4-Chloro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galacto­pyran­osyl)­benzyl­idene­amine

The title compound, C₃₃H₄₈ClNO₉, is an important chiral template for the synthesis of α-amino acids. The galacto­pyran­ose ring adopts a chair conformation. The crystal structure contains intermolecular C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.055
• wR factor = 0.134
• Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT707_ALERT_1_A D...A   Calc   13.307(6), Rep    3.479(4), Dev..    1638.00 Sigma
              C3   -O9      1.555   4.664
PLAT707_ALERT_1_A D...A   Calc    8.199(7), Rep    3.379(5), Dev..     688.57 Sigma
              C8   -O7      1.555   2.456
PLAT726_ALERT_1_A H...A   Calc    13.81590, Rep     2.63000 Dev...      11.19 Ang.
              H3   -O9      1.555   4.664
PLAT726_ALERT_1_A H...A   Calc     8.73800, Rep     2.47000 Dev...       6.27 Ang.
              H7   -O7      1.555   2.456
PLAT728_ALERT_1_A D-H..A  Calc       56.65, Rep      147.00 Dev...      90.35 Deg.
              C3   -H3   -O9      1.555   1.555   4.664
PLAT728_ALERT_1_A D-H..A  Calc       53.52, Rep      156.00 Dev...     102.48 Deg.
              C8   -H7   -O7      1.555   1.555   2.456

Alert level B
PLAT213_ALERT_2_B Atom C33     has ADP max/min Ratio .............       4.20 prolat
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.70 Ratio
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        C24
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        C30

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         49 Perc.
PLAT213_ALERT_2_C Atom C31     has ADP max/min Ratio .............       3.30 prolat
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   C18     ..       6.11 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C14
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for        C19
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C30    -   C33    ...       1.38 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3     ..  O9      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  O3      ..       2.62 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.47
           From the CIF: _reflns_number_total               8173
           Count of symmetry unique reflns         4583
           Completeness (_total/calc)            178.33%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3590
           Fraction of Friedel pairs measured     0.783
           Are heavy atom types Z>Si present          yes

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

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C33H48ClNO9	F(000) = 1368.00
Mr = 638.20	Dx = 1.179 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 22991 reflections
a = 10.9898 (4) Å	θ = 2.7–27.5°
b = 15.7406 (7) Å	µ = 0.16 mm^−1
c = 20.7781 (6) Å	T = 295 K
V = 3594.3 (2) Å^3	Block, colorless
Z = 4	0.31 × 0.28 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	4014 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.065
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.921, Tmax = 0.982	k = −20→20
31396 measured reflections	l = −26→26
8173 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0024Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.055	(Δ/σ)max = 0.001
wR(F^2) = 0.134	Δρmax = 0.57 e Å^−3
S = 1.01	Δρmin = −0.30 e Å^−3
4014 reflections	Absolute structure: Flack (1983), 3568 Friedel pairs
398 parameters	Absolute structure parameter: 0.1 (1)
H-atom parameters constrained

Special details

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cl(1)	0.2250 (1)	0.1964 (1)	0.78921 (7)	0.0923 (5)
O(1)	0.6053 (3)	0.5964 (2)	0.5693 (1)	0.0556 (9)
O(2)	0.8007 (3)	0.4090 (2)	0.5617 (1)	0.0510 (8)
O(3)	0.7188 (4)	0.3128 (2)	0.4959 (2)	0.100 (1)
O(4)	0.8494 (2)	0.4870 (2)	0.4424 (1)	0.0517 (8)
O(5)	1.0129 (3)	0.5710 (3)	0.4346 (2)	0.086 (1)
O(6)	0.6361 (2)	0.5866 (2)	0.4348 (1)	0.0515 (8)
O(7)	0.7271 (3)	0.6392 (3)	0.3472 (1)	0.080 (1)
O(8)	0.6672 (3)	0.7881 (2)	0.4813 (1)	0.063 (1)
O(9)	0.5000 (3)	0.8233 (2)	0.4257 (2)	0.073 (1)
N(1)	0.5698 (3)	0.4701 (2)	0.6183 (2)	0.053 (1)
C(1)	0.6651 (4)	0.5220 (3)	0.5914 (2)	0.052 (1)
C(2)	0.7257 (4)	0.4757 (3)	0.5350 (2)	0.046 (1)
C(3)	0.8067 (4)	0.5347 (3)	0.4968 (2)	0.045 (1)
C(4)	0.7365 (3)	0.6133 (3)	0.4757 (2)	0.044 (1)
C(5)	0.6828 (4)	0.6553 (3)	0.5356 (2)	0.050 (1)
C(6)	0.5948 (4)	0.4235 (3)	0.6658 (2)	0.052 (1)
C(7)	0.5046 (4)	0.3649 (3)	0.6951 (2)	0.050 (1)
C(8)	0.5342 (5)	0.3178 (3)	0.7500 (2)	0.059 (1)
C(9)	0.4483 (5)	0.2660 (3)	0.7784 (2)	0.061 (1)
C(10)	0.3348 (5)	0.2619 (3)	0.7541 (2)	0.063 (2)
C(11)	0.3022 (5)	0.3070 (4)	0.6983 (2)	0.069 (2)
C(12)	0.3887 (5)	0.3585 (3)	0.6695 (2)	0.064 (2)
C(13)	0.7900 (4)	0.3298 (3)	0.5377 (2)	0.058 (1)
C(14)	0.8786 (4)	0.2676 (3)	0.5695 (2)	0.061 (1)
C(15)	1.0027 (5)	0.3068 (4)	0.5786 (3)	0.083 (2)
C(16)	0.8884 (6)	0.1899 (4)	0.5263 (3)	0.094 (2)
C(17)	0.8246 (6)	0.2442 (4)	0.6342 (3)	0.092 (2)
C(18)	0.9578 (4)	0.5112 (3)	0.4167 (2)	0.059 (1)
C(19)	0.9960 (4)	0.4507 (3)	0.3631 (2)	0.057 (1)
C(20)	1.0038 (6)	0.3590 (4)	0.3886 (3)	0.089 (2)
C(21)	1.1181 (5)	0.4787 (4)	0.3364 (3)	0.095 (2)
C(22)	0.8993 (6)	0.4538 (4)	0.3095 (2)	0.082 (2)
C(23)	0.6429 (4)	0.6036 (3)	0.3713 (2)	0.056 (1)
C(24)	0.5310 (5)	0.5723 (3)	0.3362 (2)	0.078 (2)
C(25)	0.5234 (8)	0.4786 (5)	0.3400 (4)	0.136 (3)
C(26)	0.4170 (6)	0.6112 (6)	0.3682 (4)	0.133 (3)
C(27)	0.5339 (8)	0.6029 (7)	0.2688 (3)	0.136 (4)
C(28)	0.5976 (4)	0.7284 (3)	0.5194 (2)	0.062 (1)
C(29)	0.6069 (5)	0.8319 (3)	0.4366 (2)	0.057 (1)
C(30)	0.6887 (5)	0.8949 (3)	0.4010 (3)	0.088 (2)
C(31)	0.8000 (8)	0.8550 (5)	0.3770 (5)	0.136 (4)
C(32)	0.743 (1)	0.9587 (6)	0.4544 (5)	0.131 (6)
C(33)	0.6226 (8)	0.9434 (9)	0.3580 (7)	0.130 (6)
H(1)	0.7260	0.5363	0.6235	0.062*
H(2)	0.6634	0.4520	0.5072	0.054*
H(3)	0.8753	0.5513	0.5234	0.054*
H(4)	0.7893	0.6526	0.4530	0.053*
H(5)	0.7466	0.6759	0.5638	0.060*
H(6)	0.6759	0.4257	0.6841	0.063*
H(7)	0.6157	0.3207	0.7678	0.071*
H(8)	0.4682	0.2328	0.8163	0.073*
H(9)	0.2217	0.3004	0.6798	0.082*
H(10)	0.3675	0.3911	0.6315	0.077*
H(11)	1.0525	0.2959	0.5410	0.100*
H(12)	1.0409	0.2821	0.6162	0.099*
H(13)	0.9943	0.3677	0.5847	0.099*
H(14)	0.8270	0.1489	0.5388	0.113*
H(15)	0.9685	0.1648	0.5309	0.113*
H(16)	0.8757	0.2064	0.4818	0.113*
H(17)	0.8547	0.2839	0.6662	0.110*
H(18)	0.8494	0.1870	0.6457	0.110*
H(19)	0.7366	0.2472	0.6325	0.110*
H(20)	1.0855	0.3482	0.4044	0.107*
H(21)	0.9853	0.3199	0.3539	0.106*
H(22)	0.9459	0.3510	0.4234	0.107*
H(23)	1.1078	0.5192	0.3016	0.114*
H(24)	1.1612	0.4291	0.3206	0.114*
H(25)	1.1644	0.5048	0.3709	0.114*
H(26)	0.8388	0.4105	0.3185	0.098*
H(27)	0.9361	0.4431	0.2679	0.098*
H(28)	0.8607	0.5092	0.3092	0.098*
H(29)	0.5655	0.4535	0.3037	0.136*
H(30)	0.4382	0.4626	0.3388	0.136*
H(31)	0.5596	0.4584	0.3798	0.136*
H(32)	0.3887	0.5745	0.4026	0.140*
H(33)	0.3528	0.6184	0.3367	0.140*
H(34)	0.4390	0.6662	0.3859	0.140*
H(35)	0.4929	0.6574	0.2667	0.139*
H(36)	0.4930	0.5628	0.2407	0.139*
H(37)	0.6177	0.6096	0.2550	0.139*
H(38)	0.5668	0.7550	0.5583	0.074*
H(39)	0.5299	0.7076	0.4939	0.074*
H(40)	0.8627	0.8609	0.4095	0.139*
H(41)	0.8264	0.8823	0.3375	0.139*
H(42)	0.7850	0.7952	0.3689	0.139*
H(43)	0.6894	1.0067	0.4608	0.138*
H(44)	0.8229	0.9790	0.4413	0.137*
H(45)	0.7509	0.9271	0.4943	0.138*
H(46)	0.6191	0.9155	0.3165	0.141*
H(47)	0.6624	0.9981	0.3535	0.141*
H(48)	0.5407	0.9517	0.3743	0.141*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl(1)	0.094 (1)	0.0786 (9)	0.104 (1)	−0.0032 (8)	0.0315 (8)	0.0240 (8)
O(1)	0.056 (2)	0.049 (2)	0.061 (2)	0.012 (2)	0.016 (1)	0.013 (1)
O(2)	0.055 (2)	0.040 (2)	0.058 (2)	0.006 (1)	−0.014 (1)	−0.003 (1)
O(3)	0.104 (3)	0.062 (2)	0.134 (3)	−0.001 (2)	−0.069 (3)	−0.016 (2)
O(4)	0.046 (2)	0.050 (2)	0.060 (2)	−0.004 (1)	0.004 (1)	−0.011 (1)
O(5)	0.069 (2)	0.083 (3)	0.107 (3)	−0.036 (2)	0.021 (2)	−0.039 (2)
O(6)	0.046 (2)	0.056 (2)	0.052 (2)	−0.004 (1)	0.000 (1)	0.013 (1)
O(7)	0.076 (2)	0.103 (3)	0.061 (2)	−0.033 (2)	0.007 (2)	0.014 (2)
O(8)	0.056 (2)	0.053 (2)	0.079 (2)	0.006 (2)	0.009 (2)	0.018 (2)
O(9)	0.062 (2)	0.072 (2)	0.086 (2)	−0.001 (2)	−0.004 (2)	0.010 (2)
N(1)	0.058 (2)	0.048 (2)	0.054 (2)	0.004 (2)	0.005 (2)	0.010 (2)
C(1)	0.062 (3)	0.043 (3)	0.049 (2)	0.007 (2)	0.001 (2)	0.005 (2)
C(2)	0.047 (2)	0.040 (2)	0.050 (2)	0.007 (2)	−0.010 (2)	0.001 (2)
C(3)	0.042 (2)	0.046 (2)	0.046 (2)	0.001 (2)	−0.001 (2)	−0.008 (2)
C(4)	0.034 (2)	0.045 (2)	0.054 (2)	−0.003 (2)	−0.001 (2)	0.003 (2)
C(5)	0.056 (3)	0.041 (3)	0.054 (2)	0.003 (2)	0.008 (2)	0.002 (2)
C(6)	0.057 (3)	0.051 (3)	0.050 (2)	−0.001 (2)	−0.001 (2)	−0.004 (2)
C(7)	0.058 (3)	0.051 (3)	0.042 (2)	0.009 (2)	0.004 (2)	−0.000 (2)
C(8)	0.071 (3)	0.061 (3)	0.046 (2)	0.009 (3)	−0.009 (2)	0.004 (2)
C(9)	0.079 (3)	0.058 (3)	0.046 (2)	0.001 (3)	−0.003 (3)	0.014 (2)
C(10)	0.081 (4)	0.052 (3)	0.058 (3)	0.016 (3)	0.019 (3)	0.009 (2)
C(11)	0.054 (3)	0.076 (3)	0.076 (3)	0.006 (3)	−0.004 (2)	0.011 (3)
C(12)	0.074 (3)	0.063 (3)	0.055 (3)	0.006 (3)	0.006 (3)	0.019 (2)
C(13)	0.056 (3)	0.043 (3)	0.075 (3)	−0.001 (2)	−0.007 (2)	−0.002 (2)
C(14)	0.068 (3)	0.043 (3)	0.072 (3)	0.009 (2)	−0.004 (2)	−0.002 (2)
C(15)	0.059 (3)	0.080 (4)	0.109 (4)	0.025 (3)	−0.008 (3)	0.010 (3)
C(16)	0.127 (5)	0.048 (3)	0.107 (4)	0.022 (3)	−0.028 (4)	−0.007 (3)
C(17)	0.103 (5)	0.081 (4)	0.092 (4)	0.007 (4)	−0.003 (3)	0.018 (3)
C(18)	0.050 (3)	0.067 (3)	0.060 (3)	0.001 (3)	0.002 (2)	0.001 (2)
C(19)	0.059 (3)	0.047 (3)	0.064 (3)	0.005 (2)	0.009 (2)	−0.003 (2)
C(20)	0.106 (5)	0.063 (4)	0.096 (4)	0.025 (3)	0.022 (4)	0.002 (3)
C(21)	0.086 (4)	0.098 (5)	0.100 (4)	0.005 (4)	0.040 (3)	−0.003 (4)
C(22)	0.103 (4)	0.075 (4)	0.066 (3)	0.006 (3)	−0.002 (3)	−0.015 (3)
C(23)	0.061 (3)	0.050 (3)	0.056 (3)	−0.004 (2)	0.005 (2)	0.004 (2)
C(24)	0.065 (3)	0.072 (4)	0.067 (3)	−0.014 (3)	−0.015 (3)	0.016 (2)
C(25)	0.163 (8)	0.088 (5)	0.188 (8)	−0.043 (5)	−0.090 (7)	0.001 (5)
C(26)	0.061 (4)	0.175 (8)	0.164 (7)	−0.007 (5)	−0.021 (4)	−0.009 (6)
C(27)	0.151 (7)	0.18 (1)	0.072 (4)	−0.104 (8)	−0.041 (4)	0.056 (5)
C(28)	0.064 (3)	0.047 (3)	0.075 (3)	0.011 (2)	0.021 (2)	0.014 (2)
C(29)	0.057 (3)	0.042 (3)	0.072 (3)	0.012 (2)	0.011 (3)	0.006 (2)
C(30)	0.075 (3)	0.065 (3)	0.096 (3)	0.018 (3)	0.023 (3)	0.035 (3)
C(31)	0.139 (7)	0.105 (6)	0.18 (1)	0.023 (6)	0.118 (8)	0.069 (7)
C(32)	0.17 (2)	0.138 (8)	0.183 (9)	−0.09 (1)	0.06 (1)	−0.013 (7)
C(33)	0.099 (6)	0.18 (2)	0.18 (2)	−0.021 (8)	−0.012 (9)	0.16 (2)

Geometric parameters (Å, º)

Cl(1)—C(10)	1.747 (5)	C(3)—H(3)	0.9700
O(1)—C(1)	1.420 (5)	C(4)—H(4)	0.9700
O(1)—C(5)	1.440 (5)	C(5)—H(5)	0.9700
O(2)—C(2)	1.446 (5)	C(6)—H(6)	0.9700
O(2)—C(13)	1.347 (5)	C(8)—H(7)	0.9700
O(3)—C(13)	1.201 (6)	C(9)—H(8)	0.9700
O(4)—C(3)	1.435 (5)	C(11)—H(9)	0.9700
O(4)—C(18)	1.360 (5)	C(12)—H(10)	0.9700
O(5)—C(18)	1.180 (6)	C(15)—H(11)	0.9700
O(6)—C(4)	1.456 (5)	C(15)—H(12)	0.9700
O(6)—C(23)	1.348 (5)	C(15)—H(13)	0.9700
O(7)—C(23)	1.192 (6)	C(16)—H(14)	0.9700
O(8)—C(28)	1.448 (6)	C(16)—H(15)	0.9700
O(8)—C(29)	1.334 (6)	C(16)—H(16)	0.9700
O(9)—C(29)	1.204 (6)	C(17)—H(17)	0.9700
N(1)—C(1)	1.441 (6)	C(17)—H(18)	0.9700
N(1)—C(6)	1.259 (6)	C(17)—H(19)	0.9700
C(1)—C(2)	1.532 (6)	C(20)—H(20)	0.9700
C(2)—C(3)	1.511 (6)	C(20)—H(21)	0.9700
C(3)—C(4)	1.523 (6)	C(20)—H(22)	0.9700
C(4)—C(5)	1.528 (6)	C(21)—H(23)	0.9700
C(5)—C(28)	1.522 (6)	C(21)—H(24)	0.9700
C(6)—C(7)	1.485 (6)	C(21)—H(25)	0.9700
C(7)—C(8)	1.398 (6)	C(22)—H(26)	0.9700
C(7)—C(12)	1.383 (7)	C(22)—H(27)	0.9700
C(8)—C(9)	1.380 (7)	C(22)—H(28)	0.9700
C(9)—C(10)	1.347 (8)	C(25)—H(29)	0.9700
C(10)—C(11)	1.405 (7)	C(25)—H(30)	0.9700
C(11)—C(12)	1.386 (7)	C(25)—H(31)	0.9700
C(13)—C(14)	1.530 (7)	C(26)—H(32)	0.9700
C(14)—C(15)	1.509 (7)	C(26)—H(33)	0.9700
C(14)—C(16)	1.520 (7)	C(26)—H(34)	0.9700
C(14)—C(17)	1.515 (8)	C(27)—H(35)	0.9700
C(18)—C(19)	1.524 (7)	C(27)—H(36)	0.9700
C(19)—C(20)	1.539 (7)	C(27)—H(37)	0.9700
C(19)—C(21)	1.517 (7)	C(28)—H(38)	0.9700
C(19)—C(22)	1.540 (7)	C(28)—H(39)	0.9700
C(23)—C(24)	1.512 (7)	C(31)—H(40)	0.9700
C(24)—C(25)	1.480 (9)	C(31)—H(41)	0.9700
C(24)—C(26)	1.545 (9)	C(31)—H(42)	0.9700
C(24)—C(27)	1.482 (8)	C(32)—H(43)	0.9700
C(29)—C(30)	1.529 (7)	C(32)—H(44)	0.9700
C(30)—C(31)	1.460 (9)	C(32)—H(45)	0.9700
C(30)—C(32)	1.610 (9)	C(33)—H(46)	0.9700
C(30)—C(33)	1.380 (9)	C(33)—H(47)	0.9700
C(1)—H(1)	0.9700	C(33)—H(48)	0.9700
C(2)—H(2)	0.9700
Cl(1)—C(10)—C(9)	120.7 (4)	H(5)—C(5)—C(28)	109.0030
Cl(1)—C(10)—C(11)	117.8 (4)	C(5)—C(28)—H(38)	110.9229
O(1)—C(1)—N(1)	104.9 (3)	C(5)—C(28)—H(39)	109.6736
O(1)—C(1)—C(2)	110.2 (3)	H(6)—C(6)—C(7)	118.3162
C(5)—O(1)—C(1)	114.5 (3)	C(7)—C(8)—H(7)	119.9569
O(1)—C(5)—C(4)	110.3 (3)	C(7)—C(12)—H(10)	119.7677
O(1)—C(5)—C(28)	103.3 (3)	C(8)—C(9)—H(8)	120.7893
O(2)—C(2)—C(1)	107.4 (3)	H(7)—C(8)—C(9)	119.8169
O(2)—C(2)—C(3)	108.1 (3)	H(8)—C(9)—C(10)	119.1647
C(13)—O(2)—C(2)	118.7 (3)	C(10)—C(11)—H(9)	120.4289
O(2)—C(13)—O(3)	122.1 (4)	H(9)—C(11)—C(12)	121.1121
O(2)—C(13)—C(14)	112.2 (4)	C(11)—C(12)—H(10)	119.6840
O(3)—C(13)—C(14)	125.8 (4)	C(14)—C(15)—H(11)	109.6615
O(4)—C(3)—C(2)	106.6 (3)	C(14)—C(15)—H(12)	109.1761
O(4)—C(3)—C(4)	111.3 (3)	C(14)—C(15)—H(13)	109.5708
C(18)—O(4)—C(3)	116.8 (3)	C(14)—C(16)—H(14)	109.1603
O(4)—C(18)—O(5)	123.3 (4)	C(14)—C(16)—H(16)	109.7155
O(4)—C(18)—C(19)	110.7 (4)	C(14)—C(16)—H(15)	109.5307
O(5)—C(18)—C(19)	126.0 (4)	C(14)—C(17)—H(17)	108.5754
O(6)—C(4)—C(3)	108.5 (3)	C(14)—C(17)—H(19)	110.2629
O(6)—C(4)—C(5)	107.9 (3)	C(14)—C(17)—H(18)	109.5653
C(23)—O(6)—C(4)	118.3 (3)	H(12)—C(15)—H(11)	109.4716
O(6)—C(23)—O(7)	123.1 (4)	H(13)—C(15)—H(11)	109.4685
O(6)—C(23)—C(24)	111.3 (4)	H(13)—C(15)—H(12)	109.4783
O(7)—C(23)—C(24)	125.6 (4)	H(16)—C(16)—H(14)	109.4735
O(8)—C(28)—C(5)	106.6 (4)	H(15)—C(16)—H(14)	109.4746
C(29)—O(8)—C(28)	117.0 (4)	H(16)—C(16)—H(15)	109.4723
O(8)—C(29)—O(9)	123.9 (4)	H(19)—C(17)—H(17)	109.4728
O(8)—C(29)—C(30)	112.3 (4)	H(18)—C(17)—H(17)	109.4737
O(9)—C(29)—C(30)	123.8 (4)	H(19)—C(17)—H(18)	109.4727
N(1)—C(1)—C(2)	110.0 (3)	C(19)—C(20)—H(22)	109.9341
C(6)—N(1)—C(1)	118.4 (4)	C(19)—C(20)—H(20)	109.3854
N(1)—C(6)—C(7)	122.6 (4)	C(19)—C(20)—H(21)	109.0923
C(1)—C(2)—C(3)	111.5 (3)	C(19)—C(21)—H(23)	111.1387
C(2)—C(3)—C(4)	110.6 (3)	C(19)—C(21)—H(25)	108.4551
C(3)—C(4)—C(5)	108.2 (3)	C(19)—C(21)—H(24)	108.8015
C(4)—C(5)—C(28)	112.7 (3)	C(19)—C(22)—H(26)	108.2127
C(6)—C(7)—C(12)	120.1 (4)	C(19)—C(22)—H(28)	109.5759
C(6)—C(7)—C(8)	120.6 (4)	C(19)—C(22)—H(27)	110.6169
C(7)—C(8)—C(9)	120.2 (5)	H(22)—C(20)—H(20)	109.4661
C(12)—C(7)—C(8)	119.3 (4)	H(21)—C(20)—H(20)	109.4716
C(7)—C(12)—C(11)	120.5 (4)	H(22)—C(20)—H(21)	109.4767
C(8)—C(9)—C(10)	120.0 (4)	H(25)—C(21)—H(23)	109.4781
C(9)—C(10)—C(11)	121.4 (5)	H(24)—C(21)—H(23)	109.4694
C(10)—C(11)—C(12)	118.4 (5)	H(25)—C(21)—H(24)	109.4716
C(13)—C(14)—C(15)	111.5 (4)	H(28)—C(22)—H(26)	109.4746
C(13)—C(14)—C(17)	106.8 (4)	H(27)—C(22)—H(26)	109.4706
C(13)—C(14)—C(16)	107.8 (4)	H(28)—C(22)—H(27)	109.4677
C(17)—C(14)—C(15)	109.9 (4)	C(24)—C(25)—H(31)	110.4561
C(16)—C(14)—C(15)	109.8 (4)	C(24)—C(25)—H(29)	109.7201
C(17)—C(14)—C(16)	110.9 (4)	C(24)—C(25)—H(30)	108.2263
C(18)—C(19)—C(20)	110.5 (4)	C(24)—C(26)—H(32)	109.9376
C(18)—C(19)—C(22)	108.6 (4)	C(24)—C(26)—H(34)	108.2899
C(18)—C(19)—C(21)	109.3 (4)	C(24)—C(26)—H(33)	110.1774
C(22)—C(19)—C(20)	108.5 (4)	C(24)—C(27)—H(35)	108.6469
C(21)—C(19)—C(20)	110.4 (4)	C(24)—C(27)—H(36)	110.2276
C(22)—C(19)—C(21)	109.6 (4)	C(24)—C(27)—H(37)	109.5379
C(23)—C(24)—C(25)	110.2 (5)	H(31)—C(25)—H(29)	109.4691
C(23)—C(24)—C(26)	108.8 (5)	H(30)—C(25)—H(29)	109.4761
C(23)—C(24)—C(27)	109.4 (5)	H(31)—C(25)—H(30)	109.4717
C(26)—C(24)—C(25)	109.0 (6)	H(34)—C(26)—H(32)	109.4713
C(27)—C(24)—C(25)	112.1 (6)	H(33)—C(26)—H(32)	109.4716
C(27)—C(24)—C(26)	107.2 (6)	H(34)—C(26)—H(33)	109.4728
C(29)—C(30)—C(31)	112.3 (5)	H(36)—C(27)—H(35)	109.4716
C(29)—C(30)—C(32)	106.8 (6)	H(37)—C(27)—H(35)	109.4666
C(29)—C(30)—C(33)	111.2 (6)	H(37)—C(27)—H(36)	109.4728
C(32)—C(30)—C(31)	101.0 (7)	H(39)—C(28)—H(38)	109.4613
C(33)—C(30)—C(31)	117.2 (8)	C(30)—C(31)—H(42)	109.5199
C(33)—C(30)—C(32)	107.2 (8)	C(30)—C(31)—H(40)	108.4409
O(1)—C(1)—H(1)	110.4630	C(30)—C(31)—H(41)	110.4446
O(1)—C(5)—H(5)	110.4391	C(30)—C(32)—H(43)	110.5829
O(2)—C(2)—H(2)	110.4975	C(30)—C(32)—H(44)	110.2746
O(4)—C(3)—H(3)	109.5223	C(30)—C(32)—H(45)	107.5439
O(6)—C(4)—H(4)	110.6392	C(30)—C(33)—H(46)	110.1638
O(8)—C(28)—H(38)	111.1241	C(30)—C(33)—H(48)	109.8056
O(8)—C(28)—H(39)	108.9611	C(30)—C(33)—H(47)	108.4324
N(1)—C(1)—H(1)	111.5388	H(42)—C(31)—H(40)	109.4705
N(1)—C(6)—H(6)	119.1041	H(41)—C(31)—H(40)	109.4706
H(1)—C(1)—C(2)	109.6243	H(42)—C(31)—H(41)	109.4746
C(1)—C(2)—H(2)	109.3854	H(44)—C(32)—H(43)	109.4717
H(2)—C(2)—C(3)	109.8849	H(45)—C(32)—H(43)	109.4664
C(2)—C(3)—H(3)	108.9559	H(45)—C(32)—H(44)	109.4700
H(3)—C(3)—C(4)	109.7686	H(48)—C(33)—H(46)	109.4758
C(3)—C(4)—H(4)	110.8694	H(47)—C(33)—H(46)	109.4766
H(4)—C(4)—C(5)	110.5480	H(48)—C(33)—H(47)	109.4678
C(4)—C(5)—H(5)	110.8693

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O9^i	0.97	2.63	3.479 (4)	147
C8—H7···O7^ii	0.97	2.47	3.379 (5)	156
C15—H11···O3^iii	0.97	2.62	3.403 (7)	138

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1.