Strychninium (S)-2-(2-bromo­phen­oxy)propanoate 1.4-hydrate

In the title mol­ecular salt, C₂₁H₂₃N₂O₂⁺·C₉H₈BrO₃⁻·1.4H₂O, the components are linked by inter­molecular C—O⁻...H—⁺N and OW—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.032
• wR factor = 0.066
• Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT245_ALERT_2_C U(iso) HO6A    Smaller than U(eq) O6      by ...       0.01 AngSq
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      20.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O4      ..       3.21 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C9 H8 Br O3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           30.55
           From the CIF: _reflns_number_total               4414
           Count of symmetry unique reflns         4417
           Completeness (_total/calc)             99.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2002) and XPREP (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Barbour, 2001).

Strychninium (S)-2-(2-bromophenoxy)propanoate 1.4-hydrate

Crystal data

C21H23N2O2^+·C9H8BrO3^−·1.4H2O	F(000) = 628
Mr = 604.69	Dx = 1.493 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5839 reflections
a = 11.8967 (7) Å	θ = 2.7–30.4°
b = 7.3825 (4) Å	µ = 1.58 mm^−1
c = 15.6221 (9) Å	T = 173 K
β = 101.359 (3)°	Transparent blade, colorless
V = 1345.17 (13) Å^3	0.24 × 0.11 × 0.04 mm
Z = 2

Data collection

Bruker Kappa APEXII diffractometer	3668 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.088
Graphite monochromator	θmax = 30.6°, θmin = 1.3°
φ and ω scans	h = −14→17
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −10→10
Tmin = 0.685, Tmax = 0.945	l = −22→22
25259 measured reflections	462 standard reflections every variable min
4414 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.0275P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.002
4414 reflections	Δρmax = 0.71 e Å^−3
383 parameters	Δρmin = −0.39 e Å^−3
4 restraints	Absolute structure: Flack (1983), with how many Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.011 (5)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	−0.46615 (2)	0.53052 (6)	0.709769 (17)	0.02380 (8)
O1	−0.19268 (17)	0.9513 (3)	0.90491 (13)	0.0202 (4)
O2	−0.23560 (19)	1.2441 (3)	0.90548 (15)	0.0324 (5)
O3	−0.40227 (15)	0.8795 (3)	0.80200 (11)	0.0155 (4)
C1	−0.2619 (2)	1.0828 (4)	0.89128 (17)	0.0179 (6)
C2	−0.38875 (19)	1.0413 (5)	0.85434 (14)	0.0165 (5)
H2	−0.4239	1.1458	0.8179	0.020*
C3	−0.4545 (2)	1.0081 (6)	0.92692 (16)	0.0222 (7)
H3A	−0.5365	0.9969	0.9018	0.033*
H3B	−0.4423	1.1099	0.9680	0.033*
H3C	−0.4272	0.8961	0.9578	0.033*
C4	−0.3785 (2)	0.8908 (4)	0.71997 (16)	0.0148 (5)
C5	−0.4041 (2)	0.7401 (4)	0.66643 (18)	0.0171 (5)
C6	−0.3907 (3)	0.7427 (5)	0.58042 (18)	0.0256 (7)
H6	−0.4090	0.6388	0.5445	0.031*
C7	−0.3502 (3)	0.8987 (5)	0.54728 (19)	0.0279 (7)
H7	−0.3415	0.9021	0.4881	0.034*
C8	−0.3225 (2)	1.0487 (6)	0.59967 (16)	0.0230 (6)
H8	−0.2946	1.1549	0.5765	0.028*
C9	−0.3353 (2)	1.0453 (5)	0.68658 (15)	0.0172 (5)
H9	−0.3145	1.1480	0.7229	0.021*
O4	0.36068 (15)	1.2665 (3)	0.78302 (11)	0.0145 (4)
O5	0.30624 (16)	0.8435 (3)	0.55671 (12)	0.0213 (4)
N1	0.21259 (19)	0.8537 (3)	0.67104 (14)	0.0134 (4)
N2	0.01014 (17)	1.0563 (3)	0.87615 (13)	0.0125 (5)
C10	−0.02125 (18)	1.0236 (6)	0.77682 (13)	0.0123 (4)
H10	−0.0986	0.9655	0.7627	0.015*
C11	−0.0259 (2)	1.2007 (4)	0.72808 (17)	0.0130 (5)
H11A	−0.0818	1.2832	0.7471	0.016*
H11B	−0.0506	1.1792	0.6646	0.016*
C12	0.0938 (2)	1.2861 (3)	0.74709 (16)	0.0116 (5)
H12	0.0896	1.4096	0.7204	0.014*
C13	0.1700 (2)	1.1645 (4)	0.70230 (16)	0.0113 (5)
H13	0.1296	1.1537	0.6400	0.014*
C14	0.1796 (2)	0.9733 (3)	0.73841 (16)	0.0099 (5)
H14	0.2409	0.9694	0.7923	0.012*
C15	0.1188 (2)	0.7411 (4)	0.63509 (16)	0.0136 (5)
C16	0.1098 (3)	0.6196 (4)	0.56600 (17)	0.0198 (6)
H16	0.1720	0.5987	0.5373	0.024*
C17	0.0057 (2)	0.5301 (6)	0.54083 (14)	0.0229 (5)
H17	−0.0031	0.4466	0.4937	0.027*
C18	−0.0853 (2)	0.5585 (4)	0.58189 (17)	0.0218 (7)
H18	−0.1560	0.4980	0.5617	0.026*
C19	−0.0737 (2)	0.6766 (4)	0.65336 (18)	0.0191 (6)
H19	−0.1353	0.6946	0.6830	0.023*
C20	0.0297 (2)	0.7666 (4)	0.67982 (17)	0.0148 (5)
C21	0.0689 (2)	0.8863 (3)	0.75823 (16)	0.0114 (5)
C22	0.0930 (2)	0.7762 (4)	0.84397 (18)	0.0143 (6)
H22A	0.0302	0.6893	0.8462	0.017*
H22B	0.1661	0.7089	0.8502	0.017*
C23	0.0997 (2)	0.9191 (4)	0.91412 (17)	0.0154 (5)
H23A	0.0827	0.8663	0.9684	0.018*
H23B	0.1768	0.9751	0.9272	0.018*
C24	0.0494 (2)	1.2461 (4)	0.89947 (17)	0.0141 (5)
H24A	0.0854	1.2524	0.9622	0.017*
H24B	−0.0173	1.3292	0.8889	0.017*
C25	0.1342 (2)	1.3028 (4)	0.84513 (18)	0.0124 (5)
C26	0.2379 (2)	1.3622 (4)	0.88170 (17)	0.0157 (5)
H26	0.2577	1.3697	0.9435	0.019*
C27	0.3254 (2)	1.4181 (4)	0.82904 (17)	0.0171 (5)
H27A	0.2923	1.5128	0.7866	0.021*
H27B	0.3931	1.4703	0.8684	0.021*
C28	0.2915 (2)	1.2310 (4)	0.69959 (16)	0.0133 (5)
H28	0.2873	1.3416	0.6622	0.016*
C29	0.3575 (2)	1.0804 (4)	0.66228 (18)	0.0190 (6)
H29A	0.3942	1.1349	0.6168	0.023*
H29B	0.4197	1.0378	0.7097	0.023*
C30	0.2906 (2)	0.9174 (4)	0.62330 (17)	0.0156 (5)
HN2	−0.057 (3)	1.022 (7)	0.8969 (19)	0.035 (8)*
O6	−0.1572 (2)	1.5896 (5)	0.8618 (2)	0.0475 (8)
HO6A	−0.193 (4)	1.518 (7)	0.874 (3)	0.037 (12)*
HO6B	−0.183 (4)	1.685 (8)	0.871 (3)	0.063 (16)*
O7	−0.3810 (5)	1.5420 (13)	0.9383 (3)	0.0339 (12)	0.40
HO7A	−0.391 (13)	1.443 (8)	0.908 (6)	0.09 (5)*	0.40
HO7B	−0.370 (8)	1.611 (11)	0.895 (4)	0.03 (3)*	0.40

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02710 (14)	0.01898 (12)	0.02584 (13)	−0.00937 (15)	0.00648 (10)	−0.00004 (16)
O1	0.0118 (10)	0.0263 (11)	0.0222 (10)	−0.0007 (8)	0.0031 (8)	0.0030 (8)
O2	0.0254 (12)	0.0228 (12)	0.0437 (14)	−0.0052 (10)	−0.0060 (10)	−0.0033 (11)
O3	0.0155 (9)	0.0179 (10)	0.0128 (8)	−0.0035 (8)	0.0023 (7)	0.0008 (7)
C1	0.0163 (13)	0.0251 (16)	0.0122 (12)	−0.0024 (11)	0.0028 (10)	0.0012 (10)
C2	0.0142 (11)	0.0197 (13)	0.0143 (10)	−0.0034 (14)	−0.0007 (8)	−0.0035 (15)
C3	0.0144 (12)	0.034 (2)	0.0175 (12)	0.0013 (14)	0.0026 (9)	−0.0019 (14)
C4	0.0102 (12)	0.0198 (14)	0.0141 (12)	0.0025 (10)	0.0016 (9)	0.0035 (10)
C5	0.0121 (12)	0.0187 (13)	0.0202 (13)	−0.0047 (11)	0.0024 (10)	0.0020 (11)
C6	0.0244 (15)	0.0339 (17)	0.0189 (14)	−0.0066 (14)	0.0055 (12)	−0.0061 (13)
C7	0.0298 (17)	0.0399 (19)	0.0150 (13)	−0.0079 (15)	0.0065 (12)	0.0013 (13)
C8	0.0191 (12)	0.0285 (18)	0.0221 (12)	−0.0044 (15)	0.0056 (9)	0.0045 (15)
C9	0.0146 (11)	0.0182 (14)	0.0180 (11)	−0.0030 (13)	0.0011 (8)	0.0049 (14)
O4	0.0120 (9)	0.0182 (10)	0.0129 (8)	−0.0001 (7)	0.0011 (7)	−0.0013 (7)
O5	0.0215 (10)	0.0278 (11)	0.0151 (9)	0.0035 (9)	0.0049 (8)	−0.0046 (9)
N1	0.0136 (11)	0.0120 (11)	0.0149 (11)	0.0030 (9)	0.0036 (9)	−0.0033 (9)
N2	0.0092 (9)	0.0146 (14)	0.0139 (9)	0.0011 (9)	0.0025 (7)	0.0020 (9)
C10	0.0110 (10)	0.0143 (11)	0.0110 (10)	−0.0006 (14)	0.0007 (7)	0.0015 (14)
C11	0.0103 (12)	0.0115 (12)	0.0162 (12)	0.0017 (9)	0.0001 (9)	0.0010 (9)
C12	0.0115 (12)	0.0091 (12)	0.0139 (12)	−0.0003 (10)	0.0018 (9)	0.0007 (9)
C13	0.0118 (12)	0.0105 (12)	0.0104 (12)	−0.0023 (10)	−0.0005 (9)	−0.0011 (10)
C14	0.0097 (11)	0.0078 (11)	0.0113 (11)	0.0016 (9)	0.0005 (9)	−0.0031 (9)
C15	0.0172 (13)	0.0109 (12)	0.0108 (11)	0.0016 (10)	−0.0017 (9)	0.0016 (10)
C16	0.0303 (16)	0.0143 (13)	0.0133 (12)	0.0042 (12)	0.0008 (11)	0.0000 (11)
C17	0.0399 (15)	0.0127 (10)	0.0121 (10)	−0.0055 (19)	−0.0044 (10)	0.0001 (16)
C18	0.0266 (14)	0.0127 (18)	0.0202 (12)	−0.0044 (11)	−0.0100 (10)	0.0012 (11)
C19	0.0190 (14)	0.0142 (13)	0.0219 (14)	0.0011 (11)	−0.0014 (11)	0.0036 (11)
C20	0.0182 (13)	0.0102 (12)	0.0139 (12)	0.0018 (10)	−0.0025 (10)	0.0014 (10)
C21	0.0130 (12)	0.0095 (12)	0.0107 (11)	0.0002 (10)	−0.0001 (9)	0.0010 (9)
C22	0.0152 (14)	0.0103 (13)	0.0162 (13)	0.0024 (11)	0.0000 (11)	0.0055 (10)
C23	0.0143 (12)	0.0160 (13)	0.0152 (12)	0.0013 (10)	0.0011 (10)	0.0025 (10)
C24	0.0157 (13)	0.0123 (12)	0.0150 (12)	0.0004 (10)	0.0048 (10)	−0.0017 (10)
C25	0.0140 (13)	0.0097 (12)	0.0138 (13)	0.0013 (10)	0.0034 (10)	0.0009 (10)
C26	0.0172 (13)	0.0143 (12)	0.0159 (12)	−0.0001 (11)	0.0036 (10)	−0.0044 (10)
C27	0.0153 (13)	0.0158 (13)	0.0200 (13)	−0.0066 (11)	0.0029 (10)	−0.0043 (11)
C28	0.0112 (12)	0.0166 (13)	0.0125 (12)	−0.0021 (10)	0.0036 (9)	0.0016 (10)
C29	0.0163 (13)	0.0214 (16)	0.0210 (13)	0.0002 (10)	0.0083 (10)	−0.0044 (10)
C30	0.0148 (13)	0.0163 (13)	0.0146 (12)	0.0059 (10)	0.0003 (10)	−0.0002 (10)
O6	0.0276 (15)	0.0218 (14)	0.093 (2)	−0.0004 (12)	0.0108 (15)	0.0067 (15)
O7	0.038 (3)	0.038 (4)	0.029 (3)	0.003 (4)	0.015 (2)	0.004 (4)

Geometric parameters (Å, º)

Br1—C5	1.896 (3)	C13—C14	1.516 (4)
O1—C1	1.263 (3)	C13—C28	1.535 (3)
O2—C1	1.240 (4)	C13—H13	1.0000
O3—C4	1.368 (3)	C14—C21	1.550 (3)
O3—C2	1.438 (4)	C14—H14	1.0000
C1—C2	1.537 (4)	C15—C16	1.391 (4)
C2—C3	1.519 (3)	C15—C20	1.392 (4)
C2—H2	1.0000	C16—C17	1.391 (4)
C3—H3A	0.9800	C16—H16	0.9500
C3—H3B	0.9800	C17—C18	1.378 (4)
C3—H3C	0.9800	C17—H17	0.9500
C4—C5	1.389 (4)	C18—C19	1.402 (4)
C4—C9	1.394 (4)	C18—H18	0.9500
C5—C6	1.384 (4)	C19—C20	1.388 (4)
C6—C7	1.387 (5)	C19—H19	0.9500
C6—H6	0.9500	C20—C21	1.508 (4)
C7—C8	1.378 (5)	C21—C22	1.545 (4)
C7—H7	0.9500	C22—C23	1.512 (4)
C8—C9	1.396 (3)	C22—H22A	0.9900
C8—H8	0.9500	C22—H22B	0.9900
C9—H9	0.9500	C23—H23A	0.9900
O4—C28	1.422 (3)	C23—H23B	0.9900
O4—C27	1.437 (3)	C24—C25	1.501 (4)
O5—C30	1.221 (3)	C24—H24A	0.9900
N1—C30	1.382 (3)	C24—H24B	0.9900
N1—C15	1.416 (3)	C25—C26	1.327 (4)
N1—C14	1.484 (3)	C26—C27	1.506 (4)
N2—C24	1.499 (4)	C26—H26	0.9500
N2—C23	1.504 (3)	C27—H27A	0.9900
N2—C10	1.542 (3)	C27—H27B	0.9900
N2—HN2	0.95 (3)	C28—C29	1.540 (4)
C10—C11	1.508 (5)	C28—H28	1.0000
C10—C21	1.544 (4)	C29—C30	1.503 (4)
C10—H10	1.0000	C29—H29A	0.9900
C11—C12	1.531 (3)	C29—H29B	0.9900
C11—H11A	0.9900	O6—HO6A	0.74 (5)
C11—H11B	0.9900	O6—HO6B	0.79 (6)
C12—C25	1.517 (4)	O7—HO7A	0.87 (2)
C12—C13	1.539 (3)	O7—HO7B	0.87 (2)
C12—H12	1.0000
C4—O3—C2	117.5 (2)	C20—C15—N1	109.9 (2)
O2—C1—O1	125.1 (3)	C17—C16—C15	117.0 (3)
O2—C1—C2	116.9 (3)	C17—C16—H16	121.5
O1—C1—C2	118.0 (3)	C15—C16—H16	121.5
O3—C2—C3	105.9 (3)	C18—C17—C16	122.2 (3)
O3—C2—C1	111.7 (2)	C18—C17—H17	118.9
C3—C2—C1	111.4 (2)	C16—C17—H17	118.9
O3—C2—H2	109.3	C17—C18—C19	120.2 (3)
C3—C2—H2	109.3	C17—C18—H18	119.9
C1—C2—H2	109.3	C19—C18—H18	119.9
O3—C4—C5	117.0 (2)	C20—C19—C18	118.5 (3)
O3—C4—C9	124.1 (2)	C20—C19—H19	120.8
C5—C4—C9	118.9 (2)	C18—C19—H19	120.8
C6—C5—C4	121.4 (3)	C19—C20—C15	120.2 (2)
C6—C5—Br1	119.0 (2)	C19—C20—C21	129.5 (2)
C4—C5—Br1	119.5 (2)	C15—C20—C21	110.1 (2)
C5—C6—C7	119.2 (3)	C20—C21—C10	115.0 (2)
C5—C6—H6	120.4	C20—C21—C22	111.8 (2)
C7—C6—H6	120.4	C10—C21—C22	101.5 (2)
C8—C7—C6	120.4 (3)	C20—C21—C14	102.7 (2)
C8—C7—H7	119.8	C10—C21—C14	114.5 (2)
C6—C7—H7	119.8	C22—C21—C14	111.8 (2)
C7—C8—C9	120.3 (3)	C23—C22—C21	103.6 (2)
C7—C8—H8	119.9	C23—C22—H22A	111.0
C9—C8—H8	119.9	C21—C22—H22A	111.0
C4—C9—C8	119.8 (3)	C23—C22—H22B	111.0
C4—C9—H9	120.1	C21—C22—H22B	111.0
C8—C9—H9	120.1	H22A—C22—H22B	109.0
C28—O4—C27	115.4 (2)	N2—C23—C22	104.6 (2)
C30—N1—C15	123.1 (2)	N2—C23—H23A	110.8
C30—N1—C14	118.7 (2)	C22—C23—H23A	110.8
C15—N1—C14	109.4 (2)	N2—C23—H23B	110.8
C24—N2—C23	111.79 (19)	C22—C23—H23B	110.8
C24—N2—C10	113.1 (2)	H23A—C23—H23B	108.9
C23—N2—C10	107.7 (2)	N2—C24—C25	109.6 (2)
C24—N2—HN2	114 (3)	N2—C24—H24A	109.8
C23—N2—HN2	105 (3)	C25—C24—H24A	109.8
C10—N2—HN2	104.4 (19)	N2—C24—H24B	109.8
C11—C10—N2	110.5 (3)	C25—C24—H24B	109.8
C11—C10—C21	115.57 (19)	H24A—C24—H24B	108.2
N2—C10—C21	104.6 (2)	C26—C25—C24	121.3 (2)
C11—C10—H10	108.6	C26—C25—C12	123.0 (2)
N2—C10—H10	108.6	C24—C25—C12	115.7 (2)
C21—C10—H10	108.6	C25—C26—C27	122.6 (2)
C10—C11—C12	108.6 (2)	C25—C26—H26	118.7
C10—C11—H11A	110.0	C27—C26—H26	118.7
C12—C11—H11A	110.0	O4—C27—C26	111.2 (2)
C10—C11—H11B	110.0	O4—C27—H27A	109.4
C12—C11—H11B	110.0	C26—C27—H27A	109.4
H11A—C11—H11B	108.4	O4—C27—H27B	109.4
C25—C12—C11	109.1 (2)	C26—C27—H27B	109.4
C25—C12—C13	114.1 (2)	H27A—C27—H27B	108.0
C11—C12—C13	106.3 (2)	O4—C28—C13	114.3 (2)
C25—C12—H12	109.1	O4—C28—C29	103.5 (2)
C11—C12—H12	109.1	C13—C28—C29	109.4 (2)
C13—C12—H12	109.1	O4—C28—H28	109.8
C14—C13—C28	107.9 (2)	C13—C28—H28	109.8
C14—C13—C12	112.4 (2)	C29—C28—H28	109.8
C28—C13—C12	117.9 (2)	C30—C29—C28	117.5 (2)
C14—C13—H13	105.9	C30—C29—H29A	107.9
C28—C13—H13	105.9	C28—C29—H29A	107.9
C12—C13—H13	105.9	C30—C29—H29B	107.9
N1—C14—C13	107.5 (2)	C28—C29—H29B	107.9
N1—C14—C21	104.44 (19)	H29A—C29—H29B	107.2
C13—C14—C21	117.1 (2)	O5—C30—N1	122.6 (3)
N1—C14—H14	109.2	O5—C30—C29	123.0 (2)
C13—C14—H14	109.2	N1—C30—C29	114.3 (2)
C21—C14—H14	109.2	HO6A—O6—HO6B	109 (5)
C16—C15—C20	121.8 (3)	HO7A—O7—HO7B	95 (3)
C16—C15—N1	128.3 (2)
C4—O3—C2—C3	162.6 (2)	C16—C15—C20—C21	172.5 (2)
C4—O3—C2—C1	−75.9 (3)	N1—C15—C20—C21	−7.4 (3)
O2—C1—C2—O3	151.4 (3)	C19—C20—C21—C10	−43.6 (4)
O1—C1—C2—O3	−28.7 (3)	C15—C20—C21—C10	141.2 (2)
O2—C1—C2—C3	−90.4 (4)	C19—C20—C21—C22	71.5 (3)
O1—C1—C2—C3	89.6 (3)	C15—C20—C21—C22	−103.7 (3)
C2—O3—C4—C5	−172.9 (2)	C19—C20—C21—C14	−168.6 (3)
C2—O3—C4—C9	4.3 (3)	C15—C20—C21—C14	16.2 (3)
O3—C4—C5—C6	175.5 (2)	C11—C10—C21—C20	−85.8 (3)
C9—C4—C5—C6	−1.9 (4)	N2—C10—C21—C20	152.4 (2)
O3—C4—C5—Br1	−1.2 (3)	C11—C10—C21—C22	153.3 (2)
C9—C4—C5—Br1	−178.61 (19)	N2—C10—C21—C22	31.6 (3)
C4—C5—C6—C7	0.4 (4)	C11—C10—C21—C14	32.7 (3)
Br1—C5—C6—C7	177.1 (2)	N2—C10—C21—C14	−89.0 (3)
C5—C6—C7—C8	0.7 (5)	N1—C14—C21—C20	−18.4 (2)
C6—C7—C8—C9	−0.2 (5)	C13—C14—C21—C20	100.3 (2)
O3—C4—C9—C8	−174.8 (2)	N1—C14—C21—C10	−143.8 (2)
C5—C4—C9—C8	2.4 (4)	C13—C14—C21—C10	−25.1 (3)
C7—C8—C9—C4	−1.4 (4)	N1—C14—C21—C22	101.5 (2)
C24—N2—C10—C11	−10.7 (3)	C13—C14—C21—C22	−139.8 (2)
C23—N2—C10—C11	−134.8 (2)	C20—C21—C22—C23	−165.6 (2)
C24—N2—C10—C21	114.3 (3)	C10—C21—C22—C23	−42.5 (3)
C23—N2—C10—C21	−9.8 (3)	C14—C21—C22—C23	80.0 (3)
N2—C10—C11—C12	63.0 (2)	C24—N2—C23—C22	−141.6 (2)
C21—C10—C11—C12	−55.5 (3)	C10—N2—C23—C22	−16.7 (3)
C10—C11—C12—C25	−54.8 (3)	C21—C22—C23—N2	36.9 (3)
C10—C11—C12—C13	68.6 (2)	C23—N2—C24—C25	75.7 (3)
C25—C12—C13—C14	58.5 (3)	C10—N2—C24—C25	−46.1 (3)
C11—C12—C13—C14	−61.8 (3)	N2—C24—C25—C26	−124.6 (3)
C25—C12—C13—C28	−68.0 (3)	N2—C24—C25—C12	54.9 (3)
C11—C12—C13—C28	171.8 (2)	C11—C12—C25—C26	175.9 (3)
C30—N1—C14—C13	38.7 (3)	C13—C12—C25—C26	57.2 (3)
C15—N1—C14—C13	−109.8 (2)	C11—C12—C25—C24	−3.7 (3)
C30—N1—C14—C21	163.8 (2)	C13—C12—C25—C24	−122.3 (2)
C15—N1—C14—C21	15.3 (3)	C24—C25—C26—C27	179.3 (2)
C28—C13—C14—N1	−70.5 (2)	C12—C25—C26—C27	−0.2 (4)
C12—C13—C14—N1	157.8 (2)	C28—O4—C27—C26	87.1 (3)
C28—C13—C14—C21	172.5 (2)	C25—C26—C27—O4	−65.2 (3)
C12—C13—C14—C21	40.8 (3)	C27—O4—C28—C13	−67.8 (3)
C30—N1—C15—C16	27.9 (4)	C27—O4—C28—C29	173.3 (2)
C14—N1—C15—C16	174.7 (2)	C14—C13—C28—O4	−71.0 (3)
C30—N1—C15—C20	−152.3 (2)	C12—C13—C28—O4	57.7 (3)
C14—N1—C15—C20	−5.4 (3)	C14—C13—C28—C29	44.6 (3)
C20—C15—C16—C17	2.8 (4)	C12—C13—C28—C29	173.2 (2)
N1—C15—C16—C17	−177.3 (3)	O4—C28—C29—C30	131.8 (2)
C15—C16—C17—C18	−0.2 (5)	C13—C28—C29—C30	9.6 (3)
C16—C17—C18—C19	−2.1 (5)	C15—N1—C30—O5	−22.1 (4)
C17—C18—C19—C20	1.7 (4)	C14—N1—C30—O5	−166.0 (2)
C18—C19—C20—C15	0.9 (4)	C15—N1—C30—C29	160.3 (2)
C18—C19—C20—C21	−173.9 (3)	C14—N1—C30—C29	16.3 (3)
C16—C15—C20—C19	−3.2 (4)	C28—C29—C30—O5	139.8 (3)
N1—C15—C20—C19	176.9 (2)	C28—C29—C30—N1	−42.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···O1	0.95 (3)	1.73 (3)	2.656 (3)	164 (3)
O6—HO6A···O2	0.74 (5)	2.16 (5)	2.845 (4)	156 (4)
O6—HO6B···O1^i	0.79 (6)	2.05 (6)	2.806 (4)	160 (5)
O7—HO7A···O2	0.87 (2)	2.37 (13)	2.905 (8)	120 (12)
O7—HO7B···O3^i	0.87 (2)	2.45 (4)	3.255 (8)	155 (9)

Symmetry code: (i) x, y+1, z.