N-Cyclo­hexyl­tryptamine: freebase, bromide and fumarate

Naeem, M.; Le, A.N.; Bauer, B.E.; Chadeayne, A.R.; Golen, J.A.; Manke, D.R.

doi:10.1107/S2056989023006217

N-Cyclohexyltryptamine: freebase, bromide and fumarate

M. Naeem, A. N. Le, B. E. Bauer, A. R. Chadeayne, J. A. Golen and D. R. Manke

The crystal structure of the freebase of the monoalkyl tryptamine N-cyclohexyltryptamine is presented, along with those of its bromide and fumarate salts.

Keywords: crystal structure; tryptamines; indoles; hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023006217/tx2070sup1.cif Contains datablocks I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023006217/tx2070Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023006217/tx2070IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989023006217/tx2070IIIsup4.hkl Contains datablock III

CCDC references: 2281772; 2281771; 2281770

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.005 Å
R factor = 0.048
wR factor = 0.124
Data-to-parameter ratio = 15.3

Structure: II

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.007 Å
R factor = 0.045
wR factor = 0.109
Data-to-parameter ratio = 18.0

Structure: III

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.002 Å
R factor = 0.043
wR factor = 0.121
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Datablock: umd2564i_a



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.500
           From the CIF: _refine_ls_abs_structure_Flack_su    0.700
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5       --C6       .        7.0 s.u.
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C9 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00506 Ang.
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N2       --H2       .     Please Check
PLAT767_ALERT_4_C INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.700 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.20 Check
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

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

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




Datablock: umd2557f_a



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00656 Ang.
PLAT767_ALERT_4_C INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.903 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          7 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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




Datablock: umd2591d_a



Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT767_ALERT_4_C INS Embedded LIST 6 Instruction Should be LIST 4     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          7 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info
PLAT992_ALERT_5_G Repd & Actual _reflns_number_gt Values Differ by          3 Check

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

For all structures, data collection: APEX4 (Bruker, 2021); cell refinement: SAINT (Bruker, 2021); data reduction: SAINT (Bruker, 2021); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

N-[2-(1H-Indol-3-yl)ethyl]cyclohexanamine (I) top

Crystal data top

C₁₆H₂₂N₂	F(000) = 264
M_r = 242.35	D_x = 1.178 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.5446 (6) Å	Cell parameters from 8705 reflections
b = 10.3990 (7) Å	θ = 2.7–25.8°
c = 8.6149 (6) Å	µ = 0.07 mm⁻¹
β = 116.784 (2)°	T = 297 K
V = 683.35 (8) Å³	Block, colourless
Z = 2	0.35 × 0.24 × 0.2 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	2396 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.034
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 25.8°, θ_min = 3.3°
T_min = 0.645, T_max = 0.745	h = −10→10
18695 measured reflections	k = −12→12
2621 independent reflections	l = −10→10

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0573P)² + 0.1584P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.124	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.26 e Å⁻³
2621 reflections	Δρ_min = −0.16 e Å⁻³
171 parameters	Absolute structure: Flack x determined using 1039 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: 0.5 (7)

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

	x	y	z	U_iso*/U_eq
N1	0.6840 (4)	0.3201 (3)	0.7683 (3)	0.0574 (6)
N2	0.4242 (4)	0.5812 (3)	0.0943 (3)	0.0632 (7)
C1	0.6257 (4)	0.3382 (4)	0.5918 (4)	0.0653 (9)
H1A	0.570884	0.275362	0.507790	0.078*
C2	0.7549 (4)	0.4345 (3)	0.8487 (4)	0.0512 (7)
C3	0.8321 (4)	0.4672 (3)	1.0235 (4)	0.0608 (8)
H3	0.840170	0.407744	1.107439	0.073*
C4	0.8964 (5)	0.5900 (4)	1.0695 (5)	0.0692 (9)
H4	0.950320	0.612645	1.186509	0.083*
C5	0.8830 (5)	0.6805 (4)	0.9467 (5)	0.0709 (9)
H5	0.926088	0.763121	0.981803	0.085*
C6	0.8069 (4)	0.6495 (3)	0.7743 (5)	0.0660 (9)
H6	0.797958	0.710952	0.692294	0.079*
C7	0.7419 (4)	0.5244 (3)	0.7208 (4)	0.0539 (7)
C8	0.6589 (4)	0.4598 (4)	0.5573 (4)	0.0619 (8)
C9	0.6235 (5)	0.5204 (5)	0.3860 (4)	0.0855 (13)
H9A	0.642061	0.612333	0.403785	0.103*
H9B	0.709578	0.488038	0.351364	0.103*
C10	0.4504 (5)	0.4997 (4)	0.2431 (4)	0.0721 (11)
H10A	0.361947	0.519546	0.280822	0.086*
H10B	0.437557	0.410028	0.208452	0.086*
C11	0.2920 (4)	0.5382 (3)	−0.0766 (3)	0.0492 (6)
H11	0.177680	0.540657	−0.075896	0.059*
C12	0.3181 (4)	0.4030 (3)	−0.1291 (4)	0.0596 (8)
H12A	0.431796	0.397430	−0.128156	0.072*
H12B	0.315875	0.341579	−0.045337	0.072*
C13	0.1762 (6)	0.3695 (4)	−0.3085 (5)	0.0757 (10)
H13A	0.196778	0.283691	−0.339441	0.091*
H13B	0.063234	0.369608	−0.307234	0.091*
C14	0.1723 (5)	0.4639 (5)	−0.4431 (5)	0.0786 (11)
H14A	0.281049	0.458099	−0.452537	0.094*
H14B	0.076703	0.442457	−0.555435	0.094*
C15	0.1490 (5)	0.5982 (4)	−0.3946 (4)	0.0705 (9)
H15A	0.033473	0.606436	−0.400188	0.085*
H15B	0.155915	0.657786	−0.477959	0.085*
C16	0.2870 (5)	0.6337 (3)	−0.2129 (4)	0.0657 (9)
H16A	0.262024	0.718893	−0.183813	0.079*
H16B	0.401106	0.636367	−0.211442	0.079*
H2	0.524 (3)	0.594 (5)	0.083 (5)	0.091 (14)*
H1	0.672 (5)	0.249 (2)	0.813 (4)	0.067 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0606 (15)	0.0598 (16)	0.0454 (13)	0.0075 (12)	0.0183 (11)	0.0039 (11)
N2	0.0709 (17)	0.0612 (17)	0.0445 (14)	−0.0103 (14)	0.0146 (12)	0.0061 (12)
C1	0.0541 (17)	0.092 (3)	0.0430 (16)	0.0035 (17)	0.0155 (13)	−0.0069 (17)
C2	0.0454 (14)	0.0590 (19)	0.0470 (15)	0.0150 (12)	0.0188 (12)	0.0066 (12)
C3	0.0663 (19)	0.064 (2)	0.0512 (16)	0.0055 (16)	0.0256 (15)	0.0008 (15)
C4	0.070 (2)	0.074 (2)	0.066 (2)	−0.0022 (18)	0.0326 (17)	−0.0135 (19)
C5	0.069 (2)	0.066 (2)	0.085 (3)	−0.0005 (17)	0.041 (2)	−0.0092 (19)
C6	0.0566 (17)	0.061 (2)	0.092 (3)	0.0139 (15)	0.0436 (18)	0.0245 (18)
C7	0.0422 (14)	0.0677 (19)	0.0545 (16)	0.0148 (14)	0.0243 (13)	0.0098 (15)
C8	0.0475 (16)	0.087 (2)	0.0490 (17)	0.0113 (16)	0.0200 (14)	0.0142 (16)
C9	0.062 (2)	0.136 (4)	0.0550 (19)	0.008 (2)	0.0229 (16)	0.027 (2)
C10	0.079 (2)	0.073 (2)	0.0464 (17)	−0.0146 (17)	0.0123 (16)	0.0137 (15)
C11	0.0474 (14)	0.0523 (16)	0.0432 (14)	0.0020 (12)	0.0162 (11)	0.0029 (12)
C12	0.0606 (17)	0.0540 (18)	0.0619 (18)	0.0051 (15)	0.0255 (15)	0.0053 (15)
C13	0.088 (3)	0.064 (2)	0.068 (2)	−0.0063 (18)	0.0290 (19)	−0.0126 (17)
C14	0.085 (3)	0.097 (3)	0.0528 (19)	0.001 (2)	0.0302 (18)	−0.0077 (19)
C15	0.071 (2)	0.088 (3)	0.0477 (17)	0.0130 (19)	0.0224 (15)	0.0168 (17)
C16	0.084 (2)	0.0551 (19)	0.0510 (18)	0.0032 (16)	0.0247 (17)	0.0092 (14)

Geometric parameters (Å, º) top

N1—C1	1.383 (4)	C9—H9B	0.9700
N1—C2	1.372 (4)	C9—C10	1.452 (5)
N1—H1	0.864 (14)	C10—H10A	0.9700
N2—C10	1.467 (4)	C10—H10B	0.9700
N2—C11	1.464 (4)	C11—H11	0.9800
N2—H2	0.912 (14)	C11—C12	1.523 (4)
C1—H1A	0.9300	C11—C16	1.524 (4)
C1—C8	1.357 (5)	C12—H12A	0.9700
C2—C3	1.388 (4)	C12—H12B	0.9700
C2—C7	1.410 (4)	C12—C13	1.514 (5)
C3—H3	0.9300	C13—H13A	0.9700
C3—C4	1.375 (5)	C13—H13B	0.9700
C4—H4	0.9300	C13—C14	1.508 (6)
C4—C5	1.382 (5)	C14—H14A	0.9700
C5—H5	0.9300	C14—H14B	0.9700
C5—C6	1.364 (5)	C14—C15	1.497 (6)
C6—H6	0.9300	C15—H15A	0.9700
C6—C7	1.408 (5)	C15—H15B	0.9700
C7—C8	1.428 (5)	C15—C16	1.521 (5)
C8—C9	1.505 (4)	C16—H16A	0.9700
C9—H9A	0.9700	C16—H16B	0.9700

C1—N1—H1	124 (3)	C9—C10—H10A	109.5
C2—N1—C1	107.2 (3)	C9—C10—H10B	109.5
C2—N1—H1	129 (2)	H10A—C10—H10B	108.1
C10—N2—H2	113 (3)	N2—C11—H11	107.8
C11—N2—C10	116.6 (3)	N2—C11—C12	115.5 (3)
C11—N2—H2	106 (2)	N2—C11—C16	108.5 (2)
N1—C1—H1A	124.5	C12—C11—H11	107.8
C8—C1—N1	111.1 (3)	C12—C11—C16	109.3 (2)
C8—C1—H1A	124.5	C16—C11—H11	107.8
N1—C2—C3	130.3 (3)	C11—C12—H12A	109.4
N1—C2—C7	108.6 (3)	C11—C12—H12B	109.4
C3—C2—C7	121.1 (3)	H12A—C12—H12B	108.0
C2—C3—H3	120.9	C13—C12—C11	111.0 (3)
C4—C3—C2	118.3 (3)	C13—C12—H12A	109.4
C4—C3—H3	120.9	C13—C12—H12B	109.4
C3—C4—H4	119.1	C12—C13—H13A	109.3
C3—C4—C5	121.8 (4)	C12—C13—H13B	109.3
C5—C4—H4	119.1	H13A—C13—H13B	108.0
C4—C5—H5	119.8	C14—C13—C12	111.4 (3)
C6—C5—C4	120.5 (4)	C14—C13—H13A	109.3
C6—C5—H5	119.8	C14—C13—H13B	109.3
C5—C6—H6	120.0	C13—C14—H14A	109.5
C5—C6—C7	119.9 (3)	C13—C14—H14B	109.5
C7—C6—H6	120.0	H14A—C14—H14B	108.1
C2—C7—C8	106.7 (3)	C15—C14—C13	110.6 (3)
C6—C7—C2	118.4 (3)	C15—C14—H14A	109.5
C6—C7—C8	134.9 (3)	C15—C14—H14B	109.5
C1—C8—C7	106.4 (3)	C14—C15—H15A	109.2
C1—C8—C9	129.4 (4)	C14—C15—H15B	109.2
C7—C8—C9	124.1 (4)	C14—C15—C16	112.0 (3)
C8—C9—H9A	108.2	H15A—C15—H15B	107.9
C8—C9—H9B	108.2	C16—C15—H15A	109.2
H9A—C9—H9B	107.3	C16—C15—H15B	109.2
C10—C9—C8	116.5 (3)	C11—C16—H16A	109.2
C10—C9—H9A	108.2	C11—C16—H16B	109.2
C10—C9—H9B	108.2	C15—C16—C11	112.0 (3)
N2—C10—H10A	109.5	C15—C16—H16A	109.2
N2—C10—H10B	109.5	C15—C16—H16B	109.2
C9—C10—N2	110.6 (3)	H16A—C16—H16B	107.9

N1—C1—C8—C7	−0.6 (4)	C4—C5—C6—C7	−0.2 (5)
N1—C1—C8—C9	178.0 (3)	C5—C6—C7—C2	1.1 (4)
N1—C2—C3—C4	178.7 (3)	C5—C6—C7—C8	−179.2 (3)
N1—C2—C7—C6	179.9 (3)	C6—C7—C8—C1	−179.4 (3)
N1—C2—C7—C8	0.2 (3)	C6—C7—C8—C9	1.9 (5)
N2—C11—C12—C13	−179.1 (3)	C7—C2—C3—C4	−0.2 (4)
N2—C11—C16—C15	−178.4 (3)	C7—C8—C9—C10	−134.5 (4)
C1—N1—C2—C3	−179.5 (3)	C8—C9—C10—N2	170.4 (4)
C1—N1—C2—C7	−0.5 (3)	C10—N2—C11—C12	−56.0 (4)
C1—C8—C9—C10	47.2 (6)	C10—N2—C11—C16	−179.0 (3)
C2—N1—C1—C8	0.7 (4)	C11—N2—C10—C9	156.9 (4)
C2—C3—C4—C5	1.2 (5)	C11—C12—C13—C14	58.1 (4)
C2—C7—C8—C1	0.2 (3)	C12—C11—C16—C15	54.9 (4)
C2—C7—C8—C9	−178.4 (3)	C12—C13—C14—C15	−56.4 (4)
C3—C2—C7—C6	−1.0 (4)	C13—C14—C15—C16	54.5 (4)
C3—C2—C7—C8	179.3 (3)	C14—C15—C16—C11	−54.9 (4)
C3—C4—C5—C6	−1.0 (5)	C16—C11—C12—C13	−56.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.86 (1)	2.22 (2)	3.069 (4)	167 (3)

Symmetry code: (i) −x+1, y−1/2, −z+1.

N-[2-(1H-Indol-3-yl)ethyl]cyclohexanaminium bromide (II) top

Crystal data top

C₁₆H₂₃N₂⁺·Br⁻	F(000) = 672
M_r = 323.27	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.5584 (6) Å	Cell parameters from 9846 reflections
b = 7.9266 (5) Å	θ = 2.8–26.3°
c = 19.4507 (13) Å	µ = 2.52 mm⁻¹
β = 92.406 (2)°	T = 297 K
V = 1626.44 (18) Å³	Block, colourless
Z = 4	0.3 × 0.13 × 0.03 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	2978 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.037
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 26.4°, θ_min = 3.2°
T_min = 0.610, T_max = 0.745	h = −13→13
46579 measured reflections	k = −9→9
3320 independent reflections	l = −24→24

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + 4.8013P] where P = (F_o² + 2F_c²)/3
S = 1.22	(Δ/σ)_max = 0.001
3320 reflections	Δρ_max = 0.58 e Å⁻³
184 parameters	Δρ_min = −0.70 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.81840 (4)	0.64728 (5)	0.83341 (2)	0.04595 (14)
N1	0.1405 (3)	0.7180 (5)	0.8197 (2)	0.0510 (9)
N2	0.6414 (3)	0.7350 (4)	0.69368 (18)	0.0362 (7)
C1	0.2277 (4)	0.7985 (6)	0.7822 (2)	0.0514 (11)
H1A	0.208468	0.877881	0.748124	0.062*
C2	0.2018 (4)	0.6091 (5)	0.8650 (2)	0.0397 (9)
C3	0.1549 (5)	0.5037 (6)	0.9141 (2)	0.0542 (12)
H3	0.068295	0.495965	0.920528	0.065*
C4	0.2401 (6)	0.4109 (7)	0.9529 (3)	0.0680 (15)
H4	0.211162	0.339725	0.986910	0.082*
C5	0.3704 (6)	0.4212 (7)	0.9425 (3)	0.0709 (15)
H5	0.425959	0.354368	0.968979	0.085*
C6	0.4180 (5)	0.5268 (6)	0.8944 (2)	0.0544 (11)
H6	0.504805	0.534207	0.888792	0.065*
C7	0.3330 (4)	0.6233 (5)	0.85403 (19)	0.0364 (8)
C8	0.3467 (4)	0.7472 (5)	0.8011 (2)	0.0391 (9)
C9	0.4690 (4)	0.8051 (6)	0.7726 (2)	0.0461 (10)
H9A	0.533883	0.809465	0.809400	0.055*
H9B	0.458286	0.918033	0.754113	0.055*
C10	0.5116 (4)	0.6891 (6)	0.7169 (2)	0.0443 (10)
H10A	0.451375	0.694700	0.677896	0.053*
H10B	0.512820	0.574023	0.733848	0.053*
C11	0.6844 (4)	0.6344 (5)	0.6336 (2)	0.0398 (9)
H11	0.666538	0.515102	0.642099	0.048*
C12	0.6154 (4)	0.6853 (6)	0.5674 (2)	0.0481 (11)
H12A	0.630562	0.803842	0.558442	0.058*
H12B	0.524985	0.669392	0.571593	0.058*
C13	0.6611 (5)	0.5796 (7)	0.5079 (3)	0.0591 (13)
H13A	0.639096	0.462249	0.515003	0.071*
H13B	0.618863	0.616791	0.465273	0.071*
C14	0.8031 (5)	0.5951 (7)	0.5020 (2)	0.0616 (14)
H14A	0.830564	0.521421	0.465755	0.074*
H14B	0.824146	0.710124	0.489862	0.074*
C15	0.8720 (5)	0.5486 (8)	0.5691 (3)	0.0676 (15)
H15A	0.962363	0.565437	0.564858	0.081*
H15B	0.857931	0.430226	0.578863	0.081*
C16	0.8262 (4)	0.6553 (7)	0.6284 (2)	0.0559 (12)
H16A	0.868998	0.620155	0.671109	0.067*
H16B	0.846249	0.772986	0.620616	0.067*
H2A	0.692 (3)	0.722 (6)	0.7316 (13)	0.045 (12)*
H1	0.0593 (14)	0.738 (6)	0.815 (2)	0.058 (14)*
H2B	0.636 (4)	0.844 (2)	0.681 (2)	0.045 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0447 (2)	0.0384 (2)	0.0545 (3)	0.00711 (19)	−0.00029 (17)	−0.0026 (2)
N1	0.0337 (18)	0.062 (2)	0.058 (2)	0.0049 (18)	0.0068 (17)	0.014 (2)
N2	0.0331 (17)	0.0334 (18)	0.0425 (19)	−0.0013 (14)	0.0062 (14)	0.0008 (15)
C1	0.048 (2)	0.057 (3)	0.050 (3)	0.008 (2)	0.009 (2)	0.015 (2)
C2	0.043 (2)	0.037 (2)	0.039 (2)	−0.0032 (17)	0.0058 (17)	−0.0037 (17)
C3	0.058 (3)	0.051 (3)	0.055 (3)	−0.017 (2)	0.012 (2)	0.000 (2)
C4	0.091 (4)	0.053 (3)	0.061 (3)	−0.016 (3)	0.007 (3)	0.019 (3)
C5	0.081 (4)	0.059 (3)	0.071 (4)	0.007 (3)	−0.013 (3)	0.019 (3)
C6	0.053 (3)	0.052 (3)	0.058 (3)	0.003 (2)	−0.003 (2)	0.003 (2)
C7	0.039 (2)	0.034 (2)	0.037 (2)	−0.0008 (16)	0.0027 (16)	−0.0057 (16)
C8	0.039 (2)	0.041 (2)	0.039 (2)	0.0003 (17)	0.0087 (16)	−0.0034 (17)
C9	0.046 (2)	0.044 (2)	0.050 (2)	−0.0042 (19)	0.0143 (19)	−0.004 (2)
C10	0.037 (2)	0.051 (3)	0.047 (2)	−0.0087 (19)	0.0136 (18)	−0.004 (2)
C11	0.045 (2)	0.0282 (19)	0.047 (2)	0.0044 (17)	0.0153 (17)	0.0061 (17)
C12	0.044 (2)	0.052 (3)	0.049 (2)	0.007 (2)	0.0075 (19)	−0.006 (2)
C13	0.064 (3)	0.059 (3)	0.054 (3)	0.004 (3)	0.009 (2)	−0.011 (2)
C14	0.064 (3)	0.073 (4)	0.050 (3)	0.011 (3)	0.026 (2)	0.001 (2)
C15	0.051 (3)	0.084 (4)	0.070 (3)	0.021 (3)	0.029 (2)	0.005 (3)
C16	0.040 (2)	0.068 (3)	0.060 (3)	0.011 (2)	0.012 (2)	0.010 (3)

Geometric parameters (Å, º) top

N1—C1	1.358 (6)	C9—H9B	0.9700
N1—C2	1.375 (5)	C9—C10	1.504 (6)
N1—H1	0.873 (10)	C10—H10A	0.9700
N2—C10	1.506 (5)	C10—H10B	0.9700
N2—C11	1.501 (5)	C11—H11	0.9800
N2—H2A	0.898 (10)	C11—C12	1.506 (6)
N2—H2B	0.900 (10)	C11—C16	1.515 (6)
C1—H1A	0.9300	C12—H12A	0.9700
C1—C8	1.357 (6)	C12—H12B	0.9700
C2—C3	1.376 (6)	C12—C13	1.525 (6)
C2—C7	1.415 (5)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C3—C4	1.366 (7)	C13—C14	1.513 (7)
C4—H4	0.9300	C14—H14A	0.9700
C4—C5	1.402 (8)	C14—H14B	0.9700
C5—H5	0.9300	C14—C15	1.513 (7)
C5—C6	1.366 (7)	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
C6—C7	1.396 (6)	C15—C16	1.525 (7)
C7—C8	1.434 (6)	C16—H16A	0.9700
C8—C9	1.499 (5)	C16—H16B	0.9700
C9—H9A	0.9700

C1—N1—C2	109.2 (4)	C9—C10—N2	111.8 (3)
C1—N1—H1	123 (3)	C9—C10—H10A	109.3
C2—N1—H1	128 (3)	C9—C10—H10B	109.3
C10—N2—H2A	104 (3)	H10A—C10—H10B	107.9
C10—N2—H2B	105 (3)	N2—C11—H11	108.3
C11—N2—C10	114.5 (3)	N2—C11—C12	111.9 (3)
C11—N2—H2A	113 (3)	N2—C11—C16	109.0 (4)
C11—N2—H2B	109 (3)	C12—C11—H11	108.3
H2A—N2—H2B	111 (4)	C12—C11—C16	111.0 (3)
N1—C1—H1A	124.6	C16—C11—H11	108.3
C8—C1—N1	110.7 (4)	C11—C12—H12A	109.6
C8—C1—H1A	124.6	C11—C12—H12B	109.6
N1—C2—C3	130.7 (4)	C11—C12—C13	110.2 (4)
N1—C2—C7	106.9 (3)	H12A—C12—H12B	108.1
C3—C2—C7	122.4 (4)	C13—C12—H12A	109.6
C2—C3—H3	121.2	C13—C12—H12B	109.6
C4—C3—C2	117.6 (5)	C12—C13—H13A	109.4
C4—C3—H3	121.2	C12—C13—H13B	109.4
C3—C4—H4	119.5	H13A—C13—H13B	108.0
C3—C4—C5	121.1 (5)	C14—C13—C12	111.0 (4)
C5—C4—H4	119.5	C14—C13—H13A	109.4
C4—C5—H5	119.1	C14—C13—H13B	109.4
C6—C5—C4	121.8 (5)	C13—C14—H14A	109.4
C6—C5—H5	119.1	C13—C14—H14B	109.4
C5—C6—H6	120.8	H14A—C14—H14B	108.0
C5—C6—C7	118.4 (5)	C15—C14—C13	111.0 (4)
C7—C6—H6	120.8	C15—C14—H14A	109.4
C2—C7—C8	106.9 (3)	C15—C14—H14B	109.4
C6—C7—C2	118.8 (4)	C14—C15—H15A	109.4
C6—C7—C8	134.2 (4)	C14—C15—H15B	109.4
C1—C8—C7	106.3 (4)	C14—C15—C16	111.1 (4)
C1—C8—C9	127.6 (4)	H15A—C15—H15B	108.0
C7—C8—C9	126.1 (4)	C16—C15—H15A	109.4
C8—C9—H9A	109.3	C16—C15—H15B	109.4
C8—C9—H9B	109.3	C11—C16—C15	109.6 (4)
C8—C9—C10	111.6 (3)	C11—C16—H16A	109.7
H9A—C9—H9B	108.0	C11—C16—H16B	109.7
C10—C9—H9A	109.3	C15—C16—H16A	109.7
C10—C9—H9B	109.3	C15—C16—H16B	109.7
N2—C10—H10A	109.3	H16A—C16—H16B	108.2
N2—C10—H10B	109.3

N1—C1—C8—C7	0.8 (5)	C4—C5—C6—C7	−1.5 (8)
N1—C1—C8—C9	−179.9 (4)	C5—C6—C7—C2	0.6 (7)
N1—C2—C3—C4	−178.8 (5)	C5—C6—C7—C8	178.3 (5)
N1—C2—C7—C6	179.1 (4)	C6—C7—C8—C1	−178.9 (5)
N1—C2—C7—C8	0.9 (4)	C6—C7—C8—C9	1.8 (8)
N2—C11—C12—C13	−179.6 (4)	C7—C2—C3—C4	0.0 (7)
N2—C11—C16—C15	177.9 (4)	C7—C8—C9—C10	84.2 (5)
C1—N1—C2—C3	178.5 (5)	C8—C9—C10—N2	−173.5 (4)
C1—N1—C2—C7	−0.4 (5)	C10—N2—C11—C12	73.0 (4)
C1—C8—C9—C10	−95.0 (6)	C10—N2—C11—C16	−163.9 (4)
C2—N1—C1—C8	−0.3 (6)	C11—N2—C10—C9	−174.5 (3)
C2—C3—C4—C5	−0.8 (8)	C11—C12—C13—C14	−56.6 (5)
C2—C7—C8—C1	−1.0 (5)	C12—C11—C16—C15	−58.5 (5)
C2—C7—C8—C9	179.6 (4)	C12—C13—C14—C15	55.5 (6)
C3—C2—C7—C6	0.1 (6)	C13—C14—C15—C16	−56.0 (6)
C3—C2—C7—C8	−178.2 (4)	C14—C15—C16—C11	57.0 (6)
C3—C4—C5—C6	1.6 (9)	C16—C11—C12—C13	58.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Br1	0.90 (1)	2.41 (1)	3.307 (4)	172 (4)
N1—H1···Br1ⁱ	0.87 (1)	2.68 (3)	3.468 (4)	151 (4)
N2—H2B···Br1ⁱⁱ	0.90 (1)	2.47 (2)	3.340 (3)	163 (4)

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

Bis{N-[2-(1H-indol-3-yl)ethyl]cyclohexanaminium} (2E)-but-2-enedioate (III) top

Crystal data top

C₁₆H₂₃N₂⁺·C₂HO₂⁻	F(000) = 648
M_r = 300.39	D_x = 1.186 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.2231 (10) Å	Cell parameters from 7849 reflections
b = 16.1611 (16) Å	θ = 2.6–26.3°
c = 11.4595 (12) Å	µ = 0.08 mm⁻¹
β = 99.865 (4)°	T = 297 K
V = 1682.8 (3) Å³	Block, bronze
Z = 4	0.32 × 0.22 × 0.2 mm

Data collection top

Bruker D8 Venture CMOS diffractometer	2803 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.028
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 26.4°, θ_min = 2.6°
T_min = 0.694, T_max = 0.745	h = −11→11
20060 measured reflections	k = −20→20
3446 independent reflections	l = −14→14

Refinement top

Refinement on F²	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.057P)² + 0.4152P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3446 reflections	Δρ_max = 0.22 e Å⁻³
211 parameters	Δρ_min = −0.17 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.72753 (11)	0.47420 (7)	0.97368 (12)	0.0632 (3)
O4	0.74997 (12)	0.60453 (6)	1.03308 (11)	0.0600 (3)
N1	0.33759 (16)	0.73002 (8)	0.54717 (12)	0.0530 (3)
N2	0.46996 (12)	0.42877 (7)	0.83748 (10)	0.0402 (3)
C1	0.43744 (18)	0.68408 (10)	0.62215 (13)	0.0522 (4)
H1A	0.513836	0.706133	0.676833	0.063*
C2	0.24236 (16)	0.67738 (9)	0.48012 (12)	0.0444 (3)
C3	0.12270 (18)	0.69461 (11)	0.39157 (14)	0.0589 (4)
H3	0.095302	0.748764	0.371017	0.071*
C4	0.0471 (2)	0.62879 (15)	0.33603 (17)	0.0753 (5)
H4	−0.032377	0.638517	0.275820	0.090*
C5	0.0863 (2)	0.54759 (14)	0.36747 (19)	0.0780 (6)
H5	0.032566	0.504233	0.327913	0.094*
C6	0.20302 (19)	0.53036 (10)	0.45603 (16)	0.0609 (4)
H6	0.227496	0.475901	0.477033	0.073*
C7	0.28409 (15)	0.59569 (8)	0.51382 (12)	0.0426 (3)
C8	0.41022 (16)	0.60185 (9)	0.60614 (12)	0.0452 (3)
C9	0.48890 (17)	0.53145 (10)	0.67518 (14)	0.0523 (4)
H9A	0.584225	0.550063	0.715932	0.063*
H9B	0.504732	0.487268	0.621464	0.063*
C10	0.39908 (16)	0.49921 (9)	0.76478 (13)	0.0475 (3)
H10A	0.382929	0.544073	0.817299	0.057*
H10B	0.303662	0.481452	0.723096	0.057*
C11	0.50069 (15)	0.35126 (8)	0.77365 (12)	0.0423 (3)
H11	0.565930	0.364743	0.717251	0.051*
C12	0.57867 (19)	0.29119 (10)	0.86470 (15)	0.0577 (4)
H12A	0.519809	0.282701	0.926173	0.069*
H12B	0.672434	0.314467	0.901290	0.069*
C13	0.6045 (2)	0.20810 (11)	0.80791 (19)	0.0785 (6)
H13A	0.671411	0.215725	0.752071	0.094*
H13B	0.649859	0.169933	0.868687	0.094*
C14	0.4613 (3)	0.17171 (11)	0.74422 (18)	0.0784 (6)
H14A	0.480951	0.120240	0.706292	0.094*
H14B	0.397404	0.159654	0.801073	0.094*
C15	0.3856 (3)	0.23094 (13)	0.65269 (16)	0.0783 (6)
H15A	0.291923	0.207658	0.615817	0.094*
H15B	0.445353	0.238438	0.591619	0.094*
C16	0.35933 (18)	0.31489 (11)	0.70660 (14)	0.0584 (4)
H16A	0.317379	0.352639	0.644040	0.070*
H16B	0.289125	0.308535	0.760051	0.070*
C17	0.80163 (14)	0.53717 (8)	1.00368 (12)	0.0397 (3)
C18	0.96469 (14)	0.53303 (8)	1.01170 (12)	0.0401 (3)
H18	1.019151	0.580476	1.034817	0.048*
H2A	0.5558 (13)	0.4470 (10)	0.8805 (13)	0.061 (5)*
H1	0.330 (2)	0.7840 (6)	0.5455 (17)	0.075 (6)*
H2B	0.4089 (16)	0.4143 (10)	0.8881 (12)	0.057 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0387 (6)	0.0534 (6)	0.0948 (9)	−0.0079 (5)	0.0038 (5)	−0.0168 (6)
O4	0.0520 (6)	0.0374 (5)	0.0972 (9)	0.0050 (4)	0.0316 (6)	−0.0031 (5)
N1	0.0706 (9)	0.0364 (6)	0.0517 (7)	0.0033 (6)	0.0096 (6)	0.0033 (5)
N2	0.0349 (6)	0.0417 (6)	0.0432 (6)	0.0028 (5)	0.0045 (5)	0.0042 (5)
C1	0.0589 (9)	0.0501 (8)	0.0457 (8)	−0.0022 (7)	0.0033 (7)	0.0005 (7)
C2	0.0508 (8)	0.0445 (7)	0.0403 (7)	0.0063 (6)	0.0143 (6)	0.0038 (6)
C3	0.0601 (10)	0.0671 (10)	0.0496 (8)	0.0182 (8)	0.0094 (7)	0.0116 (8)
C4	0.0550 (10)	0.1013 (15)	0.0642 (11)	0.0070 (10)	−0.0047 (8)	0.0026 (11)
C5	0.0691 (12)	0.0806 (14)	0.0785 (13)	−0.0142 (10)	−0.0037 (10)	−0.0156 (11)
C6	0.0632 (10)	0.0485 (9)	0.0706 (10)	−0.0031 (7)	0.0106 (8)	−0.0066 (8)
C7	0.0462 (7)	0.0408 (7)	0.0430 (7)	0.0046 (6)	0.0140 (6)	0.0013 (6)
C8	0.0489 (8)	0.0438 (7)	0.0443 (7)	0.0069 (6)	0.0118 (6)	0.0055 (6)
C9	0.0489 (8)	0.0535 (9)	0.0556 (8)	0.0119 (7)	0.0125 (7)	0.0126 (7)
C10	0.0447 (8)	0.0459 (8)	0.0528 (8)	0.0134 (6)	0.0107 (6)	0.0094 (6)
C11	0.0401 (7)	0.0426 (7)	0.0452 (7)	0.0052 (6)	0.0100 (6)	0.0034 (6)
C12	0.0577 (9)	0.0463 (8)	0.0640 (9)	0.0070 (7)	−0.0046 (7)	0.0086 (7)
C13	0.0968 (15)	0.0521 (10)	0.0886 (13)	0.0254 (10)	0.0213 (12)	0.0133 (10)
C14	0.1227 (18)	0.0475 (10)	0.0713 (12)	−0.0069 (10)	0.0346 (12)	−0.0107 (9)
C15	0.1055 (16)	0.0739 (13)	0.0546 (10)	−0.0116 (11)	0.0112 (10)	−0.0191 (9)
C16	0.0568 (9)	0.0642 (10)	0.0499 (8)	0.0003 (8)	−0.0026 (7)	−0.0062 (7)
C17	0.0356 (6)	0.0357 (7)	0.0482 (7)	0.0013 (5)	0.0082 (5)	0.0001 (5)
C18	0.0363 (7)	0.0346 (6)	0.0493 (7)	−0.0039 (5)	0.0070 (5)	−0.0044 (5)

Geometric parameters (Å, º) top

O2—C17	1.2411 (16)	C9—H9B	0.9700
O4—C17	1.2572 (16)	C9—C10	1.518 (2)
N1—C1	1.366 (2)	C10—H10A	0.9700
N1—C2	1.362 (2)	C10—H10B	0.9700
N1—H1	0.876 (9)	C11—H11	0.9800
N2—C10	1.4935 (17)	C11—C12	1.514 (2)
N2—C11	1.5018 (18)	C11—C16	1.514 (2)
N2—H2A	0.907 (9)	C12—H12A	0.9700
N2—H2B	0.905 (9)	C12—H12B	0.9700
C1—H1A	0.9300	C12—C13	1.529 (2)
C1—C8	1.359 (2)	C13—H13A	0.9700
C2—C3	1.393 (2)	C13—H13B	0.9700
C2—C7	1.4105 (19)	C13—C14	1.514 (3)
C3—H3	0.9300	C14—H14A	0.9700
C3—C4	1.368 (3)	C14—H14B	0.9700
C4—H4	0.9300	C14—C15	1.501 (3)
C4—C5	1.392 (3)	C15—H15A	0.9700
C5—H5	0.9300	C15—H15B	0.9700
C5—C6	1.376 (3)	C15—C16	1.527 (2)
C6—H6	0.9300	C16—H16A	0.9700
C6—C7	1.394 (2)	C16—H16B	0.9700
C7—C8	1.436 (2)	C17—C18	1.4924 (18)
C8—C9	1.5000 (19)	C18—C18ⁱ	1.302 (3)
C9—H9A	0.9700	C18—H18	0.9300

C1—N1—H1	126.9 (13)	H10A—C10—H10B	107.7
C2—N1—C1	108.39 (12)	N2—C11—H11	108.9
C2—N1—H1	124.6 (13)	N2—C11—C12	107.83 (12)
C10—N2—C11	117.72 (11)	N2—C11—C16	110.67 (11)
C10—N2—H2A	108.3 (11)	C12—C11—H11	108.9
C10—N2—H2B	107.1 (11)	C12—C11—C16	111.52 (13)
C11—N2—H2A	108.4 (11)	C16—C11—H11	108.9
C11—N2—H2B	106.6 (11)	C11—C12—H12A	109.4
H2A—N2—H2B	108.5 (15)	C11—C12—H12B	109.4
N1—C1—H1A	124.5	C11—C12—C13	111.11 (14)
C8—C1—N1	110.95 (14)	H12A—C12—H12B	108.0
C8—C1—H1A	124.5	C13—C12—H12A	109.4
N1—C2—C3	129.78 (14)	C13—C12—H12B	109.4
N1—C2—C7	108.12 (12)	C12—C13—H13A	109.4
C3—C2—C7	122.10 (15)	C12—C13—H13B	109.4
C2—C3—H3	121.3	H13A—C13—H13B	108.0
C4—C3—C2	117.42 (16)	C14—C13—C12	111.08 (16)
C4—C3—H3	121.3	C14—C13—H13A	109.4
C3—C4—H4	119.2	C14—C13—H13B	109.4
C3—C4—C5	121.59 (16)	C13—C14—H14A	109.5
C5—C4—H4	119.2	C13—C14—H14B	109.5
C4—C5—H5	119.4	H14A—C14—H14B	108.1
C6—C5—C4	121.16 (18)	C15—C14—C13	110.62 (16)
C6—C5—H5	119.4	C15—C14—H14A	109.5
C5—C6—H6	120.5	C15—C14—H14B	109.5
C5—C6—C7	119.05 (16)	C14—C15—H15A	109.3
C7—C6—H6	120.5	C14—C15—H15B	109.3
C2—C7—C8	106.59 (12)	C14—C15—C16	111.77 (14)
C6—C7—C2	118.68 (14)	H15A—C15—H15B	107.9
C6—C7—C8	134.73 (14)	C16—C15—H15A	109.3
C1—C8—C7	105.96 (12)	C16—C15—H15B	109.3
C1—C8—C9	127.52 (14)	C11—C16—C15	111.59 (15)
C7—C8—C9	126.43 (13)	C11—C16—H16A	109.3
C8—C9—H9A	109.6	C11—C16—H16B	109.3
C8—C9—H9B	109.6	C15—C16—H16A	109.3
C8—C9—C10	110.27 (12)	C15—C16—H16B	109.3
H9A—C9—H9B	108.1	H16A—C16—H16B	108.0
C10—C9—H9A	109.6	O2—C17—O4	124.62 (13)
C10—C9—H9B	109.6	O2—C17—C18	118.79 (12)
N2—C10—C9	113.68 (11)	O4—C17—C18	116.52 (12)
N2—C10—H10A	108.8	C17—C18—H18	118.0
N2—C10—H10B	108.8	C18ⁱ—C18—C17	123.95 (16)
C9—C10—H10A	108.8	C18ⁱ—C18—H18	118.0
C9—C10—H10B	108.8

O2—C17—C18—C18ⁱ	0.5 (3)	C3—C4—C5—C6	0.0 (3)
O4—C17—C18—C18ⁱ	177.60 (18)	C4—C5—C6—C7	−0.8 (3)
N1—C1—C8—C7	0.23 (17)	C5—C6—C7—C2	0.7 (2)
N1—C1—C8—C9	−176.30 (14)	C5—C6—C7—C8	−178.90 (17)
N1—C2—C3—C4	178.46 (16)	C6—C7—C8—C1	179.25 (17)
N1—C2—C7—C6	−179.33 (14)	C6—C7—C8—C9	−4.2 (3)
N1—C2—C7—C8	0.35 (16)	C7—C2—C3—C4	−1.0 (2)
N2—C11—C12—C13	176.04 (14)	C7—C8—C9—C10	−74.77 (19)
N2—C11—C16—C15	−173.47 (13)	C8—C9—C10—N2	180.00 (12)
C1—N1—C2—C3	−179.77 (15)	C10—N2—C11—C12	177.27 (12)
C1—N1—C2—C7	−0.21 (16)	C10—N2—C11—C16	−60.50 (16)
C1—C8—C9—C10	101.09 (19)	C11—N2—C10—C9	−60.41 (17)
C2—N1—C1—C8	−0.02 (18)	C11—C12—C13—C14	−56.1 (2)
C2—C3—C4—C5	0.9 (3)	C12—C11—C16—C15	−53.43 (19)
C2—C7—C8—C1	−0.35 (16)	C12—C13—C14—C15	56.9 (2)
C2—C7—C8—C9	176.23 (13)	C13—C14—C15—C16	−56.1 (2)
C3—C2—C7—C6	0.3 (2)	C14—C15—C16—C11	54.6 (2)
C3—C2—C7—C8	179.95 (13)	C16—C11—C12—C13	54.34 (19)

Symmetry code: (i) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.91 (1)	1.81 (1)	2.7107 (15)	175 (2)
N1—H1···O4ⁱⁱ	0.88 (1)	1.94 (1)	2.7899 (16)	163 (2)
N2—H2B···O4ⁱⁱⁱ	0.91 (1)	1.87 (1)	2.7632 (16)	167 (2)

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

Selected metrical parameters (Å, °) for (I)—(III) top

Compound	indole r.m.s. deviation from planarity	C7—C8—C9—C10	C10—N2—C11
(I)	0.007	45.5 (4)	116.6 (3)
(II)	0.010	84.2 (5)	114.5 (3)
(III)	0.008	-74.77 (19)	117.72 (11)

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N-Cyclo­hexyl­tryptamine: freebase, bromide and fumarate

Supporting information

Key indicators

checkCIF/PLATON results

N-Cyclohexyltryptamine: freebase, bromide and fumarate