Diethyl 4-(4-chloro-2-propyl-1H-imidazol-5-yl)-2,6-dimethyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate monohydrate

In the title hydrate, C₁₉H₂₆ClN₃O₄·H₂O, the imidazole ring is nearly perpendicular [dihedral angle = 89.5 (1)°] to the di­hydro­pyridine moiety. The propyl and one of the ethyl groups are disordered over two resolved sets of sites [occupancy factors 0.524 (8):0.476 (8) and 0.640 (16):0.360 (16), respectively]. In the crystal, a three-dimensional network is constructed by O—H...O, N—H...O and N—H...N hydrogen bonds involving both the main mol­ecule and the water mol­ecule of crystallization, as well as C—H...π(ring) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.065
• wR factor = 0.182
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.73 Report
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.8 Ratio
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.9 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference C18      --C19      .       0.17 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00591 Ang.

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         12 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          4 Report
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          5 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          2 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        19% Note
PLAT791_ALERT_4_G Model has Chirality at C3          (Chiral SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         43 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012; software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Diethyl 4-(4-chloro-2-propyl-1H-imidazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate monohydrate

Crystal data

C19H26ClN3O4·H2O	Dx = 1.184 Mg m^−3
Mr = 413.89	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 7831 reflections
a = 8.5308 (11) Å	θ = 2.4–25.3°
c = 31.893 (4) Å	µ = 0.20 mm^−1
V = 2321.0 (7) Å^3	T = 200 K
Z = 4	Block, colourless
F(000) = 880	0.34 × 0.29 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer	5536 independent reflections
Radiation source: fine-focus sealed tube	4641 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.0°, θmin = 2.4°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −11→11
Tmin = 0.48, Tmax = 0.96	l = −41→41
21675 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.182	w = 1/[σ^2(Fo^2) + (0.1247P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
5536 reflections	Δρmax = 0.82 e Å^−3
277 parameters	Δρmin = −0.22 e Å^−3
43 restraints	Absolute structure: Flack x determined using 1897 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (4)

Special details

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to nitrogen and oxygen were placed in locations derived from a difference map and their coordinates adjusted to give N—H = 0.91 %A and O—H = 0.87 Å. All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The propyl substituent and the ethyl group of one of the ester substituents are each disordered over two sites. The components of the disorder were refined with restraints that the geometries be comparable.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.46749 (12)	0.49418 (16)	0.54263 (4)	0.0528 (3)
O1	0.9755 (5)	0.8067 (4)	0.47266 (13)	0.0582 (9)
O2	0.7765 (4)	0.7394 (4)	0.51427 (12)	0.0486 (8)
O3	0.9671 (5)	0.1161 (4)	0.59772 (11)	0.0586 (10)
O4	0.7708 (4)	0.2888 (4)	0.59462 (11)	0.0540 (9)
N1	1.1423 (4)	0.3440 (4)	0.48885 (11)	0.0357 (7)
H1	1.245197	0.327894	0.482713	0.033 (11)*
N2	0.7297 (4)	0.2751 (4)	0.46475 (10)	0.0305 (6)
H2	0.817274	0.232166	0.453195	0.041 (13)*
N3	0.4772 (4)	0.3110 (4)	0.47461 (11)	0.0386 (7)
C1	1.0894 (4)	0.4920 (5)	0.47960 (12)	0.0350 (8)
C2	0.9557 (4)	0.5435 (4)	0.49772 (12)	0.0320 (7)
C3	0.8546 (4)	0.4339 (4)	0.52409 (11)	0.0286 (7)
H3	0.812065	0.495378	0.548243	0.034*
C4	0.9551 (4)	0.3013 (4)	0.54169 (12)	0.0306 (7)
C5	1.0896 (4)	0.2586 (5)	0.52216 (13)	0.0336 (8)
C6	1.1934 (6)	0.5810 (7)	0.44948 (18)	0.0532 (12)
H6A	1.262391	0.507243	0.434815	0.080*
H6B	1.257065	0.656739	0.465094	0.080*
H6C	1.128277	0.636602	0.429009	0.080*
C7	1.1910 (5)	0.1220 (6)	0.53262 (17)	0.0494 (11)
H7A	1.270799	0.108950	0.510796	0.074*
H7B	1.126603	0.027033	0.534251	0.074*
H7C	1.242248	0.140061	0.559687	0.074*
C8	0.9068 (5)	0.7067 (5)	0.49327 (13)	0.0380 (8)
C9	0.7276 (8)	0.9030 (6)	0.5138 (2)	0.0655 (15)
H9A	0.815436	0.971131	0.522711	0.079*
H9B	0.696083	0.933900	0.485068	0.079*
C10	0.5964 (10)	0.9206 (9)	0.5423 (4)	0.108 (3)
H10A	0.572799	1.032164	0.545959	0.162*
H10B	0.623239	0.874375	0.569507	0.162*
H10C	0.504424	0.867017	0.530726	0.162*
C11	0.9040 (5)	0.2247 (5)	0.57994 (12)	0.0365 (8)
C12	0.7170 (16)	0.2420 (14)	0.6360 (3)	0.061 (3)	0.640 (16)
H12A	0.655582	0.143916	0.633696	0.073*	0.640 (16)
H12B	0.808779	0.220946	0.654162	0.073*	0.640 (16)
C13	0.6218 (18)	0.3615 (18)	0.6548 (4)	0.093 (4)	0.640 (16)
H13A	0.683452	0.457725	0.657961	0.139*	0.640 (16)
H13B	0.586070	0.326148	0.682471	0.139*	0.640 (16)
H13C	0.530725	0.382297	0.636939	0.139*	0.640 (16)
C12A	0.705 (3)	0.201 (3)	0.6295 (6)	0.061 (3)	0.360 (16)
H12C	0.694499	0.088692	0.621944	0.073*	0.360 (16)
H12D	0.774495	0.208879	0.654368	0.073*	0.360 (16)
C13A	0.555 (3)	0.268 (4)	0.6382 (7)	0.093 (4)	0.360 (16)
H13D	0.568732	0.370181	0.651812	0.139*	0.360 (16)
H13E	0.496011	0.198304	0.656902	0.139*	0.360 (16)
H13F	0.496892	0.281704	0.611956	0.139*	0.360 (16)
C14	0.7186 (4)	0.3699 (4)	0.49976 (11)	0.0290 (7)
C15	0.5620 (4)	0.3880 (5)	0.50448 (12)	0.0343 (8)
C16	0.5849 (5)	0.2426 (5)	0.45107 (13)	0.0376 (8)
C17	0.5464 (12)	0.144 (5)	0.4135 (9)	0.0525 (14)	0.524 (8)
H17A	0.542924	0.032752	0.422055	0.063*	0.524 (8)
H17B	0.631123	0.155890	0.392517	0.063*	0.524 (8)
C18	0.3896 (12)	0.1877 (13)	0.3930 (3)	0.0576 (18)	0.524 (8)
H18A	0.396508	0.299632	0.384965	0.069*	0.524 (8)
H18B	0.308351	0.180172	0.415038	0.069*	0.524 (8)
C19	0.3234 (14)	0.0935 (19)	0.3523 (4)	0.088 (3)	0.524 (8)
H19A	0.222441	0.138200	0.343833	0.132*	0.524 (8)
H19B	0.398360	0.103007	0.329169	0.132*	0.524 (8)
H19C	0.309558	−0.017327	0.359461	0.132*	0.524 (8)
C17A	0.5500 (13)	0.149 (6)	0.4125 (10)	0.0525 (14)	0.476 (8)
H17C	0.636510	0.073361	0.407746	0.063*	0.476 (8)
H17D	0.545851	0.220029	0.388049	0.063*	0.476 (8)
C18A	0.3948 (12)	0.0580 (14)	0.4153 (3)	0.0576 (18)	0.476 (8)
H18C	0.312568	0.134258	0.423352	0.069*	0.476 (8)
H18D	0.404806	−0.016940	0.438878	0.069*	0.476 (8)
C19A	0.3291 (16)	−0.040 (2)	0.3751 (4)	0.088 (3)	0.476 (8)
H19D	0.229519	−0.089897	0.382512	0.132*	0.476 (8)
H19E	0.312735	0.032066	0.351558	0.132*	0.476 (8)
H19F	0.405573	−0.120117	0.367186	0.132*	0.476 (8)
O5	0.9682 (3)	0.0915 (4)	0.42764 (10)	0.0414 (7)
H5A	0.916316	0.082739	0.404279	0.062*
H5B	0.949174	0.004180	0.440755	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0337 (5)	0.0708 (8)	0.0539 (6)	0.0073 (5)	0.0067 (5)	−0.0214 (5)
O1	0.068 (2)	0.0387 (17)	0.068 (2)	−0.0017 (15)	0.0072 (18)	0.0179 (16)
O2	0.0483 (17)	0.0336 (15)	0.064 (2)	0.0106 (13)	0.0019 (15)	0.0027 (14)
O3	0.073 (2)	0.059 (2)	0.0445 (18)	0.0164 (17)	−0.0028 (17)	0.0197 (16)
O4	0.0550 (19)	0.065 (2)	0.0417 (16)	0.0101 (16)	0.0175 (14)	0.0228 (16)
N1	0.0216 (14)	0.0432 (18)	0.0423 (17)	0.0004 (12)	0.0020 (13)	0.0006 (15)
N2	0.0245 (14)	0.0345 (15)	0.0323 (15)	0.0002 (11)	0.0020 (12)	−0.0032 (13)
N3	0.0256 (15)	0.0485 (19)	0.0416 (18)	0.0006 (13)	−0.0002 (13)	−0.0068 (15)
C1	0.0257 (17)	0.044 (2)	0.0350 (18)	−0.0058 (15)	−0.0033 (14)	0.0028 (16)
C2	0.0308 (17)	0.0326 (18)	0.0327 (18)	−0.0008 (13)	−0.0038 (14)	0.0028 (15)
C3	0.0265 (16)	0.0313 (17)	0.0280 (16)	0.0023 (13)	0.0010 (13)	0.0010 (14)
C4	0.0282 (16)	0.0288 (16)	0.0347 (17)	−0.0003 (13)	−0.0062 (15)	0.0010 (15)
C5	0.0279 (17)	0.0344 (18)	0.0385 (19)	−0.0011 (14)	−0.0072 (15)	−0.0025 (16)
C6	0.035 (2)	0.063 (3)	0.061 (3)	−0.002 (2)	0.011 (2)	0.018 (2)
C7	0.034 (2)	0.050 (3)	0.064 (3)	0.0100 (19)	−0.001 (2)	0.004 (2)
C8	0.0398 (19)	0.037 (2)	0.0373 (19)	0.0001 (15)	−0.0086 (16)	0.0053 (17)
C9	0.076 (4)	0.037 (2)	0.083 (4)	0.013 (2)	−0.009 (3)	0.001 (3)
C10	0.095 (5)	0.056 (4)	0.172 (10)	0.034 (4)	0.028 (6)	−0.004 (5)
C11	0.041 (2)	0.0343 (19)	0.0347 (18)	−0.0018 (15)	−0.0027 (16)	0.0016 (16)
C12	0.077 (4)	0.063 (6)	0.043 (4)	−0.004 (4)	0.023 (3)	0.008 (4)
C13	0.100 (7)	0.112 (8)	0.066 (6)	0.028 (6)	0.048 (6)	0.019 (5)
C12A	0.077 (4)	0.063 (6)	0.043 (4)	−0.004 (4)	0.023 (3)	0.008 (4)
C13A	0.100 (7)	0.112 (8)	0.066 (6)	0.028 (6)	0.048 (6)	0.019 (5)
C14	0.0274 (16)	0.0283 (16)	0.0312 (17)	0.0043 (12)	0.0029 (14)	0.0016 (14)
C15	0.0273 (17)	0.040 (2)	0.035 (2)	0.0045 (15)	0.0018 (14)	−0.0036 (16)
C16	0.0307 (18)	0.042 (2)	0.040 (2)	0.0000 (15)	0.0000 (16)	−0.0017 (17)
C17	0.037 (2)	0.067 (3)	0.054 (3)	−0.002 (2)	−0.003 (2)	−0.021 (2)
C18	0.048 (4)	0.065 (4)	0.060 (4)	−0.006 (3)	−0.007 (3)	−0.015 (3)
C19	0.078 (5)	0.117 (8)	0.069 (5)	−0.008 (6)	0.043 (5)	−0.042 (5)
C17A	0.037 (2)	0.067 (3)	0.054 (3)	−0.002 (2)	−0.003 (2)	−0.021 (2)
C18A	0.048 (4)	0.065 (4)	0.060 (4)	−0.006 (3)	−0.007 (3)	−0.015 (3)
C19A	0.078 (5)	0.117 (8)	0.069 (5)	−0.008 (6)	0.043 (5)	−0.042 (5)
O5	0.0416 (16)	0.0426 (16)	0.0400 (16)	0.0000 (12)	−0.0005 (12)	−0.0037 (12)

Geometric parameters (Å, º)

Cl1—C15	1.718 (4)	C10—H10C	0.9800
O1—C8	1.226 (5)	C12—C13	1.436 (12)
O2—C8	1.328 (5)	C12—H12A	0.9900
O2—C9	1.456 (6)	C12—H12B	0.9900
O3—C11	1.212 (5)	C13—H13A	0.9800
O4—C11	1.346 (6)	C13—H13B	0.9800
O4—C12	1.453 (6)	C13—H13C	0.9800
O4—C12A	1.453 (7)	C12A—C13A	1.435 (12)
N1—C5	1.364 (5)	C12A—H12C	0.9900
N1—C1	1.373 (5)	C12A—H12D	0.9900
N1—H1	0.9100	C13A—H13D	0.9800
N2—C16	1.339 (5)	C13A—H13E	0.9800
N2—C14	1.382 (5)	C13A—H13F	0.9800
N2—H2	0.9100	C14—C15	1.354 (5)
N3—C16	1.323 (5)	C16—C17A	1.498 (7)
N3—C15	1.364 (5)	C16—C17	1.499 (7)
C1—C2	1.352 (5)	C17—C18	1.53 (2)
C1—C6	1.512 (6)	C17—H17A	0.9900
C2—C8	1.460 (5)	C17—H17B	0.9900
C2—C3	1.525 (5)	C18—C19	1.626 (13)
C3—C14	1.498 (5)	C18—H18A	0.9900
C3—C4	1.527 (5)	C18—H18B	0.9900
C3—H3	1.0000	C19—H19A	0.9800
C4—C5	1.356 (5)	C19—H19B	0.9800
C4—C11	1.451 (5)	C19—H19C	0.9800
C5—C7	1.489 (6)	C17A—C18A	1.54 (2)
C6—H6A	0.9800	C17A—H17C	0.9900
C6—H6B	0.9800	C17A—H17D	0.9900
C6—H6C	0.9800	C18A—C19A	1.629 (13)
C7—H7A	0.9800	C18A—H18C	0.9900
C7—H7B	0.9800	C18A—H18D	0.9900
C7—H7C	0.9800	C19A—H19D	0.9800
C9—C10	1.451 (12)	C19A—H19E	0.9800
C9—H9A	0.9900	C19A—H19F	0.9800
C9—H9B	0.9900	O5—H5A	0.8699
C10—H10A	0.9800	O5—H5B	0.8699
C10—H10B	0.9800
C8—O2—C9	115.8 (4)	C12—C13—H13B	109.5
C11—O4—C12	118.1 (5)	H13A—C13—H13B	109.5
C11—O4—C12A	112.3 (8)	C12—C13—H13C	109.5
C5—N1—C1	123.4 (3)	H13A—C13—H13C	109.5
C5—N1—H1	113.9	H13B—C13—H13C	109.5
C1—N1—H1	114.2	C13A—C12A—O4	106.5 (13)
C16—N2—C14	108.7 (3)	C13A—C12A—H12C	110.4
C16—N2—H2	122.8	O4—C12A—H12C	110.4
C14—N2—H2	128.2	C13A—C12A—H12D	110.4
C16—N3—C15	103.9 (3)	O4—C12A—H12D	110.4
C2—C1—N1	118.9 (3)	H12C—C12A—H12D	108.6
C2—C1—C6	127.1 (4)	C12A—C13A—H13D	109.5
N1—C1—C6	113.9 (4)	C12A—C13A—H13E	109.5
C1—C2—C8	120.6 (4)	H13D—C13A—H13E	109.5
C1—C2—C3	120.9 (3)	C12A—C13A—H13F	109.5
C8—C2—C3	118.5 (3)	H13D—C13A—H13F	109.5
C14—C3—C2	112.1 (3)	H13E—C13A—H13F	109.5
C14—C3—C4	110.8 (3)	C15—C14—N2	102.9 (3)
C2—C3—C4	109.8 (3)	C15—C14—C3	131.7 (3)
C14—C3—H3	108.0	N2—C14—C3	125.3 (3)
C2—C3—H3	108.0	C14—C15—N3	113.0 (3)
C4—C3—H3	108.0	C14—C15—Cl1	127.0 (3)
C5—C4—C11	121.3 (3)	N3—C15—Cl1	120.0 (3)
C5—C4—C3	120.3 (3)	N3—C16—N2	111.4 (4)
C11—C4—C3	118.3 (3)	N3—C16—C17A	124.3 (6)
C4—C5—N1	119.6 (3)	N2—C16—C17A	124.2 (5)
C4—C5—C7	126.8 (4)	N3—C16—C17	123.2 (5)
N1—C5—C7	113.6 (4)	N2—C16—C17	125.3 (5)
C1—C6—H6A	109.5	C16—C17—C18	113.4 (15)
C1—C6—H6B	109.5	C16—C17—H17A	108.9
H6A—C6—H6B	109.5	C18—C17—H17A	108.9
C1—C6—H6C	109.5	C16—C17—H17B	108.9
H6A—C6—H6C	109.5	C18—C17—H17B	108.9
H6B—C6—H6C	109.5	H17A—C17—H17B	107.7
C5—C7—H7A	109.5	C17—C18—C19	121.6 (9)
C5—C7—H7B	109.5	C17—C18—H18A	106.9
H7A—C7—H7B	109.5	C19—C18—H18A	106.9
C5—C7—H7C	109.5	C17—C18—H18B	106.9
H7A—C7—H7C	109.5	C19—C18—H18B	106.9
H7B—C7—H7C	109.5	H18A—C18—H18B	106.7
O1—C8—O2	121.6 (4)	C18—C19—H19A	109.5
O1—C8—C2	125.4 (4)	C18—C19—H19B	109.5
O2—C8—C2	113.0 (3)	H19A—C19—H19B	109.5
C10—C9—O2	108.2 (5)	C18—C19—H19C	109.5
C10—C9—H9A	110.1	H19A—C19—H19C	109.5
O2—C9—H9A	110.1	H19B—C19—H19C	109.5
C10—C9—H9B	110.1	C16—C17A—C18A	113.1 (16)
O2—C9—H9B	110.1	C16—C17A—H17C	109.0
H9A—C9—H9B	108.4	C18A—C17A—H17C	109.0
C9—C10—H10A	109.5	C16—C17A—H17D	109.0
C9—C10—H10B	109.5	C18A—C17A—H17D	109.0
H10A—C10—H10B	109.5	H17C—C17A—H17D	107.8
C9—C10—H10C	109.5	C17A—C18A—C19A	120.5 (9)
H10A—C10—H10C	109.5	C17A—C18A—H18C	107.2
H10B—C10—H10C	109.5	C19A—C18A—H18C	107.2
O3—C11—O4	121.5 (4)	C17A—C18A—H18D	107.2
O3—C11—C4	127.2 (4)	C19A—C18A—H18D	107.2
O4—C11—C4	111.3 (3)	H18C—C18A—H18D	106.8
C13—C12—O4	111.3 (8)	C18A—C19A—H19D	109.5
C13—C12—H12A	109.4	C18A—C19A—H19E	109.5
O4—C12—H12A	109.4	H19D—C19A—H19E	109.5
C13—C12—H12B	109.4	C18A—C19A—H19F	109.5
O4—C12—H12B	109.4	H19D—C19A—H19F	109.5
H12A—C12—H12B	108.0	H19E—C19A—H19F	109.5
C12—C13—H13A	109.5	H5A—O5—H5B	104.1
C5—N1—C1—C2	−15.6 (6)	C5—C4—C11—O3	−2.5 (6)
C5—N1—C1—C6	163.8 (4)	C3—C4—C11—O3	178.4 (4)
N1—C1—C2—C8	171.6 (3)	C5—C4—C11—O4	178.0 (4)
C6—C1—C2—C8	−7.7 (6)	C3—C4—C11—O4	−1.1 (5)
N1—C1—C2—C3	−6.9 (5)	C11—O4—C12—C13	154.4 (11)
C6—C1—C2—C3	173.8 (4)	C11—O4—C12A—C13A	−172.3 (18)
C1—C2—C3—C14	−98.7 (4)	C16—N2—C14—C15	−0.2 (4)
C8—C2—C3—C14	82.7 (4)	C16—N2—C14—C3	−179.2 (4)
C1—C2—C3—C4	24.9 (5)	C2—C3—C14—C15	−115.7 (4)
C8—C2—C3—C4	−153.6 (3)	C4—C3—C14—C15	121.2 (4)
C14—C3—C4—C5	100.0 (4)	C2—C3—C14—N2	63.0 (5)
C2—C3—C4—C5	−24.4 (5)	C4—C3—C14—N2	−60.1 (4)
C14—C3—C4—C11	−80.9 (4)	N2—C14—C15—N3	−0.2 (4)
C2—C3—C4—C11	154.7 (3)	C3—C14—C15—N3	178.7 (4)
C11—C4—C5—N1	−173.1 (3)	N2—C14—C15—Cl1	−180.0 (3)
C3—C4—C5—N1	5.9 (5)	C3—C14—C15—Cl1	−1.0 (6)
C11—C4—C5—C7	7.9 (6)	C16—N3—C15—C14	0.5 (5)
C3—C4—C5—C7	−173.0 (4)	C16—N3—C15—Cl1	−179.7 (3)
C1—N1—C5—C4	16.1 (6)	C15—N3—C16—N2	−0.6 (5)
C1—N1—C5—C7	−164.8 (4)	C15—N3—C16—C17A	−177 (3)
C9—O2—C8—O1	−4.4 (7)	C15—N3—C16—C17	−180 (2)
C9—O2—C8—C2	175.5 (4)	C14—N2—C16—N3	0.5 (5)
C1—C2—C8—O1	2.4 (6)	C14—N2—C16—C17A	177 (3)
C3—C2—C8—O1	−179.0 (4)	C14—N2—C16—C17	179 (2)
C1—C2—C8—O2	−177.6 (4)	N3—C16—C17—C18	26 (4)
C3—C2—C8—O2	1.0 (5)	N2—C16—C17—C18	−152.4 (14)
C8—O2—C9—C10	−172.8 (6)	C16—C17—C18—C19	−178.8 (18)
C12—O4—C11—O3	9.8 (9)	N3—C16—C17A—C18A	−34 (4)
C12A—O4—C11—O3	−7.5 (15)	N2—C16—C17A—C18A	150.1 (16)
C12—O4—C11—C4	−170.7 (7)	C16—C17A—C18A—C19A	175 (2)
C12A—O4—C11—C4	172.0 (14)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the N2/N3/C14–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3^i	0.91	2.00	2.906 (4)	173
N2—H2···O5	0.91	1.94	2.827 (4)	165
O5—H5A···O3^ii	0.87	2.07	2.853 (4)	149
O5—H5B···O1^iii	0.87	1.98	2.823 (5)	163
C13—H13B···Cg1^iv	0.98	2.78	3.518 (14)	133

Symmetry codes: (i) x+1, y, z; (ii) −y+1, x−1, z−1/4; (iii) x, y−1, z; (iv) y, −x+1, z+1/4.