Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with 2,5-di­hydroxy­benzoic acid using microcrystal electron diffraction

A co-crystal of quabodepistat and 2,5-di­hydroxy­benzoic acid was obtained and the crystal structure was solved from microcrystal electron diffraction (MicroED) data.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.084 Å
• R factor = 0.160
• wR factor = 0.480
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level A
TYPE036_ALERT_1_A  _exptl_absorpt_coefficient_mu is not of type numb.

Author Response: The calculation of Mu is uncertain due to the ED experiment.

PLAT082_ALERT_2_A High R1 Value ..................................       0.23 Report

Author Response: The high R1 value is due to kinematical refinement without considering the strong dynamical effect in electron diffraction.

PLAT084_ALERT_3_A High wR2 Value (i.e. > 0.25) ...................       0.63 Report

Author Response: The high wR2 value is due to kinematical refinement without considering the strong dynamical effect in electron diffraction.

PLAT340_ALERT_3_A Low Bond Precision on  C-C Bonds ...............    0.08519 Ang.

Author Response: This is due to the low quality of the specimen. Merging of multiple data sets was implemented to improve bond precision and completeness.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5556

Author Response: The low crystallinity of the sample prevented data collection to higher values of sine(theta_max)/wavelength

PLAT149_ALERT_3_B s.u. on the   beta    Angle is Too Large .......       0.09 Degree

Author Response: This is due to the low quality of the specimen. Merging of multiple data sets was implemented to improve bond precision and completeness.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.149
PLAT020_ALERT_3_C The Value of Rint is Greater Than 0.12 .........      0.149 Report
PLAT148_ALERT_3_C s.u. on the      a    - Axis is (Too) Large ....      0.300 Ang.
PLAT148_ALERT_3_C s.u. on the      b    - Axis is (Too) Large ....     0.3000 Ang.
PLAT148_ALERT_3_C s.u. on the      c    - Axis is (Too) Large ....      0.300 Ang.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT260_ALERT_2_C Large Average Ueq of Residue Including      Cl31      0.118 Check
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O > 1.3 Ang) ...........        O12 Check
PLAT353_ALERT_3_C Long   N-H (N0.87,N1.01A)  N7       - H7       .       1.01 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C32      - C38      .       1.55 Ang.

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
RADNT01_ALERT_1_G  Extra text has been found in the _diffrn_radiation_type field.
            Radiation given as 200 keV electrons
            Radiation identified as electron
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         22 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         42 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          6 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.50 Report
PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ...        -14 Units
PLAT153_ALERT_1_G The s.u.'s on the Cell Axes   are Equal ..(Note)        0.3 Ang.
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          6 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          3 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          4 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT188_ALERT_3_G A Non-default SIMU Restraint Value has been used     0.0100 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used     0.0100 Report
PLAT191_ALERT_3_G A Non-default SADI Restraint Value has been used     0.0100 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H3       ..O42      .       2.70 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H9B      ..O22      .       2.92 Ang.
PLAT480_ALERT_4_G Long H...A H-Bond Reported H34      ..O42      .       2.65 Ang.
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        388 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.9 Low

   4 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  24 ALERT level G = General information/check it is not something unexpected

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
  15 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

5-{[(3R,4R)-1-(4-Chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy}-8-fluoro-3,4-dihydroquinolin-2(1H)-one–2,5-dihydroxybenzoic acid (1/1)

Crystal data

C21H20ClF3N2O4·C7H6O4	F(000) = 224
Mr = 610.96	Dx = 1.338 Mg m^−3
Monoclinic, P21	Electron radiation, λ = 0.0251 Å
a = 5.6 (3) Å	Cell parameters from 411 reflections
b = 9.6 (3) Å	θ = 0.1–0.8°
c = 28.2 (3) Å	µ = 0.000 mm^−1
β = 90.30 (9)°	T = 293 K
V = 1516 (109) Å^3	Thin platelets, colourless
Z = 2	1 × 0.2 × 0.2 mm

Data collection

Rigaku XtaLAB Synergy-ED diffractometer	2030 reflections with I > 2σ(I)
Radiation source: thermionic-emission electron gun	Rint = 0.149
Detector resolution: 10.0 pixels mm^-1	θmax = 0.8°, θmin = 0.1°
rotation scans	h = −6→6
8548 measured reflections	k = −10→10
4096 independent reflections	l = −31→31

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.2805P)^2 + 0.170P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.160	(Δ/σ)max = 0.001
wR(F^2) = 0.480	Δρmax = 0.15 e Å^−3
S = 1.08	Δρmin = −0.15 e Å^−3
4096 reflections	Extinction correction: 'SHELXL2018/3 (Sheldrick, 2015)', Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
348 parameters	Extinction coefficient: 368 (31)
537 restraints	Absolute structure: All f" are zero, so absolute structure could not be determined
Hydrogen site location: inferred from neighbouring sites

Special details

Geometry. 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.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.960 (3)	0.5589 (17)	0.7945 (6)	0.070 (5)
C11	0.804 (4)	0.6700 (17)	0.7886 (5)	0.068 (4)
C6	0.660 (3)	0.7121 (17)	0.8261 (6)	0.063 (4)
C5	0.673 (3)	0.6431 (19)	0.8694 (6)	0.072 (5)
C4	0.829 (3)	0.5320 (19)	0.8752 (5)	0.075 (5)
H4	0.837583	0.485853	0.904220	0.090*
C3	0.973 (3)	0.4899 (16)	0.8378 (6)	0.073 (5)
H3	1.077324	0.415597	0.841680	0.087*
C10	0.796 (5)	0.753 (2)	0.7416 (8)	0.069 (5)
H10A	0.957975	0.785032	0.735893	0.083*
H10B	0.759602	0.686397	0.716684	0.083*
C9	0.631 (5)	0.878 (3)	0.7338 (10)	0.075 (5)
H9A	0.528342	0.859999	0.706630	0.090*
H9B	0.726751	0.959210	0.726908	0.090*
C8	0.476 (5)	0.906 (3)	0.7778 (9)	0.068 (5)
N7	0.479 (5)	0.824 (2)	0.8206 (10)	0.067 (5)
H7	0.359249	0.842859	0.846624	0.080*
C32	0.785 (2)	0.0552 (14)	0.9171 (6)	0.053 (4)
C37	0.611 (3)	0.1500 (15)	0.9033 (5)	0.054 (4)
H37	0.608891	0.184541	0.872468	0.065*
C36	0.440 (2)	0.1933 (15)	0.9357 (6)	0.057 (5)
C35	0.443 (2)	0.1417 (17)	0.9818 (6)	0.059 (5)
H35	0.327933	0.170661	1.003412	0.071*
C34	0.617 (3)	0.0469 (18)	0.9955 (5)	0.064 (5)
H34	0.619200	0.012343	1.026363	0.076*
C33	0.789 (2)	0.0036 (15)	0.9632 (6)	0.059 (4)
O40	1.128 (4)	−0.085 (2)	0.8909 (11)	0.069 (6)
C15	1.307 (4)	0.340 (2)	0.7081 (11)	0.081 (5)
C38	0.975 (3)	0.005 (2)	0.8818 (8)	0.053 (4)
O42	0.251 (4)	0.291 (2)	0.9211 (10)	0.061 (6)
H42	0.156468	0.302044	0.943037	0.092*
C14	1.241 (6)	0.397 (3)	0.7565 (12)	0.082 (5)
H14A	1.151605	0.326933	0.773690	0.099*
H14B	1.386475	0.415660	0.774296	0.099*
O12	0.319 (5)	1.000 (2)	0.7774 (9)	0.075 (7)
O41	0.958 (4)	−0.099 (2)	0.9792 (11)	0.076 (7)
H41	1.043887	−0.121798	0.956939	0.114*
F13	0.511 (6)	0.688 (2)	0.9048 (10)	0.079 (7)
O1	1.104 (4)	0.520 (2)	0.7540 (12)	0.077 (5)
O39	0.968 (4)	0.071 (2)	0.8400 (11)	0.066 (5)
H39	1.072100	0.039139	0.822607	0.099*
C17	1.138 (5)	0.243 (2)	0.6290 (10)	0.090 (6)
H17A	1.232176	0.158593	0.628400	0.108*
H17B	0.988301	0.225125	0.612765	0.108*
O21	0.972 (5)	0.185 (3)	0.7110 (12)	0.098 (8)
H21	0.828359	0.200591	0.711408	0.148*
C20	1.438 (5)	0.447 (2)	0.6775 (10)	0.089 (6)
H20A	1.346328	0.532911	0.678027	0.106*
H20B	1.591213	0.466927	0.692442	0.106*
O22	1.469 (3)	0.224 (2)	0.7149 (14)	0.083 (7)
H22	1.401436	0.161832	0.729667	0.125*
C16	1.087 (4)	0.283 (2)	0.6810 (9)	0.083 (5)
H16	0.976517	0.361826	0.679004	0.100*
C23	1.265 (6)	0.344 (3)	0.5511 (9)	0.131 (7)
C28	1.434 (5)	0.264 (3)	0.5280 (10)	0.150 (8)
C27	1.440 (5)	0.261 (3)	0.4787 (10)	0.164 (9)
H27	1.553704	0.206657	0.463185	0.197*
C26	1.277 (6)	0.339 (4)	0.4525 (9)	0.170 (9)
C25	1.108 (5)	0.419 (3)	0.4756 (10)	0.162 (9)
H25	0.998639	0.471406	0.458099	0.194*
C24	1.102 (5)	0.422 (3)	0.5249 (10)	0.148 (8)
Cl31	1.268 (6)	0.322 (4)	0.3905 (9)	0.215 (12)
F29	0.929 (10)	0.501 (5)	0.548 (2)	0.172 (14)
F30	1.615 (9)	0.176 (5)	0.551 (2)	0.158 (13)
C19	1.485 (4)	0.410 (3)	0.6254 (10)	0.092 (6)
H19A	1.534890	0.492210	0.608241	0.111*
H19B	1.612402	0.341921	0.623696	0.111*
N18	1.268 (5)	0.353 (3)	0.6034 (11)	0.101 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.078 (9)	0.057 (8)	0.076 (10)	0.029 (7)	0.010 (9)	0.005 (8)
C11	0.085 (9)	0.056 (8)	0.062 (9)	0.030 (7)	0.008 (8)	0.011 (7)
C6	0.087 (9)	0.043 (7)	0.059 (9)	0.034 (7)	0.009 (8)	0.015 (7)
C5	0.088 (10)	0.063 (9)	0.066 (10)	0.037 (8)	0.007 (9)	0.024 (8)
C4	0.081 (11)	0.069 (10)	0.074 (11)	0.037 (8)	0.002 (10)	0.020 (9)
C3	0.082 (11)	0.059 (9)	0.076 (11)	0.032 (9)	0.002 (10)	0.008 (8)
C10	0.089 (10)	0.058 (9)	0.060 (10)	0.031 (8)	0.009 (10)	0.011 (8)
C9	0.096 (11)	0.067 (9)	0.062 (11)	0.040 (9)	0.015 (10)	0.018 (9)
C8	0.090 (10)	0.058 (8)	0.055 (10)	0.045 (8)	0.011 (9)	0.013 (8)
N7	0.096 (10)	0.045 (8)	0.059 (10)	0.040 (8)	0.015 (9)	0.009 (7)
C32	0.051 (7)	0.050 (7)	0.057 (9)	0.005 (6)	0.002 (7)	−0.002 (7)
C37	0.055 (8)	0.052 (8)	0.055 (10)	0.010 (7)	0.008 (8)	−0.004 (8)
C36	0.049 (8)	0.064 (9)	0.059 (10)	0.015 (7)	0.004 (8)	−0.004 (8)
C35	0.052 (9)	0.063 (9)	0.062 (10)	0.001 (7)	0.009 (9)	0.003 (9)
C34	0.064 (9)	0.063 (9)	0.064 (10)	0.000 (8)	0.004 (9)	0.012 (9)
C33	0.061 (8)	0.053 (8)	0.065 (10)	−0.004 (7)	0.006 (8)	0.009 (8)
O40	0.047 (10)	0.078 (12)	0.083 (17)	0.016 (9)	0.025 (12)	0.016 (12)
C15	0.062 (8)	0.062 (8)	0.118 (11)	0.038 (7)	0.019 (9)	0.020 (8)
C38	0.044 (8)	0.053 (9)	0.063 (10)	0.001 (7)	0.001 (8)	−0.008 (8)
O42	0.048 (10)	0.065 (11)	0.072 (16)	0.022 (8)	0.004 (12)	−0.005 (11)
C14	0.072 (10)	0.059 (9)	0.116 (12)	0.033 (9)	0.018 (10)	0.011 (9)
O12	0.106 (15)	0.062 (11)	0.058 (15)	0.059 (11)	0.015 (13)	0.020 (11)
O41	0.087 (14)	0.055 (10)	0.087 (17)	0.001 (9)	0.013 (14)	0.024 (12)
F13	0.134 (17)	0.045 (9)	0.059 (14)	0.041 (11)	0.023 (13)	0.025 (10)
O1	0.071 (9)	0.057 (8)	0.103 (12)	0.030 (8)	0.018 (10)	0.007 (9)
O39	0.046 (10)	0.084 (12)	0.069 (13)	0.001 (10)	0.000 (11)	0.005 (11)
C17	0.075 (10)	0.072 (10)	0.124 (13)	0.041 (9)	0.019 (11)	0.018 (10)
O21	0.068 (12)	0.092 (14)	0.14 (2)	0.016 (10)	0.013 (15)	0.031 (14)
C20	0.074 (10)	0.067 (9)	0.125 (13)	0.034 (8)	0.020 (11)	0.026 (10)
O22	0.049 (10)	0.057 (10)	0.14 (2)	0.036 (9)	0.027 (13)	0.012 (12)
C16	0.062 (9)	0.065 (9)	0.122 (12)	0.039 (8)	0.019 (10)	0.018 (9)
C23	0.123 (13)	0.128 (12)	0.143 (14)	0.041 (12)	0.019 (14)	0.012 (13)
C28	0.146 (15)	0.149 (15)	0.154 (16)	0.043 (14)	0.018 (16)	−0.007 (15)
C27	0.165 (16)	0.162 (16)	0.166 (18)	0.041 (15)	0.017 (18)	−0.011 (17)
C26	0.174 (16)	0.168 (16)	0.168 (17)	0.040 (15)	0.015 (18)	−0.007 (16)
C25	0.161 (16)	0.159 (16)	0.165 (18)	0.040 (15)	0.015 (18)	0.005 (17)
C24	0.144 (15)	0.146 (15)	0.153 (17)	0.045 (14)	0.018 (16)	0.012 (15)
Cl31	0.23 (2)	0.22 (2)	0.19 (2)	0.06 (2)	0.01 (2)	−0.01 (2)
F29	0.17 (3)	0.18 (3)	0.16 (3)	0.05 (2)	0.02 (3)	0.02 (2)
F30	0.16 (2)	0.14 (2)	0.17 (3)	0.05 (2)	0.01 (3)	−0.05 (2)
C19	0.078 (11)	0.072 (10)	0.127 (13)	0.041 (9)	0.025 (12)	0.030 (11)
N18	0.088 (10)	0.090 (10)	0.126 (12)	0.035 (9)	0.022 (11)	0.023 (10)

Geometric parameters (Å, º)

C2—C11	1.3900	C15—O22	1.45 (5)
C2—C3	1.3900	C15—C16	1.54 (6)
C2—O1	1.45 (4)	C38—O39	1.34 (4)
C11—C6	1.3900	O42—H42	0.8200
C11—C10	1.55 (2)	C14—H14A	0.9700
C6—C5	1.3900	C14—H14B	0.9700
C6—N7	1.49 (6)	C14—O1	1.41 (5)
C5—C4	1.3900	O41—H41	0.8200
C5—F13	1.42 (5)	O39—H39	0.8200
C4—H4	0.9300	C17—H17A	0.9700
C4—C3	1.3900	C17—H17B	0.9700
C3—H3	0.9300	C17—C16	1.54 (2)
C10—H10A	0.9700	C17—N18	1.47 (4)
C10—H10B	0.9700	O21—H21	0.8200
C10—C9	1.53 (5)	O21—C16	1.42 (3)
C9—H9A	0.9700	C20—H20A	0.9700
C9—H9B	0.9700	C20—H20B	0.9700
C9—C8	1.54 (4)	C20—C19	1.53 (2)
C8—N7	1.44 (4)	O22—H22	0.8200
C8—O12	1.26 (5)	C16—H16	0.9800
N7—H7	1.0100	C23—C28	1.3900
C32—C37	1.3900	C23—C24	1.3900
C32—C33	1.3900	C23—N18	1.47 (4)
C32—C38	1.53 (5)	C28—C27	1.3900
C37—H37	0.9300	C28—F30	1.46 (7)
C37—C36	1.3900	C27—H27	0.9300
C36—C35	1.3900	C27—C26	1.3900
C36—O42	1.47 (6)	C26—C25	1.3900
C35—H35	0.9300	C26—Cl31	1.75 (3)
C35—C34	1.3900	C25—H25	0.9300
C34—H34	0.9300	C25—C24	1.3900
C34—C33	1.3900	C24—F29	1.40 (7)
C33—O41	1.44 (5)	C19—H19A	0.9700
O40—C38	1.24 (5)	C19—H19B	0.9700
C15—C14	1.52 (4)	C19—N18	1.46 (6)
C15—C20	1.54 (4)
C11—C2—C3	120.0	O40—C38—C32	124 (3)
C11—C2—O1	117 (2)	O40—C38—O39	122 (2)
C3—C2—O1	123 (2)	O39—C38—C32	114 (2)
C2—C11—C10	120.8 (16)	C36—O42—H42	109.5
C6—C11—C2	120.0	C15—C14—H14A	108.9
C6—C11—C10	119.2 (19)	C15—C14—H14B	108.9
C11—C6—N7	122 (2)	H14A—C14—H14B	107.7
C5—C6—C11	120.0	O1—C14—C15	113 (3)
C5—C6—N7	117.9 (18)	O1—C14—H14A	108.9
C6—C5—C4	120.0	O1—C14—H14B	108.9
C6—C5—F13	116 (2)	C33—O41—H41	109.5
C4—C5—F13	124 (2)	C14—O1—C2	119 (3)
C5—C4—H4	120.0	C38—O39—H39	109.5
C3—C4—C5	120.0	H17A—C17—H17B	107.9
C3—C4—H4	120.0	C16—C17—H17A	109.1
C2—C3—H3	120.0	C16—C17—H17B	109.1
C4—C3—C2	120.0	N18—C17—H17A	109.1
C4—C3—H3	120.0	N18—C17—H17B	109.1
C11—C10—H10A	106.6	N18—C17—C16	112 (2)
C11—C10—H10B	106.6	C16—O21—H21	109.5
H10A—C10—H10B	106.6	C15—C20—H20A	107.9
C9—C10—C11	123 (2)	C15—C20—H20B	107.9
C9—C10—H10A	106.6	H20A—C20—H20B	107.2
C9—C10—H10B	106.6	C19—C20—C15	117 (2)
C10—C9—H9A	109.3	C19—C20—H20A	107.9
C10—C9—H9B	109.3	C19—C20—H20B	107.9
C10—C9—C8	111 (3)	C15—O22—H22	109.5
H9A—C9—H9B	108.0	C15—C16—H16	105.0
C8—C9—H9A	109.3	C17—C16—C15	114 (3)
C8—C9—H9B	109.3	C17—C16—H16	105.0
N7—C8—C9	125 (2)	O21—C16—C15	107 (3)
O12—C8—C9	121 (3)	O21—C16—C17	119 (3)
O12—C8—N7	114 (3)	O21—C16—H16	105.0
C6—N7—H7	120.4	C28—C23—C24	120.0
C8—N7—C6	119 (3)	C28—C23—N18	120 (2)
C8—N7—H7	120.4	C24—C23—N18	120 (2)
C37—C32—C33	120.0	C23—C28—C27	120.0
C37—C32—C38	121 (2)	C23—C28—F30	126 (3)
C33—C32—C38	119.1 (19)	C27—C28—F30	114 (3)
C32—C37—H37	120.0	C28—C27—H27	120.0
C36—C37—C32	120.0	C26—C27—C28	120.0
C36—C37—H37	120.0	C26—C27—H27	120.0
C37—C36—C35	120.0	C27—C26—Cl31	119.7 (11)
C37—C36—O42	120 (3)	C25—C26—C27	120.0
C35—C36—O42	119.6 (18)	C25—C26—Cl31	120.1 (13)
C36—C35—H35	120.0	C26—C25—H25	120.0
C34—C35—C36	120.0	C26—C25—C24	120.0
C34—C35—H35	120.0	C24—C25—H25	120.0
C35—C34—H34	120.0	C23—C24—F29	120 (4)
C35—C34—C33	120.0	C25—C24—C23	120.0
C33—C34—H34	120.0	C25—C24—F29	120 (3)
C32—C33—O41	122.8 (19)	C20—C19—H19A	109.6
C34—C33—C32	120.0	C20—C19—H19B	109.6
C34—C33—O41	117 (3)	H19A—C19—H19B	108.1
C14—C15—C20	112 (3)	N18—C19—C20	110 (3)
C14—C15—C16	112 (3)	N18—C19—H19A	109.6
C20—C15—C16	110 (3)	N18—C19—H19B	109.6
O22—C15—C14	109 (3)	C17—N18—C23	116 (3)
O22—C15—C20	107 (4)	C19—N18—C17	118 (3)
O22—C15—C16	107 (4)	C19—N18—C23	117 (3)
C2—C11—C6—C5	0.0	C14—C15—C16—C17	172 (2)
C2—C11—C6—N7	−176 (2)	C14—C15—C16—O21	−54 (3)
C2—C11—C10—C9	−179 (2)	O12—C8—N7—C6	−178 (2)
C11—C2—C3—C4	0.0	F13—C5—C4—C3	176 (2)
C11—C2—O1—C14	−172 (2)	O1—C2—C11—C6	179.7 (19)
C11—C6—C5—C4	0.0	O1—C2—C11—C10	−3 (2)
C11—C6—C5—F13	−177 (2)	O1—C2—C3—C4	−180 (2)
C11—C6—N7—C8	−10 (3)	C20—C15—C14—O1	56 (4)
C11—C10—C9—C8	−1 (4)	C20—C15—C16—C17	46 (3)
C6—C11—C10—C9	−2 (4)	C20—C15—C16—O21	−180 (2)
C6—C5—C4—C3	0.0	C20—C19—N18—C17	−48 (3)
C5—C6—N7—C8	174 (2)	C20—C19—N18—C23	165 (2)
C5—C4—C3—C2	0.0	O22—C15—C14—O1	174 (2)
C3—C2—C11—C6	0.0	O22—C15—C20—C19	69 (3)
C3—C2—C11—C10	177 (2)	O22—C15—C16—C17	−70 (3)
C3—C2—O1—C14	8 (3)	O22—C15—C16—O21	65 (3)
C10—C11—C6—C5	−177 (2)	C16—C15—C14—O1	−69 (4)
C10—C11—C6—N7	7 (2)	C16—C15—C20—C19	−46 (3)
C10—C9—C8—N7	−2 (4)	C16—C17—N18—C23	−163 (3)
C10—C9—C8—O12	−176 (3)	C16—C17—N18—C19	51 (4)
C9—C8—N7—C6	7 (5)	C23—C28—C27—C26	0.0
N7—C6—C5—C4	176 (2)	C28—C23—C24—C25	0.0
N7—C6—C5—F13	−1 (2)	C28—C23—C24—F29	178.7 (11)
C32—C37—C36—C35	0.0	C28—C23—N18—C17	−86 (5)
C32—C37—C36—O42	−178.6 (16)	C28—C23—N18—C19	61 (5)
C37—C32—C33—C34	0.0	C28—C27—C26—C25	0.0
C37—C32—C33—O41	177.5 (17)	C28—C27—C26—Cl31	−174 (3)
C37—C32—C38—O40	−175.6 (19)	C27—C26—C25—C24	0.0
C37—C32—C38—O39	6 (2)	C26—C25—C24—C23	0.0
C37—C36—C35—C34	0.0	C26—C25—C24—F29	−178.7 (11)
C36—C35—C34—C33	0.0	C24—C23—C28—C27	0.0
C35—C34—C33—C32	0.0	C24—C23—C28—F30	−179 (3)
C35—C34—C33—O41	−177.7 (17)	C24—C23—N18—C17	97 (5)
C33—C32—C37—C36	0.0	C24—C23—N18—C19	−116 (4)
C33—C32—C38—O40	4 (3)	Cl31—C26—C25—C24	174 (3)
C33—C32—C38—O39	−174.3 (16)	F30—C28—C27—C26	179 (3)
C15—C14—O1—C2	159 (2)	N18—C17—C16—C15	−49 (3)
C15—C20—C19—N18	47 (3)	N18—C17—C16—O21	−177 (2)
C38—C32—C37—C36	179.5 (14)	N18—C23—C28—C27	−177 (3)
C38—C32—C33—C34	−179.5 (14)	N18—C23—C28—F30	4 (3)
C38—C32—C33—O41	−2 (2)	N18—C23—C24—C25	177 (3)
O42—C36—C35—C34	178.6 (16)	N18—C23—C24—F29	−5 (3)
C14—C15—C20—C19	−172 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O42^i	0.93	2.71	3.40 (7)	131
C9—H9B···O22^ii	0.97	2.94	3.49 (11)	117
N7—H7···O40^ii	1.01	1.93	2.93 (9)	169
C34—H34···O42^iii	0.93	2.69	3.48 (7)	143
O42—H42···O41^iv	0.82	2.48	3.23 (6)	152
O39—H39···O12^v	0.82	1.92	2.73 (10)	169
O21—H21···O22^vi	0.82	2.02	2.84 (18)	175
O22—H22···O12^v	0.82	2.11	2.90 (7)	164

Symmetry codes: (i) x+1, y, z; (ii) x−1, y+1, z; (iii) −x+1, y−1/2, −z+2; (iv) −x+1, y+1/2, −z+2; (v) x+1, y−1, z; (vi) x−1, y, z.