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The title N-(pyridin-2-ylmeth­yl)benzamide derivative, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit, which differ essentially in the orientation of the pyridine ring with respect to the benzene ring, with the two rings being inclined to each other by 53.3 (2) and 72.9 (2)° in mol­ecules A and B, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012866/su5514sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012866/su5514Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019012866/su5514Isup3.cml
Supplementary material

CCDC reference: 1954107

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.053
  • wR factor = 0.167
  • Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level A CHEM003_ALERT_1_A _chemical_formula_weight is missing Chemical formula mass (Da). The following tests will not be performed. CHEMW_01,CHEMW_02,CHEMW_03,DENSD_01 PLAT043_ALERT_1_A Calculated and Reported Mol. Weight Differ by .. 348.34 Check PLAT046_ALERT_1_A Reported Z, MW and D(calc) are Inconsistent .... 0.000 Check
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.78 Report PLAT220_ALERT_2_C Non-Solvent Resd 2 C Ueq(max)/Ueq(min) Range 3.3 Ratio PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C2A Check PLAT241_ALERT_2_C High 'MainMol' Ueq as Compared to Neighbors of C16B Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C11A Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C11B Check PLAT242_ALERT_2_C Low 'MainMol' Ueq as Compared to Neighbors of C14B Check PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00653 Ang. PLAT352_ALERT_3_C Short N-H (X0.87,N1.01A) N1B - H1B . 0.75 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C2A - C3A . 1.40 Ang. PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 1 Check
Alert level G PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 12 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 15 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 7 Info
3 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 11 ALERT level C = Check. Ensure it is not caused by an omission or oversight 5 ALERT level G = General information/check it is not something unexpected 5 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2013/1 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2009).

3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)\ benzamide top
Crystal data top
C18H18F2N2O3Dx = 1.345 Mg m3
Mr = 348.34Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 8521 reflections
a = 13.4775 (12) Åθ = 1.5–28.4°
b = 28.026 (3) ŵ = 0.11 mm1
c = 9.1085 (9) ÅT = 293 K
V = 3440.5 (6) Å3BLOCK, colourless
Z = 80.30 × 0.25 × 0.20 mm
F(000) = 1456
Data collection top
Bruker SMART APEXII area-detector
diffractometer
5868 reflections with I > 2σ(I)
ω and φ scansRint = 0.037
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 28.4°, θmin = 1.5°
Tmin = 0.642, Tmax = 0.785h = 1617
33263 measured reflectionsk = 3737
8521 independent reflectionsl = 1012
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: mixed
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0901P)2 + 0.6343P]
where P = (Fo2 + 2Fc2)/3
8521 reflections(Δ/σ)max < 0.001
459 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C3A0.6926 (5)0.85621 (17)0.0399 (6)0.0849 (15)
H3A0.7605130.8680250.0521060.102*
C3B0.8930 (3)0.64609 (14)0.4443 (5)0.0594 (10)
H3B0.8246970.6346830.4326380.071*
C1B0.9416 (4)0.63426 (16)0.5869 (5)0.0770 (14)
H1B10.9884340.6571120.6269910.092*
H1B20.9029040.6170750.6594640.092*
C1A0.6470 (6)0.8684 (2)0.0992 (6)0.0997 (19)
H1A10.6862260.8861350.1697940.120*
H1A20.6002450.8458920.1413890.120*
C2A0.6200 (6)0.8918 (2)0.0358 (7)0.111 (2)
H2A10.6413590.9245360.0492620.134*
H2A20.5555800.8843870.0776000.134*
C2B0.9698 (4)0.60887 (18)0.4527 (6)0.0821 (14)
H2B10.9487200.5759240.4428550.098*
H2B21.0341680.6159220.4104130.098*
C4B0.9158 (3)0.69265 (12)0.3746 (4)0.0533 (9)
H4B10.8717940.7171730.4120540.064*
H4B20.9836710.7019070.3957700.064*
C4A0.6728 (4)0.80972 (14)0.1111 (4)0.0599 (10)
H4A10.6053440.7996070.0908660.072*
H4A20.7178180.7856850.0732200.072*
C5A0.6758 (3)0.77698 (11)0.3535 (4)0.0421 (7)
C5B0.9153 (3)0.72633 (11)0.1320 (4)0.0418 (7)
C10A0.6486 (3)0.73121 (12)0.3097 (4)0.0423 (7)
H10A0.6369840.7250730.2108530.051*
C10B0.9444 (3)0.77079 (12)0.1793 (4)0.0425 (7)
H10B0.9561990.7758290.2786680.051*
C9A0.6385 (2)0.69462 (11)0.4113 (3)0.0398 (7)
C9B0.9564 (2)0.80857 (11)0.0804 (3)0.0393 (7)
C8B0.9374 (3)0.80117 (12)0.0676 (4)0.0443 (7)
H8B0.9449750.8259940.1344140.053*
C8A0.6566 (3)0.70345 (12)0.5597 (4)0.0450 (8)
H8A0.6498670.6790500.6282030.054*
C7A0.6847 (3)0.74862 (12)0.6046 (4)0.0467 (8)
H7A0.6969010.7546770.7033540.056*
C7B0.9069 (3)0.75644 (12)0.1152 (4)0.0471 (8)
H7B0.8940400.7513320.2142800.057*
C6A0.6947 (3)0.78472 (11)0.5024 (4)0.0428 (7)
C6B0.8957 (3)0.71980 (11)0.0171 (4)0.0441 (8)
C11B0.7764 (3)0.65960 (13)0.0361 (4)0.0556 (9)
H11B0.7705490.6539600.0697710.067*
C11A0.8125 (3)0.84507 (12)0.5158 (4)0.0523 (9)
H11A0.8208050.8460150.4089940.063*
C12A0.6111 (3)0.64577 (11)0.3570 (3)0.0399 (7)
C12B0.9851 (3)0.85610 (11)0.1403 (3)0.0394 (7)
C13B1.0486 (3)0.93630 (12)0.0893 (4)0.0527 (9)
H13A1.1124220.9449080.0478120.063*
H13B1.0537160.9384970.1953490.063*
C13A0.5474 (3)0.56661 (11)0.4218 (4)0.0504 (9)
H13C0.5589900.5605550.3183660.060*
H13D0.4772370.5618210.4405820.060*
C14A0.6056 (3)0.53127 (11)0.5106 (4)0.0468 (8)
C14B0.9714 (3)0.97029 (12)0.0361 (5)0.0574 (10)
C15A0.6971 (3)0.54131 (14)0.5656 (5)0.0604 (10)
H15A0.7265930.5709130.5504490.072*
C15B0.8969 (5)0.9869 (2)0.1237 (8)0.0966 (18)
H15B0.8936750.9777740.2217160.116*
C16A0.7455 (4)0.50557 (19)0.6458 (7)0.0808 (14)
H16A0.8083250.5111360.6843330.097*
C16B0.8265 (6)1.0173 (3)0.0664 (11)0.128 (3)
H16B0.7749801.0290110.1240560.154*
C17A0.7010 (5)0.46329 (18)0.6668 (7)0.0911 (17)
H17A0.7322840.4393710.7203850.109*
C17B0.8351 (6)1.0297 (2)0.0794 (11)0.122 (3)
H17B0.7875921.0489700.1240010.146*
C18A0.6109 (5)0.45618 (16)0.6094 (7)0.0910 (17)
H18A0.5807640.4267490.6247390.109*
C18B0.9148 (6)1.0132 (2)0.1574 (7)0.108 (2)
H18B0.9222441.0233750.2539960.130*
N1A0.5726 (3)0.61610 (10)0.4539 (3)0.0465 (7)
N1B1.0244 (3)0.88763 (10)0.0482 (4)0.0473 (7)
N2B0.9813 (4)0.98388 (15)0.1035 (4)0.0834 (13)
N2A0.5614 (3)0.48899 (12)0.5308 (5)0.0714 (10)
O1B0.9022 (2)0.68714 (8)0.2187 (3)0.0538 (6)
O1A0.6868 (2)0.81526 (8)0.2653 (3)0.0573 (7)
O2A0.7199 (2)0.83023 (8)0.5524 (3)0.0547 (7)
O2B0.8688 (2)0.67504 (9)0.0719 (3)0.0547 (7)
O3A0.6272 (2)0.63485 (8)0.2278 (3)0.0527 (6)
O3B0.9710 (2)0.86563 (9)0.2718 (3)0.0555 (7)
F2B0.7076 (2)0.69107 (10)0.0828 (3)0.0810 (8)
F1A0.8220 (3)0.88794 (10)0.5731 (5)0.1111 (12)
F2A0.8810 (2)0.81731 (11)0.5780 (4)0.0885 (9)
F1B0.7623 (3)0.61959 (10)0.1115 (4)0.0974 (10)
H1A0.552 (3)0.6261 (14)0.535 (5)0.053 (11)*
H1B1.040 (3)0.8804 (13)0.028 (4)0.039 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C3A0.108 (4)0.075 (3)0.072 (3)0.002 (3)0.004 (3)0.018 (2)
C3B0.059 (2)0.059 (2)0.060 (2)0.0020 (18)0.0005 (19)0.0089 (18)
C1B0.107 (4)0.073 (3)0.051 (3)0.007 (2)0.003 (2)0.016 (2)
C1A0.146 (6)0.095 (4)0.059 (3)0.009 (4)0.003 (3)0.021 (3)
C2A0.140 (6)0.097 (4)0.097 (5)0.029 (4)0.011 (4)0.001 (3)
C2B0.088 (4)0.071 (3)0.087 (4)0.017 (2)0.003 (3)0.019 (3)
C4B0.064 (2)0.0516 (18)0.044 (2)0.0016 (17)0.0037 (17)0.0031 (16)
C4A0.074 (3)0.058 (2)0.047 (2)0.0015 (19)0.0061 (19)0.0088 (17)
C5A0.0406 (19)0.0444 (16)0.0414 (18)0.0031 (13)0.0003 (14)0.0035 (13)
C5B0.0406 (18)0.0454 (15)0.0395 (18)0.0010 (13)0.0013 (13)0.0041 (13)
C10A0.0437 (19)0.0486 (16)0.0346 (17)0.0018 (14)0.0049 (13)0.0002 (13)
C10B0.045 (2)0.0489 (16)0.0334 (17)0.0004 (14)0.0027 (13)0.0028 (13)
C9A0.0374 (17)0.0476 (15)0.0344 (16)0.0033 (13)0.0024 (13)0.0009 (13)
C9B0.0331 (16)0.0482 (16)0.0365 (17)0.0019 (12)0.0008 (12)0.0013 (13)
C8B0.0449 (18)0.0546 (17)0.0334 (17)0.0044 (14)0.0005 (13)0.0037 (14)
C8A0.0497 (19)0.0513 (17)0.0341 (18)0.0008 (14)0.0002 (14)0.0031 (14)
C7A0.049 (2)0.0578 (19)0.0330 (17)0.0058 (16)0.0019 (14)0.0040 (15)
C7B0.047 (2)0.0619 (19)0.0323 (17)0.0067 (16)0.0003 (14)0.0025 (15)
C6A0.0392 (19)0.0469 (16)0.0425 (19)0.0003 (13)0.0027 (14)0.0071 (14)
C6B0.0366 (18)0.0520 (17)0.0437 (19)0.0042 (14)0.0038 (14)0.0079 (14)
C11B0.062 (3)0.060 (2)0.045 (2)0.0165 (18)0.0007 (17)0.0005 (17)
C11A0.052 (2)0.0510 (18)0.054 (2)0.0069 (16)0.0001 (17)0.0023 (16)
C12A0.0417 (18)0.0445 (15)0.0337 (16)0.0048 (13)0.0034 (13)0.0018 (13)
C12B0.0420 (18)0.0430 (15)0.0330 (16)0.0010 (13)0.0020 (13)0.0020 (13)
C13B0.068 (3)0.0457 (17)0.044 (2)0.0066 (16)0.0037 (18)0.0005 (15)
C13A0.062 (2)0.0428 (16)0.047 (2)0.0025 (15)0.0055 (17)0.0020 (14)
C14A0.056 (2)0.0431 (16)0.0416 (19)0.0038 (15)0.0052 (15)0.0040 (14)
C14B0.071 (3)0.0446 (17)0.057 (2)0.0013 (17)0.001 (2)0.0065 (16)
C15A0.052 (2)0.065 (2)0.065 (3)0.0005 (18)0.0015 (19)0.0017 (19)
C15B0.097 (4)0.093 (3)0.100 (4)0.018 (3)0.032 (4)0.019 (3)
C16A0.060 (3)0.092 (3)0.090 (4)0.016 (2)0.011 (3)0.004 (3)
C16B0.105 (5)0.116 (5)0.163 (8)0.044 (4)0.028 (5)0.004 (5)
C17A0.116 (5)0.067 (3)0.091 (4)0.027 (3)0.020 (3)0.013 (3)
C17B0.129 (6)0.094 (4)0.142 (7)0.048 (4)0.048 (5)0.014 (4)
C18A0.121 (5)0.053 (2)0.099 (4)0.005 (3)0.022 (4)0.018 (2)
C18B0.153 (7)0.098 (4)0.073 (4)0.053 (4)0.029 (4)0.003 (3)
N1A0.0626 (19)0.0413 (13)0.0355 (16)0.0002 (13)0.0056 (13)0.0034 (12)
N1B0.063 (2)0.0443 (14)0.0343 (16)0.0007 (13)0.0049 (14)0.0010 (13)
N2B0.115 (4)0.083 (2)0.052 (2)0.035 (2)0.007 (2)0.002 (2)
N2A0.086 (3)0.0524 (17)0.076 (3)0.0080 (17)0.015 (2)0.0087 (17)
O1B0.0715 (19)0.0454 (12)0.0445 (14)0.0040 (12)0.0072 (12)0.0056 (10)
O1A0.075 (2)0.0483 (13)0.0487 (15)0.0047 (12)0.0070 (13)0.0062 (11)
O2A0.0512 (16)0.0537 (13)0.0593 (16)0.0064 (11)0.0102 (12)0.0142 (12)
O2B0.0600 (17)0.0553 (13)0.0488 (15)0.0113 (11)0.0107 (12)0.0133 (11)
O3A0.0662 (17)0.0570 (13)0.0349 (13)0.0037 (12)0.0031 (11)0.0057 (10)
O3B0.0734 (19)0.0597 (14)0.0336 (13)0.0128 (13)0.0001 (12)0.0025 (11)
F2B0.0607 (16)0.0891 (17)0.093 (2)0.0114 (13)0.0134 (14)0.0211 (15)
F1A0.095 (2)0.0660 (15)0.172 (4)0.0286 (15)0.019 (2)0.0379 (19)
F2A0.0591 (16)0.1027 (19)0.104 (2)0.0103 (14)0.0187 (15)0.0355 (17)
F1B0.110 (2)0.0744 (16)0.108 (2)0.0407 (16)0.0166 (19)0.0294 (16)
Geometric parameters (Å, º) top
C3A—C2A1.397 (9)C7B—H7B0.9300
C3A—C1A1.449 (8)C6A—O2A1.396 (4)
C3A—C4A1.479 (6)C6B—O2B1.398 (4)
C3A—H3A0.9800C11B—F1B1.329 (4)
C3B—C2B1.471 (6)C11B—F2B1.348 (5)
C3B—C4B1.484 (5)C11B—O2B1.359 (5)
C3B—C1B1.492 (6)C11B—H11B0.9800
C3B—H3B0.9800C11A—F1A1.316 (4)
C1B—C2B1.465 (7)C11A—F2A1.334 (5)
C1B—H1B10.9700C11A—O2A1.357 (5)
C1B—H1B20.9700C11A—H11A0.9800
C1A—C2A1.441 (8)C12A—O3A1.235 (4)
C1A—H1A10.9700C12A—N1A1.319 (4)
C1A—H1A20.9700C12B—O3B1.242 (4)
C2A—H2A10.9700C12B—N1B1.328 (4)
C2A—H2A20.9700C13B—N1B1.452 (4)
C2B—H2B10.9700C13B—C14B1.492 (6)
C2B—H2B20.9700C13B—H13A0.9700
C4B—O1B1.440 (4)C13B—H13B0.9700
C4B—H4B10.9700C13A—N1A1.458 (4)
C4B—H4B20.9700C13A—C14A1.500 (5)
C4A—O1A1.426 (5)C13A—H13C0.9700
C4A—H4A10.9700C13A—H13D0.9700
C4A—H4A20.9700C14A—N2A1.339 (5)
C5A—O1A1.349 (4)C14A—C15A1.361 (6)
C5A—C10A1.392 (5)C14B—N2B1.333 (6)
C5A—C6A1.397 (5)C14B—C15B1.365 (7)
C5B—O1B1.365 (4)C15A—C16A1.400 (6)
C5B—C10B1.375 (5)C15A—H15A0.9300
C5B—C6B1.395 (5)C15B—C16B1.378 (10)
C10A—C9A1.388 (5)C15B—H15B0.9300
C10A—H10A0.9300C16A—C17A1.342 (8)
C10B—C9B1.399 (4)C16A—H16A0.9300
C10B—H10B0.9300C16B—C17B1.378 (11)
C9A—C8A1.396 (5)C16B—H16B0.9300
C9A—C12A1.501 (4)C17A—C18A1.337 (9)
C9B—C8B1.388 (5)C17A—H17A0.9300
C9B—C12B1.490 (4)C17B—C18B1.369 (11)
C8B—C7B1.389 (5)C17B—H17B0.9300
C8B—H8B0.9300C18A—N2A1.343 (6)
C8A—C7A1.383 (5)C18A—H18A0.9300
C8A—H8A0.9300C18B—N2B1.312 (7)
C7A—C6A1.381 (5)C18B—H18B0.9300
C7A—H7A0.9300N1A—H1A0.83 (4)
C7B—C6B1.370 (5)N1B—H1B0.75 (4)
C2A—C3A—C1A60.8 (4)C7A—C6A—O2A118.2 (3)
C2A—C3A—C4A120.9 (6)C7A—C6A—C5A121.5 (3)
C1A—C3A—C4A120.9 (5)O2A—C6A—C5A120.2 (3)
C2A—C3A—H3A114.6C7B—C6B—C5B121.1 (3)
C1A—C3A—H3A114.6C7B—C6B—O2B117.9 (3)
C4A—C3A—H3A114.6C5B—C6B—O2B121.0 (3)
C2B—C3B—C4B120.0 (4)F1B—C11B—F2B106.9 (3)
C2B—C3B—C1B59.2 (3)F1B—C11B—O2B106.0 (3)
C4B—C3B—C1B118.5 (4)F2B—C11B—O2B110.3 (3)
C2B—C3B—H3B115.8F1B—C11B—H11B111.2
C4B—C3B—H3B115.8F2B—C11B—H11B111.2
C1B—C3B—H3B115.8O2B—C11B—H11B111.2
C2B—C1B—C3B59.7 (3)F1A—C11A—F2A107.2 (4)
C2B—C1B—H1B1117.8F1A—C11A—O2A105.8 (3)
C3B—C1B—H1B1117.8F2A—C11A—O2A110.7 (3)
C2B—C1B—H1B2117.8F1A—C11A—H11A111.0
C3B—C1B—H1B2117.8F2A—C11A—H11A111.0
H1B1—C1B—H1B2114.9O2A—C11A—H11A111.0
C2A—C1A—C3A57.8 (4)O3A—C12A—N1A123.4 (3)
C2A—C1A—H1A1118.0O3A—C12A—C9A119.8 (3)
C3A—C1A—H1A1118.0N1A—C12A—C9A116.8 (3)
C2A—C1A—H1A2118.0O3B—C12B—N1B121.8 (3)
C3A—C1A—H1A2118.0O3B—C12B—C9B120.3 (3)
H1A1—C1A—H1A2115.2N1B—C12B—C9B117.8 (3)
C3A—C2A—C1A61.3 (4)N1B—C13B—C14B111.1 (3)
C3A—C2A—H2A1117.6N1B—C13B—H13A109.4
C1A—C2A—H2A1117.6C14B—C13B—H13A109.4
C3A—C2A—H2A2117.6N1B—C13B—H13B109.4
C1A—C2A—H2A2117.6C14B—C13B—H13B109.4
H2A1—C2A—H2A2114.7H13A—C13B—H13B108.0
C1B—C2B—C3B61.1 (3)N1A—C13A—C14A113.4 (3)
C1B—C2B—H2B1117.7N1A—C13A—H13C108.9
C3B—C2B—H2B1117.7C14A—C13A—H13C108.9
C1B—C2B—H2B2117.7N1A—C13A—H13D108.9
C3B—C2B—H2B2117.7C14A—C13A—H13D108.9
H2B1—C2B—H2B2114.8H13C—C13A—H13D107.7
O1B—C4B—C3B107.5 (3)N2A—C14A—C15A122.4 (4)
O1B—C4B—H4B1110.2N2A—C14A—C13A115.2 (4)
C3B—C4B—H4B1110.2C15A—C14A—C13A122.4 (3)
O1B—C4B—H4B2110.2N2B—C14B—C15B122.2 (5)
C3B—C4B—H4B2110.2N2B—C14B—C13B115.0 (4)
H4B1—C4B—H4B2108.5C15B—C14B—C13B122.8 (4)
O1A—C4A—C3A108.2 (4)C14A—C15A—C16A117.8 (4)
O1A—C4A—H4A1110.1C14A—C15A—H15A121.1
C3A—C4A—H4A1110.1C16A—C15A—H15A121.1
O1A—C4A—H4A2110.1C14B—C15B—C16B119.8 (6)
C3A—C4A—H4A2110.1C14B—C15B—H15B120.1
H4A1—C4A—H4A2108.4C16B—C15B—H15B120.1
O1A—C5A—C10A126.2 (3)C17A—C16A—C15A119.9 (5)
O1A—C5A—C6A115.8 (3)C17A—C16A—H16A120.1
C10A—C5A—C6A118.0 (3)C15A—C16A—H16A120.1
O1B—C5B—C10B125.8 (3)C17B—C16B—C15B117.6 (7)
O1B—C5B—C6B115.7 (3)C17B—C16B—H16B121.2
C10B—C5B—C6B118.5 (3)C15B—C16B—H16B121.2
C9A—C10A—C5A121.0 (3)C18A—C17A—C16A118.8 (5)
C9A—C10A—H10A119.5C18A—C17A—H17A120.6
C5A—C10A—H10A119.5C16A—C17A—H17A120.6
C5B—C10B—C9B121.1 (3)C18B—C17B—C16B118.7 (6)
C5B—C10B—H10B119.4C18B—C17B—H17B120.6
C9B—C10B—H10B119.4C16B—C17B—H17B120.6
C10A—C9A—C8A119.8 (3)C17A—C18A—N2A123.9 (5)
C10A—C9A—C12A118.6 (3)C17A—C18A—H18A118.0
C8A—C9A—C12A121.6 (3)N2A—C18A—H18A118.0
C8B—C9B—C10B119.4 (3)N2B—C18B—C17B123.6 (6)
C8B—C9B—C12B122.5 (3)N2B—C18B—H18B118.2
C10B—C9B—C12B118.1 (3)C17B—C18B—H18B118.2
C9B—C8B—C7B119.5 (3)C12A—N1A—C13A123.9 (3)
C9B—C8B—H8B120.2C12A—N1A—H1A121 (3)
C7B—C8B—H8B120.2C13A—N1A—H1A115 (3)
C7A—C8A—C9A119.8 (3)C12B—N1B—C13B123.5 (3)
C7A—C8A—H8A120.1C12B—N1B—H1B121 (3)
C9A—C8A—H8A120.1C13B—N1B—H1B115 (3)
C6A—C7A—C8A119.9 (3)C18B—N2B—C14B117.9 (5)
C6A—C7A—H7A120.1C14A—N2A—C18A117.2 (4)
C8A—C7A—H7A120.1C5B—O1B—C4B117.9 (3)
C6B—C7B—C8B120.4 (3)C5A—O1A—C4A119.1 (3)
C6B—C7B—H7B119.8C11A—O2A—C6A115.0 (3)
C8B—C7B—H7B119.8C11B—O2B—C6B116.0 (3)
C4B—C3B—C1B—C2B109.8 (5)C10B—C9B—C12B—N1B160.6 (3)
C4A—C3A—C1A—C2A110.6 (7)N1A—C13A—C14A—N2A154.4 (4)
C4A—C3A—C2A—C1A110.6 (7)N1A—C13A—C14A—C15A26.1 (5)
C4B—C3B—C2B—C1B107.3 (5)N1B—C13B—C14B—N2B82.7 (4)
C2B—C3B—C4B—O1B84.0 (5)N1B—C13B—C14B—C15B98.2 (5)
C1B—C3B—C4B—O1B153.0 (4)N2A—C14A—C15A—C16A0.1 (6)
C2A—C3A—C4A—O1A81.6 (7)C13A—C14A—C15A—C16A179.4 (4)
C1A—C3A—C4A—O1A153.9 (5)N2B—C14B—C15B—C16B2.7 (10)
O1A—C5A—C10A—C9A179.3 (3)C13B—C14B—C15B—C16B178.3 (6)
C6A—C5A—C10A—C9A1.3 (5)C14A—C15A—C16A—C17A0.5 (8)
O1B—C5B—C10B—C9B179.4 (3)C14B—C15B—C16B—C17B0.1 (12)
C6B—C5B—C10B—C9B1.4 (5)C15A—C16A—C17A—C18A0.4 (9)
C5A—C10A—C9A—C8A0.6 (5)C15B—C16B—C17B—C18B3.0 (13)
C5A—C10A—C9A—C12A178.7 (3)C16A—C17A—C18A—N2A0.1 (10)
C5B—C10B—C9B—C8B0.9 (5)C16B—C17B—C18B—N2B3.9 (12)
C5B—C10B—C9B—C12B178.2 (3)O3A—C12A—N1A—C13A2.1 (6)
C10B—C9B—C8B—C7B0.1 (5)C9A—C12A—N1A—C13A176.3 (3)
C12B—C9B—C8B—C7B177.3 (3)C14A—C13A—N1A—C12A117.2 (4)
C10A—C9A—C8A—C7A0.1 (5)O3B—C12B—N1B—C13B3.8 (6)
C12A—C9A—C8A—C7A177.9 (3)C9B—C12B—N1B—C13B175.2 (3)
C9A—C8A—C7A—C6A0.0 (5)C14B—C13B—N1B—C12B101.4 (4)
C9B—C8B—C7B—C6B0.0 (5)C17B—C18B—N2B—C14B1.5 (11)
C8A—C7A—C6A—O2A177.8 (3)C15B—C14B—N2B—C18B1.9 (8)
C8A—C7A—C6A—C5A0.8 (5)C13B—C14B—N2B—C18B179.0 (5)
O1A—C5A—C6A—C7A179.1 (3)C15A—C14A—N2A—C18A0.3 (7)
C10A—C5A—C6A—C7A1.5 (5)C13A—C14A—N2A—C18A179.8 (5)
O1A—C5A—C6A—O2A2.1 (5)C17A—C18A—N2A—C14A0.4 (9)
C10A—C5A—C6A—O2A178.4 (3)C10B—C5B—O1B—C4B2.7 (5)
C8B—C7B—C6B—C5B0.5 (5)C6B—C5B—O1B—C4B176.5 (3)
C8B—C7B—C6B—O2B177.4 (3)C3B—C4B—O1B—C5B177.4 (3)
O1B—C5B—C6B—C7B179.5 (3)C10A—C5A—O1A—C4A2.0 (6)
C10B—C5B—C6B—C7B1.2 (5)C6A—C5A—O1A—C4A177.5 (3)
O1B—C5B—C6B—O2B2.7 (5)C3A—C4A—O1A—C5A178.0 (4)
C10B—C5B—C6B—O2B178.1 (3)F1A—C11A—O2A—C6A179.5 (3)
C10A—C9A—C12A—O3A21.9 (5)F2A—C11A—O2A—C6A63.7 (4)
C8A—C9A—C12A—O3A156.1 (3)C7A—C6A—O2A—C11A110.5 (4)
C10A—C9A—C12A—N1A159.6 (3)C5A—C6A—O2A—C11A72.5 (4)
C8A—C9A—C12A—N1A22.4 (5)F1B—C11B—O2B—C6B173.3 (3)
C8B—C9B—C12B—O3B156.8 (3)F2B—C11B—O2B—C6B58.0 (4)
C10B—C9B—C12B—O3B20.3 (5)C7B—C6B—O2B—C11B111.5 (4)
C8B—C9B—C12B—N1B22.2 (5)C5B—C6B—O2B—C11B71.5 (4)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3 and Cg6 are the centroids of the N2A/C14A–C18A, C5A–C10A and C5B–C10B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C11A—H11A···O3B0.982.443.136 (5)128
C11B—H11B···O3A0.982.473.210 (5)132
C4B—H4B1···Cg30.972.873.689 (4)143
C4A—H4A2···Cg60.972.903.717 (5)143
N1A—H1A···O3Bi0.84 (4)2.08 (4)2.895 (4)163 (4)
N1B—H1B···O3Aii0.75 (4)2.21 (4)2.939 (4)164 (4)
C13A—H13C···N2Biii0.972.553.347 (5)140
C13A—H13D···F1Ai0.972.523.294 (6)136
C13B—H13B···Cg2iv0.972.733.748 (4)137
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+1/2, y+3/2, z; (iii) x1/2, y+3/2, z; (iv) x+1/2, y+3/2, z+1.
 

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