Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807016078/ci2334sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807016078/ci2334Isup2.hkl |
CCDC reference: 648063
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.015
- wR factor = 0.037
- Data-to-parameter ratio = 31.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT410_ALERT_2_C Short Intra H...H Contact H8 .. H11 .. 1.98 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H10 .. H18C .. 1.86 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.900 Tmax scaled 0.472 Tmin scaled 0.390 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 35.00 From the CIF: _reflns_number_total 7236 Count of symmetry unique reflns 3873 Completeness (_total/calc) 186.83% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3363 Fraction of Friedel pairs measured 0.868 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C19H18NO2+·I−·H2O | Z = 1 |
Mr = 437.26 | F(000) = 218 |
Triclinic, P1 | Dx = 1.647 Mg m−3 |
Hall symbol: P 1 | Melting point = 478–480 K |
a = 6.2412 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.2854 (2) Å | Cell parameters from 7236 reflections |
c = 9.1961 (2) Å | θ = 2.4–35.0° |
α = 68.134 (1)° | µ = 1.83 mm−1 |
β = 89.424 (1)° | T = 100 K |
γ = 87.720 (1)° | Block, yellow |
V = 440.97 (2) Å3 | 0.55 × 0.50 × 0.41 mm |
Bruker SMART APEX II CCD area-detector diffractometer | 7236 independent reflections |
Radiation source: fine-focus sealed tube | 7233 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
Detector resolution: 8.33 pixels mm-1 | θmax = 35.0°, θmin = 2.4° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −13→13 |
Tmin = 0.433, Tmax = 0.524 | l = −14→14 |
17774 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.015 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.037 | w = 1/[σ2(Fo2) + (0.0184P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.002 |
7236 reflections | Δρmax = 1.12 e Å−3 |
231 parameters | Δρmin = −0.59 e Å−3 |
4 restraints | Absolute structure: Flack (1983), 3382 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.012 (7) |
Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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. |
x | y | z | Uiso*/Ueq | ||
O1W | 0.35252 (19) | 0.78700 (16) | 0.47026 (13) | 0.02631 (18) | |
H2W | 0.460 (7) | 0.720 (5) | 0.502 (5) | 0.051 (9)* | |
H1W | 0.238 (8) | 0.721 (7) | 0.498 (6) | 0.075 (13)* | |
I1 | 0.858200 (2) | 0.547700 (2) | 0.575700 (2) | 0.01983 (2) | |
C1 | 0.17133 (16) | 0.29751 (13) | 1.11718 (13) | 0.01403 (15) | |
C2 | 0.02827 (17) | 0.23253 (14) | 1.03651 (14) | 0.01710 (17) | |
H2 | 0.0486 | 0.2535 | 0.9308 | 0.021* | |
C3 | −0.14230 (19) | 0.13746 (15) | 1.11567 (16) | 0.01976 (19) | |
H3 | −0.2358 | 0.0941 | 1.0623 | 0.024* | |
C4 | −0.1776 (2) | 0.10486 (16) | 1.27509 (16) | 0.0218 (2) | |
H4 | −0.2915 | 0.0384 | 1.3270 | 0.026* | |
C5 | −0.0426 (2) | 0.17188 (16) | 1.35372 (15) | 0.02073 (19) | |
H5 | −0.0672 | 0.1525 | 1.4587 | 0.025* | |
C6 | 0.13306 (17) | 0.26995 (14) | 1.27623 (13) | 0.01602 (16) | |
C7 | 0.27382 (18) | 0.34142 (15) | 1.35391 (13) | 0.01743 (17) | |
H7 | 0.2501 | 0.3258 | 1.4582 | 0.021* | |
C8 | 0.44388 (18) | 0.43300 (15) | 1.27663 (13) | 0.01684 (17) | |
H8 | 0.5348 | 0.4798 | 1.3289 | 0.020* | |
C9 | 0.48488 (16) | 0.45832 (13) | 1.11703 (12) | 0.01333 (15) | |
C10 | 0.66675 (17) | 0.55516 (14) | 1.03628 (13) | 0.01612 (16) | |
H10 | 0.6906 | 0.5676 | 0.9327 | 0.019* | |
C11 | 0.80316 (17) | 0.62814 (14) | 1.10441 (13) | 0.01603 (16) | |
H11 | 0.7749 | 0.6148 | 1.2077 | 0.019* | |
C12 | 0.98998 (17) | 0.72556 (13) | 1.03245 (13) | 0.01440 (15) | |
C13 | 1.11715 (17) | 0.78259 (14) | 1.12746 (13) | 0.01521 (16) | |
H13 | 1.0782 | 0.7578 | 1.2312 | 0.018* | |
C14 | 1.29947 (17) | 0.87503 (13) | 1.06985 (13) | 0.01470 (15) | |
C15 | 1.35771 (17) | 0.91485 (13) | 0.91238 (13) | 0.01508 (16) | |
C16 | 1.23208 (19) | 0.85885 (15) | 0.81666 (13) | 0.01743 (17) | |
H16 | 1.2700 | 0.8849 | 0.7126 | 0.021* | |
C17 | 1.05019 (18) | 0.76419 (15) | 0.87629 (13) | 0.01706 (17) | |
H17 | 0.9683 | 0.7265 | 0.8120 | 0.020* | |
C18 | 0.3876 (2) | 0.40600 (19) | 0.87976 (15) | 0.0230 (2) | |
H18A | 0.2952 | 0.4973 | 0.8109 | 0.035* | |
H18B | 0.3578 | 0.2981 | 0.8692 | 0.035* | |
H18C | 0.5345 | 0.4330 | 0.8529 | 0.035* | |
C19 | 1.6106 (2) | 1.04260 (19) | 0.71086 (16) | 0.0255 (2) | |
H19A | 1.7450 | 1.0990 | 0.6957 | 0.038* | |
H19B | 1.5064 | 1.1174 | 0.6383 | 0.038* | |
H19C | 1.6289 | 0.9356 | 0.6935 | 0.038* | |
N1 | 0.34977 (14) | 0.38996 (12) | 1.04316 (11) | 0.01365 (13) | |
O1 | 1.53880 (15) | 1.00661 (12) | 0.86700 (11) | 0.01949 (15) | |
O2 | 1.42743 (15) | 0.93093 (13) | 1.15838 (11) | 0.02027 (15) | |
H1O2 | 1.379 (6) | 0.894 (5) | 1.247 (4) | 0.045 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1W | 0.0228 (4) | 0.0352 (5) | 0.0214 (4) | −0.0053 (4) | 0.0021 (3) | −0.0107 (4) |
I1 | 0.01745 (3) | 0.02868 (3) | 0.01497 (2) | −0.00551 (2) | 0.00179 (2) | −0.00958 (2) |
C1 | 0.0113 (4) | 0.0135 (3) | 0.0171 (4) | −0.0015 (3) | 0.0010 (3) | −0.0054 (3) |
C2 | 0.0135 (4) | 0.0177 (4) | 0.0222 (5) | −0.0026 (3) | −0.0002 (3) | −0.0096 (4) |
C3 | 0.0144 (4) | 0.0179 (4) | 0.0274 (5) | −0.0040 (3) | 0.0010 (4) | −0.0087 (4) |
C4 | 0.0166 (4) | 0.0204 (4) | 0.0264 (5) | −0.0059 (4) | 0.0033 (4) | −0.0060 (4) |
C5 | 0.0169 (5) | 0.0224 (5) | 0.0197 (5) | −0.0049 (4) | 0.0038 (4) | −0.0038 (4) |
C6 | 0.0135 (4) | 0.0163 (4) | 0.0169 (4) | −0.0016 (3) | 0.0011 (3) | −0.0046 (3) |
C7 | 0.0153 (4) | 0.0209 (4) | 0.0155 (4) | −0.0021 (3) | 0.0013 (3) | −0.0058 (3) |
C8 | 0.0152 (4) | 0.0214 (4) | 0.0147 (4) | −0.0035 (3) | 0.0003 (3) | −0.0073 (3) |
C9 | 0.0112 (4) | 0.0142 (3) | 0.0150 (4) | −0.0014 (3) | −0.0003 (3) | −0.0059 (3) |
C10 | 0.0141 (4) | 0.0181 (4) | 0.0165 (4) | −0.0047 (3) | 0.0008 (3) | −0.0065 (3) |
C11 | 0.0130 (4) | 0.0184 (4) | 0.0185 (4) | −0.0036 (3) | 0.0017 (3) | −0.0086 (3) |
C12 | 0.0128 (4) | 0.0148 (4) | 0.0164 (4) | −0.0022 (3) | 0.0003 (3) | −0.0065 (3) |
C13 | 0.0133 (4) | 0.0165 (4) | 0.0167 (4) | −0.0038 (3) | 0.0016 (3) | −0.0069 (3) |
C14 | 0.0128 (4) | 0.0153 (4) | 0.0167 (4) | −0.0031 (3) | 0.0007 (3) | −0.0065 (3) |
C15 | 0.0135 (4) | 0.0148 (4) | 0.0161 (4) | −0.0024 (3) | 0.0015 (3) | −0.0047 (3) |
C16 | 0.0174 (4) | 0.0202 (4) | 0.0145 (4) | −0.0031 (3) | 0.0007 (3) | −0.0061 (3) |
C17 | 0.0159 (4) | 0.0197 (4) | 0.0168 (4) | −0.0036 (3) | 0.0002 (3) | −0.0079 (3) |
C18 | 0.0214 (5) | 0.0353 (6) | 0.0182 (5) | −0.0114 (4) | 0.0050 (4) | −0.0160 (4) |
C19 | 0.0227 (5) | 0.0303 (6) | 0.0196 (5) | −0.0069 (4) | 0.0066 (4) | −0.0043 (4) |
N1 | 0.0121 (3) | 0.0154 (3) | 0.0145 (3) | −0.0026 (3) | 0.0007 (3) | −0.0065 (3) |
O1 | 0.0179 (3) | 0.0207 (3) | 0.0187 (4) | −0.0075 (3) | 0.0050 (3) | −0.0054 (3) |
O2 | 0.0182 (4) | 0.0267 (4) | 0.0183 (4) | −0.0097 (3) | 0.0018 (3) | −0.0102 (3) |
O1W—H2W | 0.83 (4) | C11—C12 | 1.4527 (14) |
O1W—H1W | 0.89 (6) | C11—H11 | 0.93 |
C1—N1 | 1.3981 (13) | C12—C17 | 1.4007 (15) |
C1—C2 | 1.4094 (15) | C12—C13 | 1.4029 (15) |
C1—C6 | 1.4132 (16) | C13—C14 | 1.3846 (14) |
C2—C3 | 1.3812 (15) | C13—H13 | 0.93 |
C2—H2 | 0.93 | C14—O2 | 1.3559 (14) |
C3—C4 | 1.4051 (19) | C14—C15 | 1.4075 (15) |
C3—H3 | 0.93 | C15—O1 | 1.3609 (13) |
C4—C5 | 1.3748 (19) | C15—C16 | 1.3971 (16) |
C4—H4 | 0.93 | C16—C17 | 1.3937 (15) |
C5—C6 | 1.4122 (15) | C16—H16 | 0.93 |
C5—H5 | 0.93 | C17—H17 | 0.93 |
C6—C7 | 1.4149 (16) | C18—N1 | 1.4758 (15) |
C7—C8 | 1.3618 (15) | C18—H18A | 0.96 |
C7—H7 | 0.93 | C18—H18B | 0.96 |
C8—C9 | 1.4252 (15) | C18—H18C | 0.96 |
C8—H8 | 0.93 | C19—O1 | 1.4250 (16) |
C9—N1 | 1.3526 (14) | C19—H19A | 0.96 |
C9—C10 | 1.4476 (14) | C19—H19B | 0.96 |
C10—C11 | 1.3479 (15) | C19—H19C | 0.96 |
C10—H10 | 0.93 | O2—H1O2 | 0.81 (4) |
H2W—O1W—H1W | 107 (4) | C17—C12—C11 | 124.20 (10) |
N1—C1—C2 | 121.52 (10) | C13—C12—C11 | 117.06 (9) |
N1—C1—C6 | 119.10 (9) | C14—C13—C12 | 121.31 (10) |
C2—C1—C6 | 119.38 (9) | C14—C13—H13 | 119.3 |
C3—C2—C1 | 119.50 (11) | C12—C13—H13 | 119.3 |
C3—C2—H2 | 120.3 | O2—C14—C13 | 123.03 (10) |
C1—C2—H2 | 120.3 | O2—C14—C15 | 117.36 (9) |
C2—C3—C4 | 121.45 (11) | C13—C14—C15 | 119.61 (10) |
C2—C3—H3 | 119.3 | O1—C15—C16 | 125.34 (10) |
C4—C3—H3 | 119.3 | O1—C15—C14 | 115.10 (10) |
C5—C4—C3 | 119.51 (10) | C16—C15—C14 | 119.55 (9) |
C5—C4—H4 | 120.2 | C17—C16—C15 | 120.38 (10) |
C3—C4—H4 | 120.2 | C17—C16—H16 | 119.8 |
C4—C5—C6 | 120.48 (11) | C15—C16—H16 | 119.8 |
C4—C5—H5 | 119.8 | C16—C17—C12 | 120.40 (10) |
C6—C5—H5 | 119.8 | C16—C17—H17 | 119.8 |
C5—C6—C1 | 119.62 (11) | C12—C17—H17 | 119.8 |
C5—C6—C7 | 121.71 (10) | N1—C18—H18A | 109.5 |
C1—C6—C7 | 118.67 (9) | N1—C18—H18B | 109.5 |
C8—C7—C6 | 120.30 (10) | H18A—C18—H18B | 109.5 |
C8—C7—H7 | 119.9 | N1—C18—H18C | 109.5 |
C6—C7—H7 | 119.9 | H18A—C18—H18C | 109.5 |
C7—C8—C9 | 121.10 (10) | H18B—C18—H18C | 109.5 |
C7—C8—H8 | 119.4 | O1—C19—H19A | 109.5 |
C9—C8—H8 | 119.4 | O1—C19—H19B | 109.5 |
N1—C9—C8 | 118.40 (9) | H19A—C19—H19B | 109.5 |
N1—C9—C10 | 120.97 (9) | O1—C19—H19C | 109.5 |
C8—C9—C10 | 120.63 (9) | H19A—C19—H19C | 109.5 |
C11—C10—C9 | 122.96 (10) | H19B—C19—H19C | 109.5 |
C11—C10—H10 | 118.5 | C9—N1—C1 | 122.41 (9) |
C9—C10—H10 | 118.5 | C9—N1—C18 | 121.09 (9) |
C10—C11—C12 | 126.41 (10) | C1—N1—C18 | 116.48 (9) |
C10—C11—H11 | 116.8 | C15—O1—C19 | 117.27 (10) |
C12—C11—H11 | 116.8 | C14—O2—H1O2 | 107 (3) |
C17—C12—C13 | 118.74 (9) | ||
N1—C1—C2—C3 | 178.08 (10) | C11—C12—C13—C14 | 179.43 (10) |
C6—C1—C2—C3 | −2.42 (16) | C12—C13—C14—O2 | −179.38 (11) |
C1—C2—C3—C4 | 0.46 (18) | C12—C13—C14—C15 | 0.81 (17) |
C2—C3—C4—C5 | 1.40 (19) | O2—C14—C15—O1 | −0.07 (15) |
C3—C4—C5—C6 | −1.3 (2) | C13—C14—C15—O1 | 179.75 (10) |
C4—C5—C6—C1 | −0.71 (18) | O2—C14—C15—C16 | 179.46 (11) |
C4—C5—C6—C7 | 179.59 (12) | C13—C14—C15—C16 | −0.72 (16) |
N1—C1—C6—C5 | −177.93 (10) | O1—C15—C16—C17 | 179.48 (11) |
C2—C1—C6—C5 | 2.55 (16) | C14—C15—C16—C17 | 0.01 (17) |
N1—C1—C6—C7 | 1.78 (16) | C15—C16—C17—C12 | 0.64 (18) |
C2—C1—C6—C7 | −177.74 (10) | C13—C12—C17—C16 | −0.55 (17) |
C5—C6—C7—C8 | 178.93 (12) | C11—C12—C17—C16 | 179.88 (11) |
C1—C6—C7—C8 | −0.78 (17) | C8—C9—N1—C1 | 0.66 (15) |
C6—C7—C8—C9 | −0.32 (18) | C10—C9—N1—C1 | −179.25 (10) |
C7—C8—C9—N1 | 0.40 (17) | C8—C9—N1—C18 | −177.76 (11) |
C7—C8—C9—C10 | −179.69 (11) | C10—C9—N1—C18 | 2.34 (16) |
N1—C9—C10—C11 | 178.77 (11) | C2—C1—N1—C9 | 177.75 (10) |
C8—C9—C10—C11 | −1.13 (17) | C6—C1—N1—C9 | −1.76 (15) |
C9—C10—C11—C12 | 179.35 (11) | C2—C1—N1—C18 | −3.76 (15) |
C10—C11—C12—C17 | 2.90 (19) | C6—C1—N1—C18 | 176.73 (11) |
C10—C11—C12—C13 | −176.67 (11) | C16—C15—O1—C19 | −2.59 (17) |
C17—C12—C13—C14 | −0.17 (17) | C14—C15—O1—C19 | 176.91 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1O2···O1Wi | 0.82 (3) | 1.92 (3) | 2.7086 (15) | 163 (4) |
O1W—H1W···I1ii | 0.89 (6) | 2.77 (5) | 3.6584 (12) | 174 (5) |
O1W—H2W···I1 | 0.84 (4) | 2.78 (4) | 3.6005 (12) | 170 (4) |
C3—H3···O2iii | 0.93 | 2.51 | 3.1840 (16) | 129 |
Symmetry codes: (i) x+1, y, z+1; (ii) x−1, y, z; (iii) x−2, y−1, z. |