -1.0(6) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C3 C4 C5 C9 178.5(4) . . . . ?
C2 C1 C6 N1 -178.7(4) . . . . ?
C2 C1 C6 C5 0.8(6) . . . . ?
C4 C5 C6 N1 179.5(4) . . . . ?
C9 C5 C6 N1 0.4(6) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C9 C5 C6 C1 -179.1(4) . . . . ?
N1 C7 C8 C9 -2.1(6) . . . . ?
N1 C7 C8 C10 -179.1(4) . . . . ?
C7 C8 C9 O1 -176.4(4) . . . . ?
C10 C8 C9 O1 0.3(6) . . . . ?
C7 C8 C9 C5 2.4(5) . . . . ?
C10 C8 C9 C5 179.2(4) . . . . ?
C6 C5 C9 O1 177.2(4) . . . . ?
C4 C5 C9 O1 -1.8(6) . . . . ?
C6 C5 C9 C8 -1.6(5) . . . . ?
C4 C5 C9 C8 179.3(4) . . . . ?
C7 C8 C10 O2 -5.5(6) . . . . ?
C9 C8 C10 O2 177.7(4) . . . . ?
C7 C8 C10 N2 173.7(4) . . . . ?
C9 C8 C10 N2 -3.1(6) . . . . ?
C16 C11 C12 C13 -5.9(6) . . . . ?
N2 C11 C12 C13 172.5(4) . . . . ?
C11 C12 C13 O3 -178.0(4) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
O3 C13 C14 C15 -177.1(4) . . . . ?
C12 C13 C14 C15 5.5(6) . . . . ?
O3 C13 C14 C17 4.9(6) . . . . ?
C12 C13 C14 C17 -172.5(4) . . . . ?
C13 C14 C15 C16 -4.8(7) . . . . ?
C17 C14 C15 C16 173.3(4) . . . . ?
C14 C15 C16 C11 -1.1(7) . . . . ?
C14 C15 C16 C21 177.3(4) . . . . ?
C12 C11 C16 C15 6.4(6) . . . . ?
N2 C11 C16 C15 -171.9(4) . . . . ?
C12 C11 C16 C21 -171.9(4) . . . . ?
N2 C11 C16 C21 9.8(6) . . . . ?
C15 C14 C17 C19 119.1(4) . . . . ?
C13 C14 C17 C19 -63.0(5) . . . . ?
C15 C14 C17 C20 -1.1(6) . . . . ?
C13 C14 C17 C20 176.8(4) . . . . ?
C15 C14 C17 C18 -118.9(4) . . . . ?
C13 C14 C17 C18 59.0(5) . . . . ?
C15 C16 C21 C24 -3.0(6) . . . . ?
C11 C16 C21 C24 175.2(4) . . . . ?
C15 C16 C21 C22 115.9(5) . . . . ?
C11 C16 C21 C22 -65.9(5) . . . . ?
C15 C16 C21 C23 -119.6(4) . . . . ?
C11 C16 C21 C23 58.6(5) . . . . ?
C8 C7 N1 C6 0.8(6) . . . . ?
C1 C6 N1 C7 179.6(4) . . . . ?
C5 C6 N1 C7 0.1(6) . . . . ?
O2 C10 N2 C11 8.7(7) . . . . ?
C8 C10 N2 C11 -170.5(4) . . . . ?
C12 C11 N2 C10 -25.0(6) . . . . ?
C16 C11 N2 C10 153.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 O2 0.95 2.64 3.391(5) 135.8 2_656 yes
C12 H12 O2 0.95 2.44 3.189(5) 135.2 2_646 yes
O3 H3O O2 0.90(6) 1.80(6) 2.692(4) 172(6) 2_646 yes
N1 H1N O3 0.88(5) 2.17(5) 3.027(5) 164(4) 2_666 yes
N2 H2N O1 0.90(4) 1.89(4) 2.687(5) 147(4) . yes
C12 H12 O2 0.95 2.22 2.789(5) 117.5 . yes

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitromethane'
####################################################################### 
# 
# 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_kb1784_0m_sx
_database_code_depnum_ccdc_archive 'CCDC 2494435'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor-geranil monohydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O3, C10 H18 O, H2 O'
_chemical_formula_sum            'C34 H48 N2 O5'
_chemical_formula_weight         564.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.159(6)
_cell_length_b                   9.147(5)
_cell_length_c                   23.118(16)
_cell_angle_alpha                84.592(13)
_cell_angle_beta                 81.785(15)
_cell_angle_gamma                68.743(11)
_cell_volume                     1589.6(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5844
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      26.06

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5990
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?


_diffrn_reflns_number            22630
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.514
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6385
_reflns_number_gt                3856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1059P)²+0.8541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6385
_refine_ls_number_parameters     404
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.2142
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7010(4) -0.0342(3) 0.52846(12) 0.0201(7) Uani 1 1 d . . . . .
C2 C 0.6373(4) -0.1236(3) 0.57268(13) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.564697 -0.075235 0.606550 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6817(4) -0.2824(3) 0.56625(13) 0.0242(7) Uani 1 1 d . . . . .
H3 H 0.640163 -0.343629 0.596082 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7873(4) -0.3539(3) 0.51614(13) 0.0240(7) Uani 1 1 d . . . . .
H4 H 0.815054 -0.462779 0.511779 0.029 Uiso 1 1 calc R U . . .
C5 C 0.8508(4) -0.2668(3) 0.47327(13) 0.0231(7) Uani 1 1 d . . . . .
H5 H 0.922976 -0.316593 0.439562 0.028 Uiso 1 1 calc R U . . .
C6 C 0.8105(4) -0.1050(3) 0.47851(12) 0.0202(7) Uani 1 1 d . . . . .
C7 C 0.8794(4) -0.0111(3) 0.43302(12) 0.0202(7) Uani 1 1 d . . . . .
C8 C 0.8177(4) 0.1554(3) 0.44157(12) 0.0202(7) Uani 1 1 d . . . . .
C9 C 0.7100(4) 0.2151(3) 0.49179(12) 0.0215(7) Uani 1 1 d . . . . .
H9 H 0.672525 0.324763 0.496844 0.026 Uiso 1 1 calc R U . . .
C10 C 0.8507(4) 0.2745(3) 0.39673(13) 0.0205(7) Uani 1 1 d . . . . .
C11 C 0.9597(4) 0.3082(3) 0.29224(12) 0.0194(6) Uani 1 1 d . . . . .
C12 C 1.0599(4) 0.4032(3) 0.29233(13) 0.0210(7) Uani 1 1 d . . . . .
H12 H 1.102286 0.411574 0.327623 0.025 Uiso 1 1 calc R U . . .
C13 C 1.0996(4) 0.4860(3) 0.24212(13) 0.0217(7) Uani 1 1 d . . . . .
C14 C 1.0431(4) 0.4706(3) 0.18849(13) 0.0214(7) Uani 1 1 d . . . . .
C15 C 0.9413(4) 0.3756(3) 0.19076(13) 0.0221(7) Uani 1 1 d . . . . .
H15 H 0.902270 0.364338 0.155191 0.026 Uiso 1 1 calc R U . . .
C16 C 0.8913(4) 0.2949(3) 0.24115(13) 0.0213(7) Uani 1 1 d . . . . .
C17 C 0.7645(4) 0.2051(3) 0.23870(13) 0.0249(7) Uani 1 1 d . . . . .
C18 C 0.6004(5) 0.2686(4) 0.28380(16) 0.0388(9) Uani 1 1 d . . . . .
H18A H 0.549586 0.383259 0.278693 0.058 Uiso 1 1 calc R U . . .
H18B H 0.634913 0.239829 0.323386 0.058 Uiso 1 1 calc R U . . .
H18C H 0.512340 0.223299 0.278040 0.058 Uiso 1 1 calc R U . . .
C19 C 0.8573(5) 0.0269(4) 0.24856(15) 0.0347(8) Uani 1 1 d . . . . .
H19A H 0.776176 -0.026794 0.243599 0.052 Uiso 1 1 calc R U . . .
H19B H 0.891757 0.004003 0.288274 0.052 Uiso 1 1 calc R U . . .
H19C H 0.963105 -0.010093 0.220100 0.052 Uiso 1 1 calc R U . . .
C20 C 0.6985(5) 0.2286(4) 0.17798(15) 0.0374(9) Uani 1 1 d . . . . .
H20A H 0.799015 0.182862 0.148387 0.056 Uiso 1 1 calc R U . . .
H20B H 0.642513 0.341158 0.168572 0.056 Uiso 1 1 calc R U . . .
H20C H 0.612131 0.176861 0.178422 0.056 Uiso 1 1 calc R U . . .
C21 C 1.0893(4) 0.5534(3) 0.13071(13) 0.0243(7) Uani 1 1 d . . . . .
C22 C 1.0179(5) 0.7328(3) 0.13682(14) 0.0290(8) Uani 1 1 d . . . . .
H22A H 1.042395 0.784526 0.099217 0.043 Uiso 1 1 calc R U . . .
H22B H 1.076097 0.758775 0.166561 0.043 Uiso 1 1 calc R U . . .
H22C H 0.889793 0.769220 0.148552 0.043 Uiso 1 1 calc R U . . .
C23 C 1.0068(5) 0.5217(4) 0.07958(13) 0.0321(8) Uani 1 1 d . . . . .
H23A H 1.037064 0.578498 0.044042 0.048 Uiso 1 1 calc R U . . .
H23B H 0.877749 0.557567 0.088943 0.048 Uiso 1 1 calc R U . . .
H23C H 1.052933 0.408832 0.073185 0.048 Uiso 1 1 calc R U . . .
C24 C 1.2909(4) 0.4939(4) 0.11503(14) 0.0316(8) Uani 1 1 d . . . . .
H24A H 1.334799 0.380233 0.110465 0.047 Uiso 1 1 calc R U . . .
H24B H 1.345888 0.517088 0.146316 0.047 Uiso 1 1 calc R U . . .
H24C H 1.320759 0.546369 0.078272 0.047 Uiso 1 1 calc R U . . .
N1 N 0.6553(4) 0.1260(3) 0.53394(11) 0.0211(6) Uani 1 1 d . . . . .
H1N H 0.571(5) 0.182(4) 0.5657(15) 0.040(10) Uiso 1 1 d . . . . .
N2 N 0.9350(4) 0.2179(3) 0.34468(10) 0.0211(6) Uani 1 1 d . . . . .
H2N H 0.974(5) 0.114(4) 0.3453(14) 0.034(9) Uiso 1 1 d . . . . .
O1 O 0.9818(3) -0.0757(2) 0.38913(9) 0.0269(5) Uani 1 1 d . . . . .
O2 O 0.7941(3) 0.4166(2) 0.40773(9) 0.0273(5) Uani 1 1 d . . . . .
O3 O 1.1951(3) 0.5823(2) 0.24349(10) 0.0277(5) Uani 1 1 d . . . . .
H3O H 1.212(5) 0.594(4) 0.2797(17) 0.050(12) Uiso 1 1 d . . . . .
C25 C 0.6582(4) 0.7613(3) 0.32946(12) 0.0244(7) Uani 1 1 d . . . . .
H25A H 0.786677 0.714596 0.332956 0.029 Uiso 1 1 calc R U . . .
H25B H 0.620058 0.875744 0.334169 0.029 Uiso 1 1 calc R U . . .
C26 C 0.6256(4) 0.7328(3) 0.27000(13) 0.0236(7) Uani 1 1 d . . . . .
H26 H 0.708913 0.643387 0.251048 0.028 Uiso 1 1 calc R U . . .
C27 C 0.4902(4) 0.8219(3) 0.24141(13) 0.0236(7) Uani 1 1 d . . . . .
C28 C 0.3447(5) 0.9672(4) 0.26509(15) 0.0347(8) Uani 1 1 d . . . . .
H28A H 0.345376 1.058651 0.239452 0.052 Uiso 1 1 calc R U . . .
H28B H 0.364398 0.982755 0.304530 0.052 Uiso 1 1 calc R U . . .
H28C H 0.230005 0.954320 0.266647 0.052 Uiso 1 1 calc R U . . .
C29 C 0.4701(5) 0.7767(4) 0.18213(13) 0.0271(7) Uani 1 1 d . . . . .
H29A H 0.355999 0.759849 0.184792 0.032 Uiso 1 1 calc R U . . .
H29B H 0.565886 0.675771 0.172396 0.032 Uiso 1 1 calc R U . . .
C30 C 0.4756(5) 0.8986(4) 0.13204(13) 0.0306(8) Uani 1 1 d . . . . .
H30A H 0.376013 0.998447 0.140172 0.037 Uiso 1 1 calc R U . . .
H30B H 0.587442 0.919219 0.129798 0.037 Uiso 1 1 calc R U . . .
C31 C 0.4631(5) 0.8418(4) 0.07447(13) 0.0302(8) Uani 1 1 d . . . . .
H31 H 0.553995 0.746383 0.062769 0.036 Uiso 1 1 calc R U . . .
C32 C 0.3427(5) 0.9066(4) 0.03776(14) 0.0304(8) Uani 1 1 d . . . . .
C33 C 0.1920(5) 1.0605(4) 0.04671(16) 0.0435(10) Uani 1 1 d . . . . .
H33A H 0.201449 1.134901 0.014169 0.065 Uiso 1 1 calc R U . . .
H33B H 0.197024 1.102849 0.083533 0.065 Uiso 1 1 calc R U . . .
H33C H 0.079293 1.043879 0.048258 0.065 Uiso 1 1 calc R U . . .
C34 C 0.3465(5) 0.8283(4) -0.01741(14) 0.0414(9) Uani 1 1 d . . . . .
H34A H 0.347026 0.901371 -0.051237 0.062 Uiso 1 1 calc R U . . .
H34B H 0.241609 0.798697 -0.014790 0.062 Uiso 1 1 calc R U . . .
H34C H 0.453491 0.734153 -0.021972 0.062 Uiso 1 1 calc R U . . .
O4 O 0.5628(3) 0.6935(3) 0.37557(9) 0.0265(5) Uani 1 1 d . . . . .
H4O H 0.633(6) 0.604(5) 0.385(2) 0.074(16) Uiso 1 1 d . . . . .
O1W O 1.2451(3) 0.6391(3) 0.35341(10) 0.0275(5) Uani 1 1 d D . . . .
H1W H 1.345(4) 0.655(5) 0.3567(18) 0.062(13) Uiso 1 1 d D . . . .
H2W H 1.154(4) 0.719(3) 0.3662(16) 0.053(13) Uiso 1 1 d 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
C1 N1 1.389(4) . ?
C1 C6 1.406(4) . ?
C1 C2 1.408(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.473(4) . ?
C7 O1 1.261(3) . ?
C7 C8 1.444(4) . ?
C8 C9 1.378(4) . ?
C8 C10 1.501(4) . ?
C9 N1 1.342(4) . ?
C9 H9 0.9500 . ?
C10 O2 1.249(3) . ?
C10 N2 1.346(4) . ?
C11 C12 1.392(4) . ?
C11 C16 1.410(4) . ?
C11 N2 1.434(4) . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 O3 1.376(3) . ?
C13 C14 1.418(4) . ?
C14 C15 1.397(4) . ?
C14 C21 1.540(4) . ?
C15 C16 1.410(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.545(4) . ?
C17 C19 1.539(4) . ?
C17 C18 1.539(5) . ?
C17 C20 1.543(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C24 1.533(5) . ?
C21 C23 1.539(4) . ?
C21 C22 1.542(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 H1N 0.97(4) . ?
N2 H2N 0.89(3) . ?
O3 H3O 0.89(4) . ?
C25 O4 1.455(3) . ?
C25 C26 1.500(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.332(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.511(4) . ?
C27 C29 1.515(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.537(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.503(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.326(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.504(5) . ?
C32 C34 1.512(5) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
O4 H4O 0.84(5) . ?
O1W H1W 0.889(19) . ?
O1W H2W 0.871(19) . ?

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
N1 C1 C6 119.3(3) . . ?
N1 C1 C2 119.9(3) . . ?
C6 C1 C2 120.8(3) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 120.5(3) . . ?
C5 C6 C7 121.4(3) . . ?
O1 C7 C8 123.8(3) . . ?
O1 C7 C6 120.4(3) . . ?
C8 C7 C6 115.8(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 C10 115.8(3) . . ?
C7 C8 C10 124.3(3) . . ?
N1 C9 C8 123.3(3) . . ?
N1 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
O2 C10 N2 124.0(3) . . ?
O2 C10 C8 120.4(3) . . ?
N2 C10 C8 115.5(2) . . ?
C12 C11 C16 121.1(3) . . ?
C12 C11 N2 118.4(3) . . ?
C16 C11 N2 120.5(2) . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
O3 C13 C12 120.8(3) . . ?
O3 C13 C14 119.2(2) . . ?
C12 C13 C14 120.0(3) . . ?
C15 C14 C13 116.1(3) . . ?
C15 C14 C21 121.2(3) . . ?
C13 C14 C21 122.7(3) . . ?
C14 C15 C16 125.8(3) . . ?
C14 C15 H15 117.1 . . ?
C16 C15 H15 117.1 . . ?
C11 C16 C15 115.2(3) . . ?
C11 C16 C17 124.3(3) . . ?
C15 C16 C17 120.5(3) . . ?
C19 C17 C18 111.1(3) . . ?
C19 C17 C20 105.9(3) . . ?
C18 C17 C20 107.2(3) . . ?
C19 C17 C16 111.7(3) . . ?
C18 C17 C16 109.7(3) . . ?
C20 C17 C16 111.1(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 C21 C23 108.1(3) . . ?
C24 C21 C14 109.2(2) . . ?
C23 C21 C14 112.2(2) . . ?
C24 C21 C22 110.0(3) . . ?
C23 C21 C22 107.0(3) . . ?
C14 C21 C22 110.2(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C1 121.2(3) . . ?
C9 N1 H1N 116(2) . . ?
C1 N1 H1N 122(2) . . ?
C10 N2 C11 126.6(2) . . ?
C10 N2 H2N 112(2) . . ?
C11 N2 H2N 121(2) . . ?
C13 O3 H3O 113(2) . . ?
O4 C25 C26 111.4(2) . . ?
O4 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
O4 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C27 C26 C25 125.8(3) . . ?
C27 C26 H26 117.1 . . ?
C25 C26 H26 117.1 . . ?
C26 C27 C28 124.3(3) . . ?
C26 C27 C29 120.4(3) . . ?
C28 C27 C29 115.3(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 C30 114.5(2) . . ?
C27 C29 H29A 108.6 . . ?
C30 C29 H29A 108.6 . . ?
C27 C29 H29B 108.6 . . ?
C30 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C31 C30 C29 111.1(3) . . ?
C31 C30 H30A 109.4 . . ?
C29 C30 H30A 109.4 . . ?
C31 C30 H30B 109.4 . . ?
C29 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
C32 C31 C30 128.9(3) . . ?
C32 C31 H31 115.6 . . ?
C30 C31 H31 115.6 . . ?
C31 C32 C33 124.2(3) . . ?
C31 C32 C34 121.6(3) . . ?
C33 C32 C34 114.2(3) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C25 O4 H4O 107(3) . . ?
H1W O1W H2W 110(4) . . ?

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
N1 C1 C2 C3 179.1(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
N1 C1 C6 C5 -178.3(3) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
N1 C1 C6 C7 1.3(4) . . . . ?
C2 C1 C6 C7 -178.8(3) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
C1 C6 C7 O1 177.9(3) . . . . ?
C5 C6 C7 O1 -2.6(4) . . . . ?
C1 C6 C7 C8 -4.0(4) . . . . ?
C5 C6 C7 C8 175.6(3) . . . . ?
O1 C7 C8 C9 -178.1(3) . . . . ?
C6 C7 C8 C9 3.8(4) . . . . ?
O1 C7 C8 C10 7.1(5) . . . . ?
C6 C7 C8 C10 -171.0(3) . . . . ?
C7 C8 C9 N1 -1.0(5) . . . . ?
C10 C8 C9 N1 174.2(3) . . . . ?
C9 C8 C10 O2 5.6(4) . . . . ?
C7 C8 C10 O2 -179.4(3) . . . . ?
C9 C8 C10 N2 -171.1(3) . . . . ?
C7 C8 C10 N2 3.9(4) . . . . ?
C16 C11 C12 C13 -1.3(5) . . . . ?
N2 C11 C12 C13 175.7(3) . . . . ?
C11 C12 C13 O3 178.4(3) . . . . ?
C11 C12 C13 C14 -2.3(5) . . . . ?
O3 C13 C14 C15 -177.7(3) . . . . ?
C12 C13 C14 C15 2.9(4) . . . . ?
O3 C13 C14 C21 2.0(4) . . . . ?
C12 C13 C14 C21 -177.3(3) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C21 C14 C15 C16 -179.9(3) . . . . ?
C12 C11 C16 C15 3.8(4) . . . . ?
N2 C11 C16 C15 -173.0(3) . . . . ?
C12 C11 C16 C17 -173.9(3) . . . . ?
N2 C11 C16 C17 9.2(4) . . . . ?
C14 C15 C16 C11 -3.2(4) . . . . ?
C14 C15 C16 C17 174.7(3) . . . . ?
C11 C16 C17 C19 -68.3(4) . . . . ?
C15 C16 C17 C19 114.1(3) . . . . ?
C11 C16 C17 C18 55.3(4) . . . . ?
C15 C16 C17 C18 -122.3(3) . . . . ?
C11 C16 C17 C20 173.7(3) . . . . ?
C15 C16 C17 C20 -3.9(4) . . . . ?
C15 C14 C21 C24 -118.3(3) . . . . ?
C13 C14 C21 C24 62.0(4) . . . . ?
C15 C14 C21 C23 1.6(4) . . . . ?
C13 C14 C21 C23 -178.1(3) . . . . ?
C15 C14 C21 C22 120.7(3) . . . . ?
C13 C14 C21 C22 -59.0(4) . . . . ?
C8 C9 N1 C1 -1.9(4) . . . . ?
C6 C1 N1 C9 1.8(4) . . . . ?
C2 C1 N1 C9 -178.2(3) . . . . ?
O2 C10 N2 C11 -6.2(5) . . . . ?
C8 C10 N2 C11 170.4(3) . . . . ?
C12 C11 N2 C10 63.2(4) . . . . ?
C16 C11 N2 C10 -119.8(3) . . . . ?
O4 C25 C26 C27 85.7(4) . . . . ?
C25 C26 C27 C28 -0.7(5) . . . . ?
C25 C26 C27 C29 -178.1(3) . . . . ?
C26 C27 C29 C30 -119.1(3) . . . . ?
C28 C27 C29 C30 63.3(4) . . . . ?
C27 C29 C30 C31 177.4(3) . . . . ?
C29 C30 C31 C32 120.6(4) . . . . ?
C30 C31 C32 C33 2.4(5) . . . . ?
C30 C31 C32 C34 -177.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O4 0.97(4) 1.81(4) 2.780(4) 170(3) 2_666 yes
O1W H1W O4 0.889(19) 2.05(2) 2.931(4) 173(4) 1_655 yes
O1W H2W O1 0.871(19) 1.96(2) 2.817(3) 168(4) 1_565 yes
N2 H2N O1 0.89(3) 1.91(3) 2.695(3) 147(3) . yes
O3 H3O O1W 0.89(4) 1.87(4) 2.756(4) 174(4) . yes
O4 H4O O2 0.84(5) 1.83(5) 2.666(3) 176(5) . yes

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.073


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_mo_va329_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2494436'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor hydrochloride ethyl acetate solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H29 N2 O3, C4 H8 O2, Cl [+ solvent]'
_chemical_formula_sum            'C28 H37 Cl N2 O5'
_chemical_formula_weight         517.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2784(14)
_cell_length_b                   10.5283(17)
_cell_length_c                   15.382(3)
_cell_angle_alpha                76.476(6)
_cell_angle_beta                 85.972(5)
_cell_angle_gamma                89.973(5)
_cell_volume                     1614.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5062
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.03

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6032
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391

_diffrn_reflns_number            44076
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         28.781
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8154
_reflns_number_gt                4174
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.1688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8154
_refine_ls_number_parameters     406
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1943
_refine_ls_wR_factor_gt          0.1580
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.10277(19) 0.9093(2) 0.58712(14) 0.0515(5) Uani 1 1 d . . . . .
C2 C 0.0539(2) 0.9918(2) 0.64001(16) 0.0644(6) Uani 1 1 d . . . . .
H2 H 0.105203 1.059332 0.649533 0.077 Uiso 1 1 calc R U . . .
C3 C -0.0713(3) 0.9714(3) 0.67765(17) 0.0748(7) Uani 1 1 d . . . . .
H3 H -0.104723 1.024834 0.713909 0.090 Uiso 1 1 calc R U . . .
C4 C -0.1486(3) 0.8726(3) 0.66252(19) 0.0818(8) Uani 1 1 d . . . . .
H4 H -0.233746 0.861401 0.688070 0.098 Uiso 1 1 calc R U . . .
C5 C -0.1021(2) 0.7912(3) 0.61070(17) 0.0707(6) Uani 1 1 d . . . . .
H5 H -0.155131 0.724725 0.601436 0.085 Uiso 1 1 calc R U . . .
C6 C 0.02632(19) 0.8083(2) 0.57143(14) 0.0533(5) Uani 1 1 d . . . . .
C7 C 0.08061(19) 0.7278(2) 0.51532(15) 0.0541(5) Uani 1 1 d . . . . .
C8 C 0.20997(19) 0.75024(18) 0.47869(13) 0.0495(5) Uani 1 1 d . . . . .
C9 C 0.2784(2) 0.8530(2) 0.49675(14) 0.0529(5) Uani 1 1 d . . . . .
H9 H 0.363656 0.869968 0.472061 0.063 Uiso 1 1 calc R U . . .
C10 C 0.2618(2) 0.6659(2) 0.42062(15) 0.0551(5) Uani 1 1 d . . . . .
C11 C 0.4383(2) 0.60214(19) 0.32688(14) 0.0523(5) Uani 1 1 d . . . . .
C12 C 0.4451(2) 0.4696(2) 0.36291(14) 0.0567(5) Uani 1 1 d . . . . .
H12 H 0.412992 0.436063 0.421884 0.068 Uiso 1 1 calc R U . . .
C13 C 0.4979(2) 0.3858(2) 0.31428(15) 0.0590(5) Uani 1 1 d . . . . .
C14 C 0.5520(2) 0.4349(2) 0.22624(14) 0.0593(5) Uani 1 1 d . . . . .
C15 C 0.5411(2) 0.5675(2) 0.19333(15) 0.0605(5) Uani 1 1 d . . . . .
H15 H 0.575772 0.601369 0.135005 0.073 Uiso 1 1 calc R U . . .
C16 C 0.4833(2) 0.6567(2) 0.23835(14) 0.0571(5) Uani 1 1 d . . . . .
C17 C 0.6159(3) 0.3450(2) 0.17097(16) 0.0733(7) Uani 1 1 d . . . . .
C18 C 0.5124(4) 0.2540(3) 0.1516(2) 0.1059(10) Uani 1 1 d . . . . .
H18A H 0.446527 0.304720 0.118723 0.159 Uiso 1 1 calc R U . . .
H18B H 0.473466 0.202085 0.207094 0.159 Uiso 1 1 calc R U . . .
H18C H 0.552079 0.197700 0.116768 0.159 Uiso 1 1 calc R U . . .
C19 C 0.7251(4) 0.2681(3) 0.2207(2) 0.1087(11) Uani 1 1 d . . . . .
H19A H 0.770983 0.220125 0.182501 0.163 Uiso 1 1 calc R U . . .
H19B H 0.688490 0.208325 0.273797 0.163 Uiso 1 1 calc R U . . .
H19C H 0.784557 0.327395 0.237016 0.163 Uiso 1 1 calc R U . . .
C20 C 0.6778(4) 0.4247(3) 0.08018(19) 0.1043(11) Uani 1 1 d . . . . .
H20A H 0.715839 0.366244 0.046441 0.156 Uiso 1 1 calc R U . . .
H20B H 0.744287 0.482380 0.090568 0.156 Uiso 1 1 calc R U . . .
H20C H 0.611861 0.475061 0.047104 0.156 Uiso 1 1 calc R U . . .
C21 C 0.4782(3) 0.8015(2) 0.18806(16) 0.0697(6) Uani 1 1 d . . . . .
C22 C 0.3741(4) 0.8811(3) 0.2269(3) 0.1232(14) Uani 1 1 d . . . . .
H22A H 0.363282 0.962817 0.184858 0.185 Uiso 1 1 calc R U . . .
H22B H 0.400965 0.897138 0.281975 0.185 Uiso 1 1 calc R U . . .
H22C H 0.292859 0.833089 0.238319 0.185 Uiso 1 1 calc R U . . .
C23 C 0.6095(4) 0.8658(3) 0.1901(3) 0.1300(14) Uani 1 1 d . . . . .
H23A H 0.609262 0.954469 0.155667 0.195 Uiso 1 1 calc R U . . .
H23B H 0.676678 0.818832 0.164905 0.195 Uiso 1 1 calc R U . . .
H23C H 0.625880 0.864650 0.250934 0.195 Uiso 1 1 calc R U . . .
C24 C 0.4444(5) 0.8105(3) 0.0920(2) 0.1416(17) Uani 1 1 d . . . . .
H24A H 0.425311 0.899413 0.064166 0.212 Uiso 1 1 calc R U . . .
H24B H 0.369600 0.755917 0.092124 0.212 Uiso 1 1 calc R U . . .
H24C H 0.517056 0.781983 0.059086 0.212 Uiso 1 1 calc R U . . .
N1 N 0.22765(17) 0.92766(17) 0.54754(12) 0.0545(4) Uani 1 1 d D . . . .
H1N H 0.276(2) 0.996(2) 0.5544(15) 0.070(7) Uiso 1 1 d D . . . .
N2 N 0.38459(17) 0.68014(17) 0.38612(12) 0.0551(4) Uani 1 1 d D . . . .
H2N H 0.442(2) 0.730(2) 0.4041(16) 0.078(8) Uiso 1 1 d D . . . .
O1 O 0.00821(16) 0.63632(18) 0.49963(13) 0.0775(5) Uani 1 1 d D . . . .
H1O H 0.059(3) 0.609(3) 0.4596(19) 0.124(12) Uiso 1 1 d D . . . .
O2 O 0.18729(16) 0.58328(17) 0.40330(12) 0.0766(5) Uani 1 1 d . . . . .
O3 O 0.4978(2) 0.25373(15) 0.35016(13) 0.0800(5) Uani 1 1 d D . . . .
H2O H 0.462(3) 0.237(3) 0.4030(13) 0.092(9) Uiso 1 1 d D . . . .
Cl01 Cl 0.38669(6) 1.17030(6) 0.54750(4) 0.0688(2) Uani 1 1 d . . . . .
C25 C -0.1878(15) 0.5888(17) 0.3451(11) 0.099(3) Uani 0.625(16) 1 d D U P A 1
H25A H -0.204584 0.646330 0.384497 0.148 Uiso 0.625(16) 1 calc R U P A 1
H25B H -0.160219 0.505840 0.378813 0.148 Uiso 0.625(16) 1 calc R U P A 1
H25C H -0.266015 0.576907 0.317017 0.148 Uiso 0.625(16) 1 calc R U P A 1
C26 C -0.0842(15) 0.6463(15) 0.2755(13) 0.109(3) Uani 0.625(16) 1 d D U P A 1
C27 C 0.1091(12) 0.5770(15) 0.1980(8) 0.140(3) Uani 0.625(16) 1 d D U P A 1
H27A H 0.091707 0.642870 0.144671 0.168 Uiso 0.625(16) 1 calc R U P A 1
H27B H 0.169254 0.615588 0.230762 0.168 Uiso 0.625(16) 1 calc R U P A 1
C28 C 0.1671(13) 0.4799(12) 0.1729(9) 0.161(4) Uani 0.625(16) 1 d . U P A 1
H28A H 0.108229 0.438679 0.141826 0.242 Uiso 0.625(16) 1 calc R U P A 1
H28B H 0.193134 0.417580 0.224651 0.242 Uiso 0.625(16) 1 calc R U P A 1
H28C H 0.242761 0.512156 0.133696 0.242 Uiso 0.625(16) 1 calc R U P A 1
O4 O -0.0213(16) 0.7485(11) 0.2711(9) 0.141(3) Uani 0.625(16) 1 d D U P A 1
O5 O -0.0122(10) 0.5467(14) 0.2533(8) 0.105(2) Uani 0.625(16) 1 d D U P A 1
C25D C -0.191(3) 0.619(3) 0.328(2) 0.110(5) Uani 0.375(16) 1 d D U P A 2
H25D H -0.233862 0.702009 0.321105 0.164 Uiso 0.375(16) 1 calc R U P A 2
H25E H -0.187264 0.579815 0.390694 0.164 Uiso 0.375(16) 1 calc R U P A 2
H25F H -0.239415 0.563191 0.300570 0.164 Uiso 0.375(16) 1 calc R U P A 2
C26D C -0.056(2) 0.640(3) 0.284(2) 0.095(4) Uani 0.375(16) 1 d D U P A 2
C27D C 0.069(2) 0.574(3) 0.1632(17) 0.161(5) Uani 0.375(16) 1 d D U P A 2
H27C H 0.049567 0.641732 0.111594 0.193 Uiso 0.375(16) 1 calc R U P A 2
H27D H 0.144027 0.602225 0.189216 0.193 Uiso 0.375(16) 1 calc R U P A 2
C28D C 0.097(2) 0.463(2) 0.1377(14) 0.160(5) Uani 0.375(16) 1 d . U P A 2
H28D H 0.045336 0.457071 0.089050 0.240 Uiso 0.375(16) 1 calc R U P A 2
H28E H 0.077292 0.389750 0.187180 0.240 Uiso 0.375(16) 1 calc R U P A 2
H28F H 0.187753 0.463341 0.118388 0.240 Uiso 0.375(16) 1 calc R U P A 2
O4D O -0.011(4) 0.747(3) 0.241(2) 0.212(9) Uani 0.375(16) 1 d D U P A 2
O5D O -0.0430(19) 0.551(3) 0.2293(15) 0.123(4) Uani 0.375(16) 1 d D 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
C1 N1 1.375(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.369(3) . ?
C3 C4 1.381(4) . ?
C4 C5 1.366(4) . ?
C5 C6 1.406(3) . ?
C6 C7 1.431(3) . ?
C7 O1 1.294(2) . ?
C7 C8 1.405(3) . ?
C8 C9 1.383(3) . ?
C8 C10 1.474(3) . ?
C9 N1 1.315(3) . ?
C10 O2 1.246(2) . ?
C10 N2 1.329(3) . ?
C11 C12 1.379(3) . ?
C11 C16 1.394(3) . ?
C11 N2 1.445(3) . ?
C12 C13 1.372(3) . ?
C13 O3 1.371(3) . ?
C13 C14 1.406(3) . ?
C14 C15 1.377(3) . ?
C14 C17 1.532(3) . ?
C15 C16 1.401(3) . ?
C16 C21 1.542(3) . ?
C17 C18 1.523(4) . ?
C17 C19 1.527(4) . ?
C17 C20 1.545(4) . ?
C21 C23 1.516(4) . ?
C21 C24 1.523(4) . ?
C21 C22 1.532(4) . ?
C25 C26 1.477(13) . ?
C26 O4 1.241(13) . ?
C26 O5 1.377(13) . ?
C27 C28 1.305(15) . ?
C27 O5 1.451(11) . ?
C25D C26D 1.491(18) . ?
C26D O4D 1.238(18) . ?
C26D O5D 1.407(18) . ?
C27D C28D 1.34(3) . ?
C27D O5D 1.464(17) . ?

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
N1 C1 C2 120.20(19) . . ?
N1 C1 C6 118.44(18) . . ?
C2 C1 C6 121.34(19) . . ?
C3 C2 C1 118.6(2) . . ?
C2 C3 C4 120.9(2) . . ?
C5 C4 C3 121.1(2) . . ?
C4 C5 C6 119.7(2) . . ?
C1 C6 C5 118.3(2) . . ?
C1 C6 C7 119.06(18) . . ?
C5 C6 C7 122.6(2) . . ?
O1 C7 C8 121.9(2) . . ?
O1 C7 C6 118.62(18) . . ?
C8 C7 C6 119.46(18) . . ?
C9 C8 C7 117.82(18) . . ?
C9 C8 C10 124.37(18) . . ?
C7 C8 C10 117.77(17) . . ?
N1 C9 C8 122.50(18) . . ?
O2 C10 N2 121.00(19) . . ?
O2 C10 C8 118.52(18) . . ?
N2 C10 C8 120.47(18) . . ?
C12 C11 C16 121.14(19) . . ?
C12 C11 N2 116.42(18) . . ?
C16 C11 N2 122.43(18) . . ?
C13 C12 C11 121.9(2) . . ?
O3 C13 C12 120.8(2) . . ?
O3 C13 C14 119.11(19) . . ?
C12 C13 C14 120.09(19) . . ?
C15 C14 C13 115.46(19) . . ?
C15 C14 C17 122.9(2) . . ?
C13 C14 C17 121.6(2) . . ?
C14 C15 C16 126.9(2) . . ?
C11 C16 C15 114.31(19) . . ?
C11 C16 C21 127.08(19) . . ?
C15 C16 C21 118.59(19) . . ?
C18 C17 C19 111.2(3) . . ?
C18 C17 C14 109.2(2) . . ?
C19 C17 C14 110.4(2) . . ?
C18 C17 C20 107.8(2) . . ?
C19 C17 C20 107.1(3) . . ?
C14 C17 C20 111.1(2) . . ?
C23 C21 C24 110.9(3) . . ?
C23 C21 C22 107.6(3) . . ?
C24 C21 C22 105.2(3) . . ?
C23 C21 C16 108.8(2) . . ?
C24 C21 C16 109.6(2) . . ?
C22 C21 C16 114.7(2) . . ?
C9 N1 C1 122.70(17) . . ?
C10 N2 C11 122.28(17) . . ?
O4 C26 O5 114.8(13) . . ?
O4 C26 C25 126.1(17) . . ?
O5 C26 C25 108.6(14) . . ?
C28 C27 O5 116.7(12) . . ?
C26 O5 C27 119.6(13) . . ?
O4D C26D O5D 108(3) . . ?
O4D C26D C25D 125(3) . . ?
O5D C26D C25D 106(2) . . ?
C28D C27D O5D 109(2) . . ?
C26D O5D C27D 116(2) . . ?

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
N1 C1 C2 C3 179.4(2) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
N1 C1 C6 C5 -178.9(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C7 0.2(3) . . . . ?
C2 C1 C6 C7 178.9(2) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 -179.0(2) . . . . ?
C1 C6 C7 O1 -178.5(2) . . . . ?
C5 C6 C7 O1 0.5(3) . . . . ?
C1 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
O1 C7 C8 C9 177.9(2) . . . . ?
C6 C7 C8 C9 -1.9(3) . . . . ?
O1 C7 C8 C10 0.3(3) . . . . ?
C6 C7 C8 C10 -179.48(19) . . . . ?
C7 C8 C9 N1 1.1(3) . . . . ?
C10 C8 C9 N1 178.6(2) . . . . ?
C9 C8 C10 O2 -174.1(2) . . . . ?
C7 C8 C10 O2 3.3(3) . . . . ?
C9 C8 C10 N2 4.5(3) . . . . ?
C7 C8 C10 N2 -178.1(2) . . . . ?
C16 C11 C12 C13 1.0(3) . . . . ?
N2 C11 C12 C13 -177.9(2) . . . . ?
C11 C12 C13 O3 -176.8(2) . . . . ?
C11 C12 C13 C14 2.6(3) . . . . ?
O3 C13 C14 C15 176.1(2) . . . . ?
C12 C13 C14 C15 -3.2(3) . . . . ?
O3 C13 C14 C17 -2.7(3) . . . . ?
C12 C13 C14 C17 177.9(2) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C17 C14 C15 C16 179.3(2) . . . . ?
C12 C11 C16 C15 -3.6(3) . . . . ?
N2 C11 C16 C15 175.33(19) . . . . ?
C12 C11 C16 C21 177.9(2) . . . . ?
N2 C11 C16 C21 -3.2(3) . . . . ?
C14 C15 C16 C11 2.9(3) . . . . ?
C14 C15 C16 C21 -178.4(2) . . . . ?
C15 C14 C17 C18 -112.6(3) . . . . ?
C13 C14 C17 C18 66.2(3) . . . . ?
C15 C14 C17 C19 124.9(3) . . . . ?
C13 C14 C17 C19 -56.3(3) . . . . ?
C15 C14 C17 C20 6.2(4) . . . . ?
C13 C14 C17 C20 -175.0(2) . . . . ?
C11 C16 C21 C23 98.0(3) . . . . ?
C15 C16 C21 C23 -80.5(3) . . . . ?
C11 C16 C21 C24 -140.6(3) . . . . ?
C15 C16 C21 C24 40.9(3) . . . . ?
C11 C16 C21 C22 -22.6(4) . . . . ?
C15 C16 C21 C22 158.9(3) . . . . ?
C8 C9 N1 C1 0.3(3) . . . . ?
C2 C1 N1 C9 -179.7(2) . . . . ?
C6 C1 N1 C9 -1.0(3) . . . . ?
O2 C10 N2 C11 0.3(3) . . . . ?
C8 C10 N2 C11 -178.22(19) . . . . ?
C12 C11 N2 C10 -63.8(3) . . . . ?
C16 C11 N2 C10 117.2(2) . . . . ?
O4 C26 O5 C27 -22(2) . . . . ?
C25 C26 O5 C27 -169.4(13) . . . . ?
C28 C27 O5 C26 -174.3(13) . . . . ?
O4D C26D O5D C27D 30(3) . . . . ?
C25D C26D O5D C27D 166(2) . . . . ?
C28D C27D O5D C26D 159(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N Cl01 0.902(16) 2.140(17) 3.0333(18) 170(2) . yes
N2 H2N Cl01 0.890(16) 2.303(17) 3.1845(19) 170(2) 2_676 yes
O1 H1O O2 0.881(18) 1.58(2) 2.429(2) 160(3) . yes
O3 H2O Cl01 0.847(17) 2.250(18) 3.091(2) 172(3) 1_545 yes

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_mo_VA148_0m
_database_code_depnum_ccdc_archive 'CCDC 2494438'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor  acetic acid solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O3, C2 H4 O2'
_chemical_formula_sum            'C26 H32 N2 O5'
_chemical_formula_weight         452.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.2682(7)
_cell_length_b                   11.0691(3)
_cell_length_c                   18.7201(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.1082(9)
_cell_angle_gamma                90
_cell_volume                     4990.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.25

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6889
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            32965
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.193
_diffrn_reflns_theta_max         26.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5037
_reflns_number_gt                4082
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1041P)²+3.3420P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5037
_refine_ls_number_parameters     320
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1745
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.54919(8) 0.09448(18) 0.46494(11) 0.0525(4) Uani 1 1 d . . . . .
C2 C 0.54129(10) 0.0365(2) 0.39797(12) 0.0671(6) Uani 1 1 d . . . . .
H2 H 0.518501 0.070705 0.359673 0.081 Uiso 1 1 calc R U . . .
C3 C 0.56747(12) -0.0709(2) 0.38957(14) 0.0773(7) Uani 1 1 d . . . . .
H3 H 0.562243 -0.109753 0.345208 0.093 Uiso 1 1 calc R U . . .
C4 C 0.60170(12) -0.1229(2) 0.44603(15) 0.0781(7) Uani 1 1 d . . . . .
H4 H 0.619692 -0.195358 0.439180 0.094 Uiso 1 1 calc R U . . .
C5 C 0.60901(10) -0.0673(2) 0.51206(13) 0.0677(6) Uani 1 1 d . . . . .
H5 H 0.631591 -0.102895 0.550040 0.081 Uiso 1 1 calc R U . . .
C6 C 0.58270(8) 0.04285(17) 0.52265(11) 0.0528(5) Uani 1 1 d . . . . .
C7 C 0.58991(9) 0.10250(17) 0.59288(10) 0.0533(5) Uani 1 1 d . . . . .
C8 C 0.56391(7) 0.21931(16) 0.59617(9) 0.0470(4) Uani 1 1 d . . . . .
C9 C 0.53199(8) 0.26340(18) 0.53644(10) 0.0531(4) Uani 1 1 d . . . . .
H9 H 0.515169 0.338403 0.539444 0.064 Uiso 1 1 calc R U . . .
C10 C 0.57167(7) 0.29854(16) 0.66030(9) 0.0450(4) Uani 1 1 d . . . . .
C11 C 0.62113(8) 0.31658(16) 0.78274(9) 0.0457(4) Uani 1 1 d . . . . .
C12 C 0.58200(8) 0.37922(17) 0.81629(10) 0.0492(4) Uani 1 1 d . . . . .
H12 H 0.544835 0.375456 0.796993 0.059 Uiso 1 1 calc R U . . .
C13 C 0.59679(8) 0.44695(17) 0.87753(10) 0.0490(4) Uani 1 1 d . . . . .
C14 C 0.65209(8) 0.45338(17) 0.90792(9) 0.0489(4) Uani 1 1 d . . . . .
C15 C 0.68956(8) 0.38605(17) 0.87417(10) 0.0494(4) Uani 1 1 d . . . . .
H15 H 0.726506 0.388000 0.894526 0.059 Uiso 1 1 calc R U . . .
C16 C 0.67693(7) 0.31563(16) 0.81247(9) 0.0464(4) Uani 1 1 d . . . . .
C17 C 0.72244(8) 0.24120(19) 0.78243(12) 0.0585(5) Uani 1 1 d . . . . .
C18 C 0.72633(11) 0.2698(2) 0.70316(13) 0.0762(7) Uani 1 1 d . . . . .
H18A H 0.758174 0.229973 0.688346 0.114 Uiso 1 1 calc R U . . .
H18B H 0.729874 0.355479 0.697233 0.114 Uiso 1 1 calc R U . . .
H18C H 0.693370 0.241861 0.674222 0.114 Uiso 1 1 calc R U . . .
C19 C 0.71096(12) 0.1055(2) 0.79204(15) 0.0785(7) Uani 1 1 d . . . . .
H19A H 0.675401 0.085217 0.766464 0.118 Uiso 1 1 calc R U . . .
H19B H 0.711013 0.087854 0.842260 0.118 Uiso 1 1 calc R U . . .
H19C H 0.739305 0.058815 0.773359 0.118 Uiso 1 1 calc R U . . .
C20 C 0.77985(10) 0.2666(3) 0.82423(17) 0.0859(8) Uani 1 1 d . . . . .
H20A H 0.807265 0.217862 0.805047 0.129 Uiso 1 1 calc R U . . .
H20B H 0.779276 0.247291 0.874134 0.129 Uiso 1 1 calc R U . . .
H20C H 0.788868 0.350438 0.819631 0.129 Uiso 1 1 calc R U . . .
C21 C 0.67132(9) 0.5312(2) 0.97468(11) 0.0636(5) Uani 1 1 d . . . . .
C22 C 0.65828(13) 0.6639(2) 0.95759(16) 0.0836(7) Uani 1 1 d . . . . .
H22A H 0.676754 0.688708 0.917533 0.125 Uiso 1 1 calc R U . . .
H22B H 0.670980 0.712587 0.998816 0.125 Uiso 1 1 calc R U . . .
H22C H 0.618919 0.673920 0.945687 0.125 Uiso 1 1 calc R U . . .
C23 C 0.64184(12) 0.4892(3) 1.03845(12) 0.0817(7) Uani 1 1 d . . . . .
H23A H 0.602490 0.500007 1.026928 0.123 Uiso 1 1 calc R U . . .
H23B H 0.654836 0.536014 1.080327 0.123 Uiso 1 1 calc R U . . .
H23C H 0.649776 0.405336 1.047895 0.123 Uiso 1 1 calc R U . . .
C24 C 0.73418(11) 0.5209(3) 0.99722(16) 0.0938(9) Uani 1 1 d . . . . .
H24A H 0.753567 0.544375 0.957717 0.141 Uiso 1 1 calc R U . . .
H24B H 0.743422 0.438961 1.010471 0.141 Uiso 1 1 calc R U . . .
H24C H 0.744831 0.573075 1.037547 0.141 Uiso 1 1 calc R U . . .
N1 N 0.52394(8) 0.20386(16) 0.47427(9) 0.0580(4) Uani 1 1 d . . . . .
H1N H 0.5011(11) 0.237(2) 0.4361(15) 0.080(8) Uiso 1 1 d . . . . .
N2 N 0.60238(7) 0.25202(15) 0.71839(8) 0.0514(4) Uani 1 1 d . . . . .
H2N H 0.6155(11) 0.176(3) 0.7111(14) 0.077(7) Uiso 1 1 d . . . . .
O1 O 0.61755(8) 0.05261(13) 0.64537(9) 0.0785(5) Uani 1 1 d . . . . .
O2 O 0.55186(6) 0.40242(12) 0.65839(7) 0.0539(4) Uani 1 1 d . . . . .
O3 O 0.55657(6) 0.50810(16) 0.90844(8) 0.0654(4) Uani 1 1 d D . . . .
H3O H 0.5262(10) 0.505(3) 0.8791(16) 0.110(11) Uiso 1 1 d D . . . .
C25 C 0.58565(15) 0.8136(3) 0.7400(2) 0.1056(10) Uani 1 1 d . . . . .
H25A H 0.609870 0.858601 0.713078 0.158 Uiso 1 1 calc R U . . .
H25B H 0.604731 0.794785 0.786720 0.158 Uiso 1 1 calc R U . . .
H25C H 0.553250 0.860876 0.745298 0.158 Uiso 1 1 calc R U . . .
C26 C 0.56869(11) 0.6989(2) 0.70102(14) 0.0752(6) Uani 1 1 d . . . . .
O4 O 0.59636(9) 0.60369(17) 0.72414(11) 0.0909(6) Uani 1 1 d D . . . .
H4O H 0.5773(15) 0.545(3) 0.6964(19) 0.136 Uiso 1 1 d D U . . .
O5 O 0.53292(13) 0.6936(2) 0.65167(14) 0.1400(11) Uani 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
C1 N1 1.378(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.400(3) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(3) . ?
C7 O1 1.248(2) . ?
C7 C8 1.443(3) . ?
C8 C9 1.369(3) . ?
C8 C10 1.480(2) . ?
C9 N1 1.331(3) . ?
C9 H9 0.9300 . ?
C10 O2 1.245(2) . ?
C10 N2 1.343(2) . ?
C11 C12 1.387(3) . ?
C11 C16 1.399(3) . ?
C11 N2 1.426(2) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 O3 1.373(2) . ?
C13 C14 1.393(3) . ?
C14 C15 1.387(3) . ?
C14 C21 1.542(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.539(3) . ?
C17 C18 1.532(3) . ?
C17 C20 1.537(3) . ?
C17 C19 1.543(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.529(4) . ?
C21 C24 1.536(3) . ?
C21 C23 1.538(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1N 0.93(3) . ?
N2 H2N 0.92(3) . ?
O3 H3O 0.863(18) . ?
C25 C26 1.496(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O5 1.188(3) . ?
C26 O4 1.295(3) . ?
O4 H4O 0.919(19) . ?

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
N1 C1 C6 119.25(17) . . ?
N1 C1 C2 120.16(19) . . ?
C6 C1 C2 120.6(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.68(19) . . ?
C1 C6 C7 120.39(18) . . ?
C5 C6 C7 120.93(19) . . ?
O1 C7 C8 123.92(18) . . ?
O1 C7 C6 120.06(18) . . ?
C8 C7 C6 116.02(17) . . ?
C9 C8 C7 119.37(17) . . ?
C9 C8 C10 116.98(17) . . ?
C7 C8 C10 123.59(16) . . ?
N1 C9 C8 123.02(19) . . ?
N1 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
O2 C10 N2 123.44(16) . . ?
O2 C10 C8 120.94(16) . . ?
N2 C10 C8 115.59(16) . . ?
C12 C11 C16 120.45(16) . . ?
C12 C11 N2 117.90(16) . . ?
C16 C11 N2 121.63(16) . . ?
C13 C12 C11 121.70(17) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
O3 C13 C12 119.51(17) . . ?
O3 C13 C14 120.12(17) . . ?
C12 C13 C14 120.36(17) . . ?
C15 C14 C13 116.06(17) . . ?
C15 C14 C21 121.32(17) . . ?
C13 C14 C21 122.62(17) . . ?
C14 C15 C16 126.00(17) . . ?
C14 C15 H15 117.0 . . ?
C16 C15 H15 117.0 . . ?
C15 C16 C11 115.33(16) . . ?
C15 C16 C17 120.48(16) . . ?
C11 C16 C17 124.18(16) . . ?
C18 C17 C20 107.2(2) . . ?
C18 C17 C16 112.11(18) . . ?
C20 C17 C16 111.25(17) . . ?
C18 C17 C19 110.4(2) . . ?
C20 C17 C19 106.5(2) . . ?
C16 C17 C19 109.31(18) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C24 107.5(2) . . ?
C22 C21 C23 110.4(2) . . ?
C24 C21 C23 107.8(2) . . ?
C22 C21 C14 109.47(19) . . ?
C24 C21 C14 111.84(18) . . ?
C23 C21 C14 109.70(19) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C1 121.78(18) . . ?
C9 N1 H1N 119.1(17) . . ?
C1 N1 H1N 119.1(17) . . ?
C10 N2 C11 125.40(16) . . ?
C10 N2 H2N 113.5(16) . . ?
C11 N2 H2N 120.4(16) . . ?
C13 O3 H3O 108(2) . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C26 O4 121.2(3) . . ?
O5 C26 C25 123.5(3) . . ?
O4 C26 C25 115.3(2) . . ?
C26 O4 H4O 100(3) . . ?

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
N1 C1 C2 C3 178.9(2) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
N1 C1 C6 C5 -178.76(19) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
N1 C1 C6 C7 1.5(3) . . . . ?
C2 C1 C6 C7 -178.74(19) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C1 C6 C7 O1 176.1(2) . . . . ?
C5 C6 C7 O1 -3.6(3) . . . . ?
C1 C6 C7 C8 -4.4(3) . . . . ?
C5 C6 C7 C8 175.93(19) . . . . ?
O1 C7 C8 C9 -176.6(2) . . . . ?
C6 C7 C8 C9 3.9(3) . . . . ?
O1 C7 C8 C10 6.3(3) . . . . ?
C6 C7 C8 C10 -173.23(16) . . . . ?
C7 C8 C9 N1 -0.7(3) . . . . ?
C10 C8 C9 N1 176.69(17) . . . . ?
C9 C8 C10 O2 -3.0(3) . . . . ?
C7 C8 C10 O2 174.24(17) . . . . ?
C9 C8 C10 N2 178.91(17) . . . . ?
C7 C8 C10 N2 -3.9(3) . . . . ?
C16 C11 C12 C13 3.2(3) . . . . ?
N2 C11 C12 C13 -178.03(16) . . . . ?
C11 C12 C13 O3 179.50(17) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
O3 C13 C14 C15 178.29(17) . . . . ?
C12 C13 C14 C15 -1.7(3) . . . . ?
O3 C13 C14 C21 -2.3(3) . . . . ?
C12 C13 C14 C21 177.76(18) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C21 C14 C15 C16 -178.01(18) . . . . ?
C14 C15 C16 C11 1.0(3) . . . . ?
C14 C15 C16 C17 -177.51(18) . . . . ?
C12 C11 C16 C15 -3.3(3) . . . . ?
N2 C11 C16 C15 177.97(16) . . . . ?
C12 C11 C16 C17 175.18(17) . . . . ?
N2 C11 C16 C17 -3.6(3) . . . . ?
C15 C16 C17 C18 -125.3(2) . . . . ?
C11 C16 C17 C18 56.3(3) . . . . ?
C15 C16 C17 C20 -5.4(3) . . . . ?
C11 C16 C17 C20 176.2(2) . . . . ?
C15 C16 C17 C19 112.0(2) . . . . ?
C11 C16 C17 C19 -66.4(2) . . . . ?
C15 C14 C21 C22 118.0(2) . . . . ?
C13 C14 C21 C22 -61.4(3) . . . . ?
C15 C14 C21 C24 -1.1(3) . . . . ?
C13 C14 C21 C24 179.5(2) . . . . ?
C15 C14 C21 C23 -120.7(2) . . . . ?
C13 C14 C21 C23 59.9(3) . . . . ?
C8 C9 N1 C1 -2.5(3) . . . . ?
C6 C1 N1 C9 2.0(3) . . . . ?
C2 C1 N1 C9 -177.7(2) . . . . ?
O2 C10 N2 C11 -6.4(3) . . . . ?
C8 C10 N2 C11 171.67(16) . . . . ?
C12 C11 N2 C10 52.5(3) . . . . ?
C16 C11 N2 C10 -128.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3O O2 0.863(18) 2.25(2) 3.007(2) 147(3) 2_656 yes
O3 H3O O5 0.863(18) 2.56(3) 3.097(3) 121(3) 2_656 yes
N1 H1N O5 0.93(3) 1.91(3) 2.819(3) 169(2) 5_666 yes
N2 H2N O1 0.92(3) 1.84(3) 2.646(2) 145(2) . yes
O4 H4O O2 0.919(19) 1.81(2) 2.705(2) 164(4) . yes

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetic acid'
####################################################################### 
# 
# 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_KB1803_0m
_database_code_depnum_ccdc_archive 'CCDC 2494440'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor ethanolamine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O3, C2 H7 N O'
_chemical_formula_sum            'C26 H35 N3 O4'
_chemical_formula_weight         453.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9230(3)
_cell_length_b                   9.5568(4)
_cell_length_c                   20.6857(8)
_cell_angle_alpha                78.3703(12)
_cell_angle_beta                 89.8695(13)
_cell_angle_gamma                71.8961(12)
_cell_volume                     1271.46(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            28701
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.302
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6320
_reflns_number_gt                4918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+0.2033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6320
_refine_ls_number_parameters     328
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1602
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.25014(17) 0.51715(14) 0.45892(6) 0.0362(3) Uani 1 1 d . . . . .
C2 C 1.2957(2) 0.46878(16) 0.39922(6) 0.0434(3) Uani 1 1 d . . . . .
H2 H 1.273338 0.538681 0.359335 0.052 Uiso 1 1 calc R U . . .
C3 C 1.3731(2) 0.31845(17) 0.40029(7) 0.0509(3) Uani 1 1 d . . . . .
H3 H 1.402754 0.285966 0.360875 0.061 Uiso 1 1 calc R U . . .
C4 C 1.4082(3) 0.21326(17) 0.45979(8) 0.0595(4) Uani 1 1 d . . . . .
H4 H 1.461776 0.111093 0.459909 0.071 Uiso 1 1 calc R U . . .
C5 C 1.3640(3) 0.25952(16) 0.51845(7) 0.0525(3) Uani 1 1 d . . . . .
H5 H 1.387670 0.188373 0.557974 0.063 Uiso 1 1 calc R U . . .
C6 C 1.28336(18) 0.41321(14) 0.51908(6) 0.0375(3) Uani 1 1 d . . . . .
C7 C 1.2340(2) 0.46394(14) 0.58149(6) 0.0389(3) Uani 1 1 d . . . . .
C8 C 1.15719(19) 0.62466(14) 0.57537(6) 0.0382(3) Uani 1 1 d . . . . .
C9 C 1.1307(2) 0.71764(14) 0.51416(6) 0.0420(3) Uani 1 1 d . . . . .
H9 H 1.080524 0.821052 0.511464 0.050 Uiso 1 1 calc R U . . .
C10 C 1.1019(2) 0.70040(14) 0.63224(6) 0.0440(3) Uani 1 1 d . . . . .
C11 C 1.0575(2) 0.65721(13) 0.75227(6) 0.0390(3) Uani 1 1 d . . . . .
C12 C 0.8725(2) 0.76969(15) 0.75119(6) 0.0441(3) Uani 1 1 d . . . . .
H12 H 0.792173 0.809853 0.711764 0.053 Uiso 1 1 calc R U . . .
C13 C 0.8044(2) 0.82371(15) 0.80733(7) 0.0455(3) Uani 1 1 d . . . . .
C14 C 0.9219(2) 0.76324(15) 0.86736(6) 0.0449(3) Uani 1 1 d . . . . .
C15 C 1.1047(2) 0.65031(14) 0.86653(6) 0.0439(3) Uani 1 1 d . . . . .
H15 H 1.183460 0.609019 0.906228 0.053 Uiso 1 1 calc R U . . .
C16 C 1.1811(2) 0.59303(13) 0.81108(6) 0.0402(3) Uani 1 1 d . . . . .
C17 C 0.8530(3) 0.82071(17) 0.93075(7) 0.0578(4) Uani 1 1 d . . . . .
C18 C 1.0054(4) 0.7346(2) 0.99027(8) 0.0796(6) Uani 1 1 d . . . . .
H18A H 1.017613 0.629647 0.998272 0.119 Uiso 1 1 calc R U . . .
H18B H 0.957810 0.773755 1.028683 0.119 Uiso 1 1 calc R U . . .
H18C H 1.135884 0.746761 0.981024 0.119 Uiso 1 1 calc R U . . .
C19 C 0.8402(4) 0.9866(2) 0.92016(9) 0.0799(6) Uani 1 1 d . . . . .
H19A H 0.970235 0.996948 0.908652 0.120 Uiso 1 1 calc R U . . .
H19B H 0.802888 1.021916 0.960119 0.120 Uiso 1 1 calc R U . . .
H19C H 0.739538 1.044909 0.885050 0.120 Uiso 1 1 calc R U . . .
C20 C 0.6465(4) 0.8012(3) 0.94789(11) 0.0967(7) Uani 1 1 d . . . . .
H20A H 0.548207 0.854571 0.911493 0.145 Uiso 1 1 calc R U . . .
H20B H 0.602781 0.840524 0.986536 0.145 Uiso 1 1 calc R U . . .
H20C H 0.658822 0.696109 0.956382 0.145 Uiso 1 1 calc R U . . .
C21 C 1.3863(2) 0.46663(16) 0.81732(7) 0.0512(3) Uani 1 1 d . . . . .
C22 C 1.4976(3) 0.4316(2) 0.88562(8) 0.0762(6) Uani 1 1 d . . . . .
H22A H 1.626638 0.354914 0.886747 0.114 Uiso 1 1 calc R U . . .
H22B H 1.416743 0.396772 0.918968 0.114 Uiso 1 1 calc R U . . .
H22C H 1.519125 0.521127 0.893850 0.114 Uiso 1 1 calc R U . . .
C23 C 1.3468(4) 0.32137(18) 0.80881(10) 0.0833(6) Uani 1 1 d . . . . .
H23A H 1.279243 0.338016 0.766160 0.125 Uiso 1 1 calc R U . . .
H23B H 1.262425 0.293616 0.842671 0.125 Uiso 1 1 calc R U . . .
H23C H 1.474114 0.241831 0.812306 0.125 Uiso 1 1 calc R U . . .
C24 C 1.5293(3) 0.5097(3) 0.76665(10) 0.0851(6) Uani 1 1 d . . . . .
H24A H 1.473529 0.519370 0.722910 0.128 Uiso 1 1 calc R U . . .
H24B H 1.659823 0.432927 0.774077 0.128 Uiso 1 1 calc R U . . .
H24C H 1.544572 0.603850 0.771031 0.128 Uiso 1 1 calc R U . . .
N1 N 1.17250(17) 0.66868(12) 0.45818(5) 0.0409(2) Uani 1 1 d . . . . .
H1N H 1.155(3) 0.734(2) 0.4228(9) 0.056(5) Uiso 1 1 d . . . . .
N2 N 1.11180(19) 0.60917(13) 0.69154(5) 0.0433(3) Uani 1 1 d . . . . .
H2N H 1.148(3) 0.519(2) 0.6913(9) 0.060(5) Uiso 1 1 d . . . . .
O1 O 1.25931(19) 0.37068(11) 0.63502(5) 0.0566(3) Uani 1 1 d . . . . .
O2 O 1.0535(2) 0.83876(11) 0.62330(5) 0.0705(4) Uani 1 1 d . . . . .
O3 O 0.62546(18) 0.93666(15) 0.80423(6) 0.0672(3) Uani 1 1 d . . . . .
H3O H 0.564(3) 0.950(2) 0.7693(10) 0.082(7) Uiso 1 1 d D . . . .
C25 C -0.0316(3) 1.13166(18) 0.71787(8) 0.0591(4) Uani 1 1 d . . . . .
H25A H -0.131221 1.119788 0.749776 0.071 Uiso 1 1 calc R U . . .
H25B H -0.027365 1.233857 0.712499 0.071 Uiso 1 1 calc R U . . .
C26 C 0.1731(2) 1.02536(17) 0.74596(8) 0.0558(4) Uani 1 1 d . . . . .
H26A H 0.205599 1.049583 0.787088 0.067 Uiso 1 1 calc R U . . .
H26B H 0.165058 0.923780 0.756261 0.067 Uiso 1 1 calc R U . . .
N3 N 0.3403(2) 1.02860(18) 0.70189(8) 0.0653(4) Uani 1 1 d D . . . .
H3N H 0.266(3) 1.017(2) 0.6670(9) 0.075(6) Uiso 1 1 d D . . . .
H4N H 0.388(2) 1.0975(17) 0.6823(8) 0.056(5) Uiso 1 1 d D . . . .
O4 O -0.0990(2) 1.11361(13) 0.65693(6) 0.0628(3) Uani 1 1 d . . . . .
H4O H -0.067(4) 1.022(3) 0.6517(14) 0.115(9) 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
C1 N1 1.3761(16) . ?
C1 C6 1.3962(17) . ?
C1 C2 1.4057(16) . ?
C2 C3 1.364(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3754(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.4026(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4717(16) . ?
C7 O1 1.2478(15) . ?
C7 C8 1.4395(17) . ?
C8 C9 1.3685(17) . ?
C8 C10 1.4910(16) . ?
C9 N1 1.3329(16) . ?
C9 H9 0.9300 . ?
C10 O2 1.2334(16) . ?
C10 N2 1.3423(17) . ?
C11 C12 1.3894(18) . ?
C11 C16 1.4024(18) . ?
C11 N2 1.4330(15) . ?
C12 C13 1.3876(18) . ?
C12 H12 0.9300 . ?
C13 O3 1.3587(17) . ?
C13 C14 1.4001(19) . ?
C14 C15 1.3877(19) . ?
C14 C17 1.5406(17) . ?
C15 C16 1.4019(16) . ?
C15 H15 0.9300 . ?
C16 C21 1.5378(18) . ?
C17 C19 1.530(2) . ?
C17 C20 1.530(3) . ?
C17 C18 1.538(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C24 1.524(3) . ?
C21 C22 1.535(2) . ?
C21 C23 1.539(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1N 0.841(19) . ?
N2 H2N 0.822(19) . ?
O3 H3O 0.805(19) . ?
C25 O4 1.4061(19) . ?
C25 C26 1.499(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 N3 1.476(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
N3 H3N 0.931(15) . ?
N3 H4N 0.857(14) . ?
O4 H4O 0.87(3) . ?

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
N1 C1 C6 119.53(10) . . ?
N1 C1 C2 119.70(11) . . ?
C6 C1 C2 120.76(11) . . ?
C3 C2 C1 119.43(12) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.62(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.37(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.48(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.34(11) . . ?
C1 C6 C7 120.71(11) . . ?
C5 C6 C7 120.95(11) . . ?
O1 C7 C8 124.11(11) . . ?
O1 C7 C6 120.58(11) . . ?
C8 C7 C6 115.31(10) . . ?
C9 C8 C7 119.67(11) . . ?
C9 C8 C10 116.06(11) . . ?
C7 C8 C10 124.27(11) . . ?
N1 C9 C8 123.83(12) . . ?
N1 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
O2 C10 N2 123.97(12) . . ?
O2 C10 C8 120.06(11) . . ?
N2 C10 C8 115.96(11) . . ?
C12 C11 C16 120.53(11) . . ?
C12 C11 N2 117.04(11) . . ?
C16 C11 N2 122.42(11) . . ?
C13 C12 C11 121.78(12) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
O3 C13 C12 120.36(12) . . ?
O3 C13 C14 119.67(12) . . ?
C12 C13 C14 119.97(12) . . ?
C15 C14 C13 116.50(11) . . ?
C15 C14 C17 121.80(12) . . ?
C13 C14 C17 121.70(13) . . ?
C14 C15 C16 125.71(12) . . ?
C14 C15 H15 117.1 . . ?
C16 C15 H15 117.1 . . ?
C15 C16 C11 115.50(12) . . ?
C15 C16 C21 120.25(11) . . ?
C11 C16 C21 124.24(11) . . ?
C19 C17 C20 110.62(17) . . ?
C19 C17 C18 107.20(15) . . ?
C20 C17 C18 107.88(17) . . ?
C19 C17 C14 109.06(13) . . ?
C20 C17 C14 110.17(14) . . ?
C18 C17 C14 111.86(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 C21 C22 106.66(16) . . ?
C24 C21 C16 111.18(12) . . ?
C22 C21 C16 112.32(11) . . ?
C24 C21 C23 111.00(16) . . ?
C22 C21 C23 106.81(14) . . ?
C16 C21 C23 108.79(14) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C1 120.92(11) . . ?
C9 N1 H1N 117.4(12) . . ?
C1 N1 H1N 121.6(12) . . ?
C10 N2 C11 125.56(11) . . ?
C10 N2 H2N 115.0(12) . . ?
C11 N2 H2N 119.4(12) . . ?
C13 O3 H3O 109.3(15) . . ?
O4 C25 C26 115.69(13) . . ?
O4 C25 H25A 108.4 . . ?
C26 C25 H25A 108.4 . . ?
O4 C25 H25B 108.4 . . ?
C26 C25 H25B 108.4 . . ?
H25A C25 H25B 107.4 . . ?
N3 C26 C25 114.45(13) . . ?
N3 C26 H26A 108.6 . . ?
C25 C26 H26A 108.6 . . ?
N3 C26 H26B 108.6 . . ?
C25 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C26 N3 H3N 91.2(13) . . ?
C26 N3 H4N 134.6(12) . . ?
H3N N3 H4N 101.1(17) . . ?
C25 O4 H4O 115.7(19) . . ?

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
N1 C1 C2 C3 179.84(12) . . . . ?
C6 C1 C2 C3 0.06(19) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
N1 C1 C6 C5 -179.56(12) . . . . ?
C2 C1 C6 C5 0.22(19) . . . . ?
N1 C1 C6 C7 0.73(18) . . . . ?
C2 C1 C6 C7 -179.49(11) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C6 C7 179.51(14) . . . . ?
C1 C6 C7 O1 178.31(12) . . . . ?
C5 C6 C7 O1 -1.4(2) . . . . ?
C1 C6 C7 C8 -1.81(17) . . . . ?
C5 C6 C7 C8 178.48(13) . . . . ?
O1 C7 C8 C9 -178.59(13) . . . . ?
C6 C7 C8 C9 1.54(18) . . . . ?
O1 C7 C8 C10 1.2(2) . . . . ?
C6 C7 C8 C10 -178.63(12) . . . . ?
C7 C8 C9 N1 -0.2(2) . . . . ?
C10 C8 C9 N1 179.98(12) . . . . ?
C9 C8 C10 O2 -6.3(2) . . . . ?
C7 C8 C10 O2 173.88(14) . . . . ?
C9 C8 C10 N2 174.64(13) . . . . ?
C7 C8 C10 N2 -5.2(2) . . . . ?
C16 C11 C12 C13 0.8(2) . . . . ?
N2 C11 C12 C13 179.50(12) . . . . ?
C11 C12 C13 O3 178.19(13) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
O3 C13 C14 C15 -178.75(13) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
O3 C13 C14 C17 0.4(2) . . . . ?
C12 C13 C14 C17 179.50(14) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C17 C14 C15 C16 -178.81(14) . . . . ?
C14 C15 C16 C11 -0.5(2) . . . . ?
C14 C15 C16 C21 -179.65(13) . . . . ?
C12 C11 C16 C15 -0.08(19) . . . . ?
N2 C11 C16 C15 -178.76(12) . . . . ?
C12 C11 C16 C21 179.05(13) . . . . ?
N2 C11 C16 C21 0.4(2) . . . . ?
C15 C14 C17 C19 116.41(17) . . . . ?
C13 C14 C17 C19 -62.7(2) . . . . ?
C15 C14 C17 C20 -122.00(18) . . . . ?
C13 C14 C17 C20 58.9(2) . . . . ?
C15 C14 C17 C18 -2.0(2) . . . . ?
C13 C14 C17 C18 178.87(16) . . . . ?
C15 C16 C21 C24 -126.66(16) . . . . ?
C11 C16 C21 C24 54.2(2) . . . . ?
C15 C16 C21 C22 -7.2(2) . . . . ?
C11 C16 C21 C22 173.68(15) . . . . ?
C15 C16 C21 C23 110.80(15) . . . . ?
C11 C16 C21 C23 -68.29(18) . . . . ?
C8 C9 N1 C1 -1.1(2) . . . . ?
C6 C1 N1 C9 0.74(18) . . . . ?
C2 C1 N1 C9 -179.04(12) . . . . ?
O2 C10 N2 C11 3.8(2) . . . . ?
C8 C10 N2 C11 -177.19(12) . . . . ?
C12 C11 N2 C10 47.71(19) . . . . ?
C16 C11 N2 C10 -133.57(15) . . . . ?
O4 C25 C26 N3 56.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O4 0.841(19) 1.918(19) 2.7582(16) 176.6(17) 2_676 yes
N2 H2N O1 0.822(19) 1.984(18) 2.6883(14) 143.3(17) . yes
O3 H3O N3 0.805(19) 1.944(19) 2.710(2) 159(2) . yes
N3 H3N O4 0.931(15) 2.398(19) 2.991(2) 121.5(15) . yes
N3 H4N O1 0.857(14) 2.469(15) 3.1555(19) 137.6(14) 1_465 yes
O4 H4O O2 0.87(3) 1.90(3) 2.7400(16) 164(3) 1_455 yes

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
####################################################################### 
# 
# 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_KB1498_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2494434'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor dihydrate'
_chemical_name_common            'ivacaftor dihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O3, 2(H2 O)'
_chemical_formula_sum            'C24 H32 N2 O5'
_chemical_formula_weight         428.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.721(2)
_cell_length_b                   8.395(2)
_cell_length_c                   21.299(7)
_cell_angle_alpha                80.462(12)
_cell_angle_beta                 89.652(13)
_cell_angle_gamma                80.149(12)
_cell_volume                     1167.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2320
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.29

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5009
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13945
_diffrn_reflns_av_unetI/netI     0.1661
_diffrn_reflns_av_R_equivalents  0.1092
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4046
_reflns_number_gt                2085
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.6870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4046
_refine_ls_number_parameters     309
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1710
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.1636
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2277(5) 1.2558(4) 0.52581(18) 0.0238(9) Uani 1 1 d . . . . .
H1 H 0.247004 1.302069 0.562638 0.029 Uiso 1 1 calc R U . . .
C2 C 0.1699(5) 1.3572(5) 0.46899(19) 0.0284(10) Uani 1 1 d . . . . .
H2 H 0.151105 1.472806 0.466602 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1390(5) 1.2903(5) 0.41493(19) 0.0281(10) Uani 1 1 d . . . . .
H3 H 0.095939 1.361250 0.376108 0.034 Uiso 1 1 calc R U . . .
C4 C 0.1693(5) 1.1253(5) 0.41681(19) 0.0265(10) Uani 1 1 d . . . . .
H4 H 0.149431 1.080832 0.379577 0.032 Uiso 1 1 calc R U . . .
C5 C 0.2306(5) 1.0212(4) 0.47475(18) 0.0223(9) Uani 1 1 d . . . . .
C6 C 0.2585(5) 1.0851(4) 0.53001(18) 0.0222(9) Uani 1 1 d . . . . .
C7 C 0.3193(5) 0.9739(4) 0.59061(19) 0.0220(9) Uani 1 1 d . . . . .
C8 C 0.3483(5) 0.8026(4) 0.58753(18) 0.0214(9) Uani 1 1 d . . . . .
C9 C 0.3181(5) 0.7521(5) 0.53092(19) 0.0255(10) Uani 1 1 d . . . . .
H9 H 0.338724 0.637591 0.530189 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4081(5) 0.6683(5) 0.64271(19) 0.0235(9) Uani 1 1 d . . . . .
C11 C 0.5069(6) 0.6031(4) 0.75470(18) 0.0251(9) Uani 1 1 d . . . . .
C12 C 0.6869(6) 0.4914(4) 0.75543(18) 0.0262(10) Uani 1 1 d . . . . .
H12 H 0.766570 0.494899 0.718390 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7516(6) 0.3770(4) 0.80797(19) 0.0283(10) Uani 1 1 d . . . . .
C14 C 0.6360(6) 0.3666(5) 0.86300(18) 0.0294(10) Uani 1 1 d . . . . .
C15 C 0.4583(6) 0.4819(4) 0.86081(19) 0.0282(10) Uani 1 1 d . . . . .
H15 H 0.380012 0.478558 0.898141 0.034 Uiso 1 1 calc R U . . .
C16 C 0.3858(6) 0.6012(5) 0.80873(18) 0.0269(10) Uani 1 1 d . . . . .
C17 C 0.1932(6) 0.7280(4) 0.81296(19) 0.0290(10) Uani 1 1 d . . . . .
C18 C 0.0526(6) 0.7537(5) 0.75443(19) 0.0427(12) Uani 1 1 d . . . . .
H18A H 0.109271 0.818781 0.718435 0.064 Uiso 1 1 calc R U . . .
H18B H -0.080610 0.811618 0.763879 0.064 Uiso 1 1 calc R U . . .
H18C H 0.039341 0.646960 0.743552 0.064 Uiso 1 1 calc R U . . .
C19 C 0.2551(6) 0.8909(5) 0.8204(2) 0.0422(12) Uani 1 1 d . . . . .
H19A H 0.333584 0.928193 0.783572 0.063 Uiso 1 1 calc R U . . .
H19B H 0.337413 0.876075 0.859373 0.063 Uiso 1 1 calc R U . . .
H19C H 0.133835 0.972928 0.822847 0.063 Uiso 1 1 calc R U . . .
C20 C 0.0697(6) 0.6723(5) 0.8708(2) 0.0420(11) Uani 1 1 d . . . . .
H20A H -0.053355 0.753285 0.872043 0.063 Uiso 1 1 calc R U . . .
H20B H 0.150480 0.662279 0.909875 0.063 Uiso 1 1 calc R U . . .
H20C H 0.033275 0.565864 0.867458 0.063 Uiso 1 1 calc R U . . .
C21 C 0.6985(6) 0.2362(5) 0.92187(19) 0.0328(10) Uani 1 1 d . . . . .
C22 C 0.7050(6) 0.0661(5) 0.90349(19) 0.0407(11) Uani 1 1 d . . . . .
H22A H 0.571020 0.057095 0.888037 0.061 Uiso 1 1 calc R U . . .
H22B H 0.745017 -0.018539 0.940846 0.061 Uiso 1 1 calc R U . . .
H22C H 0.803228 0.051263 0.869842 0.061 Uiso 1 1 calc R U . . .
C23 C 0.9056(6) 0.2498(5) 0.9484(2) 0.0459(12) Uani 1 1 d . . . . .
H23A H 1.008012 0.232633 0.916142 0.069 Uiso 1 1 calc R U . . .
H23B H 0.940638 0.166523 0.986505 0.069 Uiso 1 1 calc R U . . .
H23C H 0.900456 0.359111 0.959587 0.069 Uiso 1 1 calc R U . . .
C24 C 0.5460(6) 0.2496(5) 0.97589(19) 0.0428(12) Uani 1 1 d . . . . .
H24A H 0.533802 0.358224 0.988202 0.064 Uiso 1 1 calc R U . . .
H24B H 0.593285 0.165105 1.012700 0.064 Uiso 1 1 calc R U . . .
H24C H 0.413942 0.234024 0.961126 0.064 Uiso 1 1 calc R U . . .
N1 N 0.2613(4) 0.8547(4) 0.47671(16) 0.0232(8) Uani 1 1 d . . . . .
H5 H 0.253(5) 0.811(4) 0.4373(17) 0.035 Uiso 1 1 d . U . . .
N2 N 0.4540(4) 0.7165(4) 0.69692(14) 0.0264(8) Uani 1 1 d . . . . .
H2A H 0.451516 0.821565 0.697020 0.032 Uiso 1 1 calc R U . . .
O1 O 0.3402(4) 1.0311(3) 0.64053(12) 0.0307(7) Uani 1 1 d . . . . .
O2 O 0.4106(4) 0.5223(3) 0.63741(12) 0.0295(7) Uani 1 1 d . . . . .
O3 O 0.9317(4) 0.2698(3) 0.80746(14) 0.0371(7) Uani 1 1 d D . . . .
H3O H 0.987(7) 0.294(5) 0.7706(13) 0.074(17) Uiso 1 1 d D . . . .
O1W O 0.2358(5) 0.7162(4) 0.37150(14) 0.0392(8) Uani 1 1 d D . . . .
H1W H 0.340(5) 0.649(5) 0.361(2) 0.078(18) Uiso 1 1 d D . . . .
H2W H 0.138(5) 0.680(6) 0.356(2) 0.10(2) Uiso 1 1 d D . . . .
O2W O 0.1380(4) 1.3067(4) 0.68917(14) 0.0360(7) Uani 1 1 d D . . . .
H3W H 0.198(7) 1.218(4) 0.674(2) 0.090(19) Uiso 1 1 d D . . . .
H4W H 0.216(7) 1.382(5) 0.681(3) 0.12(2) Uiso 1 1 d 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
C1 C2 1.375(5) . ?
C1 C6 1.400(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.359(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.372(4) . ?
C5 C6 1.398(5) . ?
C6 C7 1.477(5) . ?
C7 O1 1.255(4) . ?
C7 C8 1.430(5) . ?
C8 C9 1.370(5) . ?
C8 C10 1.492(5) . ?
C9 N1 1.336(4) . ?
C9 H9 0.9500 . ?
C10 O2 1.247(4) . ?
C10 N2 1.339(4) . ?
C11 C12 1.396(5) . ?
C11 C16 1.405(5) . ?
C11 N2 1.431(4) . ?
C12 C13 1.368(5) . ?
C12 H12 0.9500 . ?
C13 O3 1.380(4) . ?
C13 C14 1.401(5) . ?
C14 C15 1.398(5) . ?
C14 C21 1.530(5) . ?
C15 C16 1.394(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.541(5) . ?
C17 C19 1.528(5) . ?
C17 C18 1.532(5) . ?
C17 C20 1.534(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.535(5) . ?
C21 C23 1.536(5) . ?
C21 C24 1.541(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 H5 0.98(3) . ?
N2 H2A 0.8800 . ?
O3 H3O 0.873(19) . ?
O1W H1W 0.874(19) . ?
O1W H2W 0.861(19) . ?
O2W H3W 0.890(19) . ?
O2W H4W 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.8(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C6 119.9(4) . . ?
N1 C5 C4 119.1(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 C7 120.3(3) . . ?
C1 C6 C7 121.7(3) . . ?
O1 C7 C8 124.2(4) . . ?
O1 C7 C6 120.3(3) . . ?
C8 C7 C6 115.5(3) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 C10 115.3(3) . . ?
C7 C8 C10 124.9(3) . . ?
N1 C9 C8 123.7(4) . . ?
N1 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
O2 C10 N2 123.7(4) . . ?
O2 C10 C8 120.7(3) . . ?
N2 C10 C8 115.6(3) . . ?
C12 C11 C16 120.5(4) . . ?
C12 C11 N2 116.9(3) . . ?
C16 C11 N2 122.6(3) . . ?
C13 C12 C11 121.8(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 O3 120.4(4) . . ?
C12 C13 C14 120.5(4) . . ?
O3 C13 C14 119.1(4) . . ?
C15 C14 C13 116.0(4) . . ?
C15 C14 C21 121.8(3) . . ?
C13 C14 C21 122.2(3) . . ?
C16 C15 C14 125.8(4) . . ?
C16 C15 H15 117.1 . . ?
C14 C15 H15 117.1 . . ?
C15 C16 C11 115.3(3) . . ?
C15 C16 C17 121.2(3) . . ?
C11 C16 C17 123.3(4) . . ?
C19 C17 C18 109.5(3) . . ?
C19 C17 C20 108.6(3) . . ?
C18 C17 C20 106.5(3) . . ?
C19 C17 C16 108.6(3) . . ?
C18 C17 C16 112.7(3) . . ?
C20 C17 C16 110.8(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 C22 108.7(3) . . ?
C14 C21 C23 111.2(3) . . ?
C22 C21 C23 110.0(3) . . ?
C14 C21 C24 112.4(3) . . ?
C22 C21 C24 106.8(3) . . ?
C23 C21 C24 107.6(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C5 120.8(3) . . ?
C9 N1 H5 119(2) . . ?
C5 N1 H5 120(2) . . ?
C10 N2 C11 122.4(3) . . ?
C10 N2 H2A 118.8 . . ?
C11 N2 H2A 118.8 . . ?
C13 O3 H3O 108(3) . . ?
H1W O1W H2W 101(4) . . ?
H3W O2W H4W 108(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H5 O1W 0.98(3) 1.74(4) 2.709(4) 175(3) . yes
N2 H2A O1 0.88 1.99 2.697(4) 136.4 . yes
O3 H3O O2W 0.873(19) 2.00(2) 2.866(4) 170(4) 1_645 yes
O1W H1W O2 0.874(19) 2.01(2) 2.861(4) 164(5) 2_666 yes
O1W H2W O2W 0.861(19) 2.07(3) 2.882(4) 157(5) 2_576 yes
O2W H3W O1 0.890(19) 1.93(2) 2.824(4) 177(5) . yes
O2W H4W O2 0.88(2) 2.03(3) 2.881(4) 163(5) 1_565 yes

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate-water'
####################################################################### 
# 
# 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_KB1801_0m
_database_code_depnum_ccdc_archive 'CCDC 2494441'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor ethylene glycol'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O3, C2 H6 O2'
_chemical_formula_sum            'C26 H34 N2 O5'
_chemical_formula_weight         454.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0720(17)
_cell_length_b                   9.552(2)
_cell_length_c                   20.430(5)
_cell_angle_alpha                78.051(7)
_cell_angle_beta                 80.463(7)
_cell_angle_gamma                69.442(7)
_cell_volume                     1257.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8369
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.4

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            36568
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.307
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7604
_reflns_number_gt                4194
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0778P)²+0.0784P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7604
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2544(2) 1.01142(16) 0.47633(7) 0.0440(3) Uani 1 1 d . . . . .
C2 C -0.3428(2) 1.11954(19) 0.42283(8) 0.0543(4) Uani 1 1 d . . . . .
H2 H -0.325248 1.094010 0.380187 0.065 Uiso 1 1 calc R U . . .
C3 C -0.4548(3) 1.26272(19) 0.43393(9) 0.0618(5) Uani 1 1 d . . . . .
H3 H -0.512690 1.335217 0.398423 0.074 Uiso 1 1 calc R U . . .
C4 C -0.4836(3) 1.30191(18) 0.49742(9) 0.0617(4) Uani 1 1 d . . . . .
H4 H -0.563343 1.399426 0.504343 0.074 Uiso 1 1 calc R U . . .
C5 C -0.3956(3) 1.19815(17) 0.54977(8) 0.0534(4) Uani 1 1 d . . . . .
H5 H -0.414221 1.225901 0.592010 0.064 Uiso 1 1 calc R U . . .
C6 C -0.2772(2) 1.04987(15) 0.54038(7) 0.0433(3) Uani 1 1 d . . . . .
C7 C -0.1830(2) 0.93680(15) 0.59580(7) 0.0427(3) Uani 1 1 d . . . . .
C8 C -0.0840(2) 0.78542(15) 0.58192(6) 0.0409(3) Uani 1 1 d . . . . .
C9 C -0.0684(2) 0.75835(16) 0.51761(6) 0.0440(3) Uani 1 1 d . . . . .
H9 H -0.000165 0.660258 0.508953 0.053 Uiso 1 1 calc R U . . .
C10 C -0.0050(2) 0.65036(16) 0.63385(7) 0.0453(3) Uani 1 1 d . . . . .
C11 C 0.0048(2) 0.56866(14) 0.75657(6) 0.0424(3) Uani 1 1 d . . . . .
C12 C 0.1917(2) 0.45629(16) 0.75961(7) 0.0469(4) Uani 1 1 d . . . . .
H12 H 0.288021 0.452495 0.722442 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2387(2) 0.34955(16) 0.81655(7) 0.0472(4) Uani 1 1 d . . . . .
C14 C 0.0994(2) 0.35534(15) 0.87400(6) 0.0462(4) Uani 1 1 d . . . . .
C15 C -0.0876(2) 0.46817(15) 0.86812(6) 0.0464(4) Uani 1 1 d . . . . .
H15 H -0.183033 0.472490 0.905566 0.056 Uiso 1 1 calc R U . . .
C16 C -0.1456(2) 0.57584(15) 0.81111(6) 0.0439(3) Uani 1 1 d . . . . .
C17 C -0.3600(3) 0.69355(18) 0.81098(7) 0.0593(5) Uani 1 1 d . . . . .
C18 C -0.4610(3) 0.7012(3) 0.74832(9) 0.0811(6) Uani 1 1 d . . . . .
H18A H -0.395423 0.747101 0.709190 0.122 Uiso 1 1 calc R U . . .
H18B H -0.602099 0.760534 0.753761 0.122 Uiso 1 1 calc R U . . .
H18C H -0.448291 0.600589 0.743047 0.122 Uiso 1 1 calc R U . . .
C19 C -0.3482(4) 0.8479(2) 0.81522(9) 0.0882(7) Uani 1 1 d . . . . .
H19A H -0.259122 0.876064 0.778048 0.132 Uiso 1 1 calc R U . . .
H19B H -0.296798 0.842514 0.856650 0.132 Uiso 1 1 calc R U . . .
H19C H -0.481185 0.922287 0.813644 0.132 Uiso 1 1 calc R U . . .
C20 C -0.5022(3) 0.6529(3) 0.87206(10) 0.0891(7) Uani 1 1 d . . . . .
H20A H -0.637695 0.722226 0.867996 0.134 Uiso 1 1 calc R U . . .
H20B H -0.456203 0.659688 0.912581 0.134 Uiso 1 1 calc R U . . .
H20C H -0.501201 0.551511 0.873628 0.134 Uiso 1 1 calc R U . . .
C21 C 0.1484(3) 0.24176(17) 0.93919(7) 0.0588(5) Uani 1 1 d . . . . .
C22 C 0.1785(4) 0.08275(18) 0.92629(9) 0.0833(7) Uani 1 1 d . . . . .
H22A H 0.058752 0.082714 0.910008 0.125 Uiso 1 1 calc R U . . .
H22B H 0.203046 0.012264 0.967423 0.125 Uiso 1 1 calc R U . . .
H22C H 0.292602 0.053535 0.893346 0.125 Uiso 1 1 calc R U . . .
C23 C 0.3392(4) 0.2464(3) 0.96389(10) 0.0907(7) Uani 1 1 d . . . . .
H23A H 0.453747 0.213725 0.931509 0.136 Uiso 1 1 calc R U . . .
H23B H 0.363276 0.180373 1.006198 0.136 Uiso 1 1 calc R U . . .
H23C H 0.319984 0.348072 0.969417 0.136 Uiso 1 1 calc R U . . .
C24 C -0.0252(3) 0.2778(2) 0.99575(8) 0.0782(6) Uani 1 1 d . . . . .
H24A H -0.050552 0.378187 1.004418 0.117 Uiso 1 1 calc R U . . .
H24B H 0.012062 0.206020 1.035805 0.117 Uiso 1 1 calc R U . . .
H24C H -0.145655 0.271800 0.982376 0.117 Uiso 1 1 calc R U . . .
N1 N -0.1457(2) 0.86507(14) 0.46694(6) 0.0465(3) Uani 1 1 d . . . . .
H1N H -0.130(3) 0.8415(19) 0.4256(9) 0.066(5) Uiso 1 1 d . . . . .
N2 N -0.0302(2) 0.67892(14) 0.69679(5) 0.0470(3) Uani 1 1 d . . . . .
H2N H -0.090(3) 0.7730(19) 0.6988(8) 0.059(5) Uiso 1 1 d . . . . .
O1 O -0.19305(19) 0.97342(11) 0.65229(5) 0.0593(3) Uani 1 1 d . . . . .
O2 O 0.0691(2) 0.52260(11) 0.61841(5) 0.0677(4) Uani 1 1 d . . . . .
O3 O 0.42181(19) 0.23624(13) 0.81753(6) 0.0681(4) Uani 1 1 d . . . . .
H3A H 0.497(2) 0.2480(16) 0.7779(11) 0.102 Uiso 1 1 calc R U . . .
C25 C 1.0786(3) 0.1443(2) 0.71805(8) 0.0618(4) Uani 1 1 d . . . . .
H25A H 1.177160 0.137537 0.747406 0.074 Uiso 1 1 calc R U . . .
H25B H 1.092167 0.041764 0.713898 0.074 Uiso 1 1 calc R U . . .
C26 C 0.8734(3) 0.2157(2) 0.75018(8) 0.0666(5) Uani 1 1 d . . . . .
H26A H 0.856622 0.156773 0.794194 0.080 Uiso 1 1 calc R U . . .
H26B H 0.862105 0.316071 0.756777 0.080 Uiso 1 1 calc R U . . .
O4 O 1.1261(2) 0.22019(14) 0.65435(6) 0.0675(4) Uani 1 1 d . . . . .
H4O H 1.102(4) 0.317(3) 0.6514(12) 0.111(8) Uiso 1 1 d . . . . .
O5 O 0.71139(19) 0.22867(14) 0.71260(6) 0.0636(3) Uani 1 1 d . . . . .
H5O H 0.743(3) 0.150(2) 0.6952(10) 0.082(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
C1 N1 1.3747(19) . ?
C1 C2 1.399(2) . ?
C1 C6 1.400(2) . ?
C2 C3 1.363(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.4596(19) . ?
C7 O1 1.2577(17) . ?
C7 C8 1.4333(19) . ?
C8 C9 1.3703(19) . ?
C8 C10 1.4917(19) . ?
C9 N1 1.3300(17) . ?
C9 H9 0.9300 . ?
C10 O2 1.2325(17) . ?
C10 N2 1.3397(18) . ?
C11 C12 1.381(2) . ?
C11 C16 1.4020(19) . ?
C11 N2 1.4305(16) . ?
C12 C13 1.3792(19) . ?
C12 H12 0.9300 . ?
C13 O3 1.3655(18) . ?
C13 C14 1.398(2) . ?
C14 C15 1.387(2) . ?
C14 C21 1.5368(19) . ?
C15 C16 1.3959(18) . ?
C15 H15 0.9300 . ?
C16 C17 1.538(2) . ?
C17 C19 1.527(3) . ?
C17 C20 1.542(2) . ?
C17 C18 1.543(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.530(2) . ?
C21 C23 1.534(3) . ?
C21 C24 1.536(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1N 0.897(18) . ?
N2 H2N 0.855(17) . ?
O3 H3A 0.90(2) . ?
C25 O4 1.403(2) . ?
C25 C26 1.475(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O5 1.438(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
O4 H4O 0.87(2) . ?
O5 H5O 0.84(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 120.39(13) . . ?
N1 C1 C6 118.94(12) . . ?
C2 C1 C6 120.66(14) . . ?
C3 C2 C1 119.23(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.96(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.36(16) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.53(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.22(13) . . ?
C1 C6 C7 120.34(13) . . ?
C5 C6 C7 121.42(13) . . ?
O1 C7 C8 123.29(12) . . ?
O1 C7 C6 120.38(13) . . ?
C8 C7 C6 116.32(12) . . ?
C9 C8 C7 119.09(12) . . ?
C9 C8 C10 116.35(12) . . ?
C7 C8 C10 124.46(12) . . ?
N1 C9 C8 123.42(13) . . ?
N1 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
O2 C10 N2 124.16(13) . . ?
O2 C10 C8 120.56(12) . . ?
N2 C10 C8 115.21(12) . . ?
C12 C11 C16 120.80(12) . . ?
C12 C11 N2 118.29(12) . . ?
C16 C11 N2 120.90(13) . . ?
C13 C12 C11 121.47(13) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
O3 C13 C12 120.40(13) . . ?
O3 C13 C14 119.02(12) . . ?
C12 C13 C14 120.58(13) . . ?
C15 C14 C13 115.85(12) . . ?
C15 C14 C21 121.92(13) . . ?
C13 C14 C21 122.22(13) . . ?
C14 C15 C16 125.93(13) . . ?
C14 C15 H15 117.0 . . ?
C16 C15 H15 117.0 . . ?
C15 C16 C11 115.24(13) . . ?
C15 C16 C17 120.61(12) . . ?
C11 C16 C17 124.14(12) . . ?
C19 C17 C16 109.31(17) . . ?
C19 C17 C20 107.39(15) . . ?
C16 C17 C20 111.58(13) . . ?
C19 C17 C18 111.11(15) . . ?
C16 C17 C18 111.53(13) . . ?
C20 C17 C18 105.82(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C23 110.76(17) . . ?
C22 C21 C24 107.23(15) . . ?
C23 C21 C24 107.59(15) . . ?
C22 C21 C14 109.28(13) . . ?
C23 C21 C14 110.05(15) . . ?
C24 C21 C14 111.90(13) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C1 121.62(12) . . ?
C9 N1 H1N 119.9(11) . . ?
C1 N1 H1N 118.5(11) . . ?
C10 N2 C11 126.27(12) . . ?
C10 N2 H2N 111.8(11) . . ?
C11 N2 H2N 121.2(11) . . ?
C13 O3 H3A 109.5 . . ?
O4 C25 C26 114.93(15) . . ?
O4 C25 H25A 108.5 . . ?
C26 C25 H25A 108.5 . . ?
O4 C25 H25B 108.5 . . ?
C26 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
O5 C26 C25 114.33(14) . . ?
O5 C26 H26A 108.7 . . ?
C25 C26 H26A 108.7 . . ?
O5 C26 H26B 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C25 O4 H4O 115.8(15) . . ?
C26 O5 H5O 108.4(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
N1 C1 C2 C3 178.11(14) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
N1 C1 C6 C5 -177.44(13) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
N1 C1 C6 C7 1.3(2) . . . . ?
C2 C1 C6 C7 -179.42(13) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C7 -179.52(14) . . . . ?
C1 C6 C7 O1 175.71(14) . . . . ?
C5 C6 C7 O1 -5.6(2) . . . . ?
C1 C6 C7 C8 -5.2(2) . . . . ?
C5 C6 C7 C8 173.56(13) . . . . ?
O1 C7 C8 C9 -175.46(14) . . . . ?
C6 C7 C8 C9 5.4(2) . . . . ?
O1 C7 C8 C10 8.2(2) . . . . ?
C6 C7 C8 C10 -170.89(13) . . . . ?
C7 C8 C9 N1 -1.9(2) . . . . ?
C10 C8 C9 N1 174.67(13) . . . . ?
C9 C8 C10 O2 -0.1(2) . . . . ?
C7 C8 C10 O2 176.27(15) . . . . ?
C9 C8 C10 N2 -177.17(13) . . . . ?
C7 C8 C10 N2 -0.8(2) . . . . ?
C16 C11 C12 C13 -1.4(2) . . . . ?
N2 C11 C12 C13 177.58(14) . . . . ?
C11 C12 C13 O3 177.62(14) . . . . ?
C11 C12 C13 C14 -2.1(2) . . . . ?
O3 C13 C14 C15 -176.45(14) . . . . ?
C12 C13 C14 C15 3.3(2) . . . . ?
O3 C13 C14 C21 2.3(2) . . . . ?
C12 C13 C14 C21 -177.97(15) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C21 C14 C15 C16 -179.92(15) . . . . ?
C14 C15 C16 C11 -2.1(2) . . . . ?
C14 C15 C16 C17 178.95(15) . . . . ?
C12 C11 C16 C15 3.3(2) . . . . ?
N2 C11 C16 C15 -175.62(13) . . . . ?
C12 C11 C16 C17 -177.73(15) . . . . ?
N2 C11 C16 C17 3.3(2) . . . . ?
C15 C16 C17 C19 106.13(16) . . . . ?
C11 C16 C17 C19 -72.76(19) . . . . ?
C15 C16 C17 C20 -12.5(2) . . . . ?
C11 C16 C17 C20 168.61(16) . . . . ?
C15 C16 C17 C18 -130.61(16) . . . . ?
C11 C16 C17 C18 50.5(2) . . . . ?
C15 C14 C21 C22 114.22(18) . . . . ?
C13 C14 C21 C22 -64.4(2) . . . . ?
C15 C14 C21 C23 -123.95(18) . . . . ?
C13 C14 C21 C23 57.4(2) . . . . ?
C15 C14 C21 C24 -4.4(2) . . . . ?
C13 C14 C21 C24 176.98(16) . . . . ?
C8 C9 N1 C1 -2.3(2) . . . . ?
C2 C1 N1 C9 -176.75(14) . . . . ?
C6 C1 N1 C9 2.5(2) . . . . ?
O2 C10 N2 C11 -6.5(3) . . . . ?
C8 C10 N2 C11 170.46(14) . . . . ?
C12 C11 N2 C10 53.8(2) . . . . ?
C16 C11 N2 C10 -127.20(16) . . . . ?
O4 C25 C26 O5 60.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O4 0.897(18) 1.841(19) 2.7323(18) 171.7(17) 2_666 yes
N2 H2N O1 0.855(17) 1.895(17) 2.6606(17) 148.2(15) . yes
O3 H3A O5 0.90 1.83 2.7018(18) 162.2 . yes
O4 H4O O2 0.87(2) 1.88(2) 2.7290(17) 163(2) 1_655 yes
O5 H5O O1 0.84(2) 1.94(2) 2.7803(17) 177(2) 1_645 yes

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate-ethylene glycol'
####################################################################### 
# 
# 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_cu_VA216_0m_IVA-DACA
_database_code_depnum_ccdc_archive 'CCDC 2494439'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor di acetic acid solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H28 N2 O3, 2(C2 H4 O2)'
_chemical_formula_sum            'C28 H36 N2 O7'
_chemical_formula_weight         512.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.796(2)
_cell_length_b                   6.5459(9)
_cell_length_c                   25.136(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.131(7)
_cell_angle_gamma                90
_cell_volume                     2766.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6001
_cell_measurement_theta_min      5.26
_cell_measurement_theta_max      66.89

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.725
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-III C14'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            15955
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.686
_diffrn_reflns_theta_max         62.998
_diffrn_reflns_theta_full        62.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             4333
_reflns_number_gt                3195
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.2664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4333
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1400
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20933(11) 0.8460(3) 0.20799(8) 0.0349(4) Uani 1 1 d . . . . .
C2 C 0.12866(11) 0.8517(3) 0.17518(10) 0.0451(5) Uani 1 1 d . . . . .
H2 H 0.088707 0.858531 0.192579 0.054 Uiso 1 1 calc R U . . .
C3 C 0.10830(13) 0.8472(4) 0.11783(10) 0.0515(6) Uani 1 1 d . . . . .
H3 H 0.053789 0.850617 0.095278 0.062 Uiso 1 1 calc R U . . .
C4 C 0.16682(13) 0.8377(4) 0.09202(10) 0.0501(6) Uani 1 1 d . . . . .
H4 H 0.151878 0.836191 0.052103 0.060 Uiso 1 1 calc R U . . .
C5 C 0.24576(12) 0.8305(4) 0.12404(9) 0.0429(5) Uani 1 1 d . . . . .
H5 H 0.285180 0.822927 0.106180 0.052 Uiso 1 1 calc R U . . .
C6 C 0.26872(11) 0.8342(3) 0.18336(8) 0.0349(5) Uani 1 1 d . . . . .
C7 C 0.35283(10) 0.8236(3) 0.21790(8) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.36894(10) 0.8394(3) 0.27766(8) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.30694(11) 0.8495(3) 0.29856(8) 0.0346(4) Uani 1 1 d . . . . .
H9 H 0.318724 0.855728 0.338224 0.042 Uiso 1 1 calc R U . . .
C10 C 0.45035(11) 0.8398(3) 0.32011(8) 0.0322(4) Uani 1 1 d . . . . .
C11 C 0.59316(10) 0.8194(3) 0.33352(8) 0.0349(5) Uani 1 1 d . . . . .
C12 C 0.64740(11) 0.9537(3) 0.32309(8) 0.0362(5) Uani 1 1 d . . . . .
C13 C 0.72609(11) 0.9326(3) 0.35894(8) 0.0375(5) Uani 1 1 d . . . . .
H13 H 0.764611 1.021572 0.352777 0.045 Uiso 1 1 calc R U . . .
C14 C 0.75258(11) 0.7929(3) 0.40272(8) 0.0368(5) Uani 1 1 d . . . . .
C15 C 0.69506(11) 0.6641(4) 0.41095(8) 0.0402(5) Uani 1 1 d . . . . .
C16 C 0.61644(11) 0.6784(3) 0.37619(8) 0.0393(5) Uani 1 1 d . . . . .
H16 H 0.577961 0.588592 0.382076 0.047 Uiso 1 1 calc R U . . .
C17 C 0.62500(11) 1.1145(4) 0.27623(9) 0.0456(5) Uani 1 1 d . . . . .
C18 C 0.69410(14) 1.2629(5) 0.28141(13) 0.0706(9) Uani 1 1 d . . . . .
H18A H 0.738396 1.188347 0.275404 0.106 Uiso 1 1 calc R U . . .
H18B H 0.711725 1.324069 0.319074 0.106 Uiso 1 1 calc R U . . .
H18C H 0.676192 1.370871 0.253038 0.106 Uiso 1 1 calc R U . . .
C19 C 0.60415(14) 1.0114(5) 0.21840(9) 0.0595(7) Uani 1 1 d . . . . .
H19A H 0.589949 1.115827 0.188842 0.089 Uiso 1 1 calc R U . . .
H19B H 0.559044 0.918678 0.213138 0.089 Uiso 1 1 calc R U . . .
H19C H 0.650153 0.933653 0.216268 0.089 Uiso 1 1 calc R U . . .
C20 C 0.55390(13) 1.2464(4) 0.27841(11) 0.0533(6) Uani 1 1 d . . . . .
H20A H 0.550570 1.369842 0.255709 0.080 Uiso 1 1 calc R U . . .
H20B H 0.561515 1.284969 0.317504 0.080 Uiso 1 1 calc R U . . .
H20C H 0.504571 1.167775 0.263411 0.080 Uiso 1 1 calc R U . . .
C21 C 0.84003(11) 0.7846(4) 0.44047(8) 0.0425(5) Uani 1 1 d . . . . .
C22 C 0.89187(12) 0.9391(5) 0.42282(11) 0.0576(7) Uani 1 1 d . . . . .
H22A H 0.890526 0.909347 0.384312 0.086 Uiso 1 1 calc R U . . .
H22B H 0.946756 0.929604 0.448457 0.086 Uiso 1 1 calc R U . . .
H22C H 0.871565 1.077339 0.424395 0.086 Uiso 1 1 calc R U . . .
C23 C 0.87447(13) 0.5719(4) 0.43808(10) 0.0538(6) Uani 1 1 d . . . . .
H23A H 0.870624 0.540356 0.399169 0.081 Uiso 1 1 calc R U . . .
H23B H 0.844447 0.470323 0.451526 0.081 Uiso 1 1 calc R U . . .
H23C H 0.930391 0.568946 0.462024 0.081 Uiso 1 1 calc R U . . .
C24 C 0.84502(14) 0.8339(5) 0.50131(9) 0.0622(8) Uani 1 1 d . . . . .
H24A H 0.825909 0.973266 0.503104 0.093 Uiso 1 1 calc R U . . .
H24B H 0.900365 0.822512 0.526030 0.093 Uiso 1 1 calc R U . . .
H24C H 0.811981 0.737240 0.513606 0.093 Uiso 1 1 calc R U . . .
O1 O 0.40600(7) 0.8032(2) 0.19553(6) 0.0421(4) Uani 1 1 d . . . . .
O2 O 0.45802(8) 0.8599(3) 0.37064(6) 0.0427(4) Uani 1 1 d . . . . .
O3 O 0.71564(9) 0.5220(3) 0.45313(6) 0.0538(5) Uani 1 1 d . . . . .
H1O H 0.6734(17) 0.450(5) 0.4489(12) 0.073(9) Uiso 1 1 d . . . . .
N1 N 0.23106(9) 0.8509(3) 0.26600(7) 0.0368(4) Uani 1 1 d . . . . .
H1N H 0.1972(12) 0.858(4) 0.2829(9) 0.037(6) Uiso 1 1 d . . . . .
N2 N 0.51054(9) 0.8194(3) 0.30010(7) 0.0366(4) Uani 1 1 d . . . . .
H2N H 0.4959(14) 0.816(4) 0.2672(12) 0.051(7) Uiso 1 1 d . . . . .
C25 C 0.65866(16) 1.1481(4) 0.53362(10) 0.0601(7) Uani 1 1 d . . . . .
H25A H 0.697693 1.037086 0.544398 0.090 Uiso 1 1 calc R U . . .
H25B H 0.627204 1.149908 0.559142 0.090 Uiso 1 1 calc R U . . .
H25C H 0.686401 1.278829 0.536021 0.090 Uiso 1 1 calc R U . . .
C26 C 0.60489(11) 1.1152(4) 0.47471(8) 0.0397(5) Uani 1 1 d . . . . .
O4 O 0.56692(9) 0.9418(3) 0.46820(6) 0.0483(4) Uani 1 1 d . . . . .
H2O H 0.5323(17) 0.920(5) 0.4340(14) 0.072 Uiso 1 1 d . U . . .
O5 O 0.59655(9) 1.2371(3) 0.43722(7) 0.0564(5) Uani 1 1 d . . . . .
C27 C 0.40936(15) 0.1765(4) 0.09586(11) 0.0585(7) Uani 1 1 d . . . . .
H27A H 0.361776 0.157890 0.062831 0.088 Uiso 1 1 calc R U . . .
H27B H 0.421985 0.048075 0.116971 0.088 Uiso 1 1 calc R U . . .
H27C H 0.454183 0.216457 0.083616 0.088 Uiso 1 1 calc R U . . .
C28 C 0.39439(12) 0.3389(4) 0.13254(9) 0.0467(6) Uani 1 1 d . . . . .
O6 O 0.43629(10) 0.5045(3) 0.13447(7) 0.0552(5) Uani 1 1 d . . . . .
H3O H 0.4231(17) 0.591(6) 0.1546(14) 0.083 Uiso 1 1 d . U . . .
O7 O 0.34771(11) 0.3211(3) 0.15730(9) 0.0763(6) Uani 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
C1 N1 1.381(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.402(3) . ?
C2 C3 1.367(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.411(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.465(3) . ?
C7 O1 1.256(2) . ?
C7 C8 1.438(3) . ?
C8 C9 1.370(3) . ?
C8 C10 1.491(3) . ?
C9 N1 1.330(2) . ?
C9 H9 0.9500 . ?
C10 O2 1.239(2) . ?
C10 N2 1.331(2) . ?
C11 C16 1.373(3) . ?
C11 C12 1.392(3) . ?
C11 N2 1.434(2) . ?
C12 C13 1.402(3) . ?
C12 C17 1.532(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 C21 1.535(3) . ?
C15 O3 1.367(3) . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C19 1.534(3) . ?
C17 C18 1.539(3) . ?
C17 C20 1.547(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.529(3) . ?
C21 C23 1.530(4) . ?
C21 C24 1.537(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O3 H1O 0.86(3) . ?
N1 H1N 0.84(2) . ?
N2 H2N 0.78(3) . ?
C25 C26 1.492(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O5 1.206(3) . ?
C26 O4 1.304(3) . ?
O4 H2O 0.89(3) . ?
C27 C28 1.487(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O7 1.196(3) . ?
C28 O6 1.307(3) . ?
O6 H3O 0.84(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
N1 C1 C6 118.71(16) . . ?
N1 C1 C2 119.92(18) . . ?
C6 C1 C2 121.37(19) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.70(19) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.17(17) . . ?
C1 C6 C7 121.09(17) . . ?
C5 C6 C7 120.74(17) . . ?
O1 C7 C8 123.62(16) . . ?
O1 C7 C6 120.85(17) . . ?
C8 C7 C6 115.53(16) . . ?
C9 C8 C7 119.61(17) . . ?
C9 C8 C10 116.17(17) . . ?
C7 C8 C10 124.20(16) . . ?
N1 C9 C8 123.16(18) . . ?
N1 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
O2 C10 N2 124.48(17) . . ?
O2 C10 C8 119.24(16) . . ?
N2 C10 C8 116.28(17) . . ?
C16 C11 C12 121.43(17) . . ?
C16 C11 N2 116.52(17) . . ?
C12 C11 N2 122.05(18) . . ?
C11 C12 C13 115.15(19) . . ?
C11 C12 C17 123.84(17) . . ?
C13 C12 C17 121.01(17) . . ?
C14 C13 C12 125.60(18) . . ?
C14 C13 H13 117.2 . . ?
C12 C13 H13 117.2 . . ?
C13 C14 C15 116.18(17) . . ?
C13 C14 C21 121.66(18) . . ?
C15 C14 C21 122.15(19) . . ?
O3 C15 C16 119.50(18) . . ?
O3 C15 C14 120.26(17) . . ?
C16 C15 C14 120.24(19) . . ?
C11 C16 C15 121.39(18) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C12 C17 C19 110.3(2) . . ?
C12 C17 C18 111.68(17) . . ?
C19 C17 C18 107.2(2) . . ?
C12 C17 C20 111.45(17) . . ?
C19 C17 C20 109.42(18) . . ?
C18 C17 C20 106.6(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C23 107.62(19) . . ?
C22 C21 C14 112.52(18) . . ?
C23 C21 C14 110.23(19) . . ?
C22 C21 C24 107.8(2) . . ?
C23 C21 C24 109.7(2) . . ?
C14 C21 C24 108.91(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 O3 H1O 106(2) . . ?
C9 N1 C1 121.75(16) . . ?
C9 N1 H1N 116.0(14) . . ?
C1 N1 H1N 122.2(14) . . ?
C10 N2 C11 125.18(17) . . ?
C10 N2 H2N 111.8(17) . . ?
C11 N2 H2N 122.8(17) . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C26 O4 123.52(19) . . ?
O5 C26 C25 123.7(2) . . ?
O4 C26 C25 112.8(2) . . ?
C26 O4 H2O 115(2) . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O7 C28 O6 123.1(2) . . ?
O7 C28 C27 123.3(2) . . ?
O6 C28 C27 113.57(19) . . ?
C28 O6 H3O 108(2) . . ?

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
N1 C1 C2 C3 179.8(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
N1 C1 C6 C5 -179.65(19) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
N1 C1 C6 C7 1.0(3) . . . . ?
C2 C1 C6 C7 -178.6(2) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 179.1(2) . . . . ?
C1 C6 C7 O1 176.61(19) . . . . ?
C5 C6 C7 O1 -2.7(3) . . . . ?
C1 C6 C7 C8 -3.8(3) . . . . ?
C5 C6 C7 C8 176.87(19) . . . . ?
O1 C7 C8 C9 -176.25(19) . . . . ?
C6 C7 C8 C9 4.2(3) . . . . ?
O1 C7 C8 C10 1.8(3) . . . . ?
C6 C7 C8 C10 -177.70(17) . . . . ?
C7 C8 C9 N1 -1.9(3) . . . . ?
C10 C8 C9 N1 179.87(18) . . . . ?
C9 C8 C10 O2 -3.8(3) . . . . ?
C7 C8 C10 O2 178.00(19) . . . . ?
C9 C8 C10 N2 176.63(18) . . . . ?
C7 C8 C10 N2 -1.5(3) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
N2 C11 C12 C13 -179.13(18) . . . . ?
C16 C11 C12 C17 -179.9(2) . . . . ?
N2 C11 C12 C17 0.8(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C17 C12 C13 C14 179.7(2) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C14 C21 -178.78(19) . . . . ?
C13 C14 C15 O3 -179.84(19) . . . . ?
C21 C14 C15 O3 -1.0(3) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C21 C14 C15 C16 179.25(19) . . . . ?
C12 C11 C16 C15 0.3(3) . . . . ?
N2 C11 C16 C15 179.63(19) . . . . ?
O3 C15 C16 C11 179.7(2) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C11 C12 C17 C19 -70.5(2) . . . . ?
C13 C12 C17 C19 109.4(2) . . . . ?
C11 C12 C17 C18 170.4(2) . . . . ?
C13 C12 C17 C18 -9.7(3) . . . . ?
C11 C12 C17 C20 51.3(3) . . . . ?
C13 C12 C17 C20 -128.8(2) . . . . ?
C13 C14 C21 C22 -1.8(3) . . . . ?
C15 C14 C21 C22 179.4(2) . . . . ?
C13 C14 C21 C23 -122.0(2) . . . . ?
C15 C14 C21 C23 59.3(3) . . . . ?
C13 C14 C21 C24 117.7(2) . . . . ?
C15 C14 C21 C24 -61.1(3) . . . . ?
C8 C9 N1 C1 -1.2(3) . . . . ?
C6 C1 N1 C9 1.6(3) . . . . ?
C2 C1 N1 C9 -178.76(19) . . . . ?
O2 C10 N2 C11 -0.6(3) . . . . ?
C8 C10 N2 C11 178.87(19) . . . . ?
C16 C11 N2 C10 55.8(3) . . . . ?
C12 C11 N2 C10 -124.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H1O O5 0.86(3) 1.91(3) 2.752(2) 166(3) 1_545 yes
N1 H1N O7 0.84(2) 1.93(2) 2.737(2) 158(2) 2 yes
N2 H2N O1 0.78(3) 1.98(3) 2.679(2) 149(2) . yes
O4 H2O O2 0.89(3) 1.75(3) 2.635(2) 173(3) . yes
O6 H3O O1 0.84(4) 1.81(4) 2.648(2) 171(3) . yes

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetic acid'
####################################################################### 
# 
# 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_KB1747_0m
_database_code_depnum_ccdc_archive 'CCDC 2494437'
loop_
_audit_author_name
_audit_author_address
'sunil Kumar Nechipadappu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-10-10 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        'ivacaftor hydrobromide acetic acid solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H29 N2 O3, C2 H4 O2, Br'
_chemical_formula_sum            'C26 H33 Br N2 O5'
_chemical_formula_weight         533.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   28.4445(15)
_cell_length_b                   9.0341(5)
_cell_length_c                   10.3513(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2660.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7364
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.18

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.582
_shelx_estimated_absorpt_T_min   0.743
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5684
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22564
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.365
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.898
_reflns_number_total             5719
_reflns_number_gt                3597
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_max     0.720
_reflns_Friedel_fraction_full    0.784

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²+1.2151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1162 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5719
_refine_ls_number_parameters     334
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.83747(19) 0.3355(5) 0.1396(5) 0.0319(12) Uani 1 1 d . . . . .
C2 C 0.87379(19) 0.3827(6) 0.0575(5) 0.0420(13) Uani 1 1 d . . . . .
H2 H 0.870913 0.469219 0.009439 0.050 Uiso 1 1 calc R U . . .
C3 C 0.9138(2) 0.2974(6) 0.0503(6) 0.0517(15) Uani 1 1 d . . . . .
H3 H 0.938139 0.326710 -0.003784 0.062 Uiso 1 1 calc R U . . .
C4 C 0.9185(2) 0.1677(6) 0.1226(6) 0.0529(16) Uani 1 1 d . . . . .
H4 H 0.946034 0.112693 0.117028 0.063 Uiso 1 1 calc R U . . .
C5 C 0.88299(18) 0.1212(5) 0.2011(6) 0.0409(13) Uani 1 1 d . . . . .
H5 H 0.886266 0.034177 0.248200 0.049 Uiso 1 1 calc R U . . .
C6 C 0.84130(17) 0.2050(5) 0.2111(5) 0.0309(11) Uani 1 1 d . . . . .
C7 C 0.80254(19) 0.1610(5) 0.2900(5) 0.0317(12) Uani 1 1 d . . . . .
C8 C 0.76448(17) 0.2564(5) 0.3052(4) 0.0268(10) Uani 1 1 d . . . . .
C9 C 0.76223(17) 0.3821(5) 0.2280(4) 0.0309(11) Uani 1 1 d . . . . .
H9 H 0.735822 0.442591 0.232221 0.037 Uiso 1 1 calc R U . . .
C10 C 0.72573(18) 0.2156(5) 0.3941(4) 0.0312(11) Uani 1 1 d . . . . .
C11 C 0.65654(18) 0.2903(5) 0.5156(4) 0.0301(11) Uani 1 1 d . . . . .
C12 C 0.66565(17) 0.2616(5) 0.6450(4) 0.0326(11) Uani 1 1 d . . . . .
H12 H 0.696426 0.265126 0.675195 0.039 Uiso 1 1 calc R U . . .
C13 C 0.62952(19) 0.2280(5) 0.7296(5) 0.0351(12) Uani 1 1 d . . . . .
C14 C 0.58279(17) 0.2257(5) 0.6867(5) 0.0357(12) Uani 1 1 d . . . . .
C15 C 0.57566(18) 0.2558(5) 0.5568(5) 0.0370(12) Uani 1 1 d . . . . .
H15 H 0.544755 0.254250 0.527479 0.044 Uiso 1 1 calc R U . . .
C16 C 0.61062(16) 0.2883(5) 0.4652(5) 0.0333(11) Uani 1 1 d . . . . .
C17 C 0.5981(2) 0.3167(6) 0.3238(5) 0.0433(13) Uani 1 1 d . . . . .
C18 C 0.6204(3) 0.2008(8) 0.2338(6) 0.081(2) Uani 1 1 d . . . . .
H18A H 0.610473 0.218600 0.146574 0.122 Uiso 1 1 calc R U . . .
H18B H 0.610721 0.103562 0.259957 0.122 Uiso 1 1 calc R U . . .
H18C H 0.654056 0.208006 0.238813 0.122 Uiso 1 1 calc R U . . .
C19 C 0.6142(3) 0.4727(7) 0.2813(7) 0.078(2) Uani 1 1 d . . . . .
H19A H 0.647684 0.480653 0.290825 0.118 Uiso 1 1 calc R U . . .
H19B H 0.599115 0.545967 0.334114 0.118 Uiso 1 1 calc R U . . .
H19C H 0.605853 0.488385 0.192453 0.118 Uiso 1 1 calc R U . . .
C20 C 0.5448(2) 0.3129(8) 0.2999(7) 0.079(2) Uani 1 1 d . . . . .
H20A H 0.538539 0.336192 0.211087 0.118 Uiso 1 1 calc R U . . .
H20B H 0.529680 0.384303 0.354546 0.118 Uiso 1 1 calc R U . . .
H20C H 0.532993 0.215898 0.319169 0.118 Uiso 1 1 calc R U . . .
C21 C 0.54164(19) 0.1953(6) 0.7786(5) 0.0448(14) Uani 1 1 d . . . . .
C22 C 0.5474(2) 0.0446(7) 0.8449(6) 0.072(2) Uani 1 1 d . . . . .
H22A H 0.546371 -0.032531 0.781115 0.108 Uiso 1 1 calc R U . . .
H22B H 0.522434 0.030413 0.905982 0.108 Uiso 1 1 calc R U . . .
H22C H 0.577090 0.041417 0.889031 0.108 Uiso 1 1 calc R U . . .
C23 C 0.5404(2) 0.3172(7) 0.8829(6) 0.0659(18) Uani 1 1 d . . . . .
H23A H 0.534410 0.411124 0.842794 0.099 Uiso 1 1 calc R U . . .
H23B H 0.570078 0.320431 0.926844 0.099 Uiso 1 1 calc R U . . .
H23C H 0.515875 0.295792 0.943841 0.099 Uiso 1 1 calc R U . . .
C24 C 0.4941(2) 0.1960(8) 0.7077(6) 0.080(2) Uani 1 1 d . . . . .
H24A H 0.488617 0.292237 0.671319 0.119 Uiso 1 1 calc R U . . .
H24B H 0.469401 0.172798 0.767662 0.119 Uiso 1 1 calc R U . . .
H24C H 0.494543 0.123502 0.639943 0.119 Uiso 1 1 calc R U . . .
N1 N 0.79694(14) 0.4173(4) 0.1486(4) 0.0301(9) Uani 1 1 d D . . . .
H1N H 0.792(2) 0.495(5) 0.096(5) 0.08(2) Uiso 1 1 d D . . . .
N2 N 0.69635(13) 0.3217(4) 0.4329(4) 0.0318(9) Uani 1 1 d D . . . .
H2N H 0.7073(14) 0.410(3) 0.444(6) 0.040(13) Uiso 1 1 d D . . . .
O1 O 0.80523(15) 0.0304(4) 0.3475(4) 0.0470(10) Uani 1 1 d D . . . .
H1O H 0.7780(17) 0.018(11) 0.384(8) 0.17(4) Uiso 1 1 d D . . . .
O2 O 0.72054(11) 0.0828(3) 0.4259(3) 0.0353(9) Uani 1 1 d . . . . .
O3 O 0.63883(16) 0.1984(5) 0.8569(4) 0.0524(10) Uani 1 1 d D . . . .
H3O H 0.6673(12) 0.209(8) 0.881(7) 0.10(3) Uiso 1 1 d D . . . .
C25 C 0.8577(3) 0.3386(9) 0.5640(7) 0.090(3) Uani 1 1 d . . . . .
H25A H 0.844544 0.420559 0.517359 0.136 Uiso 1 1 calc R U . . .
H25B H 0.868878 0.265616 0.504000 0.136 Uiso 1 1 calc R U . . .
H25C H 0.883372 0.372635 0.616368 0.136 Uiso 1 1 calc R U . . .
C26 C 0.8210(3) 0.2719(7) 0.6481(6) 0.0606(17) Uani 1 1 d . . . . .
O4 O 0.79191(19) 0.1842(6) 0.6130(4) 0.0819(16) Uani 1 1 d . . . . .
O5 O 0.8242(2) 0.3181(6) 0.7683(5) 0.0844(17) Uani 1 1 d D . . . .
H5O H 0.7993(18) 0.277(8) 0.801(7) 0.10(3) Uiso 1 1 d D . . . .
Br01 Br 0.74698(2) 0.15430(5) 0.95149(10) 0.05226(17) Uani 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
C1 N1 1.373(6) . ?
C1 C6 1.396(6) . ?
C1 C2 1.404(7) . ?
C2 C3 1.375(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(7) . ?
C7 O1 1.324(5) . ?
C7 C8 1.393(7) . ?
C8 C9 1.389(6) . ?
C8 C10 1.482(6) . ?
C9 N1 1.323(6) . ?
C9 H9 0.9300 . ?
C10 O2 1.253(5) . ?
C10 N2 1.334(6) . ?
C11 C12 1.388(6) . ?
C11 C16 1.407(6) . ?
C11 N2 1.448(6) . ?
C12 C13 1.384(6) . ?
C12 H12 0.9300 . ?
C13 O3 1.370(6) . ?
C13 C14 1.401(7) . ?
C14 C15 1.387(7) . ?
C14 C21 1.533(7) . ?
C15 C16 1.405(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.529(7) . ?
C17 C20 1.534(8) . ?
C17 C18 1.539(8) . ?
C17 C19 1.546(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.533(8) . ?
C21 C24 1.539(8) . ?
C21 C23 1.542(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1N 0.90(2) . ?
N2 H2N 0.86(2) . ?
O1 H1O 0.87(3) . ?
O3 H3O 0.85(3) . ?
C25 C26 1.487(9) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 O4 1.202(7) . ?
C26 O5 1.315(8) . ?
O5 H5O 0.87(3) . ?

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
N1 C1 C6 119.0(5) . . ?
N1 C1 C2 119.7(5) . . ?
C6 C1 C2 121.3(5) . . ?
C3 C2 C1 118.1(5) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.4(5) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.7(5) . . ?
C1 C6 C7 118.5(4) . . ?
C5 C6 C7 122.8(4) . . ?
O1 C7 C8 123.1(5) . . ?
O1 C7 C6 117.4(5) . . ?
C8 C7 C6 119.5(4) . . ?
C9 C8 C7 118.5(4) . . ?
C9 C8 C10 121.7(4) . . ?
C7 C8 C10 119.6(4) . . ?
N1 C9 C8 121.3(4) . . ?
N1 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
O2 C10 N2 122.4(4) . . ?
O2 C10 C8 119.3(4) . . ?
N2 C10 C8 118.3(4) . . ?
C12 C11 C16 121.9(4) . . ?
C12 C11 N2 117.4(4) . . ?
C16 C11 N2 120.6(4) . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
O3 C13 C12 120.5(5) . . ?
O3 C13 C14 119.0(5) . . ?
C12 C13 C14 120.5(4) . . ?
C15 C14 C13 116.3(5) . . ?
C15 C14 C21 121.7(5) . . ?
C13 C14 C21 122.0(5) . . ?
C14 C15 C16 126.3(5) . . ?
C14 C15 H15 116.9 . . ?
C16 C15 H15 116.9 . . ?
C15 C16 C11 114.2(5) . . ?
C15 C16 C17 121.1(5) . . ?
C11 C16 C17 124.7(4) . . ?
C16 C17 C20 112.4(5) . . ?
C16 C17 C18 111.6(5) . . ?
C20 C17 C18 107.2(5) . . ?
C16 C17 C19 110.9(5) . . ?
C20 C17 C19 105.5(5) . . ?
C18 C17 C19 109.0(6) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 C22 110.8(5) . . ?
C14 C21 C24 112.0(5) . . ?
C22 C21 C24 108.1(5) . . ?
C14 C21 C23 108.9(4) . . ?
C22 C21 C23 108.9(5) . . ?
C24 C21 C23 108.1(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 N1 C1 122.6(4) . . ?
C9 N1 H1N 117(4) . . ?
C1 N1 H1N 120(4) . . ?
C10 N2 C11 121.8(4) . . ?
C10 N2 H2N 118(3) . . ?
C11 N2 H2N 113(4) . . ?
C7 O1 H1O 105(7) . . ?
C13 O3 H3O 116(5) . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 O5 122.9(7) . . ?
O4 C26 C25 125.0(6) . . ?
O5 C26 C25 112.1(6) . . ?
C26 O5 H5O 100(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
N1 C1 C2 C3 -179.6(5) . . . . ?
C6 C1 C2 C3 -0.7(8) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C2 C3 C4 C5 1.0(9) . . . . ?
C3 C4 C5 C6 -0.7(9) . . . . ?
N1 C1 C6 C5 179.8(5) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
N1 C1 C6 C7 0.6(7) . . . . ?
C2 C1 C6 C7 -178.3(5) . . . . ?
C4 C5 C6 C1 -0.3(8) . . . . ?
C4 C5 C6 C7 179.0(5) . . . . ?
C1 C6 C7 O1 173.9(4) . . . . ?
C5 C6 C7 O1 -5.3(7) . . . . ?
C1 C6 C7 C8 -7.2(7) . . . . ?
C5 C6 C7 C8 173.6(5) . . . . ?
O1 C7 C8 C9 -171.8(5) . . . . ?
C6 C7 C8 C9 9.3(7) . . . . ?
O1 C7 C8 C10 3.0(7) . . . . ?
C6 C7 C8 C10 -175.8(4) . . . . ?
C7 C8 C9 N1 -5.0(7) . . . . ?
C10 C8 C9 N1 -179.8(4) . . . . ?
C9 C8 C10 O2 154.7(4) . . . . ?
C7 C8 C10 O2 -19.9(7) . . . . ?
C9 C8 C10 N2 -22.5(7) . . . . ?
C7 C8 C10 N2 162.9(5) . . . . ?
C16 C11 C12 C13 0.8(7) . . . . ?
N2 C11 C12 C13 -178.8(4) . . . . ?
C11 C12 C13 O3 179.4(5) . . . . ?
C11 C12 C13 C14 -1.6(7) . . . . ?
O3 C13 C14 C15 -179.7(4) . . . . ?
C12 C13 C14 C15 1.2(7) . . . . ?
O3 C13 C14 C21 1.7(7) . . . . ?
C12 C13 C14 C21 -177.4(5) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C21 C14 C15 C16 178.5(5) . . . . ?
C14 C15 C16 C11 -0.6(7) . . . . ?
C14 C15 C16 C17 178.9(5) . . . . ?
C12 C11 C16 C15 0.2(6) . . . . ?
N2 C11 C16 C15 179.8(4) . . . . ?
C12 C11 C16 C17 -179.2(4) . . . . ?
N2 C11 C16 C17 0.4(7) . . . . ?
C15 C16 C17 C20 2.9(7) . . . . ?
C11 C16 C17 C20 -177.7(5) . . . . ?
C15 C16 C17 C18 -117.6(5) . . . . ?
C11 C16 C17 C18 61.8(7) . . . . ?
C15 C16 C17 C19 120.7(6) . . . . ?
C11 C16 C17 C19 -59.9(7) . . . . ?
C15 C14 C21 C22 123.3(5) . . . . ?
C13 C14 C21 C22 -58.1(6) . . . . ?
C15 C14 C21 C24 2.5(7) . . . . ?
C13 C14 C21 C24 -179.0(5) . . . . ?
C15 C14 C21 C23 -117.0(6) . . . . ?
C13 C14 C21 C23 61.6(6) . . . . ?
C8 C9 N1 C1 -1.7(7) . . . . ?
C6 C1 N1 C9 3.9(7) . . . . ?
C2 C1 N1 C9 -177.2(5) . . . . ?
O2 C10 N2 C11 0.4(7) . . . . ?
C8 C10 N2 C11 177.6(4) . . . . ?
C12 C11 N2 C10 74.4(6) . . . . ?
C16 C11 N2 C10 -105.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2 0.90(2) 1.97(4) 2.793(5) 153(6) 3_654 yes
N2 H2N Br01 0.86(2) 2.57(2) 3.415(4) 169(4) 3_654 yes
O1 H1O O2 0.87(3) 1.79(5) 2.585(5) 151(10) . yes
O3 H3O Br01 0.85(3) 2.43(3) 3.253(4) 162(7) . yes
O5 H5O Br01 0.87(3) 2.42(4) 3.258(6) 161(7) . yes

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.065


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetic acid'
